Stemodin-derived analogues with lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation inhibitory activities
Artikel i vetenskaplig tidskrift, 2011

A series of analogues, derived from the antiviral and cytotoxic diterpene stemodin, were prepared and evaluated for their lipid peroxidation (LPO), cyclooxygenase enzyme-1 (COX-1) and -2 (COX-2), and tumour cell proliferation inhibitory activities. Oxidation of stemodin produced stemodinone, which was then converted to stemod-12-en-2-one. Reaction of the latter under Petrow conditions (bromine; silver acetate/pyridine) yielded mainly dibrominated abeo-stachanes. Solvolysis of the dibromo compounds gave products of hydrolysis, some with rearranged skeleta. In the lipid peroxidation inhibitory assay three of the compounds exhibited prominent activity. Interestingly, all the analogues showed higher COX-1 enzyme inhibition than COX-2. Although a few of the diterpenes limited the growth of some human tumour cell lines, most compounds induced proliferation of such cells.

Tumour cell proliferation

Cyclooxygenase enzyme

Lipid peroxidation

Stemodane

Bioassay

Stemodia maritima L.

Diterpene

Plantaginaceae

Författare

Floyd A. Russell

University of the West Indies

Vanisree Mulabagal

Michigan State University

Dwayne R. Thompson

University of the West Indies

Marvadeen A. Singh-Wilmot

University of the West Indies

William F. Reynolds

University of Toronto

Muraleedharan G. Nair

King Saud University

Michigan State University

Vratislav Langer

Chalmers, Kemi- och bioteknik, Oorganisk miljökemi

Paul B. Reese

University of the West Indies

Phytochemistry

0031-9422 (ISSN)

Vol. 72 18 2361-2368

Ämneskategorier

Oorganisk kemi

Biokemi och molekylärbiologi

Annan medicinsk grundvetenskap

Strukturbiologi

Medicinsk bioteknologi (med inriktning mot cellbiologi (inklusive stamcellsbiologi), molekylärbiologi, mikrobiologi, biokemi eller biofarmaci)

Läkemedelskemi

Kemi

Organisk kemi

Fundament

Grundläggande vetenskaper

DOI

10.1016/j.phytochem.2011.08.024