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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  and  M. Uvais S. Sultanbawa 

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), 21α,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,21β-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.

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Article type: Paper
DOI: 10.1039/P19830002459
Citation: J. Chem. Soc., Perkin Trans. 1, 1983,0, 2459-2469
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    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. L. Gunatilaka, N. P. D. Nanayakkara and M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1, 1983, 0, 2459
    DOI: 10.1039/P19830002459

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