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.
Li
Yong
Y
Department of Chemistry, Pukyong National University, Busan, Korea.
Li
Xifeng
X
Kim
Se-Kwon
SK
Kang
Jung Sook
JS
Choi
Hong Dae
HD
Rho
Jung Rae
JR
Son
Byeng Wha
BW
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