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- Ringbom, ThereseUppsala universitet,Avdelningen för farmakognosi (author)
Cox-2 inhibitory effects of naturally occurring and modified fatty acids
- Article/chapterEnglish2001
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- 2001-05-24
- American Chemical Society (ACS),2001
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- LIBRIS-ID:oai:DiVA.org:uu-51276
- https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-51276URI
- https://doi.org/10.1021/np000620dDOI
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- Language:English
- Summary in:English
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- In the search for new cyclooxygenase-2 (COX-2) selective inhibitors, the inhibitory effects of naturally occurring fatty acids and some of their structural derivatives on COX-2-catalyzed prostaglandin biosynthesis were investigated. Among these fatty acids, linoleic acid (LA), alpha-linolenic acid (alpha-LNA), myristic acid, and palmitic acid were isolated from a CH(2)Cl(2) extract of the plant Plantago major by bioassay-guided fractionation. Inhibitory effects of other natural, structurally related fatty acids were also investigated: stearic acid, oleic acid, pentadecanoic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA). Further, the inhibitory effects of these compounds on COX-2- and COX-1-catalyzed prostaglandin biosynthesis was compared with the inhibition of some synthesized analogues of EPA and DHA with ether or thioether functions. The most potent COX-2-catalyzed prostaglandin biosynthesis inhibitor was all-(Z)-5-thia-8,11,14,17-eicosatetraenoic acid (2), followed by EPA, DHA, alpha-LNA, LA, (7E,11Z,14Z,17Z)-5-thiaeicosa-7,11,14,17-tetraenoic acid, all-(Z)-3-thia-6,9,12,15-octadecatetraenoic acid, and (5E,9Z,12Z,15Z,18Z)-3-oxaheneicosa-5,9,12,15,18-pentaenoic acid, with IC(50) values ranging from 3.9 to180 microM. The modified compound 2 and alpha-LNA were most selective toward COX-2, with COX-2/COX-1 ratios of 0.2 and 0.1, respectively. This study shows that several of the natural fatty acids as well as all of the semisynthetic thioether-containing fatty acids inhibited COX-2-catalyzed prostaglandin biosynthesis, where alpha-LNA and compound 2 showed selectivity toward COX-2.
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- Huss, UlrikaUppsala universitet,Avdelningen för farmakognosi (author)
- Stenholm, ÅkeUppsala universitet,Avdelningen för farmakognosi (author)
- Flock, S (author)
- Skattebol, L (author)
- Perera, PremilaUppsala universitet,Avdelningen för farmakognosi (author)
- Bohlin, LarsUppsala universitet,Avdelningen för farmakognosi (author)
- Uppsala universitetAvdelningen för farmakognosi (creator_code:org_t)
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- In:Journal of natural products (Print): American Chemical Society (ACS)64:6, s. 745-7490163-38641520-6025
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