Studies on the constituents of Broussonetia species. VII. Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, as inhibitors of glycosidase, from Broussonetia kazinoki SIEB.
Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, were isolated from the branches of Broussonetia kazinoki SIEB, (Moraceae). Broussonetines M, O, P, and Q were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(10S)-10,13-dihydroxy-tri decyl]pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)9-oxo-13-hydroxy-3- tridecenyl]pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)10-oxo-13-hydroxy-3-++ +tridecenyl]pyrrolidine (3), and (2R,3S,4R,5R)-2-hydroxymethyl-3-hydroxy-4-(beta-D-glucopyranosyloxy++ +)-5-[10-oxo-13-(beta-D-glucopyranosyloxy)tridecyl]pyrrolidine (4) respectively, by spectroscopic and chemical methods. 1-4 inhibited beta-glucosidase, beta-galactosidase and beta-mannosidase.
Shibano
M
M
Osaka University of Pharmaceutical Sciences, Takatsuki, Japan.
Tsukamoto
D
D
Fujimoto
R
R
Masui
Y
Y
Sugimoto
H
H
Kusano
G
G
D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D004791:Enzyme Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008361:Mannosidases / Q000037:antagonists & inhibitors; D013058:Mass Spectrometry; D010946:Plants, Medicinal / Q000737:chemistry*; D011759:Pyrrolidines / Q000302:isolation & purification* / Q000494:pharmacology; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors; D044902:beta-Mannosidase
D000470:Alkaloids; D004791:Enzyme Inhibitors; D011759:Pyrrolidines; D006026:Glycoside Hydrolases; D008361:Mannosidases; D001617:beta-Glucosidase; D001616:beta-Galactosidase; D044902:beta-Mannosidase