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Enhanced antiamyloidal activity of hydroxy cinnamic acids by enzymatic esterification with alkyl alcohols
Author(s) -
Kondo Hazuki,
Sugiyama Haruka,
Katayama Shigeru,
Nakamura Soichiro
Publication year - 2014
Publication title -
biotechnology and applied biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 70
eISSN - 1470-8744
pISSN - 0885-4513
DOI - 10.1002/bab.1182
Subject(s) - chemistry , lipophilicity , cinnamic acid , alkyl , ferulic acid , organic chemistry , lipase , caffeic acid , candida antarctica , phenols , peptide , enzyme , stereochemistry , biochemistry , antioxidant
Lipophilic derivatives of hydroxyl cinnamic acids ( HCA s) including caffeic acid ( CA ), ferulic acid, sinapic acid ( SA ), and chlorogenic acid were synthesized by esterification with butanol, octanol, or hexadecanol catalyzed by the lipase from C andida antarctica to investigate the effect of lipophilicity on their antiamyloidal activity assessed by the inhibitory activities toward fibrillization of amyloid β ( A β) peptide. Among them, CA showed the highest activity at 50 μM, reducing the amyloid fibril formation of A β to 34.4 ± 6.8%. The antiamyloidal effects of HCA s were enhanced by esterification with alkyl alcohols, and the longer alkyl chain tended to be more effective except for SA. A β fibril formation was suppressed by the hexadecyl ester of CA, which was reduced to 8.8 ± 2.3%. In contrast, those of octyl and butyl esters were 19.3 ± 2.3% and 41.6 ± 6.1%, respectively. These results show that lipophilicity plays an important role in the antiamyloidal activities of esterified phenolic compounds.