Further studies of the norditerpene (+)-harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: absolute configuration, cytotoxic and antifungal activities.
Harringtonolide (= hainanolide) is a complex polycyclic fused norditerpene isolated from CEPHALOTAXUS HARRINGTONIA var. DRUPACEA. In spite of its appealing biological properties - we measured an IC (50) 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 5 R,6 R,7 S,13 S,14 S,15 R,16 R. Detailed IN VITRO biological measurements are provided.
Laboratoire de Chimie et Biochimie des Substances Naturelles, Muséum National d'Histoire Naturelle, CNRS, Paris, France.
Laurent
L
Evanno
Akino
A
Jossang
Julie
J
Nguyen-Pouplin
Diane
D
Delaroche
Patrick
P
Herson
Mannan
M
Seuleiman
Bernard
B
Bodo
Bastien
B
Nay
D000935:Antifungal Agents / Q000302:isolation & purification; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification; D045744:Cell Line, Tumor; D032483:Cephalotaxus / Q000737:chemistry*; D006248:Harringtonines / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D008968:Molecular Conformation
D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D006248:Harringtonines; C020752:hainanolide