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双吡喃,一种由地中海双盘菌(栓皮栎的一种真菌病原体)产生的具有植物毒性的六取代吡喃并吡喃。

Biscopyran, a phytotoxic hexasubstituted pyranopyran produced by Biscogniauxia mediterranea, a fungus pathogen of cork oak.

作者信息

Evidente Antonio, Andolfi Anna, Maddau Lucia, Franceschini Antonio, Marras Francesco

机构信息

Dipartimento di Scienze del Suolo, della Pianta e dell'Ambiente, Università di Napoli Federico II, 80055 Portici, Italy.

出版信息

J Nat Prod. 2005 Apr;68(4):568-71. doi: 10.1021/np049621m.

DOI:10.1021/np049621m
PMID:15844950
Abstract

A new phytotoxic hexasubstituted pyranopyran, biscopyran (3), was isolated together with phenylacetic acid (2) and previously isolated 5-methylmellein (1) from the liquid culture filtrates of Biscogniauxiamediterranea, a major fungal pathogen involved in oak decline in Sardinia. Biscopyran was characterized by spectroscopic methods as a new (Z)-2-methoxy-1-[7-((Z)-2-methoxybut-2-enoyl)-3,4,5,6-tetramethyl-2H,7H-pyrano[2,3-b]pyran-2-yl]but-2-en-1-one. Biscopyran assayed at 0.26-0.026 mM concentration range caused epinasty on cork oak cuttings. On a nonhost plant, tomato, biscopyran caused wilting. Phenylacetic acid, assayed at the same concentration, was toxic to Q. suber, while on tomato cuttings it induced internal tissue collapse on the stem.

摘要

从撒丁岛橡树衰退的主要真菌病原体——地中海比斯科尼亚菌的液体培养滤液中,分离出一种新的具有植物毒性的六取代吡喃并吡喃(双吡喃,3),同时还分离出苯乙酸(2)和之前已分离出的5 - 甲基蜜环菌(1)。通过光谱方法鉴定,双吡喃为一种新的(Z)-2 - 甲氧基 - 1 - [7 - ((Z)-2 - 甲氧基丁 - 2 - 烯酰基)-3,4,5,6 - 四甲基 - 2H,7H - 吡喃并[2,3 - b]吡喃 - 2 - 基]丁 - 2 - 烯 - 1 - 酮。双吡喃在0.26 - 0.026 mM浓度范围内对栓皮栎插条造成偏上性生长。在非寄主植物番茄上,双吡喃导致萎蔫。在相同浓度下测定,苯乙酸对栓皮栎有毒,而在番茄插条上,它会导致茎部内部组织塌陷。

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