Synthesis and Biological Activity of Allosamidin and Allosamidin Analogues

✍ Scribed by Blattner, Regine; Gerard, Philippa J.; Spindler-Barth, Margarethe

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 316 KB
• Volume: 50
• Category: Article
• ISSN: 1526-498X
• DOI: 10.1002/(sici)1096-9063(199708)50:4<312::aid-ps594>3.0.co;2-o

✦ Synopsis

The chitinase inhibitor/insect ecdysis inhibitor allosamidin and eight allosamidin analogues have been synthesised from simple carbohydrate starting materials. Allosamidin was assayed against T ineola bisselliella (Hummel) larvae and all nine compounds were examined for their e †ects on the development of larvae of L ucilia cuprina (Wiedemann). High larval mortality compared to controls resulted when T . bisselliella and L . cuprina larva were exposed to allosamidin. The (1 ] 3) linked regioisomer, the dimeric analogue and the gluco-conÐgurated dimeric analogue of allosamidin all showed high activity against L . cuprina larvae. The regioisomer, the (1 ] 3) linked isomer and its dimeric analogue, as well as the monomer allosamizoline and its regioisomer, were inactive. These new in-vivo results are consistent with known in-vitro insect chitinase inhibition data, in that greatest larval mortality was exhibited by the best inhibitors.