Three novel bicyclic taxane diterpenoids with verticillene skeleton from the needles of Chinese yew, Taxus chinensis var. mairei.
Three novel bicyclic taxane diterpenoids with the verticillene skeleton were isolated from the needles of Chinese yew, Taxus chinensis var. mairei. Their structures were established as (3E,7E)-2 alpha, 10 beta, 13 alpha, 20-tetraacetoxy-5 alpha-hydroxy-3,8-secotaxa-3,7,11-trien-9-one (1), (3E,7E)-2 alpha, 5 alpha, 10 beta, 13 alpha-tetraacetoxy-20-hydroxy-3,8-secotaxa-3,7,11-trien-9-one (2), and (3E,7E)-10 beta, 13 alpha-diacetoxy-2 alpha, 5 alpha, 20-trihydroxy-3,8-secotaxa-3,7,11-trien-9-one (3) on the basis of 1D, 2D NMR and HR-MS spectroscopic analysis. Verticillene skeleton was considered as the biogenetic intermediate of taxane diterpenoids, isolation of bicyclic taxane diterpenoids with verticillene skeleton from this plant provides direct proof for this hypothesis.
Shi
Q W
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Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Oritani
T
T
Sugiyama
T
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D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D013057:Spectrum Analysis; D014197:Trees / Q000737:chemistry*
C119819:10,13-diacetoxy-2,5,20-trihydroxy-3,8-secotaxa-3,7,11-trien-9-one; C119817:2,10,13,20-tetraacetoxy-5-hydroxy-3,8-secotaxa-3,7,11-trien-9-one; C119818:2,5,10,13-tetraacetoxy-20-hydroxy-3,8-secotaxa-3,7,11-trien-9-one; D001643:Bridged Bicyclo Compounds