Lentiginosine, a dihydroxyindolizidine alkaloid that inhibits amyloglucosidase

1990/02/20 by Irena Pastuszak, Russell J. Molyneux, Lynn F. James +1 · 7 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Medicine · #Alkaloid #Amylase #Biochemistry #Biology #Carbohydrate Chemistry and Synthesis #Chemistry #Enzyme #Glycosylation and Glycoproteins Research #Lysosomal Storage Disorders Research #Pharmacology #Stereochemistry

paper · doi:10.1021/bi00459a032

openalex publication_date 1990/02/20 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

Lentiginosine, a dihydroxyindolizidine alkaloid, was extracted from the leaves of Astragalus lentiginosus with hot methanol and was purified to homogeneity by ion-exchange, thin-layer, and radial chromatography. A second dihydroxyindolizidine, the 2-epimer of lentiginosine, was also purified to apparent homogeneity from these extracts. Gas chromatography of the two isomers (as the TMS derivatives) showed that they were better than 95% pure; lentiginosine eluted at 8.65 min and the 2-epimer at 9.00 min. Both compounds had a molecular ion in their mass spectra of 157, and the NMR spectra demonstrated that both were dihydroxyindolizidines differing in the configuration of the hydroxyl group at carbon 2. Lentiginosine was found to be a reasonably good inhibitor of the fungal alpha-glucosidase, amyloglucosidase (Ki = 1 x 10(-5) M), but it did not inhibit other alpha-glucosidases (i.e., sucrase, maltase, yeast alpha-glucosidase, glucosidase I) nor any other glycosidases. The 2-epimer had no activity against any of the glycosidases tested.

Cited by

• Phytochemicals: The good, the bad and the ugly?
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• Chain-Branched Polyhydroxylated Octahydro- 1H -Indoles as Potential Leads against Lysosomal Storage Diseases. [europepmc]
• Synthesis of New Indolizidine Derivatives from 1-(2-Quinolyl)-2-propen-1-ol. [europepmc]
• The Stereoselective Nitro-Mannich Reaction in the Synthesis of Active Pharmaceutical Ingredients and Other Biologically Active Compounds. [europepmc]
• Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde-First Diastereoselective Syntheses of (-)-1- epi- lentiginosine. [europepmc]
• Alkaloid Glycosidase Inhibitors [europepmc]

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