Novel relationship between the antifungal activity and cytotoxicity of marine-derived metabolite xestoquinone and its family.

Abstract

Xestoquinone and related metabolites (the xestoquinone family) occur in marine sponges and are known to show a variety of biological activities. In this study, the first comprehensive evaluation of antifungal activity was performed for xestoquinone and nine natural and unnatural analogues in comparison with their cytotoxicity. The cytotoxicity against two human squamous cell carcinoma cell lines, A431 and Nakata, indicated that the terminal quinone structure of the polycyclic molecules was important (xestoquinone, etc.) and that the presence of a ketone group at C-3 of the opposite terminus dramatically diminished the activity (halenaquinone, etc.). In contrast, a ketone group at C-3 enhanced the antifungal activity against the plant pathogen, Phytophthora capsici, regardless of the presence of a quinone moiety. The cytotoxicity and antifungal activity of the xestoquinone family were negatively correlated with each other.

• Authors: Mitsuhiro Nakamura, Takahiko Kakuda, Jianhua Qi, Masayuki Hirata, Tomoaki Shintani, Yukio Yoshioka, Tetsuji Okamoto, Yuichi Oba, Hideshi Nakamura, Makoto Ojika
• Journal: Bioscience, biotechnology, and biochemistry (Biosci Biotechnol Biochem) Vol. 69 Issue 9 Pg. 1749-52 (Sep 2005) ISSN: 0916-8451 [Print] England
• PMID: 16195594 (Publication Type: Journal Article)

Chemical References

• Antifungal Agents
• Antineoplastic Agents
• Quinones
• xestoquinone

Topics

• Animals
• Antifungal Agents (chemical synthesis, pharmacology)
• Antineoplastic Agents (chemical synthesis, pharmacology)
• Cell Line, Tumor
• Drug Screening Assays, Antitumor
• Humans
• Microbial Sensitivity Tests
• Phytophthora (drug effects)
• Quinones (chemistry, pharmacology)
• Structure-Activity Relationship
• Xestospongia (chemistry)