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Open AccessArticle

Effect of the Harvest Season of Anthyllis henoniana Stems on Antioxidant and Antimicrobial Activities: Phytochemical Profiling of Their Ethyl Acetate Extracts

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Raoudha Mezghani-Jarraya

Molecules 2023, 28(9), 3947; https://doi.org/10.3390/molecules28093947 - 07 May 2023

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Abstract

Anthyllis henoniana stems were harvested in two seasons: winter and spring (February and May 2021). In this study, we investigated the antioxidant (DPPH, ABTS, FRAP and TAC) and antimicrobial activities, total phenolic contents and total flavonoid contents of the obtained extracts (hexane, ethyl [...] Read more.

Anthyllis henoniana stems were harvested in two seasons: winter and spring (February and May 2021). In this study, we investigated the antioxidant (DPPH, ABTS, FRAP and TAC) and antimicrobial activities, total phenolic contents and total flavonoid contents of the obtained extracts (hexane, ethyl acetate and methanol). The results showed that ethyl acetate extract from stems harvested in winter exhibited the highest antioxidant activity, while ethyl acetate extract from the stems harvested in spring showed the most potent antibacterial and antifungal activities. To explain these differences, we investigated the phytochemical composition of these two extracts using liquid chromatography coupled with mass spectrometry. Therefore, 45 compounds were detected, from which we identified 20 compounds (flavonoids, triterpenoids, chalcones and phenolic acids); some were specific to the harvest month while others were common for both periods. Some of the major compounds detected in ethyl acetate (spring) were dihydrochalcone (Kanzonol Y, 8.2%) and flavanone (sophoraflavanone G, 5.9%), previously recognized for their antimicrobial effects. We therefore concluded that the difference in activities observed for the two harvest periods depends on the chemical composition of the extracts and the relative abundance of each compound. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

New Tricholidic Acid Triterpenoids from the Mushroom Tricholoma ustaloides Collected in an Italian Beech Wood

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Molecules 2023, 28(9), 3864; https://doi.org/10.3390/molecules28093864 - 04 May 2023

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The secondary metabolites produced by Tricholoma ustaloides Romagn., a mushroom species belonging to the large Tricholoma genus (Basidiomycota, Tricholomataceae), are unknown. Therefore, encouraged by the interesting results obtained in our previous chemical analyses of a few Tricholoma species collected in Italian woods, we [...] Read more.

The secondary metabolites produced by Tricholoma ustaloides Romagn., a mushroom species belonging to the large Tricholoma genus (Basidiomycota, Tricholomataceae), are unknown. Therefore, encouraged by the interesting results obtained in our previous chemical analyses of a few Tricholoma species collected in Italian woods, we aimed to investigate the secondary metabolites of Tricholoma ustaloides. The chemical analysis involved the isolation and characterization of secondary metabolites through an extensive chromatographic study. The structures of isolated metabolites, including the absolute configuration, were established based on a detailed analysis of MS, NMR spectroscopic, optical rotation, and circular dicroism data, and on comparison with those of related compounds reported in the literature. Two novel lanostane triterpenoids, named tricholidic acids B and C, together with triglycerides, a mixture of free fatty acids, five unidentified metabolites, and the known rare saponaceolides F and J, tricholidic acid, and tricholomenyn C, were isolated from an EtOAc extract of fruiting bodies of Tricholoma ustaloides that were collected in an Italian beech wood. This is the second example of isolation of tricholidic acid derivatives from a natural source. Saponaceolides F and J exhibited high cytotoxicity (IC₅₀ values ≤ 10 μM) against a panel of five human cancer cell lines. The toxicity against myeloid leukemia (HL-60), lung cancer (A-549), hepatocellular cancer (HepG2), renal cancer (Caki-1), and breast cancer (MCF-7) cells was higher than that shown by the very well-known cytotoxic drug cisplatin. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Extraction, Purification, and Component Identification of Monoterpene Glycosides from Paeonia suffruticosa Seed Meal

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Molecules 2023, 28(8), 3498; https://doi.org/10.3390/molecules28083498 - 15 Apr 2023

Viewed by 556

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Paeonia suffruticosa (P. suffruticosa) seed meal is a byproduct of P. suffruticosa seed processing, which contains bioactive substances such as monoterpene glycosides, and has not been effectively utilized at present. In this study, monoterpene glycosides were extracted from P. suffruticosa seed [...] Read more.

Paeonia suffruticosa (P. suffruticosa) seed meal is a byproduct of P. suffruticosa seed processing, which contains bioactive substances such as monoterpene glycosides, and has not been effectively utilized at present. In this study, monoterpene glycosides were extracted from P. suffruticosa seed meal using an ultrasound-assisted ethanol extraction process. The monoterpene glycoside extract was then purified by macroporous resin and identified using HPLC-Q-TOF-MS/MS. The results indicated the following optimal extraction conditions: ethanol concentration, 33%; ultrasound temperature, 55 °C; ultrasound power, 400 W; liquid–material ratio, 33:1; and ultrasound time, 44 min. Under these conditions, the yield of monoterpene glycosides was 121.03 mg/g. The purity of the monoterpene glycosides increased from 20.5% (crude extract) to 71.2% (purified extract) when using LSA-900C macroporous resin. Six monoterpene glycosides (oxy paeoniflorin, isomaltose paeoniflorin, albiflorin, 6′-O-β-D-glucopyranoside albiflorin, paeoniflorin, and Mudanpioside i) were identified from the extract using HPLC-Q-TOF-MS/MS. The main substances were albiflorin and paeoniflorin, and the contents were 15.24 mg/g and 14.12 mg/g, respectively. The results of this study can provide a theoretical basis for the effective utilization of P. suffruticosa seed meal. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Yield and Composition of the Essential Oil of the Opopanax Genus in Turkey

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Molecules 2023, 28(7), 3055; https://doi.org/10.3390/molecules28073055 - 29 Mar 2023

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The genus Opopanax W. Koch (Apiaceae) is represented by four species in Turkey. The composition of the essential oil of Opopanax genus members (Apiaceae) growing in Turkey was investigated in this study. GC-MS was used to analyze the composition of Opopanax essential oil [...] Read more.

The genus Opopanax W. Koch (Apiaceae) is represented by four species in Turkey. The composition of the essential oil of Opopanax genus members (Apiaceae) growing in Turkey was investigated in this study. GC-MS was used to analyze the composition of Opopanax essential oil samples that were taken from their natural environments. The Clevenger apparatus was used to hydrodistill the plant’s aerial parts, and the yields were determined to be between 0.2% v/w (for O. siifolius) and 0.4% (for O. hispidus, O. chironium, and O. persicus). The results and the chemical data provided some information and clues on the chemotaxonomy of the genus Opopanax. In this study, γ-elemene, butanoic acid octyl ester, and cylopropane were the main compounds identified in the essential oils of O. chironium, O. hispidus, and O. persicus. In particular, hexynyl n-valerate was most abundant in the essential oil of O. chironium, cyclopropane in that of O. hispidus, γ-elemene in that of O. persicus, and n-hexadecanoic acid/palmitic acid in that of O. siifolius. In a chemotaxonomic approach, the essential oil analysis of the Opopanax species revealed that these species conformed in a cluster analysis with their morphological classification. The constituents of the essential oils of all examined in the genus Opopanax were determined in this study, which is the most thorough one to date. This study provides new information about the composition of the essential oils of the investigated species. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Two Onnamide Analogs from the Marine Sponge Theonella conica: Evaluation of Geometric Effects in the Polyene Systems on Biological Activity

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Molecules 2023, 28(6), 2524; https://doi.org/10.3390/molecules28062524 - 09 Mar 2023

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Two previously unreported onnamide analogs, 2Z- and 6Z-onnamides A (1 and 2), were isolated from the marine sponge Theonella conica collected at Amami-Oshima Is., Kagoshima Prefecture, Japan. Structures of compounds 1 and 2 were elucidated by spectral [...] Read more.

Two previously unreported onnamide analogs, 2Z- and 6Z-onnamides A (1 and 2), were isolated from the marine sponge Theonella conica collected at Amami-Oshima Is., Kagoshima Prefecture, Japan. Structures of compounds 1 and 2 were elucidated by spectral analysis. Structure–activity relationships (SARs) for effects on histone modifications and cytotoxicity against HeLa and P388 cells were characterized. The geometry in the polyene systems of onnamides affected the histone modification levels and cytotoxicity. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

The Phenolic Compounds’ Role in Beer from Various Adjuncts

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Molecules 2023, 28(5), 2295; https://doi.org/10.3390/molecules28052295 - 01 Mar 2023

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Background: The present article considers the influence of malt with various adjuncts on beer organic compounds and taste profile composition, with more attention paid to the phenol complex change. The topic under consideration is relevant since it studies the interactions of phenolic compounds [...] Read more.

Background: The present article considers the influence of malt with various adjuncts on beer organic compounds and taste profile composition, with more attention paid to the phenol complex change. The topic under consideration is relevant since it studies the interactions of phenolic compounds with other biomolecules, and expands the understanding of the adjuncts organic compounds contribution and their joint effect on beer quality. Methods: Samples of beer were analyzed at a pilot brewery using barley and wheat malts, barley, rice, corn and wheat, and then fermented. The beer samples were assessed by industry-accepted methods and using instrumental analysis methods (high-performance liquid chromatography methods—HPLC). The obtained statistical data were processed by the Statistics program (Microsoft Corporation, Redmond, WA, USA, 2006). Results: The study showed that at the stage of hopped wort organic compounds structure formation, there is a clear correlation between the content of organic compounds and dry substances, including phenolic compounds (quercetin, catechins), as well as isomerized hop bitter resines. It is shown that the riboflavin content increases in all adjunct wort samples, and mostly with the use of rice—up to 4.33 mg/L, which is 9.4 times higher than the vitamin levels in malt wort. The melanoidin content in the samples was in the range of 125–225 mg/L and its levels in the wort with additives exceeded the malt wort. Changes in β-glucan and nitrogen with thiol groups during fermentation occurred with different dynamics and depending on the adjunct’s proteome. The greatest decrease in non-starch polysaccharide content was observed in wheat beer and nitrogen with thiol groups content—in all other beer samples. The change in iso-α-humulone in all samples at the beginning of fermentation correlated with a decrease in original extract, and in the finished beer there was no correlation. The behavior of catechins, quercetin, and iso-α-humulone has been shown to correlate with nitrogen with thiol groups during fermentation. A strong correlation was shown between the change in iso-α-humulone and catechins, as well as riboflavin and quercetin. It was established that various phenolic compounds were involved in the formation of taste, structure, and antioxidant properties of beer in accordance with the structure of various grains, depending on the structure of its proteome. Conclusions: The obtained experimental and mathematical dependences make it possible to expand the understanding of intermolecular interactions of beer organic compounds and take a step toward predicting the quality of beer at the stage of using adjuncts. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Essential Oil Composition and Enantioselective Profile of Agastache urticifolia (Lamiaceae) and Monardella odoratissima (Lamiaceae) from Utah

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Molecules 2023, 28(5), 2249; https://doi.org/10.3390/molecules28052249 - 28 Feb 2023

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Two species within the Lamiaceae (mint) family, Agastache urticifolia and Monardella odoratissima, are aromatic plants that are native to the Intermountain Region (USA). Essential oil produced through steam distillation was examined to establish the essential oil yield and both the achiral and [...] Read more.

Two species within the Lamiaceae (mint) family, Agastache urticifolia and Monardella odoratissima, are aromatic plants that are native to the Intermountain Region (USA). Essential oil produced through steam distillation was examined to establish the essential oil yield and both the achiral and chiral aromatic profiles of both plant species. The resulting essential oils were analyzed by GC/MS, GC/FID, and MRR (molecular rotational resonance). For A. urticifolia and M. odoratissima, achiral essential oil profiles were largely composed of limonene (71.0%, 27.7%), trans-β-ocimene (3.6%, 6.9%), and pulegone (15.9%, 4.3%), respectively. Between the two species, eight chiral pairs were analyzed and, interestingly, the dominant enantiomer (calculated as ee%) of limonene and pulegone switched between the two species. Where enantiopure standards were not commercially available, MRR was used as a reliable analytical technique for chiral analysis. This study verifies the achiral profile for A. urticifolia and, for the first time to the authors’ knowledge, establishes the achiral profile for M. odoratissima and chiral profile for both species. Additionally, this study confirms the utility and practicality of using MRR for determining chiral profiles in essential oils. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Isolation and Characterization of One New Natural Compound with Other Potential Bioactive Secondary Metabolites from Glycosmis cyanocarpa (Blume) Spreng. (Family: Rutaceae)

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Md. Ariful Islam

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Sania Ashrafi

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Khondaker Miraz Rahman

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Shamim Ahmed

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A. H. M. Shofiul Islam Molla Jamal

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Monira Ahsan

Molecules 2023, 28(5), 2207; https://doi.org/10.3390/molecules28052207 - 27 Feb 2023

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Glycosmis cyanocarpa (Blume) Spreng is a plant in the Rutaceae family and a species in the Glycosmis genus that has received little attention. Therefore, this research aimed to report the chemical and biological analysis of Glycosmis cyanocarpa (Blume) Spreng. The chemical analysis involved [...] Read more.

Glycosmis cyanocarpa (Blume) Spreng is a plant in the Rutaceae family and a species in the Glycosmis genus that has received little attention. Therefore, this research aimed to report the chemical and biological analysis of Glycosmis cyanocarpa (Blume) Spreng. The chemical analysis involved the isolation and characterization of secondary metabolites through an extensive chromatographic study, and the structures of these metabolites were elucidated on the basis of a detailed analysis of NMR and HRESIMS spectroscopic data and by comparison with those of related compounds reported in the literature. Different partitions of the crude ethyl acetate (EtOAc) extract were evaluated for antioxidant, cytotoxic, and thrombolytic potentials. In chemical analysis, one new phenyl acetate derivative, namely 3,7,11,15-tetramethylhexadec-2-en-1-yl 2-phenylacetate (1), along with four known compounds N-methyl-3-(methylthio)-N-(2-phenylacetyl) acrylamide (2), penangin (3), β-Caryophyllene oxide (4), and acyclic diterpene-phytol (5) were isolated for the first time from the stem and leaf of the plant. The ethyl acetate fraction showed significant free radical scavenging activity with an IC₅₀ value of 11.536 µg/mL compared to standard ascorbic acid (4.816 µg/mL). In the thrombolytic assay, the dichloromethane fraction showed the maximum thrombolytic activity of 16.42% but was still insignificant compared to the standard streptokinase (65.98%). Finally, in a brine shrimp lethality bioassay, the LC₅₀ values of dichloromethane, ethyl acetate, and aqueous fractions were found to be 0.687 µg/mL, 0.805 µg/mL, and 0.982 µg/mL which are significant compared to the standard vincristine sulfate of 0.272 µg/mL. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Headspace Solid Phase Micro-Extraction of Volatile Constituents Produced from Saudi Ruta chalepensis and Molecular Docking Study of Potential Antioxidant Activity

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Molecules 2023, 28(4), 1891; https://doi.org/10.3390/molecules28041891 - 16 Feb 2023

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Ruta chalepensis L., commonly known as Shazab in Saudi Arabia, is one of the famous culinary plants belonging to the Rutaceae family. It is commonly used in ethnomedicine in treating numerous diseases. This study was performed to characterize the essential oil isolated from [...] Read more.

Ruta chalepensis L., commonly known as Shazab in Saudi Arabia, is one of the famous culinary plants belonging to the Rutaceae family. It is commonly used in ethnomedicine in treating numerous diseases. This study was performed to characterize the essential oil isolated from Saudi species using a relatively new advanced headspace solid-phase microextraction technique. Following that, the antioxidant activity of the extracted oil was assessed using in vitro techniques such as the DPPH and nitric oxide scavenging tests, as well as the reducing power FRAP study and the molecular docking tool. The essential oil yield of the dried plant was 0.83% (v/w). Gas chromatography joined with a mass spectrometer was used to determine the chemical composition of the pale-yellow essential oil. Sixty-eight constituents were detected, representing 97.70% of the total oil content. The major constituents were aliphatic ketones dominated by 2-undecanone (37.30%) and 2-nonanone (20.00%), with minor constituents of mono and sesquiterpenoids chemical classes. Nicotinamide adenine dinucleotide phosphate (NADPH) oxidase is one of the major causes of many contemporary diseases due to its ability to create a reactive oxygen species (ROS). Thus, molecular docking was used to confirm that some oil phytoconstituents have good docking scores compared to the standard antioxidant drug (Vitamin C), indicating great binding compatibility between the (NADPH) oxidase receptor site and the ligand. In conclusion, our findings suggest that the oil could be used safely and as a cost-effective remedy in treating various modern diseases caused by free radical formation. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

The Effect of Fresh Kale (Brassica oleracea var. sabellica) Addition and Processing Conditions on Selected Biological, Physical, and Chemical Properties of Extruded Snack Pellets

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Molecules 2023, 28(4), 1835; https://doi.org/10.3390/molecules28041835 - 15 Feb 2023

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The purpose of this study was to determine the effect of the addition of fresh kale and processing conditions on extruded pellet antioxidant activity and selected physicochemical properties. The results of the applied DPPH, FRAP, and TPC methods indicated that, for both 60 [...] Read more.

The purpose of this study was to determine the effect of the addition of fresh kale and processing conditions on extruded pellet antioxidant activity and selected physicochemical properties. The results of the applied DPPH, FRAP, and TPC methods indicated that, for both 60 and 100 rpm screw speeds, snack pellet antioxidant activity and phenolic content were strongly linked to the fresh kale content, and these properties increased with the addition of this plant. The amount of fresh kale and the applied processing variables (extruder screw speed and the moisture content of the raw material blends) were also found to significantly affect the water absorption index, water solubility index, fat absorption index, fatty acid profile, and basic chemical composition of the obtained extrudates. The sample with the highest phenolic content (72.8 μg GAE/g d.w.), the most advantageous chemical composition (protein, ash, fat, carbohydrates, and fiber content), and high antioxidant properties was produced at a fresh kale content of 30%, a 36% moisture content, and a 100 rpm screw speed. The following phenolic acids were identified in this sample: protocatechuic, 4-OH-benzoic, vanillic, syringic, salicylic, caffeic, coumaric, ferulic, and sinapic. Sinapic acid was the prevailing phenolic acid. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Comprehensive Metabolite Profiling of Berdav Propolis Using LC-MS/MS: Determination of Antioxidant, Anticholinergic, Antiglaucoma, and Antidiabetic Effects

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Hasan Karagecili

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Mustafa Abdullah Yılmaz

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Molecules 2023, 28(4), 1739; https://doi.org/10.3390/molecules28041739 - 11 Feb 2023

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Propolis is a complex natural compound that honeybees obtain from plants and contributes to hive safety. It is rich in phenolic and flavonoid compounds, which contain antioxidant, antimicrobial, and anticancer properties. In this study, the chemical composition and antioxidant activities of propolis were [...] Read more.

Propolis is a complex natural compound that honeybees obtain from plants and contributes to hive safety. It is rich in phenolic and flavonoid compounds, which contain antioxidant, antimicrobial, and anticancer properties. In this study, the chemical composition and antioxidant activities of propolis were investigated; ABTS^•+, DPPH^• and DMPD^•+ were prepared using radical scavenging antioxidant methods. The phenolic and flavonoid contents of propolis were 53 mg of gallic acid equivalent (GAE)/g and 170.164 mg of quercetin equivalent (QE)/g, respectively. The ferric ion (Fe³⁺) reduction, CUPRAC and FRAP reduction capacities were also studied. The antioxidant and reducing capacities of propolis were compared with those of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol and Trolox reference standards. The half maximal inhibition concentration (IC₅₀) values of propolis for ABTS^•+, DPPH^• and DMPD^•+ scavenging activities were found to be 8.15, 20.55 and 86.64 μg/mL, respectively. Propolis extract demonstrated IC₅₀ values of 3.7, 3.4 and 19.6 μg/mL against α-glycosidase, acetylcholinesterase (AChE) and carbonic anhydrase II (hCA II) enzyme, respectively. These enzymes’ inhibition was associated with diabetes, Alzheimer’s disease (AD) and glaucoma. The reducing power, antioxidant activity and enzyme inhibition capacity of propolis extract were comparable to those demonstrated by the standards. Twenty-eight phenolic compounds, including acacetin, caffeic acid, p-coumaric acid, naringenin, chrysin, quinic acid, quercetin, and ferulic acid, were determined by LC-MS/MS to be major organic compounds in propolis. The polyphenolic antioxidant-rich content of the ethanol extract of propolis appears to be a natural product that can be used in the treatment of diabetes, AD, glaucoma, epilepsy, and cancerous diseases. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

New Verticillene Diterpenoids, Eudesmane Sesquiterpenoids, and Hydroperoxysteroids from the Further Chemical Investigation of a Taiwanese Soft Coral Cespitularia sp.

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Molecules 2023, 28(4), 1521; https://doi.org/10.3390/molecules28041521 - 04 Feb 2023

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An investigation of the chemical composition of a Formosan soft coral Cespitularia sp. led to the discovery of one new verticillene-type diterpenoid, cespitulactam M (1); one new eudesmane sesquiterpenoid, cespilamide F (2); and three new hydroperoxysteroids (3– [...] Read more.

An investigation of the chemical composition of a Formosan soft coral Cespitularia sp. led to the discovery of one new verticillene-type diterpenoid, cespitulactam M (1); one new eudesmane sesquiterpenoid, cespilamide F (2); and three new hydroperoxysteroids (3–5) along with twelve known analogous metabolites (6–17). In addition, one new derivative, cespitulactam M-6,2′-diacetate (1a), was prepared from compound 1. The structures were determined by detailed spectroscopic analyses, particularly HRESIMS and NMR techniques. Moreover, the in vitro cytotoxicity, anti-inflammatory, and antibacterial activity of 1–17 and 1a were evaluated. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Anti-Dengue Activity of Lipophilic Fraction of Ocimum basilicum L. Stem

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Molecules 2023, 28(3), 1446; https://doi.org/10.3390/molecules28031446 - 02 Feb 2023

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Ocimum basilicum L. is used to cure many types of fever in traditional medicine. This study aims to explore the antiviral activity of the lipophilic fraction of the stem of O. basilicum (LFOB) against dengue virus (DENV) and chikungunya virus (CHIKV). The LFOB [...] Read more.

Ocimum basilicum L. is used to cure many types of fever in traditional medicine. This study aims to explore the antiviral activity of the lipophilic fraction of the stem of O. basilicum (LFOB) against dengue virus (DENV) and chikungunya virus (CHIKV). The LFOB was analyzed using GC-FID and GC-MS. The antiviral activity of LFOB was studied using the Vero CCL-81 cell line. The cytotoxicity assay was performed using 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT). In vitro antiviral activity and FFU assay were used to determine and confirm antiviral activity against DENV and CHIKV. Twenty-six compounds were identified in LFOB using GC/MS. The most abundant compounds were β-sitosterol (22.9%), stigmasterol (18.7%), and campesterol (12.9%). Significant reduction in DENV titre was observed under pre- and post-infection treatment conditions at a concentration of 3.125 µg/mL, but no anti-CHIKV activity was observed. Our earlier and the present AutoDock-Vina-based in silico docking study revealed that β-sitosterol and stigmasterol could form strong interactions with the DENV E glycoprotein and DENV RdRp domain, respectively. Our findings suggest that LFOB can inhibit DENV infection and might act as a potent prophylactic/therapeutic agent against DENV-2. In silico results suggested that β-sitosterol and stigmasterol may block the viral entry by inhibiting the fusion process and viral replication respectively. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Edible Plant Extracts against Aedes aegypti and Validation of a Piper nigrum L. Ethanolic Extract as a Natural Insecticide

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Lais Silva Morais

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João Paulo Barreto Sousa

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Carolina Melo Aguiar

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Ciro Martins Gomes

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Daniel Pecoraro Demarque

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Lorena Carneiro Albernaz

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Laila Salmen Espindola

Molecules 2023, 28(3), 1264; https://doi.org/10.3390/molecules28031264 - 28 Jan 2023

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Abstract

The Aedes aegypti mosquito significantly impacts public health, with vector control remaining the most efficient means of reducing the number of arboviral disease cases. This study screened the larvicidal and pupicidal activity of common edible plant extracts. Piper nigrum L. (black pepper) extract [...] Read more.

The Aedes aegypti mosquito significantly impacts public health, with vector control remaining the most efficient means of reducing the number of arboviral disease cases. This study screened the larvicidal and pupicidal activity of common edible plant extracts. Piper nigrum L. (black pepper) extract production was optimized using accelerated solvent extraction (ASE) and validated following regulatory requirements using HPLC-PDA analytical methodology to quantify its major component–piperine. Larvicidal activity was determined for the standardized P. nigrum fruit ethanol extract (LC₅₀ 1.1 µg/mL) and piperine standard (LC₅₀ 19.0 µg/mL). Furthermore, 9-day residual activity was determined for the extract (4 µg/mL) and piperine (60 µg/mL), with daily piperine quantification. Semi-field trials of solid extract formulations demonstrated 24-day activity against Ae. aegypti larvae. Thus, the standardized P. nigrum extract emerges as a potential candidate for insecticide development to control the arboviral vector. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Chemical Composition of Essential Oils of Seven Polygonum Species from Turkey: A Chemotaxonomic Approach

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Azize Demirpolat

Molecules 2022, 27(24), 9053; https://doi.org/10.3390/molecules27249053 - 19 Dec 2022

Cited by 2 | Viewed by 1132

Abstract

Medicinal plants and herbal preparations are gaining attention in the scientific community today, as they are often used intermittently in the treatment of various diseases. The genus of Polygonum (Polygonaceae), known locally as “madimak”, is an aromatic plant widely used in world flavors. [...] Read more.

Medicinal plants and herbal preparations are gaining attention in the scientific community today, as they are often used intermittently in the treatment of various diseases. The genus of Polygonum (Polygonaceae), known locally as “madimak”, is an aromatic plant widely used in world flavors. The chemical composition of the essential oils of dried aerial parts of seven of Polygonum was analyzed by GC-MS. These species are Polygonum lapathifolium L., Polygonum persicaria L., Polygonum arenastrum Bor., Polygonum bellardii All., Polygonum arenarium Waldst. Et Kit., Polygonum aviculare L., and Polygonum cognatum Meissn. Qualitative and quantitative differences were found in the essential oil analysis of the seven Polygonum species. The major compounds were determined as (E)-β-farnesene (19. 46%), dodecanal (15.92%), β-caryophyllene (12.95%), in P. aviculare; (E)-β-farnesene (25.00%), dodecanal (20.45%), β-caryophyllene (9.38%), and caryophyllene oxide (8. 26%) in P. persicaria; dodecanal (25.65%), caryophyllene oxide (13.35%), β-caryophyllene (7.95%), and (E)-β-farnesene (6.20%) in P. lapathifolium, and dodecanal (19.65%), (E)-β-farnesene (13.86%), β-caryophyllene (8.06%), and α-terpineol (7.2%) in P. arenarium, dodecanal (16.23%), β-caryophyllene (16.09%), (E)-β-farnesene (12.26%), caryophyllene oxide (7.94%) in P. bellardii, (E)-β-farnesene (20.75%), dodecanal (17.96%), β-caryophyllene (13.01%), α-terpineol (4.97%) in P. arenastrum, (E)-β-farnesene (9.49%), dodecanal (14.01%), β-caryophyllene (11.92%), geranyl acetate (9.49%), and undecanal (7.35%) in P. cognatum. This study is the most comprehensive study conducted to determine the essential oil components of Polygonum species. In addition, a literature review on the composition of the essential oils of these Polygonum taxa was performed. The essential oil components of the species in our study were revealed for the first time with this study. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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UPLC-ESI-QTOF-MS Profiling of Phenolic Compounds from Eriocephalus africanus: In Vitro Antioxidant, Antidiabetic, and Anti-Inflammatory Potentials

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Kunle Okaiyeto

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Nasifu Kerebba

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Oluwafemi O. Oguntibeju

Molecules 2022, 27(24), 8912; https://doi.org/10.3390/molecules27248912 - 15 Dec 2022

Viewed by 640

Abstract

The present study investigated phenolic compounds, antioxidant, antidiabetic, and the anti-inflammatory potentials of methanolic and chloroform extracts of Eriocephalus africanus. The methanolic extract included, polyphenols (112 ± 2.81 mg gallic acid equivalent (GAE)/g), flavonols (76.12 ± 7.95 mg quercetin equivalents (QE)/g); antioxidant [...] Read more.

The present study investigated phenolic compounds, antioxidant, antidiabetic, and the anti-inflammatory potentials of methanolic and chloroform extracts of Eriocephalus africanus. The methanolic extract included, polyphenols (112 ± 2.81 mg gallic acid equivalent (GAE)/g), flavonols (76.12 ± 7.95 mg quercetin equivalents (QE)/g); antioxidant capacity (Ferric Reducing Antioxidant Power (FRAP) (752.64 ± 89.0 μmol of ascorbic acid equivalents (AAE) per g dry weight (µmol AAE/g), 2,2-dyphenyl-1-picrylhydrazyl (DPPH) (812.18 ± 51.12 Trolox equivalents per gram of dry mass of plant extracts (μmol TE/g), TEAC (631.63 ± 17.42 µmol TE/g)), while the chloroform extract included polyphenols (39.93 ± 1.36 mg GAE/g), flavonols (44.81 ± 3.74 mg QE/g); antioxidant capacity, DPPH (58.70 ± 5.18 µmol TE/g), TEAC (118.63 ± 3.74 µmol TE/g) and FRAP (107.10 ± 2.41 µmol AAE/g). The phytochemicals profiling performed by UPLC-ESI-QTOF-MS revealed some important polyphenols, predominantly flavonoids, that could be responsible for the antioxidant capacity and biological effects. Both extracts demonstrated a dose-dependent manner of the alpha-glucosidase inhibition with an IC₅₀ between 125 and 250 μg/mL for methanolic extract, while the chloroform extract was at 250 μg/mL. In the L6 myoblasts and C3A hepatocytes, the methanolic extract slightly increased the utilization of glucose, and both extracts exhibited a dose-dependent increase in the glucose uptake in both cell types without significantly increasing the cytotoxicity. Furthermore, both extracts exhibited an anti-inflammatory potential and the findings from the present study could serve as a baseline for further research in the development of pharmaceutical agents. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

The Chemical Signatures of Water Extract of Zingiber officinale Rosc

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Molecules 2022, 27(22), 7818; https://doi.org/10.3390/molecules27227818 - 13 Nov 2022

Cited by 1 | Viewed by 908

Abstract

Background: Ginger (Z. officinale Rosc.) is a common herb and is widely used as a diet-based or home therapy in traditional medicine worldwide. However, fresh ginger turns into dried ginger after kiln drying and shows a different treatment effect in clinical practice. [...] Read more.

Background: Ginger (Z. officinale Rosc.) is a common herb and is widely used as a diet-based or home therapy in traditional medicine worldwide. However, fresh ginger turns into dried ginger after kiln drying and shows a different treatment effect in clinical practice. Objective: To characterize the changes of major bioactive constituents in dried ginger after the processing of fresh ginger. Methods: A novel, ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UHPLC–QTOF/MS) method was established to characterize the changes in the bioactive constituents of dried ginger. The novel strategy was split into two steps: firstly, the MS selected the most intense precursor ions of tandem MS; then, target MS/MS acquisition with different collision energies (10, 20, and 40 eV) was used to characterize the compound’s accurate MS/MS spectra and compare the MS/MS spectrum with the building MS reference library and reference standards. Result: Fifty-three compounds, including diarylheptanoids, gingerols, gingerodiols, gingerdiones, and shogaol-related compounds, were identified based on summarized fragmentation patterns. Fifteen out of fifty-three compounds were diarylheptanoids, which was different from fresh ginger. Conclusion: These identified compounds could be used to characterize the quality of dried ginger, pharmacologic studies should focus on diarylheptanoids explaining the different treatment effects between fresh ginger and dried ginger. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Multivariate Analysis Revealed Ultrasonic-Assisted Extraction Improves Anti-Melanoma Activity of Non-Flavonoid Compounds in Indonesian Brown Algae Ethanol Extract

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Anggit Listyacahyani Sunarwidhi

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Ari Hernawan

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Andri Frediansyah

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Sri Widyastuti

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Ni Wayan Riyani Martyasari

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Muhammad Syach Maulad Ichfa

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Eka Sunarwidhi Prasedya

Molecules 2022, 27(21), 7509; https://doi.org/10.3390/molecules27217509 - 03 Nov 2022

Cited by 2 | Viewed by 1003

Abstract

Indonesia has high biodiversity of algae that are under-utilised due to limitations in the processing techniques. Here, we observed the effect of two different extraction methods (cold maceration and ultrasonic-assisted extraction (UAE)) on multiple variables of Indonesian brown algae ethanol extracts (Sargassum [...] Read more.

Indonesia has high biodiversity of algae that are under-utilised due to limitations in the processing techniques. Here, we observed the effect of two different extraction methods (cold maceration and ultrasonic-assisted extraction (UAE)) on multiple variables of Indonesian brown algae ethanol extracts (Sargassum polycystum, Sargassum cristaefolium, Sargassum aquifolium and Turbinaria ornata). The variables observed included metabolites screening by untargeted metabolomics liquid chromatography-high-resolution mass spectrometry (LC-HRMS), observation of total phenolic content (TPC), total flavonoid content (TFC), anti-oxidant and B16-F10 melanoma cells cytotoxicity. UAE extracts had higher extraction yield and TPC, but no TFC difference was observed. UAE extract had more lipophilic compounds, such as fatty acids (Palmitic acid, Oleamide, Palmitoleic acid, Eicosapentaenoic acid, α-Linolenic acid, Arachidonic acid), lipid-derived mediators (11,12-Epoxyeicosatrienoic acid ((±)11(12)-EET)), steroid derivatives (Ergosterol peroxide), lipophilic metabolite (Fucoxanthin), and lipid-soluble vitamins (all-trans-retinol). Principle component analysis (PCA) revealed that TPC, not TFC, in the UAE extracts was correlated with the anti-oxidant activities and cytotoxicity of the extracts towards B16-F10 melanoma cells. This means other non-flavonoid phenolic and lipophilic compounds may have contributed to its bioactivity. These results suggest that out of the two methods investigated, UAE could be a chosen method to extract natural anti-melanogenic agents from brown algae. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Design and Synthesis of Coumarin Derivatives as Cytotoxic Agents through PI3K/AKT Signaling Pathway Inhibition in HL60 and HepG2 Cancer Cells

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Molecules 2022, 27(19), 6709; https://doi.org/10.3390/molecules27196709 - 09 Oct 2022

Viewed by 1196

Abstract

In this study, a series of coumarin derivatives, either alone or as hybrids with cinnamic acid, were synthesized and evaluated for their cytotoxicity against a panel of cancer cells using the MTT assay. Then, the most active compounds were inspected for their mechanism [...] Read more.

In this study, a series of coumarin derivatives, either alone or as hybrids with cinnamic acid, were synthesized and evaluated for their cytotoxicity against a panel of cancer cells using the MTT assay. Then, the most active compounds were inspected for their mechanism of cytotoxicity by cell-cycle analysis, RT-PCR, DNA fragmentation, and Western blotting techniques. Cytotoxic results showed that compound (4) had a significant cytotoxic effect against HL60 cells (IC₅₀ = 8.09 µM), while compound (8b) had a noticeable activity against HepG2 cells (IC₅₀ = 13.14 µM). Compounds (4) and (8b) mediated their cytotoxicity via PI3K/AKT pathway inhibition. These results were assured by molecular docking studies. These results support further exploratory research focusing on the therapeutic activity of coumarin derivatives as cytotoxic agents. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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An Investigation of the Anti-Depressive Properties of Phenylpropanoids and Flavonoids in Hemerocallis citrina Baroni

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Molecules 2022, 27(18), 5809; https://doi.org/10.3390/molecules27185809 - 08 Sep 2022

Cited by 2 | Viewed by 912

Abstract

The World Health Organization predicts that over the next several years, depression will become the most important mental health issue globally. Growing evidence shows that the flower buds of Hemerocallis citrina Baroni (H. citrina) possess antidepressant properties. In the search for [...] Read more.

The World Health Organization predicts that over the next several years, depression will become the most important mental health issue globally. Growing evidence shows that the flower buds of Hemerocallis citrina Baroni (H. citrina) possess antidepressant properties. In the search for new anti-depression drugs, a total of 15 phenylpropanoids and 22 flavonoids were isolated and identified based on spectral data (1D and 2D NMR, HR-ESI-MS, UV) from H. citrina. Among them, compound 8 was a novel compound, while compounds 1–4, 6, 9, 10, 15, 17, 24–26, 28, and 37 were isolated for the first time from Hemerocallis genus. To study the antidepressant activity of phenylpropanoids and flavonoids fractions from H. citrina, macroporous resin was used to enrich them under the guidance of UV characteristics. UHPLC-MS/MS was applied to identify the constituents of the enriched fractions. According to behavioral tests and biochemical analyses, it showed that phenylpropanoid and flavonoid fractions from H. citrina can improve the depressive-like mental state of chronic unpredictable mild stress (CUMS) rats. This might be accomplished by controlling the amounts of the inflammatory proteins IL-6, IL-1β, and TNF-α in the hippocampus as well as corticosterone in the serum. Thus, the monomer compounds were tested for their anti-neuroinflammatory activity and their structure–activity relationship was discussed in further detail. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Chemical Characterization and Nutritional Markers of South African Moringa oleifera Seed Oils

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Molecules 2022, 27(18), 5749; https://doi.org/10.3390/molecules27185749 - 06 Sep 2022

Cited by 2 | Viewed by 1057

Abstract

Moringa oleifera Lam (syn. M. ptreygosperma Gaertn.) leaves are globally acclaimed for their nutritional content and mitigation of malnutrition. In most impoverished rural communities including Limpopo, Mpumalanga and KwaZulu Natal of South Africa, powdered leaves of Moringa oleifera are applied as a [...] Read more.

Moringa oleifera Lam (syn. M. ptreygosperma Gaertn.) leaves are globally acclaimed for their nutritional content and mitigation of malnutrition. In most impoverished rural communities including Limpopo, Mpumalanga and KwaZulu Natal of South Africa, powdered leaves of Moringa oleifera are applied as a nutritional supplement for readily available food such as porridge for malnourished children and even breast-feeding mothers. Widely practiced and admired is also the use of the plant seed in the do-it-yourself purification of water by rural South Africans. This study aimed at identifying the chemical and nutritional marker compounds present in South African Moringa oleifera seed oils using high resolution 1-2-dimension gas chromatography in order to give scientific validation to its uses in cosmetics and particularly in culinary practices. Results obtained from two-dimension tandem mass spectrometry chemical signature revealed over 250 compounds, five times more than those reported from one-dimension gas chromatography. Whereas previous reports from gas chromatography-mass spectrometry analysis reported oleic acid (70–78%) as the major compound from oil samples from other countries, M. oleifera seed oil from South Africa is marked by cis-13-octadeaconic acid with 78.62% and 41.9% as the predominant monounsaturated fatty acid in the hexane and dichloromethane extracts respectively. This was followed by cis-vaccenic acid, an isomer of oleic acid at 51% in the acetone extract, 9-octadecanoic acid-(z)-methyl ester at 39.18%, 21.34% and 10.06% in dichloromethane, hexane and acetone extracts respectively. However, a principal component analysis with R² = 0.98 of the two-dimension tandem mass spectrometry cum chemometric analysis indicated n-hexadecanoic acid, oleic acid, 9-octadecanoic acid-(z)-methyl ester and cis-vaccenic acid with a probability of 0.96, 0.88, 0.80 and 0.79 respectively as the marker compounds that should be used for the quality control of moringa seed oils from South Africa. This study demonstrates that South African Moringa oleifera oils contain C-18 monounsaturated fatty acids similar to oils from Egypt (76.2%), Thailand (71.6%) and Pakistan (78.5%) just to mention but a few. These fatty acids are sunflower and olive oil type-compounds and therefore place moringa seed oil for consideration as a cooking oil amongst its other uses. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Chemistry and Bioactivity of Microsorum scolopendria (Polypodiaceae): Antioxidant Effects on an Epithelial Damage Model

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Cristóbal Balada

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Valentina Díaz

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Mónica Castro

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Macarena Echeverría-Bugueño

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María José Marchant

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Leda Guzmán

Molecules 2022, 27(17), 5467; https://doi.org/10.3390/molecules27175467 - 25 Aug 2022

Viewed by 1044

Abstract

Microsorum scolopendia (MS), which grows on the Chilean island of Rapa Nui, is a medicinal fern used to treat several diseases. Despite being widely used, this fern has not been deeply investigated. The aim of this study was to perform a [...] Read more.

Microsorum scolopendia (MS), which grows on the Chilean island of Rapa Nui, is a medicinal fern used to treat several diseases. Despite being widely used, this fern has not been deeply investigated. The aim of this study was to perform a characterization of the polyphenolic and flavonoid identity, radical scavenging, antimicrobial, and anti-inflammatory properties of MS rhizome and leaf extracts (RAE and HAE). The compound identity was analyzed through the reversed-phase high-performance liquid chromatography (RP-HPLC) method coupled with mass spectrometry. The radical scavenging and anti-inflammatory activities were evaluated for DPPH, ORAC, ROS formation, and COX inhibition activity assay. The antimicrobial properties were evaluated using an infection model on Human Dermal Fibroblast adult (HDFa) cell lines incubated with Staphylococcus aureus and Staphylococcus epidermidis. The most abundant compounds were phenolic acids between 46% to 57% in rhizome and leaf extracts, respectively; followed by flavonoids such as protocatechic acid 4-O-glucoside, cirsimaritin, and isoxanthohumol, among others. MS extract inhibited and disaggregated the biofilm bacterial formed and showed an anti-inflammatory selective property against COX-2 enzyme. RAE generated a 64% reduction of ROS formation in the presence of S. aureus and 87.35% less ROS in the presence of S. epidermidis on HDFa cells. MS has great therapeutic potential and possesses several biological properties that should be evaluated. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Sesquiterpenoids from Inula britannica and Their Potential Effects against Triple-Negative Breast Cancer Cells

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Molecules 2022, 27(16), 5230; https://doi.org/10.3390/molecules27165230 - 16 Aug 2022

Cited by 1 | Viewed by 997

Abstract

Flowers of Inula britannica commercially serve as pharmaceutical herbs in the manufacturing of medicinal products. In the current study, sesquiterpenoids of I. britannica flowers’ extract and their potential effects against triple-negative breast cancer (TNBC) cells were investigated. Eight structurally diverse sesquiterpenoids, including one [...] Read more.

Flowers of Inula britannica commercially serve as pharmaceutical herbs in the manufacturing of medicinal products. In the current study, sesquiterpenoids of I. britannica flowers’ extract and their potential effects against triple-negative breast cancer (TNBC) cells were investigated. Eight structurally diverse sesquiterpenoids, including one sesquiterpenoid dimer (1) and seven sesquiterpenoid monomers (2–8) were isolated from this source. The structures of all compounds were elucidated by 1D/2D NMR data, and their absolute configurations were discerned by single crystal X-ray diffraction. All of the compounds were tested for their potential effects against TNBC. Specifically, 5 displayed strong antiproliferative potency against TNBC cells with a high selective index (SI) on MCF-7 cells (SI > 4 of IC₅₀ on MDA-MB-468/IC₅₀ on MCF-7), and dimer 1 (IC₅₀ = 8.82 ± 0.85 μM) showed better antiproliferative potency against MCF-7 cells than the other monomers did (2–8) (IC₅₀ > 20 μM). To our best knowledge, compound 5 is the first sesquiterpenoid targeting TNBC cells. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Structural Characterization of a Polygonatum cyrtonema Hua Tuber Polysaccharide and Its Contribution to Moisture Retention and Moisture-Proofing of Porous Carbohydrate Material

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Molecules 2022, 27(15), 5015; https://doi.org/10.3390/molecules27155015 - 06 Aug 2022

Cited by 2 | Viewed by 1193

Abstract

Porous carbohydrate materials such as tobacco shreds readily absorb moisture and become damp during processing, storage, and consumption (smoking). Traditional humectants have the ability of moisture retention but moisture-proofing is poor. Polygonatum cyrtonema Hua polysaccharide (PCP 85−1−1) was separated by fractional precipitation and [...] Read more.

Porous carbohydrate materials such as tobacco shreds readily absorb moisture and become damp during processing, storage, and consumption (smoking). Traditional humectants have the ability of moisture retention but moisture-proofing is poor. Polygonatum cyrtonema Hua polysaccharide (PCP 85−1−1) was separated by fractional precipitation and was purified by anion exchange and gel permeation chromatography. The average molecular weight (Mw) of PCP 85−1−1 was 2.88 × 10³ Da. The monosaccharide composition implied that PCP 85−1−1 consisted of fucose, glucose, and fructose, and the molar ratio was 22.73:33.63:43.65. When 2% PCP 85−1−1 was added to tobacco shreds, the ability of moisture retention and moisture-proofing were significantly enhanced. The moisture retention index (MRI) and moisture-proofing index (MPI) increased from 1.95 and 1.67 to 2.11 and 2.14, respectively. Additionally, the effects of PCP 85−1−1 on the aroma and taste of tobacco shreds were evaluated by electronic tongue and gas chromatography–mass spectrometry (GC-MS). These results indicated that PCP 85−1−1 had the characteristics of preventing water absorption under high relative humidity and moisturizing under dry conditions. The problem that traditional humectants are poorly moisture-proof was solved. PCP 85−1−1 can be utilized as a natural humectant on porous carbohydrates, which provides a reference for its development and utilization. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Structural Characteristics, Antioxidant, and Immunostimulatory Activities of an Acidic Polysaccharide from Raspberry Pulp

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Molecules 2022, 27(14), 4385; https://doi.org/10.3390/molecules27144385 - 08 Jul 2022

Cited by 3 | Viewed by 872

Abstract

The extraction and characterization of new bioactive plant-derived polysaccharides with the potential for use as functional foods and medicine have attracted much attention. In the present study, A novel acidic polysaccharide (RPP-3a) with a weight-average molecular weight (Mw) of 88,997 Da was isolated [...] Read more.

The extraction and characterization of new bioactive plant-derived polysaccharides with the potential for use as functional foods and medicine have attracted much attention. In the present study, A novel acidic polysaccharide (RPP-3a) with a weight-average molecular weight (Mw) of 88,997 Da was isolated from the raspberry pulp. RPP-3a was composed of rhamnose, arabinose, galactose, glucose, mannose, and galacturonic acid at a molar ratio of 13.1:28.6:16.8:1.4:6.2:33.9. Structural analysis suggested that the RPP-3a backbone was composed of repeating units of →4)-β-Galp-(1→3,4)-α-Rhap-(1→[4)-α-GalAp-(1→4)-α-GalAp-(1→]_n with branches at the C-4 position of rhamnose. The side chain of RPP-3a, containing two branch levels, was comprised of α-Araf-(1→, →5)-α-Araf-(1→, →3,5)-α-Araf-(1→, →3)-β-Galp-(1→, →3,6)-β-Galp-(1→, →4)-β-Glcp-(1→, and →2,6)-α-Manp-1→ residues. RPP-3a exhibited moderate reducing power and strong hydroxyl and superoxide anion radical scavenging abilities. RPP-3a significantly promoted the viability of RAW264.7 macrophages by increasing the production of nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1β (IL-1β) at both the expression and transcriptional levels. In summary, the immunostimulatory and antioxidant activities make RPP-3a a viable candidate as a health-beneficial functional dietary supplement. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Ultrasound-Assisted Extraction of Anthocyanins from Malus ‘Royalty’ Fruits: Optimization, Separation, and Antitumor Activity

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Molecules 2022, 27(13), 4299; https://doi.org/10.3390/molecules27134299 - 04 Jul 2022

Cited by 2 | Viewed by 1249

Abstract

Red Malus ‘Royalty’ fruits are rich in anthocyanins. This study aimed to obtain the optimal parameters for the extraction and separation of anthocyanins from Malus ‘Royalty’ fruits and to evaluate the inhibitory effect of the enriched anthocyanin fraction on gastric cancer cells. Ultrasonic-assisted [...] Read more.

Red Malus ‘Royalty’ fruits are rich in anthocyanins. This study aimed to obtain the optimal parameters for the extraction and separation of anthocyanins from Malus ‘Royalty’ fruits and to evaluate the inhibitory effect of the enriched anthocyanin fraction on gastric cancer cells. Ultrasonic-assisted extraction was used for the extraction of the anthocyanins of Malus ‘Royalty’ fruit, and the extraction results showed that the optimum parameters were an extraction temperature of 20 °C, a solid–liquid ratio of 1:6 (g/mL), ethanol and formic acid contents of 70% and 0.4%, respectively, an extraction time of 40 min, and an ultrasonic power of 300 W. The optimum extraction parameters to achieve the highest anthocyanin yield by a single-factor experiment coupled with response surface methodology were identified. The separation results showed that the AB-8 macroporous resin was a better purifying material, with 60% ethanol as an adsorbent, and the adsorption–desorption equilibrium times were 6 h and 1 h, respectively. Cyanidin-3-galactoside was the main body composition separation of anthocyanins by a high-performance liquid chromatography-diode array detector. The antitumor activity results showed that the anthocyanins of Malus ‘Royalty’ fruits have a significant inhibitory effect on the gastric cancer cell line BGC-803. The in vitro cell viability test of CCK-8 showed that the inhibitory effect on tumor cells was more significant with the increased anthocyanin concentration, with a half maximal inhibitory concentration (IC₅₀) value of 105.5 μg/mL. The cell morphology was observed by an inverted microscope, and it was found that the backbone of BGC-803 treated with a high concentration of anthocyanins was disintegrated and the nucleoplasm was concentrated. The mechanism of apoptosis was analyzed by Western blotting, and the results showed that with increasing anthocyanin concentration in the medium, the expression levels of the proapoptotic proteins Bax and Bak increased, and the expression levels of the antiapoptotic proteins Bcl-2 and Bcl-xL decreased, which coordinated the regulation of cell apoptosis. This research suggests that the enriched anthocyanin fraction from Malus ‘Royalty’ fruits have potential antitumor and adjuvant therapeutic effects on gastric cancer. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Chemical Composition, Anti-Breast Cancer Activity and Extraction Techniques of Ent-Abietane Diterpenoids from Euphorbia fischeriana Steud

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Molecules 2022, 27(13), 4282; https://doi.org/10.3390/molecules27134282 - 03 Jul 2022

Cited by 2 | Viewed by 1060

Abstract

Ent-abietane diterpenoids are the main active constituents of Euphorbia fischeriana. In the continuing search for new anti-breast cancer drugs, 11 ent-abietane diterpenoids (1–11) were isolated from E. fischeriana. The structures of these compounds were clearly elucidated on [...] Read more.

Ent-abietane diterpenoids are the main active constituents of Euphorbia fischeriana. In the continuing search for new anti-breast cancer drugs, 11 ent-abietane diterpenoids (1–11) were isolated from E. fischeriana. The structures of these compounds were clearly elucidated on the basis of 1D and 2D NMR spectra as well as HRESIMS data. Among them, compound 1 was a novel compound, compound 10 was isolated from Euphorbia genus for the first time, compound 11 was firstly discovered from E. fischeriana. These compounds exhibited varying degrees of growth inhibition against the MCF-10A, MCF-7, ZR-75-1 and MDA-MB-231 cell lines in vitro. The experimental data obtained permit us to identify the roles of the epoxy group, hydroxyl group and acetoxyl group on their cytotoxic activities. Extraction is an important means for the isolation, identification, and application of valuable compounds from natural plants. To maximize yields of ent-abietane diterpenoids of E. fischeriana, 17-hydroxyjolkinolide B, jolkinolide B, 17-hydroxyjolkinolide A and jolkinolide A were selected as quality controls to optimize the salting-out-assisted liquid–liquid extraction (SALLE) by response surface methodology (RSM). The optimized conditions for SALLE were 0.47 g sodium dihydrogen phosphate, 5.5 mL acetonitrile and 4.5 mL water at pH 7.5. The experimental values of 17-hydroxyjolkinolide B, jolkinolide B, 17-hydroxyjolkinolide A and jolkinolide A (2.134, 0.529, 0.396, and 0.148 mg/g, respectively) were in agreement with the predicted values, thus demonstrating the appropriateness of the model. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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GC-MS/MS Quantification of EGFR Inhibitors, β-Sitosterol, Betulinic Acid, (+) Eriodictyol, (+) Epipinoresinol, and Secoisolariciresinol, in Crude Extract and Ethyl Acetate Fraction of Thonningia sanguinea

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Abdulrahman M. Alahdal

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Reda F. A. Abdelhameed

Molecules 2022, 27(13), 4109; https://doi.org/10.3390/molecules27134109 - 26 Jun 2022

Cited by 2 | Viewed by 1071

Abstract

Medicinal plants are widely used in folk medicine to treat various diseases. Thonningia sanguinea Vahl is widespread in African traditional medicine, and exhibits antioxidant, antibacterial, antiviral, and anticancer activities. T. sanguinea is a source of phytomedicinal agents that have previously been isolated and [...] Read more.

Medicinal plants are widely used in folk medicine to treat various diseases. Thonningia sanguinea Vahl is widespread in African traditional medicine, and exhibits antioxidant, antibacterial, antiviral, and anticancer activities. T. sanguinea is a source of phytomedicinal agents that have previously been isolated and structurally elucidated. Herein, gas chromatography combined with tandem mass spectrometry (GC-MS/MS) was used to quantify epipinoresinol, β-sitosterol, eriodictyol, betulinic acid, and secoisolariciresinol contents in the methanolic crude extract and its ethyl acetate fraction for the first time. The ethyl acetate fraction was rich in epipinoresinol, eriodictyol, and secoisolariciresinol at concentrations of 2.3, 3.9, and 2.4 mg/g of dry extract, respectively. The binding interactions of these compounds with the epidermal growth factor receptor (EGFR) were computed using a molecular docking study. The results revealed that the highest binding affinities for the EGFR signaling pathway were attributed to eriodictyol and secoisolariciresinol, with good binding energies of −19.93 and −16.63 Kcal/mol, respectively. These compounds formed good interactions with the key amino acid Met 769 as the co-crystallized ligand. So, the ethyl acetate fraction of T. sanguinea is a promising adjuvant therapy in cancer treatments. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Phytochemical Investigation of Cordia africana Lam. Stem Bark: Molecular Simulation Approach

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Molecules 2022, 27(13), 4039; https://doi.org/10.3390/molecules27134039 - 23 Jun 2022

Cited by 1 | Viewed by 1048

Abstract

Background: The current work planned to evaluate Cordia africana Lam. stem bark, a traditionally used herb in curing of different ailments in Africa such as gastritis and wound infections, based on phytochemical and antibacterial studies of two pathogenic microorganisms: methicillin-resistant Staphylococcus aureus (MRSA) [...] Read more.

Background: The current work planned to evaluate Cordia africana Lam. stem bark, a traditionally used herb in curing of different ailments in Africa such as gastritis and wound infections, based on phytochemical and antibacterial studies of two pathogenic microorganisms: methicillin-resistant Staphylococcus aureus (MRSA) and Helicobacter pylori. Methods: High performance liquid chromatography (HPLC) profiling was used for qualitative and quantitative investigation of the ethanol extract. The minimum inhibitory concentration (MIC) of the ethanolic extract and isolated compounds was estimated using the broth microdilution method and evidenced by molecular dynamics simulations. Results: Four compounds were isolated and identified for the first time: α-amyrin, β-sitosterol, rosmarinic acid (RA) and methyl rosmarinate (MR). HPLC analysis illustrated that MR was the dominant phenolic acid. MR showed the best bacterial inhibitory activity against MRSA and H. pylori with MIC 7.81 ± 1.7 μg/mL and 31.25 ± 0.6, respectively, when compared to clarithromycin and vancomycin, respectively. Conclusion: The antibacterial activity of the stem bark of Cordia africana Lam. was evidenced against MRSA and H. pylori. Computational modeling of the studied enzyme-ligands systems reveals that RA and MR can potentially inhibit both MRSA peptidoglycan transpeptidases and H. pylori urease, thereby creating a pathway via the use of a double target approach in antibacterial treatment. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Structural Characterization and In-Vitro Antioxidant and Immunomodulatory Activities of Polysaccharide Fractions Isolated from Artemisia annua L.

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Lin Zhang

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Narsimha Reddy

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Cheang Soo Khoo

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Sundar Rao Koyyalamudi

Molecules 2022, 27(11), 3643; https://doi.org/10.3390/molecules27113643 - 06 Jun 2022

Cited by 4 | Viewed by 1322

Abstract

Arimisia annua L. is an important anticancer herb used in traditional Chinese medicine. The molecular basis underpinning the anticancer activity is complex and not fully understood, but the herbal polysaccharides, broadly recognised as having immunomodulatory, antioxidant and anticancer activities, are potential key active [...] Read more.

Arimisia annua L. is an important anticancer herb used in traditional Chinese medicine. The molecular basis underpinning the anticancer activity is complex and not fully understood, but the herbal polysaccharides, broadly recognised as having immunomodulatory, antioxidant and anticancer activities, are potential key active agents. To examine the functions of polysaccharides from A. annua, their immunomodulatory and antioxidant potentials were evaluated, as well as their structural characterization. The water-soluble polysaccharides (AAPs) were fractionated using size-exclusion chromatography to obtain three dominant fractions, AAP-1, AAP-2 and AAP-3, having molecular masses centered around 1684, 455 and 5.8kDa, respectively. The antioxidant potentials of the isolated polysaccharides were evaluated by measuring radical scavenging activities against DPPH^● (2,2-diphenyl-1-picrylhydrazyl radical), ABTS^●+ (2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid radical ion), and the OH^● (hydroxyl radical). AAP-1 displayed high antioxidant activities against these radicals, which were 68%, 73% and 78%, respectively. AAP-2 displayed lower scavenging activities than the other two fractions. Immunostimulatory activities of AAPs were measured using mouse macrophages. The three polysaccharide fractions displayed significant antioxidant activities and stimulated the production of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6). AAP-1 showed significant immunostimulatory activity (16-fold increase in the production of IL-6 compared to the control and 13-fold increase in the production of TNF-α) with low toxicity (>60% cell viability at 125 μg/mL concentration). Preliminary structural characterization of the AAPs was carried out using gas chromatography (GC) and FTIR techniques. The results indicate that AAP-1 and AAP-2 are pyranose-containing polysaccharides with β-linkages, and AAP-3 is a β-fructofuranoside. The results suggest that these polysaccharides are potential candidates for immunotherapy and cancer treatment. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Investigation of Chemical Compositions and Biological Activities of Mentha suaveolens L. from Saudi Arabia

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Bashayr Aldogman

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Hallouma Bilel

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Shaima Mohamed Nabil Moustafa

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Khaled F. Elmassary

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Hazim M. Ali

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Faddaa Qayid Alotaibi

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Mohamed Hamza

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Mohamed A. Abdelgawad

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Ahmed H. El-Ghorab

Molecules 2022, 27(9), 2949; https://doi.org/10.3390/molecules27092949 - 05 May 2022

Cited by 3 | Viewed by 1169

Abstract

Mentha is an aromatic plant used since antiquity for its pharmaceutical virtues. The climate of Saudi Arabia favors the growth of aromatic plants including Mentha suaveolens L. The aim of this study is to analyze the volatile oils of different parts of fresh [...] Read more.

Mentha is an aromatic plant used since antiquity for its pharmaceutical virtues. The climate of Saudi Arabia favors the growth of aromatic plants including Mentha suaveolens L. The aim of this study is to analyze the volatile oils of different parts of fresh and dried Mentha suaveolens L. grown in Saudi Arabia (Aljouf area) using Gas Chromatography/Mass Spectrometry (GC/MS) and Gas Chromatography Flame Ionization Detector (GC/FID) techniques, to recognize the effect of drying on chemical composition, then to evaluate the antioxidant and antifungal activities of different extracts. In total, 118 compounds were identified via GC/MS and GC/FID, in which carvone is the main volatile constituent (stems, leaves, whole plant 45–64%). This investigation deduces that Mentha belonged to the carvone chemotype. Then, the analysis of non-volatile constituents of fresh and dried Mentha was performed by HPLC. The main phenolic compound of fresh and dried Mentha for different parts was rosmarinic acid (ranging from 28,002.5 to 6558 µg/g). The ethanolic extract of fresh stem showed the highest antifungal activity (53% inhibition) compared with miconazole (60% inhibition) but the ethanoic extract of dry stem showed no activity. Additionally, all ethanolic extracts, whether for fresh or dry Mentha, have antioxidant activity more than 90% while the antioxidant activity of whole plant volatile oil is equal to 53.33%. This research shows that M. suaveolens L. could be applied to manufacture natural antioxidants, antifungal, and flavoring agents. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

The Potential Role of Nigella sativa Seed Oil as Epigenetic Therapy of Cancer

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Molecules 2022, 27(9), 2779; https://doi.org/10.3390/molecules27092779 - 27 Apr 2022

Cited by 2 | Viewed by 1612

Abstract

Nigella sativa oil, commonly known as black seed oil (BSO), is a well-known Mediterranean food, and its consumption is associated with beneficial effects on human health. A large number of BSO’s therapeutic properties is attributed to its pharmacologically active compound, thymoquinone (TQ), which [...] Read more.

Nigella sativa oil, commonly known as black seed oil (BSO), is a well-known Mediterranean food, and its consumption is associated with beneficial effects on human health. A large number of BSO’s therapeutic properties is attributed to its pharmacologically active compound, thymoquinone (TQ), which inhibits cell proliferation and induces apoptosis by targeting several epigenetic players, including the ubiquitin-like, containing plant homeodomain (PHD) and an interesting new gene, RING finger domains 1 (UHRF1), and its partners, DNA methyltransferase 1 (DNMT1) and histone deacetylase 1 (HDAC1). This study was designed to compare the effects of locally sourced BSO with those of pure TQ on the expression of the epigenetic complex UHRF1/DNMT1/HDAC1 and the related events in several cancer cells. The gas chromatographs obtained from GC-MS analyses of extracted BSO showed that TQ was the major volatile compound. BSO significantly inhibited the proliferation of MCF-7, HeLa and Jurkat cells in a dose-dependent manner, and it induced apoptosis in these cell lines. BSO-induced inhibitory effects were associated with a significant decrease in mRNA expression of UHRF1, DNMT1 and HDAC1. Molecular docking and MD simulation showed that TQ had good binding affinity to UHRF1 and HDAC1. Of note, TQ formed a stable metal coordinate bond with zinc tom, found in the active site of the HDAC1 protein. These findings suggest that the use of TQ-rich BSO represents a promising strategy for epigenetic therapy for both solid and blood tumors through direct targeting of the trimeric epigenetic complex UHRF1/DNMT1/ HDAC1. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

A New Xanthone Glycoside from Mangifera indica L.: Physicochemical Properties and In Vitro Anti-Skin Aging Activities

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Molecules 2022, 27(9), 2609; https://doi.org/10.3390/molecules27092609 - 19 Apr 2022

Cited by 6 | Viewed by 1371

Abstract

A new xanthone glycoside, 1,3,5,6-tetrahydroxyxanthone-C-4-β-d-glucopyranoside was isolated from the methanol extract of Mangifera indica leaves (Anacardiaceae) growing in Egypt. The structure was clarified by 1D and 2D-NMR spectroscopic data. The physicochemical properties of the compound such as lipophilicity, solubility, and formulation [...] Read more.

A new xanthone glycoside, 1,3,5,6-tetrahydroxyxanthone-C-4-β-d-glucopyranoside was isolated from the methanol extract of Mangifera indica leaves (Anacardiaceae) growing in Egypt. The structure was clarified by 1D and 2D-NMR spectroscopic data. The physicochemical properties of the compound such as lipophilicity, solubility, and formulation considerations were predicted via in silico ADMET technique using the SwissADME server. This technique provided Lipinski’s rule of five, such as GIT absorption, distribution, metabolism, and skin permeation. The in vitro inhibitory activities against aging-mediated enzymes such as collagenase, elastase, hyaluronidase, and tyrosinase were assessed. The compound exhibited remarkable anti-collagenase, anti-elastase, anti-hyaluronidase, and anti-tyrosinase effects with IC₅₀ values of 1.06, 419.10, 1.65, and 0.48 µg/mL, respectively, compared to the positive control. The compound showed promising predicted aqueous solubility and reasonable skin penetration suggesting the suitability of the compound for topical formulation as an anti-aging agent for cosmetic preparations. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

In Vitro Anti-Inflammatory Activity of Cotula anthemoides Essential Oil and In Silico Molecular Docking of Its Bioactives

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Reda F. A. Abdelhameed

Molecules 2022, 27(6), 1994; https://doi.org/10.3390/molecules27061994 - 19 Mar 2022

Cited by 5 | Viewed by 1556

Abstract

The genus Cotula (Asteraceae) comprises about 80 species, amongst them Cotula anthemoides L. It is a wild plant growing in Egypt that possesses many traditional uses as a headache, colic, and chest cold remedy. In our study, the chemical composition of C. [...] Read more.

The genus Cotula (Asteraceae) comprises about 80 species, amongst them Cotula anthemoides L. It is a wild plant growing in Egypt that possesses many traditional uses as a headache, colic, and chest cold remedy. In our study, the chemical composition of C. anthemoides essential oils was analyzed using GC-MS spectroscopy. Sixteen components of leave and stem oils and thirteen components of flower oils were characterized. The main components in both essential oil parts were camphor (88.79% and 86.45%) and trans-thujone (5.14% and 10.40%) in the leaves and stems and the flowers, respectively. The anti-inflammatory activity of the oils in lipopolysaccharide-stimulated RAW 264.7 macrophage cells was evaluated. The flower oil showed its predominant effect in the amelioration of proinflammatory cytokines and tumor necrosis factor-α, as well as cyclooxygenase-2. The bornyl acetate showed the highest affinity for the cyclooxygenase-2 receptor, while compound cis-p-menth-2-ene-1-ol had the best affinity for the tumor necrosis factor receptor, according to the results of molecular docking. In addition, the molecule cis-β-farnesene showed promising dual affinity for both studied receptors. Our findings show that essential oils from C. anthemoides have anti-inflammatory properties through their control over the generation of inflammatory mediators. These findings suggest that C. anthemoides essential oils could lead to the discovery of novel sources of anti-inflammatory treatments. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Phytochemical Insights into Ficus sur Extracts and Their Biological Activity

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Elwira Sieniawska

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Łukasz Świątek

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Kouadio Ibrahime Sinan

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Gokhan Zengin

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Anastazja Boguszewska

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Małgorzata Polz-Dacewicz

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Nabeelah Bibi Sadeer

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Ouattara Katinan Etienne

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Mohamad Fawzi Mahomoodally

Molecules 2022, 27(6), 1863; https://doi.org/10.3390/molecules27061863 - 13 Mar 2022

Cited by 3 | Viewed by 2050

Abstract

This study focused on the biological evaluation and chemical characterisation of Ficus sur Forssk. (F. sur) (Family: Moraceae). The methanolic and aqueous extracts’ phytochemical profile, antioxidant, and enzyme inhibitory properties were investigated. The aqueous stem bark extract yielded the highest phenolic [...] Read more.

This study focused on the biological evaluation and chemical characterisation of Ficus sur Forssk. (F. sur) (Family: Moraceae). The methanolic and aqueous extracts’ phytochemical profile, antioxidant, and enzyme inhibitory properties were investigated. The aqueous stem bark extract yielded the highest phenolic content (115.51 ± 1.60 mg gallic acid equivalent/g extract), while the methanolic leaves extract possessed the highest flavonoid content (27.47 ± 0.28 mg Rutin equivalent/g extract). In total, 118 compounds were identified in the tested extracts. The methanolic stem bark extract exhibited the most potent radical scavenging potential against 2,2-diphenyl-1 picrylhydrazyl and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (475.79 ± 6.83 and 804.31 ± 4.52 mg Trolox equivalent/g extract, respectively) and the highest reducing Cu²⁺ capacity (937.86 ± 14.44 mg Trolox equivalent/g extract). The methanolic stem bark extract substantially depressed tyrosinase (69.84 ± 0.35 mg kojic acid equivalent/g extract), α-amylase (0.77 ± 0.01 mmol acarbose equivalent/g extract), acetylcholinesterase and butyrylcholinesterase (2.91 ± 0.07 and 6.56 ± 0.34 mg galantamine equivalent/g extract, respectively) enzymes. F. sur extracts were tested for anticancer properties and antiviral activity towards human herpes virus type 1 (HHV-1). Stem bark infusion and methanolic extract showed antineoplastic activity against cervical adenocarcinoma and colon cancer cell lines, whereas leaf methanolic extract exerted moderate antiviral activity towards HHV-1. This investigation yielded important scientific data on F. sur which might be used to generate innovative phytopharmaceuticals. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Isolation, Structure Elucidation and Antimicrobial Evaluation of Natural Pentacyclic Triterpenoids and Phytochemical Investigation of Different Fractions of Ziziphus spina-christi (L.) Stem Bark Using LCHRMS Analysis

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Essam N. Ads

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Syed I. Hassan

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Saravanan Rajendrasozhan

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Mona H. Hetta

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Shaza H. Aly

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Mohamed A. Ali

Molecules 2022, 27(6), 1805; https://doi.org/10.3390/molecules27061805 - 10 Mar 2022

Cited by 8 | Viewed by 2120

Abstract

Ziziphus spina-christi L. (ZSC-L) is a tree with thorny branches, belongs to the family Rhamnaceae and grows in the sub-tropics. The purpose of this research is to isolate and partially purify bioactive components from the crude ethanol extract of the stem bark of [...] Read more.

Ziziphus spina-christi L. (ZSC-L) is a tree with thorny branches, belongs to the family Rhamnaceae and grows in the sub-tropics. The purpose of this research is to isolate and partially purify bioactive components from the crude ethanol extract of the stem bark of ZSC-L. Besides, bioassay-guided fractionation of ZSC-L stem bark was conducted using different solvents. The solvents were reutilized to minimize the production cost and environmental harm. In addition, the antimicrobial activities of the fractions were analyzed, followed by metabolic profiling using LC-HRMS. The n-butanol fraction showed the highest antimicrobial efficacy, so it was subjected to further purification. For the first time, two major compounds were isolated from the stem bark of ZSC-L and identified as lupane-type pentacyclic triterpenoids betulinic acid and betulin. Both compounds were used as antibacterial and anticancer agents and considered as a green product as the extraction procedure reduced the use of hazardous chemicals. Metabolic characterization of ZSC-L and its bioactive fractions were performed using LC-HR-ESI-MS and the results revealed the dereplication of 36 compounds belonging to different chemical classes. Flavonoids and triterpenes were the most prominent metabolite classes in the different fractions. The molecular docking results were obtained by studying the interaction of betulin and betulinic acid with antimicrobial receptors (4UYM, 1IYL, 1AJ2, 6J7L, 1AD4, 2VEG) to support the in vitro results. Our study highlights that Ziziphus spina-christi and its phytoconstituents, especially triterpenoids, act as a promising antimicrobial candidate in pharmaceutical and clinical applications. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Chemical Compositions and Antioxidant Activities of Essential Oils, and Their Combinations, Obtained from Flavedo By-Product of Seven Cultivars of Sicilian Citrus aurantium L.

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Mariarosaria Leporini

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Luigia Gervasi

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Rosa Tundis

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Monica Rosa Loizzo

Molecules 2022, 27(5), 1580; https://doi.org/10.3390/molecules27051580 - 27 Feb 2022

Cited by 20 | Viewed by 1945

Abstract

In this work, seven Citrus aurantium essential oils (EOs) derived from flavedo of cultivars ‘Canaliculata’, ‘Consolei’, ‘Crispifolia’, ‘Fasciata’, ‘Foetifera’, ‘Listata’, and ‘Bizzaria’ were investigated. EOs were also combined in 1:1 (v/v) ratio to identify possible synergism or antagonism of [...] Read more.

In this work, seven Citrus aurantium essential oils (EOs) derived from flavedo of cultivars ‘Canaliculata’, ‘Consolei’, ‘Crispifolia’, ‘Fasciata’, ‘Foetifera’, ‘Listata’, and ‘Bizzaria’ were investigated. EOs were also combined in 1:1 (v/v) ratio to identify possible synergism or antagonism of actions. GC-MS analysis was done to investigate Eos’ phytochemical profiles. The antioxidant activity was studied by using a multi-target approach based on FRAP, DPPH, ABTS, and β-carotene bleaching tests. A great difference was observed in EOs’ phytochemical profiles. d-limonene (33.35–89.17%) was the main monoterpene hydrocarbon, and α-Pinene, β-myrcene, and β-linalool were identified in almost all samples. Among EOs, only C3 showed high quantitative and qualitative variability in its chemical composition. The chemical diversity of EOs was also demonstrated by PCA and HCA statistical analysis. Samples C2, C4, C5, C6, and C7 were statistically similar to each other, while C1 and C3 were characterized as having a different amount of other compounds and oxygenated monoterpenes, respectively, with respect to the other EOs mentioned. The global antioxidant score (GAS) revealed that among the tested EOs, C. aurantium ‘Fasciata’ EO had the highest antioxidant potential, with a GAS value of −0.47, whereas among combinations, the EO obtained by mixing ‘Canaliculata’ + ‘Bizzaria’ was the most active. Comparison by theoretical and real data on inhibitory concentration (IC₅₀) and FRAP values did not reveal any significant effect of synergism or antagonism of actions to be valid in all biological applied tests. These findings, considered together, represent an important starting point to understand which compounds are responsible for the activities and their future possible industrial application. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Identification of α-Glucosidase Inhibitors from Scutellaria edelbergii: ESI-LC-MS and Computational Approach

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Molecules 2022, 27(4), 1322; https://doi.org/10.3390/molecules27041322 - 16 Feb 2022

Cited by 11 | Viewed by 1653

Abstract

The recent study investigated the in vitro anti-diabetic impact of the crude extract (MeOH) and subfractions ethyl acetate (EtOAc); chloroform; n-butanol; n-hexane; and aqueous fraction of S. edelbergii and processed the active EtOAc fraction for the identification of chemical constituents for the first [...] Read more.

The recent study investigated the in vitro anti-diabetic impact of the crude extract (MeOH) and subfractions ethyl acetate (EtOAc); chloroform; n-butanol; n-hexane; and aqueous fraction of S. edelbergii and processed the active EtOAc fraction for the identification of chemical constituents for the first time via ESI-LC-MS analysis through positive ionization mode (PIM) and negative ionization mode (NIM); the identified compounds were further validated through computational analysis via standard approaches. The crude extract and subfractions presented appreciable activity against the α-glucosidase inhibitory assay. However, the EtOAc fraction with IC₅₀ = 0.14 ± 0.06 µg/mL revealed the maximum potential among the fractions used, followed by the MeOH and n-hexane extract with IC₅₀ = 1.47 ± 0.14 and 2.18 ± 0.30 µg/mL, respectively. Moreover, the acarbose showed an IC₅₀ = 377.26 ± 1.20 µg/ mL whereas the least inhibition was observed for the chloroform fraction, with an IC₅₀ = 23.97 ± 0.14 µg/mL. Due to the significance of the EtOAc fraction, when profiled for its chemical constituents, it presented 16 compounds among which the flavonoid class was dominant, and offered eight compounds, of which six were identified in NIM, and two compounds in PIM. Moreover, five terpenoids were identified—three and two in NIM and PIM, respectively—as well as two alkaloids, both of which were detected in PIM. The EtOAc fraction also contained one phenol that was noticed in PIM. The detected flavonoids, terpenoids, alkaloids, and phenols are well-known for their diverse biomedical applications. The potent EtOAc fraction was submitted to computational analysis for further validation of α-glucosidase significance to profile the responsible compounds. The pharmacokinetic estimations and protein-ligand molecular docking results with the support of molecular dynamic simulation trajectories at 100 ns suggested that two bioactive compounds—dihydrocatalpol and leucosceptoside A—from the EtOAc fraction presented excellent drug-like properties and stable conformations; hence, these bioactive compounds could be potential inhibitors of alpha-glucosidase enzyme based on intermolecular interactions with significant residues, docking score, and binding free energy estimation. The stated findings reflect that S. edelbergii is a rich source of bioactive compounds offering potential cures for diabetes mellitus; in particular, dihydrocatalpol and leucosceptoside A could be excellent therapeutic options for the progress of novel drugs to overcome diabetes mellitus. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin

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André M. Marques

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Alexandre Siqueira da Rocha Queiroz

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Elsie F. Guimarães

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Ana Carolina Mafud

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Paulo de Sousa Carvalho

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Yvonne Primerano Mascarenhas

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Thais da Silva Barenco

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Pâmella Dourila N. Souza

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David William Provance

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José Hamilton M. do Nascimento

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Cristiano G. Ponte

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Maria Auxiliadora C. Kaplan

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Davyson de Lima Moreira

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Maria Raquel Figueiredo

Molecules 2022, 27(4), 1151; https://doi.org/10.3390/molecules27041151 - 09 Feb 2022

Cited by 1 | Viewed by 1240

Abstract

The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (−)-grandisin. Phytochemical analyses of extracts from its leaves, [...] Read more.

The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (−)-grandisin. Phytochemical analyses of extracts from its leaves, branches and inflorescences showed the presence of the target compound in large amounts, with leaf extracts found to contain up to 52.78% in its composition. A new HPLC-DAD-UV method was developed and validated to be selective for the identification of (−)-grandisin being sensitive, linear, precise, exact, robust and with a recovery above 90%. The absolute configuration of the molecule was determined by X-ray diffraction. Despite the identification of several enantiomers in plant extracts, the major isolated substance was characterized to be the (−)-grandisin enantiomer. In vascular reactivity tests, it was shown that the grandisin purified from botanical extracts presented an endothelium-dependent vasorelaxant effect with an IC₅₀ of 9.8 ± 1.22 μM and around 80% relaxation at 30 μM. These results suggest that P. tectoniifolium has the potential to serve as a renewable source of grandisin on a large scale and the potential to serve as template for development of new drugs for vascular diseases with emphasis on disorders related to endothelial disfunction. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Potential Anticancer Activity of the Furanocoumarin Derivative Xanthotoxin Isolated from Ammi majus L. Fruits: In Vitro and In Silico Studies

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Molecules 2022, 27(3), 943; https://doi.org/10.3390/molecules27030943 - 29 Jan 2022

Cited by 4 | Viewed by 2520

Abstract

Ammi majus L., an indigenous plant in Egypt, is widely used in traditional medicine due to its various pharmacological properties. We aimed to evaluate the anticancer properties of Ammi majus fruit methanol extract (AME) against liver cancer and to elucidate the active compound(s) [...] Read more.

Ammi majus L., an indigenous plant in Egypt, is widely used in traditional medicine due to its various pharmacological properties. We aimed to evaluate the anticancer properties of Ammi majus fruit methanol extract (AME) against liver cancer and to elucidate the active compound(s) and their mechanisms of action. Three fractions from AME (Hexane, CH₂Cl₂, and EtOAc) were tested for their anticancer activities against HepG2 cell line in vitro (cytotoxicity assay, cell cycle analysis, annexin V-FITC apoptosis assay, and autophagy efflux assay) and in silico (molecular docking). Among the AME fractions, CH₂Cl₂ fraction revealed the most potent cytotoxic activity. The structures of compounds isolated from the CH₂Cl₂ fraction were elucidated using ¹H- and ¹³C-NMR and found that Compound 1 (xanthotoxin) has the strongest cytotoxic activity against HepG2 cells (IC₅₀ 6.9 ± 1.07 µg/mL). Treating HepG2 cells with 6.9 µg/mL of xanthotoxin induced significant changes in the DNA-cell cycle (increases in apoptotic pre-G1 and G2/M phases and a decrease in the S-phase). Xanthotoxin induced significant increase in Annexin-V-positive HepG2 cells both at the early and late stages of apoptosis, as well as a significant decrease in autophagic flux in cancer compared with control cells. In silico analysis of xanthotoxin against the DNA-relaxing enzyme topoisomease II (PDB code: 3QX3) revealed strong interaction with the key amino acid Asp479 in a similar fashion to that of the co-crystallized inhibitor (etoposide), implying that xanthotoxin has a potential of a broad-spectrum anticancer activity. Our results indicate that xanthotoxin exhibits anticancer effects with good biocompatibility toward normal human cells. Further studies are needed to optimize its antitumor efficacy, toxicity, solubility, and pharmacokinetics. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Phytochemical Profiling, In Vitro Biological Activities, and In Silico Molecular Docking Studies of Dracaena reflexa

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Bilal Ahmad Ghalloo

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Kashif-ur-Rehman Khan

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Saeed Ahmad

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Hanan Y. Aati

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Jawaher H. Al-Qahtani

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Barkat Ali

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Imran Mukhtar

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Musaddique Hussain

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Muhammad Nadeem Shahzad

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Imtiaz Ahmed

Molecules 2022, 27(3), 913; https://doi.org/10.3390/molecules27030913 - 28 Jan 2022

Cited by 21 | Viewed by 2548

Abstract

Dracaena reflexa, a traditionally significant medicinal plant, has not been extensively explored before for its phytochemical and biological potential. The present study was conducted to evaluate the bioactive phytochemicals and in vitro biological activities of D. reflexa, and perform in silico [...] Read more.

Dracaena reflexa, a traditionally significant medicinal plant, has not been extensively explored before for its phytochemical and biological potential. The present study was conducted to evaluate the bioactive phytochemicals and in vitro biological activities of D. reflexa, and perform in silico molecular docking validation of D. reflexa. The bioactive phytochemicals were assessed by preliminary phytochemical testing, total bioactive contents, and GC-MS analysis. For biological evaluation, the antioxidant (DPPH, ABTS, CUPRAC, and ABTS), antibacterial, thrombolytic, and enzyme inhibition (tyrosinase and cholinesterase enzymes) potential were determined. The highest level of total phenolic contents (92.72 ± 0.79 mg GAE/g extract) was found in the n-butanol fraction while the maximum total flavonoid content (110 ± 0.83 mg QE/g extract) was observed in methanolic extract. The results showed that n-butanol fraction exhibited very significant tyrosinase inhibition activity (73.46 ± 0.80) and acetylcholinesterase inhibition activity (64.06 ± 2.65%) as compared to other fractions and comparable to the standard compounds (kojic acid and galantamine). The methanolic extract was considered to have moderate butyrylcholinesterase inhibition activity (50.97 ± 063) as compared to the standard compound galantamine (53.671 ± 0.97%). The GC-MS analysis of the n-hexane fraction resulted in the tentative identification of 120 bioactive phytochemicals. Furthermore, the major compounds as identified by GC-MS were analyzed using in silico molecular docking studies to determine the binding affinity between the ligands and the enzymes (tyrosinase, acetylcholinesterase, and butyrylcholinesterase enzymes). The results of this study suggest that Dracaena reflexa has unquestionable pharmaceutical importance and it should be further explored for the isolation of secondary metabolites that can be employed for the treatment of different diseases. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Phytochemical Screening by LC-ESI-MS/MS and Effect of the Ethyl Acetate Fraction from Leaves and Stems of Jatropha macrantha Müll Arg. on Ketamine-Induced Erectile Dysfunction in Rats

by

Johnny Aldo Tinco-Jayo

,

Enrique Javier Aguilar-Felices

,

Edwin Carlos Enciso-Roca

,

Jorge Luis Arroyo-Acevedo

and

Oscar Herrera-Calderon

Molecules 2022, 27(1), 115; https://doi.org/10.3390/molecules27010115 - 25 Dec 2021

Cited by 3 | Viewed by 2719

Abstract

Jatropha macrantha Müll Arg. L is also known as “huanarpo macho” and used in the Peruvian traditional medicine as an aphrodisiac and erectile dysfunction (ED). The aim of this study was to determine the phytochemical constituents in leaves and stems ethyl acetate fraction [...] Read more.

Jatropha macrantha Müll Arg. L is also known as “huanarpo macho” and used in the Peruvian traditional medicine as an aphrodisiac and erectile dysfunction (ED). The aim of this study was to determine the phytochemical constituents in leaves and stems ethyl acetate fraction (LEAF and SEAF) of J. macrantha and to compare the antioxidant activity and the ameliorative effect on ketamine-induced erectile dysfunction in rats. The phytochemical constituents were determined by LC-ESI-MS/MS, the total phenolic compounds and total flavonoids (TPC and TF) by Folin-Ciocalteu and aluminum chloride, respectively. The antioxidant activity was determined by DPPH, ABTS, and FRAP assays. Experimental groups were divided as follows: I: negative control; II: positive control (ketamine at 50 mg/ kg/d); III: sildenafil 5 mg/kg; IV, V, VI: LEAF at 25, 50 and 100 mg/kg, respectively, and VII, VIII, IX: SEAF at 25, 50, and 100 mg/kg, respectively. The phytochemical analysis revealed the presence mainly of coumarins, flavonoids, phenolic acids, and terpenes. TPC of LEAF and SEAF were 359 ± 5.21 mg GAE/g and 306 ± 1.93 mg GAE/g, respectively; TF in LEAF and SEAF were 23.7 ± 0.80 mg EQ/g, and 101 ± 1.42 mg EQ/g, respectively. The DPPH, ABTS, FRAP in SEAF were 647 ± 3.27; 668 ± 2.30; and 575 ± 2.86 μmol TE/g, respectively, whilst LEAF showed 796 ± 3.15; 679 ± 0.85; and 806 ± 3.42 μmol TE/g, respectively. Regarding sexual behavior, LEAF showed a better effect in mount frequency, intromission frequency, ejaculation frequency, mount latency, intromission latency, ejaculatory latency, and post ejaculatory latency than SEAF. As conclusion, LEAF of J. macrantha at 50 mg/kg showed a better effect on sexual behavior in male rats with erectile dysfunction than SEAF but not higher than sildenafil. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Open AccessArticle

Composition and Antimicrobial Activity of Ilex Leaves Water Extracts

by

Emil Paluch

,

Piotr Okińczyc

,

Anna Zwyrzykowska-Wodzińska

,

Jakub Szperlik

,

Barbara Żarowska

,

Anna Duda-Madej

,

Przemysław Bąbelewski

,

,

,

and

Molecules 2021, 26(24), 7442; https://doi.org/10.3390/molecules26247442 - 08 Dec 2021

Cited by 11 | Viewed by 2510

Abstract

Plants from the Ilex genus are known for properties such as antimicrobial and anti-inflammatory activity, can act as antiobesity agents and thus can be helpful in medicine. Some holly species, such as Ilex paraguariensis (widely known in the form of popular beverage: yerba [...] Read more.

Plants from the Ilex genus are known for properties such as antimicrobial and anti-inflammatory activity, can act as antiobesity agents and thus can be helpful in medicine. Some holly species, such as Ilex paraguariensis (widely known in the form of popular beverage: yerba mate), have been investigated, while others have been partially researched or remain unknown. Therefore, we performed qualitative and quantitative phytochemical analyses and screened antimicrobial properties of lesser-studied species (I. aquifolium L., I. aquifolium ‘Argentea Marginata’ and I. × meserveae ‘Blue Angel’). I. paraguariensis was used as a standard species for comparison purposes. Investigations were performed on water extracts due to their expected activity and composition. Antimicrobial research included evaluating minimal inhibitory, bactericidal (Staphylococcus aureus and Escherichia coli) and fungicidal concentration (Candida albicans, Alternaria alternata, Fusarium oxysporum, and Aspergillus niger) of extracts. The influence of the extracts on the production, eradication, and viability of bacterial biofilms was also analysed. It was established that Ilex paraguariensis possesses the richest profile of hydroxycinnamic acids derivatives in terms of component concentration and diversity. Ilex spp., especially I. × meserveae, contain a slightly higher amount of flavonoids and more different flavonoid derivatives than I. paraguariensis. However, the strongest antibacterial activity was shown by I. aquifolium L. and its cultivar ‘Argentea Marginata’ in terms of minimal inhibitory, bactericidal and fungicidal concentration, and biofilm assays. Extracts from both species significantly reduced the biofilm viability of S. aureus as well, which may be of use in the production of multicomponent lavaseptics, antiseptics, diuretics (supporting urinary tract infection therapy) and, due to their action on fungi, additives to growth media for specific fungi. The significant content of saponins enables Ilex extracts to be used as natural emulsifiers, for example, in cosmetics. Moreover, relatively high chlorogenic acid and rutin content may suggest use of Ilex spp. to treat obesity, digestive problems, in chemoprevention, and as preservatives in the food industry. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Review

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Open AccessReview

Arbutin: Occurrence in Plants, and Its Potential as an Anticancer Agent

by

,

,

and

Molecules 2022, 27(24), 8786; https://doi.org/10.3390/molecules27248786 - 11 Dec 2022

Cited by 3 | Viewed by 1522

Abstract

Arbutin, a hydroquinone glucoside, has been detected in ca. 50 plant families, especially in the plants of the Asteraceae, Ericaceae, Proteaceae and Rosaceae families. It is one of the most widely used natural skin-whitening agents. In addition to its skin whitening property, arbutin [...] Read more.

Arbutin, a hydroquinone glucoside, has been detected in ca. 50 plant families, especially in the plants of the Asteraceae, Ericaceae, Proteaceae and Rosaceae families. It is one of the most widely used natural skin-whitening agents. In addition to its skin whitening property, arbutin possesses other therapeutically relevant biological properties, e.g., antioxidant, antimicrobial and anti-inflammatory, as well as anticancer potential. This review presents, for the first time, a comprehensive overview of the distribution of arbutin in the plant kingdom and critically appraises its therapeutic potential as an anticancer agent based on the literature published until the end of August 2022, accessed via several databases, e.g., Web of Science, Science Direct, Dictionary of Natural Products, PubMed and Google Scholar. The keywords used in the search were arbutin, cancer, anticancer, distribution and hydroquinone. Published outputs suggest that arbutin has potential anticancer properties against bladder, bone, brain, breast, cervix, colon, liver, prostate and skin cancers and a low level of acute or chronic toxicity. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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