1.Polyhydroxylated eudesmane sesquiterpenoids and sesquiterpenoid glucoside from the flower buds of Tussilago farfara.
Yu-Peng LI ; Kang YANG ; Hui MENG ; Tao SHEN ; Hua ZHANG
Chinese Journal of Natural Medicines (English Ed.) 2022;20(4):301-308
Chemical fractionation of the n-BuOH partition, which was generated from the EtOH extract of the flower buds of Tussilago farfara, afforded a series of polar constituents including four new sesquiterpenoids (1-4), one new sesquiterpenoid glucoside (5) and one known analogue (6) of the eudesmane type, as well as five known quinic acid derivatives (7-11). Structures of the new compounds were unambiguously characterized by detailed spectroscopic analyses, with their absolute configurations being established by X-ray crystallography, electronic circular dichroism (ECD) calculation and induced ECD experiments. The inhibitory effect of all the isolates against LPS-induced NO production in murine RAW264.7 macrophages was evaluated, with isochlorogenic acid A (7) showing significant inhibitory activity.
Animals
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Flowers/chemistry*
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Glucosides/pharmacology*
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Mice
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Sesquiterpenes/pharmacology*
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Sesquiterpenes, Eudesmane/pharmacology*
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Tussilago/chemistry*
2.Research progress on mechanism of gastrodin and p-hydroxybenzyl alcohol on central nervous system.
Zhi-Long ZHANG ; Yu-Gang GAO ; Pu ZANG ; Pei-Pei GU ; Yan ZHAO ; Zhong-Mei HE ; Hong-Yan ZHU
China Journal of Chinese Materia Medica 2020;45(2):312-320
Gastrodin(GAS) and p-hydroxybenzyl alcohol(HBA) are extracts of dried tubers of Gastrodia elata, which is the material basis for its efficacy and belongs to phenolic compounds. Modern pharmacology studies have shown that they have significant effects on central nervous system diseases, such as insomnia, convulsions, depression, ischemic stroke, anxiety, and cognitive impairment, and these diseases are closely related to neurotransmitters and cytokines. This paper described various mechanisms of GAS and HBA monomer components on the central nervous system. They alleviate hippocampal neuronal toxicity mainly by regulating a variety of neurotransmitters, such as acetylcholine, glutamic acid(GLU), γ-aminobutyric acid(GABA), serotonin(5-HT), dopamine(DA), norepinephrine(NE), 5-indoleacetic acid(5-HIAA), high vanillic acid(HVA) and dihydroxyphenylacetic acid(DOPAC), pro-inflammatory cell growth factors, such as IL-1β, IL-6 and TNF-α and relevant receptor functions, and exert neuropharmacological effects by effectively increasing mRNA expressions of brain neurotrophic factors, such as BDNF and GDNF, and further inhibiting the apoptosis of damaged neurons. This paper summarized various mechanisms on the central nervous system, which provides a scientific basis for the further research of the neuropharmacological mechanism of GAS and HBA and the development of new drugs and functional food.
Benzyl Alcohols/pharmacology*
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Central Nervous System/drug effects*
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Gastrodia/chemistry*
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Glucosides/pharmacology*
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Humans
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Plant Extracts/pharmacology*
3.Advances in research on pharmacodynamics and chemical conversion of catalpol.
Yan-fei LIU ; Yu ZHAO ; Xue-sen WEN ; Qi-ting DONG
China Journal of Chinese Materia Medica 2007;32(12):1128-1130
Catalpol is a active component in Rehmannia Root, and its pharmacological effects are extensive. In this paper its effects and chemical changes were summarized. This will offer the reference for further research work catalpol.
Animals
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Antineoplastic Agents, Phytogenic
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pharmacology
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Drugs, Chinese Herbal
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chemistry
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isolation & purification
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pharmacology
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Glucosides
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chemistry
;
isolation & purification
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pharmacology
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Humans
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Hypoglycemic Agents
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pharmacology
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Iridoid Glucosides
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Iridoids
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chemistry
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isolation & purification
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pharmacology
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Neuroprotective Agents
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pharmacology
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Plants, Medicinal
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chemistry
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Rehmannia
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chemistry
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Technology, Pharmaceutical
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methods
4.Research advances in pharmacology of aucubin and aucubigenin.
Zhen KANG ; Wei-Hua WU ; Jun-Jie WANG ; Dong-Sheng OUYANG
China Journal of Chinese Materia Medica 2007;32(24):2585-2587
The advances in the research on pharmacological activities of aucubin have been summarized in the last ten years. Aucubin is one of active components of Chinese medicinal herbs such as Eucommia ulmoides and has been shown wide pharmacological activities including hepatoproective, antitoxicanti-inflammatory, antioxidant, antiaging, antiosteoporosis and neurotrophic and should be further researched and utilized.
Aging
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drug effects
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Animals
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Anti-Inflammatory Agents
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pharmacology
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Antioxidants
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pharmacology
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Eucommiaceae
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chemistry
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Glucosides
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chemistry
;
isolation & purification
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pharmacology
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Iridoid Glucosides
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Iridoids
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chemistry
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isolation & purification
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pharmacology
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Molecular Structure
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Plants, Medicinal
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chemistry
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Pyrans
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chemistry
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isolation & purification
;
pharmacology
5.Production of gastrodin through biotransformation of p-hydroxybenzaldehyde by cell suspension cultures of Datura tatula L.
Jia-Shun GONG ; Wei-Peng MA ; Jun-Xue PU ; Shu-Guan XU ; Shuang-Qing ZHENG ; Chun-Jie XIAO
Chinese Journal of Biotechnology 2006;22(5):800-804
The conversion of exogenous p-hydroxybenzaldehyde to p-hydroxy-methyl-phenol-beta-D-glucoside (gastrodin) was studied by using cell suspension culture of Datura tatula L. The chemical structure of this synthesized gastrodin was identified based on the spectral analysis and chemical evidence. The conversion procedure of p-hydroxybenzaldehyde into gastrodin by D. tatula L. cell suspension cultures was established. The synthesized gastrodin (II) was isolated from the ferment liquor and identified by spectral analysis. At the same time, the p-hydroxybenzyl alcohol (I) converted through biotransformation of p-hydroxybenzaldehyde by cell suspension cultures of D. tatula L. was also isolated and identified. The efficiency of glucosylation of p-hydroxybenzaldehyde was remarkably enhanced by adding salicylic acid (0.1 mg/L) and keeping the lower pressure (0.001MPa) in 25L airlift loop bioreactor. The biotransformation of exogenous p-hydroxybenzaldehyde to gastrodin by cell suspension culture of D. tatula L. is a promising approach.
Benzaldehydes
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metabolism
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Benzyl Alcohols
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chemistry
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Bioreactors
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Biotransformation
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Datura
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metabolism
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Glucosides
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biosynthesis
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chemistry
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Salicylic Acid
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pharmacology
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Suspensions
6.A new lignan glucoside from stems and branches of Rhododendron ovatum.
China Journal of Chinese Materia Medica 2023;48(2):415-420
Ten lignans were isolated from the ethanol extract of stems and branches of Rhododendron ovatum through column chromatography over silica gel, ODS, Sephadex LH-20, and MCI-gel resin and semi-preparative RP-HPLC. The structures of all compounds were elucidated by extensive spectroscopic data analysis(UV, IR, HR-ESI-MS, ECD and NMR) as(-)-4-epi-lyoniresinol-9'-O-α-L-rhamnopyranoside(1),(+)-lyoniresinol-3α-O-α-L-rhamnopyranoside(2),(+)-5'-methoxyisolariciresinol-9'-O-α-L-rhamnopyranoside(3),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(4),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(5),(-)-4-epi-lyoniresinol-9'-O-β-D-glucopyransoide(6), racemiside(7), neociwujiaphenol(8),(+)-syringaresinol(9), and homohesperitin(10). Among them, compound 1 was a new aryltetralin-type lignan. All the isolated lignans were tested for antioxidant activities in Fe~(2+)-cysteine induced rat liver microsomal lipid peroxidation in vitro, and compounds 8 and 9 showed antioxidant activities on the formation of malondiadehyde(MDA) in rat liver microsomes at 1×10~(-5) mol·L~(-1), with significant inhibitory rates of 75.20% and 91.12%, respectively.
Animals
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Rats
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Glucosides/chemistry*
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Rhododendron
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Antioxidants/pharmacology*
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Lignans/chemistry*
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Plant Stems
7.Progress in studies of pharmacological action and mechanisms of catalpol on brain diease.
Huifeng ZHU ; Dong WAN ; Fen ZHANG
China Journal of Chinese Materia Medica 2009;34(23):2983-2986
Catalpol is a effective components of rehmannia root, it have many pharmacological actions, such as anti-brain ischemia, anti-senile dementia, promoting neuro-remodeling and reducing capillary permeability and so on.
Animals
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Brain Diseases
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drug therapy
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genetics
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metabolism
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Drugs, Chinese Herbal
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pharmacology
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Gene Expression
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drug effects
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Glucosides
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pharmacology
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Humans
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Iridoid Glucosides
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Iridoids
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pharmacology
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Rehmannia
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chemistry
8.Rubrofusarin glucosides of Berchemia polyphylla var. leioclada and their scavenging activities for DPPH radical.
Yongshuai JING ; Juan YANG ; Lanfang WU ; Zhendong ZHANG ; Li FANG
China Journal of Chinese Materia Medica 2011;36(15):2084-2087
OBJECTIVETo study the rubrofusarin glucosides from whole plants of Berchemia polyphylla var. leioclada, and their scavenging activities for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.
METHODThe chemical constituents were isolated and purified via repeated silica gel and Sephadex LH-20 column chromatography. Their structures were elucidated by spectral analysis and the compounds were tested for their scavenging activities on DPPH radical.
RESULTThree rubrofusarin glucosides compounds were isolated and identified as rubrofusarin-6-O-beta-D-glucopyranoside (1), rubrofusarin-6-O-beta-D-(6'-O-acetyl) glucopyranoside (2), rubrofusarin-6-O-alpha-L-rhamnosyl-(1-6) -O-beta-D-glucopyranside (3). Three isolated compounds showed strong scavenging activities on DPPH radical, the concentration of half elimination ratio( micromol x L(-1)) of VitC and Compounds 1-3 were 18.2, 40.5, 23.3 and 13.6, respectively.
CONCLUSIONCompounds 1-3 were isolated from this plant for the first time and compound 2 was a new compound. They showed significant antioxidant activity, and the scavenging activity of compound 3 was a little stronger than that of VitC.
Biphenyl Compounds ; metabolism ; Free Radical Scavengers ; chemistry ; pharmacology ; Glucosides ; chemistry ; pharmacology ; Nuclear Magnetic Resonance, Biomolecular ; Picrates ; metabolism ; Pyrones ; chemistry ; pharmacology ; Rhamnaceae ; chemistry
9.Lignans with NO inhibitory activity from Tinospora sinensis.
Jun-Sheng ZHANG ; De-Feng XU ; Xin-Xin CAO ; Yin-Yin WANG ; Hua ZHANG
Chinese Journal of Natural Medicines (English Ed.) 2021;19(7):500-504
Two new lignan glucosides, tinsinlignans A and B (1 and 2), two new oxyneolignans, tinsinlignans C and D (3 and 4), along with one known analogue (5), were isolated from the stems of Tinospora sinensis. The structures of the new compounds were elucidated based on analysis of spectroscopic data, and the absolute configuration of 1 was determined through electronic circular dichroism (ECD) calculation based on the time-dependent density functional theory (TD-DFT). Compounds 1-4 were evaluated for their inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells and compounds 1 and 2 exhibited moderate inhibitory activities with IC
Animals
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Glucosides/pharmacology*
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Lignans/pharmacology*
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Lipopolysaccharides
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Mice
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Molecular Structure
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Nitric Oxide
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Phytochemicals/pharmacology*
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RAW 264.7 Cells
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Tinospora/chemistry*