Phomapyrrolidones A-C，来源于内生真菌 Phoma sp. NRRL 46751 的抗结核生物碱。
Phomapyrrolidones A-C, antitubercular alkaloids from the endophytic fungus Phoma sp. NRRL 46751.
机构信息
Southwest Center for Natural Products Research and Commercialization, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, The University of Arizona , 250 E. Valencia Road, Tucson, Arizona 85706, United States.
出版信息
J Nat Prod. 2013 Oct 25;76(10):1860-5. doi: 10.1021/np400391p. Epub 2013 Sep 30.
Abstract
Three new alkaloids, phomapyrrolidones A-C (1-3), bearing a cyclopenta[b]fluorene ring system were isolated from the mycelium extract of the endophytic fungal strain Phoma sp. NRRL 46751, inhabiting Saurauia scaberrinae. Methylation of 1 afforded its N-methyl derivative 4. The planar structures and relative configurations of 1-4 were elucidated by extensive spectroscopic analysis. Phomapyrrolidones B (2) and C (3) exhibited weak antitubercular activity at subcytotoxic concentrations.
摘要
从内生真菌 Phoma sp. NRRL 46751 的菌丝体提取物中分离得到了三个新的生物碱，phomapyrrolidones A-C（1-3），它们都含有一个环戊[b]芴环系统。1 通过甲基化得到了它的 N-甲基衍生物 4。通过广泛的光谱分析阐明了 1-4 的平面结构和相对构型。phomapyrrolidones B（2）和 C（3）在亚细胞毒性浓度下表现出微弱的抗结核活性。
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本文引用的文献
1
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J Med Chem. 2013 Apr 11;56(7):2991-9. doi: 10.1021/jm400034b. Epub 2013 Mar 29.
2
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J Nat Prod. 2012 Mar 23;75(3):361-9. doi: 10.1021/np200769q. Epub 2012 Jan 20.
3
Smardaesidins A-G, isopimarane and 20-nor-isopimarane diterpenoids from Smardaea sp., a fungal endophyte of the moss Ceratodon purpureus.斯玛达西丁 A-G、异松脂烷和 20-降异松脂烷二萜类化合物，来源于斯玛达属内生真菌，是一种苔藓 Ceratodon purpureus 的内生真菌。
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4
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Appl Microbiol Biotechnol. 2012 Feb;93(3):1231-9. doi: 10.1007/s00253-011-3472-3. Epub 2011 Aug 4.
5
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FEMS Microbiol Lett. 2011 Jul;320(2):87-94. doi: 10.1111/j.1574-6968.2011.02297.x. Epub 2011 May 20.
6
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Nat Prod Commun. 2010 Aug;5(8):1175-80.
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Nat Prod Commun. 2009 Nov;4(11):1511-32.
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9
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Phytochemistry. 2008 Feb;69(4):1049-56. doi: 10.1016/j.phytochem.2007.10.031. Epub 2007 Dec 19.
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