Bioactive Maleic Anhydrides and Related Diacids from the Aquatic Hyphomycete Tricladium castaneicola

• Published in: Journal of natural products (Washington, D.C.) Vol. 78; no. 4; pp. 639 - 644
• Main Authors: Han, Chunguang, Furukawa, Hiroyuki, Tomura, Tomohiko, Fudou, Ryosuke, Kaida, Kenichi, Choi, Bong-Keun, Imokawa, Genji, Ojika, Makoto
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 24.04.2015; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Drug Screening Assays, Antitumor; Hyphomycetes; Japan; Life Sciences & Biomedicine; Maleic Anhydrides - chemistry; Maleic Anhydrides - isolation & purification; Maleic Anhydrides - pharmacology; Melanoma, Experimental - drug therapy; Mitosporic Fungi - chemistry; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oomycetes; Pharmacology & Pharmacy; Phytophthora; Phytophthora - drug effects; Plant Sciences; Science & Technology; Structure-Activity Relationship; Succinates - chemistry; Succinates - isolation & purification; Succinates - pharmacology; Japan; CLAVARIOPSIS-AQUATICA; ACIDS; DERIVATIVES; CYCLIC DEPSIPEPTIDE ANTIBIOTICS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np500773s

Four maleic anhydride derivatives, tricladolides A–D (1–4), and three alkylidene succinic acid derivatives, tricladic acids A–C (5–7), were isolated from the aquatic hyphomycete Tricladium castaneicola. The structures of these compounds were determined by spectroscopic analysis, and all were found to be novel. The compounds exhibited inhibitory activity against fungi, particularly Phytophthora sp., a plant pathogen of oomycetes. The inhibitory activity of these metabolites revealed the importance of the cyclic anhydride structure and the lipophilicity of the alkyl side chain. On the other hand, the cytotoxicity of the compounds against B16 melanoma cells indicated that the cyclic anhydride structure was not essential.