Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids

A. A.Lesdie Gunatilaka, Bhavani Dhanabalasingham, Veranja Karunaratne, Tohru Kikuchi, Yasuhiro Tezuka

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

The structure of epi-kokoondiol isolated from the outer root bark of Salacia reticulata var. β-diandra has been elucidated as 21α,26-dihydroxy-D:A-friedo-oleanan-3-one (1) by the application of 2D and NOE difference NMR spectroscopy. Reinvestigation of some KoKoona triterpenoids by NOE difference spectroscopy led to the revision of the structures of kokoondiol, kokoononol, kokzeylanol, kokoonol, and kokzeylanonol as 21β,26-dihydroxy-D:A-friedo-oleanan-3-one (2), 26-hydroxy-D:A-friedo-oleanane-3,21-dione (3), 6β,26-dihydroxy-D:A-friedo-oleanan-3-one (4) 26-hydroxy-D:A-friedo-oleanan-3-one (5), and 6β,26-dihydroxy-D:A-friedo-oleanane-3,21-dione (6), respectively.

Original languageEnglish (US)
Pages (from-to)10397-10404
Number of pages8
JournalTetrahedron
Volume49
Issue number45
DOIs
StatePublished - 1993
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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