赭曲霉次生代谢产物研究
Study on the Secondary Metabolites of Aspergillus ochraceus

作者: 邹琼宇 , 黄 俊 , 张 莉 , 陈迪钊 , 李 欣 , 贺贵妃 , 梁芬芳 :湖南省怀化学院,民族药用植物资源研究与利用湖南省重点实验室,化学与化学工程系,湖南 怀化; 吴海峰 :中国医学科学院北京协和医学院,药用植物研究所,中草药物质基础与资源利用教育部重点实验室,北京;

关键词: 赭曲霉赭曲霉毒素分离鉴定Aspergillus ochraceus Ochratoxin Isolation and Identification

摘要:
目的:研究赭曲霉次生代谢产物。方法:利用多种色谱层析方法分离出次生代谢产物,通过ESI-MS/MS及NMR等波谱方法鉴定结构。结果:共分离鉴定出9种化合物,依次是赭曲霉毒素A(1)、赭曲霉毒素B(2)、neohydroxyaspergillic acid(3)、(3R)-5-hydroxymellein(4)、5,6-dihydropenicillic acid(5)、mesaconic acid(6)、p-hydroxybenzoic acid(7)、circumdatin G(8)、(22E,24R)-ergosta-7,22-diene-3β,5α,6β- triol(9)。结论:化合物3~9为首次从赭曲霉中分离得到的化合物。

Abstract: Objective: To study the secondary metabolites from Aspergillus ochraceus. Methods: The constit-uents were isolated and purified by column chromatography and preparative TLC. Their structures were identified on the basis of comprehensive spectroscopic methods including ESI-MS and spectral data (1H, 13C-NMR). Results: Nine compounds were isolated and identified as ochratoxin A (1), ochratoxin B (2), neohydroxyaspergillic acid (3), (3R)-5-hydroxymellein (4), 5,6-dihydro- penicillic acid (5), mesaconic acid (6), p-hydroxybenzoic acid (7), circumdatin G (8), (22E,24R)- ergosta-7,22-diene-3β,5α,6β-triol (9). Conclusion: The compounds 3~9 were isolated from Asper-gillus ochraceus for the first time.

文章引用: 邹琼宇 , 吴海峰 , 黄 俊 , 张 莉 , 陈迪钊 , 李 欣 , 贺贵妃 , 梁芬芳 (2017) 赭曲霉次生代谢产物研究。 有机化学研究, 5, 94-99. doi: 10.12677/JOCR.2017.52012

参考文献

[1] El Khoury, A. and Atoui, A. (2010) Ochratoxin A: General Overview and Actual Molecular Status. Toxins, 2, 461-493.
https://doi.org/10.3390/toxins2040461

[2] O’Brien, E. and Dietrich, D.R. (2005) Ochratoxin A: The Continuing Enigma. Critical Reviews in Toxicology, 35, 33- 60.
https://doi.org/10.1080/10408440590905948

[3] Larsen, T.O., Svendsen, A. and Smedsgaard, J. (2001) Biochemical Characterization of Ochratoxin A—Producing Strains of the Genus Penicillium. Applied and Environmental Microbiology, 67, 3630-3635.
https://doi.org/10.1128/AEM.67.8.3630-3635.2001

[4] Wicklow, D.T., Dowd, P.F., Alfatafta, A.A. and Gloer, J.B. (1996) Ochratoxin A: An Antiinsectan Metabolite from the Sclerotia of Aspergillus carbonarius NRRL 369. Canadian Journal of Microbi-ology, 42, 1100-1103.
https://doi.org/10.1139/m96-141

[5] Dais, P., Stefanaki, I., Fragaki, G. and Mikros, E. (2005) Conformational Analysis of Ochratoxin A by NMR Spectroscopy and Computational Molecular Modeling. The Journal of Physical Chemistry B, 109, 16926-16936.
https://doi.org/10.1021/jp058035e

[6] Bredenkamp, M.W., Dillen, J.L.M., van Rooyen, P.H. and Steyn, P.S. (1989) Crystal Structures and Conformational Analysis of Ochratoxin A and B: Probing the Chemical Structure Causing Toxicity. Journal of the Chemical Society, Perkin Transactions, 2, 1835-1839.
https://doi.org/10.1039/p29890001835

[7] Assante, G., Camarda, L., Locci, R., Merlini, L. and Nasini, G. (1981) Papadopoulos. Isolation and Structure of Red Pigments from Aspergillus falvus and Re-lated Species, Grown on a Differential Medium. Journal of Agricultural and Food Chemistry, 29, 785-787.
https://doi.org/10.1021/jf00106a023

[8] Ohta, A., Akita, Y., Izumida, A. and Suzuki, I. (1979) Synthesis of dl-neohydroxy-aspergillic Acid. Chemical and Pharmaceutical Bulletin, 27, 1316-1320.
https://doi.org/10.1248/cpb.27.1316

[9] 魏美燕, 胡谷平, 郑彩娟, 邵长伦, 王长云, 周世宁, 佘志刚, 林永成. 中国南海红树内生真菌Microsphaeropsis sp.二氢异香豆素类化合物研究[J]. 中山大学学报(自然科学版), 2010, 49(2): 68-71.

[10] Devys, M., Barbier, M., Bousquet, J.F. and Kollmann, A. (1994) Isolation of the (–)-(3R)-5-hydroxymellein from the Fungus Septoria nodorum. Phytochemistry, 35, 825-826.

[11] Sassa, T., Hayakari, S., Ikeda, M. and Miura, Y. (1971) Plant Grown Inhibitions Produced by Fungi. Part I. Isolation and Identification of Penicillic Acid and Dihydropenicillic Acid. Agricultural and Biological Chemistry, 35, 2130- 2131.

[12] He, J., Wijeratne, E.M.K., Bashyal, B.P., et al. (2004) Cytotoxic and Other Metabolites of Aspergillus Inhabiting the Rhizosphere of Snoran Desert Plants. Journal of Natural Products, 67, 1985-1991.
https://doi.org/10.1021/np040139d

[13] Collin, P.J. and Sternhell, S. (1966) N.M.R. Spectra of Crotonic, Mesaconic, Citraconic, and , -diluethylacrylic Acids, Their Methyl Esters and Potassium Salts. Australian Journal of Chemistry, 19, 317-320.

[14] 肖美添, 叶静, 洪本博, 昝珂, 屠鹏飞. 白苞蒿化学成分研究[J]. 中国药学杂志, 2011(46): 414-417.

[15] Dai, J.R., Carte, B.K., Sidebottom, P.J., Yew, A.L.S., Ng, S.B., Huang, Y.C. and Butler, M.S. (2001) Circumdatin G, a New Alkaloid from the Fungus Aspergillus ochraceus. Journal of Natural Products, 64, 125-126.
https://doi.org/10.1021/np000381u

[16] 王兴娜, 杜建厂, 谭仁祥, 刘吉开. 担子菌黄卷缘齿菌的化学成分[J]. 中草药, 2005, 36(8): 1126-1130.

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