Advances in Natural Products from Plants and Associated Microbes

Topic Information

Dear Colleagues,

Plant natural products have proved effective in treating different health-related diseases that affect humans. Recent literature confirms that plant-derived natural products are still under-represented in some aspects, such as antibiotics, which are mainly covered by microbial natural products. Microbial natural products are also integral to human health in the form of medicines such as antibiotics, antifungals, immunosuppressants, and anticancer agents. However, the microbial natural products of diverse microbes remain largely under-investigated. In particular, endophytes, microorganisms that reside in the tissues of living plants, and marine-derived microbes are sources of novel natural products that could potentially be exploited in natural product chemistry. The use of computer-assisted drug discovery programs such as docking and molecular dynamics simulations has helped us to discover known plant and microbial metabolites with promising new biological activities which have been validated by in vitro or in vivo analyses. Moreover, nano-formulations of natural products have enhanced their delivery and improved their associated biological activity. This Topic mainly aims to focus on the targeted discovery of new or known plant and microbial bioactive metabolites through the use of biology-guided isolation, computer-aided programs, or nano-formulations with enhanced delivery and activity).

Dr. Ki Hyun Kim
Dr. Mostafa Rateb
Dr. Hossam Hassan
Topic Editors

Keywords

Participating Journals

Journal Name	Impact Factor	CiteScore	Launched Year	First Decision (median)	APC
Biomedicines biomedicines	4.7	3.7	2013	15.4 Days	CHF 2600
Marine Drugs marinedrugs	5.4	9.6	2003	14 Days	CHF 2900
Molecules molecules	4.6	6.7	1996	14.6 Days	CHF 2700
Pharmaceutics pharmaceutics	5.4	6.9	2009	14.2 Days	CHF 2900
Plants plants	4.5	5.4	2012	15.3 Days	CHF 2700

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12 pages, 3716 KiB  

Open AccessArticle

Eupalinolide J Inhibits Cancer Metastasis by Promoting STAT3 Ubiquitin-Dependent Degradation

by Hongtao Hu, Haoyang Bai, Lili Huang, Bo Yang and Huajun Zhao

Molecules 2023, 28(7), 3143; https://doi.org/10.3390/molecules28073143 - 31 Mar 2023

Viewed by 1262

Abstract

Eupalinolide J (EJ) is an active component from Eupatorium lindleyanum DC. (EL), which was reported to have good antitumor activity via STAT3 and Akt signaling pathways. In this study, we identified Eupalinolide J (EJ) as a potential anti-cancer metastatic agent by target prediction [...] Read more.

Eupalinolide J (EJ) is an active component from Eupatorium lindleyanum DC. (EL), which was reported to have good antitumor activity via STAT3 and Akt signaling pathways. In this study, we identified Eupalinolide J (EJ) as a potential anti-cancer metastatic agent by target prediction and molecular docking technique screening. Follow-up experiments demonstrated that EJ exhibited a good inhibitory effect on cancer cell metastasis both in vitro and in vivo, and could effectively reduce the expression of STAT3, MMP-2, and MMP-9 proteins in cells, while the knockdown of STAT3 could weaken the inhibitory effect of EJ on cancer cell metastasis. Further molecular biology experiments revealed that EJ promoted STAT3 ubiquitin-dependent degradation, and thus, downregulated the expression of the metastasis-related genes MMP-2 and MMP-9. In conclusion, our study revealed that EJ, a sesquiterpene lactone from EL, could act as a STAT3 degradation agent to inhibit cancer cell metastasis and is expected to be applied in cancer therapy. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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12 pages, 1311 KiB  

Open AccessArticle

Antibacterial, Antibiofilm and Anti-Inflammatory Activities of Eugenol Clove Essential Oil against Resistant Helicobacter pylori

by Mahmoud K. M. Elbestawy, Gamal M. El-Sherbiny and Saad A. Moghannem

Molecules 2023, 28(6), 2448; https://doi.org/10.3390/molecules28062448 - 07 Mar 2023

Cited by 9 | Viewed by 3117

Abstract

Eugenol essential oil (EEO) is the major component in aromatic extracts of Syzygium aromaticum (clove) and has several biological properties, such as antibacterial, antioxidant, and anti-inflammatory activities, as well as controlling vomiting, coughing, nausea, flatulence, diarrhea, dyspepsia, stomach distension, and gastrointestinal spasm pain. [...] Read more.

Eugenol essential oil (EEO) is the major component in aromatic extracts of Syzygium aromaticum (clove) and has several biological properties, such as antibacterial, antioxidant, and anti-inflammatory activities, as well as controlling vomiting, coughing, nausea, flatulence, diarrhea, dyspepsia, stomach distension, and gastrointestinal spasm pain. It also stimulates the nerves. Therefore, the aim of this study was to extract and purify EEO from clove buds and assess its ability to combat resistant Helicobacter pylori. Additionally, EEO’s anti-inflammatory activity and its ability to suppress H. pylori biofilm formation, which is responsible for antibiotic resistance, was also investigated. Syzygium aromaticum buds were purchased from a local market, ground, and the EEO was extracted by using hydro-distillation and then purified and chemically characterized using gas chromatography–mass spectrometry (GC–MS). A disk-diffusion assay showed that Helicobacter pylori is sensitive to EEO, with an inhibition zone ranging from 10 ± 06 to 22 ± 04 mm. The minimum inhibition concentration (MIC) of EEO ranged from 23.0 to 51.0 μg/mL against both Helicobacter pylori clinical isolates and standard strains. In addition, EEO showed antibiofilm activity at 25 µg/mL and 50 µg/mL against various Helicobacter pylori strains, with suppression percentages of 49.32% and 73.21%, respectively. The results obtained from the anti-inflammatory assay revealed that EEO possesses strong anti-inflammatory activity, with human erythrocyte hemolysis inhibition percentages of 53.04, 58.74, 61.07, and 63.64% at concentrations of 4, 8, 16, and 32 μg/L, respectively. GC–MS analysis revealed that EEO is a major component of Syzygium aromaticum when extracted with a hydro-distillation technique, which was confirmed by its purification using a chemical separation process. EEO exhibited antibacterial action against resistant Helicobacter pylori strains, as well as antibiofilm and anti-inflammatory activities, and is a promising natural alternative in clinical therapy. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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17 pages, 2041 KiB  

Open AccessReview

Traveling across Life Sciences with Acetophenone—A Simple Ketone That Has Special Multipurpose Missions

by Fedor I. Zubkov and Vladimir V. Kouznetsov

Molecules 2023, 28(1), 370; https://doi.org/10.3390/molecules28010370 - 02 Jan 2023

Cited by 8 | Viewed by 2626

Abstract

Each metabolite, regardless of its molecular simplicity or complexity, has a mission or function in the organism biosynthesizing it. In this review, the biological, allelochemical, and chemical properties of acetophenone, as a metabolite involved in multiple interactions with various (mi-cro)organisms, are discussed. Further, [...] Read more.

Each metabolite, regardless of its molecular simplicity or complexity, has a mission or function in the organism biosynthesizing it. In this review, the biological, allelochemical, and chemical properties of acetophenone, as a metabolite involved in multiple interactions with various (mi-cro)organisms, are discussed. Further, the details of its biogenesis and chemical synthesis are provided, and the possibility of its application in different areas of life sciences, i.e., the status quo of acetophenone and its simple substituted analogs, is examined. In particular, natural and synthetic simple acetophenone derivatives are analyzed as promising agrochemicals and useful scaffolds for drug research and development. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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11 pages, 1360 KiB  

Open AccessArticle

Antimicrobial Activity of Smilax china L. Root Extracts against the Acne-Causing Bacterium, Cutibacterium acnes, and Its Active Compounds

by Ji-Hae Joo, Min-Hui Han, Ja-I Kim, Jong-Eun Kim, Kyung-Hwan Jung, Han Sun Oh, Young Soo Chung, Hyun Jin An, Jae Duk Lee, Gi-Seong Moon and Hyang-Yeol Lee

Molecules 2022, 27(23), 8331; https://doi.org/10.3390/molecules27238331 - 29 Nov 2022

Cited by 2 | Viewed by 2122

Abstract

The root of Smilax china L. is used in traditional Korean medicine. We found that the Smilax china L. root extract has strong antimicrobial activity against two Cutibacterium acnes strains (KCTC 3314 and KCTC 3320). The aim of this study was to identify [...] Read more.

The root of Smilax china L. is used in traditional Korean medicine. We found that the Smilax china L. root extract has strong antimicrobial activity against two Cutibacterium acnes strains (KCTC 3314 and KCTC 3320). The aim of this study was to identify the beneficial properties of Smilax china L. extracts for their potential use as active ingredients in cosmetics for the treatment of human skin acne. The high-performance liquid chromatography (HPLC) and liquid chromatography-hybrid quadrupole time-of-flight mass spectrometry (LC/QTOF/MS) methods were used to obtain the profile of secondary metabolites from the ethyl acetate-soluble fraction of the crude extract. Agar diffusion and resazurin-based broth microdilution assays were used to evaluate antimicrobial activity and minimum inhibitory concentrations (MIC), respectively. Among the 24 metabolites, quercetin, resveratrol, and oxyresveratrol were the most potent compounds against Cutibacterium acnes. Minimum inhibitory concentrations of quercetin, resveratrol, and oxyresveratrol were 31.25, 125, and 250 μg/mL, respectively. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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14 pages, 1997 KiB  

Open AccessReview

Potential Role of Host Microbiome in Areca Nut-Associated Carcinogenesis and Addiction

by Lihui Chen, Fulai Yuan, Sifang Chen, Xiong Li, Lingyu Kong and Wei Zhang

Molecules 2022, 27(23), 8171; https://doi.org/10.3390/molecules27238171 - 24 Nov 2022

Cited by 3 | Viewed by 2173

Abstract

Areca nut (AN) is widely consumed all over the world, bringing great harm to human health and economy. Individuals with AN chewing are at high risk of cardiovascular disease and impaired immune system and metabolic system. Despite a growing number of studies having [...] Read more.

Areca nut (AN) is widely consumed all over the world, bringing great harm to human health and economy. Individuals with AN chewing are at high risk of cardiovascular disease and impaired immune system and metabolic system. Despite a growing number of studies having reported on the adverse effects brought by AN chewing, the exact mechanism of it is limited and the need for additional exploration remains. In recent years, the interaction between microorganisms, especially intestinal microorganism and host, has been extensively studied. AN chewing might disrupt the oral and intestinal microbiota communities through direct connect with the microbes it contains, altering PH, oxygen of oral and intestinal microenvironment, and disturbing the immune homeostasis. These mechanisms provide insights into the interplay between areca nut and host microbiota. Emerging studies have proposed that bidirectional interaction between polyphenols and intestinal microbes might play a potential role in the divergence of polyphenol, extracted from AN, among individuals with or without AN-induced cancer development and progression. Although some AN chewers have been aware of the harmful effects brought by AN, they cannot abolish this habit because of the addiction of AN. Increasing studies have tried to revealed that gut microbiota might influence the onset/development of addictive behaviors. Altogether, this review summarizes the possible reasons for the disturbance of host microbiota caused by areca nut chewing and clarifies the complex interaction between human microbiome and major constituents and the addiction and carcinogenicity of AN, tempting to provide novel insights into the development and utilization of it, and to control the adverse consequences caused by AN chewing. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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17 pages, 7883 KiB  

Open AccessEditor’s ChoiceArticle

Eucalyptus cinerea and E. nicholii by-Products as Source of Bioactive Compounds for Agricultural Applications

by Paola Malaspina, Marina Papaianni, Marta Ranesi, Flavio Polito, Cristina Danna, Pierluca Aicardi, Laura Cornara, Sheridan L. Woo and Vincenzo De Feo

Plants 2022, 11(20), 2777; https://doi.org/10.3390/plants11202777 - 20 Oct 2022

Cited by 5 | Viewed by 1627

Abstract

The cultivation of different species of Eucalyptus has recently expanded in Liguria (Italy) due to the growing demand of the North European floricultural market. Eucalyptus tree branches are cut and selected for their quality, resulting in large amounts of waste biomass to be [...] Read more.

The cultivation of different species of Eucalyptus has recently expanded in Liguria (Italy) due to the growing demand of the North European floricultural market. Eucalyptus tree branches are cut and selected for their quality, resulting in large amounts of waste biomass to be disposed of. The aim of our study was to evaluate the phytotoxic and antimicrobial activities of essential oils (EOs) from pruning wastes of E. cinerea (EC) and E. nicholii (EN), for potential applications in agriculture. Phytochemical analyses showed eucalyptol (1,8-cineole) as the major component in both EOs, but the EO yield of EN was higher than that of EC, in agreement with a significantly higher oil gland density on EN leaves. EOs from both species showed phytotoxicity on both weeds tested, but no significant inhibition on horticultural crop seed germination, except for Raphanus sativus. The EO from EC showed the strongest antibacterial activity, while the EO from EN showed the strongest antifungal activity. Concluding, EOs from Eucalyptus pruning may be used as possible alternatives to synthetic herbicides and pesticides, acting as antimicrobial and antifungal agents, thus representing a safe strategy for crop management programs. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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21 pages, 6206 KiB  

Open AccessArticle

Torularhodin Alleviates Hepatic Dyslipidemia and Inflammations in High-Fat Diet-Induced Obese Mice via PPARα Signaling Pathway

by Xingming Li, Yuliang Cheng, Jiayi Li, Chang Liu, He Qian and Genyi Zhang

Molecules 2022, 27(19), 6398; https://doi.org/10.3390/molecules27196398 - 27 Sep 2022

Cited by 5 | Viewed by 2249

Abstract

Torularhodin is a β-carotene-like compound from Sporidiobolus pararoseus, and its protective effect against high-fat diet (HFD)-induced hepatic dyslipidemia and inflammation was investigated. Compared to mice of C57BL/6J fed on HFD, the addition of Torularhodin into the HFD (HFD-T) significantly reduced body weight, serum [...] Read more.

Torularhodin is a β-carotene-like compound from Sporidiobolus pararoseus, and its protective effect against high-fat diet (HFD)-induced hepatic dyslipidemia and inflammation was investigated. Compared to mice of C57BL/6J fed on HFD, the addition of Torularhodin into the HFD (HFD-T) significantly reduced body weight, serum triglyceride (TG), total cholesterol (TC), low-density lipoprotein (LDL), and the inflammatory mediators of TNF-α, IL-6, IL-1β, and lipopolysaccharide (LPS). A significant increase of high-density lipoprotein cholesterol (HDL-c), which is beneficial to cholesterol clearance, was also observed in HFD-T group. Proteomic analysis showed HDL-C-c is highly correlated with proteins (e.g., CPT1A and CYP7A1) involved in lipid β-oxidation and bile acid synthesis, whereas the other phenotypic parameters (TC, TG, LDL, and inflammatory cytokines) are highly associated with proteins (e.g., SLC27A4) involved in lipid-uptake. The up-regulated anti-inflammation proteins FAS, BAX, ICAM1, OCLN, GSTP1, FAF1, LRP1, APEX1, ROCK1, MANF, STAT3, and INSR and down-regulated pro-inflammatory proteins OPTN, PTK2B, FADD, MIF, CASP3, YAP1, DNM1L, and NAMPT not only demonstrate the occurrence of HFD-induced hepatic inflammation, but also prove the anti-inflammatory property of Torularhodin. KEGG signaling pathway analysis revealed that the PPARα signaling pathway is likely fundamental to the health function of Torularhodin through up-regulating genes related to fatty acid β-oxidation, cholesterol excretion, HDL-Cc formation, and anti-inflammation. Torularhodin, as a new food resource, may act as a therapeutic agent to prevent hepatic dyslipidemia and related inflammation for improved health. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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10 pages, 1614 KiB  

Open AccessArticle

Garcinia cambogia Phenolics as Potent Anti-COVID-19 Agents: Phytochemical Profiling, Biological Activities, and Molecular Docking

by Hanan Y. Aati, Ahmed Ismail, Mostafa E. Rateb, Asmaa M. AboulMagd, Hossam M. Hassan and Mona H. Hetta

Plants 2022, 11(19), 2521; https://doi.org/10.3390/plants11192521 - 26 Sep 2022

Cited by 5 | Viewed by 1697

Abstract

COVID-19 is a disease caused by the coronavirus SARS-CoV-2 and became a pandemic in a critically short time. Phenolic secondary metabolites attracted much attention from the pharmaceutical industries for their easily accessible natural sources and proven antiviral activity. In our mission, a metabolomics [...] Read more.

COVID-19 is a disease caused by the coronavirus SARS-CoV-2 and became a pandemic in a critically short time. Phenolic secondary metabolites attracted much attention from the pharmaceutical industries for their easily accessible natural sources and proven antiviral activity. In our mission, a metabolomics study of the Garcinia cambogia Roxb. fruit rind was performed using LC-HRESIMS to investigate its chemical profile, especially the polar aspects, followed by a detailed phytochemical analysis, which led to the isolation of eight known compounds. Using spectrometric techniques, the isolated compounds were identified as quercetin, amentoflavone, vitexin, rutin, naringin, catechin, p-coumaric, and gallic acids. The antiviral activities of the isolated compounds were investigated using two assays; the 3CL-M^pro enzyme showed that naringin had a potent effect with IC₅₀ 16.62 μg/mL, followed by catechin and gallic acid (IC₅₀ 26.2, 30.35 μg/mL, respectively), while the direct antiviral inhibition effect of naringin confirmed the potency with an EC₅₀ of 0.0169 μM. To show the molecular interaction, in situ molecular docking was carried out using a COVID-19 protease enzyme. Both biological effects and docking studies showed the hydrophobic interactions with Gln 189 or Glu 166, per the predicated binding pose of the isolated naringin. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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18 pages, 1539 KiB  

Open AccessArticle

Ultrasonic Extraction of 2-Acetyl-1-Pyrroline (2AP) from Pandanus amaryllifolius Roxb. Using Ethanol as Solvent

by Aisyah Nur Hanis Azhar, Nurul Aini Amran, Suzana Yusup and Mohd Hizami Mohd Yusoff

Molecules 2022, 27(15), 4906; https://doi.org/10.3390/molecules27154906 - 31 Jul 2022

Cited by 8 | Viewed by 2320

Abstract

2-acetyl-1-pyrroline (2AP) is the compound that gives out the typical aroma and flavour of pandan leaves (Pandanus amaryllifolius Roxb.). This research incorporates ultrasonic extraction to extract the aromatic compound in pandan leaves. The parameters varied in this study are the extraction [...] Read more.

2-acetyl-1-pyrroline (2AP) is the compound that gives out the typical aroma and flavour of pandan leaves (Pandanus amaryllifolius Roxb.). This research incorporates ultrasonic extraction to extract the aromatic compound in pandan leaves. The parameters varied in this study are the extraction time, sonicator amplitude, concentration of solvent and the mass of pandan leaves. The experiment was conducted using a central composite design (CCD) model generated by the response surface methodology (RSM). From the extraction process, it can be deduced that the effect of leaves’ mass is comparably higher than other parameters, while sonicator amplitude gives the most negligible impact on the process. The obtained p-value was 0.0014, which was less than 0.05. The high R-squared 0.9603 and adjusted R-squared 0.8809 indicate the model is well agreed with the actual data. The optimal control variables of ultrasonic extraction of 2AP are at an extraction time of 20 min, 60% of solvent concentration, amplitude of 25% and 12.5 g of pandan leaves, which produced 60.51% of yield of the extract and 1.43 ppm of 2AP. It is found that the mass of pandan leaves and the concentration of solvent have a significant impact on the extraction process of 2AP. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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12 pages, 2552 KiB  

Open AccessArticle

Synergistic Effects of Plant Growth Regulators and Elicitors on α-Humulene and Zerumbone Production in Zingiber zerumbet Smith Adventitious Root Cultures

by Nurul Huda Alwakil, Mohamad Suffian Mohamad Annuar and Mahanom Jalil

Molecules 2022, 27(15), 4744; https://doi.org/10.3390/molecules27154744 - 25 Jul 2022

Cited by 4 | Viewed by 1628

Abstract

Zingiber zerumbet, also known as ‘Lempoyang’, possesses various phytomedicinal properties, such as anticancer, antimicrobial, anti-inflammatory, antiulcer, and antioxidant properties. Secondary metabolites possessing such properties i.e., zerumbone and α-humulene, are found dominantly in the plant rhizome. Synergistic effects of plant growth hormones and [...] Read more.

Zingiber zerumbet, also known as ‘Lempoyang’, possesses various phytomedicinal properties, such as anticancer, antimicrobial, anti-inflammatory, antiulcer, and antioxidant properties. Secondary metabolites possessing such properties i.e., zerumbone and α-humulene, are found dominantly in the plant rhizome. Synergistic effects of plant growth hormones and elicitors on in vitro α-humulene and zerumbone production, and biomass growth, in adventitious root culture (AdRC) of Z. zerumbet cultivated in a two-stage culture are reported. The culture was induced by supplementation of 1.0 mg/L NAA and 2.0 mg/L IBA (dark), and subsequently maintained in medium supplemented with 1 mg/L NAA and 3 mg/L BAP (16:08 light-dark cycle), yielded the production of zerumbone at 3440 ± 168 µg/g and α-humulene at 3759 ± 798 µg/g. Synergistic elicitation by 400 μM methyl jasmonate (MeJa) and 400 μM salicylic acid (SA) resulted in a 13-fold increase in zerumbone (43,000 ± 200 µg/g), while 400 μM MeJa and 600 μM SA produced a 4.3-fold increase in α-humulene (15,800 ± 5100 µg/g) compared to control. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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15 pages, 3651 KiB  

Open AccessArticle

Xanthatin Alleviates LPS-Induced Inflammatory Response in RAW264.7 Macrophages by Inhibiting NF-κB, MAPK and STATs Activation

by Yuanqi Liu, Wenyu Chen, Fang Zheng, Huanan Yu and Kun Wei

Molecules 2022, 27(14), 4603; https://doi.org/10.3390/molecules27144603 - 19 Jul 2022

Cited by 16 | Viewed by 2594

Abstract

Xanthatin (XT) is a sesquiterpene lactone isolated from the Chinese herb Xanthium, which belongs to the Asteraceae family. In this study, we developed an inflammation model via stimulating macrophage cell line (RAW 264.7 cells) with lipopolysaccharide (LPS), which was applied to assess the [...] Read more.

Xanthatin (XT) is a sesquiterpene lactone isolated from the Chinese herb Xanthium, which belongs to the Asteraceae family. In this study, we developed an inflammation model via stimulating macrophage cell line (RAW 264.7 cells) with lipopolysaccharide (LPS), which was applied to assess the anti-inflammatory effect and probable mechanisms of xanthatin. When compared with the only LPS-induced group, cells that were pretreated with xanthatin were found to decrease the amount of nitric oxide (NO), reactive oxygen species (ROS) and associated pro-inflammatory factors (TNF-α, IL-1β and IL-6), and downregulate the mRNA expression of iNOS, COX-2, TNF-α, IL-1β, and IL-6. Interestingly, phosphorylated levels of related proteins (STAT3, ERK1/2, SAPK/JNK, IκBα, p65) were notably increased only with the LPS-activated cells, while the expression of these could be reverted by pre-treatment with xanthatin in a dose-dependent way. Meanwhile, xanthatin was also found to block NF-κB p65 from translocating into the nucleus and activating inflammatory gene transcription. Collectively, these results demonstrated that xanthatin suppresses the inflammatory effects through downregulating the nuclear factor kappa-B (NF-κB), mitogen-activated protein kinase (MAPK) and signal transducer and activator of transcription (STATs) signaling pathways. Taken together, xanthatin possesses the potential to act as a good anti-inflammatory medication candidate. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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15 pages, 3508 KiB  

Open AccessArticle

LC/MS Profiling and Gold Nanoparticle Formulation of Major Metabolites from Origanum majorana as Antibacterial and Antioxidant Potentialities

by Ahmed H. El-Ghorab, Fathy A. Behery, Mohamed A. Abdelgawad, Ibrahim Hotan Alsohaimi, Arafa Musa, Ehab M. Mostafa, Hamud A. Altaleb, Ibrahim O. Althobaiti, Mohamed Hamza, Mohammed H. Elkomy, Ahmed A. Hamed, Ahmed M. Sayed, Hossam M. Hassan and Mahmoud A. Aboseada

Plants 2022, 11(14), 1871; https://doi.org/10.3390/plants11141871 - 18 Jul 2022

Cited by 6 | Viewed by 1905

Abstract

Origanum majoranum L. is a Lamiaceae medicinal plant with culinary and ethnomedical applications. Its biological and phytochemical profiles have been extensively researched. Accordingly, this study aimed to investigate the chemical composition and the antibacterial and antioxidant properties of O. majoranum high features, as [...] Read more.

Origanum majoranum L. is a Lamiaceae medicinal plant with culinary and ethnomedical applications. Its biological and phytochemical profiles have been extensively researched. Accordingly, this study aimed to investigate the chemical composition and the antibacterial and antioxidant properties of O. majoranum high features, as well as to search for techniques for activity optimization. A metabolomics study of the crude extract of O. majoranum using liquid chromatography-high-resolution electrospray ionization mass spectrometry (LC ± HR ± ESI ± MS) was conducted. Five fractions (petroleum ether, dichloromethane, ethyl acetate, n-butanol, and aqueous) were derived from the total extract of the aerial parts. Different chromatographic methods and NMR analysis were utilized to purify and identify the isolated phenolics (high features). Moreover, the antimicrobial, antibiofilm, and antioxidant activity of phenolics were performed. Results showed that metabolomic profiling of the crude extract of O. majoranum aerial parts revealed the presence of a variety of phytochemicals, predominantly phenolics, resulting in the isolation and identification of seven high-feature compounds comprising two phenolic acids, rosmarinic and caffeic acids, one phenolic diterpene, 7-methoxyepirosmanol, in addition to four flavonoids, quercetin, hesperitin, hesperidin, and luteolin. On the other hand, 7-methoxyepirosmanol (OM₁) displayed the most antimicrobial and antioxidant potential. Such a phenolic principal activity improvement seems to be established after loading on gold nanoparticles. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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16 pages, 1694 KiB  

Open AccessArticle

Kaempferia parviflora Rhizome Extract as Potential Anti-Acne Ingredient

by Pawee Sitthichai, Setinee Chanpirom, Tharakorn Maneerat, Rawiwan Charoensup, Thapakorn Tree-Udom, Punyawatt Pintathong, Surat Laphookhieo and Tawanun Sripisut

Molecules 2022, 27(14), 4401; https://doi.org/10.3390/molecules27144401 - 08 Jul 2022

Cited by 8 | Viewed by 4416

Abstract

Kaempferia parviflora (Black ginger) is used widely in medical fields as an anti-microorganism and anti-inflammation. In this study, the aim was to evaluate the in vitro and in vivo anti-acne efficacy of black ginger extract. The results indicate that the methanol and ethanol [...] Read more.

Kaempferia parviflora (Black ginger) is used widely in medical fields as an anti-microorganism and anti-inflammation. In this study, the aim was to evaluate the in vitro and in vivo anti-acne efficacy of black ginger extract. The results indicate that the methanol and ethanol extracts showed the highest total phenolic contents, without a significant difference, whereas the n-hexane extract showed the highest total flavonoid content. Nine flavones were detected using UPLC−QTOF−MS, and the ethyl acetate extract showed the highest amount of 5,7-dimethoxyflavone (DMF) according to HPLC. Antibacterial activity against Staphylococcus aureus, S. epidermidis, and Cutibacterium acnes was observed. All the extracts showed antimicrobial activity against C. acnes, revealing MICs in the range of 0.015 to 0.030 mg/mL, whereas the ethyl acetate extract inhibited the growth of S. epidermidis with a MIC of 3.84 mg/mL. In addition, the ethyl acetate extract showed the highest activity regarding nitric oxide inhibition (IC50 = 12.59 ± 0.35 µg/mL). The ethyl acetate extract was shown to be safe regarding cell viability at 0.1 mg/mL. The anti-acne efficacy was evaluated on volunteers. The volunteers were treated in two groups: one administered a 0.02% ethyl acetate extract gel-cream (n = 9) and one administered a placebo (n = 9) for 6 weeks. The group treated with the gel-cream containing the extract showed 36.52 and 52.20% decreases in acne severity index (ASI) after 4 and 6 weeks, respectively, and 18.19 and 18.54% decreases in erythema, respectively. The results suggest that K. parviflora could be a potent active ingredient in anti-inflammatory and anti-acne products. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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15 pages, 2961 KiB  

Open AccessArticle

Curcumol Synergizes with Cisplatin in Osteosarcoma by Inhibiting M2-like Polarization of Tumor-Associated Macrophages

by Jincheng Wang, Jialu Jin, Ting Chen and Qian Zhou

Molecules 2022, 27(14), 4345; https://doi.org/10.3390/molecules27144345 - 06 Jul 2022

Cited by 7 | Viewed by 2060

Abstract

Osteosarcoma is the most prevalent bone cancer, and chemotherapy is still an indispensable treatment in its clinical practice. Cisplatin (CDDP) has become the most commonly used agent for osteosarcoma, although the outcomes of CDDP chemotherapy remain unsatisfactory because of frequent resistance. Here, we [...] Read more.

Osteosarcoma is the most prevalent bone cancer, and chemotherapy is still an indispensable treatment in its clinical practice. Cisplatin (CDDP) has become the most commonly used agent for osteosarcoma, although the outcomes of CDDP chemotherapy remain unsatisfactory because of frequent resistance. Here, we report on a promising combination therapy where curcumol, a bioactive sesquiterpenoid, enhanced CDDP-induced apoptosis to eradicate osteosarcoma cells, and revealed that M2-like macrophages might be the underlying associated mechanisms. First, we observed that curcumol enhanced the CDDP-mediated inhibition of cell proliferation and augmented the apoptosis in osteosarcoma cell lines. Curcumol contributed to preventing the migration of osteosarcoma cells when combined with CDDP. Moreover, this drug combination showed more potent tumor-growth suppression in the orthotopic transplantation of osteosarcoma K7M2 WT cells. We then estimated chemotherapy-associated drug-resistant genes, including ABCB1, ABCC1 and ABCG2, and found that curcumol significantly reversed the mRNA levels of CDDP-induced ABCB1, ABCC1 and ABCG2 genes in the tumor tissue. Moreover, M2-like macrophages were enriched in osteosarcoma tissues, and were largely decreased after curcumol and CDDP treatment. Taken together, these findings suggest that curcumol inhibits the polarization of M2-like macrophages and could be a promising combination strategy to synergize with CDDP in the osteosarcoma. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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20 pages, 4203 KiB  

Open AccessArticle

Antibacterial Activity and Components of the Methanol-Phase Extract from Rhizomes of Pharmacophagous Plant Alpinia officinarum Hance

by Junfeng Fu, Yaping Wang, Meng Sun, Yingwei Xu and Lanming Chen

Molecules 2022, 27(13), 4308; https://doi.org/10.3390/molecules27134308 - 05 Jul 2022

Cited by 7 | Viewed by 2064

Abstract

The rhizomes of Alpinia officinarum Hance (known as the smaller galangal) have been used as a traditional medicine for over 1000 years. Nevertheless, little research is available on the bacteriostatic activity of the herb rhizomes. In this study, we employed, for the first [...] Read more.

The rhizomes of Alpinia officinarum Hance (known as the smaller galangal) have been used as a traditional medicine for over 1000 years. Nevertheless, little research is available on the bacteriostatic activity of the herb rhizomes. In this study, we employed, for the first time, a chloroform and methanol extraction method to investigate the antibacterial activity and components of the rhizomes of A. officinarum Hance. The results showed that the growth of five species of pathogenic bacteria was significantly inhibited by the galangal methanol-phase extract (GMPE) (p < 0.05). The GMPE treatment changed the bacterial cell surface hydrophobicity, membrane fluidity and/or permeability. Comparative transcriptomic analyses revealed approximately eleven and ten significantly altered metabolic pathways in representative Gram-positive Staphylococcus aureus and Gram-negative Enterobacter sakazakii pathogens, respectively (p < 0.05), demonstrating different antibacterial action modes. The GMPE was separated further using a preparative high-performance liquid chromatography (Prep-HPLC) technique, and approximately 46 and 45 different compounds in two major component fractions (Fractions 1 and 4, respectively) were identified using ultra-HPLC combined with mass spectrometry (UHPLC-MS) techniques. o-Methoxy cinnamaldehyde (40.12%) and p-octopamine (62.64%) were the most abundant compounds in Fractions 1 and 4, respectively. The results of this study provide data for developing natural products from galangal rhizomes against common pathogenic bacteria. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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12 pages, 1890 KiB  

Open AccessArticle

β-Carotene from the Alga Dunaliella bardawil Decreases Gene Expression of Adipose Tissue Macrophage Recruitment Markers and Plasma Lipid Concentrations in Mice Fed a High-Fat Diet

by Nir Melnikov, Yehuda Kamari, Michal Kandel-Kfir, Iris Barshack, Ami Ben-Amotz, Dror Harats, Aviv Shaish and Ayelet Harari

Mar. Drugs 2022, 20(7), 433; https://doi.org/10.3390/md20070433 - 29 Jun 2022

Cited by 4 | Viewed by 1907

Abstract

Vitamin A and provitamin A carotenoids are involved in the regulation of adipose tissue metabolism and inflammation. We examined the effect of dietary supplementation using all-trans and 9-cis β-carotene-rich Dunaliella bardawil alga as the sole source of vitamin A on obesity-associated comorbidities and [...] Read more.

Vitamin A and provitamin A carotenoids are involved in the regulation of adipose tissue metabolism and inflammation. We examined the effect of dietary supplementation using all-trans and 9-cis β-carotene-rich Dunaliella bardawil alga as the sole source of vitamin A on obesity-associated comorbidities and adipose tissue dysfunction in a diet-induced obesity mouse model. Three-week-old male mice (C57BL/6) were randomly allocated into two groups and fed a high-fat, vitamin A-deficient diet supplemented with either vitamin A (HFD) or β-carotene (BC) (HFD-BC). Vitamin A levels in the liver, WATs, and BAT of the HFD-BC group were 1.5–2.4-fold higher than of the HFD group. BC concentrations were 5–6-fold greater in BAT compared to WAT in the HFD-BC group. The eWAT mRNA levels of the Mcp-1 and Cd68 were 1.6- and 2.1-fold lower, respectively, and the plasma cholesterol and triglyceride concentrations were 30% and 28% lower in the HFD-BC group compared with the HFD group. Dietary BC can be the exclusive vitamin A source in mice fed a high-fat diet, as shown by the vitamin A concentration in the plasma and tissues. Feeding BC rather than vitamin A reduces adipose tissue macrophage recruitment markers and plasma lipid concentrations. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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23 pages, 2144 KiB  

Open AccessReview

Green Tea (Camellia sinensis): A Review of Its Phytochemistry, Pharmacology, and Toxicology

by Tiantian Zhao, Chao Li, Shuai Wang and Xinqiang Song

Molecules 2022, 27(12), 3909; https://doi.org/10.3390/molecules27123909 - 18 Jun 2022

Cited by 53 | Viewed by 12318

Abstract

Objectives Green tea (Camellia sinensis) is a kind of unfermented tea that retains the natural substance in fresh leaves to a great extent. It is regarded as the second most popular drink in the world besides water. In this paper, the [...] Read more.

Objectives Green tea (Camellia sinensis) is a kind of unfermented tea that retains the natural substance in fresh leaves to a great extent. It is regarded as the second most popular drink in the world besides water. In this paper, the phytochemistry, pharmacology, and toxicology of green tea are reviewed systematically and comprehensively. Key findings Green tea has been demonstrated to be good for human health. Nowadays, multiple pharmacologically active components have been isolated and identified from green tea, including tea polyphenols, alkaloids, amino acids, polysaccharides, and volatile components. Recent studies have demonstrated that green tea shows versatile pharmacological activities, such as antioxidant, anticancer, hypoglycemic, antibacterial, antiviral, and neuroprotective. Studies on the toxic effects of green tea extract and its main ingredients have also raised concerns including hepatotoxicity and DNA damage. Summary Green tea can be used to assist the treatment of diabetes, Alzheimer’s disease, oral cancer, and dermatitis. Consequently, green tea has shown promising practical prospects in health care and disease prevention. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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10 pages, 1325 KiB  

Open AccessArticle

New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate

by Olusola Bodede, Garland K. More, Roshila Moodley, Paul Steenkamp, Himansu Baijnath, Vinesh Maharaj and Gerhard Prinsloo

Molecules 2022, 27(12), 3839; https://doi.org/10.3390/molecules27123839 - 15 Jun 2022

Viewed by 1432

Abstract

This work presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate. A known cardanol, 3-heptadec-12′-Z-enyl phenol (1) and three new alk(en)ylhydroxycyclohexanes, namely, (1R,3R)-1,3-dihydroxy-3-[heptadec-12′(Z)-enyl]cyclohexane (2) (1S [...] Read more.

This work presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate. A known cardanol, 3-heptadec-12′-Z-enyl phenol (1) and three new alk(en)ylhydroxycyclohexanes, namely, (1R,3R)-1,3-dihydroxy-3-[heptadec-12′(Z)-enyl]cyclohexane (2) (1S,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxy-5-[octadec-13′(Z)-enyl]cyclohexane (3) and (1R,2S,4R)-1,2,4-trihydroxy-4-[heptadec-12′(Z)-enyl]cyclohexane (4) were isolated from the gum. The structures of the compounds were determined by extensive 1D and 2D NMR spectroscopy and HR-ESI-MS data. The ethanolic extract of the gum was found to be the most potent tyrosinase inhibitor with IC₅₀ of 11.32 µg/mL while compounds 2 and 3, with IC₅₀ values of 24.90 and 26.99 µg/mL, respectively, were found to be potential anti-tyrosinase candidates from the gum. Gum exudate may be a potential source for non-destructive harvesting of selective pharmacologically active compounds from plants. The results also provide evidence that H. caffrum gum may find application in cosmetics as a potential anti-tyrosinase agent. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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19 pages, 2848 KiB  

Open AccessArticle

Potential Use of Tea Tree Oil as a Disinfectant Agent against Coronaviruses: A Combined Experimental and Simulation Study

by Alice Romeo, Federico Iacovelli, Carolina Scagnolari, Mirko Scordio, Federica Frasca, Roberta Condò, Serena Ammendola, Roberta Gaziano, Maurizio Anselmi, Maurizio Divizia and Mattia Falconi

Molecules 2022, 27(12), 3786; https://doi.org/10.3390/molecules27123786 - 12 Jun 2022

Cited by 13 | Viewed by 3837

Abstract

The COVID-19 pandemic has highlighted the relevance of proper disinfection procedures and renewed interest in developing novel disinfectant materials as a preventive strategy to limit SARS-CoV-2 contamination. Given its widely known antibacterial, antifungal, and antiviral properties, Melaleuca alternifolia essential oil, also named Tea [...] Read more.

The COVID-19 pandemic has highlighted the relevance of proper disinfection procedures and renewed interest in developing novel disinfectant materials as a preventive strategy to limit SARS-CoV-2 contamination. Given its widely known antibacterial, antifungal, and antiviral properties, Melaleuca alternifolia essential oil, also named Tea tree oil (TTO), is recognized as a potential effective and safe natural disinfectant agent. In particular, the proposed antiviral activity of TTO involves the inhibition of viral entry and fusion, interfering with the structural dynamics of the membrane and with the protein envelope components. In this study, for the first time, we demonstrated the virucidal effects of TTO against the feline coronavirus (FCoVII) and the human coronavirus OC43 (HCoV-OC43), both used as surrogate models for SARS-CoV-2. Then, to atomistically uncover the possible effects exerted by TTO compounds on the outer surface of the SARS-CoV-2 virion, we performed Gaussian accelerated Molecular Dynamics simulations of a SARS-CoV-2 envelope portion, including a complete model of the Spike glycoprotein in the absence or presence of the three main TTO compounds (terpinen-4-ol, γ-terpinene, and 1,8-cineole). The obtained results allowed us to hypothesize the mechanism of action of TTO and its possible use as an anti-coronavirus disinfectant agent. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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10 pages, 1185 KiB  

Open AccessArticle

Preclinical Pharmacokinetics and Bioavailability of Oxypeucedanin in Rats after Single Intravenous and Oral Administration

by Ming-Cong Zheng, Wen-Ting Tang, Lu-Lu Yu, Xun-Jia Qian, Jie Ren, Jie-Jia Li, Wei-Wei Rong, Jun-Xu Li and Qing Zhu

Molecules 2022, 27(11), 3570; https://doi.org/10.3390/molecules27113570 - 02 Jun 2022

Cited by 4 | Viewed by 1971

Abstract

Oxypeucedanin, a furanocoumarin extracted from many traditional Chinese herbal medicines, has a variety of pharmacological effects. However, the independent pharmacokinetic characteristics and bioavailability of this compound remains elusive. In this study, a rapid, sensitive, and selective method using ultra-high performance liquid chromatography–tandem mass [...] Read more.

Oxypeucedanin, a furanocoumarin extracted from many traditional Chinese herbal medicines, has a variety of pharmacological effects. However, the independent pharmacokinetic characteristics and bioavailability of this compound remains elusive. In this study, a rapid, sensitive, and selective method using ultra-high performance liquid chromatography–tandem mass spectrometry (UPLC/MS/MS) was developed for evaluating the intravenous and oral pharmacokinetics of oxypeucedanin. After intravenous administration of oxypeucedanin (2.5, 5, and 10 mg/kg), and intragastric administration of oxypeucedanin (20 mg/kg), blood samples were collected periodically from the tail vein. The plasma concentration-time curves were plotted, and the pharmacokinetic parameters were calculated using a non-compartmental model analysis. After intravenous administration of oxypeucedanin (single dosing at 2.5, 5, and 10 mg/kg) to rats, the pharmacokinetics fit the linear kinetics characteristics, which showed that some parameters including average elimination half-life (T_1/2Z of 0.61~0.66 h), mean residence time (MRT of 0.62~0.80 h), apparent volume of distribution (V_Z of 4.98~7.50 L/kg), and systemic clearance (CL_Z of 5.64~8.55 L/kg/h) are dose-independent and the area under concentration-time curve (AUC) increased in a dose-proportional manner. Single oral administration of oxypeucedanin (20 mg/kg) showed poor and slow absorption with the mean time to reach the peak concentration (T_max) of 3.38 h, MRT of 5.86 h, T_1/2Z of 2.94 h, and a mean absolute bioavailability of 10.26% in rats. These results provide critical information for a better understanding of the pharmacological effect of oxypeucedanin, which will facilitate its research and development. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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15 pages, 1439 KiB  

Open AccessArticle

Biotization of Endophytes Trichoderma asperellum and Bacillus subtilis in Mentha spicata Microplants to Promote Growth, Pathogen Tolerance and Specialized Plant Metabolites

by Dagoberto Castro-Restrepo, Maria Isabel Dominguez, Bertha Gaviria-Gutiérrez, Edison Osorio and Karina Sierra

Plants 2022, 11(11), 1474; https://doi.org/10.3390/plants11111474 - 31 May 2022

Cited by 5 | Viewed by 2212

Abstract

In the present study, the effect of biotization of Mentha spicata microplants with Trichoderma asperellum and Bacillus subtilis on growth, Rhizoctonia sp., incidence, and specialized metabolites content was evaluated. Analyses of root tissues of the microplants showed 100% endophytism with both microorganisms. During [...] Read more.

In the present study, the effect of biotization of Mentha spicata microplants with Trichoderma asperellum and Bacillus subtilis on growth, Rhizoctonia sp., incidence, and specialized metabolites content was evaluated. Analyses of root tissues of the microplants showed 100% endophytism with both microorganisms. During the acclimatization phase, plants with the endophytes T. asperellum and B. subtilis had a survival rate of 95% and 93%, respectively, compared to 75% for control plants. Then, under greenhouse conditions, a trial was carried out with biotized plants with or without Rhizoctonia sp. inoculation, plants inoculated with Rhizoctonia sp., and endophyte- and pathogen-free control. Biotized plants with the endophytes showed higher dry biomass and the incidence of Rhizoctonia was lower (8% for T. asperellum and 10% for B. subtilis) compared to plants inoculated with the pathogen (82%). In addition, plants with T. asperellum had the highest contents of total polyphenols (280 GAE/100 mg sample) and rosmarinic acid (28 mg RA/100 g sample). Thus, this study shows the potential of the technique of using the endophytes T. asperellum and B. subtilis on M. spicata microplants to improve plant survival and growth, decrease the incidence of Rhizoctonia sp., and improve the contents of specialized metabolites, which can contribute to the sustainable management of this crop. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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28 pages, 1017 KiB  

Open AccessReview

Fucoxanthin Is a Potential Therapeutic Agent for the Treatment of Breast Cancer

by Tsz-Ying Lau and Hiu-Yee Kwan

Mar. Drugs 2022, 20(6), 370; https://doi.org/10.3390/md20060370 - 30 May 2022

Cited by 13 | Viewed by 3683

Abstract

Breast cancer (BC) is one of the most common cancers diagnosed and the leading cause of cancer-related death in women. Although there are first-line treatments for BC, drug resistances and adverse events have been reported. Given the incidence of BC keeps increasing, seeking [...] Read more.

Breast cancer (BC) is one of the most common cancers diagnosed and the leading cause of cancer-related death in women. Although there are first-line treatments for BC, drug resistances and adverse events have been reported. Given the incidence of BC keeps increasing, seeking novel therapeutics is urgently needed. Fucoxanthin (Fx) is a dietary carotenoid commonly found in seaweeds and diatoms. Both in vitro and in vivo studies show that Fx and its deacetylated metabolite fucoxanthinol (Fxol) inhibit and prevent BC growth. The NF-κB signaling pathway is considered the major pathway contributing to the anti-proliferation, anti-angiogenesis and pro-apoptotic effects of Fx and Fxol. Other signaling molecules such as MAPK, MMP2/9, CYP and ROS are also involved in the anti-cancer effects by regulating the tumor microenvironment, cancer metastasis, carcinogen metabolism and oxidation. Besides, Fx also possesses anti-obesity effects by regulating UCP1 levels and lipid metabolism, which may help to reduce BC risk. More importantly, mounting evidence demonstrates that Fx overcomes drug resistance. This review aims to give an updated summary of the anti-cancer effects of Fx and summarize the underlying mechanisms of action, which will provide novel strategies for the development of Fx as an anti-cancer therapeutic agent. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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17 pages, 2676 KiB  

Open AccessArticle

Phytochemicals Profiling, Antimicrobial Activity and Mechanism of Action of Essential Oil Extracted from Ginger (Zingiber officinale Roscoe cv. Bentong) against Burkholderia glumae Causative Agent of Bacterial Panicle Blight Disease of Rice

by Mahesh Tiran Gunasena, Amara Rafi, Syazwan Afif Mohd Zobir, Mohd Zobir Hussein, Asgar Ali, Abdulaziz Bashir Kutawa, Mohd Aswad Abdul Wahab, Mohd Roslan Sulaiman, Fariz Adzmi and Khairulmazmi Ahmad

Plants 2022, 11(11), 1466; https://doi.org/10.3390/plants11111466 - 30 May 2022

Cited by 14 | Viewed by 3038

Abstract

Essential oils protect plants, and due to their natural origin, there is much interest in using them as antimicrobial agents. The purpose of this study was to determine the phytochemical constituents of ginger essential oil (GEO), antimicrobial activity, and mode of action against [...] Read more.

Essential oils protect plants, and due to their natural origin, there is much interest in using them as antimicrobial agents. The purpose of this study was to determine the phytochemical constituents of ginger essential oil (GEO), antimicrobial activity, and mode of action against Burkholderia glumae (Bg). In addition, the volatile active compounds (AIs) were studied using GC-MS, FTIR, and Raman spectroscopy. A total of 45 phytochemical components were detected and the most prevalent bioactive compounds were Geranial, 1,8-Cineole, Neral, Camphene, α-Zingiberene, and α-Farnesene. Furthermore, it was found that the most dominant terpenes in GEO were monoterpenes. The diameter zone of inhibition values varied from 7.1 to 15 mm depending on the concentration tested. In addition, the MIC and MBC values were 112.5 µL/mL. Faster killing time and lower membrane potential were observed in 1xMIC treatment compared to 0.5xMIC treatment, whereas the control had the maximum values. From observations of various images, it was concluded that the mode of action of GEO affected the cytoplasmic membrane, causing it to lose its integrity and increase its permeability. Therefore, the antibacterial study and mechanism of action revealed that GEO is very effective in suppressing the growth of B. glumae. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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9 pages, 1629 KiB  

Open AccessArticle

Antiviral Activities of Officinaloside C against Herpes Simplex Virus-1

by Ji Xiao, Miaomiao Cai, Yifei Wang and Ping Ding

Molecules 2022, 27(11), 3365; https://doi.org/10.3390/molecules27113365 - 24 May 2022

Cited by 1 | Viewed by 1642

Abstract

The iridoid compounds in traditional Chinese medicine play a prominent role in their antiviral effects. We previously reported the anti-inflammatory effect of new iridoids from the aerial parts of Morinda officinalis. Nevertheless, several open questions remain to explore the other biological functions [...] Read more.

The iridoid compounds in traditional Chinese medicine play a prominent role in their antiviral effects. We previously reported the anti-inflammatory effect of new iridoids from the aerial parts of Morinda officinalis. Nevertheless, several open questions remain to explore the other biological functions of these new iridoid compounds. Herpes simplex virus-1 (HSV-1) is one of the most prevalent pathogens in human beings worldwide and due to limited therapies, mainly with the guanosine analog aciclovir (ACV) and other analogs, the search for new drugs with different modes of action and low toxicity becomes particularly urgent for public health. This study aimed to explore the anti-HSV-1 effects of iridoids from the aerial parts of Morinda officinalis. The dried aerial parts of Morinda officinalis were extracted with 95% ethanol and systematic separation and purification were then carried out by modern column chromatography methods such as silica gel column, RP-ODS column, Sephadex LH-20 gel column, and semi-preparative liquid phase, and the structure of these compounds were identified through the physical and chemical properties and a variety of spectral techniques. The obtained seven new iridoid compounds were screened for antiviral activity on HSV-1 through CCK8 and the cytopathic effect, and then the plaque reduction assay, the anti-fluorescence reporter virus strain replication, and RT-qPCR experiments were carried out to further evaluate the antiviral effect. Seven new iridoid compounds (officinaloside A–G) were identified from the aerial parts of Morinda officinalis, and officinaloside C showed anti-HSV-1 activity. Further functional experiments confirmed that officinaloside C has a significant inhibiting effect on HSV-1 virus plaque formation, viral gene, and protein expression, and fluorescent virus replication. Our findings suggest that officinaloside C has significant inhibitory effects on viral plaque formation, genome replication, and viral protein expression of HSV-1 which implies that officinaloside C exhibits viral activity and may be a promising treatment for HSV-1 infection. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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10 pages, 1438 KiB  

Open AccessArticle

Production of Prosaikogenin F, Prosaikogenin G, Saikogenin F and Saikogenin G by the Recombinant Enzymatic Hydrolysis of Saikosaponin and their Anti-Cancer Effect

by Ji-Eun Lee, Bong-Kyu Song, Ju-Hyeon Kim, Muhammad-Zubair Siddiqi and Wan-Taek Im

Molecules 2022, 27(10), 3255; https://doi.org/10.3390/molecules27103255 - 19 May 2022

Cited by 5 | Viewed by 1712

Abstract

The saponins of Bupleurum falcatum L., saikosaponins, are the major components responsible for its pharmacological and biological activities. However, the anti-cancer effects of prosaikogenin and saikogenin, which are glycoside hydrolyzed saikosaponins, are still unknown due to its rarity in plants. In this study, [...] Read more.

The saponins of Bupleurum falcatum L., saikosaponins, are the major components responsible for its pharmacological and biological activities. However, the anti-cancer effects of prosaikogenin and saikogenin, which are glycoside hydrolyzed saikosaponins, are still unknown due to its rarity in plants. In this study, we applied two recombinant glycoside hydrolases that exhibit glycoside cleavage activity with saikosaponins. The two enzymes, BglPm and BglLk, were cloned from Paenibacillus mucilaginosus and Lactobacillus koreensis, and exhibited good activity between 30–37 °C and pH 6.5–7.0. Saikosaponin A and D were purified and obtained from the crude B. falcatum L. extract using preparative high performance liquid chromatography technique. Saikosaponin A and D were converted into saikogenin F via prosaikogenin F, and saikogenin G via prosaikogenin G using enzyme transformation with high β-glycosidase activity. The two saikogenin and two prosaikogenin compounds were purified using a silica column to obtain 78.1, 62.4, 8.3, and 7.5 mg of prosaikogenin F, prosaikogenin G, saikogenin F, and saikogenin G, respectively, each with 98% purity. The anti-cancer effect of the six highly purified saikosaponins was investigated in the human colon cancer cell line HCT 116. The results suggested that saikosaponins and prosaikogenins markedly inhibit the growth of the cancer cell line. Thus, this enzymatic technology could significantly improve the production of saponin metabolites of B. falcatum L. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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9 pages, 248 KiB  

Open AccessArticle

Microarray Analysis of the Genomic Effect of Eugenol on Methicillin-Resistant Staphylococcus aureus

by Ayuba Sunday Buru, Vasantha Kumari Neela, Kavitha Mohandas and Mallikarjuna Rao Pichika

Molecules 2022, 27(10), 3249; https://doi.org/10.3390/molecules27103249 - 19 May 2022

Cited by 7 | Viewed by 1795

Abstract

Staphylococcus aureus is a highly adaptive human pathogen responsible for serious hospital- and community-acquired infectious diseases, ranging from skin and soft tissue infections, to complicated and life-threatening conditions such as endocarditis and toxic shock syndrome (TSS). The rapid development of resistance of this [...] Read more.

Staphylococcus aureus is a highly adaptive human pathogen responsible for serious hospital- and community-acquired infectious diseases, ranging from skin and soft tissue infections, to complicated and life-threatening conditions such as endocarditis and toxic shock syndrome (TSS). The rapid development of resistance of this organism to available antibiotics over the last few decades has necessitated a constant search for more efficacious antibacterial agents. Eugenol (4-allyl-2-methoxyphenol) belongs to the class of chemical compounds called phenylpropanoids. It is a pure-to-pale yellow, oily liquid substance, mostly extracted as an essential oil from natural products such as clove, cinnamon, nutmeg, basil, and bay leaf. Eugenol has previously been shown to have antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA). However, the mechanism of action of eugenol against MRSA has not, as yet, been elucidated; hence, the necessity of this study. Global gene expression patterns in response to challenge from subinhibitory concentrations of eugenol were analysed using the Agilent DNA microarray system to identify genes that can be used as drug targets—most importantly, essential genes involved in unique metabolic pathways elicited for bacterial survival. Transcriptomic analysis of fluctuating genes revealed those involved in amino acid metabolism, fatty acid metabolism, translational, and ribosomal pathways. In amino acid metabolism, for instance, the argC gene encodes for N-acetyl-gamma-glutamyl-phosphate reductase. The argC gene plays an important role in the biosynthesis of arginine from glutamate in the amino acid metabolic pathway. It is the enzyme that catalyses the third step in the latter reaction, and without this process the production of N-acetylglutamate 5-semialdehyde cannot be completed from the NADP-dependent reduction of N-acetyl-5-glutamyl phosphate, which is essential for the survival of some microorganisms and plants. This study enables us to examine complete global transcriptomic responses in MRSA when challenged with eugenol. It reveals novel information with the potential to further benefit the exploratory quest for novel targets against this pathogen, with a view to the development of efficacious antimicrobial agents for the treatment of associated infections. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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17 pages, 4420 KiB  

Open AccessArticle

(−)-Lariciresinol Isolated from the Roots of Isatis indigotica Fortune ex Lindl. Inhibits Hepatitis B Virus by Regulating Viral Transcription

by Lu Yang, Huiqiang Wang, Haiyan Yan, Kun Wang, Shuo Wu and Yuhuan Li

Molecules 2022, 27(10), 3223; https://doi.org/10.3390/molecules27103223 - 18 May 2022

Cited by 6 | Viewed by 1862

Abstract

Chronic hepatitis induced by hepatitis B virus (HBV) infection is a serious public health problem, leading to hepatic cirrhosis and liver cancer. Although the currently approved medications can reliably decrease the virus load and prevent the development of hepatic diseases, they fail to [...] Read more.

Chronic hepatitis induced by hepatitis B virus (HBV) infection is a serious public health problem, leading to hepatic cirrhosis and liver cancer. Although the currently approved medications can reliably decrease the virus load and prevent the development of hepatic diseases, they fail to induce durable off-drug control of HBV replication in the majority of patients. The roots of Isatis indigotica Fortune ex Lindl., a traditional Chinese medicine, were frequently used for the prevention of viral disease in China. In the present study, (−)-lariciresinol ((−)-LRSL), isolated from the roots of Isatis indigotica Fortune ex Lindl., was found to inhibit HBV DNA replication of both wild-type and nucleos(t)ide analogues (NUCs)-resistant strains in vitro. Mechanism studies revealed that (−)-LRSL could block RNA production after treatment, followed by viral proteins, and then viral particles and DNA. Promoter reporter assays and RNA decaying dynamic experiments indicated that (−)-LRSL mediated HBV RNA reduction was mainly due to transcriptional inhibition rather than degradation. Moreover, (−)-LRSL in a dose-dependent manner also inhibited other animal hepadnaviruses, including woodchuck hepatitis virus (WHV) and duck hepatitis B virus (DHBV). Combining the analysis of RNA-seq, we further found that the decrease in HBV transcriptional activity by (−)-LRSL may be related to hepatocyte nuclear factor 1α (HNF1α). Taken together, (−)-LRSL represents a novel chemical entity that inhibits HBV replication by regulating HNF1α mediated HBV transcription, which may provide a new perspective for HBV therapeutics. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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10 pages, 797 KiB  

Open AccessArticle

Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities

by Pei-Song Yang, Jia-Meng Dai, Xue-Jiao Gu, Wen Xiong, De-Quan Huang, Shi-Yu Qiu, Jun-Na Zheng, Yong Li, Feng-Xian Yang and Min Zhou

Molecules 2022, 27(10), 3129; https://doi.org/10.3390/molecules27103129 - 13 May 2022

Cited by 11 | Viewed by 1941

Abstract

The Cassia (Leguminosae) genus has attracted a lot of attention as a prolific source of alkaloids and chromones with diverse structures and biological properties. The aim of this study is to screen the antiviral compounds from Cassia alata. The extract of the [...] Read more.

The Cassia (Leguminosae) genus has attracted a lot of attention as a prolific source of alkaloids and chromones with diverse structures and biological properties. The aim of this study is to screen the antiviral compounds from Cassia alata. The extract of the stem bark of this plant was separated using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. As a result, three new indole alkaloids, alataindoleins A–C (1–3); one new chromone, alatachromone A (4); and a new dimeric chromone-indole alkaloid, alataindolein D (5) were isolated. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Interestingly, alataindolein D (5) represents a new type of dimeric alkaloid with an unusual N-2−C-16’ linkage, which is biogenetically derived from a chromone and an indole alkaloid via an intermolecular nucleophilic substitution reaction. Compounds 1–5 were tested for their anti-tobacco mosaic virus (TMV) and anti-rotavirus activities, and the results showed that compounds 2–4 showed high anti-TMV activities with inhibition rates of 44.4%, 66.5%, and 52.3%, respectively. These rates were higher than those of the positive control (with inhibition rate of 32.8%). Compounds 1 and 5 also showed potential anti-TMV activities with inhibition rates of 26.5% and 31.8%, respectively. In addition, compounds 1–5 exhibited potential anti-rotavirus activities with therapeutic index (TI) values in the range of 9.75~15.3. The successful isolation and structure identification of the above new compounds provided materials for the screening of antivirus drugs, and contributed to the development and utilization of C. alata. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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12 pages, 1019 KiB  

Open AccessArticle

Total Phenolics and Anthocyanins Contents and Antioxidant Activity in Four Different Aerial Parts of Leafy Sweet Potato (Ipomoea batatas L.)

by Ruixue Jia, Chaochen Tang, Jingyi Chen, Xiongjian Zhang and Zhangying Wang

Molecules 2022, 27(10), 3117; https://doi.org/10.3390/molecules27103117 - 12 May 2022

Cited by 8 | Viewed by 2182

Abstract

Leafy sweet potato (Ipomoea batatas L.) is an excellent source of nutritious greens and natural antioxidants, but reports on antioxidants content and activity at buds, leaves, petioles, and stems are scarce. Therefore, the total phenolics content (TPC), total anthocyanins content (TAC), and [...] Read more.

Leafy sweet potato (Ipomoea batatas L.) is an excellent source of nutritious greens and natural antioxidants, but reports on antioxidants content and activity at buds, leaves, petioles, and stems are scarce. Therefore, the total phenolics content (TPC), total anthocyanins content (TAC), and antioxidant activity (assessed by DPPH and ABTS radical scavenging activities and ferric reducing antioxidant power (FRAP)) were investigated in four aerial parts of 11 leafy sweet potato varieties. The results showed that varieties with pure green aerial parts, independently of the part analyzed, had higher TPC, FRAP, and ABTS radical scavenging activities. The green-purple varieties had a significantly higher TAC, while variety GS-17-22 had the highest TAC in apical buds and leaves, and variety Ziyang in petioles and stems. Among all parts, apical buds presented the highest TPC and antioxidant capacity, followed by leaves, petioles, and stems, while the highest TAC level was detected in leaves. The TPC was positively correlated with ABTS radical scavenging activity and FRAP in all parts studied, whereas the TAC was negatively correlated with DPPH radical scavenging activity. Collectively, the apical buds and leaves of sweet potato had the higher levels of nutritional values. These results would provide reference values for further breeding of leafy sweet potatoes. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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12 pages, 1844 KiB  

Open AccessArticle

Biotransformation of Liquiritigenin into Characteristic Metabolites by the Gut Microbiota

by Adili Keranmu, Li-Bin Pan, Jie Fu, Pei Han, Hang Yu, Zheng-Wei Zhang, Hui Xu, Xin-Yu Yang, Jia-Chun Hu, Hao-Jian Zhang, Meng-Meng Bu, Jian-Dong Jiang, Nian-Zeng Xing and Yan Wang

Molecules 2022, 27(10), 3057; https://doi.org/10.3390/molecules27103057 - 10 May 2022

Cited by 7 | Viewed by 2325

Abstract

The bioavailability of flavonoids is generally low after oral administration. The metabolic transformation of flavonoids by the gut microbiota may be one of the main reasons for this, although these metabolites have potential pharmacological activities. Liquiritigenin is an important dihydroflavonoid compound found in [...] Read more.

The bioavailability of flavonoids is generally low after oral administration. The metabolic transformation of flavonoids by the gut microbiota may be one of the main reasons for this, although these metabolites have potential pharmacological activities. Liquiritigenin is an important dihydroflavonoid compound found in Glycyrrhiza uralensis that has a wide range of pharmacological properties, such as antitumor, antiulcer, anti-inflammatory, and anti-AIDS effects, but its mechanism of action remains unclear. This study explored the metabolites of liquiritigenin by examining gut microbiota metabolism and hepatic metabolism in vitro. Using LC-MS/MS and LC/MSⁿ-IT-TOF techniques, three possible metabolites of liquiritigenin metabolized by the gut microbiota were identified: phloretic acid (M3), resorcinol (M4), and M5. M5 is speculated to be davidigenin, which has antitumor activity. By comparing these two metabolic pathways of liquiritigenin (the gut microbiota and liver microsomes), this study revealed that there are three main metabolites of liquiritigenin generated by intestinal bacteria, which provides a theoretical basis for the study of pharmacologically active substances in vivo. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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15 pages, 2787 KiB  

Open AccessArticle

Comparative Metabolomic Analysis of Four Fabaceae and Relationship to In Vitro Nematicidal Activity against Xiphinema index

by Lise Negrel, Raymonde Baltenweck, Gerard Demangeat, Françoise Le Bohec-Dorner, Camille Rustenholz, Amandine Velt, Claude Gertz, Eva Bieler, Markus Dürrenberger, Pascale Gombault, Philippe Hugueney and Olivier Lemaire

Molecules 2022, 27(10), 3052; https://doi.org/10.3390/molecules27103052 - 10 May 2022

Cited by 1 | Viewed by 1941

Abstract

The grapevine fanleaf virus (GFLV), responsible for fanleaf degeneration, is spread in vineyards by the soil nematode Xiphinema index. Nematicide molecules were used to limit the spread of the disease until they were banned due to negative environmental impacts. Therefore, there is [...] Read more.

The grapevine fanleaf virus (GFLV), responsible for fanleaf degeneration, is spread in vineyards by the soil nematode Xiphinema index. Nematicide molecules were used to limit the spread of the disease until they were banned due to negative environmental impacts. Therefore, there is a growing interest in alternative methods, including plant-derived products with antagonistic effects to X. index. In this work, we evaluated the nematicidal potential of the aerial parts and roots of four Fabaceae: sainfoin (Onobrychis viciifolia), birdsfoot trefoil (Lotus corniculatus), sweet clover (Melilotus albus), and red clover (Trifolium pratense), as well as that of sainfoin-based commercial pellets. For all tested plants, either aerial or root parts, or both of them, exhibited a nematicidal effect on X. index in vitro, pellets being as effective as freshly harvested plants. Comparative metabolomic analyses did not reveal molecules or molecule families specifically associated with antagonistic properties toward X. index, suggesting that the nematicidal effect is the result of a combination of different molecules rather than associated with a single compound. Finally, scanning electron microscope observations did not reveal the visible impact of O. viciifolia extract on X. index cuticle, suggesting that alteration of the cuticle may not be the primary cause of their nematicidal effect. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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21 pages, 10738 KiB  

Open AccessArticle

Biocomputational Assessment of Natural Compounds as a Potent Inhibitor to Quorum Sensors in Ralstonia solanacearum

by Sunil Kumar, Khurshid Ahmad, Santosh Kumar Behera, Dipak T. Nagrale, Anurag Chaurasia, Manoj Kumar Yadav, Sneha Murmu, Yachana Jha, Mahendra Vikram Singh Rajawat, Deepti Malviya, Udai B. Singh, Raja Shankar, Minaketan Tripathy and Harsh Vardhan Singh

Molecules 2022, 27(9), 3034; https://doi.org/10.3390/molecules27093034 - 09 May 2022

Cited by 4 | Viewed by 2402

Abstract

Ralstonia solanacearum is among the most damaging bacterial phytopathogens with a wide number of hosts and a broad geographic distribution worldwide. The pathway of phenotype conversion (Phc) is operated by quorum-sensing signals and modulated through the (R)-methyl 3-hydroxypalmitate (3-OH PAME) in R. solanacearum [...] Read more.

Ralstonia solanacearum is among the most damaging bacterial phytopathogens with a wide number of hosts and a broad geographic distribution worldwide. The pathway of phenotype conversion (Phc) is operated by quorum-sensing signals and modulated through the (R)-methyl 3-hydroxypalmitate (3-OH PAME) in R. solanacearum. However, the molecular structures of the Phc pathway components are not yet established, and the structural consequences of 3-OH PAME on quorum sensing are not well studied. In this study, 3D structures of quorum-sensing proteins of the Phc pathway (PhcA and PhcR) were computationally modeled, followed by the virtual screening of the natural compounds library against the predicted active site residues of PhcA and PhcR proteins that could be employed in limiting signaling through 3-OH PAME. Two of the best scoring common ligands ZINC000014762512 and ZINC000011865192 for PhcA and PhcR were further analyzed utilizing orbital energies such as HOMO and LUMO, followed by molecular dynamics simulations of the complexes for 100 ns to determine the ligands binding stability. The findings indicate that ZINC000014762512 and ZINC000011865192 may be capable of inhibiting both PhcA and PhcR. We believe that, after further validation, these compounds may have the potential to disrupt bacterial quorum sensing and thus control this devastating phytopathogenic bacterial pathogen. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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21 pages, 3440 KiB  

Open AccessArticle

Production, Bioprocessing and Anti-Proliferative Activity of Camptothecin from Penicillium chrysogenum, “An Endozoic of Marine Sponge, Cliona sp.”, as a Metabolically Stable Camptothecin Producing Isolate

by Ashraf S. A. El-Sayed, Wafaa H. B. Hassan, Sherouk Hussein Sweilam, Mohammed Hamed Saeed Alqarni, Zeinab I. El Sayed, Mahmoud M. Abdel-Aal, Eman Abdelsalam and Sahar Abdelaziz

Molecules 2022, 27(9), 3033; https://doi.org/10.3390/molecules27093033 - 09 May 2022

Cited by 11 | Viewed by 4068

Abstract

Exploring the metabolic potency of fungi as camptothecin producers raises the hope of their usage as an industrial source of camptothecin, due to their short-life span and the feasibility of metabolic engineering. However, the tiny yield and loss of camptothecin productivity of fungi [...] Read more.

Exploring the metabolic potency of fungi as camptothecin producers raises the hope of their usage as an industrial source of camptothecin, due to their short-life span and the feasibility of metabolic engineering. However, the tiny yield and loss of camptothecin productivity of fungi during storage and sub-culturing are challenges that counteract this approach. Marine fungi could be a novel source for camptothecin production, with higher yield and reliable metabolic sustainability. The marine fungal isolate Penicillium chrysogenum EFBL # OL597937.1 derived from the sponge “Cliona sp.” has been morphologically identified and molecularly confirmed, based on the Internal Transcribed Spacer sequence, exhibiting the highest yield of camptothecin (110 μg/L). The molecular structure and chemical identity of P. chrysogenum derived camptothecin has been resolved by HPLC, FTIR and LC-MS/MS analyses, giving the same spectroscopic profiles and mass fragmentation patterns as authentic camptothecin. The extracted camptothecin displayed a strong anti-proliferative activity towards HEP-2 and HCT-116 (IC₅₀ values 0.33–0.35 µM). The yield of camptothecin was maximized by nutritional optimization of P. chrysogenum with a Plackett-Burman design, and the productivity of camptothecin increased by 1.8 fold (200 µg/L), compared to control fungal cultures. Upon storage at 4 °C as slope culture for 8 months, the productivity of camptothecin for P. chrysogenum was reduced by 40% compared to the initial culture. Visual fading of the mycelial pigmentation of P. chrysogenum was observed during fungal storage, matched with loss of camptothecin productivity. Methylene chloride extracts of Cliona sp. had the potency to completely restore the camptothecin productivity of P. chrysogenum, ensuring the partial dependence of the expression of the camptothecin biosynthetic machinery of P. chrysogenum on the chemical signals derived from the sponge, or the associated microbial flora. This is the first report describing the feasibility of P. chrysogenum, endozoic of Cliona sp., for camptothecin production, along with reliable metabolic biosynthetic stability, which could be a new platform for scaling-up camptothecin production. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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19 pages, 1527 KiB  

Open AccessReview

Procyanidins and Their Therapeutic Potential against Oral Diseases

by Huan Chen, Wanyu Wang, Shiyang Yu, Huimin Wang, Zilu Tian and Song Zhu

Molecules 2022, 27(9), 2932; https://doi.org/10.3390/molecules27092932 - 04 May 2022

Cited by 16 | Viewed by 3619

Abstract

Procyanidins, as a kind of dietary flavonoid, have excellent pharmacological properties, such as antioxidant, antibacterial, anti-inflammatory and anti-tumor properties, and so they can be used to treat various diseases, including Alzheimer’s disease, diabetes, rheumatoid arthritis, tumors, and obesity. Given the low bioavailability of [...] Read more.

Procyanidins, as a kind of dietary flavonoid, have excellent pharmacological properties, such as antioxidant, antibacterial, anti-inflammatory and anti-tumor properties, and so they can be used to treat various diseases, including Alzheimer’s disease, diabetes, rheumatoid arthritis, tumors, and obesity. Given the low bioavailability of procyanidins, great efforts have been made in drug delivery systems to address their limited use. Nowadays, the heavy burden of oral diseases such as dental caries, periodontitis, endodontic infections, etc., and their consequences on the patients’ quality of life indicate a strong need for developing effective therapies. Recent years, plenty of efforts are being made to develop more effective treatments. Therefore, this review summarized the latest researches on versatile effects and enhanced bioavailability of procyanidins resulting from innovative drug delivery systems, particularly focused on its potential against oral diseases. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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18 pages, 2733 KiB  

Open AccessArticle

Effects of Cadmium on Physiochemistry and Bioactive Substances of Muskmelon (Cucumis melo L.)

by Yunqiang Wang, Zhen Lei, Rongbin Ye, Wei Zhou, Ying Zhou, Zhengkang Zou, Junli Li, Licong Yi and Zhaoyi Dai

Molecules 2022, 27(9), 2913; https://doi.org/10.3390/molecules27092913 - 03 May 2022

Cited by 4 | Viewed by 2041

Abstract

Muskmelon pedicel is the fruit stalk of muskmelon and one of the traditional Chinese medicines, which can be used to treat jaundice, diabetes and neuropathy. However, in recent years, agricultural soil heavy metal cadmium (Cd) pollution has become serious, coupled with the imperfect [...] Read more.

Muskmelon pedicel is the fruit stalk of muskmelon and one of the traditional Chinese medicines, which can be used to treat jaundice, diabetes and neuropathy. However, in recent years, agricultural soil heavy metal cadmium (Cd) pollution has become serious, coupled with the imperfect sales management of herbal medicine, increasing the potential health risk of contaminated herbal medicine in the human body. In this paper, the comprehensive quality of contaminated muskmelon was tested. The results showed that Cd stress significantly inhibited the growth of muskmelon plants, reduced the anthocyanin and chlorophyll contents, and increased the fruit size and sweetness of muskmelon. In addition, heavy metal Cd can also cause oxidative stress in plants, resulting in a series of changes in antioxidant enzyme activities. In the experimental group, the content of polyphenols and saponins increased by 27.02% and 23.92%, respectively, after high-concentration Cd treatment, which may be a mechanism of plant resistance to stress. This paper reveals that the content of bioactive substances in Chinese herbal medicine is high, but the harm in heavy metals cannot be underestimated, which should be paid attention to by relevant departments. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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18 pages, 5637 KiB  

Open AccessArticle

Cannabis sativa CBD Extract Shows Promising Antibacterial Activity against Salmonella typhimurium and S. newington

by Logan Gildea, Joseph Atia Ayariga, Olufemi S. Ajayi, Junhuan Xu, Robert Villafane and Michelle Samuel-Foo

Molecules 2022, 27(9), 2669; https://doi.org/10.3390/molecules27092669 - 21 Apr 2022

Cited by 18 | Viewed by 6397

Abstract

Products derived from Cannabis sativa L. have gained increased interest and popularity. As these products become common amongst the public, the health and potential therapeutic values associated with hemp have become a premier focus of research. While the psychoactive and medicinal properties of [...] Read more.

Products derived from Cannabis sativa L. have gained increased interest and popularity. As these products become common amongst the public, the health and potential therapeutic values associated with hemp have become a premier focus of research. While the psychoactive and medicinal properties of Cannabis products have been extensively highlighted in the literature, the antibacterial properties of cannabidiol (CBD) have not been explored in depth. This research serves to examine the antibacterial potential of CBD against Salmonella newington and S. typhimurium. In this study, we observed bacterial response to CBD exposure through biological assays, bacterial kinetics, and fluorescence microscopy. Additionally, comparative studies between CBD and ampicillin were conducted against S. typhimurium and S. newington to determine comparative efficacy. Furthermore, we observed potential resistance development of our Salmonella spp. against CBD treatment. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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18 pages, 5149 KiB  

Open AccessArticle

Fabrication and In Vitro/Vivo Evaluation of Drug Nanocrystals Self-Stabilized Pickering Emulsion for Oral Delivery of Quercetin

by Zhe Wang, Bo Dai, Xiaohan Tang, Zhihui Che, Fei Hu, Chengying Shen, Wei Wu, Baode Shen and Hailong Yuan

Pharmaceutics 2022, 14(5), 897; https://doi.org/10.3390/pharmaceutics14050897 - 20 Apr 2022

Cited by 10 | Viewed by 2565

Abstract

The aim of this study was to develop a new drug nanocrystals self-stabilized Pickering emulsion (NSSPE) for improving oral bioavailability of quercetin (QT). Quercetin nanocrystal (QT–NC) was fabricated by high pressure homogenization method, and QT–NSSPE was then prepared by ultrasound method with QT–NC [...] Read more.

The aim of this study was to develop a new drug nanocrystals self-stabilized Pickering emulsion (NSSPE) for improving oral bioavailability of quercetin (QT). Quercetin nanocrystal (QT–NC) was fabricated by high pressure homogenization method, and QT–NSSPE was then prepared by ultrasound method with QT–NC as solid particle stabilizer and optimized by Box-Behnken design. The optimized QT–NSSPE was characterized by fluorescence microscope (FM), scanning electron micrograph (SEM), X-ray diffraction (XRD), and differential scanning calorimetry (DSC). The stability, in vitro release, and in vivo oral bioavailability of QT–NSSPE were also investigated. Results showed that the droplets of QT–NSSPE with the size of 10.29 ± 0.44 μm exhibited a core-shell structure consisting of a core of oil and a shell of QT–NC. QT–NSSPE has shown a great stability in droplets shape, size, creaming index, zeta potential, and QT content during 30 days storage at 4, 25, and 40 °C. In vitro release studies showed that QT–NSSPE performed a better dissolution behavior (65.88% within 24 h) as compared to QT–NC (50.71%) and QT coarse powder (20.15%). After oral administration, the AUC_0–t of QT–NSSPE was increased by 2.76-times and 1.38 times compared with QT coarse powder and QT–NC. It could be concluded that NSSPE is a promising oral delivery system for improving the oral bioavailability of QT. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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11 pages, 1546 KiB  

Open AccessArticle

Comparison between Quality Traits of Solar-Dried and Freeze-Dried Origanum syriacum L. (Za’atar)

by Reem Abu Alwafa, Samer Mudalal, Faisal Shraim and Gianluigi Mauriello

Plants 2022, 11(9), 1110; https://doi.org/10.3390/plants11091110 - 20 Apr 2022

Cited by 2 | Viewed by 1748

Abstract

There is growing interest in Origanum syriacum due to attractive culinary applications and functional properties. Solar drying is the most common conventional method for drying Origanum syriacum L. (Za’atar) in Mediterranean region. This study aimed to evaluate the quality traits of solar dried [...] Read more.

There is growing interest in Origanum syriacum due to attractive culinary applications and functional properties. Solar drying is the most common conventional method for drying Origanum syriacum L. (Za’atar) in Mediterranean region. This study aimed to evaluate the quality traits of solar dried za’atar in comparison to freeze dried za’atar. Proximate composition (moisture, protein, fat, fiber, carbohydrates, and ash), color index (L*a*b*), macro and microstructure, sensory, and microbiological characteristics were evaluated. Solar dried za’atar exhibited significantly lower fat content (1.10 vs. 1.64%, p < 0.05) than freeze dried za’atar. Solar drying led to severe changes in color values compared to freeze drying. Solar drying exhibited loss in the structural integrity and leave hairs more than freeze drying. Moreover, freeze-dried za’atar exhibited significantly lower total aerobic count (4.92 vs. 5.23, p < 0.05) and yeasts and mold count (4.59 vs. 5.36, p < 0.05) than solar-dried za’atar. Panelists were able significantly to differentiate between solar- and freeze dried za’atar. Freeze-dried za’atar had significantly lower hedonic score of color, odor, taste, and overall acceptance than solar dried za’atar. In conclusion, using freeze drying achieved good improvements in some quality traits for za’atar while solar dried za’atar showed better sensory perception. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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8 pages, 11886 KiB  

Open AccessArticle

Naphtho-Gamma-Pyrones (NγPs) with Obvious Cholesterol Absorption Inhibitory Activity from the Marine-Derived Fungus Aspergillus niger S-48

by Chang-Zheng Wu, Xiao-Ping Peng, Gang Li, Qi Wang and Hong-Xiang Lou

Molecules 2022, 27(8), 2514; https://doi.org/10.3390/molecules27082514 - 13 Apr 2022

Cited by 3 | Viewed by 1478

Abstract

Eight naphtho-gamma-pyrones (NγPs) (1–8), together with four known biosynthetically related coumarin derivatives (9–12), were isolated from the potato dextrose agar media of a marine-derived fungus Aspergillus niger S-48. Among them, natural compounds 1 [...] Read more.

Eight naphtho-gamma-pyrones (NγPs) (1–8), together with four known biosynthetically related coumarin derivatives (9–12), were isolated from the potato dextrose agar media of a marine-derived fungus Aspergillus niger S-48. Among them, natural compounds 1 and 2 were tentatively subjected to benzohydrazide reaction to evaluate the importance of pyran rings in NγPs. Their structures were elucidated by extensive 1D and 2D NMR spectroscopic data and MS spectra. Compounds 1–4 showed obvious activity for reducing cholesterol absorption verging on ezetimibe. This work highlighted the potential of natural NγPs as NPC1L1 inhibitors. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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16 pages, 7895 KiB  

Open AccessArticle

Nigrosporins B, a Potential Anti-Cervical Cancer Agent, Induces Apoptosis and Protective Autophagy in Human Cervical Cancer Ca Ski Cells Mediated by PI3K/AKT/mTOR Signaling Pathway

by Jing Zhang, Zhi-Yong Guo, Chang-Lun Shao, Xue-Qing Zhang, Fan Cheng, Kun Zou and Jian-Feng Chen

Molecules 2022, 27(8), 2431; https://doi.org/10.3390/molecules27082431 - 09 Apr 2022

Cited by 4 | Viewed by 1819

Abstract

Nigrosporins B, an anthraquinone derivative obtained from the secondary metabolites of marine fungus Nigrospora oryzae. In this study, we characterized the distinctive anti-cancer potential of Nigrosporins B in vitro and underlying molecular mechanisms in human cervical cancer Ca Ski cells for the [...] Read more.

Nigrosporins B, an anthraquinone derivative obtained from the secondary metabolites of marine fungus Nigrospora oryzae. In this study, we characterized the distinctive anti-cancer potential of Nigrosporins B in vitro and underlying molecular mechanisms in human cervical cancer Ca Ski cells for the first time. The results of MTT assay showed that Nigrosporins B significantly inhibited the proliferation of multiple tumor cells in a dose-dependent manner, especially for the Ca Ski cells with an IC₅₀ of 1.24 µM. Nigrosporins B exerted an apoptosis induction effect on Ca Ski cells as confirmed by flow cytometry, AO/EB dual fluorescence staining, mitochondrial membrane potential analysis and western blot assay. In addition, Nigrosporins B induced obvious autophagy accompanied with the increase of autophagic vacuoles and the acceleration of autophagic flux as indicated by Cyto-ID staining, mRFP-GFP-LC3 adenovirus transfection and western blot analysis. Interestingly, the combination of Nigrosporins B with the three autophagy inhibitors all significantly enhanced the cytotoxicity of Nigrosporins B on Ca Ski cells, indicating that the autophagy induced by Nigrosporins B might protect Ca Ski cells from death. Furthermore, we found that Nigrosporins B inhibited the phosphorylation of PI3K, AKT, mTOR molecules and increased the protein expression levels of PTEN and p-AMPKα in a dose-dependent manner, suggesting that Nigrosporins B induced apoptosis and protective autophagy through the suppression of the PI3K/AKT/mTOR signaling pathway. Together, these findings revealed the anti-cervical cancer effect of Nigrosporins B and the underlying mechanism of action in Ca Ski cells, it might be as a promising alternative therapeutic agent for human cervical cancer. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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14 pages, 5370 KiB  

Open AccessArticle

Degradation and Pathways of Carvone in Soil and Water

by Chenyu Huang, Wenwen Zhou, Chuanfei Bian, Long Wang, Yuqi Li and Baotong Li

Molecules 2022, 27(8), 2415; https://doi.org/10.3390/molecules27082415 - 08 Apr 2022

Cited by 3 | Viewed by 2197

Abstract

Carvone is a monoterpene compound that has been widely used as a pesticide for more than 10 years. However, little is known regarding the fate of carvone, or its degradation products, in the environment. We used GC-MS (gas chromatography–mass spectrometry) to study the [...] Read more.

Carvone is a monoterpene compound that has been widely used as a pesticide for more than 10 years. However, little is known regarding the fate of carvone, or its degradation products, in the environment. We used GC-MS (gas chromatography–mass spectrometry) to study the fate of carvone and its degradation and photolysis products under different soil and light conditions. We identified and quantified three degradation products of carvone in soil and water samples: dihydrocarvone, dihydrocarveol, and carvone camphor. In soil, dihydrocarveol was produced at very low levels (≤0.067 mg/kg), while dihydrocarvone was produced at much higher levels (≤2.07 mg/kg). In water exposed to differing light conditions, carvone was degraded to carvone camphor. The photolysis rate of carvone camphor under a mercury lamp was faster, but its persistence was lower than under a xenon lamp. The results of this study provide fundamental data to better understand the fate and degradation of carvone and its metabolites in the environment. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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8 pages, 539 KiB  

Open AccessArticle

Bioactive Terphenyls Isolated from the Antarctic Lichen Stereocaulon alpinum

by Kim-Hoa Phi, Min-Ji Shin, Seulah Lee, Jae Eun So, Ji Hee Kim, Sung-Suk Suh, Man Hyung Koo, Seung Chul Shin, Jin-Hyoung Kim, Jun Hyuck Lee and Ui Joung Youn

Molecules 2022, 27(7), 2363; https://doi.org/10.3390/molecules27072363 - 06 Apr 2022

Cited by 3 | Viewed by 1977

Abstract

Three p-terphenyls (2–4)—2-hydroxy-3,5-dimethoxy-p-terphenyl (2), 2-hydroxy-3,6-dimethoxy-p-terphenyl (3), and 2,3,5,6-tetramethoxy-p-terphenyl (4)—were isolated for the first time as natural products along with seven known compounds (1, 5 [...] Read more.

Three p-terphenyls (2–4)—2-hydroxy-3,5-dimethoxy-p-terphenyl (2), 2-hydroxy-3,6-dimethoxy-p-terphenyl (3), and 2,3,5,6-tetramethoxy-p-terphenyl (4)—were isolated for the first time as natural products along with seven known compounds (1, 5–10) from the Antarctic lichen Stereocaulon alpinum. Structures of the new compounds were elucidated by comprehensive analyses of 1D and 2D NMR and HREIMS experiments. Compound 3 exhibited cytotoxicity against HCT116 cells with the IC₅₀ value of 3.76 ± 0.03 μM and also inhibited NO production in LPS-induced RAW264.7 macrophages with the IC₅₀ value of 22.82 ± 0.015 μM. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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11 pages, 2072 KiB  

Open AccessCommunication

A New Labdane-Type Diterpene, 6-O-Acetyl-(12R)-epiblumdane, from Stevia rebaudiana Leaves with Insulin Secretion Effect

by Heesun Kang, Dahae Lee, Ki Sung Kang and Ki Hyun Kim

Biomedicines 2022, 10(4), 839; https://doi.org/10.3390/biomedicines10040839 - 03 Apr 2022

Viewed by 1775

Abstract

Stevia rebaudiana (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive [...] Read more.

Stevia rebaudiana (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of S. rebaudiana leaves led to the isolation of one new labdane-type diterpene, 6-O-acetyl-(12R)-epiblumdane (1), and nine known terpenoids, including six diterpenes (2–6 and 10), two monoterpenes (7 and 8), and one triterpene (9). The structure of the new compound 1 was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds 1–10 were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound 1, 6-O-acetyl-(12R)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-O-acetyl-(12R)-epiblumdane (1), an active compound derived from S. rebaudiana leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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13 pages, 1996 KiB  

Open AccessArticle

Diphlorethohydroxycarmalol Derived from Ishige okamurae Improves Behavioral and Physiological Responses of Muscle Atrophy Induced by Dexamethasone in an In-Vivo Model

by Bomi Ryu, Seyeon Oh, Hye-Won Yang, Batsukh Sosorburam, Dong-Min Chung, Minyoung Seo, Shin-Jae Park, Kyunghee Byun and You-Jin Jeon

Pharmaceutics 2022, 14(4), 719; https://doi.org/10.3390/pharmaceutics14040719 - 27 Mar 2022

Cited by 7 | Viewed by 2376

Abstract

Muscle atrophy refers to the loss of skeletal muscle mass, myofiber size, and related physical functions such as walking speed or grip strength caused by aging or a lack of physical activity due to injury or illness and can also be attributed to [...] Read more.

Muscle atrophy refers to the loss of skeletal muscle mass, myofiber size, and related physical functions such as walking speed or grip strength caused by aging or a lack of physical activity due to injury or illness and can also be attributed to excessive exposure to corticosteroids. Ishige okamurae (IO) and its active component, diphlorethohydroxycarmalol (DPHC), have been known to improve glucose homeostasis by controlling the contraction of skeletal muscles. Based on this idea, we hypothesized that the effects of DPHC and IO extract on muscle metabolism are associated with their role in improving muscle physical function. This study assessed the effects of DPHC or IO extract on muscle behavioral responses with their metabolic properties in muscle atrophy induced by glucocorticoids and dexamethasone (DEX) in vivo. In addition to the improvement in muscle behavioral response by DPHC or IO extract, the loss of muscle fiber and the related metabolic properties by DEX exposure in the gastrocnemius and soleus of calf muscle was prevented. These findings suggest that IO extract and its active component DPHC can potentially prevent muscle atrophy caused by exposure to corticosteroids and could be used to treat reverse skeletal atrophy. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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25 pages, 9870 KiB  

Open AccessReview

Research Progress of Natural Small-Molecule Compounds Related to Tumor Differentiation

by Xiaoli He, Yongkang Liao, Jing Liu and Shuming Sun

Molecules 2022, 27(7), 2128; https://doi.org/10.3390/molecules27072128 - 25 Mar 2022

Cited by 7 | Viewed by 2481

Abstract

Tumor differentiation is a therapeutic strategy aimed at reactivating the endogenous differentiation program of cancer cells and inducing cancer cells to mature and differentiate into other types of cells. It has been found that a variety of natural small-molecule drugs can induce tumor [...] Read more.

Tumor differentiation is a therapeutic strategy aimed at reactivating the endogenous differentiation program of cancer cells and inducing cancer cells to mature and differentiate into other types of cells. It has been found that a variety of natural small-molecule drugs can induce tumor cell differentiation both in vitro and in vivo. Relevant molecules involved in the differentiation process may be potential therapeutic targets for tumor cells. Compared with synthetic drugs, natural small-molecule antitumor compounds have the characteristics of wide sources, structural diversity and low toxicity. In addition, natural drugs with structural modification and transformation have relatively concentrated targets and enhanced efficacy. Therefore, using natural small-molecule compounds to induce malignant cell differentiation represents a more targeted and potential low-toxicity means of tumor treatment. In this review, we focus on natural small-molecule compounds that induce differentiation of myeloid leukemia cells, osteoblasts and other malignant cells into functional cells by regulating signaling pathways and the expression of specific genes. We provide a reference for the subsequent development of natural small molecules for antitumor applications and promote the development of differentiation therapy. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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11 pages, 3075 KiB  

Open AccessArticle

Effects of Artonin E on Cell Growth Inhibition and Apoptosis Induction in Colon Cancer LoVo and HCT116 Cells

by Kanyaluck Yangnok, Sukanda Innajak, Ratchawin Sawasjirakij, Wilawan Mahabusarakam and Ramida Watanapokasin

Molecules 2022, 27(7), 2095; https://doi.org/10.3390/molecules27072095 - 24 Mar 2022

Cited by 7 | Viewed by 2633

Abstract

Today, colon cancer is the leading cause of cancer death. In Thailand, colon cancer is the third most common cancer in men and the second in women. Currently, the treatments for colon cancer include surgery, chemotherapy, radiation therapy, immunotherapy, hormone therapy, targeted drug [...] Read more.

Today, colon cancer is the leading cause of cancer death. In Thailand, colon cancer is the third most common cancer in men and the second in women. Currently, the treatments for colon cancer include surgery, chemotherapy, radiation therapy, immunotherapy, hormone therapy, targeted drug therapy, and stem cell therapy. However, some treatments have side effects for cancer patients, causing unwanted symptoms. In addition, targeted therapy comes with a high cost for patients. Therefore, bioactive compounds might be a good choice for colon cancer treatment. In this study, we investigated the effect of artonin E on apoptosis induction in colon cancer LoVo and HCT116 cells. The concentration ranges of artonin E at 3, 5, 10, and 30 µg/mL in LoVo cells and 1, 1.5, 2, and 3 µg/mL in HCT116 cells were examined. The results implied that artonin E decreased cell viability and increased apoptotic cells in a dose-dependent manner. In addition, artonin E stimulated mitochondrial membrane potential (ΔΨm) changes associated with apoptosis by increasing the sub-G1 population analyzed by flow cytometry. Western blotting showed that artonin E increased the proapoptotic protein, Bax, and decreased anti-apoptotic proteins’ (Bcl-2 and Bcl-x) expression. Moreover, artonin E also increased cleaved caspase-7 and cleaved-PARP expression in both LoVo and HCT116 cells. Interestingly, artonin E induced apoptosis through p-ERK1/2, p-p38/p38, and p-c-Jun expression in both cells. Our results suggested that artonin E induced apoptosis via caspase activation associated with the MAPKs signaling pathway. Therefore, artonin E might be used as a potential anticancer drug for colon cancer in the future. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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17 pages, 1517 KiB  

Open AccessArticle

Comparative Studies on Essential Oil and Phenolic Content with In Vitro Antioxidant, Anticholinesterase, Antimicrobial Activities of Achillea biebersteinii Afan. and A. millefolium subsp. millefolium Afan. L. Growing in Eastern Turkey

by Gizem Gülsoy Toplan, Turgut Taşkın, Gökalp İşcan, Fatih Göger, Mine Kürkçüoğlu, Ayşe Civaş, Gülay Ecevit-Genç, Afife Mat and Kemal Hüsnü Can Başer

Molecules 2022, 27(6), 1956; https://doi.org/10.3390/molecules27061956 - 17 Mar 2022

Cited by 10 | Viewed by 2798

Abstract

The potential applications of Achillea species in various industries have encouraged the examination of their phytochemical components along with their biological potential. In the present study, phenolic contents and essential oil compositions together with the in vitro biological activities of the aerial parts [...] Read more.

The potential applications of Achillea species in various industries have encouraged the examination of their phytochemical components along with their biological potential. In the present study, phenolic contents and essential oil compositions together with the in vitro biological activities of the aerial parts from Achillea biebersteinii Afan. and Achillea millefolium subsp. millefolium Afan. collected from Turkey were evaluated. Different solvent extracts (n-hexane, chloroform, methanol, water) were prepared and their antimicrobial, anticholinesterase, and antioxidant activities were studied. The LC-MS/MS results revealed the presence of 16 different phenolic compounds, including chlorogenic acid, rutin, quercetin, and luteolin glycosides, in methanolic extracts. According to GC-FID and GC/MS results, the primary components of the oils were identified as 1,8-cineole (32.5%), piperitone (14.4%), and camphor (13.7%) in A. biebersteinii and 1,8-cineole (12.3%) and β-eudesmol (8.9%) in A. millefolium subsp. millefolium. The infusion and methanolic extracts of both species were found to be rich in their total phenolic content as well as their antioxidant and anticholinesterase activity. In contrast, the n-hexane and chloroform extracts of both species showed strong antimicrobial activity with MIC values ranging from 15 to 2000 μg/mL. Our findings suggest that the investigated Achillea species could be evaluated as potent natural agents, and further studies into the promising extracts are needed. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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20 pages, 1591 KiB  

Open AccessArticle

Antioxidant and Cytotoxic Activities of Kudzu Roots and Soy Molasses against Pediatric Tumors and Phytochemical Analysis of Isoflavones Using HPLC-DAD-ESI-HRMS

by Saied A. Aboushanab, Vadim A. Shevyrin, Grigory P. Slesarev, Vsevolod V. Melekhin, Anna V. Shcheglova, Oleg G. Makeev, Elena G. Kovaleva and Ki Hyun Kim

Plants 2022, 11(6), 741; https://doi.org/10.3390/plants11060741 - 10 Mar 2022

Cited by 10 | Viewed by 4521

Abstract

Pediatric solid tumors (PSTs) are life-threatening and can lead to high morbidity and mortality rates in children. Developing novel remedies to treat these tumors, such as glioblastoma multiforme and sarcomas, such as osteosarcoma, and rhabdomyosarcoma, is challenging, despite immense attempts with chemotherapeutic or [...] Read more.

Pediatric solid tumors (PSTs) are life-threatening and can lead to high morbidity and mortality rates in children. Developing novel remedies to treat these tumors, such as glioblastoma multiforme and sarcomas, such as osteosarcoma, and rhabdomyosarcoma, is challenging, despite immense attempts with chemotherapeutic or radiotherapeutic interventions. Soy (Glycine max) and kudzu roots (KR) (Pueraria spp.) are well-known phytoestrogenic botanical sources that contain high amounts of naturally occurring isoflavones. In the present study, we investigated the antioxidant and cytotoxic effects of the extracts of KR and soy molasses (SM) against PSTs. The green extraction of isoflavones from KR and SM was performed using natural deep eutectic solvents. The extracts were subsequently analyzed by high-performance liquid chromatography (HPLC)-diode array detector (DAD) coupled with high-resolution (HR) mass spectrometry (MS), which identified 10 isoflavones in KR extracts and 3 isoflavones in the SM extracts. Antioxidant and cytotoxic activities of KR and SM extracts were assessed against glioblastoma multiforme (A-172), osteosarcoma (HOS), and rhabdomyosarcoma (Rd) cancer cell lines. The KR and SM extracts showed satisfactory cytotoxic effects (IC₅₀) against the cancer cell lines tested, particularly against Rd cancer cell lines, in a dose-dependent manner. Antioxidant activity was found to be significantly (p ≤ 0.05) higher in KR than in SM, which was consistent with the results of the cytotoxic activity observed with KR and SM extracts against glioblastoma and osteosarcoma cells. The total flavonoid content and antioxidant activities of the extracts were remarkably attributed to the isoflavone content in the KR and SM extracts. This study provides experimental evidence that HPLC-ESI-HRMS is a suitable analytical approach to identify isoflavones that exhibit potent antioxidant and anticancer potential against tumor cells, and that KR and SM, containing many isoflavones, can be a potential alternative for health care in the food and pharmaceutical industries. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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15 pages, 1488 KiB  

Open AccessArticle

Rare β-Resorcylic Acid Derivatives from a Halophyte-Associated Fungus Colletotrichum gloeosporioides JS0419 and Their Antifungal Activities

by Sunghee Bang, Jaekyeong Kim, Jiwon Oh, Ji-Seok Kim, Seong-Ryong Yu, Stephen Deyrup, Yong-Sun Bahn and Sang Hee Shim

Mar. Drugs 2022, 20(3), 195; https://doi.org/10.3390/md20030195 - 07 Mar 2022

Cited by 6 | Viewed by 2599

Abstract

Six new β-resorcylic acid derivatives (1–5 and 7) were isolated from a halophyte-associated fungus, Colletotrichum gloeosporioides JS0419, together with four previously reported β-resorcylic acid lactones (RALs). The relative and absolute stereochemistry of 1 was completely established by a combination [...] Read more.

Six new β-resorcylic acid derivatives (1–5 and 7) were isolated from a halophyte-associated fungus, Colletotrichum gloeosporioides JS0419, together with four previously reported β-resorcylic acid lactones (RALs). The relative and absolute stereochemistry of 1 was completely established by a combination of spectroscopic data and chemical reactions. The structures of the isolated compounds were elucidated by analysis of HRMS and NMR data. Notably, compounds 1–3 had a β-resorcylic acid harboring a long unesterified aliphatic side chain, whereas the long aliphatic chains were esterified to form macrolactones in 4–9. Among the isolated compounds, monocillin I and radicicol showed potent antifungal activities against Cryptococcus neoformans, comparable to clinically available antifungal agents and radicicol showed weak antifungal activity against Candida albicans. These findings provide insight into the chemical diversity of fungal RAL-type compounds and their pharmacological potential. Full article

(This article belongs to the Topic Advances in Natural Products from Plants and Associated Microbes)

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