Journal
TETRAHEDRON
Volume 68, Issue 1, Pages 106-113Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.10.080
Keywords
Juvenile hormone; Structure-activity relationship; Juvenilizing effect; Heteropteran insect
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Funding
- Japan Society for the Promotion of Science (JSPS) [20380038, 23108523]
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- Japan Science and Technology Agency (JST) [AS231Z03024E]
- Grants-in-Aid for Scientific Research [20380038] Funding Source: KAKEN
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The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.
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