Studies on terpenoids and steroids. Part 10.1 structures of four new natural phenolic D: A-friedo-24-noroleanane triterpenoids2

Chandra B. Gamlath; Kamal B. Gunaherath; A. A. Leslie Gunatilaka

doi:10.1039/P19870002849

Studies on terpenoids and steroids. Part 10.¹ structures of four new natural phenolic D: A-friedo-24-noroleanane triterpenoids²

Chandra B. Gamlath
, Kamal B. Gunaherath
, A. A. Leslie Gunatilaka

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

The three new phenolic nortriterpenes, demethylzeylasteral, zeylasteral, and demethylzeylasterone, isolated from Kokoona zeylanica (Celastraceae), have been shown to be 2,3-dihydroxy-6,23-dioxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraen-29-oic acid (5), its methyl ester (6), and 2,3-dihydroxy-6-oxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraene-23,29-dioic acid (7), respectively. The structure of the new phenolic (9 → 8)-‘D’:‘A’- friedo -24-noroleanane triterpene obtained from ‘kokum soap’ has been established as 23-oxoisopristimerin III (11) on the basis of spectroscopic evidence. The biosynthetic significance of 23-oxoisopristimerin III is discussed.

Original language	English (US)
Pages (from-to)	2849-2854
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19870002849
State	Published - 1987
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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title = "Studies on terpenoids and steroids. Part 10.1 structures of four new natural phenolic D: A-friedo-24-noroleanane triterpenoids2",

abstract = "The three new phenolic nortriterpenes, demethylzeylasteral, zeylasteral, and demethylzeylasterone, isolated from Kokoona zeylanica (Celastraceae), have been shown to be 2,3-dihydroxy-6,23-dioxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraen-29-oic acid (5), its methyl ester (6), and 2,3-dihydroxy-6-oxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraene-23,29-dioic acid (7), respectively. The structure of the new phenolic (9 → 8)-{\textquoteleft}D{\textquoteright}:{\textquoteleft}A{\textquoteright}- friedo -24-noroleanane triterpene obtained from {\textquoteleft}kokum soap{\textquoteright} has been established as 23-oxoisopristimerin III (11) on the basis of spectroscopic evidence. The biosynthetic significance of 23-oxoisopristimerin III is discussed.",

author = "Gamlath, \{Chandra B.\} and Gunaherath, \{Kamal B.\} and \{Leslie Gunatilaka\}, \{A. A.\}",

year = "1987",

doi = "10.1039/P19870002849",

language = "English (US)",

pages = "2849--2854",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1470-4358",

publisher = "Chemical Society",

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T1 - Studies on terpenoids and steroids. Part 10.1 structures of four new natural phenolic D

T2 - A-friedo-24-noroleanane triterpenoids2

AU - Gamlath, Chandra B.

AU - Gunaherath, Kamal B.

AU - Leslie Gunatilaka, A. A.

PY - 1987

Y1 - 1987

N2 - The three new phenolic nortriterpenes, demethylzeylasteral, zeylasteral, and demethylzeylasterone, isolated from Kokoona zeylanica (Celastraceae), have been shown to be 2,3-dihydroxy-6,23-dioxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraen-29-oic acid (5), its methyl ester (6), and 2,3-dihydroxy-6-oxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraene-23,29-dioic acid (7), respectively. The structure of the new phenolic (9 → 8)-‘D’:‘A’- friedo -24-noroleanane triterpene obtained from ‘kokum soap’ has been established as 23-oxoisopristimerin III (11) on the basis of spectroscopic evidence. The biosynthetic significance of 23-oxoisopristimerin III is discussed.

AB - The three new phenolic nortriterpenes, demethylzeylasteral, zeylasteral, and demethylzeylasterone, isolated from Kokoona zeylanica (Celastraceae), have been shown to be 2,3-dihydroxy-6,23-dioxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraen-29-oic acid (5), its methyl ester (6), and 2,3-dihydroxy-6-oxo-D: A-friedo-24-noroleana-1,3,5(10),7-tetraene-23,29-dioic acid (7), respectively. The structure of the new phenolic (9 → 8)-‘D’:‘A’- friedo -24-noroleanane triterpene obtained from ‘kokum soap’ has been established as 23-oxoisopristimerin III (11) on the basis of spectroscopic evidence. The biosynthetic significance of 23-oxoisopristimerin III is discussed.

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JO - Journal of the Chemical Society, Perkin Transactions 1

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Studies on terpenoids and steroids. Part 10.¹ structures of four new natural phenolic D: A-friedo-24-noroleanane triterpenoids²

Abstract

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