Insecticidal activity of paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Agricultural and Food Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html.[EN] Paraherquamide H (1) and paraherquamide 1 (2), two new compounds of the paraherquamide (PHQ) family, together with the already known paraherquamide A (3), paraherquamide B (4), paraherquamide E (5), VM55596 (N-oxide paraherquamide) (6), paraherquamide VM55597 (7), and five known diketopiperazines (8-12) have been isolated from the culture broth of Penicillium cluniae Quintanilla. The structure of 1 and 2, on the basis of NMR and MS analysis, was established. It is worth noticing that, in both cases, an unusual oxidative substitution in C-16 was found, which had only previously been detected in PHQ 7. Isolated compounds were tested for insecticidal activity against the hemipteran Oncopeltus fasciatus Dallas. Mortality data have allowed preliminary structure activity relationships to be proposed. The most potent product was 5 with a LD50 of 0.089,mu g/nymph.The authors acknowledge the Conselleria de Educación y Ciencia de la C. Valenciana for the doctoral grant to M. P. L, the Fundación José y Ana Royo, the Comisión Interministerial de Ciencia y Tecnología (CICYT) and the Conselleria de Agricultura, P. y A. de la C. Valenciana, for financial supportLópez-Gresa, MP.; Gonzalez Más, MC.; Ciavatta, ML.; Ayala Mingol, I.; Moya, P.; Primo, J. (2006). Insecticidal activity of paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae. Journal of Agricultural and Food Chemistry. 54(8):2921-2925. https://doi.org/10.1021/jf0530998S2921292554