Saponin and Sapogenol. XLV. : Structures of Kaikasaponins I, II, and III from Sophorae Flos, the Buds of Sophora japonica L.

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Abstract
Three new glucuronide-saponins, named kaikasaponin I (7), kaikasaponin II (8), and kaikasaponin III (9), were isolated from Sophorae Flos, the buds of Sophora japonica L. (Leguminosae), together with five known glucuronide-saponins soyasaponin I (6), soyasaponin III (4), azukisaponin I (2), azukisaponin (II) 3, and azukisaponin V (5). By use of the photochemical degradation method, which is one of selective cleavage-methods for the glucuronide linkage in glucuronide-saponins, and on the basis of chemical and spectral evidence, the structures of kaikasaponins I, II, and III have been determined as 3-O-[.beta.-D-galactopyranosyl-(1 .fwdarw. 2)-.beta.-D-glucuronopyranosyl]sophoradiol (7), 3-O-[.alpha.-rhamnopyranosyl-(1 .fwdarw. 2)-.beta.-D-glucuronosyl-(1 .fwdarw. 2)-.beta.-D-glucuronopyranosyl]sophoradiol (8), and 3-O-[.alpha.-L-rhamnopyranosyl-(1 .fwdarw. 2)-.beta.-D-galactopyranosyl-(1 .fwdarw. 2)-.beta.-D-glucuronopyranosyl]sophoradiol (9), respectively. In the course of 13C nuclear magnetic resonance spectral analysis of these kaikasaponins, it has been noticed that some chemical shifts of carbohydrate carbons close to the sapogenol are affected by the presence of a hydroxyl group in the sapogenol nearby the glucuronide linkage.

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