title: Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala.
abstract: Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11alpha,12alpha-epoxy-3beta-[(O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl)-oxy]olean-28,13-olide (2), and 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells.
authors.affiliation: Laboratory of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Minpei
authors.initials: M
authors.lastname: Kuroda
authors.forename: Taku
authors.initials: T
authors.lastname: Aoshima
authors.forename: Mitsue
authors.initials: M
authors.lastname: Haraguchi
authors.forename: Maria Claudia Marx
authors.initials: MC
authors.lastname: Young
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Mimaki
mesh_terms: D027703:Amaranthaceae / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D002294:Carcinoma, Squamous Cell; D004354:Drug Screening Assays, Antitumor; D005960:Glucosides; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014315:Triterpenes
chemical_list: C516749:11alpha,12alpha-epoxy-3beta-((O-beta-D-galactopyranosyl-(1-3)-O-(beta-D-glucopyranosyl-(1-2))-beta-D-glucuronopyranosyl)-oxy)olean-28,13-olide; C516750:11alpha,12alpha-epoxy-3beta-((O-beta-D-glucuronopyranosyl)oxy)olean-28,13-olide; C516747:11alpha,12alpha-epoxy-3beta-((O-beta-D-glucuronopyranosyl)oxy)taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester; D000972:Antineoplastic Agents, Phytogenic; D005960:Glucosides; D006027:Glycosides; D014315:Triterpenes; C413246:oleanane; D009828:Oleanolic Acid