Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest

Maged Abdel-Kader; John M. Berger; Carla Slebodnick; Jeannine Hoch; Stan Malone; Jan H. Wisse; Marga C.M. Werkhoven; Steven Mamber; David G.I. Kingston

doi:10.1021/np0103261

Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest

Maged Abdel-Kader
, John M. Berger
, Carla Slebodnick
, Jeannine Hoch
, Stan Malone
, Jan H. Wisse
, Marga C.M. Werkhoven
, Steven Mamber
, David G.I. Kingston

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

47 Scopus citations

Abstract

Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.

Original language	English
Pages (from-to)	11-15
Number of pages	5
Journal	Journal of Natural Products
Volume	65
Issue number	1
DOIs	https://doi.org/10.1021/np0103261
State	Published - 2002
Externally published	Yes

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SDG 3 Good Health and Well-being

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10.1021/np0103261

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title = "Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest",

abstract = "Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.",

author = "Maged Abdel-Kader and Berger, \{John M.\} and Carla Slebodnick and Jeannine Hoch and Stan Malone and Wisse, \{Jan H.\} and Werkhoven, \{Marga C.M.\} and Steven Mamber and Kingston, \{David G.I.\}",

year = "2002",

doi = "10.1021/np0103261",

language = "English",

volume = "65",

pages = "11--15",

journal = "Journal of Natural Products",

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T1 - Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest

AU - Abdel-Kader, Maged

AU - Berger, John M.

AU - Slebodnick, Carla

AU - Hoch, Jeannine

AU - Malone, Stan

AU - Wisse, Jan H.

AU - Werkhoven, Marga C.M.

AU - Mamber, Steven

AU - Kingston, David G.I.

PY - 2002

Y1 - 2002

N2 - Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.

AB - Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.

UR - https://www.scopus.com/pages/publications/0036163274

U2 - 10.1021/np0103261

DO - 10.1021/np0103261

M3 - Article

C2 - 11809056

AN - SCOPUS:0036163274

SN - 0163-3864

VL - 65

SP - 11

EP - 15

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 1

ER -

Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest

Abstract

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