title: Total synthesis and adjuvant activity of all stereoisomers of pinellic acid.
abstract: Pinellic acid is a novel and potentially useful oral adjuvant when used in conjunction with intranasal inoculation of influenza HA vaccines. All stereoisomers of pinellic acid have been synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction, and their adjuvant activities were characterized. Among this series of isomers, 9S, 12S, 13S compound has the most potent adjuvant activity. Structure-activity relationships are discussed.
authors.affiliation: The Kitasato Institute for Life Science, School of Pharmaceutical Science, Kitasato University, Shirokane, Minatoku, Tokyo 108-8641, Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Shirahata
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Sunazuka
authors.forename: Kiminari
authors.initials: K
authors.lastname: Yoshida
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yamamoto
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Harigaya
authors.forename: Takayuki
authors.initials: T
authors.lastname: Nagai
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Kiyohara
authors.forename: Haruki
authors.initials: H
authors.lastname: Yamada
authors.forename: Isao
authors.initials: I
authors.lastname: Kuwajima
authors.forename: Satoshi
authors.initials: S
authors.lastname: Omura
mesh_terms: D000276:Adjuvants, Immunologic / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000914:Antibodies, Viral / Q000097:blood; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000494:pharmacology; D006900:Hydroxylation; D007070:Immunoglobulin A / Q000097:blood; D007074:Immunoglobulin G / Q000097:blood; D051379:Mice; D009975:Orthomyxoviridae / Q000187:drug effects / Q000276:immunology; D010084:Oxidation-Reduction; D030021:Pinellia / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000276:Adjuvants, Immunologic; D000914:Antibodies, Viral; D005231:Fatty Acids, Unsaturated; D007070:Immunoglobulin A; D007074:Immunoglobulin G; C478149:pinellic acid