Scalusamides A-C, new pyrrolidine alkaloids from the marine-derived fungus Penicillium citrinum.
Three new pyrrolidine alkaloids, scalusamides A-C (1-3), were isolated from the cultured broth of the fungus Penicillium citrinum, which was separated from the gastrointestine of a marine fish, and the structures were elucidated by spectroscopic data. The absolute stereochemistry of C-2 in the pyrrolidine unit was determined by HPLC analysis of a Marfey's derivative of the hydrolysate of 1, while that of 2 and 3 was assigned by comparison of spectroscopic data of 3 and reductive products of 1 and 2. On the other hand, each of 1-3 was found to be a mixture of epimers at C-7. Scalusamide A (1) exhibited antifungal and antibacterial activities.
Tsuda
Masashi
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Sasaki
Mai
M
Mugishima
Takao
T
Komatsu
Kazusei
K
Sone
Teruo
T
Tanaka
Michiko
M
Mikami
Yuzuru
Y
Kobayashi
Jun'ichi
J
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D005399:Fishes; D007564:Japan; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011759:Pyrrolidines; C499272:scalusamide A; C499273:scalusamide B; C499274:scalusamide C