ABSTRACT
A p-quinone analog having the komaroviquinone pharmacophore fused with a more conformationally flexible cycloheptane ring, was semisynthesized from natural demethlsalvicanol isolated from Perovskia abrotanoides via four steps in 26% overall yield. The IC50 for the antitrypanosomal activity of the analog was 0.55 µM.
Subject(s)
Diterpenes , Quinones , Plant Extracts , Quinones/pharmacologyABSTRACT
Isetexane diterpene analogues were semisynthesized from demethylsalvicanol isolated from Perovskia abrotanoides (Labiatae). The structure and cytotoxic activity relationships (SAR) of the natural parent diterpene, demethylsalvicanol, and its semisynthetic analogues were studied by using P388 murine leukemia cells.
Subject(s)
Diterpenes/chemical synthesis , Diterpenes/pharmacology , Lamiaceae/chemistry , Leukemia P388/drug therapy , Animals , Cell Line, Tumor , Cell Proliferation/drug effects , Diterpenes/chemistry , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Mice , Molecular Conformation , Stereoisomerism , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
Seven known abietane diterpenoids and 11-O- and 12-O-acetylcarnosic acids were isolated from a methanol extract of Perovskia abrotanoides (Labiatae). Structure and cytotoxic activity relationships (SAR) of the natural and semisynthetic analogues of the presently isolated abietane diterpenoids were studied by using P388 murine leukemia cells.
Subject(s)
Abietanes/pharmacology , Lamiaceae/chemistry , Leukemia P388/drug therapy , Abietanes/chemistry , Abietanes/isolation & purification , Animals , Cell Line, Tumor , Cell Proliferation/drug effects , Drug Screening Assays, Antitumor , Mice , Molecular Conformation , Plants, Medicinal/chemistry , Stereoisomerism , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
S(R)()-Podolactone D (1), a new norditerpene dilactone having a methylsulfoxide moiety, was isolated from the leaves of Podocarpus macrophyllus D. Don var. maki Endl. along with known podolactone D (2, S(S)()-podolactone D). The structures and absolute configurations of compounds 1 and 2 were elucidated by spectral methods (HREIMS, IR, (1)H, (13)C, and 2D NMR) and finally confirmed by single-crystal X-ray analyses. The cytotoxic effects of compounds 1 and 2 on P388 murine leukemia cells were also examined.
