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

Ten compounds, including seven sesquiterpenes, two phenols and one phenylpropanoid, were isolated from the roots of Illicium majus by means of silica gel, ODS, Sephadex LH-20, and preparative HPLC. On analysis of MS and NMR spectroscopic data , their structures were established as cycloparviflorolide (1), cycloparvifloralone (2), tashironin (3), tashironin A (4), anislactone A(5), anislactone B (6), pseudomajucin (7), syringaldehyde (8), methyl-4-hydroxy-3, 5-dimethoxybenzoate (9), and (E)-3-methoxy-4,5-methylenedioxycinnamic alchol (10), respectively. Compounds 1-4 and 8-10 were first isolated from this plant. In the in vitro assays, at a concentration of 1.0 x 10(-5) mol x L(-1), compounds 5 and 6 were active against LPS induced NO production in microglia with a inhibition rate of 75.31% and 53.7%, respectively.
Drugs, Chinese Herbal ; analysis ; chemistry ; Illicium ; chemistry ; Organic Chemicals ; analysis ; chemistry ; Plant Roots ; chemistry

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

To study the chemical constituents of the methanol portion of the stem of Illicium henryi. The methanol portion was isolated and purified by HP-20, ODS, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were elucidated by MS and spectral data(1H, 13C-NMR). Five compounds were isolated from the methanol portion and identified as benzyloxy-1-O-beta-D-glucopyranoside (1), 4-hydroxy-phenethyl alcohol-O-beta-D-glucopyranoside (2), 3-methoxyl-4-hydroxyl-phenpropanol-O-beta-D-glucopyranoside (3), 3-methoxyl-4-O-beta-D-glucopyranosyloxy-benzoic acid methyl ester (4), and 4-O-beta-D-glucopyranosyloxy-benzoic acid methyl ester (5). All compounds were isolated from this plant for the first time.
Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Illicium ; chemistry ; Molecular Structure ; Spectrometry, Mass, Electrospray Ionization

Chemical constituents of ethyl acetate extract of Illicium burmanicum were isolated and purified by various chromatographic methods,including Silica gel, Sephadex LH-20, C18 reverse-phased silica gel, Preparative TLC and Preparative HPLC. Their structures were identified by spectral analysis including NMR and MS data. Fourteen compounds were separated from I. burmanicum and their structures were identified as 7S,8R-erythro-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (1), 7R,8R-threo-4,7, 9,9'-tetrahydroxy-3,3 '-dimethoxy-8-O-4'-neolignan(2) ,polystachyol(3), (-) -massoniresinol(4), angustanoic acid F (5), trans-sobrerol(6), (3S,6R) -6,7-dihydroxy-6,7-dihydrolinalool (7), (3S, 6S) -6,7-dihydroxy-6,7-dihydrolinalool (8), 2,6-dimethoxy-4-allyl-phenol (9), 3,5-dihydroxy4-hydroxy benzaldehyde (10), 3-hydroxy4-methoxybenzaldehyde (11), methyl vanillate (12), shikimic acid ethylester (13) and beta-sitosrerol (14). Except compound 14, the rest thirteen compounds were separated from this plant for the first time.
Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Illicium ; chemistry ; Molecular Structure ; Spectrometry, Mass, Electrospray Ionization

Fourteen new geranyl phenyl ethers (1-14) along with three known compounds (15-17) were isolated from Illicium micranthum, and their structures were elucidated by comprehensive spectroscopic methods. Illimicranins A-H (1-8) were characterized as geranyl vanillin ethers, while 9 and 10 were dimethyl acetal derivatives. Illimicranins I and J (11 and 12) were rare geranyl isoeugenol ethers. Illimicranins K and L (13 and 14) represented the first example of geranyl guaiacylacetone ether and geranyl zingerone ether, respectively. Compounds 1, 2 and 15 exhibited anti-HBV (hepatitis B virus) activity against HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis B e antigen) secretion, and HBV DNA replication.
Antiviral Agents/pharmacology* ; Hepatitis B Surface Antigens ; Hepatitis B e Antigens ; Illicium/chemistry* ; Phenyl Ethers

OBJECTIVETo study the chemical constituents from the active fractions against HIV in vitro, a crude ethanolic extract of Illicium simonsii.

METHODThe compounds were isolated with column chromatography methods. MS and NMR spectroscopic methods were used to determine the structures of the compounds.

RESULTSeven compounds were isolated from the active fractions against HIV in vitro of the 90% ethanol extract and their structures were elucidated as (+)-catechin (1), (-)-epicatechin (2), (+)-catechin 3-O-alpha-L-rhamnopyranoside (3), kaempferol 3-O-alpha-L-rhamnopyranoside (4), quercetin 3-O-alpha-L-rhamnopyranoside (5), erigeside C (6) and daucosterol (7).

CONCLUSIONSeven compounds were isolated from this plant for the first time, but none of them exhibited active against HIV in vitro. Compounds 3 and 6 were isolated from this genus for the first time.

Catechin ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Ethanol ; chemistry ; Glycosides ; chemistry ; Illicium ; chemistry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Rhamnose ; analogs & derivatives ; chemistry ; Sitosterols ; chemistry

OBJECTIVETo investigate the chemical characteristics of pericarps from Illicium species for developing a taxonomic and identification method for Illicium species.

METHODTwenty two samples from 17 Illicium species were detected with HPLC-MS. The chromatographic data were analyzed by cluster analysis using SAS software.

RESULTAccording to the similarity of chemical constituents of 22 samples. Illicium can be divided into five chemical sections. At the same time, the distribution of pseudoanisatin, 6-deoxypseudoanisatin, pseudomajucin was evaluated in 22 samples.

CONCLUSIONThe chemical constituents of pericarp of Illicium species can be characterized well by LC-MS chromatograms. LC-MS chromatograms can be used to identify the Chinese star anise. The results provided a certain basis to classify the Illicium species.

Chromatography, High Pressure Liquid ; methods ; Fruit ; chemistry ; Illicium ; chemistry ; classification ; Mass Spectrometry ; methods ; Plant Extracts ; analysis ; standards ; Quality Control

AIM: To study the constituents and bioactivity of Illicium simonsii. METHODS: The extracts of the fruits of Illicium simonsii were submitted to a combination of chromatographic materials, silica gel, ODS column chromatography and finally preparative HPLC to obtain eight compounds which were further evaluated for their cytotoxicity by MTT method. RESULTS: A new phenylpropanoid glycolside, 2, 4-dihydroxy-allylbenzene-2-O-β-D-glucopyranoside (1), together with seven characteristic sesquiterpene lactones, oligandrumin B (2), oligandrumin D (3), anisatin (4), veranisatin D (5), pseudomajucin (6), 1α-hydroxy-3-deoxy-pseudoanisatin (7), 8α-hydroxy-10-deoxycyclomerrillianolide (8) were isolated. CONCLUSION Compound 1 is new. Compounds 1, 2, 3, 5-8 were isolated from this plant for the first time. None of the isolates showed inhibitory effects on the growth of non-small cell lung tumor cell line A549.
Carcinoma, Non-Small-Cell Lung ; drug therapy ; Fruit ; chemistry ; Humans ; Illicium ; chemistry ; Lactones ; isolation & purification ; Monosaccharides ; isolation & purification ; Plant Extracts ; chemistry ; Sesquiterpenes ; isolation & purification

Silica gel column chromatography was used for the isolation and purification of the chemical constituents of the pericarp of Illicium macranthum. From dichloromethane-EtOAc (1:1) fraction and EtOAc fraction of the methanol extracts, eleven compounds were identified on the basis of chemical and spectral data. Two new compounds were elucidated to be 6-deoxyneomajucin (1) and 2-oxo-6-deoxyneomajucin (2), along with nine known compounds 6-deoxypseudoanisatin (3), pseudoanisatin (4), anisatin (5), pseudomajucin (6), protocatecheuic acid (7), shikimic acid (8), shikimic acid methylester (9), beta-sitosterol (10) and daucosterol (11). Compounds 1 and 2 are new majucin-type sesquiterpene lactones.
Drugs, Chinese Herbal ; chemistry ; Fruit ; chemistry ; Illicium ; chemistry ; Lactones ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Plants, Medicinal ; chemistry ; Sesquiterpenes ; chemistry ; isolation & purification ; Shikimic Acid ; chemistry ; isolation & purification ; Sitosterols ; chemistry ; isolation & purification ; Spiro Compounds ; chemistry ; isolation & purification