title: 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.affiliation: Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan.
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Nakamura
authors.forename: Takahiko
authors.initials: T
authors.lastname: Kakuda
authors.forename: Jianhua
authors.initials: J
authors.lastname: Qi
authors.forename: Masayuki
authors.initials: M
authors.lastname: Hirata
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Shintani
authors.forename: Yukio
authors.initials: Y
authors.lastname: Yoshioka
authors.forename: Tetsuji
authors.initials: T
authors.lastname: Okamoto
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Oba
authors.forename: Hideshi
authors.initials: H
authors.lastname: Nakamura
authors.forename: Makoto
authors.initials: M
authors.lastname: Ojika
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008826:Microbial Sensitivity Tests; D010838:Phytophthora / Q000187:drug effects; D011809:Quinones / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D047131:Xestospongia / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D011809:Quinones; C068501:xestoquinone