Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala.
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.
Kuroda
Minpei
M
Laboratory of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Aoshima
Taku
T
Haraguchi
Mitsue
M
Young
Maria Claudia Marx
MC
Sakagami
Hiroshi
H
Mimaki
Yoshihiro
Y
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
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