INSECTICIDAL PROPERTIES OF SOME DERIVATIVES OF L-CANAVANINE

Citation
Ga. Rosenthal et al., INSECTICIDAL PROPERTIES OF SOME DERIVATIVES OF L-CANAVANINE, Journal of agricultural and food chemistry, 43(10), 1995, pp. 2728-2734
Citations number
20
Categorie Soggetti
Food Science & Tenology",Agriculture,"Chemistry Applied
ISSN journal
00218561
Volume
43
Issue
10
Year of publication
1995
Pages
2728 - 2734
Database
ISI
SICI code
0021-8561(1995)43:10<2728:IPOSDO>2.0.ZU;2-#
Abstract
The canavanine derivatives D-canavanine and L-homocanavanine as well a s the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobac co hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did no t increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability t o cause larval edema, but the D-enantiomer had little ability to elici t the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant p rotein production. The 1-methyl and 1-ethyl esters of L-canavanine wer e synthesized to determine if enhancing canavanine's hydrophobicity mi ght increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larva l growth more than did the methyl analogue.