Kozachok_2019_Phytochemistry_169_112162

Twelve undescribed triterpenoid pentacyclic glycosides, medicagenic acid (3-O-beta-D-glucuronopyranosyl-28-O-{[beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamn opyranosyl-(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyran osyl-(1-->)}-2beta,3beta-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-beta-D-glucuronopyranosyl-28-O-{[alpha-L-rhamnopyranosyl-(1-->2)]-[beta-D-api ofuranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyranosyl-(1-->)}-2beta,3beta-dihydroxy olean-12-ene-23,28-dioic acid, 3-O-beta-D-glucuronopyranosyl-28-O-{[alpha-L-rhamnopyranosyl-(1-->2)]-3,4-O-diace tyl-beta-D-fucopyranosyl-(1-->)}-2beta,3beta-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-beta-D-glucopyranosyl-(1-->2)]-[2-O-acetyl-alpha-L-rhamnopyrano syl-(1-->4)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->)}-2beta,3b eta-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-beta-D-glucopyranosyl-(1-->2)]-[3-O-acetyl-alpha-L-rhamnopyrano syl-(1-->4)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->)}-2beta,3b eta-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-beta-D-glucopyranosyl-(1-->2)]-[4-O-acetyl-alpha-L-rhamnopyrano syl-(1-->4)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->)}-2beta,3b eta-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->6)]- beta-D-glucopyranosyl-(1-->)}-2beta,3beta-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->6)]-beta-D-gluc opyranosyl-(1-->)}-2beta,3beta-dihydroxyolean-12-ene-23,28-dioic acid), zanhic acid (3-O-beta-D-glucuronopyranosyl-28-O-{[beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamn opyranosyl-(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyran osyl-(1-->)}2beta,3beta,16alpha-trihydroxyolean-12-ene-23,28-dioic acid, 3-O-beta-D-glucuronopyranosyl-28-O-{[beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamno pyranosyl-(1-->2)]-beta-D-fucopyranosyl-(1-->)}-2beta,3beta,16alpha-trihydroxyole an-12-ene-23,28-dioic acid), 29-hydroxy-medicagenic acid (3-O-beta-D-glucuronopyranosyl-28-O-{[beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamn opyranosyl-(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyran osyl-(1-->)}-2beta,3beta,29beta-trihydroxyolean-12-ene-23,28-dioic acid) and herniaric acid (28-O-{[6-O-acetyl-beta-D-glucopyranosyl-(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->4 )-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->)}-2beta,3beta-dihydr oxyolean-18-ene-23,28-dioic acid) were isolated from the whole plant extract of Herniaria glabra L. (Caryophyllaceae), wild growing in the Ukraine. In addition, five known triterpenoid saponins; i.e. herniariasaponins 1, 4, 5, 6, and 7 were also isolated. Their structures were elucidated by HRESIMS, 1D and 2D NMR spectroscopy, as well as by comparison with the literature data. Twelve herniariasaponins, the purified crude extract, and the saponin fraction were evaluated in vitro for their xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity. Moreover, herniariasaponins 4, 5, and 7 were screened for their cholinesterase inhibitory potential. As a result, no or low inhibition towards the mentioned enzymes was observed.