Steroidal glycosides from the underground parts of Solanum sodomaeum

A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addition, their antiproliferative activity against human promyelocytic leukemia (HL-60) cells was investigated, and five compounds exhibited stronger activity than cisplatin.     

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.     

Three unusual 22-beta-O-23-hydroxy-(5 alpha)-spirostanol glycosides from the fruits of Solanum torvum

Three novel 22-beta-O-spirostanol oligoglycosides, torvosides J (1), K (2) and L (3) have been isolated from the fruits of Solanum torvum SWARTZ and their chemical structures have been characterized based on the spectroscopic means. They are worth of note as rare 22-beta-O-spirostanol glycosides.     

Steroidal glycosides from the roots of Asclepias curassavica

Twenty-six new acylated-oxypregnane glycosides were obtained along with three known cardenolide glycosides from the roots of Asclepias curassavica (Asclepiadaceae). The new compounds were confirmed to contain 12-O-benzoylsarcostin, 12-O-benzoyldeacylmetaplexigenin, kidjolanin, and 12-O-benzoyltayloron, and one new acylated-oxypregnane, 12-O-(E)-cinnamoyltayloron, as their aglycones, using both spectroscopic and chemical methods.     

Steroidal glycoalkaloids from the berries of Solanum distichum

Two steroidal glycoalkaloids, Solanidine 3-O-[alpha-L-rhamnopyranosyl-(1' --> 4)-[alpha-L-rhamnopyranosyl-(1' --> 2)]-beta-D-glucopyranoside] (1) and Solanidine 3-O-[alpha-L-rhamnopyranosyl-(1' --> 4)-beta-D-glucopyranoside] (2) commonly known as alpha-chanonine and beta 2-chanonine, were isolated from the berries of Solanum distichum. The structures of the isolated compounds were studied by 1D and 2D NMR techniques and FAB MS analysis. The 13C NMR signal assignments and direct elucidation of the glycoside linkages were established. Glycoalkaloids level in the dried berries, determined by a simple colorimetric method, was found to be 5.08 +/- 0.18 g%.     

Steroidal saponins from the fruits of Cestrum ruizteranianum

Seven spirostane and furostane-type glycosides were isolated from the aqueous methanolic extract of the fruits of Cestrum ruizteranianum and characterized mainly by 2D NMR spectroscopy and mass spectrometry. These known saponins belong to the delta5-spirostene and delta5-furostene series and are reported in this species for the first time.     

Studies on the constituents of Mikania hirsutissima (Compositae).

Two novel norhumulene-type sesquiterpenes, named mikaniahumulene I (1) and II (2) were isolated along with nine known compounds, seven kaurenic acid-type diterpenes (3-9), a coumarin (10) and a flavone (11), from the aerial parts of Mikania hirsutissima DC (Compositae). The structures of new norhumulenes were determined by spectroscopic means. The cytotoxic activities of isolated compounds against leukemia cells (L 1210) were investigated; among the isolated compounds, 1, 5, 8, and 11 showed relatively strong cytotoxicity.     

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。     

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.     

Steroidal glycosides from the aerial part of Asclepias incarnata L. II

Thirty new steroidal glycosides were obtained from the aerial part of Asclepias incarnata L. (Asclepiadaceae). These glycosides were confirmed to have lineolon, isolineolon, 12-O-acetyllineolon, 12-O-(Z)-cinnamoyllineolon, metaplexigenin, 15 beta-hydroxylineolon, 15 beta-hydroxyisolineolon, 16 alpha-hydroxyisolineolon, 12-O-tigloyl-16 alpha-hydroxyisolineolon as the aglycone and 2,6-dideoxyhexopyranose as the sugar sequence by spectroscopic methods and chemical evidence.     

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').     

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.     

Steroidal glycosides from the bulbs of Camassia leichtlinii and their cytotoxic activities.

Phytochemical analysis of the bulbs of Camassia leichtlinii (Liliaceae) resulted in the isolation of six new spirostanol saponins, a new furostanol saponin, a cholestane glucoside, and four known steroidal saponins. The structures of the new saponins were determined by detailed analysis of their spectral data, including two-dimensional NMR spectroscopy, and by the results of hydrolytic cleavage. Cytotoxic activities of the isolated compounds against human oral squamous cell carcinoma (HSC-2) cells and normal human gingival fibroblasts (HGF) are also reported.     

Steroidal and triterpenoidal saponins from the fruits of Diploclisia glaucescens

Chemical investigation of methanol extract of the fruits of Diploclisia glaucescens furnished 3-O-beta-D-glucopyranosyl-20-hydroxyecdysone, 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]serjanic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[beta-xylopyranosyl(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]serjanic acid 28-O-beta-D-glucopyranosyl ester. The latter saponin was found to be a new natural product while the other two are reported for the first time from the family Menispermaceae.