1.Chemical constituents from stems and leaves of Mycetia hainanensis and their anti-rheumatoid arthritis activities.
Xiao-Ya FU ; Jia-Yi HU ; Jing-Su YU ; Yan-Zhi LIU ; Ke-Jin JIANG ; Bing-Yan SUN ; Yan-Ping LIU ; Yan-Hui FU
China Journal of Chinese Materia Medica 2024;49(24):6692-6698
The chemical constituents from the stems and leaves of Mycetia hainanensis were isolated by silica gel, ODS gel, and Sephadex LH-20 gel column chromatography and preparative HPLC. The chemical structures of all the isolated compounds were identified on the basis of their physicochemical properties, spectroscopic data, as well as the comparison of their physicochemical and spectroscopic data with the reported data in literature. Twelve compounds were isolated from the 85% ethanol extract of the stems and leaves of M. hainanensis, and they were identified as mycehainanic acid(1), 11-methoxyviburtinal(2), isovaltrate acetoxyhydrin(3), jatamanvaltrate K(4), jatamanin C(5), sarmentol F(6), 4,5-dihydroblumenol A(7), petasitolone(8), xylaguaianol D(9), aristolan-9-en-1-one(10), 3α-hydroxycostic acid(11), and ilicic acid(12). Among them, compound 1 was a new nor-sesquiterpene, and compounds 2-12 were isolated from Mycetia for the first time. In addition, the MTS method was employed to assess the anti-rheumatoid arthritis activities of compounds 1-12 based on their anti-proliferative effects on synoviocytes in vitro. The results showed that compounds 1 and 6-12 exhibited notable anti-rheumatoid arthritis activities, showcasing inhibitory effects on the proliferation of MH7A synovial fibroblast cells with the IC_(50) ranging from(5.27±0.07) to(172.68±0.32)μmol·L~(-1), which were comparable to that of the positive control methotrexate \[IC_(50) of(132.39±0.21)μmol·L~(-1)\].
Plant Leaves/chemistry*
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Plant Stems/chemistry*
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Arthritis, Rheumatoid/physiopathology*
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Humans
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Drugs, Chinese Herbal/isolation & purification*
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Animals
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Cell Line
;
Molecular Structure
2.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
3.Three new coumarins and a new coumarin glycoside from Micromelum integerrimum.
Nan-Kai CAO ; Yue-Mei CHEN ; Si-Si ZHU ; Ke-Wu ZENG ; Ming-Bo ZHAO ; Jun LI ; Peng-Fei TU ; Yong JIANG
Chinese Journal of Natural Medicines (English Ed.) 2021;19(8):621-625
Three new coumarins, integmarins A-C (1-3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside.
Coumarins/isolation & purification*
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Glycosides/isolation & purification*
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Molecular Structure
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Plant Leaves/chemistry*
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Plant Stems/chemistry*
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Rutaceae/chemistry*
4.Analysis and evaluation of dynamic accumulation of multiple bioactive constituents in Spatholobi Caulis.
Yu-Qi MEI ; Li-Fang WEI ; Li-Si ZOU ; Xun-Hong LIU ; Jun-Sheng LI ; Jia-Li CHEN ; Meng-Xia TAN ; Cheng-Cheng WANG ; Zhi-Chen CAI ; Fu-Rong ZHANG
China Journal of Chinese Materia Medica 2020;45(3):584-595
A method was established for simultaneous determination of 21 active constituents including flavanols, isoflavones, flavonols, dihydroflavones, dihydroflavonols, chalcones, pterocarpan, anthocyanidins and phenolic acids in Spatholobi Caulis by ultra fast liquid chromatography with triple quadrupole linear ion trap mass spectrometry(UFLC-QTRAP-MS/MS). Then, it was employed to analyze and evaluate the dynamic accumulation of multiple bioactive constituents in Spatholobi Caulis. The chromatographic separation was performed on a XBridge®C_(18)(4.6 mm×100 mm, 3.5 μm) at 30 ℃ with a gradient elution of 0.3% formic acid aqueous solution-methanol, and the flow rate was 0.8 mL·min~(-1), using multiple-reaction monitoring(MRM) mode. A comprehensive evaluation of the multiple bioactive constituents was carried out by gray correlation analysis(GRA). The 21 target components showed good linearity(r>0.999 0) in the range of the tested concentrations. The average recovery rates of the 21 components were from 97.46% to 103.6% with relative standard deviations less than 5.0%. There were differences in the contents of 21 components in Spatholobi Caulis at diffe-rent harvest periods. Spatholobi Caulis had high quality from early November to early December, which is consistent with the local tradi-tional harvest period. This study reveals the rule of the dynamic accumulation of 21 components in Spatholobi Caulis and provides basic information for the suitable harvest time. At the same time, it provides a new method reference for the comprehensive evaluation of the internal quality of Spatholobi Caulis.
Chromatography, High Pressure Liquid
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Fabaceae/chemistry*
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Phytochemicals/isolation & purification*
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Plant Stems/chemistry*
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Plants, Medicinal/chemistry*
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Tandem Mass Spectrometry
5.Mechanisms of Toxicity and Cardiotoxicity of Alcohol Extract from Root, Stem and Leaf of Chloranthus Serratus.
Shu Ping SUN ; Hong Xing LI ; Xiao Ping ZHANG ; Yun Fei MA ; Mei YANG
Journal of Forensic Medicine 2019;35(2):224-229
Objective To compare the differences of cardiotoxicity of alcohol extract from root, stem and leaf of Chloranthus serratus in the rats, and discuss preliminarily its mechanism of toxicity. Methods Rats were randomly divided into four groups: blank, root alcohol, stem alcohol and leaf alcohol, with 8 in each group. After 14 days of continuous intragastric administration, the body mass change curves were drawn. The cardiac coefficient was calculated. The contents of creatine kinase (CK), creatine kinase isoenzyme (CK-MB), lactate dehydrogenase (LDH) and α-hydroxybutyrate dehydrogenase (α-HBDH) as well as the content changes of oxidative stress indexes - total superoxide dismutase (T-SOD) and malondialdehyde (MDA) in the serum of rats were detected. The cardiac pathomorphology changes in the rats were observed. The expression of intercellular adhesion molecule (ICAM-1) and heme oxygenase (HO-1) in myocardial tissue was detected. Results Body mass growth rate: stem alcohol group was the smallest, followed by leaf alcohol group. The difference of cardiac coefficient of every group had no statistical significance (P>0.05). The myocardial tissues of stem alcohol group suffered the most serious damage, followed by the leaf alcohol group. The contents of CK, CK-MB, LDH and α-HBDH in stem alcohol group increased (P<0.05). The increase of MDA content and decrease of T-SOD content in stem alcohol group had statistical significance compared with the blank group and root alcohol group, while the leaf alcohol group only had statistical significance in the decrease of T-SOD content compared with the blank group (P<0.05). The positive expression of ICAM-1 enhanced and the expression of HO-1 protein decreased in every group after the intervention of different extracts. The change trend was stem alcohol > leaf alcohol > root alcohol group. Conclusion The alcohol extract from the stem has the highest cardiotoxicity, followed by the leaf extract, and its mechanism of toxicity may be related to oxidative stress.
Animals
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Cardiotoxicity
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Ethanol
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Heart/drug effects*
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Malondialdehyde
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Myocardium/metabolism*
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Oxidative Stress/physiology*
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Plant Extracts/toxicity*
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Plant Leaves/chemistry*
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Plant Roots/chemistry*
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Plant Stems/chemistry*
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Random Allocation
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Rats
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Rats, Sprague-Dawley
6.Jatrogricaine A: a new diterpenoid with a 5/6/6/4 carbon ring system from the stems of Jatropha podagrica.
Lin CHEN ; Jia-Luo HUANG ; Lei ZHANG ; Hai-Yan TIAN ; Sheng YIN
Chinese Journal of Natural Medicines (English Ed.) 2019;17(4):298-302
Jatrogricaine A (1), a new diterpenoid possessing a 5/6/6/4 carbon ring system, together with eight known diterpenoids (2-9) were isolated from the stems of Jatropha podagrica. Their structures were elucidated by extensive spectroscopic methods and the absolute configuration of 1 was determined by single crystal X-ray diffraction analysis. All compounds were evaluated for their anti-inflammatory activities in vitro, and compound 3 showed significant inhibitory effects against nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 macrophage cells with an IC of 13.44 ± 0.28 μmol·L, being comparable to the positive control, quercetin (IC 17.00 ± 2.10 μmol·L).
Animals
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Anti-Inflammatory Agents
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chemistry
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pharmacology
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Carbon
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analysis
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Diterpenes
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chemistry
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pharmacology
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Inhibitory Concentration 50
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Jatropha
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chemistry
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Lipopolysaccharides
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toxicity
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Macrophages
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drug effects
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metabolism
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Mice
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Molecular Structure
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Nitric Oxide
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metabolism
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Plant Extracts
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chemistry
;
pharmacology
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Plant Stems
;
chemistry
;
RAW 264.7 Cells
7.Chemical constituents from stems and leaves of Clausena emarginata.
Shi HU ; Jia-Ming GUO ; Wen-Hao ZHANG ; Ming-Ming ZHANG ; Yan-Ping LIU ; Yan-Hui FU
China Journal of Chinese Materia Medica 2019;44(10):2096-2101
The chemical constituents from the stems and leaves of Clausena emarginata were separated and purified by column chromatographies on silica gel,ODS,Sephadex LH-20,and PR-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. emarginata,which were identified as siamenol( 1),murrastanine A( 2),3-formyl-1,6-dimethoxycarbazole( 3),3-methoxymethylcarbazole( 4),3-methylcarbazole( 5),murrayafoline A( 6),3-formylcarbazole( 7),3-formyl-1-hydroxycarbazole( 8),3-formyl-6-methoxycarbazole( 9),murrayanine( 10),murrayacine( 11),girinimbine( 12),nordentatin( 13),chalepin( 14),8-hydroxy-6-methoxy-3-pentylisocoumarin( 15) and ethyl orsellinate( 16). Compounds 1-4,14-16 were isolated from C. emarginata for the first time. Among them,compounds 1,2,15 and 16 were isolated from the genus Clausena for the first time. All isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines: HL-60,SMMC-7721,A-549,MCF-7 and SW480 in vitro. Compounds 12 and 14 showed significant inhibitory effects against various human cancer cell lines with IC_(50) values comparable to those of doxorubicin.
Antineoplastic Agents, Phytogenic
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isolation & purification
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pharmacology
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Cell Line, Tumor
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Clausena
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chemistry
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Doxorubicin
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Humans
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Phytochemicals
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isolation & purification
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pharmacology
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Plant Leaves
;
chemistry
;
Plant Stems
;
chemistry
8.Distribution and accumulation of inorganic elements in Ligusticum chuanxiong.
Li ZHOU ; Man-Xi ZHAO ; Sheng WANG ; Chuan-Zhi KANG ; Lu-Qi HUANG ; Lan-Ping GUO
China Journal of Chinese Materia Medica 2019;44(9):1793-1798
Aiming at the phenomenon of heavy metal Cd exceeding the standard of Chuanxiong medicinal materials,the accumulation of 12 inorganic elements,including heavy metals,in Ligusticum chuanxiong was studied in this paper. It was found that the contents and distribution of most inorganic elements in the stems and leaves of L. chuanxiong were higher than those in the rhizomes at seedling and shooting stages. The content of most elements in rhizome reached the highest at harvest stage,and the distribution ratio of some elements in rhizome was higher than that in stem and leaf at harvest stage. But rhizome,stem and leaf of L. chuanxiong have relatively stable absorption capacity and enrichment effect on different elements,and are less affected by growth period and position. Rhizomes and stems and leaves of L. chuanxiong were enriched with Cd,and stems and leaves also accumulated Pb at seedling stage and stem stage. The absorption capacity of Pb in stems and leaves of L. chuanxiong was higher than that of rhizomes,and the ability of absorbing Cd was less than that of rhizomes at harvest time. The total uptake of Cd and Pb by L. chuanxiong decreased with the prolongation of growth time,but the proportion of Cd and Pb in rhizome increased,so that the content of Cd and Pb increased with the prolongation of growth time.
Cadmium
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analysis
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Drugs, Chinese Herbal
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chemistry
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Ligusticum
;
chemistry
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Metals, Heavy
;
analysis
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Plant Leaves
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chemistry
;
Plant Stems
;
chemistry
;
Rhizome
;
chemistry
9.Difference of alkaloid components between old stems and tender stems of Gelsemium elegans.
Jie WANG ; Jie ZHANG ; Chun-Ni ZHANG ; Xiao-Chun LIAO ; Jin LI ; Bai-Ping MA
China Journal of Chinese Materia Medica 2019;44(12):2552-2558
This study aimed to comprehensively assess the difference of alkaloid components between old stems and tender stems of Gelsemium elegans by using ultra high-performance liquid chromatography coupled with photo-diode array and quadrupole time-of-flight mass spectrometry( UPLC-Q-TOF/MS~E) and high-performance liquid chromatography coupled with UV detector( HPLC-UV). Firstly,the different components in old stems and tender stems were analyzed by UHPLC-Q-TOF/MSEcombined with principal component analysis( PCA) and orthogonal partial least squares discriminant analysis( OPLS-DA),respectively. As a result,17 major different components were found. At the same time,the distribution of these alkaloids in old stems and tender stems was determined,and the alkaloids with higher polarity are relatively higher in the tender stems,while the old stems are in the opposite case. In addition,three main components in the G. elegans were quantified by HPLC-UV. The results showed that the contents of koumine and humantenmine in old stems were higher than those in tender stems,and the content of gelsemine in tender stems was relatively high. This study systematically evaluated the differences of alkaloids between the old stems and tender stems of G. elegans,and quantified the main three alkaloids. It laid the foundation of the safe and effective application of G. elegans.
Alkaloids
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analysis
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Chromatography, High Pressure Liquid
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Gelsemium
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chemistry
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Mass Spectrometry
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Plant Extracts
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Plant Stems
;
chemistry
10.Study on chemical constituents of stems and leaves of Sapium discolor.
Yong-Li ZHANG ; Qi-Ming PAN ; Gui-Jie ZHANG ; Dong LIANG
China Journal of Chinese Materia Medica 2019;44(17):3738-3744
Seventeen compounds were isolated from the 95% ethanol extract of the stems and leaves of Sapium discolor by using various chromatographic techniques,including silica gel,Sephadex LH-20,MCI,ODS,and semi-preparative HPLC. Their structures were elucidated as sapiumin F( 1),kadsulignan C( 2),ciwujiatone( 3),ethylbrevifolin carboxylate( 4),7-hydroxy-8-methoxycoumarin( 5),fraxetin( 6),fraxidin( 7),isofraxidin( 8),6,7,8-trimethoxycoumarin( 9),5,6,7,8-tetramethoxycoumarin( 10),8-hydroxy-5,6,7-trimethoxycoumarin( 11),3,3'-di-O-methylellagic acid( 12),3,3',4'-tri-O-methylellagic acid( 13),3'-methoxyellagic acid 4'-O-α-rhamnopyranoside( 14),4,5-didehydro-chebulic acid triethyl ester( 15),ent-kaurane-3-oxo-16α,17-diol( 16),and abscisic acid( 17) by spectroscopic data. Compound 1 is a new compound. Except for compounds 4,11,and 13,the remaining compounds were isolated from this plant for the first time. All the isolates were evaluated for their in vitro antineuroinflammatory activities,and the results showed that compounds 6 and 15 significantly inhibited nitric oxide production in lipopolysaccharide-induced BV-2 microglial cells,with IC50 values of 6. 06 and 6. 05 μmol·L-1,respectively.
Animals
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Cell Line
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Chromatography, High Pressure Liquid
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Mice
;
Phytochemicals
;
analysis
;
Plant Leaves
;
chemistry
;
Plant Stems
;
chemistry
;
Sapium
;
chemistry

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