Transformations of Manool. Tri- and Tetracyclic Norditerpenoids with in Vitro Activity against Plasmodium falciparum

The known 17-norisopimar-15-ene-8β,13β-diol (5) and five new semisynthetic norditerpenoids, ethyl 17-norabiet-13(15)-E-en-8β-ol-16-oate (6), ethyl 17-norabiet-13(15)-Z-en-8β-ol-16-oate (7), 17-norpimaran-13α-ethoxy-8,16-olactone (8), 17-norisopimarane-8β,15-diol (9), and 17-norarabiet-13(15)-ene-8β,...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2007-08, Vol.70 (8), p.1253-1258
Hauptverfasser:	van Wyk, Albert W. W, Lobb, Kevin A, Caira, Mino R, Hoppe, Heinrich C, Davies-Coleman, Michael T
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Antibiotics. Antiinfectious agents. Antiparasitic agents antimalarials Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antiparasitic agents Biological and medical sciences chemical structure Crystallography, X-Ray Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology diterpenoids Erythrocytes - metabolism hemolysis human health Humans isopimarane diterpenes labdane diterpenes manool Medical sciences Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pharmacology. Drug treatments Plasmodium falciparum Plasmodium falciparum - drug effects Platycladus orientalis spectral analysis synthetic products
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Zusammenfassung:	The known 17-norisopimar-15-ene-8β,13β-diol (5) and five new semisynthetic norditerpenoids, ethyl 17-norabiet-13(15)-E-en-8β-ol-16-oate (6), ethyl 17-norabiet-13(15)-Z-en-8β-ol-16-oate (7), 17-norpimaran-13α-ethoxy-8,16-olactone (8), 17-norisopimarane-8β,15-diol (9), and 17-norarabiet-13(15)-ene-8β,16-diol (10), were prepared from manool (11). Standard spectroscopic data including X-ray crystal analysis were used to determine the structures of 5−10. All five compounds exhibited in vitro antiplasmodial activity against the malarial parasite Plasmodium falciparum at varying μg mL-1 concentrations.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np0701071