New destruxins from the marine-derived fungus Beauveria felina.
Chemical investigation of the cytotoxic and anti-tuberculosis active butanone extract obtained from the growth media of the marine-derived fungus Beauveria felina led to the isolation of two new destruxins, [beta-Me-Pro] destruxin E chlorohydrin (1) and pseudodestruxin C (3), along with five known cyclic depsipeptides. The structures of the new destruxin derivatives were established by analysis of spectroscopic data, while the absolute configuration of the common amino acid residues was established by Marfey's analysis. The absolute configuration of the 2(R),4(S)-5-chloro-2,4-dihydroxypentanoic acid residue in 1 could be established by application of a J-based configuration method followed by derivatization with R-MPA-Cl and NMR analysis.
Lira
Simone P
SP
Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970, São Carlos, SP, Brazil.
Vita-Marques
Aline M
AM
Seleghim
Mirna H R
MH
Bugni
Tim S
TS
LaBarbera
Daniel V
DV
Sette
Lara D
LD
Sponchiado
Sandra R P
SR
Ireland
Chris M
CM
Berlinck
Roberto G S
RG
D000596:Amino Acids / Q000032:analysis; D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000904:Antibiotics, Antitubercular / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D052982:Beauveria / Q000737:chemistry*; D045744:Cell Line, Tumor; D047630:Depsipeptides / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D005656:Fungal Proteins / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D009183:Mycotoxins / Q000737:chemistry / Q000302:isolation & purification*; D013057:Spectrum Analysis
D000596:Amino Acids; D000903:Antibiotics, Antineoplastic; D000904:Antibiotics, Antitubercular; D047630:Depsipeptides; D005656:Fungal Proteins; D009183:Mycotoxins; C040425:destruxin E