Diplobifuranylones A and B, 5′-monosubstituted tetrahydro-2H-bifuranyl-5-ones produced by Diplodia corticola, a fungus pathogen of cork oak
Diplobifuranylones A and B, 5′-monosubstituted tetrahydro-2H-bifuranyl-5-ones produced by Diplodia corticola, a fungus pathogen of cork oak
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DOI：
10.1021/np050393l
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发表时间：
2006-04-01
影响因子：
5.1
通讯作者：
Motta, A
中科院分区：
文献类型：
--
作者：
Evidente, A;Andolfi, A;Motta, A
从软木栎（Quercus suber）溃疡病菌Diplodia corticola的培养滤液中分离得到两种新的5'-单取代四氢-2H -联呋喃基-5 -酮，分别命名为双联呋喃酮A和B（1和2）。同一真菌还产生了八种已知代谢物，即双联吡喃酮、(3S, 4R)-反式-和(3R, 4R)-顺式-4 -羟基蜜环菌醇、沙皮呋喃酮B及其(S,S)-对映体，以及球壳菌素A - C。利用光谱和化学方法，将双联呋喃酮A和B（1和2）鉴定为两种非对映异构的5'-(1 -羟乙基)-3,4,2',5'-四氢-2H -[2,2']联呋喃基-5 -酮。通过NOESY和ROESY实验推断出这两种代谢物（1和2）的相对立体化学结构，应用Mosher法确定C - 5'位羟乙基侧链手性碳的绝对立体化学结构，结果表明在1和2中分别为S和R。在非寄主植物上进行测定时，双联呋喃酮A和B未显示出植物毒性活性。在卤虫（Artemia salina）幼虫致死性生物测定中，在最高测试浓度（300μg/mL）下，1和2均无毒性。
Two new 5'-monosubstituted tetrahydro-2H-bifuranyl-5-ones, named diplobifuranylones A and B ( 1 and 2), were isolated from the culture filtrates of Diplodia corticola, the causal agent of a canker of cork oak ( Quercus suber). The same fungus also produced eight known metabolites, namely, the diplopyrone, (3S, 4R)-trans- and (3R, 4R)-cis-4-hydroxymellein, sapinofuranone B and its ( S,S)-enantiomer, and sphaeropsidins A-C. Diplobifuranylones A and B ( 1 and 2) were characterized, using spectroscopic and chemical methods, as two diastereomeric 5'-(1-hydroxyethyl)-3,4,2',5'-tetrahydro-2H-[ 2,2'] bifuranyl-5-ones. While the relative stereochemistry of the two metabolites ( 1 and 2) was deduced by NOESY and ROESY experiments, the absolute stereochemistry of the chiral carbon of the hydroxyethyl side chain at C-5', determined by application of Mosher's method, proved to be S and R in 1 and 2, respectively. Assayed on a nonhost plant, diplobifuranylones A and B did not show phytotoxic activity. In an Artemia salina larvae lethality bioassay neither 1 nor 2 was toxic at the highest concentration tested ( 300 mu g/mL).