ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal.
Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand.
Mar Drugs. 2023 Jun 2;21(6):344. doi: 10.3390/md21060344.
Five undescribed pentaketide derivatives, ()-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1-2-benzopyran-1-one (), [(3,4)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1-isochromen-3-yl]methyl acetate (), ()-5, 7-dimethoxy-3-((-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3)-one (), ()-7-hydroxy-3-(()-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3)-one (), and a -hydroxyphenyl-2-pyridone derivative, avellaneanone (), were isolated together with the previously reported ()-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3)-one (), ()-7-hydroxy-3-(()-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3)-one () and isosclerone (), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, KUFA0732. The structures of the undescribed compounds were elucidated using 1D and 2D NMR, as well as high-resolution mass spectral analyses. The absolute configurations of the stereogenic carbons in , , , and were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in were determined by ROESY correlations and on the basis of their common biosynthetic origin with . The crude fungal extract and the isolated compounds , , , , and were assayed for their growth inhibitory activity against various plant pathogenic fungi viz. , , , , , , , , and .
从海洋海绵来源真菌 KUFA0732 的乙酸乙酯提取物中分离得到了五个未描述的 pentaketide 衍生物：()-6,8-二羟基-4,5-二甲基-3-亚甲基-3,4-二氢-1-2-苯并吡喃-1-酮（）、[(3,4)-3,8-二羟基-6-甲氧基-4,5-二甲基-1-氧代-3,4-二氢-1-异苯并呋喃-3-基]甲基乙酸酯（）、()-5,7-二甲氧基-3-((-(1-羟乙基)-3,4-二甲基异苯并呋喃-1(3)-酮（）、()-7-羟基-3-((()-1-羟乙基)-5-甲氧基-3,4-二甲基异苯并呋喃 1(3)-酮（）和一个-α-羟基苯基-2-吡啶酮衍生物，阿维兰酮（），以及先前报道的()-3-乙酰基-7-羟基-5-甲氧基-3,4-二甲基异苯并呋喃-1(3)-酮（）、()-7-羟基-3-((()-1-羟乙基)-5-甲氧基-3,4-二甲基异苯并呋喃-1(3)-酮（）和异色酮（）。使用 1D 和 2D NMR 以及高分辨率质谱分析阐明了未知化合物的结构。通过 X 射线晶体学分析确定了立体碳原子在 、 、 和 中的绝对构型。通过 ROESY 相关和基于它们与 共同的生物合成起源，确定了 中 C-3 和 C-4 的绝对构型。粗真菌提取物和分离得到的化合物 、 、 、 、 和 被测试对各种植物病原真菌的生长抑制活性，如 、 、 、 、 、 、 、 。
