蓝花黄芩内生真菌Aspergillus terreus HQ100X-1次级代谢产物研究
收稿日期: 2022-02-13
修回日期: 2022-03-28
网络出版日期: 2022-06-23
基金资助
国家自然科学基金(22167013); 海南省重点研发项目(ZDYF2021SHFZ221); 海南省自然科学基金(221RC541); 海南省教育厅项目(Hnky2021ZD-10); 海南省研究生创新科研课题(Hys2021-72); 大学生创新创业训练计划(202111658002); 大学生创新创业训练计划(202111658003)
Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana
Received date: 2022-02-13
Revised date: 2022-03-28
Online published: 2022-06-23
Supported by
National Natural Science Foundation of China(22167013); Key Project of Research and Development of Hainan Province(ZDYF2021SHFZ221); Hainan Provincial Natural Science Foundation of China(221RC541); Education Department of Hainan Province(Hnky2021ZD-10); Program for Hainan Provincial Graduate Innovation Research Project(Hys2021-72); Innovation Training Program for College Students(202111658002); Innovation Training Program for College Students(202111658003)
从蓝花黄芩内生真菌土曲霉(Aspergillus terreus) HQ100X-1发酵产物中分离得到2个新化合物[terrustone (1)和asperteretone G (2)], 10个已知化合物(3~12), terrustone (1)为具有4个连续手性中心的三羟基环戊酮类化合物, 它们的结构以及绝对构型是通过1D/2D NMR结合电子圆二色谱(ECD)计算来确定. 抗菌实验表明, 化合物rbrolide R (4)对金黄色葡萄球菌有一定的抑菌活性, 其最低抑菌浓度(MIC)值为2.5 μg/mL.
关键词: 蓝花黄芩; 土曲霉(Aspergillus terreus); 抗菌活性
黄丹 , 农旭华 , 杨建妮 , 李琛 , 韩长日 , 陈光英 , 宋小平 , 孙振范 , 惠阳 , 陈文豪 . 蓝花黄芩内生真菌Aspergillus terreus HQ100X-1次级代谢产物研究[J]. 有机化学, 2022 , 42(9) : 2961 -2966 . DOI: 10.6023/cjoc202202016
Two new compounds, terrustone (1) and asperteretone G (2) together with ten known compounds were isolated from Scutellaria formosana endophytic fungus Aspergillus terreus HQ100X-1, terrustone (1) is a trihydroxycyclopentanone with four consecutive chiral centers. Their structures were determined by 1D/2D NMR data along with electrostatic circular dichroism (ECD) calculation for configurational assignment. Compound rbrolide R (4) showed antibacterial activity against Staphylococcus aureus with minimum inhibitory concentration (MIC) value of 2.5 μg/mL.
| [1] | Shang, X. F.; He, X. R.; He, X. Y.; Li, M. X.; Zhang, R. X.; Fan, P. C.; Zhang, Q. L.; Jia, Z. P. J. Ethnopharmacology 2010, 128, 279. |
| [2] | Bruno, M.; Piozzi, F.; Rosselli, S. Nat. Prod. Rep. 2002, 19, 357. |
| [3] | Dai, S. J.; Chen, M.; Liu, K.; Jiang, Y. T.; Shen, L. Chem. Pharm. Bull. 2006, 54, 869. |
| [4] | Dai, S. J.; Tao, J. Y.; Liu, K.; Jiang, Y. T.; Shen, L. Phytochemistry 2006, 67, 1326. |
| [5] | Dai, S. J.; Ling, D. D.; Ren, Y.; Liu, K.; Shen, L. Chem. Pharm. Bull. 2008, 56, 207. |
| [6] | Dai, S. J.; Peng, W. B.; Shen, L.; Zhang, D. W.; Ren, Y. J. Asian Nat. Prod. Res. 2009, 11, 451. |
| [7] | Dai, S. J.; Qu, G. W.; Yu, Q. Y.; Zhang, D. W.; Li, G. S. Fitoterapia 2010, 81, 737. |
| [8] | Wu, T. Z.; Wang, Q.; Jiang, C.; Susan, M. N.; Cui, H.; Wang, Y.; Yan, Y.; Xu, J. J. Nat. Prod. 2015, 78, 500. |
| [9] | Chen, X.; Chen, W. H.; Chen, G. Y.; Han, C. R.; He, J. J.; Zhou, X. M.; Yu, Z. X.; Dai, C. Y.; Song, X. P. Phytochemistry 2018, 145, 1. |
| [10] | Chen, X.; Chen, G. Y.; Chen, W. H.; Han, C. R.; Song, X. P.; Pan, Y. J. Chin. Med. Mater. 2016, 39, 2240. (in Chinese) |
| [10] | (陈欣, 陈光英, 陈文豪, 韩长日, 宋小平, 潘怡, 中药材, 2016, 39, 2240.) |
| [11] | Chen, X.; Chen, G. Y.; Chen, W. H.; Han, C. R.; Song, X. P.; Wu, Y. Chin. J. Trop. Agric. 2016, 36, 93. (in Chinese) |
| [11] | (陈欣, 陈光英, 陈文豪, 韩长日, 宋小平, 吴燕, 热带农业科学, 2016, 36, 93.) |
| [12] | Zhang, N. M.S. Thesis, Jinan University, Guangdong, 2019. (in Chinese) |
| [12] | (张娜, 硕士论文, 暨南大学, 广东, 2019.) |
| [13] | Liu, M. T.; Qi, C. X.; Sun, W. G.; Shen, L.; Wang, J. P.; Liu, J. J.; Lai, Y. J. Xue, Y. B.; Hu, Z. X.; Zhang, Y. H. Front. Chem. 2018, 6, 422. |
| [14] | Zhou, K.; Zhu, L.; Wang, X. L.; Zhang, T. D.; Wang, Y. D.; Dong, W.; Ji, B. K.; Yang, H. Y.; Du, G.; Hu, Q. F.; Zhou, M. Chem. Nat. Compd. 2016, 52, 591. |
| [15] | Pal, A.; Banik, B. K. Heterocycl. Lett. 2020, 10, 537. |
| [16] | Qi, C. X.; Gao, W. X.; Wang, J. P.; Liu, M. T.; Zhang, J. W.; Chen, C. M.; Hu, Z. X.; Xue, Y. B.; Li, D. Y.; Zhang, Q.; Lai, Y. J.; Zhou, Q.; Zhu, H. C.; Zhang, Y. H. Fitoterapia 2018, 130, 134. |
| [17] | Bao, J.; Li, X. X.; Zhu, K. L.; He, F.; Wang, Y. Y.; Yu, J. H.; Zhang, X. Y.; Zhang, H. Fitoterapia 2021, 150, 104856. |
| [18] | Cazar, M. E.; Schmeda-Hirschmann, G.; Astudillo, L. J. Microbiol. Biotechnol. 2005, 21, 1067. |
| [19] | Wang, Y.; Zheng, J. K.; Liu, P. P.; Wang, W.; Zhu, W. M. Mar. Drugs 2011, 9, 1368. |
| [20] | He, F.; Bao, J.; Zhang, X. Y.; Tu, Z. C.; Shi, Y. M.; Qi, S. H. J. Nat. Prod. 2013, 76, 1182. |
| [21] | Guo, F.; Li, Z. L.; Xu, X. W.; Wang, K. B.; Shao, M. L.; Zhao, F.; Wang, H. F.; Hua, H. M.; Pei, Y. H.; Bai, J. Fitoterapia 2016, 113, 44. |
| [22] | Parvatkar, R. R.; D'Souza, C.; Tripathi, A.; Naik, C. G. Phytochemistry 2009, 70, 128. |
| [23] | Song, X. M.; Zhou, X. M.; Li, X. B.; Zheng, C. J.; Huang, G. L.; Yu, Z. X.; Song, X. P.; Chen, G. Y. Chin. J. Org. Chem. 2015, 35, 2102. (in Chinese) |
| [23] | (宋鑫明, 周学明, 李小宝, 郑彩娟, 黄国雷, 余章昕, 宋小平, 陈光英, 有机化学, 2015, 35, 2102.) |
/
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〉 |