hederagenin

Hederagenin is a pentacyclic triterpenoid sapogenin belonging to the oleanane class. It commonly serves as the aglycone component of a variety of plant saponins, most notably those from Hedera helix (ivy), where it occurs as the non-sugar moiety released by hydrolysis of ivy glycosides such as hederacoside C.

Chemically, hederagenin is the 3β-hydroxy derivative of olean-12-en-28-oic acid, i.e., 3β-hydroxyolean-12-en-28-oic acid. It features a hydroxyl group at C-3, a double bond in the ring system between C-12 and C-13, and a terminal carboxylic acid at C-28.

Occurrence and sources: The best-known natural source is ivy leaves. Hederagenin glycosides are present in ivy and related species, and the aglycone portion is commonly used as a reference compound in the study of plant saponins.

Biosynthesis: In plants, hederagenin derives from the triterpene skeleton produced by squalene via cyclization to β-amyrin, followed by oxidation steps that install the 3β-hydroxyl group and the 28-carboxyl group, yielding the oleanane sapogenin.

Uses and activities: As a sapogenin, hederagenin is the aglycone of numerous saponins with various ecological roles in plants and applications in pharmaceuticals and cosmetics. In vitro studies have reported anti-inflammatory, antimicrobial, and cytotoxic activities for hederagenin and its glycosides; however, clinical efficacy has not been established.