Novel taxoids from the Chinese yew Taxus yunnanensis

Sheng Hong Li, Hongjie ZHANG*, Xue Mei Niu, Ping Yao, Han Dong Sun, Harry H.S. Fong

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Six new taxoids, taxuyunnanines W (1), X (2), Y (3), Z (5), 10-deacetyl-10-(β-glucopyranosyl)-yunnanxane (8), and 7-(β-xylosyl)-N-methyl-taxol C (10), as well as taxuchin B (4) and yunnanxane (7), have been isolated from the bark of Taxus yunnanensis. Compounds 1 and 2 were characterized as 11(15→1)-abeo taxoids containing an orthoester group, which have not been reported from any Taxus plants to date; isolates 3 and 5 are the examples of taxanes having a tetrahydronfuran ring, being reported only for the second time; and 8 is the first natural 6/8/6 skeletal type taxane glucosidic form. This is also the first report of a co-occurrence of xylosidation and N-methylation in a taxane (10). Compound 4 is the only known chlorine-containing taxane found in nature thus far, and is being reported from this plant for the first time. The structures were determined by spectroscopic and chemical means including 1D and 2D NMR spectra.

Original languageEnglish
Pages (from-to)37-45
Number of pages9
JournalTetrahedron
Volume59
Issue number1
DOIs
Publication statusPublished - 1 Jan 2003

Scopus Subject Areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

User-Defined Keywords

  • 10-deacetyl-10-(β-glucopyranosyl)-yunnanxane
  • 7-(β-xylosyl)-N-methyl-taxol C
  • Abeotaxoids
  • Barks
  • C-2(20) epoxide
  • Orthoester
  • Taxaceae
  • Taxane glycosides
  • Taxus yunnanensis
  • Taxuyunnanines W-Z

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