MOLECULES
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2022
·Vol. 27
·期 21
·7390
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IF 4.927
Shi-Hui Lu,Hao-Jiang Zuo,Jing Huang,Ran Chen,Jia-Ping Pan,Xiu-Xia Li
The phytochemical study on the leaves ofLigustrum robustum, which have been used as Ku-Ding-Cha, led to the isolation and identification of three new phenylethanoid glycosides and three new phenylmethanoid glycosides, named ligurobustosides R1(1b), R2–3(2), R4(3), S1(4b), S2(5), and S3(6), and five reported phenylethanoid glycosides (7–11). In the bioactivity test, (Z)-osmanthuside B6(11) displayed strong fatty acid synthase (FAS) inhibitory activity (IC50: 4.55 ± 0.35 μM) as the positive control orlistat (IC50: 4.46 ± 0.13 μM), while ligurobustosides R4(3) and S2(5), ligupurpuroside B (7),cis-ligupurpuroside B (8), ligurobustoside N (9), osmanthuside D (10), and (Z)-osmanthuside B6(11) showed stronger ABTS radical scavenging activity (IC50: 2.68 ± 0.05~4.86 ± 0.06 μM) than the positive control L-(+)-ascorbic acid (IC50: 10.06 ± 0.19 μM). This research provided a theoretical basis for the leaves ofL. robustumas a tea with function in treating obesity and diabetes.Keywords:Ligustrum robustum;phenylethanoid glycoside;phenylmethanoid glycosides;FAS;α-glucosidase;antioxidant;anti-obesity;hypoglycemic
研究领域:
植物化学
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药理学
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代谢生物学
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DOI
PubMed
高影响因子
Plant Communications
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2025
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IF 11.6
Ruolong Ma,Hongli Wei,Yibin Zhuang,Yanan Wu,Zhishuai Li,Yangyang Chen,Jing Huang,Xiaohui Yan,Weidong Liu,Tao Liu
Phenylethanoid glycosides (PhGs) are a group of important natural products found in a wide variety of medicinal plants, and are known to possess outstanding pharmacological properties. Uridine diphosphate (UDP) glycosyltransferase 79G15 (UGT79G15) from Rehmannia glutinosa catalyzes the conversion of osmanthuside A to osmanthuside B, a key intermediate in the PhG biosynthetic pathway, via the formation of a (1→3) glycosidic bond. In this study, we report the crystal structure of UGT79G15 in its apo form, UDP-bound form and, most importantly, its ternary complex form containing UDP and a mimic acceptor, forsythiaside A, in its active site. Structural and comparative analyses revealed that UGT79G15 has a unique ‘funnel-shaped’ acceptor-binding pocket with a small accessory cave sufficient to accommodate the 4′-hydroxycinnamoyl group of PhG, explaining the enzyme′s regiospecificity for the 3′-OH of PhG. Further structural analysis and site-directed mutagenesis explored a number of variants of the enzyme and identified key residues that recognize and stabilize UDP-rhamnose and the sugar acceptor. Meanwhile, I204W, a point variant obtained in the process, was found to possess increased catalytic efficiency for osmanthuside A conversion, up to 2.2 times the efficiency of the wild type. This study provides mechanistic insights into the donor specificity and acceptor regioselectivity of PhG 1,3-rhamnosyltransferase and enriches structural information on plant UGTs.
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2015
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IF 2.912
Yirong Jiang,Shuqin Mao,Weisu Huang,Baiyi Lu,Zengxuan Cai,Fei Zhou,Maiquan Li,Tiantian Lou,Yajing Zhao
Variations of phenylethanoid glycoside profiles and antioxidant activities in Osmanthus fragrans flowers through the digestive tract were evaluated by a simulated digestion model and UPLC/PDA/MS. Major phenylethanoid glycosides and phenolic acids, namely, salidroside, acteoside, isoacteoside, chlorogenic acid, and caffeic acid, were identified in four cultivars of O. fragrans flowers, and the concentration of acteoside was the highest, being up to 71.79 mg/g dry weight. After simulated digestion, total phenylethanoid glycoside contents and antioxidant activities were significantly decreased. Acteoside was identified as decomposing into caffeic acid, whereas salidroside was found to be stable during simulated digestion. According to Pearson’s correlation analysis, acteoside contents showed good correlations with antioxidant activities during simulated digestion (R2 = 0.994, P < 0.01). In conclusion, acteoside was the major contributor to the antioxidant activity of O. fragrans flowers, and salidroside was considered as the major antioxidant compound of O. fragrans flowers in vivo.
研究领域:
植物学
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药理学
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分析化学
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DOI
PubMed
高影响因子
Scientific Reports
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2017
·Vol. 7
·期 1
·1-10
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IF 4.259
Zhou Fei,Zhao Yajing,Li Maiquan,Xu Tao,Zhang Liuquan,Lu Baiyi,Wu Xiaodan,Ge Zhiwei
This study was aimed at investigating the chemical stability (the thermal, light and pH stability) of phenylethanoid glycosides (PhGs) in Osmanthus fragrans Lour. flowers, identifying the degradation products of acteoside and salidroside (major PhGs in O. fragrans flowers) by UPLC–QTOF–MS and studying the anti-hypoxia activity of PhGs after degradation. The degradation of PhGs followed first-order reaction kinetics, and the rate constant of acteoside (4.3 to 203.4 × 10 −3 day −1 ) was higher than that of salidroside (3.9 to 33.3 × 10 −3 day −1 ) in O. fragrans flowers. Salidroside was mainly hydrolyzed to tyrosol during storage, and the degradation products of acteoside were verbasoside, caffeic acid, isoacteoside, etc. In a model of cobalt chloride (CoCl 2 )-induced hypoxia in PC12 cells, the anti-hypoxia ability of PhGs decreased after degradation, which resulted from the reduction of PhGs contents. Particularly, caffeic acid exhibited stronger anti-hypoxia ability than acteoside and could slightly increase the anti-hypoxia ability of degraded acteoside. The results revealed that high temperature, high pH and light exposure caused PhGs degradation, and thus the anti-hypoxia ability of PhGs reduced.
研究领域:
药理学
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植物化学
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生物化学
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PubMed
高影响因子
PHYTOCHEMISTRY
·
2024
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IF 3.2
Meihong Liu,Haibo Tan,Haihui Xie
ABSTRACT Chemical investigation on the leaves of Michelia champaca L. (Magnoliaceae) led to the isolation of five previously undescribed phenylethanoid glycosides (PhGs), 4- O - β - d -glucopyranosyl-acteoside ( 1 ), 4"'- O -(6- O - E -caffeoyl)- β - d -glucopyranosyl-acteoside ( 2 ), 4"'- O -(6- O - E -caffeoyl)- β - d -glucopyranosyl-isoacteoside ( 3 ), 6""- O - E -feruloyl-echinacoside ( 4 ), and 6""- O - p - E -coumaroyl-echinacoside ( 5 ), together with eighteen known PhGs. Their structures were determined by spectroscopic and chemical methods. All the known PhGs except acteoside ( 8 ) were not previously reported in the genus. Twenty-one PhGs exhibited more potent DPPH radical scavenging activity and FRAP than l -ascorbic acid ( l -AA), and twenty-two PhGs showed better ABTS radical cation scavenging activity than l -AA. In addition, twelve PhGs displayed more potent cellular reactive oxygen species (ROS) scavenging activity than curcumin. The results revealed that the leaves of M. champaca are a rich source of phenylethanoid glycosides and antioxidants.
研究领域:
药用植物学
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天然产物化学
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植物化学
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DOI
PubMed
高影响因子
JOURNAL OF ETHNOPHARMACOLOGY
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2020
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IF 3.69
Ying-Qi Li,Yi Chen,Jia-Yi Fang,Si-Qi Jiang,Ping Li,Fei Li
Ethnopharmacological relevance Osteoporosis (OP) and Alzheimer's disease (AD) are common geriatric concurrent diseases, and many studies indicate the connection of their pathogenesis. Cistanche tubulosa (Schenk) Wight (CT) is a widely used traditional Chinese medicine and has been extensively applied to treat OP and AD, respectively. However, the active ingredients for both concurrent diseases simultaneously and underlying mechanisms are limited. Aim of study This work aimed at establishing an effective and reliable network screening method to find dual-effects compounds in CT that can protect AD and OP concurrently. And it will provide new perspectives of the link between OP and AD on molecular mechanisms. Material and methods The dual-effects of CT were systematically analyzed with integrating multiple databases and extensive analysis at a network pharmacology level. Classified drug-target interaction network was constructed to reveal differences in effects between different types of compounds. To prove the effectiveness of this network, some compounds were selected to verify in Pre-induced OP model and AlCl 3 -induced AD model of zebrafish according to the topological parameters. Results 22 dual-effects active ingredients in CT were initially screened out via network pharmacology with a closely connection with 81 OP and AD-related targets. Classified network analysis found the better bioactivities of phenylethanoid glycosides and flavonoids . The dual-effects of four selected compounds demonstrated that the network is reasonable and effective, suggesting the dual-effects of the remaining 18 compounds. Moreover, we identified 9 putative targets and two pathways that were significantly related to OP and AD. Conclusions We successfully identified 22 dual-effects active components in CT. This systematic screening strategy provided a new protocol to objectively discover multi-effects compounds of traditional Chinese medicine, and even a macroscopic perspective that will improve our understanding of the link between OP and AD on molecular mechanisms.
研究领域:
药理学
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老年医学
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传统中药
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分子生物学
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神经科学
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DOI
PubMed
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
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2016
·
IF 3.169
Yang Li,Ying Peng,Mengyue Wang,Guisheng Zhou,Yulong Zhang,Xiaobo Li
Cistanches Herba is a famous traditional Chinese medicine that has been in use for treating kidney deficiency, impotence, female infertility, morbid leucorrhea, profuse metrorrhagia, and senile constipation. With the exception of studies available for a few single active ingredients such as echinacoside, acteoside, and poliumoside, comprehensive and systematic studies on in vivo metabolism of Cistanches Herba are lacking despite its widespread clinical application. There is no comparative study yet on the metabolites resulting from the traditional usage of Cistanche deserticola and C. tubulosa water extract – two species that are recorded in Chinese Pharmacopoeia. This further restricts research on the therapeutic effect of Cistanches Herba to a great extent. In this study, a robust and unbiased UPLC-Q-TOF-MS combined pattern recognition analysis (orthogonal partial least squared discriminant analysis, OPLS-DA) was employed to rapidly screen prototype components and metabolites of C. deserticola and C. tubulosa water extract in rat urine, feces, and serum. A total of 71 metabolites from C. deserticola including 25 prototype components and 46 metabolites, and 45 metabolites from C. tubulosa including 18 prototype components and 27 metabolites were tentatively identified. Out of these, 10 metabolites were characterized for the first time in these two species. Results of this study indicate that phenylethanoid glycosides (PhGs) are mainly metabolized into degradation products in the gastrointestinal tract of rats. The chemical components cistanoside B, C, D, and E exist only in C. deserticola and release methylated hydroxytyrosol (HT) following metabolism. This factor contributes to the difference between metabolites of C. deserticola and C. tubulosa water extract in rats and is responsible for the differential therapeutic effect that these two species of Cistanches Herba have on the same diseases.
研究领域:
药理学
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分析化学
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中医药学
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2018
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IF 3.412
Fei Zhou,Weisu Huang,Maiquan Li,Yongheng Zhong,Mengmeng Wang,Baiyi Lu
Acteoside and salidroside are major phenylethanoid glycosides (PhGs) in Osmanthus fragrans Lour. flowers with extensive pharmacological activities and poor oral bioavailability. The absorption mechanisms of these two compounds remain unclear. This study aimed to investigate the bioaccessibility of these compounds using an in vitro gastrointestinal digestion model and to examine the absorption and transport mechanisms of PhGs using the Caco-2 cell model. The in vitro digestion model revealed that the bioaccessibility of salidroside (98.7 ± 1.35%) was higher than that of acteoside (50.1 ± 3.04%), and the superior bioaccessibility of salidroside can be attributed to its stability. The absorption percentages of total phenylethanoid glycoside, salidroside, and acteoside were 1.42–1.54%, 2.10–2.68%, and 0.461–0.698% in the Caco-2 model, respectively. Salidroside permeated Caco-2 cell monolayers through passive diffusion. At the concentration of 200 μg/mL, the apparent permeability (Papp) of salidroside in the basolateral (BL)-to-apical (AP) direction was 23.7 ± 1.33 × 10–7 cm/s, which was 1.09-fold of that in the AP-to-BL direction (21.7 ± 1.38 × 10–7 cm/s). Acteoside was poorly absorbed with low Papp (AP to BL) (4.75 ± 0.251 × 10–7 cm/s), and its permeation mechanism was passive diffusion with active efflux mediated by P-glycoprotein (P-gp). This study clarified the bioaccessibility, absorption, and transport mechanisms of PhGs. It also demonstrated that the low bioavailability of acteoside might be attributed to its poor bioaccessibility, low absorption, and P-gp efflux transporter.
研究领域:
药理学
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营养科学
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细胞生物学
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食品化学
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DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
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2019
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IF 2.813
Yang Li,Ying Peng,Ping Ma,Mengyue Wang,Chongsheng Peng,Pengfei Tu,Xiaobo Li
Cistanche tubulosa , one species of Cistanches Herba, was recently confirmed to have antidepressant efficacy in chronic unpredictable stress (CUS) rats by restoring homeostasis of intestinal microbiota . In this paper, we aim to explore the metabolic profile of C. tubulosa in normal and CUS induced depressive model rats in vitro and in vivo . Using UPLC-Q-TOF-MS, the in vitro gastrointestinal metabolism of Cistanche tubulosa extract (CTE) was evaluated in both normal and CUS rats. At the same time, in vivo metabolism of CTE in normal and depressed rats were also investigated in rat urine and feces. A total of 20 and 26 metabolites were characterized from in vitro and in vivo metabolism in normal and CUS rats, respectively. CTE was metabolized to aglycones and degradation products of phenylethanoid glycosides (PhGs) and iridoid glycosides whether by normal or depressed rat intestinal microbiota in vitro . Phase II metabolites of aglycones and degradation products of PhGs and iridoid glycosides were the main metabolites in rat urine and feces. Additionally, the metabolic capability to generate secondary glycosides and aglycones in depressive rat intestinal microbiota was much weaker than that in normal rat intestinal microbiota, which was attributed to the disordered glycoside hydrolases produced by intestinal microbiota in CUS depressed rats. The results of this study laid the foundation for understanding the metabolic process and therapeutic mechanism of CTE's antidepressant property.
研究领域:
药理学
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神经科学
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微生物学
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代谢组学
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DOI
PubMed
高影响因子
ORGANIC & BIOMOLECULAR CHEMISTRY
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2023
·Vol. 21
·期 21
·4445-4454
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IF 3.2
Yanan Wu,Yihan Yang,Liping Du,Yibin Zhuang,Tao Liu
Glycosylation reactions mediated by UDP-glycosyltransferases (UGTs) are common post-modifications involved in plant secondary metabolism and significantly improve the solubility and bioactivity of aglycones. Penstemon barbatus is rich in phenylethanoid glycosides (PhGs), such as echinacoside and verbascoside. In this study, a promiscuous glycosyltransferase UGT84A95 was identified from P. barbatus. In vitro enzyme assays showed that UGT84A95 catalyzed the glucosylation of the phenol hydroxyl group of PhGs efficiently as well as other structurally diverse phenolic glycosides, including flavonoids, terpenoids, stilbene glycosides, coumarins, and simple polyphenols. By using UGT84A95, 12 glycosylated products were prepared and structurally identified by NMR spectroscopy, among which 7 are new compounds. These findings suggest that UGT84A95 could be a potential biocatalyst to synthesize multi-glycosylated glycosides.
研究领域:
植物代谢
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酶学
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天然产物化学
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DOI
PubMed
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
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2015
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IF 2.979
Yang Li,Guisheng Zhou,Ying Peng,Pengfei Tu,Xiaobo Li
Acteoside, isoacteoside, and 2′-acetylacteoside are three representative phenylethanoid glycosides (PhGs), which are widely distributed in many plants and also known as the active components of Cistanches Herba . However, the extremely low oral bioavailability of acteoside in rats implies that these structural similar components may go through multiple sequential routes of hydrolysis in gastrointestinal tract before they are absorbed into blood. Therefore, the metabolites of these three components and other PhGs from gastrointestinal tract such as echinacoside, are supposed to be the bioactive elements. In this study, we established an approach combining ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF-MS) with MS E technology and MetaboLynx™ software for the rapid metabolic profiling of acteoside, isoacteoside, and 2′-acetylacteoside by human intestinal bacteria. As a result, 11 metabolites of acteoside, 7 metabolites of isoacteoside, and 11 metabolites of 2′-acetylacteoside were identified respectively. 8 metabolic pathways including deglycosylation, de-rhamnose, de-hydroxytyrosol, de-caffeoyl, deacetylation, reduction, acetylation, and sulfate conjugation were proposed to involve in the generation of these metabolites. Furthermore, we found that the degraded metabolites hydroxytyrosol (HT) and 3-hydroxyphenylpropionic (3-HPP) were transformed from acteoside, isoacteoside, and 2′-acetylacteoside by human intestinal bacteria and demonstrated similar bioactivities to their precursors. These findings are significant for our understanding of the metabolism of PhGs and the proposed metabolic pathways of bioactive components might be crucial for further pharmacokinetic evaluations of Cistanches Herba .
研究领域:
药理学
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微生物学
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分析化学
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DOI
PubMed
高影响因子
World Journal of Traditional Chinese Medicine
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2024
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IF 4.3
Gao Hong-Xue,Liu Zhi-Qiang,Hou Zong,Song Feng-Rui,Xing Jun-Peng,Zheng Zhong,Liu Shu
Objective: This study aimed to elucidate the active components and mechanisms of Plantago asiatica L. (PAL) in the treatment of gout. Materials and Methods: Based on its polarity, PAL was partitioned into three parts, P1, P2, and P3, through gradient elution using AB-8 macroporous resin columns. The primary constituents of these fractions include iridoids, phenylethanoid glucosides, and flavonoids. Subsequently, a comprehensive in vitro and in vivo screening and evaluation model was developed considering the fundamental pathological processes of gout, including the inhibition of uric acid (UA) production, augmentation of UA excretion, and anti-inflammatory effects. This model was used to analyze the anti-gout activity of P1, P2, P3, and the overall extracts derived from PAL. Results: All the PAL parts exhibited specific therapeutic properties as part of gout therapy. Specifically, the P2 part demonstrated the ability to diminish interleukin-1 beta levels, lower UA concentrations, suppress joint inflammation in rats, and restore abnormal parameters associated with gout, such as creatinine and urea nitrogen. These findings highlight the significant effect of P2 on gout treatment. Conclusions: Following a thorough assessment of the outcomes derived from diverse anti-gout experiments, P2 exhibited superior anti-gout properties compared to the remaining parts. P2 demonstrated a restorative effect on the aberrant parameters associated with gout, thereby comprehensively elucidating the therapeutic mechanism of P2 against gout. This study provides substantial evidence and serves as a reference for future investigations regarding the material foundation of PAL in gout treatment.
研究领域:
药理学
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药用植物研究
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生物化学
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炎症研究
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产品关联
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高影响因子
危险品化学品经营许可证（带存储）