title: (6R,9S)-6"-(4"-hydroxybenzoyl)-roseoside, a new megastigmane derivative from Ouratea polyantha and its effect on hepatic glucose-6-phosphatase.
abstract: A new megastigmane derivative, (6R,9S)-6'-(4"-hydroxybenzoyl)-roseoside (1) and two known compounds, the biflavoneagathisflavone (2) and 4-hydroxybenzoic acid (3) were isolated and purified from leaves and stems of Ouratea polyantha Engl. Agathisflavone was isolated in a single high-speed countercurrent chromatography run, while the megastigmane was purified in two steps, by using a combination of high-speed countercurrent chromatography and analytical column chromatography. All structures were elucidated on the basis of spectral evidence and comparison with literature data. Compound 1 was characterized by [alpha]D20, UV-Vis, IR, MS, 1H NMR, 13C NMR, HMQC, HMBC, COSY and NOESY. Compounds 1 and 2 showed an inhibitory effect of 63.6 and 13.7% on the G-6-Pase intact microsomes, respectively.
authors.affiliation: Laboratorio de Productos Naturales, Escuela de Quimica, Facultad de Ciencias, Universidad Central de Venezuela, Apartado Postal 47102, Caracas, Venezuela.
authors.forename: Jairo
authors.initials: J
authors.lastname: Bermúdez
authors.forename: María
authors.initials: M
authors.lastname: Rodríguez
authors.forename: Masahisa
authors.initials: M
authors.lastname: Hasegawa
authors.forename: Freddy
authors.initials: F
authors.lastname: González-Mujica
authors.forename: Sandra
authors.initials: S
authors.lastname: Duque
authors.forename: Yoichiro
authors.initials: Y
authors.lastname: Ito
mesh_terms: D000818:Animals; D044946:Biflavonoids / Q000737:chemistry; D005952:Glucose-6-Phosphatase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000201:enzymology; D015394:Molecular Structure; D045792:Norisoprenoids / Q000737:chemistry* / Q000494:pharmacology*; D043842:Ochnaceae / Q000737:chemistry*; D010226:Parabens / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems; D051381:Rats; D017207:Rats, Sprague-Dawley
chemical_list: C575396:(6R,9S)-6''-(4''-hydroxybenzoyl)-roseoside; D044946:Biflavonoids; D045792:Norisoprenoids; D010226:Parabens; C079168:agathisflavone; D005952:Glucose-6-Phosphatase; C038193:4-hydroxybenzoic acid