Sharma Amit Raj, Harunari Enjuro, Oku Naoya, Matsuura Nobuyasu, Trianto Agus, Igarashi Yasuhiro
Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.
Okayama University of Science, 1-1 Ridaicho, Okayama 700-0005, Japan.
Beilstein J Org Chem. 2020 Mar 2;16:297-304. doi: 10.3762/bjoc.16.29. eCollection 2020.
A pair of geometrically isomeric unsaturated keto fatty acids, (6,8)- and (6,8)-5-oxo-6,8-tetradecadienoic acids ( and ), were isolated from the culture broth of an actinomycete of the genus , which was associated with a stony coral, sp. Their chemical structures were elucidated by spectroscopic analysis including NMR and MS, with special assistance of spin system simulation studies for the assignment of an geometry at C8 in . As metabolites of microbes, compounds and are unprecedented in terms of bearing a 2,4-dienone system. Both and showed antibacterial activity against the plant pathogen and the fish pathogen , with a contrasting preference that is more effective to the former strain while is so to the latter. In addition, compounds and displayed agonistic activity against peroxisome proliferator-activated receptors (PPARs) with an isoform specificity towards PPARα and PPARγ.
从与石珊瑚（Porites sp.）相关的链霉菌属放线菌的培养液中分离出一对几何异构体不饱和酮脂肪酸，即(6,8)-和(6,8)-5-氧代-6,8-十四碳二烯酸（A和B）。通过包括核磁共振（NMR）和质谱（MS）在内的光谱分析，并借助自旋系统模拟研究来确定A中C8位的构型，从而阐明了它们的化学结构。作为微生物的代谢产物，化合物A和B具有2,4-二烯酮系统，这在以往是前所未有的。化合物A和B均对植物病原菌Xanthomonas campestris和鱼类病原菌Vibrio anguillarum表现出抗菌活性，二者偏好有所不同，A对前者菌株更有效，而B对后者更有效。此外，化合物A和B对过氧化物酶体增殖物激活受体（PPARs）表现出激动活性，且对PPARα和PPARγ具有亚型特异性。
