Bioactive Dihydronaphthoquinone Derivatives from Fusarium solani

• Published in: Journal of natural products (Washington, D.C.) Vol. 77; no. 9; pp. 1992 - 1996
• Main Authors: Takemoto, Kenji, Kamisuki, Shinji, Chia, Pei Thing, Kuriyama, Isoko, Mizushina, Yoshiyuki, Sugawara, Fumio
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.09.2014; Amer Chemical Soc
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; apoptosis; Apoptosis - drug effects; Chemistry, Medicinal; culture media; cytotoxicity; Drug Screening Assays, Antitumor; Fusarium - chemistry; Fusarium solani; HeLa Cells; human umbilical vein endothelial cells; Humans; Life Sciences & Biomedicine; microbial culture; Molecular Structure; Naphthoquinones - chemistry; Naphthoquinones - isolation & purification; Naphthoquinones - pharmacology; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; Pharmacology & Pharmacy; Plant Sciences; Reactive Oxygen Species - metabolism; Science & Technology; spectral analysis; SECONDARY METABOLITES; CANCER-CELLS; APOPTOSIS; INHIBITION; FUNGUS
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/np500175j

New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. Additionally, we demonstrated that karuquinone A induces apoptosis in cancer cells through the generation of reactive oxygen species (ROS).