Further studies of the norditerpene (+)-Harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: Absolute configuration, cytotoxic and antifungal activities

Laurent Evanno; Akino Jossang; Julie Nguyen-Pouplin; Diane Delaroche; Patrick Herson; Mannan Seuleiman; Bernard Bodo; Bastien Nay

doi:10.1055/s-2008-1074546

Further studies of the norditerpene (+)-Harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: Absolute configuration, cytotoxic and antifungal activities

Laurent Evanno
, Akino Jossang
, Julie Nguyen-Pouplin
, Diane Delaroche
, Patrick Herson
, Mannan Seuleiman
, Bernard Bodo
, Bastien Nay

CNRS/Museum National d'Histoire Naturelle/IRD/UPMC
Université Pierre et Marie Curie
Sorbonne Université

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

Abstract

Harringtonolide (=hainanolide) is a complex polycyclic fused norditerpene isolated from Cephalotaxus harringtonia var. drupacea. In spite of its appealing biological properties - we measured an IC₅₀ of 43 nM on KB cells and a significant antifungal activity - its absolute configuration has not yet been firmly established. This was done herein using X-ray anomalous scattering after bromination of the tropone ring, unambiguously giving the stereochemistry 5R,6K,7S,13S,14S,15R,16R. Detailed in vitro biological measurements are provided.

Original language	English
Pages (from-to)	870-872
Number of pages	3
Journal	Planta Medica
Volume	74
Issue number	8
DOIs	https://doi.org/10.1055/s-2008-1074546
Publication status	Published - 1 Jun 2008
Externally published	Yes

Keywords

Absolute configuration
Biological activities
Cephalotaxaceae
Cephalotaxus harringtonia var. drupacea
Norditerpenes
X-ray diffraction

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10.1055/s-2008-1074546

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title = "Further studies of the norditerpene (+)-Harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: Absolute configuration, cytotoxic and antifungal activities",

abstract = "Harringtonolide (=hainanolide) is a complex polycyclic fused norditerpene isolated from Cephalotaxus harringtonia var. drupacea. In spite of its appealing biological properties - we measured an IC50 of 43 nM on KB cells and a significant antifungal activity - its absolute configuration has not yet been firmly established. This was done herein using X-ray anomalous scattering after bromination of the tropone ring, unambiguously giving the stereochemistry 5R,6K,7S,13S,14S,15R,16R. Detailed in vitro biological measurements are provided.",

keywords = "Absolute configuration, Biological activities, Cephalotaxaceae, Cephalotaxus harringtonia var. drupacea, Norditerpenes, X-ray diffraction",

author = "Laurent Evanno and Akino Jossang and Julie Nguyen-Pouplin and Diane Delaroche and Patrick Herson and Mannan Seuleiman and Bernard Bodo and Bastien Nay",

year = "2008",

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doi = "10.1055/s-2008-1074546",

language = "English",

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T1 - Further studies of the norditerpene (+)-Harringtonolide isolated from Cephalotaxus harringtonia var. drupacea

T2 - Absolute configuration, cytotoxic and antifungal activities

AU - Evanno, Laurent

AU - Jossang, Akino

AU - Nguyen-Pouplin, Julie

AU - Delaroche, Diane

AU - Herson, Patrick

AU - Seuleiman, Mannan

AU - Bodo, Bernard

AU - Nay, Bastien

PY - 2008/6/1

Y1 - 2008/6/1

N2 - Harringtonolide (=hainanolide) is a complex polycyclic fused norditerpene isolated from Cephalotaxus harringtonia var. drupacea. In spite of its appealing biological properties - we measured an IC50 of 43 nM on KB cells and a significant antifungal activity - its absolute configuration has not yet been firmly established. This was done herein using X-ray anomalous scattering after bromination of the tropone ring, unambiguously giving the stereochemistry 5R,6K,7S,13S,14S,15R,16R. Detailed in vitro biological measurements are provided.

AB - Harringtonolide (=hainanolide) is a complex polycyclic fused norditerpene isolated from Cephalotaxus harringtonia var. drupacea. In spite of its appealing biological properties - we measured an IC50 of 43 nM on KB cells and a significant antifungal activity - its absolute configuration has not yet been firmly established. This was done herein using X-ray anomalous scattering after bromination of the tropone ring, unambiguously giving the stereochemistry 5R,6K,7S,13S,14S,15R,16R. Detailed in vitro biological measurements are provided.

KW - Absolute configuration

KW - Biological activities

KW - Cephalotaxaceae

KW - Cephalotaxus harringtonia var. drupacea

KW - Norditerpenes

KW - X-ray diffraction

U2 - 10.1055/s-2008-1074546

DO - 10.1055/s-2008-1074546

M3 - Article

C2 - 18523925

AN - SCOPUS:47249128631

SN - 0032-0943

VL - 74

SP - 870

EP - 872

JO - Planta Medica

JF - Planta Medica

IS - 8

ER -

Further studies of the norditerpene (+)-Harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: Absolute configuration, cytotoxic and antifungal activities

Abstract

Keywords

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