Studies on the constituents of solanaceous plants. (46). Steroidal glycosides from the fruits of Solanum anguivi

Three new glycosides named anguiviosides A-C were isolated from the fruits of Solanum anguivi and characterized as follows:3-O-beta-chacotrioside (1), 3-O-[4-O-maloyl-alpha-L-rhamnopyranosyl(1-->2)]-alpha-L-rhamnopyra nosyl(1-->4)-beta-D-glucopyranoside (2) and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl(1-->3)]-beta-D-+ ++glucopyranoide (3), of (25R,26R)-spirost-5-en-3beta,26-diol.     

Antiproliferative constituents from umbelliferae plants. IX. New triterpenoid glycosides from the fruits of Bupleurum rotundifolium

The MeOH extract of the fruits of Bupleurum rotundifolium showed inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. Bioactivity-guided fractionation of the MeOH extract led to the isolation of four new triglycosides of 13beta,28-epoxy oleanane-type triterpenes, named rotundiosides O, Q, S and T; 12 new glycosides of oleanane-type triterpenes, named rotundiosides J-N, P, R, U-Y, and others; echinocystic acid 3-O-sulfate; and three known oleanane-type triterpene glycosides, rotundiosides A, F and G. The structures of the new isolates were determined based on chemical and spectroscopic evidence. The GI(50) of isolates against MK-1, HeLa and B16F10 cell lines are reported.     

Antiproliferative constituents from Umbelliferae plants VI. New ursane-type saikosaponin analogs from the fruits of Bupleurum rotundifolium

The MeOH extract of the fruits of Bupleurum rotundifolium showed inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth (GI(50): 6.25 microg/ml). From this extract, 10 new ursane-type triterpene glycosides viz. three 3-O-triosides (called rotundifoliosides A, I, and J) of 13beta,28-epoxy-3beta,16alpha-dihydroxyurs-11-ene, two (G and H) of 13beta,28-epoxy-3beta,16alpha,23-trihydroxyurs-11-ene, two (E and F) of 13beta,28-epoxy-3beta,16alpha,21beta-trihydroxyurs-11-ene, two (B and C) of 3beta,11alpha,16alpha,28-tetrahydroxyurs-12-ene, and one (D) of 3beta,11alpha,28-trihydroxy-15alpha,16alpha-epoxyurs-12-ene were isolated in addition to 16 new oleanane-type triterpene glycosides (rotundiosides J-Y), echinocystic acid 3-O-sulfate and 3 known oleanane-type triterpene glycosides (rotundiosides A, F and G). The isolation, structures and antiproliferative activity of the new ursane-type triterpene glycosides against MK-1, human uterus carcinoma (HeLa), and murine melanoma (B16F10) cell lines are described with some comments on the structural requirements for their activity.     

Studies on the constituents of Catalpa species. VI. Monoterpene glycosides from the fallen leaves of Catalpa ovata G. Don.

Five new monoterpene glycosides, ovatolactone 7-O-(6'-O-p-hydroxybenzoyl)-beta-D-glucopyranoside, ovatic acid methyl ester 7-O-(6'-O-p-hydroxybenzoyl)-beta-D-glucopyranoside, 7-O-p-hydroxybenzoylovatol 1-O-(6'-O-p-hydroxybenzoyl)-beta-D-glucopyranoside, 6'-O-p-hydroxybenzoylcatalposide and (2E,6R)-2,6-dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside were isolated from the fallen leaves of Catalpa ovata G. Don. Their structures were determined by extensive spectroscopic studies and syntheses.     

Bioactive constituents from chinese natural medicines. XXIX. Monoterpene and monoterpene glycosides from the roots of Rhodiola sachalinensis

A new monoterpene, sachalol, and three new monoterpene glycosides, sachalosides VI, VII, VIII, were isolated from Rhodiolae Radix, the roots of Rhodiola sachalinensis. The absolute stereostructures of new monoterpenes were elucidated on the basis of chemical and physicochemical evidence including the application of the modified Mosher's method.     

中国番荔枝科植物抗癌有效成分研究

介绍了近年来我们实验室中国番荔枝科植物抗癌有效成分研究工作。从番荔枝科5种紫玉盘属植物,5种哥纳香属植物,1种番荔枝属植物,1种囊瓣木属植物中分离得到59种新的番荔枝内酯,32种新的多氧取代环己烯,12种新的苯乙烯吡喃酮和3种新的生物碱,并通过化学和光谱方法鉴定了它们的结构。大部分化合物显示了较强的抗癌活性。并对抗癌活性成分海南哥纳香醇甲进行了全合成。     

Studies on lignan constituents from Schisandra chinensis (Turcz.) Baill. fruits using high-performance liquid chromatography/electrospray ionization multiple-stage tandem mass spectrometry

A reversed-phase high-performance liquid chromatography-diode array detector-electrospray ionization multiple-stage tandem mass spectrometry (RP-HPLC-DAD-ESI-MS(n)) method has been developed for the detection and analysis of lignan constituents in the methanol extract from the fruits of Schisandra chinensis (Turcz.) Baill. RP-HPLC-DAD-ESI-MS(n) and electrospray ionization Fourier transform ion cyclotron resonance multiple-stage tandem mass spectrometry (ESI-FT-ICR-MS(n)) have been applied to investigate the characteristic product ions of four lignan reference compounds. Then, the logical fragmentation pathways of the lignans have been proposed. By comparing the retention time (t(R)) of HPLC, the ESI-MS(n) data and the structures of analyzed compounds with the data of reference compounds and in the literature, 11 peaks in HPLC have been unambiguously identified and another 5 peaks have been tentatively identified or deduced. Also, in the present paper, the extracted ion chromatograms (EIC) have been used to analyze the lignan isomers. The experimental results demonstrate that RP-HPLC-DAD-ESI-MS(n) is a specific and useful method for the identification of the lignan constituents and their isomers.     

Studies on the chemical constituents of the fruits of Cordia latifolia

Four new aromatic compounds have been isolated from the fruits of Cordia latifolia (Boreginaceae) bearing a common basic skeleton but differing in the side chain. Their structures were elucidated using spectrometric methods including 1D- (1H and 13C) and 2D-NMR experiments, (1H, 1H-COSY, NOESY, HMQC and HMBC) and chemical transformations.     

番红花化学成分研究 III. 番红花花粉中的番红花新苷甲和乙的结构

从番红花(crocus sativus L.)花粉中分到两个新苷, 命名为番红花新苷甲(1)和乙(2)。经理化性质和对它们的IR、UV、^1HNMR和MS数据的分析, 鉴定1为异鼠李素-4'-O-α-L-鼠李吡喃(1→2)β-D-葡萄吡喃糖苷, 2为β-对羟基苯基-乙醇-α-O-α-L-鼠李吡喃糖(1→2)-β-D-葡萄吡喃糖苷。     

Studies on the constituents of Swertia japonica Makino II. On the structures of new glycosides

Two new secoiridoid glycosides, swertiajaposide A (1) and swertiajaposide B (2), a new unsaturated alco-hol glycoside, 3-butenyl 6'-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (3), and a new lignan glycoside, 7R,7'R,8S,8'S-(+)-neo-olivil-4-O-beta-D-glucopyranoside (4), were isolated together with six known compounds from the whole plants of Swertia japonica Makino. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.     

Studies on the constituents of Cimicifuga species. XXVIII. Cycloart-7-enol glycosides from the underground parts of Cimicifuga simplex Wormsk

Four new cycloart-7-ene triterpenol arabinosides, bugbanosides C-F, were isolated from the underground parts of Cimicifuga simplex Wormsk. (Ranunculaceae). The structures were elucidated as 12beta-acetoxy-3beta,15alpha,-24R,25-tetrahydroxy-16,23-dione-cycloart-7-ene 3-O-alpha-arabinopyranoside, 12beta-acetoxy-24R,25-epoxy-3beta,15alpha-dihydroxy-16,23-dione-cycloart-7-ene 3-O-alpha-L-arabinopyranoside, 12beta-acetoxy-24R,25-epoxy-3beta-hydroxy-16,23-dione-cycloart-7-ene 3-O-alpha-L-arabinopyranoside, and 16,23R:16,24S-diepoxy-3beta,12beta,15alpha,25-tetrahydroxy-cycloart-7-ene 3-O-alpha-L-arabinopyranoside on the basis of spectral and chemical evidence. The circular dichroism (CD) of bugbanosides C-F showed strong negative maxima at 214-217 nm due to a cycloart-7-ene system, as well as other cycloart-7-ene triterpenes. The CD data showed to be useful in determining basic skeletons, including absolute stereostructures of cycloart-7-ene triterpenes.     

Studies on the constituents of Gardenia species. III. New iridoid glycosides from the leaves of Gardenia jasminoides cv. fortuneana Hara

Two new iridoid glycosides, 7 beta,8 beta-epoxy-8 alpha-dihydrogeniposide (1) and 8-epiapodantheroside (2), were isolated, together with six known (3-8) and three artifact (9-11) iridoids, from the leaves of Gardenia jasminoides cv. fortuneana Hara. Their structures were established based on chemical and spectral data.     

Studies on the constituents of Syringa species. XII. New glycosides from the leaves of Syringa reticulata (BLUME) HARA

Three new glycosides, 6'-O-alpha-D-galactopyranosylsyringopicroside (1), secologanoside 7-methyl ester (2) and (+)-lariciresinol 4'-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside (3), were isolated from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compound 1 is the first naturally occurring iridoid di-glycoside having melibiose. Comparison of the spectral data of 2 and that previously recognized as secologanoside 7-methyl ester led to the conclusion that the recognized structure should be revised to the sodium salt of secoxyloganin (2').