Golmaenone, a new diketopiperazine alkaloid from the marine-derived fungus Aspergillus sp.
A new diketopiperazine alkaloid, golmaenone (1). and related alkaloids, neoechinulin A (2). and L-alanyl-L-tryptophan anhydride (3). have been isolated from the culture broth of the marine-derived fungus Aspergillus sp. The structure and absolute stereochemistry of the new compound (1). was assigned by spectroscopic methods and the advanced Marfey's method. Compounds 1 and 2 exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC(50) values of 20 and 24 microM, respectively, which are similar to the positive control, ascorbic acid (IC(50), 20 microM). Compounds 1 and 2 also showed an ultraviolet-A (UV-A) (320--390 nm) protecting activity with ED(50) values of 90 and 170 microM, respectively, which are more active than oxybenzone (ED(50), 350 microM) currently being used as sunscreen.
Department of Chemistry, Pukyong National University, Busan, Korea.
Yong
Y
Li
Xifeng
X
Li
Se-Kwon
SK
Kim
Jung Sook
JS
Kang
Hong Dae
HD
Choi
Jung Rae
JR
Rho
Byeng Wha
BW
Son
D001205:Ascorbic Acid / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D001577:Benzophenones / Q000494:pharmacology; D001713:Biphenyl Compounds; D004151:Dipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010851:Picrates / Q000494:pharmacology; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013473:Sunscreening Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014466:Ultraviolet Rays / Q000009:adverse effects
D001577:Benzophenones; D001713:Biphenyl Compounds; D004151:Dipeptides; D016166:Free Radical Scavengers; D026121:Indole Alkaloids; D010456:Peptides, Cyclic; D010851:Picrates; D010879:Piperazines; D013473:Sunscreening Agents; C490269:alanyl-tryptophan anhydride; C490265:golmaenone; C490266:neoechinulin A; C005290:oxybenzone; C004931:1,1-diphenyl-2-picrylhydrazyl; D001205:Ascorbic Acid