Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers.
Two new indole derivatives (3, 4) and three known compounds (1, 2, 5) were isolated as radical scavengers from the culture filtrate of a marine sponge-derived yeast. Their structures were determined to be tyrosol (1), tryptophol (2), 2-(1H-indol-3-yl)ethyl 2-hydroxypropanoate (3), 2-(1H-indol-3-yl)ethyl 5-hydroxypentanoate (4), and cyclo(L-Pro-L-Tyr) (5) on the basis of their spectroscopic data. The absolute configurations of compounds 3 and 5 were determined by chiral HPLC analysis combined with synthesis and Marfey's method, respectively. Each obtained compound was evaluated for DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity, and all compounds exhibited weak activities.
Sugiyama
Yasumasa
Y
Laboratory of Applied Microbiology, School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. sugiyasu@u-shizuoka-ken.ac.jp
Ito
Yuki
Y
Suzuki
Motofumi
M
Hirota
Akira
A
D000818:Animals; D001713:Biphenyl Compounds / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D010843:Pichia / Q000737:chemistry*; D010851:Picrates / Q000494:pharmacology*; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification; D011161:Porifera / Q000382:microbiology*; D000438:Alcohols
D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D007211:Indoles; D010456:Peptides, Cyclic; D010626:Phenylethyl Alcohol; D010851:Picrates; D010879:Piperazines; C545597:2-(1H-indol-3-yl)ethyl 2-hydroxypropanoate; C545598:2-(1H-indol-3-yl)ethyl 5-hydroxypentanoate; C011867:4-hydroxyphenylethanol; C085319:maculosin; C005949:tryptophol; D000438:Alcohols; C004931:1,1-diphenyl-2-picrylhydrazyl