López-Gresa M Pilar, González M Carmen, Ciavatta Letizia, Ayala Ildefonso, Moya Pilar, Primo Jaime
Centro de Ecología Química Agrícola, Universidad Politécnica de Valencia, Campus de Vera, Edificio 9B, Laboratorio 111, 46022 Valencia, Spain.
J Agric Food Chem. 2006 Apr 19;54(8):2921-5. doi: 10.1021/jf0530998.
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.
对羟基赫曲霉素H（1）和对羟基赫曲霉素I（2）是对羟基赫曲霉素（PHQ）家族的两种新化合物，它们与已知的对羟基赫曲霉素A（3）、对羟基赫曲霉素B（4）、对羟基赫曲霉素E（5）、VM55596（对羟基赫曲霉素N-氧化物）（6）、对羟基赫曲霉素VM55597（7）以及五种已知的二酮哌嗪（8 - 12）一起，从克卢尼青霉（Penicillium cluniae Quintanilla）的培养液中分离得到。基于核磁共振（NMR）和质谱（MS）分析确定了1和2的结构。值得注意的是，在这两种情况下，均发现C-16位存在不寻常的氧化取代，这种情况此前仅在对羟基赫曲霉素7中检测到。对分离得到的化合物针对半翅目昆虫红蝽（Oncopeltus fasciatus Dallas）进行了杀虫活性测试。死亡率数据有助于提出初步的构效关系。最有效的产物是5，其半数致死剂量（LD50）为0.089微克/若虫。
