New perylenequinone derivatives from the endophytic fungus Alternaria tenuissima SS77

被引：15
作者：
Chagas, Fernanda O. [1 ]
Dias, Luis G. [2 ]
Pupo, Monica T. [1 ]
机构：
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias Farmaceut, Ave Cafe S-N, BR-14040903 Ribeirao Preto, SP, Brazil
[2] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, Ave Bandeirantes 3900, BR-14040901 Ribeirao Preto, SP, Brazil
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 29期
基金：
巴西圣保罗研究基金会;
关键词：
Perylenequinones; Mycotoxins; Phytotoxins; Biogenesis; Endophyte; ALTERTOXIN-II; METABOLITES; CERCOSPORIN; PIGMENTS; QUINONE; TAUTOMERISM; PHYTOTOXINS; ANTIFUNGAL; TOXINS;
D O I：
10.1016/j.tetlet.2016.06.035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new natural products, 1,4,6b,7,10-pentahydroxy-1,2,6b,7,8,12b-hexahydroperylene-3,9-dione (1), 1,4,9,12a-tetrahydroxy-12-methoxy-1,2,11,12,12a,12b-hexahydroperylene-3,10-dione (2) and 1,4,9-tri-hydroxy-1,2-dihydroperylene-3,10-dione (3), were obtained from cultures of the endophytic fungus Alternaria tenuissima SS77. Their chemical structures were determined by combined analysis of one and two-dimensional NMR spectra, UV and ESIHRMS data. Compound 3 is likely an intermediate in the biosynthetic pathway of some perylenequinones produced by this fungus. A new hypothesis for the biosynthesis of partially reduced perylenequinones is suggested. (C) 2016 Elsevier Ltd. All rights reserved.
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收藏
页码：3185 / 3189
页数：5
相关论文
共 35 条
[1]   Scientific Opinion on the risks for animal and public health related to the presence of Alternaria toxins in feed and food [J].
Alexander, Jan ;
Benford, Diane ;
Boobis, Alan ;
Ceccatelli, Sandra ;
Cottrill, Bruce ;
Cravedi, Jean-Pierre ;
Di Domenico, Alessandro ;
Doerge, Daniel ;
Dogliotti, Eugenia ;
Edler, Lutz ;
Farmer, Peter ;
Filipic, Metka ;
Fink-Gremmels, Johanna ;
Fuerst, Peter ;
Guerin, Thierry ;
Knutsen, Helle Katrine ;
Machala, Miroslav ;
Mutti, Antonio ;
Schlatter, Josef ;
Rose, Martin ;
van Leeuwen, Rolaf .
EFSA JOURNAL, 2011, 9 (10)
[2]  
ANDERSON JM, 1956, CHEM IND-LONDON, P376
[3]   SECONDARY MOLD METABOLITES .16. STEMPHYLTOXINS, NEW REDUCED PERYLENEQUINONE METABOLITES FROM STEMPHYLIUM-BOTRYOSUM VAR LACTUCUM [J].
ARNONE, A ;
NASINI, G ;
MERLINI, L ;
ASSANTE, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :525-530
[4]   NMR-STUDY OF TAUTOMERISM IN NATURAL PERYLENEQUINONES [J].
ARNONE, A ;
MERLINI, L ;
MONDELLI, R ;
NASINI, G ;
RAGG, E ;
SCAGLIONI, L ;
WEISS, U .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (08) :1447-1454
[5]   PIGMENTS OF A FOSSIL ECHINODERM [J].
BLUMER, M .
NATURE, 1960, 188 (4756) :1100-1101
[6]   COLOURING MATTERS OF APHIDIDOE .16. RECONSIDERATION OF STRUCTURE OF ERYTHROAPHINS [J].
CAMERON, DW ;
TODD ;
CROMARTIE, RIT .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JAN) :48-&
[7]   A Mixed Culture of Endophytic Fungi Increases Production of Antifungal Polyketides [J].
Chagas, Fernanda O. ;
Dias, Luis G. ;
Pupo, Monica T. .
JOURNAL OF CHEMICAL ECOLOGY, 2013, 39 (10) :1335-1342
[8]   Molecular analysis of the cercosporin biosynthetic gene cluster in Cercospora nicotianae [J].
Chen, Huiqin ;
Lee, Miin-Huey ;
Daub, Margret E. ;
Chung, Kuang-Ren .
MOLECULAR MICROBIOLOGY, 2007, 64 (03) :755-770
[9]   Photoactivated perylenequinone toxins in fungal pathogenesis of plants [J].
Daub, ME ;
Herrero, S ;
Chung, KR .
FEMS MICROBIOLOGY LETTERS, 2005, 252 (02) :197-206
[10]   THE GYMNOCHROMES - NOVEL MARINE BROMINATED PHENANTHROPERYLENEQUINONE PIGMENTS FROM THE STALKED CRINOID GYMNOCRINUS-RICHERI [J].
DERICCARDIS, F ;
IORIZZI, M ;
MINALE, L ;
RICCIO, R ;
DEFORGES, BR ;
DEBITUS, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6781-6787
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