软珊瑚共附生真菌Aspergillus sp.EGF15-0-3的柳珊瑚酸类代谢产物研究

doi:10.6023/cjoc201911040

有机化学 ›› 2020, Vol. 40 ›› Issue (5): 1275-1280.DOI: 10.6023/cjoc201911040 上一篇下一篇

研究论文

软珊瑚共附生真菌Aspergillus sp.EGF15-0-3的柳珊瑚酸类代谢产物研究

冯婵^a, 韦霞^a, 胡金姗^a, 王思玉^a, 刘炳新^a, 谢珍玉^b, 荣莉^a, 李小翚^a, 张翠仙^a

a 广州中医药大学中药学院广州 510006;
b 海南大学药学院海口 570228

收稿日期:2019-11-30 修回日期:2020-01-13 发布日期:2020-02-15
通讯作者: 李小翚, 张翠仙 E-mail:zhangcuixian@gzucm.edu.cn;lxh@gzucm.edu.cn
基金资助:
国家自然科学基金（No.81741160）、广东省自然科学基金（No.2014A030313411）、广东省科技计划（Nos.2017A020217008，2015A020216017）、广东省自然资源厅广东省海洋经济发展海洋六大产业专项资金（No.粤自然资合[2020]039）、广东省中药药效物质基础和创新药物研究重点实验室开放课题、广州中医药大学薪火计划重点项目（No.XH20170110）和海南大学南海海洋资源利用国家重点实验室开放课题（No.2016003）资助项目.

Researches on the Subergane-Type Sesquiterpenes from the Soft Coral-Derived Fungus Aspergillus sp. EGF15-0-3

Feng Chan^a, Wei Xia^a, Hu Jinshan^a, Wang Siyu^a, Liu Bingxin^a, Xie Zhenyu^b, Rong Li^a, Li Xiaohui^a, Zhang Cuixian^a

a School of Pharmaceutical Science, Guangzhou University of Chinese Medicine, Guangzhou 510006;
b College of Marine Science, Hainan University, Haikou 570228

Received:2019-11-30 Revised:2020-01-13 Published:2020-02-15
Supported by:
Project supported by the National Natural Science Foundation of China (No.81741160), the Natural Science Foundation of Guangdong Province (No. 2014A030313411), the Science and Technology Planning Project of Guangdong Province (Nos. 2017A020217008, 2015A020216017), the Special Project for Marine Economic Development (Six Major Marine Industries) of Guangdong Province of Department of Natural Resources of Guangdong Province (No. [2020]039), the Open Subject of Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, the Fire Plan Project of the Guangzhou University of Chinese Medicine (No. XH20170110), and the Open Subject of State Key Laboratory of Marine Resources Utilization in the South China Sea of Hainan University (No. 2016003).

文章分享

摘要/Abstract

首次从软珊瑚共附生曲霉属真菌Aspergillus sp.EGF15-0-3中分离得到可逆性胆碱酯酶抑制剂环戊烷倍半萜类化合物柳珊瑚酸（1）及其类似物2-脱氧-2β-羟基柳珊瑚酸（2），并确定其结构.根据单菌株多次级代谢产物（OSMAC）策略和富营养化培养，在23种不同的培养基中首次应用全球天然产物分子网络（GNPS）检测1和2是否存在，并选出1和2的最佳培养基组成.结果表明，除马铃薯葡萄糖肉汤（PDB）培养基外，1还存在其他6种培养基中，2的含量在液体和大米培养基中不同，其中GPY+CaCO₃培养基为1和2的最佳培养基.首次证实软珊瑚共附生曲霉属真菌EGF15-0-3是1和2的可能微生物来源，同时也验证了海洋无脊椎动物产生新颖的具有生物活性的次级代谢产物通常来自内生、附生、共生或环境微生物的假说.

关键词: 软珊瑚附生真菌, 曲霉属真菌Aspergillus sp.EGF15-0-3, 柳珊瑚酸, GNPS

Subergorgic acid (1), a cyclopentapentalane sesquiterpenoid and potential reversible cholinesterase inhibitor, and its analogue 2-deoxy-2β-hydroxysubergorgic acid (2) were first isolated from soft coral-associated symbiotic and epiphytic fungus Aspergillus sp. EGF15-0-3. Their structures were established by NMR and HRESIMS spectroscopic data. According to the strategy of one strain many compounds (OSMAC) and eutrophic culture, Global Natural Products Molecular Networking (GNPS) was applied to detect the presence of compounds 1 and 2 in 23 different media for optimal medium compositions. As a result, compound 1 was found in 6 different media besides potato dextrose broth (PDB) medium, the contents of 2 were different in the solid and liquid media, and the best medium for compounds 1 and 2 was GPY+CaCO₃. It was demonstrated that the soft coral-associated symbiotic and epiphytic fungus Aspergillus sp. EGF15-0-3 was the microbiological producer of compounds 1 and 2. This work provided strong evidence to support the hypothesis that novel and bioactive secondary metabolites produced by marine invertebrates often come from endogenetic, epiphytic, symbiotic or environmental microorganisms.

Key words: soft coral-associated symbiotic and epiphytic fungus, Aspergillus sp.EGF15-0-3, subergorgic acid, GNPS

引用此文

冯婵, 韦霞, 胡金姗, 王思玉, 刘炳新, 谢珍玉, 荣莉, 李小翚, 张翠仙. 软珊瑚共附生真菌Aspergillus sp.EGF15-0-3的柳珊瑚酸类代谢产物研究[J]. 有机化学, 2020, 40(5): 1275-1280.

Feng Chan, Wei Xia, Hu Jinshan, Wang Siyu, Liu Bingxin, Xie Zhenyu, Rong Li, Li Xiaohui, Zhang Cuixian. Researches on the Subergane-Type Sesquiterpenes from the Soft Coral-Derived Fungus Aspergillus sp. EGF15-0-3[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1275-1280.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Wu, Z. D.; Yao, Z. N.; Long, K. H. Acta Sci. Nat. Univ. Sunyatseni 1982, 21, 69(in Chinese). (巫中德, 姚仲年, 龙康侯, 中山大学学报, 1982, 21, 69.)
[2] Niu, L. W.; Dai, J. B.; Wan, Z. L.; Liang, D. C.; Wu, Z. D.; Yao, Z. N.; Long, K. H. Sci. China 1985, 15, 709(in Chinese). (牛立文, 戴金璧, 万柱礼, 梁栋材, 巫中德, 姚仲年, 龙康侯, 中国科学, 1985, 15, 709.)
[3] Groweiss, A.; Fenical, W.; He, C. H.; Clardy, J.; Yao, Z. N.; Long, K. H. Tetrahedron Lett. 1985, 26, 2379.
[4] Chen, B. H.; Jiao, K. F.; Ji, Q. E.; Song, H. Q.; Feng, R. Chin. Sci. Bull. 1990, 38, 142(in Chinese). (陈邦华, 焦克芳, 纪庆娥, 宋鸿锵, 冯锐, 科学通报, 1990, 38, 142.)
[5] Huang, Q. X.; Cheng, W.; Long, H. L.; Liu, H. G.; Ofwegen, L. V.; Lin, W. H. Helv. Chim. Acta 2015, 98, 1202.
[6] Wu, Z. D.; Peng, Y. C.; Lu, H. N.; Huang, H. P.; Long, K. H. Acta Sci. Nat. Univ. Sunyatseni 1987, 26, 104(in Chinese). (巫中德, 彭映才, 陆慧宁, 黄红平, 龙康侯, 中山大学学报, 1987, 26, 104.)
[7] Chen, B. H.; Jiao, K.F. Chin. J. Med. Chem. 1991, 2, 1(in Chinese). (陈邦华, 焦克芳, 中国药物化学杂志, 1991, 2, 1.)
[8] Peng, W. D.; Xu, S. B.; Peng, X. Acta Pharmacol. Sin. 1996, 17, 83(in Chinese). (彭汶铎, 许实波, 彭逊, 中国药理学报, 1996, 17, 83.)
[9] Chen, B. H.; Jiao, K. F.; Ji, Q. E.; Song, H. Q. Chin. Sci. Bull. 1990, 35, 1335(in Chinese). (陈邦华, 焦克芳, 纪庆娥, 宋鸿锵, 科学通报, 1990, 35, 1335.)
[10] Peng, W. D.; Xu, S. B. Acta Pharm. Sin. 1994, 29, 662(in Chinese). (彭汶铎, 许实波, 药学学报, 1994, 29, 662.)
[11] Peng, W. D. Chin. Pharm. J. 1998, 11, 685(in Chinese). (彭汶铎, 中国药学杂志, 1998, 11, 685.)
[12] Dudek, C. M. Diss. Abstr. Int., B 1991, 51, 3378.
[13] Crimmins, M. T.; Dudek, C.M.; Cheung, A. W. H. Tetrahedron Lett. 1992, 33, 181.
[14] Meister, P. G. Diss. Abstr. Int., B 1992, 52, 5832.
[15] Dragojlovic, V. Diss. Abstr. Int., B 1994, 55, 900.
[16] Dragojlovic, V. Molecules 2000, 5, 674.
[17] Iwata, C.; Takemoto, Y.; Doi, M.; Imanishi, T. J. Org. Chem. 1988, 53, 1623.
[18] Wender, P. A.; deLong, M. A. Tetrahedron Lett. 1990, 38, 5429.
[19] Paquette, L. A.; Meister, P. C.; Friedrich, D.; Sauer, D. R. J. Am. Chem. Soc. 1993, 115, 49.
[20] deLong, M. A. Diss. Abstr. Int., B 1993, 53, 3477.
[21] Gilbert, J. C.; Yin, J. D. Tetrahedron 2008, 64, 5482.
[22] Sun, D.W.; Liu, M.; Cao, F.; Wang, C.; Wang, C. Y. Chem. Nat. Compd. 2017, 53, 185.
[23] Huang, Q. X.; Wei, C.; Long, H. L.; Liu, H. G.; Ofwegen, L. V.; Lin, W. H. Helv. Chim. Acta 2015, 98, 1202.
[24] Qi, S. H.; Zhang, S.; Li, X.; Li, Q. X. J. Nat. Prod. 2005, 68, 1288.
[25] Parameswaran, P. S.; Naik, C. G.; Kamat, S. Y.; Puar, M. S.; Das, P.; Hegde, V. R. J. Nat. Prod. 1998, 61, 832.
[26] Wang, G. H.; Ahmed, A. F.; Sheu, J. H.; Duh, C. H.; Shen, Y. C.; Wang, L. T. J. Nat. Prod. 2002, 65, 887
[27] Wang, G. H.; Ahmed, A. F.; Kuo, Y. H.; Sheu, J. H. J. Nat. Prod. 2002, 65, 1033.
[28] Sheu, J. H.; Hung, K. C.; Wang, G. H.; Duh, C. Y. J. Nat. Prod. 2000, 63, 1603.
[29] Guo, Z. Q.; Chai, X. Y.; Yang, B.; Zhou, X. F.; Liu, Y. H.; Tu, P. F. J. Chin. Pharm. Sci. 2013, 22, 282.
[30] Deng, Y. M.S. Thesis, Guangzhou University of Chinese Medicine, Guangzhou, 2015 (in Chinese). (邓芸, 硕士论文, 广州中医药大学, 广州, 2015).
[31] Ning, Q. J. M.S. Thesis, Ocean University of China, Qingdao, 2013 (in Chinese). (宁勤建, 硕士论文, 中国海洋大学, 青岛, 2013).
[32] Bode, H. B.; Bethe, B.; Höfs, R.; Zeeck, A. ChemBioChem 2002, 3, 619.
[33] Fan, B.; Parrot, D.; Blümel, M.; Labes, A.; Tasdemir, D. Mar. Drugs 2019, 17, 1.
[34] Tran-Cong, N. M.; Mándi, A.; Kurtán, T.; Müller, W. E. G.; Kalscheuer, R.; Lin, W. H.; Liu, Z.; Proksch, P. RSC Adv. 2019, 9, 27279.
[35] Huang, L. H.; Xu, M. Y.; Li, H. J.; Li, J. Q.; Chen, Y. X.; Ma, W. Z.; Li, Y. P.; Xu, J.; Yang, D. P.; Lan, W. J. Org. Lett. 2017, 19, 4888.
[36] Yang, J. Y.; Sanchez, L. M.; Rath, C. M.; Liu, X.; Boudreau, P. D.; Bruns, N.; Glukhov, E.; Wodtke, A.; de Felicio, R.; Fenner, A.; Wong, W. R.; Linington, R. G.; Zhang, L.; Debonsi, H. M.; Gerwick, W. H.; Dorrestein, P. C. J. Nat. Prod. 2013, 76, 1686.
[37] Nothias, L. F.; Nothias-Esposito, M.; da Silva, R.; Wang, M.; Protsyuk, I.; Zhang, Z.; Sarvepalli, A.; Leyssen, P.; Touboul, D.; Costa, J.; Paolini, J.; Alexandrov, T.; Litaudon, M.; Dorrestein, P. C. J. Nat. Prod. 2018, 81, 758.
[38] Tao, Y. W.; Li, P. L.; Zhang, D. J.; Glukhov, E.; Gerwick, L.; Zhang, C.; Murray, T. F.; Gerwick, W. H. J. Org. Chem. 2018, 83, 3034.
[39] https://gnps.ucsd.edu//ProteoSAFe/result.jsp?task=f3bd06ec4c9-a4611bd6f291ca9feff32&view=cluster_details&protein=9498.
[40] https://gnps.ucsd.edu//ProteoSAFe/result.jsp?task=f3bd06ec4c9a4-611bd6f291ca9feff32&view=cluster_details&protein=9713.
[41] https://gnps.ucsd.edu/ProteoSAFe/result.jsp?view=network_displayer&componentindex1&task=71af1ef2f77d49c1bcc8893c96f5d57-d&show=true.

软珊瑚共附生真菌Aspergillus sp.EGF15-0-3的柳珊瑚酸类代谢产物研究

Researches on the Subergane-Type Sesquiterpenes from the Soft Coral-Derived Fungus Aspergillus sp. EGF15-0-3

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 0

编辑推荐

相关统计

本文评价