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

Abstract

Three new taxanes, 2α,9α,10β-triacetoxy-13α-(β-D-glucopyranosyloxy)taxa-4(20),11-dien-5α-ol (1), 5α,10β,13α-triacetoxytax-11-ene-2α,7β,9α,20-tetraol (2), and 5α,10β,13β-triacetoxy-2α,7β-dihydroxy-2(3 → 20)abeotaxa-4(20),11-dien-9-one (3), were isolated from the leaves of the Japanese yew, Taxus cuspidata. Compound 1 is the first example of a taxane with 13-glycosidic linkage.

Key words

Taxus cuspidata - Taxaceae - taxanes - taxane glucoside - yew - leaves

References

• 1 Parmer V S, Jha A, Bish K S, Taneja P, Sight S K, Kumar A, Poonam J R, Olsen C E. Constituents of yew trees.  Phytochemistry. 1999;  50 1267-1304
• 2 Appendino G. The structural elucidation of taxoids. Farina V The chemistry and pharmacology of taxol and its derivatives. Amsterdam; Elsevier 1995: 55-101
• 3 Shi Q W, Kiyota H. New natural taxane diterpenoids from Taxus species since 1999.  Chem Biodivers. 2006;  2 1597-1623
• 4 Kobayashi J, Shigemori H. Bioactive taxoids from the Japanese yew Taxus cuspidata.  Med Res Rev. 2002;  22 305-328
• 5 Shigemori H, Kobayashi J. Biological activity and chemistry of taxoids from the Japanese yew, Taxus cuspidata.  J Nat Prod. 2004;  67 245-256
• 6 Shi Q W, Wang Y F, Kiyota H. Phytochemical studies of taxane diterpenoids from yew trees. Brahmachari G Chemistry of natural products: recent trends & developments 2006. Kelara, India; Research Signpost 2006: 43-59
• 7 Shi Q W, Oritani T, Sugiyama T, Kiyota H, Horiguchi T. Three new rearranged taxane diterpenoids from the bark of Taxus chinensis var. mairei and the needles of Taxus cuspidata.  Heterocycles. 1999;  51 841-850
• 8 Shi Q W, Oritani T, Kiyota H. Three new taxoids from the leaves of the Japanese yew, Taxus cuspidata.  Nat Prod Lett. 2001;  15 55-62
• 9 Shi Q W, Li Z P, Zhao D, Gu J S, Oritani T, Kiyota H. New 2(3 → 20)abeotaxane and 3,11-cyclotaxane from needles of Taxus cuspidata.  Biosci Biotechnol Biochem. 2004;  68 1584-1587
• 10 Li L G, Cao C M, Huo C H, Zhang M, Shi Q W, Kiyota H. Structure elucidation and complete NMR spectral assignments of a new taxane glucoside form the needles of Taxus cuspidata.  Magn Reson Chem. 2005;  43 475-478
• 11 Wang C L, Zhang M L, Cao C M, Shi Q W, Kiyota H. First example of 11,12-epoxytaxane-glucoside from the needles of Taxus cuspidata.  Heterocycl Commun. 2005;  11 211-214
• 12 Shi Q W, Cao C M, Gu J S, Kiyota H. Four new epoxy taxanes from needles of Taxus cuspidata (Taxaceae).  Nat Prod Res. 2006;  20 173-179
• 13 Cao C M, Zhang M L, Wang Y F, Shi Q W, Yamada T, Kiyota H. Two new taxanes from the needles and branches bark of Taxus cuspidata.  Chem Biodivers. 2006;  3 1153-1161
• 14 Huo C H, Su X H, Li X, Chang X P, Li C F, Wang Y F, Shi Q W, Kiyota H. Structural determination of a new 2(3 → 20)abeotaxane with an unusual 13β-substitution pattern and a new 6/8/6-ring taxane from Taxus cuspidata.  Magn Reson Chem. 2007;  45 527-530
• 15 Shi Q W, Dong M, Huo C H, Su X H, Li X, Yamada T, Kiyota H. 7,8β-Dihydroponasterone A, a new phytoecdysteroid from the needles of the Japanese yew, Taxus cuspidata.  J Braz Chem Soc. 2007;  18 1801-1804
• 16 Tong X J, Fang W S, Zhou J Y, He C H, Chen W M, Fang Q C. Three new taxane diterpenoids from needles and stems of Taxus cuspidata.  J Nat Prod. 1995;  58 233-238
• 17 Shi Q W, Oritani T, Gu J S, Meng Q Z, Liu R L. Three new taxane diterpenoids from the seeds of the Chinese yew, Taxus chinensis var. mairei.  J Asian Nat Prod Rep. 2000;  2 311-319
• 18 Jaunzems J, Kashin D, Schönberger A, Kirschning A Synthesis of 13-O-glycosylated baccatin derivative was reported:. Polymer-bound diphenylphosphane hydrobromide, a mild acid for the activation of enol ethers: applications in polymer-assisted glycosidations.  Eur J Org Chem. 2004;  3435-3446
• 19 Shi Q W, Oritani T, Sugiyama T, Murakami R, Wei H Q. Six new taxane diterpenoids from the seeds of Taxus chinensis var. mairei and Taxus yunnanensis.  J Nat Prod. 1999;  62 1114-1118