1.Isolation and identification of chemical constituents from aerial parts of Glycyrrhiza uralensis.
Guan-Hua CHANG ; Lu ZHANG ; Jie CUI ; Wen-Quan WANG ; Jun-Ling HOU
China Journal of Chinese Materia Medica 2023;48(16):4413-4420
The present study investigated the chemical constituents from the aerial parts of Glycyrrhiza uralensis. The ethanol extract of the aerial parts of G. uralensis was separated and purified by different column chromatographies such as macroporous resin, silica gel, and Sephadex LH-20, and through preparative HPLC and recrystallization. Thirteen compounds were isolated and identified as(2S)-6-[(Z)-3-hydroxymethyl-2-butenyl]-5,7,3'-trihydroxy-4'-methoxy-dihydroflavanone(1),(2S)-8-[(E)-3-hydroxymethyl-2-butenyl]-5,7,3',5'-tetrahydroxy-dihydroflavanone(2), α,α'-dihydro-5,4'-dihydroxy-3-acetoxy-2-isopentenylstilbene(3), 6-prenylquercetin(4), 6-prenylquercetin-3-methyl ether(5), formononetin(6), 3,3'-dimethylquercetin(7), chrysoeriol(8), diosmetin(9),(10E,12Z,14E)-9,16-dioxooctadec-10,12,14-trienoic acid(10), 5,7,3',4'-tetrahydroxy-6-prenyl-dihydroflavanone(11), naringenin(12), dibutylphthalate(13). Compounds 1-3 are new compounds, and compounds 10 and 13 are isolated from aerial parts of this plant for the first time.
Glycyrrhiza uralensis/chemistry*
;
Plant Components, Aerial/chemistry*
2.New di-spirocyclic labdane diterpenoids from the aerial parts of Leonurus japonicus.
Xinxin CAO ; Xinxin WANG ; Yu ZHANG ; Defeng XU ; Xiuqing SONG ; Jinhai YU ; Jie BAO ; Junsheng ZHANG ; Hua ZHANG
Chinese Journal of Natural Medicines (English Ed.) 2023;21(7):551-560
Phytochemical investigation on the ethanol extract of a well-known medicinal herb Leonurus japonicus, led to the separation of 18 labdane type diterpenoids (1-18). Through comprehensive spectroscopic analyses and quantum chemical calculations, these compounds were structurally characterized as six new interesting 5,5,5-di-spirocyclic ones (1-6), two new (7 and 8) and six known (13-18) interesting 6,5,5-di-spirocyclic ones, a new rare 14,15-dinor derivative (9), and three new ones incorporating a γ-lactone unit (10-12). An in vitro neuroprotective assay in RSC96 cells revealed that compounds 7 and 12 exhibited neuroprotective activity in a concentration-dependent way, comparable to the reference drug N-acetylcysteine.
Magnetic Resonance Spectroscopy
;
Leonurus/chemistry*
;
Plants, Medicinal
;
Diterpenes/chemistry*
;
Plant Components, Aerial
;
Molecular Structure
3.Spectrum-effect relationships on enriching blood activities of aerial parts of Angelica sinenis.
Jie-Li LIU ; Xia MA ; Ying ZHANG ; Dong-Mei XING ; Shu-Fang DENG ; Yu-Jing SUN ; Ya-Li WANG
China Journal of Chinese Materia Medica 2019;44(7):1416-1424
Ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry(UPLC-Q-TOF-MS) was used to establish the chromatography fingerprint for aerial parts of Angelica sinenis(AAS) from 10 different places. Acetyl-phenyl-hydrazine(APH) was used to duplicate the mouse model of blood deficiency. Then partial least squares regression was used to investigate the spectrum-effect relationship between the relative contents and the data of enriching blood pharmacodynamics efficacy. The results showed that the three groups of high, medium and low doses of AAS had certain enriching blood activities(P<0.05), and the high dose group had the best effect(P<0.01). The contribution degree of the AAS to enriching blood activities of each common peaks were determined by PLS regression coefficient. Among them, 7 common peaks, including P17(unknown), P18(unknown), P19(unknown), P28(alisol B 23-acetate or its isomer), N5(luteolin), N11(1-caffeoylquinicacid,1-O-caffeoylquinic acid) and N14(unknown), contributed significantly to the effect of enriching blood activities. This paper dealed with the investigation on the spectrum-effect relationship between enriching blood activities and LC-MS chromatography fingerprint of AAS, and determination of the effective compositions of AAS with enriching blood activities. It provided theoretical foundation for the comprehensive development and utilization of AAS.
Angelica
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chemistry
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Animals
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Chromatography, High Pressure Liquid
;
Drugs, Chinese Herbal
;
pharmacology
;
Mass Spectrometry
;
Medicine, Chinese Traditional
;
Mice
;
Plant Components, Aerial
;
chemistry
4.Studies on chemical constituents of Isodon henryi.
Ling-Xia ZHANG ; Ya-Lin LIU ; Hong WU ; Sui-Qing CHEN ; Li-Ping DAI
China Journal of Chinese Materia Medica 2019;44(2):319-323
The chemical constituents of the water extraction of the aerial parts of Isodon henryi were investigated by various chromatographic methods including D-101 macroporous adsorptive resins,silica gel,sephadex LH-20,and semi-preparative HPLC. As a result,ten compounds were separated and purified. By analyses of the UV,IR,MS,NMR spectra,their structures were determined as rabdosinate( 1),lasiokaurin( 2),epinodosinol( 3),rabdosichuanin C( 4),epinodosin( 5),hebeirubescensin k( 6),rubescensin C( 7),enmenol( 8),oridonin( 9),and enmenol-1-β-glucoside( 10). Compounds 1-8 and 10 were isolated from I. henryi for the first time. Compounds 2 and 9 showed inhibitory effects against four tumor cells,with IC50 values of 2. 25-9. 32 μmol·L-1.
Isodon
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chemistry
;
Magnetic Resonance Spectroscopy
;
Molecular Structure
;
Phytochemicals
;
analysis
;
Plant Components, Aerial
;
chemistry
;
Plant Extracts
;
chemistry
5.New flavonoids and methylchromone isolated from the aerial parts of Baeckea frutescens and their inhibitory activities against cyclooxygenases-1 and -2.
Jun-Neng ZHOU ; Ming YAN ; Peng GAO ; Ji-Qin HOU ; Thi-Anh PHAM ; Hao WANG
Chinese Journal of Natural Medicines (English Ed.) 2018;16(8):615-620
In the present study, we carried out a phytochemical investigation of the ethanol extract of the aerial parts of Baeckea frutescens, which resulted in the isolation of two new flavonoid glycosides, myricetin 3-O-(5″-O-galloyl)-α-L-arabinofuranoside (1), 6-methylquercetin 7-O-β-D-glucopyranoside (2), one new methylchromone glycoside, 7-O-(4', 6'-digalloyl)-β-D-glucopyranosyl-5-hydroxy-2-methylchromone (3), together with three known compounds (4-6). The structures of these isolated compounds were established on the basis of 1D and 2D NMR techniques and chemical methods. The anti-inflammatory activities of the compounds 1-6 were evaluated for their inhibitory effects against cyclooxygenases-1 and -2 in vitro. Compounds 1-6 showed potent COX-1 and COX-2 inhibiting activities in vitro with IC values ranging from 1.95 to 5.54 μmol·L and ranging from 1.01 to 2.27 μmol·L, respectively.
Anti-Inflammatory Agents
;
chemistry
;
isolation & purification
;
Cyclooxygenase 1
;
chemistry
;
Cyclooxygenase 2
;
chemistry
;
Cyclooxygenase Inhibitors
;
chemistry
;
isolation & purification
;
Flavonoids
;
chemistry
;
isolation & purification
;
Molecular Structure
;
Myrtaceae
;
chemistry
;
Plant Components, Aerial
;
chemistry
;
Plant Extracts
;
chemistry
;
isolation & purification
6.Scopariusols L-T, nine new ent-kaurane diterpenoids isolated from Isodon scoparius.
Hua-Yi JIANG ; Xiao-Nian LI ; Han-Dong SUN ; Hong-Bin ZHANG ; Pema-Tenzin PUNO
Chinese Journal of Natural Medicines (English Ed.) 2018;16(6):456-464
Nine new ent-kaurane diterpenoids, named scopariusols L-T (1-9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compound 1 was active against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC value of 0.6 μmol·L.
Animals
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Antineoplastic Agents, Phytogenic
;
chemistry
;
isolation & purification
;
pharmacology
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Cell Line, Tumor
;
Crystallography, X-Ray
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Diterpenes, Kaurane
;
chemistry
;
isolation & purification
;
pharmacology
;
Drug Screening Assays, Antitumor
;
Drugs, Chinese Herbal
;
chemistry
;
isolation & purification
;
pharmacology
;
HL-60 Cells
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Humans
;
Isodon
;
chemistry
;
Lipopolysaccharides
;
pharmacology
;
Macrophages
;
drug effects
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Mice
;
Molecular Structure
;
Nitric Oxide
;
biosynthesis
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Nuclear Magnetic Resonance, Biomolecular
;
Plant Components, Aerial
;
chemistry
;
RAW 264.7 Cells
7.Neuroprotective effect of the ethanol extract of Artemisia capillaris on transient forebrain ischemia in mice via nicotinic cholinergic receptor.
Huiyoung KWON ; Ji Wook JUNG ; Young Choon LEE ; Jong Hoon RYU ; Dong Hyun KIM
Chinese Journal of Natural Medicines (English Ed.) 2018;16(6):428-435
Artemisia capillaris Thunberg is a medicinal plant used as a traditional medicine in many cultures. It is an effective remedy for liver problems including hepatitis. Recent pharmacological reports have indicated that Artemisia species can exert various neurological effects. Previously, we reported a memory-enhancing effect of Artemisia species. However, the mechanisms underlying the neuroprotective effect of A. capillaris (AC) are still unknown. In the present study, we investigated the effect of an ethanol extract of AC on ischemic brain injury in a mouse model of transient forebrain ischemia. The mice were treated with AC for seven days, beginning one day before induction of transient forebrain ischemia. Behavioral deficits were investigated using the Y-maze. Nissl and Fluoro-jade B staining were used to indicate the site of injury. To determine the underlying mechanisms for the drug, we measured acetylcholinesterase activity. AC (200 mg·kg) treatment reduced transient forebrain ischemia-induced neuronal cell death in the hippocampal CA1 region. The AC-treated group also showed significant amelioration in the spontaneous alternation of the Y-maze test performance, compared to that in the untreated transient forebrain ischemia group. Moreover, AC treatment showed a concentration-dependent inhibitory effect on acetylcholinesterase activity in vitro. Finally, the effect of AC on forebrain ischemia was blocked by mecamylamine, a nonselective nicotinic acetylcholine receptor antagonist. Our results suggested that in a model of forebrain ischemia, AC protected against neuronal death through the activation of nicotinic acetylcholine receptors.
Acetylcholinesterase
;
metabolism
;
Animals
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Artemisia
;
Cell Death
;
drug effects
;
Cholinergic Antagonists
;
pharmacology
;
Disease Models, Animal
;
Ethanol
;
chemistry
;
Hippocampus
;
pathology
;
physiopathology
;
Ischemic Attack, Transient
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drug therapy
;
pathology
;
physiopathology
;
Male
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Mecamylamine
;
pharmacology
;
Memory
;
drug effects
;
Mice
;
Mice, Inbred C57BL
;
Models, Neurological
;
Neuroprotective Agents
;
administration & dosage
;
pharmacology
;
Phytotherapy
;
Plant Components, Aerial
;
chemistry
;
Plant Extracts
;
administration & dosage
;
pharmacology
;
Receptors, Cholinergic
;
metabolism
8.Three resin glycosides isolated from Argyreia acuta, including two isomers.
Jia-Yan HU ; Xiu-Hong WU ; Yong-Qin YIN ; Jie-Tao PAN ; Bang-Wei YU
Chinese Journal of Natural Medicines (English Ed.) 2018;16(5):354-357
In the present study, three compounds were isolated from Argyreia acuta, among them, compounds 1 and 2 were new and Compounds 1 and 3 were isomers. They were separated by several types of columns, such as normal phase, RP, size exclusion and preparative HPLC, and their structures were elucidated by several spectroscopic methods, such as 1D- and 2D-NMR and HR-TOF-MS.
Convolvulaceae
;
chemistry
;
Drugs, Chinese Herbal
;
chemistry
;
Glycosides
;
chemistry
;
isolation & purification
;
Isomerism
;
Mass Spectrometry
;
Molecular Structure
;
Nuclear Magnetic Resonance, Biomolecular
;
Plant Components, Aerial
;
chemistry
;
Resins, Plant
;
chemistry
;
isolation & purification
;
Spectrophotometry
9.Chemical constituents from Gnaphalium affine and their xanthine oxidase inhibitory activity.
Wei ZHANG ; Chun-Zhen WU ; Si-Yang FAN
Chinese Journal of Natural Medicines (English Ed.) 2018;16(5):347-353
Gnaphalium affine D. Don, a medicinal and edible plant, has been used to treat gout in traditional Chinese medicine and popularly consumed in China for a long time. A detailed phytochemical investigation on the aerial part of G. affine led to the isolation of two new esters of caffeoylquinic acid named (-) ethyl 1, 4-di-O-caffeoylquinate (1) and (-) methyl 1, 4-di-O-caffeoylquinate (2), together with 35 known compounds (3-37). Their structures were elucidated by spectroscopic data and first-order multiplet analysis. All the isolated compounds were tested for their xanthine oxidase inhibitory activity with an in vitro enzyme inhibitory screening assay. Among the tested compounds, 1 (IC 11.94 μmol·L) and 2 (IC 15.04 μmol·L) showed a good inhibitory activity. The current results supported the medical use of the plant.
Adenine
;
analogs & derivatives
;
chemistry
;
isolation & purification
;
Drugs, Chinese Herbal
;
chemistry
;
pharmacology
;
Enzyme Activation
;
drug effects
;
Flavonoids
;
chemistry
;
isolation & purification
;
Gnaphalium
;
chemistry
;
Gout Suppressants
;
chemistry
;
isolation & purification
;
pharmacology
;
Hydroxybenzoates
;
chemistry
;
isolation & purification
;
Molecular Structure
;
Nuclear Magnetic Resonance, Biomolecular
;
Phytochemicals
;
chemistry
;
isolation & purification
;
pharmacology
;
Plant Components, Aerial
;
chemistry
;
Plant Extracts
;
chemistry
;
isolation & purification
;
pharmacology
;
Quinic Acid
;
analogs & derivatives
;
chemistry
;
isolation & purification
;
Xanthine Oxidase
;
antagonists & inhibitors
10.Lignans and diterpenes isolated from Tirpitzia ovoidea and their biological activities.
Xue-Yan YANG ; Yi-Fan ZHANG ; Li-Jia LIU ; Yi WANG ; Ming-Ying SHANG ; Feng XU ; Guang-Xue LIU ; Shao-Qing CAI
Chinese Journal of Natural Medicines (English Ed.) 2017;15(12):938-943
A new lignan, tirpitzin A (17) together with 20 known compounds (1-16, and 18-21) were isolated from the ethyl acetate soluble fraction of ethanol extract of the aerial parts of Tirpitzia ovoidea. The structure of new compound was elucidated by means of spectroscopic analysis. Of the known compounds, 7-21 were isolated from Linaceae family for the first time. The pharmacological activity of the crude extracts was tested using a mouse inflammation model induced by dimethyl benzene. The results demonstrated that the ethyl acetate soluble fraction had anti-inflammatory activity. Moreover, the cytotoxic and anti-inflammatory activities of some compounds were studied. The new compound 17 showed moderate cytotoxic effect against BxPC-3 cell line (IC = 19.51μmol·L) and Compound 10 showed significant cytotoxicity against HepG2, HL-60, U87 and BxPC-3 cell lines with IC values in the range 4.2-8.3μmol·L. Additionally, Compounds 2, 10, 11, and 13 exhibited potent inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages at the concentration of 50μmol·L.
Animals
;
Anti-Inflammatory Agents
;
chemistry
;
pharmacology
;
Cell Line, Tumor
;
Cell Survival
;
drug effects
;
Disease Models, Animal
;
Diterpenes
;
chemistry
;
pharmacology
;
toxicity
;
HL-60 Cells
;
Hep G2 Cells
;
Humans
;
Inhibitory Concentration 50
;
Lignans
;
chemistry
;
pharmacology
;
toxicity
;
Linaceae
;
chemistry
;
Macrophages
;
drug effects
;
Mice
;
Nitric Oxide
;
metabolism
;
Plant Components, Aerial
;
chemistry
;
Plant Extracts
;
chemistry
;
pharmacology
;
toxicity
;
RAW 264.7 Cells

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