Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids

A. A.Lesdie Gunatilaka; Bhavani Dhanabalasingham; Veranja Karunaratne; Tohru Kikuchi; Yasuhiro Tezuka

doi:10.1016/S0040-4020(01)80566-4

Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids

A. A.Lesdie Gunatilaka, Bhavani Dhanabalasingham, Veranja Karunaratne, Tohru Kikuchi, Yasuhiro Tezuka

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

27 Scopus citations

Abstract

The structure of epi-kokoondiol isolated from the outer root bark of Salacia reticulata var. β-diandra has been elucidated as 21α,26-dihydroxy-D:A-friedo-oleanan-3-one (1) by the application of 2D and NOE difference NMR spectroscopy. Reinvestigation of some KoKoona triterpenoids by NOE difference spectroscopy led to the revision of the structures of kokoondiol, kokoononol, kokzeylanol, kokoonol, and kokzeylanonol as 21β,26-dihydroxy-D:A-friedo-oleanan-3-one (2), 26-hydroxy-D:A-friedo-oleanane-3,21-dione (3), 6β,26-dihydroxy-D:A-friedo-oleanan-3-one (4) 26-hydroxy-D:A-friedo-oleanan-3-one (5), and 6β,26-dihydroxy-D:A-friedo-oleanane-3,21-dione (6), respectively.

Original language	English (US)
Pages (from-to)	10397-10404
Number of pages	8
Journal	Tetrahedron
Volume	49
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4020(01)80566-4
State	Published - 1993
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Gunatilaka, A. A. L., Dhanabalasingham, B., Karunaratne, V., Kikuchi, T., & Tezuka, Y. (1993). Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids. Tetrahedron, 49(45), 10397-10404. https://doi.org/10.1016/S0040-4020(01)80566-4

Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids. / Gunatilaka, A. A.Lesdie; Dhanabalasingham, Bhavani; Karunaratne, Veranja; Kikuchi, Tohru; Tezuka, Yasuhiro.

In: Tetrahedron, Vol. 49, No. 45, 1993, p. 10397-10404.

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

Gunatilaka, AAL, Dhanabalasingham, B, Karunaratne, V, Kikuchi, T & Tezuka, Y 1993, 'Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids', Tetrahedron, vol. 49, no. 45, pp. 10397-10404. https://doi.org/10.1016/S0040-4020(01)80566-4

Gunatilaka, A. A.Lesdie ; Dhanabalasingham, Bhavani ; Karunaratne, Veranja ; Kikuchi, Tohru ; Tezuka, Yasuhiro. / Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids. In: Tetrahedron. 1993 ; Vol. 49, No. 45. pp. 10397-10404.

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abstract = "The structure of epi-kokoondiol isolated from the outer root bark of Salacia reticulata var. β-diandra has been elucidated as 21α,26-dihydroxy-D:A-friedo-oleanan-3-one (1) by the application of 2D and NOE difference NMR spectroscopy. Reinvestigation of some KoKoona triterpenoids by NOE difference spectroscopy led to the revision of the structures of kokoondiol, kokoononol, kokzeylanol, kokoonol, and kokzeylanonol as 21β,26-dihydroxy-D:A-friedo-oleanan-3-one (2), 26-hydroxy-D:A-friedo-oleanane-3,21-dione (3), 6β,26-dihydroxy-D:A-friedo-oleanan-3-one (4) 26-hydroxy-D:A-friedo-oleanan-3-one (5), and 6β,26-dihydroxy-D:A-friedo-oleanane-3,21-dione (6), respectively.",

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Studies on terpenoids and stereoids. Part 27. Structure of a D:A-friedo-oleanane triterpenoid from salacia reticulata and revision of the structures of kokoonol and kokzeylanol series of triterpenoids

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