FOOD CHEMISTRY
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2017
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IF 4.529
Hua Zhou,Hai-Mei Li,Yang-Min Du,Ri-An Yan,Shi-Yi Ou,Tian-Feng Chen,Yong Wang,Li-Xin Zhou,Liang Fu
YingDe black tea is produced from crude tea prepared from leaves of Camellia sinensis var. assamica . In this work, we isolated and identified five novel flavanones, namely, amelliaone A – E ( 1 – 5 ), along with seven known compounds 6 – 12 from the ethanol extract of YingDe black tea. The structures of these five novel phenolic compounds were determined using extensive 1D and 2D nuclear magnetic resonance spectroscopy experiments. The compounds were further evaluated for antioxidant, α -glucosidase inhibitory, and cytotoxic activities. Compound 1 exhibited higher α -glucosidase inhibitory activity with a half-maximum inhibitory concentration value (IC 50 ) of 10.2 µM compared with acarbose (18.2 µM).
研究领域:
药理学
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生物化学
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植物化学
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DOI
PubMed
高影响因子
MOLECULES
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2020
·Vol. 25
·期 14
·3298
·
IF 3.267
Na Li,Liyan Liu,Huiqing Luo,Huaqiao Wang,Depo Yang,Feng He
Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction ofo-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (φF), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.Keywords:AIEE;flavanone;mitochondria;zebrafish
研究领域:
化学
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材料科学
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生物技术
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生物学
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DOI
PubMed
高影响因子
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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2013
·Vol. 2013
·期 32
·7411-7420
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IF 3.344
Zhengkai Chen,Weijun Yang,Lijun Xu,Lili Zhang,Maozhong Miao,Hongjun Ren
Graphical Highly substituted 2-hydroxyflavanones can be obtained through a tandem O -arylation/hydroxylation process from triazenylaryl-substituted diketones in the presence of a Lewis acid. A transition-metal-free tandem O -arylation/hydroxylation approach has been developed for the efficient synthesis of highly substituted 2-hydroxyflavanones from triazenylaryl-substituted diketones. The intermediate benzopyrylium cation may be involved in these reactions.
研究领域:
有机化学
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药物化学
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DOI
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
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2016
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IF 1.835
Yingying Shan,Mengfan Fu,Weidong Yan
The solubilities of 4′,5,7-triacetoxyflavanone in eight different alcohols, 2-methoxyethanol, 2-propoxyethanol, 2-butoxyethanol, ethyl acetate, tetrahydrofuran, and acetone have been measured with an HPLC (high-performance liquid chromatography) analysis method at the experimental temperature from 278.2 to 318.2 K. The solubilities of 4′,5,7-triacetoxyflavanone in selected solvents increase with an increasing of temperature. The solubilities of 4′,5,7-triacetoxyflavanone were correlated with the modified Apelblat equation and universal quasichemical (UNIQUAC) equation, respectively. The correlated solubilities were in good accordance with the measured data at the experimental temperature. Furthermore, the crystal habits of 4′,5,7-triacetoxyflavanone in selected solvents were studied in this work.
研究领域:
有机化学
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药物化学
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DOI
高影响因子
FITOTERAPIA
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2019
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IF 2.431
Xue Li,Ling-Juan Zhu,Jin-Peng Chen,Chen-Yu Shi,Li-Ting Niu,Xue Zhang,Xin-Sheng Yao
One new flavanonol , demethylmatteucinol ( 1 ), and nine new flavanone glucoside derivatives, matteflavosides H-J ( 2–4 ) and matteuinterates A-F ( 5 – 10 ), were isolated from the rhizomes of Matteuccia intermedia C.Chr., along with 21 known flavanones ( 11 − 31 ). Notably, all of them contain C -methylation in the A-ring. The structures of the compounds were elucidated by spectroscopic methods and chemical derivatization. The α -glycosidase inhibition assay indicated that compounds 12 – 17 showed potent inhibitory activity with IC 50 values of 12.4–69.7 μM, which suggested their hypoglycemic effect.
研究领域:
植物化学
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药理学
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DOI
高影响因子
GREEN CHEMISTRY
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2025
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IF 9.2
Si-Yu Zhu,Na Li,Zhi-Hua Liu,Ying-Jin Yuan,Bing-Zhi Li
Flavonoids, such as homoeriodictyol derivatives, hold significant value in nutraceuticals, foods, and pharmaceuticals. Microbial synthesis of these products has emerged as a powerful approach due to its sustainability and environmental friendliness. However, constructing microbial cell factories of homoeriodictyol derivatives is often challenged by the lack of biosynthesis pathway and the poor performance of endogenous metabolic networks. Here, an efficient Saccharomyces cerevisiae cell factory was designed and metabolically engineered for the de novo biosynthesis of homoeriodictyol 7-O-glucoside. Relieving the feedback inhibition and overexpressing the key enzymes successfully achieved the biosynthesis of homoeriodictyol with a titer of 174.0 mg/L. Enzyme screening strategies prospected missing glycosyltransferases and unveiled the homoeriodictyol 7-O-glucoside synthesis pathway for the first time. Blocking glycoside hydrolysis pathway improved the titer of homoeriodictyol 7-O-glucoside by a substantial 7.2-fold. Metabolically regulating NADPH regeneration alleviated the intermediate accumulation by 91.3%, while strengthening uridine diphosphate-glucose and substrate supply further boosted the homoeriodictyol 7-O-glucoside production. Together, these advancements led to a record homoeriodictyol 7-O-glucoside titer of 600.2 mg/L and the yield of 12.2 mg/g glucose. Overall, the versatile S. cerevisiae cell factory shows the potential to synthesize homoeriodictyol 7-O-glucoside, contributing to the green and sustainable production of natural products.
研究领域:
合成生物学
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代谢工程学
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高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
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2018
·Vol. 98
·期 13
·4885-4894
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IF 2.379
Lei Deng,Ai-Min Shi,Qiang Wang
INTRODUCTION Peanut stems and leaves (PSL) have traditionally been used as both a special food and a herbal medicine in Asia. The sedative–hypnotic and anxiolytic effects of PSL have been recorded in classical traditional Chinese literature, and more recently by many other researchers. In a previous study, four sleep-related ingredients (linalool, 5-hydroxy-4′,7-dimethoxyflavanone, 2′- O -methylisoliquiritigenin and ferulic acid), among which 5-hydroxy-4′,7-dimethoxyflavanone and 2′- O -methylisoliquiritigenin were newly found in Arachis species, were screened by ultrahigh-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS). In the current study, quantitative examination of the above four ingredients was conducted. Serious fundamental functional studies were done in mice, including locomotor activity, direct sleep tests, pentobarbital-induced sleeping time tests, subthreshold dose of pentobarbital tests and barbital sodium sleep incubation period tests, to determine the material base for the sedative–hypnotic and anxiolytic effects of aqueous extracts of PSL. Furthermore, neurotransmitter levels in three brain regions (cerebrum, cerebellum and brain stem) were determined using UHPLC coupled with triple-quadrupole mass spectrometry (UHPLC/QQQ-MS) in order to elucidate the exact mechanism of action. RESULTS Aqueous extract of PSL at a dose of 500 mg kg −1 (based on previous experience), along with different concentrations of the above four functional ingredients (189.86 µg kg −1 linalool, 114.75 mg kg −1 5-hydroxy-4′,7-dimethoxyflavanone, 32.4mg kg −1 2′- O -methylisoliquiritigenin and 44.44 mg kg −1 ferulic acid), had a sedative−hypnotic effect by affecting neurotransmitter levels in mice. CONCLUSION The data demonstrate that these four ingredients are the key functional factors for the sedative–hypnotic and anxiolytic effects of PSL aqueous extracts and that these effects occur via changes in neurotransmitter levels and pathways. © 2018 Society of Chemical Industry
研究领域:
药理学
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植物化学
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DOI
高影响因子
BIOMEDICINE & PHARMACOTHERAPY
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2022
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IF 7.419
Hui Jin,Ningning Jiang,Wenshu Xu,Zhongyuan Zhang,Yang Yang,Jingmin Zhang,Hui Xu
In this experimental study, we evaluated the protective effects and the safety of main flavanones derived from Rhizoma Drynariae (Gusuibu) in vitro and in vivo. The MTT assay showed that compared with vehicle treatment, treatment with such flavanones as neoeriocitrin, naringin, and naringenin significantly promoted the viability of osteocyte-like cells. Quantitative real-time PCR showed that neoeriocitrin and naringin significantly attenuated mRNA expressions of RANKL and SOST in osteocyte-like cells. In rats with retinoic acid-induced osteoporosis, total flavonoid of Rhizoma Drynariae (TFRD) , naringin, and naringenin significantly increased the number of trabeculae and improved trabecular bone structure compared with no treatment, without affecting liver and renal function. In addition, naringenin and naringin administration significantly increased bone mineral density of femur neck and femur shaft compared with the osteoporotic model rats. Western blot analysis showed that naringenin and naringin significantly attenuated protein expressions of bone resorption-related factors (TRAP, RANKL and RANK), and inhibited sclerostin expression compared with the osteoporotic model rats. On the other hand, naringin markedly increased protein expressions of ALP and PTH1R, and TFRD and naringenin also promoted PTH1R expression compared with the model rats. In conclusion, such flavanones as naringenin and naringin exhibited antiresorptive properties, and naringin particularly showed potential benefits for osteoporosis treatment.
研究领域:
药理学
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骨科
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分子生物学
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DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
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2022
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IF 6.449
Qingjie Wang,Yang Jiang,Xinyu Mao,Wanwen Yu,Jinkai Lu,Li Wang
Age affects the content of flavonoids in ginkgo ( Ginkgo biloba L.) leaves, such that only 1-to-5-year-old ginkgo leaves are suitable for the extraction of medicinal compounds. Nevertheless, the relationship between age and flavonoids in ginkgo leaves is unclear. In this study, we compared 1-to-7-year-old ginkgo trees, and found that the flavonoid content decreased with age. The total flavonol aglycones content of 1-year old ginkgo was 9.88 ± 0.27 mg/g, significantly higher than those of 4- and 7-year-old gingko, and there was a marked difference in quercetin content. Next, we extensively compared the transcriptome and metabolome in leaves of 1-, 4-, and 7-year-old ginkgo. Metabolome profiles showed that flavonoid metabolites were the most abundant in different metabolities, and 82 % of the flavonoids exhibited a decreasing trend with increasing age. Downregulation of key structural genes (chalcone synthase, CHS ; flavanone 3-hydroxylase, F3H ; flavonol synthase , FLS ) in the flavonoid biosynthesis pathway may explain the decreased flavonoid content with age. Furthermore, GO and KEGG analysis revealed photosynthesis- and hormone-related genes were downregulated with increasing age, implying that photosynthesis, salicylic acid, and jasmonic acid influence the flavonoid content. These results provide a theoretical basis for leaves ginkgo seedlings and new clues for understanding how age regulates flavonoids.
研究领域:
植物学
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药理学
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分子生物学
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植物生理学
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DOI
高影响因子
CATALYSIS LETTERS
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2015
·Vol. 145
·期 10
·1830-1836
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IF 2.307
Zhou Yan,Huang Wei,Chen Xiang-Shu,Song Zhi-Bin,Tao Duan-Jian
Abstract Several tetramethylguanidinum-based ionic liquids (TMGILs) were prepared, characterized and used as catalysts in one-pot synthesis of flavanones. The results indicated that TMGILs composed of phenolate anion was beneficial for one-pot synthesis of flavanones, and [TMG][4-MeO–PhO] induced the good yields of flavanones owing to the electron-donating effect of methoxy substituent on phenolate anion. Furthermore, [TMG][4-MeO–PhO] was found to be used repetitively at least five times without obvious decrease in activity and quantity. Graphical Abstract
研究领域:
有机化学
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催化
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合成化学
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DOI
高影响因子
JOURNAL OF CHROMATOGRAPHY A
·
2023
·
IF 4.1
Wenhui Li,Yu Huang,Yuqian Xiang,Xiaohui Yan,Yanshuo Li,Dapeng Wu
In this work, the vacuum-assisted thermal bonding method was proposed for the covalent coupling of β-cyclodextrin (β-CD) (CD-CSP), hexamethylene diisocyanate cross-linked β-CD (HDI-CSP) and 3, 5-dimethylphenyl isocyanate modified β-CD (DMPI-CSP) onto the isocyanate silane modified silica gel. Under vacuum conditions, the side reaction due to the water residue from the organic solvent, air, reaction vessels and silica gel could be avoided, and the optimal temperature and time of vacuum-assisted thermal bonding method were determined as 160°C and 3 h. These three CSPs were characterized by FT-IR, TGA, elemental analysis and the nitrogen adsorption-desorption isotherms. The surface coverage of CD-CSP and HDI-CSP on silica gel was determined as ∼0.2 μmol m −2 , respectively. The chromatographic performances of these three CSPs were systematically evaluated by separating 7 flavanones, 9 triazoles and 6 chiral alcohols enantiomers under the reversed-phase condition. It was found that the chiral resolution ability of CD-CSP, HDI-CSP and DMPI-CSP was complementary to each other. Among them, CD-CSP could separate all 7 flavanones enantiomers with the resolution of 1.09–2.48. HDI-CSP had a good separation performance for triazoles enantiomers with one chiral center. DMPI-CSP showed excellent separation performance for chiral alcohol enantiomers, among which the resolution of trans-1, 3-diphenyl-2-propen-1-ol reached 12.01. Generally, the vacuum-assisted thermal bonding had been demonstrated as a direct and efficient method for the preparation of chiral stationary phases of β-CD and its derivatives.
研究领域:
分析化学
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色谱学
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材料科学
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DOI
PubMed
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
·
2020
·
IF 3.209
Xinhui Wang,Rui Li,Xiangyue Liu,Shan Huang,Bin Li,Honglei Wang,Xin Chai,Yuefei Wang
Garcinia kola seeds play an important role in African traditional medicine, which are widely used to treat stomachache, gastritis, malaria, venereal diseases and laryngitis. The habitats, specification, different parts of seeds and slicing process are important factors that affect the quality of Garcinia kola seeds. Interestingly, brownish yellow or brownish red spots were derived from gum resin exuded during slicing, whose chemical constituents have not been elucidated. A rapid high performance liquid chromatography method was established for quantitative study of four main biflavanones (GB-2, GB-1, kolaflavanone and GB-1a) in Garcinia kola seeds. We found that the content of the tested biflavanones was slightly different in Garcinia kola seeds from different habitats, while the seeds weight showed no obvious influence on the biflavanones content from the same habitat. With the aid of “spider-web” mode, we unveiled that the accumulation of biflavanones mainly occurred in seed kernels. Furthermore, slices thickness (1–2 mm) was optimized by comprehensive evaluation of biflavanones’ content, moisture, cutting-time and drying-time to efficiently dry the slices. By employing of ultra-high performance liquid chromatography coupled with electrospray ionization quadrupole Orbitrap high resolution mass spectrometry (UHPLC/ESI Q-Orbitrap MS), garcinoic acid and its derivatives were successfully identified in gum resin, conducing to the interesting finding about the distribution of biflavanones and derivatives of garcinoic acid in Garcinia kola seeds. Generally, our findings in this research could contribute to standardizing the process of harvesting, processing and quality control for Garcinia kola seeds, and help better development and utilization of this important medicinal plant.
研究领域:
药用植物学
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分析化学
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传统医学
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植物科学
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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）