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.

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-beta-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-beta-D-glucopyranoside was clarified on the basis of its synthesis from d-borneol. 6-Ginesulfonic acid showed weaker pungency and more potent anti-ulcer activity than 6-gingerol and 6-shogaol.