Biological Activities of the Nortropane Alkaloid, Calystegine B2, and Analogs:  Structure−Function Relationships

• Published in: Journal of natural products (Washington, D.C.) Vol. 59; no. 12; pp. 1137 - 1142
• Main Authors: Goldmann, Arlette, Message, Brigitte, Tepfer, David, Molyneux, Russell J, Duclos, Olivier, Boyer, François-Didier, Pan, Y. T, Elbein, Alan D
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.12.1996; Glendale, AZ American Society of Pharmacognosy
• Subjects: Agronomy. Soil science and plant productions; alcaloide; alcaloides; aleloquimicos; alkaloids; allelochemicals; alpha-Galactosidase - antagonists & inhibitors; Analytical, structural and metabolic biochemistry; Aromatic and heterocyclic compounds; bacteria; Bacteria - drug effects; Bacteria - metabolism; Biochemistry and biology; Biological and medical sciences; calystegia; Chemical and Process Engineering; chemical composition; chemical structure; Chemical, physicochemical, biochemical and biological properties; chemistry; chimie; composicion quimica; composition chimique; convolvulus arvensis; DNA, Bacterial - biosynthesis; Engineering Sciences; enzyme inhibitors; Enzyme Inhibitors - isolation & purification; Enzyme Inhibitors - pharmacology; espectrometria; estructura quimica; flora del suelo; flore du sol; Food engineering; france; francia; Fundamental and applied biological sciences. Psychology; glicosidasas; glycosidase; glycosidases; Glycoside Hydrolases - antagonists & inhibitors; Heterocyclic compounds, pigments; inhibidores de enzimas; inhibiteur d' enzyme; Life Sciences; metabolite; metabolites; metabolitos; Microbiology; Nortropanes - isolation & purification; Nortropanes - pharmacology; Other biological molecules; Physics, chemistry, biochemistry and biology of agricultural and forest soils; Plant Roots - chemistry; Plants, Medicinal - chemistry; Pseudomonas - drug effects; Pseudomonas - growth & development; Pseudomonas - metabolism; quimica; rhizobium meliloti; Seeds - chemistry; Sinorhizobium meliloti - drug effects; Sinorhizobium meliloti - growth & development; Sinorhizobium meliloti - metabolism; soil flora; Soil science; Solanaceous Alkaloids; spectrometrie; spectrometry; structure chimique; Structure-Activity Relationship; substance allelochimique; Enantiomer(+); Seeds; Rhizobium meliloti; Enantioselectivity; Nitrogen heterocycle; Metabolite; Convolvulaceae; Allelochemicals; Alkaloid; Structure activity relation; Dicotyledones; Angiospermae; Bicyclic compound; Bacteria; Polyol; Solanaceae; Secondary metabolism; Elongation; Symbiosis; Root; Enzyme; Germination; Medicago sativa; Allelopathy; Enzyme inhibitor; Leguminosae; Glycosidases; Plant origin; Hydrolases; Spermatophyta; Catabolism; Rhizobiaceae
• ISSN: 0163-3864; 1520-6025
• 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 α-galactosidase, but not β-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 α-galactosidase activity.