TY - JOUR
T1 - Studies on terpenoids and steroids. Part 1. Structures of six novel 27-hydroxy and 6β-hydroxy di- and tri-oxygenated D
T2 - A-friedo-oleanane triterpenes from Kokoona zeylanica
AU - Gunatilaka, A. A.Leslie
AU - Nanayakkara, N. P.Dhammika
AU - Sultanbawa, M. Uvais S.
PY - 1983
Y1 - 1983
N2 - 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.
AB - 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.
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U2 - 10.1039/p19830002459
DO - 10.1039/p19830002459
M3 - Article
AN - SCOPUS:37049107405
SN - 1472-7781
SP - 2459
EP - 2469
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -