Insecticidal activity of Paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae.
Paraherquamide H (1) and paraherquamide I (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 LD(50) of 0.089 microg/nymph.
López-Gresa
M Pilar
MP
Centro de Ecología Química Agrícola, Universidad Politécnica de Valencia, Campus de Vera, Edificio 9B, Laboratorio 111, 46022 Valencia, Spain.
González
M Carmen
MC
Ciavatta
Letizia
L
Ayala
Ildefonso
I
Moya
Pilar
P
Primo
Jaime
J
D000818:Animals; D006430:Hemiptera; D007212:Indolizines / Q000737:chemistry; D007306:Insecticides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010407:Penicillium / Q000378:metabolism; D013141:Spiro Compounds / Q000737:chemistry
D007212:Indolizines; D007306:Insecticides; D013141:Spiro Compounds; C084045:VM 55596; C063985:paraherquamide