Studies on terpenoids and steroids. Part 3. Structure and synthesis of a new phenolic D: A-friedo-24-noroleanane triterpenoid, zeylasterone, from Kokoona zeylanica

G. M Kamal B Gunaherath, Leslie Gunatilaka

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Zeylasterone, the first of a novel series of natural phenolic nortriterpenes from Kokoona zeylanica (Celastraceae) and ' kokum soap ' has been shown to be 29-methyl hydrogen 2,3-dihydroxy-6-oxo-D:A-friedo-24-noroleana-1,3, 5(10),7-tetraene-23,29-dioate (3) on the basis of spectroscopic and chemical evidence. Trimethylzeylasterone (8) has been synthesized from pristimerin, a quinone methide present in K. zeylanica and ' kokum soap '. The biosynthetic importance of some triterpenoids of K. zeylanica is discussed.

Original languageEnglish (US)
Pages (from-to)2845-2850
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1983
Externally publishedYes

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Soaps (detergents)
Terpenes
Steroids
Hydrogen
zeylasterone
quinone methide
pristimerin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Zeylasterone, the first of a novel series of natural phenolic nortriterpenes from Kokoona zeylanica (Celastraceae) and ' kokum soap ' has been shown to be 29-methyl hydrogen 2,3-dihydroxy-6-oxo-D:A-friedo-24-noroleana-1,3, 5(10),7-tetraene-23,29-dioate (3) on the basis of spectroscopic and chemical evidence. Trimethylzeylasterone (8) has been synthesized from pristimerin, a quinone methide present in K. zeylanica and ' kokum soap '. The biosynthetic importance of some triterpenoids of K. zeylanica is discussed.",
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AU - Gunatilaka, Leslie

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AB - Zeylasterone, the first of a novel series of natural phenolic nortriterpenes from Kokoona zeylanica (Celastraceae) and ' kokum soap ' has been shown to be 29-methyl hydrogen 2,3-dihydroxy-6-oxo-D:A-friedo-24-noroleana-1,3, 5(10),7-tetraene-23,29-dioate (3) on the basis of spectroscopic and chemical evidence. Trimethylzeylasterone (8) has been synthesized from pristimerin, a quinone methide present in K. zeylanica and ' kokum soap '. The biosynthetic importance of some triterpenoids of K. zeylanica is discussed.

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