Phenylbutanoid and taxane-like metabolites from needles of Taxus brevifolia
1994
Chu, A. | Furlan, M. | Davin, L.B. | Zajicek, J. | Towers, G.H.N. | Soucy-Breau, C.M. | Rettig, S.J. | Croteau, R. | Lewis, N.G.
The structures for brevifoliol and three baccatin VI derivatives were revised to possess the novel 11(15 leads to 1)-abeotaxane tricylic skeleton based on X-ray crystallographic studies. Four more new rearranged taxane derivatives related to brevifoliol and the unusual phenylbutanoid, (-)-rhododendrol, were isolated from the needles of Taxus brevifolia. Their structures were established as 10 beta-benzoxy-5 alpha-(3'-dimethylamino-3'-phenyl)-propanoxy-1 beta-hydroxy-7 beta, 9 alpha, 13 alpha-triacetoxy-11(15 leads to 1)-abeotaxa-4(20),11-diene; 10 beta-benzoxy-1 beta-hydroxy-5 alpha-(3'-methylamino-3'-phenyl)-propanoxy-7 beta, 9 alpha, 13 alpha-triacetoxy-11(15 leads to 1)-abeotaxa-4(20),11-diene; 10 beta-benzoxy-5 alpha-cinnamoxy-1 beta-hydroxy-7 beta, 9 alpha, 13 alpha-triacetoxy-11(15 leads to 1)-abeotaxa-4(20),11-diene; 10 beta-benzoxy-1 beta, 5 alpha-dihydroxy-7 beta, 9 alpha, 13 alpha-triacetoxy-11 (15 leads to 1)-abeotaxa-4(20),11-diene and 2(R)-hydroxy-4-(4'-hydroxyphenyl)-butane.
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