2-Hydroxymethyl-3,4-dihydroxy-6-methyl-pyrrolidine (6-deoxy-DMDP), an alkaloid beta-mannosidase inhibitor from seeds of Angylocalyx pynaertii.
A polyhydroxy alkaloid has been isolated from the seeds of the African legume Angylocalyx pynaertii and identified as a 2-hydroxymethyl-3,4-dihydroxy-5-methylpyrrolidine by ms and 1H- and 13C-nmr spectroscopy. The absolute stereochemistry was established, by a stereochemically unambiguous synthesis from diacetone glucose, as 2,5-imino-1,2,5-trideoxy-D-mannitol, which may also be regarded as 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) [2] in which a hydroxymethyl group is deoxygenated, i.e., 6-deoxy-DMDP [1]. Whereas the structurally related polyhydroxypyrrolidine alkaloids which have previously been discovered are inhibitors of alpha- and beta-glucosidase, 6-deoxy-DMDP is unique in inhibiting beta-mannosidase. In addition to this novel alkaloid and 2-hydroxymethyl-3,4-dihydroxypyrrolidine [3], previously shown to be present in several Angylocalyx species, the known piperidine alkaloids deoxymannojirimycin [4] and fagomine [5] were identified for the first time as constituents of An. pynaertii seeds.
Molyneux
R J
RJ
Western Regional Research Center, USDA, Albany, California 94710.
Pan
Y T
YT
Tropea
J E
JE
Elbein
A D
AD
Lawyer
C H
CH
Hughes
D J
DJ
Fleet
G W
GW
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002163:Cameroon; D007887:Fabaceae / Q000737:chemistry*; D050113:Imino Furanoses; D009682:Magnetic Resonance Spectroscopy; D008353:Mannitol / Q000031:analogs & derivatives; D008361:Mannosidases / Q000037:antagonists & inhibitors*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010946:Plants, Medicinal; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D012639:Seeds / Q000737:chemistry*; D044902:beta-Mannosidase
D000470:Alkaloids; D050113:Imino Furanoses; D011759:Pyrrolidines; D008353:Mannitol; C043121:2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine; D008361:Mannosidases; D044902:beta-Mannosidase