60(P23) 日本産イチイ針葉部より得られる新規タキサンジテルペン類の効率的分離法の開発ならびに構造決定とカルス培養によるタキソール関連化合物の生産(ポスター発表の部)

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A simple method for the isolation of taxol and other taxane diterpens from the needles of Japanese yew, Taxus cuspidata sieb. et Zucc. was developed. The ethyl acetate extracts of the needles were washed with acid and base to remove basic and phenolic compounds. The separation of taxol and its analogs from the neutral extracts by the combination of silica gel fresh chromatography and HPLC was achieved easily and in good yields. The taxol (22) and cephalomannine (24) were obtained in 0.004 % and 0.003 % yields respectively based on fresh needles. 13 new taxane diterpen alkaloids (taxine NA-1-NA-11 (1-11), 2(3->20)abeotaxine NA-1 (12) and NA-2 (13)) and 8 new taxanes (taxinine NN-1, 2, 5, and NN-6 (14-17), 11(15->1)abeotaxinine NN-1 (18), 2(3->20)abeotaxinine NN-1 (19), NN-2 (20), 3,13-cyclotaxinine NN-1 (21)) were isolated from the crude alkaloid fraction by the combination of alumina column chromatography and reversed phase HPLC(ODS) eluted with a mixture of ammonium acetate buffer (pH4.7)-MeOH-MeCN. Taxol and its analogs were isolated from the callus culture of Taxus cuspidata, together with taxuynnanine C (31) and its analogs (32〜35) in high yields (0.49 %). The callus culture was developed with young stem tissue of the yew grown at Aobayama of Sendai in 1997 and maintained in Gamborg B5 medium containing 0.5mg/L NAA at 27℃ in darkness. After growth for 40-50 days, biomass was scraped from solid medium and freeze-dried. The dry callus calture was extracted with hexane, ethyl acetate, and MeOH successively. These extracts were separated by the combination of silica gel fresh chromatography and HPLC. Taxol (22), 7-epitaxol (23), and taxuyunnanineA (28) were isolated from the extracts of EtOAc and MeOH in 0.014%, 0.0015 %, and 0.009 % yields, respectively. Taxuynnanine C (31) and its analogs (32), (33), (34), and (35) were obtained from these extracts in 0.135 %, 0.014 %, 0.009 %, 0.275 %, and 0.053 % yields, respectively.
天然有機化合物討論会の論文
1998-08-31

60(P23) 日本産イチイ針葉部より得られる新規タキサンジテルペン類の効率的分離法の開発ならびに構造決定とカルス培養によるタキソール関連化合物の生産(ポスター発表の部)

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