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

Three seco-prezizaane-type sesquiterpene lactones, one phenylpropanoid, and two lignans were isolated from the 95% ethanol extract of stems and branches of Illicium ternstroemioides with silica gel column chromatography, ODS column chromatography, and preparative HPLC. Based on the spectral data, they were identified as burmanicumolide D(1), veranisatin A(2), veranisatin B(3), dihydroconiferylalcohol(4), pinoresinol(5),(-)-matairesinol(6), respectively. Among them, compound 1 was a new seco-prezizaane-type sesquiterpene lactone, and 2-6 were obtained from this plant for the first time. None of these compounds display antiviral or cytotoxic activities.
Antiviral Agents ; Illicium ; Lactones ; Molecular Structure ; Phytochemicals ; Sesquiterpenes

Ten seco-prezizaane sesquiterpenes were isolated from the water-soluble fraction of the fruit of Illicium lanceolatum using the combined methods of silica gel column chromatography,Sephadex LH-20 column chromatography,and RP-preparative HPLC. They were elucidated as majusanol E( 1),2α-hydroxycycloparviflorolide( 2),2β-hydroxy-3,6-dedioxypseudoanisatin( 3),majusanol A( 4),merrillianone( 5),cycloparvifloralone( 6),3α-hydroxycycloparvifloralone( 7),1,2-dehydrocycloparvifloralone( 8),henrylactone C( 9),and( 11) 7,14-ortholactone-3α-hydroxyfloridanolide( 10) according to the NMR data. All compounds were obtained from this plant for the first time. Neuroprotection activity,anti-Coxsackie B3 virus,and anti-H3 N2 virus experiments were carried out to test their bioactivities. The bioassay results showed that compounds 1,4,6,7,9 and 10 displayed weak protective effects of the damage of nerve SH-SY5 Y cell induced by monosodium glutamate.
Fruit ; Illicium ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Neuroprotection ; Sesquiterpenes

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

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

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 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

BACKGROUND: Candida albicans is a member of the normal flora of the skin, mucous membrane and gastrointestinal tract. Vaginal candidiasis remains a significant problem in women in childbearing age, Majority of the cases are caused by C. albicans and recurrence is common in spite of topical treatment. OBJECTIVE: The purpose of this study is to develop the antifungal agent from the medicinal herbs traditionally used in Korea. METHOD: In this study, the extracts and essential oils from Foeniculum vulgare and Illicium verum were examined for antifungal activities against C. albicans. RESULT: Dichloromethane extracts and essential oils from Foeniculum vulgare and Illicium verum showed antifungal activity against C. albicans. One fraction from Illicium verum with antifungal activity was founf out as 1-methoxy-4-(2-prophenyl) benzene. CONCLUSION: Dichloromethane extract and 1-methoxy-4-(2-prophenyl) benzene with antifungal activity from Illicium verum could be the candidate for a new antifungal agent for candidiasis and other fungal diseases.
Benzene ; Candida ; Candida albicans ; Candidiasis ; Female ; Foeniculum ; Gastrointestinal Tract ; Humans ; Illicium ; Methylene Chloride ; Mucous Membrane ; Oils, Volatile ; Plants, Medicinal ; Recurrence ; Skin