INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
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2020
·
IF 3.573
Haixia Xu,Xiaofeng Li,Xuan Xin,Kun Yuan,Hui Wu,Guanglei Zhao
Phenolic glycosides are the major secondary metabolites of plants, which exhibit multiple attractive biological and pharmacological activities. In this study, we developed a new and efficient method for acyl modification of phenolic glycosides by using whole-cell biocatalysts, aiming to improve their liposolubility and bioactivities. Using resveratrol, salidroside, piceid, and phlorizin as substrates, the substrate recognition characteristics of Candida parapsilosis were studied and salidroside showed the highest conversion (99.5%) but lower regioselectivity than others. Subsequently, the mechanism underlying the influences of the reaction time and organic solvents on the conversion and monoester ratio was revealed. A higher conversion of piceid was obtained in a green solvent (γ-valerolactone) than that in THF (95.8 vs 94.6%). Compared to their parent compounds, all monoester products exhibit higher liposolubility and antioxidant activity. In addition, the monoesters of salidroside and phlorizin showed significantly higher tyrosinase-inhibiting and depigmentation activities than their parents.
研究领域:
生物化学
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药理学
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植物化学
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DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2021
·
IF 5.279
Haixia Xu,Xiaofeng Li,Xuan Xin,Lan Mo,Yucong Zou,Guanglei Zhao
In this paper, an enzymatic route for synthesizing phenolic glycoside azelaic acid esters was successfully set up via lipase-catalyzed esterification and transesterification. Among the lipases tested, Candida antarctica lipase B (Novozyme 435) showed the highest activity in catalyzing esterification and Thermomyces lanuginosus (Lipozyme TLIM) gave the highest substrate conversion in catalyzing transesterification for the synthesis of ester. The addition of 4A molecular sieves into the reaction system is found to be an effective method for in situ absorption of the byproduct water and methanol, with which the substrate conversions of the enzymatic esterification and transesterification were 98.7 and 95.1%, respectively. Also, the main product ratios in transesterification were above 99.0% with lipozyme TLIM as a catalyst because the hydrolysis reaction was hindered. The results of the physical and biological properties indicate that all esters had higher Clog p values than their parent compounds. Also, the esters showed higher intracellular tyrosinase inhibitory and depigmentating activities than phenolic glycosides, azelaic acid (AA), and their physical mixtures due to their higher membrane penetration and tyrosinase inhibitory effects. In particular, piceid 6″-O-azelaic acid ester (PIA) showed the strongest inhibitory effect against melanin production. Its inhibitory rate was 77.4% at a concentration of 0.25 mM, about 4.2 times higher than that of arbutin (18.5%).
研究领域:
生物化学
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药理学
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化妆品科学
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DOI
PubMed
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
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2021
·
IF 1.571
Fang Chen,Shi-Yun Huang,Shu-Qing Xiang,Xiao-Xu Qiao,Guo-Chao Liao,Zhong-Qiu Liu,Hua Zhou,Peng Wu
Two new phenolic glycosides (1-2), along with six existing compounds (3-8), were isolated from the ethanolic extract of Ilex pubescens roots, a traditional folk medicine. These structures were determined using HR-ESI-MS, IR, UV, and NMR (including 1 D, 2 D-NMR). The anti-inflammatory activities of three phenolic glycosides (1-3) were evaluated in the human HepG2 cell lines. The results showed that compound 3 could induce P-gp and BCRP expression through the Nrf2-mediated pathway.
研究领域:
天然产物化学
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药理学
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分子生物学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2025
·
IF 8.5
Li Zhao,Shuang Luo,Zhiyun Peng,Guangcheng Wang
α-Glucosidase (α-Glu) is an enzyme that lowers postprandial blood glucose after breaking down complex carbohydrates. Kaempferide is the principal flavonoid active ingredient in plants and is widely found in fruits, vegetables, and beverages. This study found that kaempferide has the potential to inhibit α-Glu activity to treat type 2 diabetes. The results showed that kaempferide (IC 50 = 55.35 ± 0.27 μM), serving as a mixed-type inhibitor for α-Glu, exhibited sensibly superior inhibition of α-Glu than acarbose (IC 50 = 414.08 ± 10.73 μM). In addition, the outcomes from fluorescence quenching, 3D fluorescence, synchronous fluorescence, CD spectroscopy, and molecular docking analysis showed that kaempferide can not only chelate with α-Glu by hydrogen bonding and Van der Waals forces, but also affect the secondary structure and activity of the enzyme. After oral administration of sucrose in mice, kaempferide effectively reduces postprandial blood glucose (PBG) and without any other adverse symptoms. In summary, this study has the potential to contribute to the development of functional foods for the prevention and management of type 2 diabetes (T2DM).
研究领域:
生物化学
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药理学
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代谢病研究
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产品关联
DOI
PubMed
高影响因子
NATURAL PRODUCT RESEARCH
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2020
·
IF 2.158
Jin-feng Chen,Lu Tan,Feng Ju,Qi-xuan Kuang,Tian-long Yang,Fang Deng,Yu-cheng Gu,Li-shi Jiang,Yun Deng,Da-le Guo
Two new phenolic glycosides 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-(3''-α-L-arabinofuranosyl)-β-D-glucopyranoside. (1), 4-(4'-hydroxyphenyl)-2-butanone-4''-O-(6-β-D-xylosyl)-β-D-glucopyranoside (2), along with two known related analogues 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-β-D-glucopyranoside (3), 4-(4'-hydroxyphenyl)-2-butanone-4'-O-β-D-glucopyranoside (4) were obtained from the roots of Sanguisorba officinalis. Combined with acid hydrolysis derivatization, the absolute configurations of these new compounds were elucidated by comprehensive analyses of spectroscopic data including nuclear magnetic resonance (NMR), electrospray ionization high resolution mass (HRESIMS) as well as circular dichroism (CD). Compounds 1-4 exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6).
研究领域:
药理学
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化学
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植物科学
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产品关联
DOI
PubMed
高影响因子
Journal of Functional Foods
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2015
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IF 3.574
Jianmin He,Tianpeng Yin,Yang Chen,Le Cai,Zhigang Tai,Zhenjie Li,Chuanshui Liu,Yarong Wang,Zhongtao Ding
Pyrus pashia flowers are used as edible and medicinal materials in Yunnan Province, China. The antioxidant activities of 85% ethanolic extract of P. pashia flowers and derived soluble fractions were evaluated for the first time using four different test systems. The total phenolic and total flavonoid contents of each fraction were also determined. It was found that the ethyl acetate fraction exhibited the strongest antioxidant effect. An investigation of this flower's chemical constituents was carried out and led to the isolation of a new phenolic glycoside, 4- O - Z -coumaroylarbutin ( 1 ), along with twenty-seven other phenolic compounds ( 2 – 28 ). Hydroquinone ( 13 ) showed the highest content and powerful activity, which implied that the compound plays an important role in the antioxidant activity of this flower. Thus, P. pashia flowers could serve as a valuable natural antioxidant source for potential application in functional foods.
研究领域:
植物学
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食品科学
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药理学
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产品关联
DOI
高影响因子
AAPS PHARMSCITECH
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2024
·Vol. 25
·期 7
·1-15
·
IF 3.4
Shi Feng,Gong Mingjie,Adu-Frimpong Michael,Jiang Xia,Wang Xiaowen,Hua Qinyang,Li Tingyuan,Li Jiaying,Yu Jiangnan,Toreniyazov Elmurat,Cao Xia,Wang Qilong,Xu Ximing
In this study, N, N '-bis {4- [(α-L- rhamnosyloxy) benzyl]} thiourea (PG-1), a phenolic glycoside compound was purified from Moringa seed. The PG-1 has attracted extensive attention due to its anti-cancer, antioxidant, anti-inflammatory and hypoglycemic properties. However, some of its physicochemical properties such as oral bioavailability has not been studied. Herein, a highly purified PG-1 was extracted and incorporated in multiple layered liposomes (PG-1-L) to avoid its burst release and enhance oral bioavailability. After appropriate characterization, it was discovered that the obtained PG-1-L was stable, homogeneous and well dispersed with the average particle size being 89.26 ± 0.23 nm. Importantly, the in vitro release and in vivo oral bioavailability of PG-1-L were significantly improved compared with PG-1. In addition, MTT results showed that compared with the free PG-1, PG-1-L displayed obvious inhibitory effect on the HepG2 cells, while the inhibitory effect on healthy non-malignant 3T6 and LO-2 cells was not significant, indicating that PG-1-L had high safety. In conclusion, PG-1-L can be used as a promising delivery system and an ideal novel approach to improve the oral bioavailability and anticancer activity of PG-1. Graphical Abstract
研究领域:
药理学
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纳米技术
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药剂学
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药物化学
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DOI
高影响因子
JOURNAL OF ETHNOPHARMACOLOGY
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2017
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IF 2.981
Zhongcheng Ke,Gang Wang,Lei Yang,Huihui Qiu,Hao Wu,Mei Du,Juan Chen,Jie Song,Xiaobin Jia,Liang Feng
Ethnopharmacological relevance Radix paeoniae rubra , also known as chishao (CS), is a frequently used traditional Chinese medicine that can promote blood circulation to remove blood stasis . It has been widely used for the prevention and treatment of cardiovascular diseases in China. Although terpene glycoside (TG), the major component in CS, has been shown to possess cardioprotective properties, the mechanism underlying CS-TG's preventive effect against myocardial ischemia injury is unknown. This study was conducted to explore the protective and curative effects of CS-TG against isoproterenol (ISO)-induced myocardial ischemic injury in rats and investigate the underlying myocardial protective mechanisms. Materials and methods A rat model of ISO-induced myocardial ischemia was established to evaluate the protective effect of CS-TG in ameliorating heart injury. Myocardial ischemia was induced by administering ISO (40 mg/kg/d) subcutaneously for 2 days. Serum was collected and analyzed for the levels of different cardiac biomarkers, and heart tissues were isolated and prepared for ATP analysis, glycogen content determination, histopathology assay, and ultrastructure observation. The regulatory effects of CS-TG on myocardial apoptosis in rats were studied by terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) staining, and the levels of cleaved caspase-3, Bax, and Bcl-2 were detected by western blotting . Furthermore, in vitro experiments were conducted to examine whether the CS-TG's cardioprotective effects were linked to the inhibition of apoptosis via activation of the phosphoinositide-3-kinase/serine-threonine kinase AKT/mammalian target of rapamycin (PI3K/AKT/mTOR) pathway. Results CS-TG (300 mg/kg/d) significantly decreased serum levels of creatine kinase and lactate dehydrogenase in ISO-induced myocardial ischemic rats. Analysis of ATP and glycogen contents, myocardial ultrastructure, and pathological examination showed that CS-TG (300 mg/kg/d) significantly improved energy metabolism and alleviated myocardial injury in vivo. In addition, the expression of p-AKT and p-mTOR in rats subjected to CS-TG significantly elevated, while the levels of caspase-3 and Bax/Bcl-2 dramatically reduced. Moreover, treatment with LY294002 , a PI3K inhibitor, abrogated CS-TG (200 μg/mL) induced down-regulation of cleaved caspase-3, Bax/Bcl-2 in the serum. Conclusions CS-TG protects the heart from ISO-induced myocardial ischemia, potentially by improving cardiac energy metabolism and inhibiting cardiomyocyte apoptosis via activation of the PI3K/AKT/mTOR signaling pathway. Thus, CS -TG might be a potential therapeutic candidate for the prevention and treatment of myocardial ischemia.
研究领域:
药理学
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心脏病学
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中医
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分子生物学
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产品关联
DOI
PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2024
·
IF 7
Chang Zhou,Yi-fan Hu,Yan Zhang,Cheng-hao Wang,Xue-jing Liao,Fa-feng Cheng,Yan-yan Jiang
Prunella vulgaris L. (P. vulgaris) has great application value and development prospects in improving sleep. In this study, we continued to evaluate the sleep-improvement function and mechanism of P. vulgaris from both chemical characterization and function based on sleep-improvement functional ingredients, rosmarinic acid and salviaflaside, screened out in the previous stage as the index components. The chemical constituents of P. vulgaris and its phenolic acid fraction were characterized by the UPLC-MS n technology. The quality of the sleep-improvement phenolic acid fraction of P. vulgaris was scientifically evaluated by fingerprints combined with quantitative analysis of rosmarinic acid and salviaflaside. The function of phenolic acid parts of P. vulgaris in improving sleep was verified by different insomnia models including the PCPA-induced insomnia model and surface platform sleep deprivation model. HE staining was used to observe the effect of P. vulgaris on the morphology of nerve cells in different brain regions. In vivo experiments and molecular docking explored the sedative-hypnotic effects of functional ingredients of P. vulgaris . All these results investigated the material basis and mechanism of P. vulgaris to improve sleep from multiple perspectives, which contribute to providing a basis for the development of functional food to improve sleep.
研究领域:
药理学
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化学
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神经科学
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产品关联
DOI
PubMed
高影响因子
GREEN CHEMISTRY
·
2020
·Vol. 23
·期 2
·838-847
·
IF 9.48
Mingtao Zhao,Xulin Hong,Abdullah,Ruilian Yao,Yi Xiao
Biomass-derived hydroxycinnamates (mainly including p-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) from p-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
研究领域:
生物化学
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生物技术
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药学
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产品关联
DOI
高影响因子
NATURAL PRODUCT RESEARCH
·
2022
·
IF 2.488
Jun-Ran Shao,Sen-Ju Ma,Ting Li,Xiao-Qing He,Zhen-Zhong Wang,Wei Xiao,Xin-Sheng Yao,Hai-Bo Li,Yang Yu
One new phenolic glycoside (1) and one new benzofuran derivative (2) were isolated from the leaves of Illicium dunnianum. The structures of these compounds were established by using comprehensive spectroscopic data analysis, including the 1D and 2D NMR, IR, HR-ESI-MS, electronic circular dichroism and comparison with literature data. All isolates were evaluated for the inhibition against the production of NO by LPS-stimulated RAW 264.7 macrophages.
研究领域:
药用植物学
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药物化学
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免疫学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2022
·
IF 5.895
Yi-Kao Hu,Xiao-Lin Bai,Hao Yuan,Yi Zhang,Emmanuel Ayodeji Ayeni,Xun Liao
The fruits ofLycium ruthenicum Murr have long been consumed as health food and used in folk medicine in China. Apart from the well-known polysaccharides, the active small molecular constituents in this fruit have not been fully studied. In this work, a systematic phytochemical study was carried out to investigate the small molecules and their potential health benefits. Nine new polyphenolic glycosides, lyciumserin A–I (1–9), together with 16 known compounds (10–25), were isolated and elucidated by high-resolution electrospray ionization mass spectrometry and comprehensive NMR analyses in combination with chemical hydrolysis. Compounds 1, 2, and 16 exhibited moderate inhibitory activity of monoamine oxidase B (MAO-B), while compounds 1 (50 μM) and 2 (100 μM) displayed significant neuroprotective effects (69.22 and 72.38% of cell viability, respectively) in the 6-hydroxydopamine-induced injury of the PC12 cell model (54.41%), comparable to the positive drug rasagiline (70.45%). The neuroprotective effect of 1 and 2 was further evidenced by the observation of the morphological change and fluorescein diacetate/propidium iodide staining. In addition, the levels of the major active compounds (1, 3, 5/6, and 16–18) vary from 21.5 to 892.3 μg/g. This is the first report on phenolic glycosides from the fruits ofL. ruthenicum Murr that possess both significant MAO-B inhibitory and neuroprotective effects, indicating the promising potential of the fruits for the development of health care products and even therapeutic agents for the treatment of Parkinson’s disease and other neurodegenerative diseases.
研究领域:
药理学
·
神经科学
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植物化学
·
天然产物
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）