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By virtue of the soil bacterial hydrolysis method applied on jegosaponin (the pericarps saponin of Styrax japonica SIEB. et Zuec.), new four acylated derivatives of barringtogenol C have been isolated in addition to 21-O-tigloyl-barringtogenol C (I) and barringtogenol C (II). The newly isolated sapogenols have been elucidated respectively as 21-O-tigloyl-28-O-acetyl-barringtogenol C (VI), 21-O-tigloyl-22-O-acetyl-barringtogenol C (VIII), 28-O-acetyl-barringtogenol C (IX), and 21 (or 22)-O-2'-cis-hexenoy1-22 (or 21)-O-acetyl-barringtogenol C (X) on the basis of chemical and physicochemical evidences. Consequently, it has become evident that the tigloyl function initially found in I is a genuine form and the anhydro-structure (III or V) is excluded from the partial structure of jegosaponin.

Soil Bacterial Hydrolysis leading to Genuine Aglycone. IV. Four Acylated Derivatives of Barringtogenol C from Jegosaponin