Bioactive Maleic Anhydrides and Related Diacids from the Aquatic Hyphomycete Tricladium castaneicola
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 t...
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| Published in | Journal of natural products (Washington, D.C.) Vol. 78; no. 4; pp. 639 - 644 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society and American Society of Pharmacognosy
24.04.2015
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Imokawa, Genji Kaida, Kenichi Choi, Bong-Keun Furukawa, Hiroyuki Tomura, Tomohiko Han, Chunguang Fudou, Ryosuke Ojika, Makoto |
| AuthorAffiliation | Ajinomoto Co., Inc Research Center for Materials Science Institute for Innovation Graduate School of Bioagricultural Sciences Nagoya University R&D Planning Department Chubu University Center for Nutraceutical and Pharmaceutical Materials Research Institute for Biological Functions Myongji University |
| AuthorAffiliation_xml | – name: Research Center for Materials Science – name: Graduate School of Bioagricultural Sciences – name: Research Institute for Biological Functions – name: Center for Nutraceutical and Pharmaceutical Materials – name: Ajinomoto Co., Inc – name: Nagoya University – name: Institute for Innovation – name: Myongji University – name: Chubu University – name: R&D Planning Department |
| Author_xml | – sequence: 1 givenname: Chunguang surname: Han fullname: Han, Chunguang – sequence: 2 givenname: Hiroyuki surname: Furukawa fullname: Furukawa, Hiroyuki – sequence: 3 givenname: Tomohiko surname: Tomura fullname: Tomura, Tomohiko – sequence: 4 givenname: Ryosuke surname: Fudou fullname: Fudou, Ryosuke – sequence: 5 givenname: Kenichi surname: Kaida fullname: Kaida, Kenichi – sequence: 6 givenname: Bong-Keun surname: Choi fullname: Choi, Bong-Keun – sequence: 7 givenname: Genji surname: Imokawa fullname: Imokawa, Genji – sequence: 8 givenname: Makoto surname: Ojika fullname: Ojika, Makoto email: ojika@agr.nagoya-u.ac.jp |
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| Cites_doi | 10.1021/ol060916w 10.1111/j.1574-6976.2011.00266.x 10.1021/ja305593y 10.1055/s-0031-1290986 10.1007/s00403-013-1376-z 10.7164/antibiotics.54.17 10.1016/S0040-4020(01)87178-7 10.1021/np980496m 10.1002/jlac.198719870841 10.7164/antibiotics.54.22 10.1016/S0007-1536(75)80139-2 10.1016/0957-4166(95)00296-2 10.1021/np50046a006 10.1021/jo00079a026 10.1021/np50123a022 10.1039/p19720002584 10.1007/BF02033573 |
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| SubjectTerms | 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 |
| Title | Bioactive Maleic Anhydrides and Related Diacids from the Aquatic Hyphomycete Tricladium castaneicola |
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