Stemodin-derived analogues with lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation inhibitory activities
Journal article, 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
Author
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, Chemical and Biological Engineering, Environmental Inorganic Chemistry
Paul B. Reese
University of the West Indies
Phytochemistry
0031-9422 (ISSN)
Vol. 72 18 2361-2368Subject Categories
Inorganic Chemistry
Biochemistry and Molecular Biology
Other Basic Medicine
Structural Biology
Medical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy)
Medicinal Chemistry
Chemical Sciences
Organic Chemistry
Roots
Basic sciences
DOI
10.1016/j.phytochem.2011.08.024