Syntheses and mucosal adjuvant activity of simplified oleanolic acid saponins possessing cinnamoyl ester

Tatsuya Shirahata; Takayuki Nagai; Nozomu Hirata; Masaki Yokoyama; Tatsuya Katsumi; Naruki Konishi; Takashi Nishino; Kazuishi Makino; Haruki Yamada; Eisuke Kaji; Hiroaki Kiyohara; Yoshinori Kobayashi

doi:10.1016/j.bmc.2016.09.052

Syntheses and mucosal adjuvant activity of simplified oleanolic acid saponins possessing cinnamoyl ester

Bioorg Med Chem. 2017 Mar 15;25(6):1747-1755. doi: 10.1016/j.bmc.2016.09.052. Epub 2016 Sep 22.

Affiliations

¹ School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
² Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.

PMID: 28237555
DOI: 10.1016/j.bmc.2016.09.052

Abstract

A series of new simplified oleanolic acid saponins with a glycosyl ester moiety at C28, were efficiently prepared. Furthermore, the effect of nasal administration of the synthetic oleanolic acid saponins on the nasal anti-influenza virus antibody titer against secondary nasal inoculation of the influenza split vaccine was examined. The result revealed cinnamoyl saponin as a suitable candidate vaccine adjuvant.

Keywords: Glycosylation; Mucosal adjuvant; Saponin; Vaccine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adjuvants, Immunologic / chemical synthesis*
Adjuvants, Immunologic / chemistry
Adjuvants, Immunologic / pharmacology*
Administration, Intranasal
Animals
Influenza Vaccines / administration & dosage*
Mice
Mice, Inbred BALB C
Nasal Mucosa / drug effects*
Oleanolic Acid / chemistry*
Saponins / chemical synthesis*
Saponins / chemistry
Saponins / pharmacology*
Spectrum Analysis / methods

Substances

Adjuvants, Immunologic
Influenza Vaccines
Saponins
Oleanolic Acid