Asperelines A-F, peptaibols from the marine-derived fungus Trichoderma asperellum.
Fermentation of the marine-derived fungus Trichoderma asperellum, collected from the sediment of the Antarctic Penguin Island, resulted in the isolation of six new peptaibols named asperelines A-F (1-6), which are characterized by an acetylated N-terminus and a C-terminus containing an uncommon prolinol residue. Structures were determined by extensive 1D and 2D NMR ((1)H-(1)H COSY, HMQC, HMBC, NOESY) spectroscopic data analysis combined with ESIMS/MS fragmentation. The absolute configurations of the amino acid residues possessing a chiral alpha-carbon and of the prolinol residue were determined to be L and S, respectively, using a new method of (1)H NMR spectroscopic comparison of complexes formed between the chiral reagent Ru(D(4)-Por*)CO and amino acids derived from the peptaibols with those formed with reference standards.
Ren
Jinwei
J
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, People's Republic of China.
Xue
Chunmei
C
Tian
Li
L
Xu
Minjuan
M
Chen
Jian
J
Deng
Zhiwei
Z
Proksch
Peter
P
Lin
Wenhan
W
D000596:Amino Acids / Q000032:analysis / Q000737:chemistry; D000864:Antarctic Regions; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054848:Peptaibols / Q000737:chemistry* / Q000302:isolation & purification*; D017386:Sequence Homology, Amino Acid; D014242:Trichoderma / Q000737:chemistry*
D000596:Amino Acids; D054848:Peptaibols