Total synthesis and adjuvant activity of all stereoisomers of pinellic acid.
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.
Shirahata
Tatsuya
T
The Kitasato Institute for Life Science, School of Pharmaceutical Science, Kitasato University, Shirokane, Minatoku, Tokyo 108-8641, Japan.
Sunazuka
Toshiaki
T
Yoshida
Kiminari
K
Yamamoto
Daisuke
D
Harigaya
Yoshihiko
Y
Nagai
Takayuki
T
Kiyohara
Hiroaki
H
Yamada
Haruki
H
Kuwajima
Isao
I
Omura
Satoshi
S
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
D000276:Adjuvants, Immunologic; D000914:Antibodies, Viral; D005231:Fatty Acids, Unsaturated; D007070:Immunoglobulin A; D007074:Immunoglobulin G; C478149:pinellic acid