- 6-Gingesulfonic acid, a new anti-ulcer principle, and gingerglycolipids A, B and C, three new monoacyldigalactosylglycerols from Zingiberis rhizoma originating in Taiwan
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By monitoring the effects of HCl/ethanol-induced gastric lesions in rats, a new anti-ulcer principle named 6-gingesulfonic acid was isolated from Zingiberis Rhizoma, the dried rizhome of Zingiber officinale Roscoe (cultivated and processed in Taiwan) toge
- Yoshikawa,Hatakeyama,Taniguchi,Matuda,Yamahara
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- Stomachic principles in ginger. III. An anti-ulcer principle, 6- gingesulfonic acid, and three monoacyldigalactosylglycerols, gingerglycolipids A, B, and C, from Zingiberis Rhizoma originating in Taiwan
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An anti-ulcer constituent, 6-gingesulfonic acid, and three monoacyldigalactosylglycerols, gingerglycolipids A, B, and C, were isolated from Zingiberis Rhizoma, the dried rhizome of Zingiber officinale ROSCOE which was cultivated in Taiwan, together with (+)-angelicoidenol-2-O-β-D- glucopyranoside. Based on chemical reactions and physicochemical evidence, the structures of 6-gingesulfonic acid, gingerglycolipids A, B, and C have been determined. In addition, the absolute stereostructure of (+)- angelicoidenol-2-O-β-D-glucopyranoside was clarified on the basis of its synthesis from d-borneol. 6-Gingesulfonic acid showed weaker pungency and more potent anti-ulcer activity than 6-gingerol and 6-shogaol.
- Yoshikawa,Yamaguchi,Kunimi,Matsuda,Okuno,Yamahara,Murakami
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- First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry
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Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls - a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.
- Adamo, Mauro F. A.,Bencivenni, Grazia,Gillick-Healy, Malachi W.,Kelly, Brian G.,Moccia, Maria,Ravelli, Andrea
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p. 1091 - 1094
(2020/02/22)
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