Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
J Agric Food Chem. 2013 Feb 27;61(8):1779-83. doi: 10.1021/jf304933z. Epub 2013 Feb 13.
Agropyrenol is a phytotoxic substituted salicylic aldehyde produced in liquid culture by Ascochyta agropyrina var. nana , a potential mycoherbicide proposed for the control of the perennial weed Elytrigia repens. In this study, six derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on non-host weedy and agrarian plants, fungi, Gram-positive and Gram-negative bacteria, and brine shrimp larvae. The results provide insights into the structure-activity relationships of agropyrenol. Both the double bond and the diol system of the 3,4-dihydroxypentenyl side chain as well as the aldehyde group at C-1 of the phenolic ring of agropyrenol proved to be important for the phytotoxicity. The lesser polar 3',4'-O,O'-isopropylidene of agropyrenol also showed significant zootoxic and slight antimicrobial activities. This finding could be useful in devising new natural herbicides for practical application in agriculture.
阿格罗皮伦醇是一种植物毒性取代水杨酸醛，由小长喙壳菌变种小长喙壳菌在液体培养中产生，是一种潜在的用于控制多年生杂草节节麦的生防菌。在这项研究中，对该毒素的 6 种化学修饰衍生物进行了植物毒性、抗微生物和动物毒性活性测定，并研究了结构-活性关系。每种化合物都在非宿主杂草和农田植物、真菌、革兰氏阳性菌和革兰氏阴性菌以及卤虫幼虫上进行了测试。结果为阿格罗皮伦醇的结构-活性关系提供了新的见解。阿格罗皮伦醇中 3,4-二羟基戊烯基侧链的双键和二醇系统以及酚环 C-1 上的醛基都被证明对植物毒性很重要。阿格罗皮伦醇的较小极性 3',4'-O,O'-亚异丙基也显示出显著的动物毒性和轻微的抗微生物活性。这一发现可能有助于设计新的天然除草剂，以便在农业中实际应用。
