Trehazolin, a new trehalase inhibitor.

Abstract

During the course of screening for inhibitors of trehalase, we found the pseudodisaccharide termed trehazolin1 (1) in a culture broth of Micromonospora, strain SANK 62390n. This paper describes the isolation, structure determination, and inhibitory activity of trehazolin. One loopful of the producing organism was aseptically transferred from an agar slant into baffled 500-ml Erlenmeyer flasks each containing 80ml of a primary seed medium.This mediumwas composed of glucose 1%, glycerol 1%, oatmeal 0.5%, sucrose 1%, soybean meal 2%, Casamino acids 0.5%, pressed yeast 1%, CaCO3 0.1%, and Disfoam CB-442 (Nippon Yushi Co.) 0.01%. After formulation, the pH was adjusted to 7.0 with aq NaOH, and the mediumwas sterilized. The incubation was performed on a rotary shaker at 220rpmat 28°C for 216 hours. Forty ml of the primary seed culture were aseptically transferred into baffled 2-liter Erlenmeyer flasks each containing 800ml of a secondary seed/production medium which was composed of glucose 2%, soluble starch 1 %, pressed yeast 0.9%, meat extract 0.5%, Polypepton 0.5%, NaCl 0.5%, CaCO3 0.3%, and Disfoam CB-442 0.01%. The medium was then adjusted to pH 7.2

A Review of the Applications of Chitin and Its Derivatives in Agriculture to Modify Plant-Microbial Interactions and Improve Crop Yields

“…Therefore, a number of synthetic structural analogues have been developed [147,152]. Trehazolin was initially isolated from a strain of Micromonospora bacteria [153], in which it is an active antibiotic. As a result, it is now thought that an increased understanding of plant-Micromonospora interactions could produce further biological control agents against pests and pathogens [154].…”

The toxic and lethal effects of the trehalase inhibitor trehazolin in locusts are caused by hypoglycaemia

“…It was discovered and isolated as a product of the actinomycete Micromonospora by Ando et al (1991). Trehazolin has antifungal as well as insecticidal activity but does not affect mice when injected at a dose of 100 mg kg -1 (Ando et al, 1995a).…”

Synthesis of trehazolin .BETA.-anomer.

“…Evaluation of compound (3) reveals that the stereochemistry of the anomeric position is significant for generation of inhibitory activities towards trehalases. 243 Trehazolin (1), reported by Ando and co-workers in 1991, is a unique natural pseudodisaccharide isolated from culture broths of Micromonospora SANK62390 and Amicolatopsis SANK60791. It exhibits strong specific activities towards various trehalases1}.…”