Antioxidative bromoindole derivatives from the mid-intestinal gland of the muricid gastropod Drupella fragum.
Three new bromoindoles, 6-bromo-5-hydroxyindole (1), 6-bromo-4, 5-dihydroxyindole (2), and 6-bromo-4,7-dihydroxyindole (3), were isolated from the midintestinal gland of the muricid gastropod Drupella fragum. The structures of 2 and 3 were elucidated mainly by NMR spectroscopic analyses of their acetyl derivatives, whereas the structure of 1 was established by spectroscopic methods and total synthesis. Antioxidative activity for compounds 1-3 was evaluated by the POV method, and compound 1 was found to have as strong an antioxidative potency as BHT.
Ochi
M
M
Department of Chemistry, Faculty of Science, Kochi University, Kochi 780-8072, Japan, and Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770-8514, Japan.
Kataoka
K
K
Ariki
S
S
Iwatsuki
C
C
Kodama
M
M
Fukuyama
Y
Y
D000085:Acetates / Q000737:chemistry; D000818:Animals; D000975:Antioxidants / Q000302:isolation & purification* / Q000494:pharmacology; D005088:Exocrine Glands / Q000737:chemistry*; D007211:Indoles / Q000302:isolation & purification* / Q000494:pharmacology; D007422:Intestines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010545:Peroxides / Q000737:chemistry; D012908:Snails / Q000737:chemistry*
D000085:Acetates; D000975:Antioxidants; D007211:Indoles; D010545:Peroxides