Andolfi Anna, Maddau Lucia, Cimmino Alessio, Linaldeddu Benedetto T, Basso Sara, Deidda Antonio, Serra Salvatorica, Evidente Antonio
Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. 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.
Phytochemistry. 2014 Jul;103:145-153. doi: 10.1016/j.phytochem.2014.03.016. Epub 2014 Apr 23.
In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A-C and 16-O-acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A-C were established by spectroscopic methods as (1R*,2R*,3'S*,4'R*,5'R*)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, (1R*,2R*,3'S*,4'R*,5'R*,10'R*,12'R*,13'R*,14'S*) and (1R*,2R*,3'S*,4'R*,5'R*,10'S*,12'R*,13'R*,14'S*)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2-yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5). The structures of 16-O-acetylbotryosphaerilactones A and C were determined by comparison of their spectral data with those of the corresponding acetyl derivatives obtained by acetylation of botryosphaerilactone A. The metabolites isolated, except 4 and 5, were tested at 1mg/mL on leaves of grapevine cv. Cannonau and cork oak using the leaf puncture assay. They were also tested on detached grapevine leaves at 0.5mg/mL and tomato cuttings at 0.1mg/mL. In all phytotoxic assays only jasmonic acid was found to be active. All metabolites were inactive in the zootoxic assay at 50 μg/mL.
在本研究中，对从表现出楔形溃疡的衰退葡萄植株中分离出的一种尚未正式描述的葡萄座腔菌属菌株（BL 101）进行了研究，以考察其体外产生生物活性次生代谢产物的能力。从该菌株的培养滤液中分离出三种茉莉酸酯，命名为葡萄座腔茉莉酸酯A - C以及16 - O - 乙酰基葡萄座腔菌素A和C，同时还分离出了（1R,2R）-茉莉酸、其甲酯、葡萄座腔菌素A、（3S,4R,5R）-4 - 羟甲基 - 3,5 - 二甲基二氢 - 2 - 呋喃酮和（3R,4S）-葡萄座腔菌素。通过光谱方法确定葡萄座腔茉莉酸酯A - C的结构分别为（1R*,2R*,3'S*,4'R*,5'R*）-4 - 羟甲基 - 3,5 - 二甲基二氢 - 2 - 呋喃酮、（1R*,2R*,3'S*,4'R*,5'R*,10'R*,12'R*,13'R*,14'S*）和（1R*,2R*,3'S*,4'R*,5'R*,10'S*,12'R*,13'R*,14'S*）-4 - （4 - 羟甲基 - 3,5 - 二甲基四氢 - 呋喃 - 2 - 基氧甲基）-3,5 - 二甲基二氢 - 2 - 呋喃酮茉莉酸酯（1、4和5）。通过将16 - O - 乙酰基葡萄座腔菌素A和C的光谱数据与葡萄座腔菌素A乙酰化得到的相应乙酰衍生物的光谱数据进行比较，确定了它们的结构。除4和5外，分离得到的代谢产物以1mg/mL的浓度在葡萄品种卡诺娜和栓皮栎的叶片上采用叶穿刺试验进行测试。它们还以0.5mg/mL的浓度在离体葡萄叶片上以及以0.1mg/mL的浓度在番茄插条上进行测试。在所有植物毒性试验中，仅发现茉莉酸具有活性。所有代谢产物在50μg/mL的动物毒性试验中均无活性。
