Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii

被引:8
作者
Form, Imke C. [1 ]
Bonus, Michele [2 ]
Gohlke, Holger [2 ]
Lin, Wenhan [3 ]
Daletos, Georgios [1 ]
Proksch, Peter [1 ]
机构
[1] Heinrich Heine Univ Dusseldorf, Inst Pharmaceut Biol & Biotechnol, Univ Str 1, D-40225 Dusseldorf, Germany
[2] Heinrich Heine Univ Dusseldorf, Inst Pharmaceut & Med Chem, Univ Str 1, D-40225 Dusseldorf, Germany
[3] Peking Univ, Hlth Sci Ctr, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
关键词
Aspergillus wentii; Bianthrone; DFT-based quantum chemical calculations; Structure elucidation; METABOLITES; STEREOCHEMISTRY; CONSTITUENTS; H-1;
D O I
10.1016/j.bmc.2019.07.021
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Five new metabolites, including the xanthone derivative wentixanthone A (1), the benzophenone wentiphenone A (2), the diastereomeric mixtures of the bianthrones wentibianthrone A (3a, b) and wentibianthrone B (4a, b), as well as (10R, 10'S)-wentibianthrone C (5a) and (10R, 10'R)-wentibianthrone C (5b) were obtained from the fungus Aspergillus wentii, isolated from soil of the hypersaline lake El Hamra in Wadi El-Natrun, Egypt. The structures of the isolated compounds were established by one and two-dimensional NMR and MS spectroscopic analysis. The relative configuration of bianthrones (3-5) was elucidated by comparison of experimental and computed H-1 NMR chemical shifts. Results of biological assays are reported.
引用
收藏
页数:11
相关论文
共 41 条
[1]   Fast protein fold estimation from NMR-derived distance restraints [J].
Angyan, Annamaria F. ;
Perczel, Andras ;
Pongor, Sandor ;
Gaspari, Zoltan .
BIOINFORMATICS, 2008, 24 (02) :272-275
[2]  
[Anonymous], 2016, SCHROD REL 2016 2 MA
[3]  
[Anonymous], 2016, SCHROD REL 2016 2 LI
[4]  
ASSANTE G, 1980, GAZZ CHIM ITAL, V110, P629
[5]   Integrated modeling program, applied chemical theory (IMPACT) [J].
Banks, JL ;
Beard, HS ;
Cao, YX ;
Cho, AE ;
Damm, W ;
Farid, R ;
Felts, AK ;
Halgren, TA ;
Mainz, DT ;
Maple, JR ;
Murphy, R ;
Philipp, DM ;
Repasky, MP ;
Zhang, LY ;
Berne, BJ ;
Friesner, RA ;
Gallicchio, E ;
Levy, RM .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2005, 26 (16) :1752-1780
[6]   THE FUNGI: 1, 2, 3 ... 5.1 MILLION SPECIES? [J].
Blackwell, Meredith .
AMERICAN JOURNAL OF BOTANY, 2011, 98 (03) :426-438
[7]   BIOLOGICAL EFFECTS OF CYCLOSPORIN-A - NEW ANTILYMPHOCYTIC AGENT [J].
BOREL, JF ;
FEURER, C ;
GUBLER, HU ;
STAHELIN, H .
AGENTS AND ACTIONS, 1976, 6 (04) :468-475
[8]   A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics [J].
Cances, E ;
Mennucci, B ;
Tomasi, J .
JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) :3032-3041
[9]   Filamentous fungi from extreme environments as a promising source of novel bioactive secondary metabolites [J].
Chavez, Renato ;
Fierro, Francisco ;
Garcia-Rico, Ramon O. ;
Vaca, Inmaculada .
FRONTIERS IN MICROBIOLOGY, 2015, 6
[10]   Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture [J].
Chen, Huiqin ;
Daletos, Georgios ;
Abdel-Aziz, Mohamed S. ;
Thomy, Dhana ;
Dai, Haofu ;
Broetz-Oesterhelt, Heike ;
Lin, Wenhan ;
Proksch, Peter .
PHYTOCHEMISTRY LETTERS, 2015, 12 :35-41