Reappraising the structures and distribution of metabolites from black aspergilli containing uncommon 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one systems.
Reappraising the structures and distribution of metabolites from black aspergilli containing uncommon 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one systems.
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DOI：
10.1021/np200454z
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发表时间：
2011-09-23
影响因子：
5.1
通讯作者：
Cichewicz RH
中科院分区：
文献类型：
--
作者：
Henrikson JC;Ellis TK;King JB;Cichewicz RH
迄今为止，在黑曲霉进化枝之外的相对较少的真菌中发现了含有 2-benzyl-4H-pyran-4-one 和 2-benzylpyridin-4(1H)-one 亚结构的天然产物。在探索这些化合物在曲霉属中的存在情况时，确定不寻常的呋喃吡咯张力醇 A 和 B（5 和 6）以及 JBIR-86 和 JBIR-87（9 和 10）的结构不正确，应重新指定为 2-benzyl-4H-pyran-4-ones（分别为 7、8、11e 和 12）。还检查了 2-benzylpyridin-4(1H)-ones nygerones A 和 B（1 和 2）中独特的 N-苯基基团的起源，并确定添加到培养基中的 N-苯基酰胺是产生这些代谢物的合适底物；然而，这种现象仍然仅限于我们收集的单一真菌（黑曲霉 ATCC 1015）。在黑曲霉中检测到多种2-benzyl-4H-pyran-4-ones和2-benzylpyridin-4(1H)-ones，但在所有11个测试菌株中仅检测到pestalamide B (13)。这些代谢物以及一组合成类似物对几种念珠菌菌株、黄曲霉和烟曲霉表现出较弱的抗真菌活性。
To date, natural products containing 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one substructures have been encountered in relatively few fungi outside of the black aspergilli clade. While exploring the occurrence of these compounds among Aspergillus spp., it was determined that the structures of the unusual furopyrrols tensidols A and B (5 and 6) and JBIR-86 and JBIR-87 (9 and 10) were incorrect and should be reassigned as 2-benzyl-4H-pyran-4-ones (7, 8, 11e, and 12, respectively). The origin of the unique N-phenyl groups in the 2-benzylpyridin-4(1H)-ones nygerones A and B (1 and 2) was also examined and it was established that N-phenylamides added to the culture medium were suitable substrates for generating these metabolites; however, this phenomenon remained limited to a single fungus in our collection (Aspergillus niger ATCC 1015). A variety of 2-benzyl-4H-pyran-4-ones and 2-benzylpyridin-4(1H)-ones were detected among the black aspergilli, but only pestalamide B (13) was found in all eleven of the tested strains. These metabolites, as well as a group of synthetic analogues demonstrated weak antifungal activity against several Candida strains, Aspergillus flavus, and Aspergillus fumigatus.
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影响因子：
5.1
作者：
Hiort, J;Maksimenka, K;Bringmann, G
通讯作者：
Bringmann, G
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影响因子：
5.1
作者：
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通讯作者：
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影响因子：
5.1
作者：
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通讯作者：
Gerwick, William H.
DOI：
10.1023/b:anto.0000024907.85688.05
发表时间：
2004-08-01
影响因子：
2.6
作者：
Abarca, ML;Accensi, F;Cabañes, FJ
通讯作者：
Cabañes, FJ
影响因子：
3.3
作者：
Fukuda, Takashi;Hasegawa, Yoko;Omura, Satoshi
通讯作者：
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