Structure elucidation and complete NMR spectral assignments of a new taxane glycoside from the needles ofTaxus cuspidata

Abstract

A new taxane glycoside was isolated from a methanol extract of the needles of Taxus cuspidata. The structure was established as 2alpha,9alpha,10beta-triacetoxytaxa-4(20),11-dien-13-one-5alpha-O-beta-D-glucopyranoside (1) on the basis of 1D- and 2D NMR and high-resolution fast atom bombardment mass spectral analyses.

Diterpenoids

“…141 A number of NMR studies have been reported on taxane derivatives. [142][143][144] The chemistry of the taxanes has continued to be explored in the context of evaluating structure-activity relationships. 145-150…”

Monitoring of aglycons of yew glycosides (3,5‐dimethoxyphenol, myrtenol and 1‐octen‐3‐ol) as first indicator of yew presence

“…[2][3][4] Other compounds of yew as taxane-derived molecules have shown cytotoxic properties and have led to the development of anti-cancer drugs. Among these alkaloids, taxine B was found to be responsible for the main toxicological effects due to its inhibition of calcium and sodium transport across the cell membrane of cardiac myocytes.…”

“…Among these alkaloids, taxine B was found to be responsible for the main toxicological effects due to its inhibition of calcium and sodium transport across the cell membrane of cardiac myocytes. [2][3][4] Other compounds of yew as taxane-derived molecules have shown cytotoxic properties and have led to the development of anti-cancer drugs. [5] Accidental ingestions in small quantities occur quite often with children.…”

A Novel Taxane 13-Glucoside and Other Taxanes from the Leaves ofTaxus cuspidata

“…T. cuspidata is one of the most extensively investigated yews, and more than 120 taxanes have been isolated from it [1][2][3][4][5][6]. As a continuation of our research on plants from the Taxus genus, we reinvestigated the leaves of T. cuspidata collected at Sendai, Japan [7][8][9][10][11][12][13][14][15], and isolated three new taxanes (l " Fig. 1 [10,11,16]).…”

“…As a continuation of our research on plants from the Taxus genus, we reinvestigated the leaves of T. cuspidata collected at Sendai, Japan [7][8][9][10][11][12][13][14][15], and isolated three new taxanes (l " Fig. 1 [10,11,16]). The spectral data due to the taxane moiety resembled those of the known taxane 2α,9α,10βtriacetoxytaxa-4(20),11-diene-5α,13α-diol, which was isolated from T. chinensis var.…”