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

Access to Document

10.1016/S0040-4020(01)80566-4

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

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.

@article{7c9dc0642d2441758bf037646470ff43,

title = "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",

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.",

author = "Gunatilaka, {A. A.Lesdie} and Bhavani Dhanabalasingham and Veranja Karunaratne and Tohru Kikuchi and Yasuhiro Tezuka",

year = "1993",

doi = "10.1016/S0040-4020(01)80566-4",

language = "English (US)",

volume = "49",

pages = "10397--10404",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "45",

}

TY - JOUR

T1 - 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

AU - Gunatilaka, A. A.Lesdie

AU - Dhanabalasingham, Bhavani

AU - Karunaratne, Veranja

AU - Kikuchi, Tohru

AU - Tezuka, Yasuhiro

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0027362632&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027362632&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)80566-4

DO - 10.1016/S0040-4020(01)80566-4

M3 - Article

AN - SCOPUS:0027362632

VL - 49

SP - 10397

EP - 10404

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 45

ER -