1.Investigation on flavonoids from fruits of Illicium oligandrum
Wenzhao TANG ; Dongmin SU ; Shishan YU ; Jing LIU ; Jing QU ; Yunbao LIU
Chinese Traditional and Herbal Drugs 1994;0(10):-
Objective To isolate and identify the flavonoids from the fruits of Illicium oligandrum.Methods The flavonoids were isolated by silica-gel,Sephadex LH-20,and ODS column chromato-graphies.Their structures were elucidated by 1H-NMR,13CNMR,and ESI-MS.Results Eleven flavonoids were isolated and identified as kaempferol(Ⅰ),quercetin(Ⅱ),quercetin-3-O-?-D-galactopyranoside(Ⅲ),isorhamnetin-3-O-?-D-glucopyranoside(Ⅳ),quercetin-3-O-?-L-arabinopy-ranoside(Ⅴ),quercetin-3O-?-L-rhamnopyranoside(Ⅵ),dihydroquercetin-3O-?-L-rhamnopyranoside(Ⅶ),dihydrokaempferol-3O-?-L-rhamnopyranoside(Ⅷ),quercetin-3O-?-D-(6″-O-?-L-rhamnopy-ranosyl) glucopyranoside(Ⅸ),kaempferol-3-O-?-D-(6″-O-?-L-rhamnopyranosyl) glucopyranoside(Ⅹ),isorhamnetin-3-O-?D-(6″-O-?-L-rhamnopyranosyl) glucopyranoside(Ⅺ).Conclusion All these compounds are firstly obtained from the plants of fruits of I.oligandrum and compounds Ⅳ,Ⅴ,Ⅶ,Ⅷ,and Ⅺ are isolated from the plants of Illicium L.for the first time.
2.Rapamycin inhibits growth and metastasis of gallbladder cancer GBC-SD cells
Zhaolong LIU ; Bo YAN ; Yunbao LUO ; Yongbing WANG ; Ceran HAN ; An SONG ; Shiyong YU ; Kun HOU
Chinese Journal of Cancer Biotherapy 2009;16(6):600-603
Objective:To investigate the effect of rapamycin on cell growth and migration of gallbladder cancer GBC-SD cells, and to discuss its potential in clinical therapy of gallbladder cancer. Methods: Proliferation of GBC-SD cells treated with different concentrations of rapamycin (12.5, 25, and 50 mmol/L) was examined by MTT assay. Cell cycle distribu-tion and apoptosis of GBC-SD cells treated with different concentrations of rapamycin were determined by flow cytometry. Migration ability of GBC-SD cells was assessed by Transwell assay. The expression of mTOR (mammalian target of rapam-ycin) and its phosphorylation in GBC-SD cells were examined by Western blotting assay. Results: Rapamycin significant-ly inhibited the phosphorylation of roTOR, but had no influence on the expression of roTOR in GBC-SD cells. Rapamycin significantly inhibited the growth of GBC-SD cells in a dose-dependent manner (P < 0.01). Raparnycin induced apoptosis of GBC-SD cells and arrested them at the G_1/S phase. Furthermore, rapamycin also significantly suppressed migration of GBC-SD cells as showed by Transwell assay (P < 0.01). Conclusion: Rapamycin can remarkably inhibit the growth and migration of gallbladder cancer cells, probably by inhibition of p-roTOR pathway, induction of apoptosis and cell cycle ar-rest of gallbladder cancer cells.
3.Chemical constituents from air-dried Piper longum.
Wenfeng LIU ; Zhiyong JIANG ; Jijun CHEN ; Xuemei ZHANG ; Yunbao MA
China Journal of Chinese Materia Medica 2009;34(9):1101-1103
OBJECTIVETo study the chemical constituents of Piper longum.
METHODThe whole plant of air-dried P. longum. was extracted with 95% EtOH. The EtOH extract was suspended in H2O and extracted with petroleum ether, CHC13 and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the CHCl3 fraction, and identified based on spectral analyses (MS,1H-NMR, 13C-NMR).
RESULTThreeteen compounds were isolated from P. longum, and were characterized as 1-(3',4'-methylenedioxyphenyl)-1E-tetradecene (1), 3-(3', 4'-methylenedioxophenyl)-propenal (2), piperoic acid (3), 3',4'-di-hydroxy-biabola-1,10-diene (4), eudesm-4(15)-ene-1beta, 6alpha-diol (5), 7-epi- eudesm-4( 15)-ene-1beta, 6beta-diol (6), guineesine (7), piperine (8), pipericide (9), 2E, 4E-dienamide (10), (2E, 4E, 8E) -N-isobutylhenicosa-2,4,8-trienamide (11), piperlonguminine (12), methyl piperate (13),
CONCLUSIONCompounds 1-6 were obtained from P. longum for the first time.
Air ; Desiccation ; Organic Chemicals ; analysis ; isolation & purification ; Piper ; chemistry
4.Chemical constituents from rhizomes of Illicium henryi.
Jifeng LIU ; Xuemei ZHANG ; Yao SHI ; Zhiyong JIANG ; Yunbao MA ; Jijun CHEN
China Journal of Chinese Materia Medica 2010;35(17):2281-2284
OBJECTIVETo study the chemical constituents of Illicium henryi.
METHODColumn chromatographic techniques using silica gel, Sephadex LH-20, Rp-8 and Rp-18 as packing materials were applied to isolate constituents. The structures of isolates were determined on the basis of spectroscopic data analyses.
RESULTTwelve compounds were isolated from the rhizomes of I. henryi, which were characterized as balanophonin (1), aviculin (2), rubriflosides A (3), 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (4), jasopyran (5), kaempferol (6), quercetin (7), (2R, 3R)-3, 5, 7, 3', 5'- pentahydroxyflavan (8), 3, 4, 5-trimethoxyphenyl-1-O-beta-D-glucopyranoside (9), 3, 4-dimethoxyphenyl-1-O-beta-D-glucopyranoside (10), coniferyl aldehyde (11), sinapaldehyde (12), respectively.
CONCLUSIONAll the isolates were obtained for the first time from this plant.
Illicium ; chemistry ; Plant Extracts ; analysis ; isolation & purification ; Rhizome ; chemistry
5.Chemical constituents from Piper longum.
Wenfeng LIU ; Zhiyong JIANG ; Jijun CHEN ; Xuemei ZHANG ; Yunbao MA
China Journal of Chinese Materia Medica 2009;34(22):2891-2894
OBJECTIVETo study the chemical constituents of Piper longum.
METHODThe whole plant of air-dried P. longum was extracted with 95% EtOH. The EtOH extract was suspended in H2O and extracted with petroleum ether, CHCl3 and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the CHCl3 fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR).
RESULTEleven compounds were isolated from P. longum, and were characterized as coumaperine (1), N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine (2), piperolactam A (3), 1-[1-oxo-5 (3,4-methylenedioxyphenyl) -2E,4E-pentadienyl] -pirrolidine (4), 1-[1-oxo-5 (3,4-methylenedioxyphenyl) -2E-pentenyl] -pirrolidine (5), 1-[1-oxo-9 (3,4-methylene dioxyphenyl)-2E, 8E-nonadienyl] -pyrrolidine (6), (R)-(-) -turmerone (7), octahydro-4-hydroy-3alpha-methyl-7-methylene-alpha-(1-methylethyl)-1H-indene-1-methanol (8), (+) -aphanamol I (9), bisdemethoxycurcumin (10), demethoxycurcumin (11).
CONCLUSIONCompounds 1-11 were obtained from P. longum for the first time.
Drugs, Chinese Herbal ; chemistry ; Magnetic Resonance Spectroscopy ; Piper ; chemistry
6.Studies on chemical constituents of Illicium simonsii.
Jifeng LIU ; Xuemei ZHANG ; Yao SHI ; Quan ZHANG ; Yunbao MA ; Jijun CHEN
China Journal of Chinese Materia Medica 2011;36(10):1311-1315
OBJECTIVETo study the chemical constituents of the Illicium simonsii.
METHODThe stems and leaves of I. simonsii were extracted with 95% EtOH. The EtOH extract was dispersed in H2O and extracted with petroleum, CHCl3 and BuOH, successively. The CHCl3 and BuOH fractions were isolated and purified by column chromatography on silica gel, Sephadex LH-20, Rp-C8 and Rp-C18. The isolated compounds were identified on the basis of spectral analyses (including MS, 1H-NMR, 13C-NMR).
RESULTFourteen compounds were isolated from the stems and leaves of I. simonsii, which were characterized as ficusesquilignan A (1), buddlenol C (2), buddlenol D (3), leptolepisol A (4), acernikol (5), aviculin (6), kaempferol (7), quercetin (8), quercetin 3-O-alpha-L-rhamnopyranosyl-(1 --> 6) -beta-D-glucopyranoside (9), taxifolin-3-O-beta-D-xylopyranoside (10), benzyl-2-O-beta-D-glucopyranosyl-2,6-dihydroxybenzoate (11), 2,4-dihydroxy-3,6-dimethyl-methylbenzoate (12), biondinin C (13), shikimic acid (14).
CONCLUSIONExcept compounds 9 and 14, all the other compounds were obtained from I. simonsii for the first time.
Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Illicium ; chemistry ; Plant Leaves ; chemistry
7.Chemical constituents of Neoalsomitra integrifoliola.
Dongmin SU ; Wenzhao TANG ; Shishan YU ; Yunbao LIU ; Jing QU ; Dequan YU
China Journal of Chinese Materia Medica 2012;37(11):1593-1596
OBJECTIVETo study the chemical constituents of the n-BuOH fraction of 95% ethanolic extract of leaves of Neoalsomitra integrifoliola.
METHODThe compounds were isolated with kinds of column chromatography. The structures were determined by MS and NMR spectroscopic techniques.
RESULTEight compounds were isolated from the n-BuOH fraction of 95% ethanolic extract and their structures were identified as 2-phenylethyl rutinoside (1), rutin (2), kaempferol-3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (3), isorhamnetin-3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (4), methyl chlorogenate (5), guanosine (6), adenosine (7), myo-inositol (8), respectively.
CONCLUSIONAll compounds were isolated from this genus for the first time.
Cucurbitaceae ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Organic Chemicals ; analysis ; chemistry ; isolation & purification
8.Antinociceptive grayanane-derived diterpenoids from flowers of .
Yong LI ; Yuxun ZHU ; Zhaoxin ZHANG ; Li LI ; Yunbao LIU ; Jing QU ; Shuanggang MA ; Shishan YU
Acta Pharmaceutica Sinica B 2020;10(6):1073-1082
Twelve new grayanoids (-) along with five known compounds were isolated from flowers of . Their structures were fully characterized using a combination of spectroscopic analyses, computational calculations, and single crystal X-ray diffraction. Rhomollone A () possesses an unprecedented 5/6/6/5 tetra-cyclic ring system (B- grayanane) incorporating a cyclopentene-1,3-dione scaffold. Rhodomollein XLIII () is a dimeric grayanoid, containing a novel 14-membered heterocyclic ring with a symmetry axis. The antinociceptive activities of compounds , , , , and - were evaluated by an acetic acid-induced writhing test. Among them, compounds , , , and displayed significant antinociceptive activities at a dose of 20 mg/kg with inhibition rates ranging from 41.9% to 91.6%. Compounds and inhibited 46.0% and 39.4% of the acetic acid-induced writhes at a dose of 2 mg/kg, while compound inhibited 34.3% of the writhes at a dose of 0.4 mg/kg.