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

被引:69
作者
Evanno, Laurent
Jossang, Akino
Nguyen-Pouplin, Julie
Delaroche, Diane [2 ]
Herson, Patrick [3 ]
Seuleiman, Mannan [3 ]
Bodo, Bernard
Nay, Bastien [1 ]
机构
[1] Museum Natl Hist Nat, Lab Chim & Biochim Subst Nat, CNRS, UMR 5154,Dept RDDM, F-75005 Paris, France
[2] Univ Paris 06, Lab Synth Struct & Fonct Mol Bioact, Paris, France
[3] Univ Paris 06, CNRS, Lab Chim Inorgan & Mat Mol, Paris, France
关键词
Cephalotaxus harringtonia var. drupacea; Cephalotaxaceae; nor-diterpenes; absolute configuration; X-ray diffraction; biological activities;
D O I
10.1055/s-2008-1074546
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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 5R,6R,7S,13S,14S,15R,16R. Detailed in vitro biological measurements are provided.
引用
收藏
页码:870 / 872
页数:3
相关论文
共 22 条
[1]  
Bao G H, 1983, Zhongguo Yi Xue Ke Xue Yuan Xue Bao, V5, P89
[2]   DETERMINATION OF THE ABSOLUTE CONFIGURATION OF OPTICALLY ACTIVE COMPOUNDS BY MEANS OF X-RAYS [J].
BIJVOET, JM ;
PEERDEMAN, AF ;
VANBOMMEL, AJ .
NATURE, 1951, 168 (4268) :271-272
[3]   HARRINGTONOLIDE, A PLANT-GROWTH INHIBITORY TROPONE FROM CEPHALOTAXUS-HARRINGTONIA (FORBES) K KOCH [J].
BUTA, JG ;
FLIPPEN, JL ;
LUSBY, WR .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :1002-1003
[4]   Two new lactones from Cephalotaxus fortunei var. alpnia [J].
Du, J ;
Chiu, MH ;
Nie, RL .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12) :1664-1665
[5]   Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions [J].
Evanno, Laurent ;
Deville, Alexandre ;
Dubost, Lionel ;
Chiaroni, Angele ;
Bodo, Bernard ;
Nay, Bastien .
TETRAHEDRON LETTERS, 2007, 48 (16) :2893-2896
[6]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[7]   HARRINGTONOLIDE - COMPLEX TROPONE [J].
FLIPPENANDERSON, JL ;
DUESLER, E .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (MAY) :1253-1254
[8]   Structural and stereochemical studies of C-21 terpenoids from Mediterranean Spongiidae sponges [J].
Fontana, A ;
Albarella, L ;
Scognamiglio, G ;
Uriz, M ;
Cimino, G .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (09) :869-872
[9]   Synthesis of the unusual diterpenoid tropones hainanolidol and harringtonolide [J].
Frey, B ;
Wells, AP ;
Rogers, DH ;
Mander, LN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1914-1915
[10]  
Fukuyama Y, 1999, CHEM PHARM BULL, V47, P454