Abstract
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.
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
MeSH terms
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Ascorbic Acid / pharmacology
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Aspergillus / chemistry*
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Benzophenones / pharmacology
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Biphenyl Compounds
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Dipeptides / chemistry
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Dipeptides / isolation & purification*
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Dipeptides / pharmacology
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Free Radical Scavengers / chemistry
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Free Radical Scavengers / isolation & purification*
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Free Radical Scavengers / pharmacology
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Indole Alkaloids / chemistry
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Indole Alkaloids / isolation & purification*
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Indole Alkaloids / pharmacology
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Inhibitory Concentration 50
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Peptides, Cyclic / chemistry
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Peptides, Cyclic / isolation & purification*
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Peptides, Cyclic / pharmacology
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Picrates / pharmacology
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Piperazines / chemistry
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Piperazines / isolation & purification*
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Piperazines / pharmacology
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Sunscreening Agents / chemistry
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Sunscreening Agents / isolation & purification*
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Sunscreening Agents / pharmacology
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Ultraviolet Rays / adverse effects
Substances
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Benzophenones
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Biphenyl Compounds
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Dipeptides
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Free Radical Scavengers
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Indole Alkaloids
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Peptides, Cyclic
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Picrates
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Piperazines
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Sunscreening Agents
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alanyl-tryptophan anhydride
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golmaenone
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neoechinulin A
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oxybenzone
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1,1-diphenyl-2-picrylhydrazyl
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Ascorbic Acid