Electrospray ionization mass spectra of piperazimycins A and B and gamma-butyrolactones from a marine-derived Streptomyces sp.
Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (1a, 1b). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4-olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three gamma-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed 1D and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.
Shaaban
Khaled A
KA
. Department of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany.
Shaaban
Mohamed
M
Facey
Petrea
P
Fotso
Serge
S
Frauendorf
Holm
H
Helmke
Elisabeth
E
Maier
Armin
A
Fiebig
Heinz H
HH
Laatsch
Hartmut
H
D015107:4-Butyrolactone / Q000737:chemistry / Q000302:isolation & purification*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013302:Streptomyces / Q000737:chemistry* / Q000302:isolation & purification; D014871:Water Microbiology
D047630:Depsipeptides; C518107:piperazimycin A; C518109:piperazimycin B; D015107:4-Butyrolactone