Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum

• Published in: Tetrahedron Vol. 54; no. 34; pp. 10007 - 10016
• Main Authors: Fukuyama, Yoshiyasu, Iwatsuki, Chie, Kodama, Mitsuaki, Ochi, Masamitsu, Kataoka, Kumi, Shibata, Kozo
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-08-1998
• Subjects: Bacteria; Drupella fragum; Marine
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(98)00593-6

Three new indolequinones, 6-methoxyindole-4,7-quinone (
1), 5-methoxyindole-4,7-quinone (
2) and 5-methylindole-4,7-quinone (
3) were isolated from the mid-intestinal gland of the muricid gastropod
Drupella fragum. The structures of
1 and
2 were established by spectroscopic methods and total synthesis, whereas the structure of
3 was elucidated mainly by NMR spectroscopic analyses. Compounds
1 ∼ 3
exhibited moderate antimicrobial activities against
Staphylococcus aureus, Bacillus subtilis, and
Escherichia coli with MIC = 6.25 ∼ 50 μg/mL.
The structures of antimicrobial indolequinones,
1, 2 and
3 isolated from the mid-intestinal gland of the muricid gastropod
Drupella fragum were established by spectroscopic methods and total synthesis.