Cholestane glycoside

A new cholestane glycoside (18) with a benzoyl-rhamnoglucosyl moiety isolated from Ornithogalum saundersiae strongly inhibited in vitro the growth of human promyelocytic leukemia HL-60 cells and human T-lymphocytes leukemia MOLT-4 cells with IC50 of 21 and 18 nM... 

Liliaceae is a rich source of steroidal glycosides. In the course of our continuous studies on chemical constituents of Liliaceae plants, a number of new steroidal glycosides including cholestane glycosides and steroidal alkaloids have been isolated. 

The cytostatic activities of the cholestane glycosides partly resulted from the induction of apoptosis. The apoptosis is caused by the activation of calcium dependent endonuclease. An analysis of flow cytometry pointed out that glycosides stopped the cell cycle of HL-60 at S2/M phase and induced apoptosis at GO/Gl phase . 

The cholestane glycoside (43),the main constituent of the bulbs of 0. saundersiae, showed a remarkably strong cytostatic activity which is about lO-lOOtimes stronger than those of mitomycin C(MMC), ADM, cisplatin(CDPP), camptpthecin(CPT) and taxol(TAX) (Table III). 

Cholestane glycosides furostanol open-chain steroidal glycosides spirostanol stereochemistry steroidal saponins structure elucidation... 

Kuroda M, Mimaki Y, Yokosuka A, Sashida Y (2001) Cholestane glycosides from the bulbs of Galtonia candicans and their eytotoxieity. Chem Pharm Bull 49 1042-1046... 

Yoshimitsu H, Nishida M, Nohara T (2000) Cholestane glycosides from Solatium abutiloides. ID. Chem Pharm Bull 48 556-558... 

Kubo S, Mimaki Y, Terao M, Sashida Y, Nikaido T, Ohmoto T (1992) Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae. Phytochemistry 31 3969-3973... 

Mimaki Y, Kuroda M, Kameyama A, Sashida Y, Hirano T, Oka K et al (1997) Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs. Bioorg Med Chem Lett 7 633-636... 

Tian R-H, Ohmura E, Yoshimitsu H, Nohara T, Matsui M (1996) Solanaceous plants. XXXIV. Cholestane glycosides from Solarium abutiloides. Chem Pharm Bull 44 1119-1121... 

Mimaki Y (2006) Structures and biological activities of plant glycosides cholestane glycosides from Ornithogalum saundersiae, O. thyrsoides and Galtonia candicans, and their cytotoxic and antitumor activities. Nat Prod Commun 1 247-253... 

Miscellaneous Rare Steroidal Metabolites 7.9.1 Homo-cholestane Glycosides (C j +... 

CoA) thus forming /tomo-cholestane glycosides (Fig. 7.25). The carbohydrate chain at C-3P of aethiosides A and C was determined to be P-chacotriosyl, well-known from steroidal glycoalkaloids. In the case of congener B the trioside contained xylose instead of rhamnose at C-4 of glucose. 

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