Molyneux R J, Pan Y T, Tropea J E, Elbein A D, Lawyer C H, Hughes D J, Fleet G W
Western Regional Research Center, USDA, Albany, California 94710.
J Nat Prod. 1993 Aug;56(8):1356-64. doi: 10.1021/np50098a020.
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.
从非洲豆科植物安吉利卡利克斯·皮纳尔蒂的种子中分离出一种多羟基生物碱，通过质谱以及1H-和13C-核磁共振光谱鉴定为2-羟甲基-3,4-二羟基-5-甲基吡咯烷。通过由双丙酮葡萄糖进行的立体化学明确的合成确定其绝对立体化学结构为2,5-亚氨基-1,2,5-三脱氧-D-甘露糖醇，其也可被视为2R,5R-二羟甲基-3R,4R-二羟基吡咯烷（DMDP）[2]，其中一个羟甲基被脱氧，即6-脱氧-DMDP [1]。先前发现的结构相关的多羟基吡咯烷生物碱是α-和β-葡萄糖苷酶的抑制剂，而6-脱氧-DMDP在抑制β-甘露糖苷酶方面具有独特性。除了这种新型生物碱和先前已证明存在于几种安吉利卡利克斯物种中的2-羟甲基-3,4-二羟基吡咯烷[3]之外，已知的哌啶生物碱脱氧甘露基吉里霉素[4]和法戈明[5]首次被鉴定为安吉利卡利克斯·皮纳尔蒂种子的成分。
