A comprehensive review of glycosylated bacterial natural products

Abstract

A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.

Naquihexcin A, a S-Bridged Pyranonaphthoquinone Dimer Bearing an Unsaturated Hexuronic Acid Moiety from a Sponge-Derived Streptomyces sp. HDN-10-293

“…10,11 Compound 3 showed cytotoxicity against NB4 and HL-60 cells (IC 50 values: 1.7 and 1.8 μM, respectively), while 1 could inhibit the proliferation of an adriamycin resistant human breast cancer cell line MCF-7 ADM with IC 50 = 16.1 μM (adriamycin as positive control, IC 50 > 20.0 μM).…”

A chemocentric view of the natural product inventory

“…Thorson and colleagues 6 have recently noted 344 distinct sugar building blocks that are attached to polyketides, quinones, coumarins, enediynes, indoles and macrolides, including the spinosyn and thiazole peptide classes noted below. Glycosylation enzymes can build N-glycosides, O-glycosides, S-glycosides and C-glycosides.…”

Biosynthesis of amino deoxy-sugar-conjugated flavonol glycosides by engineered Escherichia coli

“…Moreover, the amino sugars are also part of the structures of proteins and lipids in cells and are involved in energy metabolism, the generation of biosynthetic resources, the maintenance of structural integrity, and cellular pathogenesis [2]. Unlike microbial secondary metabolites [3], plant-derived natural products contain simple sugars, such as D-glucose, d-galactose, Dglucuronic acid, L-rhamnose, D-xylose, and D-arabinose. However, few plant-derived molecules are found conjugated with simple amino sugars, like d-N-acetyl glucosamine, D-glucosamine, and d-4-deoxy-4-formaido-L-arabinose [4].…”