Goldmann A, Message B, Tepfer D, Molyneux R J, Duclos O, Boyer F D, Pan Y T, Elbein A D
Laboratoire de Biologie de la Rhizosphère, Institut National de la Recherche Agronomique, Versailles, France.
J Nat Prod. 1996 Dec;59(12):1137-42. doi: 10.1021/np960409v.
Calystegines, polyhydroxy nortropane alkaloids, are a recently discovered group of plant secondary metabolites believed to influence rhizosphere ecology as nutritional sources for soil microorganisms and as glycosidase inhibitors. Evidence is presented that calystegines mediate nutritional relationships under natural conditions and that their biological activities are closely correlated with their chemical structures and stereochemistry. Assays using synthetic (+)- and (-)-enantiomers of calystegine B2 established that catabolism by Rhizobium meliloti, glycosidase inhibition, and allelopathic activities were uniquely associated with the natural, (+)-enantiomer. Furthermore, the N-methyl derivative of calystegine B2 was not catabolized by R. meliloti, and it inhibited alpha-galactosidase, but not beta-glucosidase, whereas the parent alkaloid inhibits both enzymes. This N-methyl analog therefore could serve to construct a cellular or animal model for Fabry's disease, which is caused by a lack of alpha-galactosidase activity.
旋花茄碱是一类多羟基降托烷生物碱，是最近发现的一组植物次生代谢产物，被认为作为土壤微生物的营养来源和糖苷酶抑制剂影响根际生态。有证据表明，旋花茄碱在自然条件下介导营养关系，且它们的生物活性与其化学结构和立体化学密切相关。使用旋花茄碱B2的合成（+）-和（-）-对映体进行的测定表明，苜蓿根瘤菌的分解代谢、糖苷酶抑制和化感活性与天然的（+）-对映体独特相关。此外，旋花茄碱B2的N-甲基衍生物不能被苜蓿根瘤菌分解代谢，它抑制α-半乳糖苷酶，但不抑制β-葡萄糖苷酶，而母体生物碱则抑制这两种酶。因此，这种N-甲基类似物可用于构建由α-半乳糖苷酶活性缺乏引起的法布里病的细胞或动物模型。
