Phomopsinones A-D: Four New Pyrenocines from Endophytic Fungus Phomopsis sp.

被引:43
作者
Hussain, Hidayat [1 ]
Krohn, Karsten [1 ]
Ahmed, Ishtiaq [1 ]
Draeger, Siegfried [2 ]
Schulz, Barbara [2 ]
Di Pietro, Sebastiano [3 ]
Pescitelli, Gennaro [3 ]
机构
[1] Univ Paderborn, Dept Chem, D-33098 Paderborn, Germany
[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Mikrobiol, D-31806 Braunschweig, Germany
[3] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
关键词
Natural products; Structure elucidation; Circular dichroism; Biological activity; NATURAL-PRODUCTS; ISOCOUMARINS; METABOLITES; DIVERSITY;
D O I
10.1002/ejoc.201101788
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structural elucidation of the compounds isolated from the endophytic Phomopsis sp. revealed phomopsinones AD (14), four new a-pyrone derivatives. Three known compounds were also isolated, namely two phomosines, phomosine A (5) and phomosine C (6), and ergosterol (7). The structures of these compounds were determined by spectroscopic analysis (1H, 13C, 1H1H COSY, HMQC, HMBC, and ROESY NMR, and mass spectrometry), supported by molecular modeling. The absolute configurations of the new compounds 14 were determined by circular dichroism spectroscopy and TDDFT calculations. Preliminary studies indicated that compounds 1 and 4 show strong and good antifungal activity, respectively. Similarly, compounds 2 and 3 showed good antifungal and moderate antibacterial activities as well as antialgal activities.
引用
收藏
页码:1783 / 1789
页数:7
相关论文
共 23 条
[1]  
[Anonymous], 2008, SPART 08
[2]   Computing Chiroptical Properties with First-Principles Theoretical Methods: Background and Illustrative Examples [J].
Autschbach, Jochen .
CHIRALITY, 2009, 21 (1E) :E116-E152
[3]  
Bruhn T., 2010, SPECDIS V 1 51
[4]  
Dai J, 2005, EUR J ORG CHEM, V23, P5100, DOI DOI 10.1002/EJOC.200500471
[5]   Calculation of nuclear spin-spin coupling constants of molecules with first and second row atoms in study of basis set dependence [J].
Deng, Wei ;
Cheeseman, James R. ;
Frisch, Michael J. .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2006, 2 (04) :1028-1037
[6]  
di Bari L., 2010, Computational Spectroscopy. Methods, P241
[7]  
Frisch M. J., 2016, Gaussian 03 Revision B.03
[8]   IDENTIFICATION OF 24-METHYLENE-24, 25-DIHYDROLANOSTEROL AND OTHER POSSIBLE ERGOSTEROL PRECURSORS IN PHYCOMYCES-BLAKESLEEANUS AND AGARICUS-CAMPESTRIS [J].
GOULSTON, G ;
MERCER, EI ;
GOAD, LJ .
PHYTOCHEMISTRY, 1975, 14 (02) :457-462
[9]  
GUNTHER H, 1977, CHEM REV, V77, P599
[10]   The magnitude of fungal diversity: the 1.5 million species estimate revisited [J].
Hawksworth, DL .
MYCOLOGICAL RESEARCH, 2001, 105 :1422-1432