Exploration of essential structure of malloapelta B for the inhibitory activity against TNF induced NF-κB activation

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dc.contributor.authorC V Luu-
dc.contributor.authorM V Chau-
dc.contributor.authorJung Joon Lee-
dc.contributor.authorS H Jung-
dc.date.accessioned2017-04-19T09:05:30Z-
dc.date.available2017-04-19T09:05:30Z-
dc.date.issued2006-
dc.identifier.issn0253-6269-
dc.identifier.uri10.1007/BF02973903ko
dc.identifier.urihttps://oak.kribb.re.kr/handle/201005/7660-
dc.description.abstractFor the exploration of pharmacophoric moiety of malloapelta B (1) possessing the inhibitory activity of NF-κB activation, structural variation of α,β-unsaturated carbonyl motif was attempted. 1 was reduced by catalytic hydrogenation, sodium borohydride, and lithium aluminumhydride. Catalytic hydrogenation with 30 psi or 15 psi of H2 gas of 1 generated 8-butyl-5,7-dimethoxy-2,2-dimethylchroman (2) and 1-(5,7-dimethoxy-2,2-dimethylchroman-8-yl)butan-1-one (3), respectively. Reduction with sodium borohydride occurred at the double bond of α,β-unsaturated ketone of 1 to give 1-(5,7-dimethoxy-2,2-dimethyl-2H- chromen-8-yl)butan-1-one (4). Reduction of 1 with lithium aluminumhydride and then quenched with methanol and water produced unexpected products, 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-3-methoxy-1-butene (5) and 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-3-hydroxy-1-butene (6). These are formed from the isomerization of initial product 9 through the continuous conjugate carbocation intermediate 11. Addition of ethylmagnesium bromide and dimethyl malonate anion to 1 gave the conjugate adducts 7 and 8. Ethylmagesium bromide and sodium borohydride reduction unusually gave the conjugate addition due to steric congestion around carbonyl group of 1. Compound 2 exhibits the reduced inhibitory activity against NF-κB activation and the others do not show the activity. Therefore α,β-unsaturated carbonyl group of 1 should be important for its inhibitory activity.-
dc.publisherPharmaceutical Soc Korea-
dc.titleExploration of essential structure of malloapelta B for the inhibitory activity against TNF induced NF-κB activation-
dc.title.alternativeExploration of essential structure of malloapelta B for the inhibitory activity against TNF induced NF-κB activation-
dc.typeArticle-
dc.citation.titleArchives of Pharmacal Research-
dc.citation.number10-
dc.citation.endPage844-
dc.citation.startPage840-
dc.citation.volume29-
dc.contributor.affiliatedAuthorJung Joon Lee-
dc.contributor.alternativeNameLuu-
dc.contributor.alternativeNameChau-
dc.contributor.alternativeName이정준-
dc.contributor.alternativeName정상훈-
dc.identifier.bibliographicCitationArchives of Pharmacal Research, vol. 29, no. 10, pp. 840-844-
dc.identifier.doi10.1007/BF02973903-
dc.subject.keywordEssential structure of malloapelta B-
dc.subject.keywordNF-κB activation-
dc.subject.localEssential structure of malloapelta B-
dc.subject.localNF-κB activation-
dc.description.journalClassY-
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