Studies on terpenoids and steroids. Part 1. Structures of six novel 27-hydroxy and 6β-hydroxy di- and tri-oxygenated D: A-friedo-oleanane triterpenes from Kokoona zeylanica

A. A.Leslie Gunatilaka, N. P.Dhammika Nanayakkara, M. Uvais S. Sultanbawa

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

The benzene extract of the inner stem bark of Kokoona zeylanica Thwaites (Celastraceae) contains twelve D : A-friedo-oleananes of which nine are new. The new triterpenes have been classified under three series; kokoonol (3,27-dioxy and 3,21,27-trioxy), zeylanol (3,6-dioxy and 3,6,21 -trioxy), and kokzeylanol (3,6,27-trioxy and 3,6,21,27-tetraoxy). Six of these triterpenes belonging to the kokoonol and zeylanol series have been identified as 27-hydroxy-D : A-friedo-oleanan-3-one (4) (kokoonol), 27-hydroxy-D : A-friedo-oleanane-3,21 -dione (5) (kokoononol), 21 α,27-dihydroxy-D : A-friedo-oleanan-3-one (6) (kokoondiol), 6β-hydroxy-D : A-friedo-oleanan-3-one (21) (zeylanol), 6β-hydroxy-D : A-friedo-oleanane-3,21-dione (22) (zeylanonol) and 6β,21 β-dihydroxy-D : A-friedo-oleanan-3-one (23) (zeylandiol), by spectroscopic methods and chemical interconversions. The biosynthetic significance of 6-hydroxy-D : A-friedo-oleananes is discussed.

Original languageEnglish (US)
Pages (from-to)2459-2469
Number of pages11
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - Dec 1 1983
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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