Petrosifungins A and B, novel cyclodepsipeptides from a sponge-derived strain of Penicillium brevicompactum.
A strain of Penicillium brevicompactum derived from a specimen of the Mediterranean sponge Petrosia ficiformis was investigated for its secondary metabolites. Using fast centrifugal partitioning chromatography (FCPC) two previously unknown cyclodepsipeptides, petrosifungins A (1) and B (2), were isolated, both containing two neighboring units of the nonproteinogenic amino acid l-pipecolinic acid. The absolute configurations of all amino acids were established to be l using GITC derivatization and Marfey's method. Furthermore, the known metabolite brevianamide A (3) was isolated. The likewise known compounds mycophenolic acid (4) and asperphenamate (5) were identified from their spectroscopic properties directly in the extract using HPLC-UV, -MS, and -NMR coupling.
Bringmann
Gerhard
G
Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Lang
Gerhard
G
Steffens
Stefan
S
Schaumann
Karsten
K
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D047630:Depsipeptides; D008522:Mediterranean Sea; D015394:Molecular Structure; D009173:Mycophenolic Acid / Q000737:chemistry / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification; D011161:Porifera; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification
D000470:Alkaloids; D047630:Depsipeptides; D010456:Peptides, Cyclic; D010879:Piperazines; D013141:Spiro Compounds; C484198:petrosifungin A; C484199:petrosifungin B; C006794:brevianamide A; D010649:Phenylalanine; C014343:asperphenamate; D009173:Mycophenolic Acid