89(P26) Galtonia candicansより単離されたコレスタン配糖体の構造とそれらの培養腫瘍細胞に対する増殖抑制活性(ポスター発表の部)

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Galtonia candicans (Liliaceae) is a perennial plant which is native to the Cape Province of South Africa. We have found that the MeOH extract of Galtonia candicans bulbs exhibited extremely potent cytostatic activity toward human promyelocytic leukemia HL-60 cells with an IC_<50> value of 17ng/ml. On fractionation of the MeOH extract into n-BuOH-solbule phase and H_2O phase, the cytostatic activity appeared only in the n-BuOH phase (5.6ng/ml). Chromatographic separation of the n-BuOH phase led to the isolation of fifteen cholestane glycosides (1-15). The structures of 1 and 2 were determined by 2D NMR techniques, ^1H-^1H COSY, phase-sensitive NOESY, HMQC, and HMBC spectra, and acid- and alkaline catalyzed hydrolysis. Compound 1 was a new polyhydroxylated 16,23-epoxy-5β-cholestane diglycoside. Compound 2 was a novel 24 (23→22)abeo-cholestane diglycoside with two acetal rings between C-16 and C-23, and between C-18 and C-23. The structures of the other isolated compounds (3-15) were elucidated on detailed analysis of their ^1H- and ^<13>C-NMR spectra, partly 2D NMR spectra, hydrolysis, and by comparison with spectral data of known compounds. These compounds were new naturally occurring constituents, except for 5 and 15. The isolated compounds and some derivatives were evaluated for cytostatic activity on leukemia HL-60 cells. Cytostatic activities of 1,2, and 10-13 were as potent as, or much more potent than those of the clinically applied anticancer agents, etoposide, methotrexate, and adriamycin. Subsequent evaluation of 1 and 2 in the Jpn. Fdn. for Cancer Res. 38 cell line assay showed that the mean concentration required to achieve GI_<50>, TGI, and LC_<50> levels against the panel of cells tested were 1.48, 21.9, and 70.8μM (1), and 0.72, 6.46, and 28.2μM (2), respectively. Each compound exhibited significant differential cellular sensitivity. Three cell lines were especially sensitive to central nervous cancer SF-295 (1: GI_<50> 0.031μM; TGI 0.102μM; LC_<50>4.09μM, 2: GI_<50>0.039μM; TGI 0.123μM; LC_<50> 4.19μM), SF-539 (1: GI_<50> 0.042μM; TGI 0.39OμM; LC_<50> 7.44μM, 2: GI_<50> 0.051μM; TGI 0.429μM; LC_<50> 6.50μM), small cell lung cancer DMS273 (1: GI_<50> 0.030μM; TGI 0.105μM; LC_<50> 0.577μM, 2: GI_<50> 0.027μM; TGI 0.071μM; LC_<50>0.325μM) cell lines. These compounds could be expected to be possible seeds for new anticancer agents from a higher plant next to camptothecin and taxol.
天然有機化合物討論会の論文
1999-09-01

89(P26) Galtonia candicansより単離されたコレスタン配糖体の構造とそれらの培養腫瘍細胞に対する増殖抑制活性(ポスター発表の部)

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