A series of 16 new chiral nonracemic polyhydroxylated piperidines was synthesized utilizing several chiral beta-amino-alcohols. They act as a nitrogen source, chirality inducer and iminium stabilizer, in the desymmetrization of meso-trihydroxylated glutaraldehyde. The biological activity of these compounds towards several glycosidases (alpha-D-glucosidase, alpha-D-mannosidase, alpha-L-fucosidase) has been evaluated.
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http://dx.doi.org/10.1016/j.bmc.2004.07.039 | DOI Listing |
J Appl Toxicol
October 2024
Toxi-Coop Zrt., Budapest, Hungary.
Mulberry (genus Morus) leaves have long been used as a human food, especially in Asia, and animal feed. More recently, mulberry leaf extracts have been introduced as a convenient way to consume mulberry for non-nutritional functional effects. Reducose® 5% is an Morus alba leaf extract that has been highly purified and standardized to a content of 5 ± 0.
View Article and Find Full Text PDFOrg Biomol Chem
August 2022
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany.
Strategies for synthesizing polyhydroxylated piperidines such as iminosugars have received broad attention. These substances are known to interact with carbohydrate related enzymes, glycosidases and glycosyltransferases, to which also the large enzyme families of chitin synthases and cellulose synthases belong. Many chemical and biological aspects of chitin synthases remain unexplored due to the fact that modulating substances are hardly available or expensive.
View Article and Find Full Text PDFChem Rec
November 2021
School of Biological and Chemical Sciences, NUI Galway, University Road, Galway, H91 TK33, Ireland.
This personal account focuses on synthesis of polyhydroxylated piperidines, a subset of compounds within the iminosugar family. Cyclisations to form the piperidine ring include reductive amination, substitution via amines, iminium ions and cyclic nitrones, transamidification (N-acyl transfer), addition to alkenes, ring contraction and expansion, photoinduced electron transfer, multicomponent Ugi reaction and ring closing metathesis. Enantiomerically pure piperidines are obtained from chiral pool precursors (e.
View Article and Find Full Text PDFCrit Rev Food Sci Nutr
July 2023
Food and Biodynamic Chemistry Laboratory, Tohoku University, Sendai, Japan.
Mulberry leaves are rich in biologically active compounds, including phenolics, polysaccharides, and alkaloids. Mulberry leaf iminosugars (MLIs; a type of polyhydroxylated alkaloids), in particular, have been gaining increasing attention due to their health-promoting effects, including anti-diabetic, anti-obesity, anti-hyperglycemic, anti-hypercholesterolemic, anti-inflammatory, and gut microbiota-modulatory activities. Knowledge regarding the in vivo bioavailability and bioactivity of MLIs are crucial to understand their role and function and human health.
View Article and Find Full Text PDFCarbohydr Res
June 2021
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing, Jiangsu, 210094, PR China. Electronic address:
Polyhydroxylated alkaloids display a wide range of biological activities, suggesting their use in the treatment of various diseases. Their most famous representative, 1-deoxynojirimycin (DNJ), is a natural product that shows α- and β-glucosidase inhibition. This molecule has been since converted into two clinically approved drugs i.
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