Flavone Glycosides Research Articles

Integrated multi-omic analysis reveals the cytokinin and sucrose metabolism-mediated regulation of flavone glycoside biosynthesis by MeJA exposure in Ficus pandurata Hance

Ficus pandurata Hance (FPH) holds a rich history as a traditional Chinese botanical remedy, utilized both as a culinary condiment and a medicinal intervention for diverse ailments. This study focuses on enhancing FPH's therapeutic potential by subjecting it to exogenous methyl jasmonate (MeJA) treatment, a strategy aimed at elevating the levels of active constituents to align with clinical and commercial requirements. Employing metabolomics, the impact of MeJA treatment on the lipid and flavonoid profiles of FPH leaves was investigated, revealing a marked increase in flavone glycosides, a subset of flavonoids. Investigation into the regulatory mechanism governing flavone glycoside biosynthesis uncovered elevated expression of structural genes associated with flavonoid production in response to MeJA exposure. Global endogenous hormone analysis pinpointed the selective activation of JA and cytokinin biosynthesis following MeJA treatment. Through a comprehensive integration of transcriptomic and metabolomic data, the cooperative stimulation of glucosyltransferase activity, alongside the JA and cytokinin signaling pathways, orchestrated by MeJA were explored. Furthermore, genes linked to sucrose metabolism exhibited heightened expression, concomitant with a noteworthy surge in antioxidant activity subsequent to MeJA treatment. These findings validate the augmentation of FPH leaf antioxidant capacity through MeJA intervention, while also offering profound insights into the regulatory role of MeJA in flavone glycoside biosynthesis, mediated by the interplay between cytokinin and sucrose metabolism pathways.

Hesperidin ameliorates Amyloid-β toxicity and enhances oxidative stress resistance and lifespan of Caenorhabditis elegans through acr-16 mediated activation of the autophagy pathway

Alzheimer's disease (AD) is the most prevalent neurodegenerative disease in aged populations. Aberrant amyloid-beta accumulation is a common pathological feature in AD patients. Dysfunction of autophagy and impairment of α7nAChR functioning are associated with enhanced amyloid-beta (Aβ) accumulation in AD patients. Hesperidin, a flavone glycoside found primarily in citrus species, is known to have anti-inflammatory, antioxidant, and neuroprotective effects. However, the underlying molecular mechanisms of hesperidin as an antiaging and anti-Aβ phytochemical were unclear. In this study, we found that hesperidin upregulates the acr-16 expression level in C. elegans as evidenced by increased GFP-tagged ACR-16 and GFP-tagged pmyo-3:ACR-16 expression in muscle and ventral nerve cord. Further, hesperidin upregulates the autophagy genes in wild-type N2, evident by increased GFP-tagged LGG-1 foci. However, hesperidin failed to upregulate the autophagy genes level in acr-16 mutant worms that suggests autophagy activation is mediated through acr-16. In addition, hesperidin showed antiaging and anti-oxidative effects, as evidenced by positive changes in different markers necessary for health span and lifespan. Additionally, hesperidin could upregulate acr-16 and autophagy genes (lgg-1 & bec-1) and ameliorates Aβ-induced toxicity as observed with reduce ROS accumulation, paralysis rate, and enhanced lifespan even in worms AD model CL4176 and CL2006 strain. Our finding suggests that hesperidin significantly enhances oxidative stress resistance, prolongs the lifespan, and protects against Aβ-induced toxicity in C. elegans. Thus, acr-16 mediated autophagy and antioxidation is associated with anti-aging and anti-Aβ effect of hesperidin.

Comparative analysis of composition and content of flavonoid metabolites in different tissues of Chinese jujube and sour jujube based on UPLC-ESI MS/MS metabolomics

ABSTRACT There is much variation in the distributions of secondary metabolites, such as flavonoids, among plant tissues. The flavonoids in Chinese jujube (Ziziphus jujuba Mill.) and sour jujube (Ziziphus spinosa Hu.) provide various health benefits. Variation in the distributions of flavonoids among the tissues of jujube and sour jujube has not yet been characterized. A total of 101 flavonoid metabolites, including 30 flavones, 21 flavonols, 11 flavanones, 11 isoflavanones, 8 flavanonols, 7 chalcones, 4 flavanols, 3 flavone glycosides, 2 phenolic acids, 2 ×anthones and 2 unclassified flavonoids, were identified in the fruits, leaves, flowers and seeds of Z. jujuba cv. Dongzao (DZ) and Z. spinosa cv. Liyuanzhenzhu8 (LYZZ8) using UPLC-ESI MS/MS. Principal component analysis and hierarchical cluster analysis revealed that flavonoids from the same tissues of DZ and LYZZ8 were clustered, with the exception of those from the leaves. Tissue-specific flavonoid metabolites in different tissues of DZ and LYZZ8 were identified. The main flavonoids varied among tissues, the total flavonoid content and the content of most individual flavonoids in all tissues of DZ and LYZZ8 varied (p < .05). Furthermore, 40, 50, 49 and 47 differential flavonoid metabolites were detected in the fruits, leaves, flowers and seeds of DZ and LYZZ8, respectively. Potential chemical markers for differentiating among tissues in DZ and LYZZ8 as well as among the same tissues of DZ and LYZZ8 were identified. Overall, our findings provided new insights into the flavonoid of jujube and will aid the utilization of jujube and sour jujube.

Widely targeted metabolomics and HPLC analysis elaborated the quality formation of Yunnan pickled tea during the whole process at an industrial scale.

Yunnan pickled tea is produced from fresh tea-leaves through fixation, rolling, anaerobic fermentation and sun-drying. In this study, widely targeted metabolomics using UHPLC-QQQ-MS/MS and HPLC analysis were carried out to elaborate its quality formation during the whole process. Results confirmed the contribution of preliminary treatments and anaerobic fermentation to the quality formation. A total of 568 differential metabolites (VIP>1.0, P<0.05, FC>1.50 or<0.67) were screened through OPLS-DA. (-)-Epigallocatechin and (-)-epicatechin significantly (P<0.05) increased from the hydrolyzation of ester catechins, such as (-)-epigallocatechin gallate and (-)-epicatechin gallate in anaerobic fermentation. Additionally, the anaerobic fermentation promoted vast accumulations of seven essential amino acids, four phenolic acids, three flavones and flavone glycosides, pelargonidin and pelargonidin glycosides, flavonoids and flavonoid glycosides (i.e. kaempferol, quercetin, taxifolin, apigenin, myricetin, luteolin and their glycosides) through relevant N-methylation, O-methylation, hydrolyzation, glycosylation and oxidation.

ANTIBACTERIAL COMPOUND ISOLATION AND CHARACTERIZATION FROM THE PLANT CYNOTIS AXILLARIS SCHULT.

A novel flavone glycoside was isolated from the methanolic extract of Cynotis axillaris Schult. Various analysis and characterization techniques were used to determine its structure and properties. The compound exhibited a melting point range of 231-2320C and had a molecular formula of C27H30O14. Several spectral characterization techniques were employed to establish the isolated compound's structure. These included UV-visible spectroscopy, FT-IR, LC-ESI-MS, and NMR spectroscopy. Based on these analyses, the structure of the isolated compound was determined to be 5,7,4'-trihydroxyflavone-8-α-L-rhamnopyranoside-4'-O-β-D-galactopyranosyl. This structure indicates that it is a flavone glycoside consisting of a flavone (5,7,4'-trihydroxyflavone) moiety attached to a sugar molecule (galactopyranosyl) at position 4', which further bears a rhamnose group at position 8 of the flavone. In addition, to the structural characterization, the compound also demonstrated significant antibacterial efficacy against various bacterial pathogens, including gram-positive bacteria such as Bacillus subtilis MTCC441 and gram-negative bacteria such as Escherichia coli MTCC1098, Proteus vulgarize MTCC426, and SalmonellaTyphimurium MTCC3224. The antimicrobial activity was evaluated by measuring the zone of inhibition in millimeters, which provides an indication of the compound's ability to inhibit bacterial growth. The study successfully identified and characterized a novel flavone glycoside from Cynotis axillaris Schult. and its antimicrobial activity.

Unusual acetylated flavonol glucuronides, oxyphyllvonides A−H with renoprotective activities from the fruits of Alpinae oxyphylla

As a widely consumed spice and Traditional Chinese Medicine, Alpinae oxyphylla has been used to treat conditions such as diarrhea, ulcers, dementia, and enuresis. Fruits of A. oxyphylla were phytochemically studied and the bioactive constituents against renal fibrosis were identified. Eight previously undescribed acetylated flavonol glucuronides named oxyphyllvonides A−H (1−7 and 10), two known acetylated flavonol glucuronides (8 and 9), together with seven known flavone glycosides (11−17) were isolated from the fruits of A. oxyphylla. Among them, flavonol glucuronides were discovered in Zingiberaceae for the first time. The planar structures of 1−7 and 10 were determined using HRESIMS and extensive spectroscopic techniques (UV, IR, 1D-NMR, and 2D-NMR). The absolute configurations of the sugar moiety in these compounds were determined by using LC-MS analysis of acid-hydrolyzed derivatized monosaccharides. Biological evaluation showed that 7–10, 13, 14, 16 and 17 inhibit renal fibrosis in TGF-β1-induced kidney proximal tubular cells. In addition, 7, 8 and 14 were superior to nootkatone in inhibiting Fibronectin expression. The finding has significant relevance to our ongoing research on the anti-renal fibrosis activity of A. oxyphylla.

Effect of some local plant extracts on fatty acid composition of fish (Alestes baremoze) during smoking and sun drying in the Far-North region of Cameroon.

The objective of this study was to assess the antioxidant activities of three plant extracts (Moringa oleifera leaves, Xylopia aethiopica fruits, and Allium cepa leaves) and to evaluate their effects on the preservation of fish polyunsaturated fatty acids (PUFAs) during smoking and sun-drying processes. PUFAs are highly prone to oxidation during fish processing. The plant extracts were analyzed for their polyphenol contents and were evaluated for their total antiradical capacity. The polyphenol components of each plant were characterized. The hydroethanolic and aqueous extracts were added to the fish at concentrations of 3, 6, 9, and 12 g/L and 10, 20, 30, and 40 g/L, respectively. Butylated hydroxytoluene (BHT) was used as a positive control at a concentration of 2 g/L to compare the antioxidant effects of the plant extracts. The treated fish was subjected to smoking or sun drying and the fatty acid composition of the fish lipid extract was assessed. The results showed that the total polyphenolic, flavonoid, and tannin contents varied significantly from one plant extract to the other (p < .05). The radical scavenging and FRAP increased significantly with the concentration of the plant extracts (p < .05). An HPLC analysis of the extracts led to the preliminary identification of four hydroxycinnamic acids in M. oleifera and X. aethiopica, one anthocyanin and one flavone glycoside in M. oleifera, and four flavan-3-ols in X. aethiopica. Moreover, eight flavonols were preliminarily identified in the three plants. Compared to the control product, these plant extracts significantly protected fish PUFAs from oxidation (p < .05). The aqueous extract of A. cepa at 40 g/L better preserved omega-3 in fish during smoking and sun drying than the control product. Incorporating the three plant extracts during smoking and sun-drying processes can effectively preserve the PUFAs in fish. Therefore, these plants are viable sources of natural antioxidants in the preservation of fish products.

LC-MS/MS-based metabolomics approach identified novel antioxidant flavonoids associated with drought tolerance in citrus species.

Citrus fruits are cultivated around the world, and they face drought stress frequently during their growth and development. Previous studies showed that citrus plants biosynthesized flavonoid compounds in response to abiotic stress. In this study, we have quantified 37 flavonoid compounds from the leaves of three distinct citrus species including sour orange (drought-tolerant), pummelo 'Majia you pummelo' (drought-sensitive), and lemon (drought-sensitive). The 37 flavonoids consisted of 12 flavones, 10 flavonols, 6 flavanones, 5 isoflavanones, and 1 each for chalcone, flavanol, flavanonol, and flavone glycoside. Drought stress differentially altered the flavonoid metabolism in drought-tolerant and drought-sensitive citrus species. The kaempferol 3-neohesperidoside was 17-fold higher in sour orange (124.41 nmol/L) after 18 days of drought stress than lemon (7.33 nmol/L). In sour orange, neohesperidin (69.49 nmol/L) was 1,407- and 37-fold higher than pummelo and lemon, respectively. In sour orange, some flavonoids were significantly increased, such as vitexin, neohesperidin, cynaroside, hyperoside, genistin, kaempferol 3-neohesperidoside, eriocitrin, and luteolin, in response to drought stress, whereas in lemon, these flavonoids were significantly decreased or not altered significantly in response to drought stress. Moreover, the total contents of flavonoids and antioxidant activity were increased in sour orange as compared with pummelo and lemon. The genes associated with flavonoid biosynthesis (PAL, CHI, FLS, GT1, F3H, F3'M, C4H, 4CL, FLS, FG2, FG3, and CYP81E1) were more highly expressed in sour orange leaves than in pummelo and lemon after drought stress. These outcomes showed that pummelo and lemon failed to biosynthesize antioxidant flavonoids to cope with the prolonged drought stress, whereas the sour orange biosynthesized fortified flavonoid compounds with increased antioxidant activity to detoxify the harmful effects of reactive oxygen species produced during drought stress.

Three Minor Flavone Glycosides from Aeschynanthus Species and Cultivars (Gesneriaceae)

Three minor flavonoids were isolated from the corollas and leaves of Aeschynanthus species and cultivars using MeOH, and identified as scutellarein 7- O-(6″-methylglucuronopyranoside) (1), 6-hydroxyluteolin 7- O-(6″-methylglucuronopyranoside) (2) and nepetin 4′- O-glucuronopyranoside (3) by UV and 1H NMR spectroscopy, LC–MS, and acid hydrolysis. These flavone glycosides are reported in nature for the first time.

Phytochemical Properties, Extraction, and Pharmacological Benefits of Naringin: A Review.

This review describes the various innovative approaches implemented for naringin extraction as well as the recent developments in the field. Naringin was assessed in terms of its structure, chemical composition, and potential food sources. How naringin works pharmacologically was discussed, including its potential as an anti-diabetic, anti-inflammatory, and hepatoprotective substance. Citrus flavonoids are crucial herbal additives that have a huge spectrum of organic activities. Naringin is a nutritional flavanone glycoside that has been shown to be effective in the treatment of a few chronic disorders associated with ageing. Citrus fruits contain a common flavone glycoside that has specific pharmacological and biological properties. Naringin, a flavone glycoside with a range of intriguing characteristics, is abundant in citrus fruits. Naringin has been shown to have a variety of biological, medicinal, and pharmacological effects. Naringin is hydrolyzed into rhamnose and prunin by the naringinase, which also possesses l-rhamnosidase activity. D-glucosidase subsequently catalyzes the hydrolysis of prunin into glucose and naringenin. Naringin is known for having anti-inflammatory, antioxidant, and tumor-fighting effects. Numerous test animals and cell lines have been used to correlate naringin exposure to asthma, hyperlipidemia, diabetes, cancer, hyperthyroidism, and osteoporosis. This study focused on the many documented actions of naringin in in-vitro and in-vivo experimental and preclinical investigations, as well as its prospective therapeutic advantages, utilizing the information that is presently accessible in the literature. In addition to its pharmacokinetic characteristics, naringin's structure, distribution, different extraction methods, and potential use in the cosmetic, food, pharmaceutical, and animal feed sectors were discussed.

Critical analysis of ginkgo preparations: comparison of approved drugs and dietary supplements marketed in Germany

Demographic change is taking place in the population of western industrialized countries, and the population is aging constantly. As a result, the mortality rate of patients due to dementia is rising steadily. To counteract this, the relevance of neuroprotective agents is increasing. Preparations from the medicinal tree species Ginkgo biloba (“gingko”) are becoming increasingly popular. In this study, 63 ginkgo preparations marketed in Germany were analyzed. The following data were collected from the package inserts of the preparations: Country of manufacture, approval as a drug, compliance to target values of flavone glycosides, compliance to target values of terpene lactones, compliance to target values of ginkgolic acids, dosage per unit in milligrams (mg), duration of use, interactions with other drugs, contraindications, adverse effects and daily defined dose costs. In the next step, these data were compared in the following form: Total preparations versus preparations with drug approval versus dietary supplements. Almost without exception, the results indicate a pharmaceutical reliability of the preparations with drug approval and a dubious reliability of the preparations marketed as dietary supplements. Thus, ginkgo preparations marketed as dietary supplements appear to have an economic rather than a medical focus. We discuss the evidence of efficacy, and other criteria mentioned above, to evaluate the adequacy of the costs for the statutory health insurance that pay for preparations with drug approval in Germany. From the analysis of our results it is very doubtful that ginkgo biloba extract preparations of the food industry have any health benefit. It must be evaluated whether prohibition of selling ginkgo biloba extract as a dietary supplement is an option.

The apiosyltransferase celery UGT94AX1 catalyzes the biosynthesis of the flavone glycoside apiin.

Apiose is a unique branched-chain pentose found in plant glycosides and a key component of the cell wall polysaccharide pectin and other specialized metabolites. More than 1,200 plant-specialized metabolites contain apiose residues, represented by apiin, a distinctive flavone glycoside found in celery (Apium graveolens) and parsley (Petroselinum crispum) in the family Apiaceae. The physiological functions of apiin remain obscure, partly due to our lack of knowledge on apiosyltransferase during apiin biosynthesis. Here, we identified UGT94AX1 as an A. graveolens apiosyltransferase (AgApiT) responsible for catalyzing the last sugar modification step in apiin biosynthesis. AgApiT showed strict substrate specificity for the sugar donor, UDP-apiose, and moderate specificity for acceptor substrates, thereby producing various apiose-containing flavone glycosides in celery. Homology modeling of AgApiT with UDP-apiose, followed by site-directed mutagenesis experiments, identified unique Ile139, Phe140, and Leu356 residues in AgApiT, which are seemingly crucial for the recognition of UDP-apiose in the sugar donor pocket. Sequence comparison and molecular phylogenetic analysis of celery glycosyltransferases suggested that AgApiT is the sole apiosyltransferase-encoding gene in the celery genome. Identification of this plant apiosyltransferase gene will enhance our understanding of the physioecological functions of apiose and apiose-containing compounds.

Metabolomics Reveals Distinctive Metabolic Profiles and Marker Compounds of Camellia (Camellia sinensis L.) Bee Pollen.

Camellia bee pollen (CBP) is a major kind of bee product which is collected by honeybees from tea tree (Camellia sinensis L.) flowers and agglutinated into pellets via oral secretion. Due to its special healthcare value, the authenticity of its botanical origin is of great interest. This study aimed at distinguishing CBP from other bee pollen, including rose, apricot, lotus, rape, and wuweizi bee pollen, based on a non-targeted metabolomics approach using ultra-high performance liquid chromatography-mass spectrometry. Among the bee pollen groups, 54 differential compounds were identified, including flavonol glycosides and flavone glycosides, catechins, amino acids, and organic acids. A clear separation between CBP and all other samples was observed in the score plots of the principal component analysis, indicating distinctive metabolic profiles of CBP. Notably, L-theanine (864.83-2204.26 mg/kg) and epicatechin gallate (94.08-401.82 mg/kg) were identified exclusively in all CBP and were proposed as marker compounds of CBP. Our study unravels the distinctive metabolic profiles of CBP and provides specific and quantified metabolite indicators for the assessment of authentic CBP.

Plant Growth Regulators and Activated Charcoal Selectively Affect Phenylethanoid and Flavone Glycoside Accumulation in Sideritis scardica Griseb. Tissue Culture.

Sideritis scardica Griseb. is a Balkan endemic species traditionally used for the treatment of pulmonary emphysema and angina pectoris. Recent research has also shown its phytotherapeutic potential as an anticancer and neuroprotective agent. These findings, as well as the endangered status of the species in its wild habitats, have motivated the present research on application of plant cell tissue and organ culture for the purposes of both valuable germplasm conservation and secondary metabolites production. Shoot cultures of the plant were initiated from sterile germinated seeds and the effects of activated charcoal (AC), as well benzyl adenine and 1-naphthaleneacetic acid treatments, were experimented. The phenolic profile analysis was performed by HPLC/DAD/MSn. Comparison with samples collected from wild plants in their natural habitat was performed. It was established that in vitro multiplication induced by plant growth regulators (PGRs) was accompanied by a higher impairment of leaf morphology and trichome formation, as well as by the occurrence of plantlet hyperhydricity and callus formation, as compared with the AC treatments. Shoot culture-derived plant material was shown to produce two phenylethanoids and five flavone glycosides, not detected in the wild collected plant material. In addition, the two types of in vitro culture treatments led to the stimulation of either flavone glycosides or phenylethanoids in the in vitro cultivated plants. Thus, AC stimulated, to a higher extent, flavone glycosides' accumulation, leading to an elevated flavone/phenylethanoid ratio, as compared with PGR treatments.

Evaluation of cytotoxic and apoptotic effects of the extracts and phenolic compounds of Astragalus globosus Vahl and Astragalus breviflorus DC

Astragalus L. is a genus member of the Fabaceae family, representing about 3,000 species all over the world and 380 species in Turkey. Astragalus species have been used in traditional medicine for many years. Astragalus globosus Vahl, known as “top geven”, is a dwarf, scapose, perennial herb, Astragalus breviflorus DC., known as “yünlü geven”, is an extremely spiny dwarf shrub. These endemic species grow in the Turkish cities of Erzurum, Kars, and Van. This is the first phytochemical and cytotoxic investigation of Astragalus globosus Vahl and Astragalus breviflorus DC. The main extracts and sub-fractions from the plants were evaluated for in vitro cytotoxic and apoptotic activities. The IC50 values of dichloromethane, n-butanol, and water extracts of the aerial parts of A. globosus against the MCF-7 cell line were determined as 28.39, 868.60, and 1753.00 µg/mL. The values for the MDA-MB-231 cell line were 264.00, 620.30, and 1300.50 µg/mL, respectively. From A. globosus, the following were isolated: a flavone glycoside, diosmetin-7-O-rutinoside (1); and two flavonol glycosides, isorhamnetin-3-O-rutinoside (2) and quercetin-3-O-galactoside (3). From A. breviflorus, two phenolic acids, caffeic acid (4) and chlorogenic acid (5), and a flavan-3-ol, catechin (6), were isolated. Diosmetin-7-O-rutinoside was isolated from Astragalus species for the first time and showed the highest cytotoxic activities on the MCF-7 and MDA-MB-231 breast cancer cell lines with IC50 values of 13.65 and 12.89 μg/mL, respectively. Moreover, we observed that diosmin exerts cytotoxic effects by causing cell necrosis.

Feasibility Analysis and Break Even Point Celery Farming (Apium graveolens L.) Hydroponic Deep Flow Technique (DFT) System (Case Study on a Farmer in Kayuambon Village, Lembang District, West Bandung Regency)

Medicinal properties. The celery plant also contains many apiin glycosides (flavone glycosides, isoquercetin, and umbelliferons. It also contains, mannite, inocytes, asparagine, glutamine, choline, linamarose, pro vitamin A, vitamin C, and B. This study aims to determine the cost, R/C Ratio, break-even point (BEP) of celery hydroponic farming system with deep flow technique (DFT). The analysis method used in this study is quantitative analysis by calculating and detailing the analysis of costs, income and receipts, feasibility, and break-even points. The results showed that the cost of the hydroponic agricultural system was Rp. 2,213,720.6. The R/C Ratio is 1.01, so the agricultural system is feasible. The break-even point (BEP) for receipts amounted to Rp. 2,160,006.45 while real receipts amounted to Rp. 2,224,800. This means that this agricultural system still benefits Rp. 64. 733.55. The break-even point for production is 184.48 Kg, while the actual production is 185.4 Kg. This means that production provides a benefit of 0.92 Kg. Break-even point selling price is Rp. 11,940.24/Kg while the actual selling price is Rp. 12,000/Kg. This agricultural system provides benefits of Rp. 60/Kg.

Chemical composition of extracts from leaves, stems and roots of wasabi (Eutrema japonicum) and their anti-cancer, anti-inflammatory and anti-microbial activities

The purpose of our study was to evaluate the composition of the extracts obtained from the roots and leaves of Eutrema japonicum cultivated in Poland. For this purpose, LC-DAD-IT-MS and LC-Q-TOF-MS analyses were used. The results revealed the presence of forty-two constituents comprising glycosinolates, phenylpropanoid glycosides, flavone glycosides, hydroxycinnamic acids, and other compounds. Then, the resultant extracts were subjected to an assessment of the potential cytotoxic effect on human colon adenocarcinoma cells, the effect on the growth of probiotic and intestinal pathogenic strains, as well as their anti-inflammatory activity. It was demonstrated that 60% ethanol extract from the biennial roots (WR2) had the strongest anti-inflammatory, antibacterial, and cytotoxic activities compared to the other samples. Our results suggest that extracts from E. japonicum may be considered as a promising compound for the production of health-promoting supplements.

Amenyunnaosides A-C, Three New Neolignans Isolated from Amentotaxus yunnanensis and Their Anti-inflammatory Activities.

Phytochemical study on the leaves of Amentotaxus yunnanensis led to the isolation of seventeen phenolic compounds including sixteen neolignans and lignans, and one flavone glycoside. Three among the isolates were previously unreported neolignans and named as amenyunnaosides A-C, respectively. Their structures were elucidated by extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. The isolated neolignans potentially inhibited NO production in LPS-activated RAW264.7 cells with their IC50 values ranging from 11.05 to 44.07 μM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.93 μM. Additionally, amenyunnaoside A dose-dependently reduced production of IL-6 and COX-2 but did not effect to that of TNF-α at concentrations of 0.8, 4, and 20 μM.

Quercus coccinea Münchh leaves polyphenols: Appraisal acute lung injury induced by lipopolysaccharide in mice

Genus Quercus is a well-known source for its polyphenolic content and important biological activity. Plants belonging to the Quercus genus were traditionally used in asthma, inflammatory diseases, wound healing, acute diarrhea, and hemorrhoid. Our work intended to study the polyphenolic profile of the Q. coccinea (QC) leaves and to assess the protective activity of its 80% aqueous methanol extract (AME) against lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice. Together, the potential molecular mechanism was investigated. Nineteen polyphenolic compounds (1–18), including tannins, flavone, and flavonol glycosides. Phenolic acids and aglycones were purified and identified from the AME of QC leaves. Treatment with AME of QC showed an anti-inflammatory effect evidenced by a remarkable decline in the count of white blood cells and neutrophils which was in harmony with decreasing the levels of high mobility group box-1, nuclear factor kappa B, tumor necrosis factor-α, and interleukin 1 beta. In addition, the antioxidant activity of QC was documented through the significant reduction in malondialdehyde level and elevation of reduced glutathione level and superoxide dismutase activity. Furthermore, the mechanism involved in the pulmonary protective effect of QC involved the downregulation of the TLR4/MyD88 pathway. The AME of QC showed a protective effect against LPS-induced ALI through the powerful anti-inflammatory and antioxidant activities which are linked to its abundancy with polyphenols.

Efficiency of the Enzymatic Conversion of Flavone Glycosides Isolated from Carrot Leaves and Anti-Inflammatory Effects of Enzyme-Treated Carrot Leaves.

In traditional oriental medicine, carrots (Daucus carota L.) are considered effective medicinal herbs; however, the use of D. carota leaves (DCL) as therapeutic agents has not been explored in depth. Therefore, we aimed to demonstrate the value of DCL, generally treated as waste while developing plants for wide industrial availability. Six flavone glycosides were isolated and identified from DCL, and their constituents were identified and quantitated using an NMR and HPLC/UV method, which was optimized and validated. The structure of chrysoeriol-7-rutinoside from DCL was elucidated for the first time. The method exhibited adequate relative standard deviation (<1.89%) and recovery (94.89-105.97%). The deglycosylation of DCL flavone glycosides by Viscozyme L and Pectinex was assessed. Upon converting the reaction contents to percentages, the luteolin, apigenin, and chrysoeriol groups showed values of 85.8, 33.1, and 88.7%, respectively. The enzyme-treated DCL had a higher inhibitory effect on TNF-α and IL-2 expression than that of the carrot roots or carrot leaves without enzyme treatments. These results highlight the importance of carrot leaves and could be used as baseline standardization data for commercial development.