59(P21) 中国産イチイTaxus maireiに含まれるタキサンジテルペノイド類(ポスター発表の部)

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Taxol^[○!R], as one of the most important anti-cancer drugs currently on the market for ovarian and breast cancer, has generated world wide interest in various areas, and extensive chemical studies have been carried out. In China, there distributed 5 kinds of yew tree: Taxus chinensis Rehd, T. yunnanesis Cheng et L. K. Fu, T. cuspidata Sieb et Zucc, T. wallichiana Zucc, T. mairei Cheng et L. K. Fu, all of them have been extensively studied in recent 15 years. T. mairei is an evergreen tall tree and mainly distributed in Jiangxi, Fujian and Taiwan Provinces, southeast of China. Previous studies have resulted in the isolation of more than 20 new taxanes from this plant, most of them have the normal taxane skeletons with 6/8/6 membered ring system. In search of new precursors fit for semisynthesis of taxol analogous, we re-examined the needles and the bark of this plant growing in a different area from those examined by other groups. Methanol extraction of the needles and bark of Taxus mairei, after treated with activated charcoal and concentration, was subjected to normal phase column chromatography, each fractions were repeatedly chromatographed on silica gel column and preparative TLC, finally afforded fourteen novel compounds, their structure were characterized belong to 11(15→1)abeotaxane, 2(3→20)abeotaxane, bicyclic taxoid diterpenes, respectively, on the basis of 1D and 2D NMR spectra including ^1H, ^<13>C NMR, ^1H-^1H COSY, DEPT, HMBC, HMQC, NOESY and ROESY techniques. Most of these novel taxane diterpenes posses different skeletons from usual taxoids consisting of a 6/8/6-membered ring system, of them, 3, 4 and 7 are rare example of taxoids involving a 6/12-membered bicyclic rings, of which the skeleton has been more recently reported from yew tree. 3,7-dien-9-one bicyclic taxanes (5, 6) with the verticillene skeletons have never been isolated from yew trees. 2(3→20)Abeotaxanes (10-13) were isolated for the first time from Taxus mairei. 14 was the second example of 11(15→1)abeotaxane with epoxidic ring at C-4(20) among more than 250 natural taxanes; compound 8 was a rare example of 6/8/6-membered ring system with a 14β-OH. In the bark, taxol and several taxoids bearing a xylose unit at C-7 were isolated as the major component. The bark of T. mairei is a suitable new resource for the production of taxol. In addition to taxoids, lignans, ecdysteroids, abietanes, 9(10→20)abeoabietanes, vomifoliol and its derivatives were also isolated from the bark of T. mairei.
天然有機化合物討論会の論文
1998-08-31

59(P21) 中国産イチイTaxus maireiに含まれるタキサンジテルペノイド類(ポスター発表の部)

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