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

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

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

AIM: To study the chemical constituents of the fruits of Illicium henryi. METHOD: Chromatographic separations on silica gel, Sephadex LH-20 gel and MCI gel were used to isolate the compounds. The structures were elucidated based on extensive spectroscopic data analyses. RESULTS: Seven compounds were obtained and their structures were identified as 10-benzoyl-cycloparvifloralone (1), cycloparvifloralone (2), 2α-hydroxycycloparviforalone (3), henrylactone B (4), merrillianone (5), henrylactone C (6) and 7, 14-ortholactone- 3-hydroxyfloridanolide (7). CONCLUSION Compound 1 is a new sesquiterpene lactone. The tested compounds showed weak anti-HBV activities on HBV surface antigen (HBsAg) secretion and HBV e antigen (HBeAg) secretion using Hep G2.2.15 cell line.
Antiviral Agents ; chemistry ; isolation & purification ; pharmacology ; Fruit ; chemistry ; Hep G2 Cells ; Hepatitis B virus ; drug effects ; Humans ; Illicium ; chemistry ; Molecular Structure ; Plant Extracts ; chemistry ; pharmacology ; Sesquiterpenes ; chemistry ; isolation & purification ; pharmacology

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

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.

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