Dipartimento di Scienze Chimiche, Università di Napoli Federico II , Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
Dipartimento di Agraria, Sezione di Patologia Vegetale ed Entomologia, Università degli Studi di Sassari , Viale Italia 39, 07100 Sassari, Italy.
J Agric Food Chem. 2016 Jan 13;64(1):217-25. doi: 10.1021/acs.jafc.5b05170. Epub 2015 Dec 30.
Three new lactones and a new fatty acid ester, named sapinofuranones C and D, diplopyrone B, and diplobifuranylone C, respectively, were isolated from Diplodia corticola, together with sphaeropsidins A and C, diplopyrone, diplobifuranylones A and B, diplofuranone A, and the (S,S)-enantiomer of sapinofuranone B. Sapinofuranones C and D, diplopyrone B, and diplobifuranylone C were characterized as (5S)-5-((1,S-1,6-dihydroxyhexa-2,4-dienyl)-dihydrofuran-2-one, 4,5-dihydroxy-deca-6,8-dienoic acid methyl ester, (5S)-5-hydroxy-6-(penta-1,3-dienyl)-5,6-dihydro-pyran-2-one, and 5'-((1R)-1-hydroxyethyl)-2',5'-dihydro-2H-[2,2']bifuranyl-5-one by spectroscopic and chemical methods, respectively. The relative configuration of sapinofuranone C was assigned by X-ray diffraction analysis, whereas its absolute configuration was determined by applying the advanced Mosher's method to its 11-O-p-bromobenzoyl derivative. The same method was used to assign the absolute configuration to C-5 of diplopyrone B and to that of the hydroxyethyl of the side chain of diplobifuranylone C, respectively. The metabolites isolated were tested at 1 mg/mL on leaves of cork oak, grapevine cv. 'Cannonau', and tomato using the leaf puncture assay. They were also tested on tomato cuttings at 0.2, 0.1, and 0.05 mg/mL. Each compound was tested for zootoxic activity on Artemia salina L. larvae. The efficacy of sapinofuranone C and diplopyrone B on three plant pathogens, namely, Athelia rolfsii, Fusarium avenaceum, and Phytophthora nicotianae was also evaluated. In all phytotoxic assays only diplopyrone B was found to be active. It also showed strong inhibition on the vegetative growth of A. rolfsii and P. nicotianae. All metabolites were inactive in the assay performed for the zootoxic activity (A. salina) even at the highest concentration used (200 μg/mL). Diplopyrone B showed a promising antioomycete activity for the control of Phytophthora spp. also taking into account the absence of zootoxic activity.
从 Diplodia corticola 中分离得到了三种新的内酯和一种新的脂肪酸酯，分别命名为 sapinofuranones C 和 D、diplopyrone B 和 diplobifuranylone C，以及 sphaeropsidins A 和 C、diplopyrone、diplobifuranylones A 和 B、diplofuranone A 和 sapinofuranone B 的（S，S）对映体。Sapinofuranones C 和 D、diplopyrone B 和 diplobifuranylone C 分别被鉴定为（5S）-5-（（1，S）-1，6-二羟基己-2,4-二烯基）-二氢呋喃-2-酮、4,5-二羟基-癸-6,8-二烯酸甲酯、（5S）-5-羟基-6-（戊-1,3-二烯基）-5,6-二氢-吡喃-2-酮和 5'-（1R）-1-羟基乙基）-2'，5'-二氢-2H-[2,2']双呋喃-5-酮，通过光谱和化学方法。Sapinofuranone C 的相对构型通过 X 射线衍射分析确定，而其绝对构型则通过应用先进的 Mosher 方法确定其 11-O-对溴苯甲酰基衍生物来确定。同样的方法用于分别确定 diplopyrone B 的 C-5 和 diplobifuranylone C 的侧链羟乙基的绝对构型。在叶穿孔试验中，将分离得到的代谢物在每毫升 1 毫克的条件下，在栓皮栎、酿酒葡萄 cv。‘Cannonau’和番茄叶片上进行测试。还在 0.2、0.1 和 0.05 毫克/毫升的浓度下对番茄插条进行了测试。每种化合物均在卤虫 L.幼虫上进行了杀生物活性测试。还评估了 sapinofuranone C 和 diplopyrone B 对三种植物病原体（Athelia rolfsii、Fusarium avenaceum 和 Phytophthora nicotianae）的功效。在所有的植物毒性试验中，只有 diplopyrone B 表现出活性。它还对 A. rolfsii 和 P. nicotianae 的营养生长表现出强烈的抑制作用。所有代谢物在（A. salina）进行的杀生物活性试验（200 μg/mL）中均不活跃，即使在最高浓度下也是如此。Diplopyrone B 对控制 Phytophthora spp. 具有有前景的抗卵菌活性，同时考虑到它没有杀生物活性。
