Research

19 pages, 8952 KiB

Open AccessArticle

Determination of Volatile Organic Compounds and Endogenous Extracts and Study of Expression Patterns of TPS and BSMT in the Flowers of Seven Lilium Cultivars

by Peng Zhang, Xiaoou Ma, Qian Zhang, Ziyu Guo, Junyi Hao, Zhixuan Zhang, Ming Sun and Yan Liu

Molecules 2023, 28(24), 7938; https://doi.org/10.3390/molecules28247938 - 05 Dec 2023

Viewed by 858

Abstract

Lily is one of the most important cut flowers in the world, with a rich floral fragrance. To further explore the fragrance emission mechanisms of lily cultivars, headspace solid-phase microextraction–gas chromatography–mass spectrometry (HS-SPME-GC-MS) and organic solvent extraction–gas chromatography–mass spectrometry (OSE-GC-MS) were used to [...] Read more.

Lily is one of the most important cut flowers in the world, with a rich floral fragrance. To further explore the fragrance emission mechanisms of lily cultivars, headspace solid-phase microextraction–gas chromatography–mass spectrometry (HS-SPME-GC-MS) and organic solvent extraction–gas chromatography–mass spectrometry (OSE-GC-MS) were used to unveil the volatile organic compounds (VOCs) and endogenous extracts of seven lily cultivars. Furthermore, real-time quantitative PCR (qRT-PCR) was used to determine the expression levels of two key genes (TPS and BSMT) related to the biosynthesis of monoterpenoids and methyl benzoate. The results show that forty-five VOCs were detected in the petals of seven lily cultivars, and the main compounds were monoterpenoids and phenylpropanoids/benzenoids. Dichloromethane was the best solvent for extracting the endogenous extracts of Lilium ‘Viviana’ petals and eighteen endogenous extracts were detected using dichloromethane to extract the petals of seven lily cultivars. Each compound’s emission ratio (natural logarithm of the ratio of VOC content to endogenous extract content) was calculated, and linear regression analyses between emission ratios and boiling points were conducted. Significant linear negative correlations existed between the emission ratios and boiling points of compounds, and the regression equations’ coefficients of determination (R²) were all greater than 0.7. TPS was expressed highly in ‘Viviana’, ‘Pink News’, and ‘Palazzo’, and BSMT was expressed highly in ‘Pink News’ and ‘Palazzo’. Correlation analyses between the gene expression levels and the monoterpenoids and methyl benzoate contents found that the TPS expression levels have strong positive correlations with monoterpenoids content, while no correlations were found between the expression levels of BSMT and the contents of methyl benzoate. This study lays the foundation for research on the release patterns of VOCs in the flowers of Lilium, and the breeding of lilies for their floral fragrance. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

18 pages, 1295 KiB

Open AccessArticle

Profiling of Taxoid Compounds in Plant Cell Cultures of Different Species of Yew (Taxus spp.)

by Dmitry V. Kochkin, Elena V. Demidova, Elena B. Globa and Alexander M. Nosov

Molecules 2023, 28(5), 2178; https://doi.org/10.3390/molecules28052178 - 26 Feb 2023

Cited by 4 | Viewed by 1545

Abstract

Plant cell cultures of various yew species are a profitable source of taxoids (taxane diterpenoids) with antitumor activity. So far, despite intensive studies, the principles of the formation of different groups of taxoids in cultured in vitro plant cells have not been fully [...] Read more.

Plant cell cultures of various yew species are a profitable source of taxoids (taxane diterpenoids) with antitumor activity. So far, despite intensive studies, the principles of the formation of different groups of taxoids in cultured in vitro plant cells have not been fully revealed. In this study, the qualitative composition of taxoids of different structural groups was assessed in callus and suspension cell cultures of three yew species (Taxus baccata, T. canadensis, and T. wallichiana) and two T. × media hybrids. For the first time, 14-hydroxylated taxoids were isolated from the biomass of the suspension culture of T. baccata cells, and their structures were identified by high-resolution mass spectrometry and NMR spectroscopy as 7β-hydroxy-taxuyunnanin C, sinenxane C, taxuyunnanine C, 2α,5α,9α,10β,14β-pentaacetoxy-4(20), 11-taxadiene, and yunnanxane. UPLC–ESI-MS screening of taxoids was performed in more than 20 callus and suspension cell lines originating from different explants and grown in over 20 formulations of nutrient media. Regardless of the species, cell line origin, and conditions, most of the investigated cell cultures retained the ability to form taxane diterpenoids. Nonpolar 14-hydroxylated taxoids (in the form of polyesters) were predominant under in vitro culture conditions in all cell lines. These results, together with the literature data, suggest that dedifferentiated cell cultures of various yew species retain the ability to synthesize taxoids, but predominantly of the 14-OH taxoid group compared to the 13-OH taxoids found in plants. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

15 pages, 10297 KiB

Open AccessArticle

Structurally Different Exogenic Brassinosteroids Protect Plants under Polymetallic Pollution via Structure-Specific Changes in Metabolism and Balance of Cell-Protective Components

by Ilya E. Zlobin, Elena D. Danilova, Ol’ga K. Murgan, Liliya V. Kolomeichuk, Raisa P. Litvinovskaya, Alina L. Sauchuk, Vladimir V. Kuznetsov and Marina V. Efimova

Molecules 2023, 28(5), 2077; https://doi.org/10.3390/molecules28052077 - 22 Feb 2023

Cited by 1 | Viewed by 1104

Abstract

Heavy metals and aluminum are among the most significant abiotic factors that reduce the productivity and quality of crops in acidic and contaminated soils. The protective effects of brassinosteroids containing lactone are relatively well-studied under heavy metal stress, but the effects of brassinosteroids [...] Read more.

Heavy metals and aluminum are among the most significant abiotic factors that reduce the productivity and quality of crops in acidic and contaminated soils. The protective effects of brassinosteroids containing lactone are relatively well-studied under heavy metal stress, but the effects of brassinosteroids containing ketone are almost unstudied. Moreover, there are almost no data in the literature on the protective role of these hormones under polymetallic stress. The aim of our study was to compare the stress-protective effects of lactone-containing (homobrassinolide) and ketone-containing (homocastasterone) brassinosteroids on the barley plant’s resistance to polymetallic stress. Barley plants were grown under hydroponic conditions; brassinosteroids, increased concentrations of heavy metals (Mn, Ni, Cu, Zn, Cd, and Pb), and Al were added to the nutrient medium. It was found that homocastasterone was more effective than homobrassinolide in mitigating the negative effects of stress on plant growth. Both brassinosteroids had no significant effect on the antioxidant system of plants. Both homobrassinolide and homocastron equally reduced the accumulation of toxic metals (except for Cd) in plant biomass. Both hormones improved Mg nutrition of plants treated with metal stress, but the positive effect on the content of photosynthetic pigments was observed only for homocastasterone and not for homobrassinolide. In conclusion, the protective effect of homocastasterone was more prominent compared to homobrassinolide, but the biological mechanisms of this difference remain to be elucidated. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

20 pages, 18466 KiB

Open AccessArticle

Comprehensive Comparisons between Grafted Kynam Agarwood and Normal Agarwood on Traits, Composition, and In Vitro Activation of AMPK

by Fengming Chen, Yu Huang, Lu Luo, Qiaochu Wang, Nanxi Huang, Zhijie Zhang and Zhen Li

Molecules 2023, 28(4), 1667; https://doi.org/10.3390/molecules28041667 - 09 Feb 2023

Viewed by 3872

Abstract

Agarwood, a highly valuable resin/wood combination with diverse pharmacological activities but scarce supply, has a long history of being used as a medicine in several medical systems. Grafted Kynam agarwood (GKA) has been cultivated successfully recently and has the qualities meeting the definition [...] Read more.

Agarwood, a highly valuable resin/wood combination with diverse pharmacological activities but scarce supply, has a long history of being used as a medicine in several medical systems. Grafted Kynam agarwood (GKA) has been cultivated successfully recently and has the qualities meeting the definition of premium Kynam agarwood. However, there are few comprehensive comparisons between GKA and normal agarwood in terms of traits, global composition, and activity, and some key issues for GKA to be adopted into the traditional Chinese medical (TCM) system have not been elaborated. The two types of agarwood samples were evaluated in terms of trait characteristics, physicochemical indicators, key component groups, and global compositional profile. Furthermore, a molecular docking was performed to investigate the active ingredients. In vitro activity assays were performed to evaluate the activation of adenosine 5’-monophosphate (AMP)-activated protein kinase (AMPK) by GKA and normal agarwood. The results revealed that, overall, the traits, microscopic characteristics, chemical composition types, and bioactivity between GKA and normal agarwood were similar. The main differences were the content of resin (ethanolic extract content), the content of key component groups, and the composition of the different parent structural groups of 2-(2-phenethyl) chromones (PECs). The contents of total PEC and ethanol extract content of GKA were significantly higher than those of normal agarwood. The MS-based high-throughput analysis revealed that GKA has higher concentrations of sesquiterpenes and flindersia-type 2-(2-phenylethyl) chromones (FTPECs) (m/z 250-312) than normal agarwood. Molecular docking revealed that parent structural groups of FTPECs activated multiple signaling pathways, including the AMPK pathway, suggesting that FTPECs are major active components in GKA. The aim of this paper is to describe the intrinsic reasons for GKA as a high-quality agarwood and a potential source for novel drug development. We combined high-throughput mass spectrometry and multivariate statistical analysis to infer the different components of the two types of agarwood. Then we combined virtual screening and in vitro activity to construct a component/pharmacodynamic relationship to explore the causes of the activity differences between agarwood with different levels of quality and to identify potentially valuable lead compounds. This strategy can also be used for the comprehensive study of other TCMs with different qualities. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

16 pages, 2835 KiB

Open AccessArticle

LC-MS/MS-Based Metabolomic Profiling of Constituents from Glochidion velutinum and Its Activity against Cancer Cell Lines

by Syed Luqman Shah, Kashif Bashir, Hafiz Majid Rasheed, Jamil Ur Rahman, Muhammad Ikram, Abdul Jabbar Shah, Kamlah Ali Majrashi, Sulaiman Mohammed Alnasser, Farid Menaa and Taous Khan

Molecules 2022, 27(24), 9012; https://doi.org/10.3390/molecules27249012 - 17 Dec 2022

Cited by 5 | Viewed by 2093

Abstract

This study aimed to establish the phytochemical profile of Glochidion velutinum and its cytotoxic activity against prostate cancer (PC-3) and breast cancer (MCF-7) cell lines. The phytochemical composition of G. velutinum leaf extract and its fractions was established with the help of total phenolic [...] Read more.

This study aimed to establish the phytochemical profile of Glochidion velutinum and its cytotoxic activity against prostate cancer (PC-3) and breast cancer (MCF-7) cell lines. The phytochemical composition of G. velutinum leaf extract and its fractions was established with the help of total phenolic and flavonoid contents and LC-MS/MS-based metabolomics analysis. The crude methanolic extract and its fractions were studied for pharmacological activity against PC-3 and MCF-7 cell lines using the MTT assay. The total phenolic content of the crude extract and its fractions ranged from 44 to 859 µg GAE/mg of sample whereas total flavonoid contents ranged from 20 to 315 µg QE/mg of sample. A total of forty-eight compounds were tentatively dereplicated in the extract and its fractions. These phytochemicals included benzoic acid derivatives, flavans, flavones, O-methylated flavonoids, flavonoid O- and C-glycosides, pyranocoumarins, hydrolysable tannins, carbohydrate conjugates, fatty acids, coumarin glycosides, monoterpenoids, diterpenoids, and terpene glycosides. The crude extract (IC₅₀ = 89 µg/mL), the chloroform fraction (IC₅₀ = 27 µg/mL), and the water fraction (IC₅₀ = 36 µg/mL) were found to be active against the PC-3 cell line. However, the crude extract (IC₅₀ = 431 µg/mL), the chloroform fraction (IC₅₀ = 222 µg/mL), and the ethyl acetate fraction (IC₅₀ = 226 µg/mL) have shown prominent activity against breast cancer cells. Moreover, G. velutinum extract and its fractions presented negligible toxicity to normal macrophages at the maximum tested dose (600 µg/mL). Among the compounds identified through LC-MS/MS-based metabolomics analysis, epigallocatechin gallate, ellagic acid, isovitexin, and rutin were reported to have anticancer activity against both prostate and breast cancer cell lines and might be responsible for the cytotoxic activities of G. velutinum extract and its bioactive fractions. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

12 pages, 1789 KiB

Open AccessArticle

Chemical Analysis and Antimicrobial Activity of Moringa oleifera Lam. Leaves and Seeds

by Attilio Anzano, Bruna de Falco, Mohammad Ammar, Annarita Ricciardelli, Laura Grauso, Mohammed Sabbah, Rosanna Capparelli and Virginia Lanzotti

Molecules 2022, 27(24), 8920; https://doi.org/10.3390/molecules27248920 - 15 Dec 2022

Cited by 6 | Viewed by 2066

Abstract

Moringa oleifera is a traditional food crop widespread in Asiatic, African, and South American continents. The plant, able to grow in harsh conditions, shows a high nutritional value and medicinal potential evidencing cardioprotective, anti-inflammatory, antioxidant, and antimicrobial properties. The purpose of this study [...] Read more.

Moringa oleifera is a traditional food crop widespread in Asiatic, African, and South American continents. The plant, able to grow in harsh conditions, shows a high nutritional value and medicinal potential evidencing cardioprotective, anti-inflammatory, antioxidant, and antimicrobial properties. The purpose of this study was the phytochemical analysis of M. oleifera and the identification of the antimicrobial compounds by combining a chemical approach with in vitro tests. The metabolite profile of M. oleifera polar and apolar extracts of leaves and seeds were investigated by using Nuclear Magnetic Resonance spectroscopy and Gas Chromatography-Mass Spectrometry. The antimicrobial activity of all of the obtained extract was evaluated against four bacterial pathogens (Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa and Salmonella enterica). The chemical analysis provided a wide set of metabolites that were identified and quantified. Moreover, apolar extracts from seeds showed a significant concentration-dependent antimicrobial activity against S. aureus and S. epidermidis, (4 mg/mL reduced the viability up to 50%) that was associated to the content of specific fatty acids. Our results remarked the advantages of an integrated approach for the identification of plant metabolites and its use in association with biological tests to recognize the compounds responsible for bioactivity without compounds purification. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

9 pages, 946 KiB

Open AccessArticle

Activation of a Sweet Taste Receptor by Oleanane-Type Glycosides from Wisteria sinensis

by Samir Hobloss, Antoine Bruguière, David Pertuit, Tomofumi Miyamoto, Chiaki Tanaka, Christine Belloir, Marie-Aleth Lacaille-Dubois, Loïc Briand and Anne-Claire Mitaine-Offer

Molecules 2022, 27(22), 7866; https://doi.org/10.3390/molecules27227866 - 15 Nov 2022

Viewed by 1411

Abstract

The phytochemical study of Wisteria sinensis (Sims) DC. (Fabaceae), commonly known as the Chinese Wisteria, led to the isolation of seven oleanane-type glycosides from an aqueous-ethanolic extract of the roots. Among the seven isolated saponins, two have never been reported before: 3-O [...] Read more.

The phytochemical study of Wisteria sinensis (Sims) DC. (Fabaceae), commonly known as the Chinese Wisteria, led to the isolation of seven oleanane-type glycosides from an aqueous-ethanolic extract of the roots. Among the seven isolated saponins, two have never been reported before: 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-acetylolean-12-ene-3β,16β,22β,30-tetrol, and 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosylwistariasapogenol A. Based on the close structures between the saponins from W. sinensis, and the glycyrrhizin from licorice, the stimulation of the sweet taste receptor TAS1R2/TAS1R3 by these glycosides was evaluated. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Graphical abstract

13 pages, 3787 KiB

Open AccessArticle

Evaluation of a Chaotrope and Kosmotrope in the Multivariate Optimization of PHW-ATPE of Solasodine from Leaves of Solanum mauritianum

by Tebogo Mphatlalala Mokgehle, Ntakadzeni Edwin Madala and Nikita Tawanda Tavengwa

Molecules 2022, 27(17), 5547; https://doi.org/10.3390/molecules27175547 - 29 Aug 2022

Cited by 1 | Viewed by 1254

Abstract

A hyphenated pressurized hot water—aqueous two-phase extraction (PHW-ATPE) method was applied to extract solasodine from Solanum mauritianum (S. mauritianum). A central composite design (CCD) was applied to determine the optimal conditions for the extraction of solasodine. The parameters evaluated included the [...] Read more.

A hyphenated pressurized hot water—aqueous two-phase extraction (PHW-ATPE) method was applied to extract solasodine from Solanum mauritianum (S. mauritianum). A central composite design (CCD) was applied to determine the optimal conditions for the extraction of solasodine. The parameters evaluated included the percentage concentration of salt (NaCl or Na₂CO₃) and temperature. The fit of the central composite design response surface model for PHW-ATPE to the data generated a model with a good quadratic fit (R² = 0.901). The statistically significant (p < 0.05) parameters, such as the linear and quadratic effects of the concentration of salt (%) powder, had a significant impact on the extraction of solasodine. The application of multiply charged salts such as Na₂CO₃ (kosmotrope) was shown to be a comparably better extractant of solasodine than NaCl (chaotrope) due to the salting-out effect. The optimized conditions for extraction of solasodine with NaCl or Na₂CO₃ were a temperature of 80 °C at a salt concentration of 20%. The maximum extraction of solasodine was 300.79 mg kg⁻¹ and 162.34 mg kg⁻¹ for Na₂CO₃ and NaCl, respectively. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Figure 1

16 pages, 5853 KiB

Open AccessArticle

Friedelin Attenuates Neuronal Dysfunction and Memory Impairment by Inhibition of the Activated JNK/NF-κB Signalling Pathway in Scopolamine-Induced Mice Model of Neurodegeneration

by Marva Sandhu, Hafiz Muhammad Irfan, Shahid Ali Shah, Madiha Ahmed, Iffat Naz, Muhammad Akram, Humaira Fatima and Ayesha Shuja Farooq

Molecules 2022, 27(14), 4513; https://doi.org/10.3390/molecules27144513 - 14 Jul 2022

Cited by 11 | Viewed by 1840

Abstract

Oxidative stress (OS) and c-Jun N-terminal kinase (JNK) are both key indicators implicated in neuro-inflammatory signalling pathways and their respective neurodegenerative diseases. Drugs targeting these factors can be considered as suitable candidates for treatment of neuronal dysfunction and memory impairment. The present study [...] Read more.

Oxidative stress (OS) and c-Jun N-terminal kinase (JNK) are both key indicators implicated in neuro-inflammatory signalling pathways and their respective neurodegenerative diseases. Drugs targeting these factors can be considered as suitable candidates for treatment of neuronal dysfunction and memory impairment. The present study encompasses beneficial effects of a naturally occurring triterpenoid, friedelin, against scopolamine-induced oxidative stress and neurodegenerative pathologies in mice models. The treated animals were subjected to behavioural tests i.e., Y-maze and Morris water maze (MWM) for memory dysfunction. The underlying mechanism was determined via western blotting, antioxidant enzymes and lipid profile analyses. Molecular docking studies were carried out to predict the binding modes of friedelin in the binding pocket of p-JNK protein. The results reveal that scopolamine caused oxidative stress by (1) inhibiting catalase (CAT), peroxidase enzyme (POD), superoxide dismutase (SOD), and reduced glutathione enzyme (GSH); (2) the up-regulation of thiobarbituric acid reactive substances (TBARS) in mice brain; and (3) affecting the neuronal synapse (both pre- and post-synapse) followed by associated memory dysfunction. In contrast, friedelin administration not only abolished scopolamine-induced oxidative stress, glial cell activation, and neuro-inflammation but also inhibited p-JNK and NF-κB and their downstream signaling molecules. Moreover, friedelin administration improved neuronal synapse and reversed scopolamine-induced memory impairment accompanied by the inhibition of β-secretase enzyme (BACE-1) to halt amyloidogenic pathways of amyloid-β production. In summary, all of the results show that friedelin is a potent naturally isolated neuro-therapeutic agent to reverse scopolamine-induced neuropathology, which is characteristic of Alzheimer’s disease. Full article

(This article belongs to the Special Issue Analysis of Phytochemical Components)

► Show Figures

Graphical abstract

Journal Menu

Journal Browser

Analysis of Phytochemical Components

Share This Special Issue

Special Issue Editors

Special Issue Information

Keywords

Published Papers (9 papers)

Research

Further Information

Guidelines

MDPI Initiatives

Follow MDPI