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Stemodin-derived analogues with lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation inhibitory activities

Floyd A. Russell ; Vanisree Mulabagal ; Dwayne R. Thompson ; Marvadeen A. Singh-Wilmot ; William F. Reynolds ; Muraleedharan G. Nair ; Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; Paul B. Reese
Phytochemistry (0031-9422). Vol. 72 (2011), 18, p. 2361-2368.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: Stemodia maritima L., Plantaginaceae, Diterpene, Stemodane, Bioassay, Lipid peroxidation, Cyclooxygenase enzyme, Tumour cell proliferation



Denna post skapades 2011-10-25. Senast ändrad 2012-01-05.
CPL Pubid: 147684

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Oorganisk miljökemi (2005-2014)

Ämnesområden

Kemi
Fasta tillståndets kemi
Organisk kemi
Organisk syntes
Bioorganisk kemi
Strukturbiologi
Biokemi
Läkemedelskemi
Kemi
Medicinsk bioteknologi (med inriktning mot cellbiologi)

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