title: Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain.
abstract: Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r(2) = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.
authors: a The United Graduate School of Agricultural Sciences , Ehime University , Matsuyama , Japan.
authors: Fengxian
authors: F
authors: Zhu
authors: Zhongming
authors: Z
authors: Xu
authors: Lina
authors: L
authors: Yonekura
authors: Ronghua
authors: R
authors: Yang
authors: Hirotoshi
authors: H
authors: Tamura
mesh_terms: D000818:Animals; D018926:Anti-Allergic Agents / Q000737:chemistry* / Q000494:pharmacology*; D002109:Caffeic Acids / Q000737:chemistry; D002460:Cell Line / Q000187:drug effects; D002934:Cinnamates / Q000737:chemistry / Q000494:pharmacology*; D003373:Coumaric Acids / Q000737:chemistry; D053630:Depsides / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004952:Esters / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008407:Mast Cells / Q000276:immunology / Q000378:metabolism; D031343:Perilla / Q000737:chemistry; D011422:Propionates; D051381:Rats; D017455:Receptors, IgE / Q000378:metabolism; D013329:Structure-Activity Relationship; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism; D000097123:Rosmarinic Acid
chemical_list: D018926:Anti-Allergic Agents; D002109:Caffeic Acids; D002934:Cinnamates; D003373:Coumaric Acids; D053630:Depsides; D004952:Esters; D011422:Propionates; D017455:Receptors, IgE; D001619:beta-N-Acetylhexosaminidases; D000097123:Rosmarinic Acid; C553474:FCER1A protein, rat; C495469:p-coumaric acid
keywords: antiallergic activity; bulkiness; esterification; hydrophobicity; rosmarinic acid