Avermectin B1a monosaccharide

Detailed Description

Avermectin monosaccharide is an acid degradation product produced by selective hydrolysis of the terminal saccharide unit of avermectin. Avermectin monosaccharide is a potent inhibitor of nematode larval development, but is devoid of paralytic activity. Despite the importance of avermectin as an anthelmintic in animal health, there are few published reports of the biological activity or the levels of avermectin monosaccharide in animals or in the environment.

Avermectin monosaccharide is soluble in ethanol, methanol, DMF and DMSO.

Mechanism of Action

Avermectins can modulate gamma-aminobutyric acid (GABA) chloride channels in vertebrate neurons.

Insect Biology Applications

Electrophysiological findings by injection of E. elegans mRNA into Xenopus laevis oocytes indicated that Avermectins act on glutamate-gated chloride channels in nematodes.

References

Blizzard T, Fisher MH, Mrozik H, Shih TL (1990) Avermectins and Milbemycins. In: Lukacs G, Ohno M. (eds) Recent Progress in the Chemical Synthesis of Antibiotics. Springer, Berlin, Heidelberg

Chabala J.C. et al. (1980) Ivermectin, a new broad-spectrum antiparasitic agent. J. Med. Chem. 23:1134

Chen TS, Inamine ES (1989) Studies on the biosynthesis of Avermectins. Arch Biochem Biophys. 270(2):521-5 PMID 2705778

Egerton JR et al (1979) Avermectins, new family of potent anthelmintic agents: Efficacy of the B1a component. Antimicrob. Agents Chemother. 15(3):372-378 PMID 464563

Ikeda H and Omura S (1997) Avermectin biosynthesis. Chem. Rev. 97(7):2591-2610

Mrozik H. et al (1982) Avermectin aglycones. 47:489

Pivnichny JV, Arison BY, Preiser FA, Shim JSK and Mrozik H (1988) Base-catalyzed isomerization of avermectins. J. Agric. Food Chem 36(4):826-828

Pivnichny JV, Shim JK and Zimmerman LA (1983) Direct determination of avermectins in plasma at nanogram levels by high-performance liquid chromatography. J. Pharm. Sci. 72(12):1447-1450 PMID 6663483