The structure of taxinine, a nitrogen-free compound occurring in Taxus cuspidata.

Natural Taxanes: Developments Since 1828

“…Since then, huge amount of efforts and resources have been put in an extensively investigation on the potency of paclitaxel and its derivatives. Between the 1960s and 1970s, Japanese and American chemists isolated more than 20 taxanes from Japanese and European yews and most of them are derivatives of taxinine and baccatin. , The taxane-type structures of taxanes were established in 1963 with taxinine as the first example of this special group of natural products. , In 1980, Miller classified the 30 taxanes isolated before 1975 and discussed the naming system . Ten years later, in 1990, the number of compounds was almost doubled with 55 in three structural types .…”

Three Novel Bicyclic 3,8-Secotaxane Diterpenoids from the Needles of the Chinese Yew, Taxus chinensis var. mairei

“…Bicyclic 3,8-secotaxanes are a recently discovered class of taxanes with 6- and 12-membered rings and are very rare in nature: there are only six such compounds among over 250 natural taxanes. − Although this kind of skeleton was proposed by Pattenden et al , as a precursor in taxane biosynthesis as early as 1985, the biosynthesis of taxane diterpenes remains unclear . The early suggestion that taxanes are degraded triterpenoids related to quassinoids has been abandoned, and the current view is that taxanes are diterpenoids biosynthesized from geranylgeranyl diphosphate. , Clues might come from the isolation of compounds related to the alleged intermediates of the verticillene pathway and from a better knowledge of the structural variation within the natural taxanes. Although the structures of more than 250 taxanes have now been determined, only a few basic structural types exist, and variation is mostly found in the acylation pattern.…”

“…[22][23][24][25][26] Although this kind of skeleton was proposed by Pattenden et al 27,28 as a precursor in taxane biosynthesis as early as 1985, the biosynthesis of taxane diterpenes remains unclear. 29 The early suggestion that taxanes are degraded triterpenoids related to quassinoids 30 has been abandoned, and the current view is that taxanes are diterpenoids biosynthesized from geranylgeranyl diphosphate. 29,31 Clues might come from the isolation of compounds related to the alleged intermediates of the verticillene pathway and from a better knowledge of the structural variation within the natural taxanes.…”

Four new epoxy taxanes from needles of Taxus cuspidata (Taxaceae)

“…Although many taxoids have been isolated to date, new taxoids continue to be discovered [7][8][9], and some of them could become precursors of paclitaxel and its analogs and some of them showed new activity [10]. Taxus cuspidata is one of the earliest and most extensively studied species [11,12]. * In the previous works we have reported many new taxoids from this species [13][14][15][16].…”