Bioactive Saponins and Glycosides. XIV. Structure Elucidation and Immunological Adjuvant Activity of Novel Protojujubogenin Type Triterpene Bisdesmosides, Protojujubosides A, B, and B₁, from the Seeds of Zizyphus jujuba var. spinosa (Zizyphi Spinosi Semen)

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Following the elucidation of jujubosides A₁ and C and acetyljujuboside B, novel protojujubogenin type triterpene bisdesmosides, protojujubosides A, B, and B₁, were isolated from Zizyphi Spinosi Semen, the seeds of Zizyphus jujuba MILL. var. spinosa HU. The structures of protojujubosides A, B, and B₁ were determined on the basis of chemical and physicochemical evidence, which included the conversion of protojujubosides to known jujubosides using enzymatic hydrolysis. Protojujubosides A and jujubosides A, B, and C were found to show potent immunological adjuvant activity.