Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A

doi:10.6023/cjoc202102040

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3292-3296.DOI: 10.6023/cjoc202102040 Previous Articles Next Articles

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Dorsmerunin A的全合成及其抗炎活性研究

李敏欣, 邹秋萍, 杜文绒, 高金春, 李艳平^*(), 毛泽伟^*()

云南中医药大学中药学院昆明 650500

收稿日期:2021-02-22 修回日期:2021-03-27 发布日期:2021-05-25
通讯作者: 李艳平, 毛泽伟
作者简介:
† 共同第一作者
基金资助:
云南省科学技术厅-云南中医药大学应用基础研究联合专项(202001AZ070001-007); 云南省科学技术厅-云南中医药大学应用基础研究联合专项(202001AZ070001-038); 云南中医药大学大学生创新创业训练计划(2019066)

Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A

Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li(), Zewei Mao()

School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming 650500

Received:2021-02-22 Revised:2021-03-27 Published:2021-05-25
Contact: Yanping Li, Zewei Mao
About author:
† (These authors contributed equally to this work).
Supported by:
Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine(202001AZ070001-007); Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine(202001AZ070001-038); Undergraduate Innovation and Entrepreneurship Training Program of Yunnan University of Chinese Medicine(2019066)

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Abstract

Benzofurans have been found to be one of the major sources of drug development for a variety of diseases, and have received increasing attention in the field of synthetic medicinal chemistry. Dorsmerunin A, a natural cytotoxic product of 2-benzylbenzofurans, was isolated from the roots of Dorstenia kameruniana. In this work, Dorsmerunin A was firstly synthesized in 49% total yield from 4-methoxysalicylaldehyde and 2-bromo-4'-methoxyacetophenone through intramolecular condensation, reduction and deprotection. The in vitro anti-inflammatory activity of Dorsomerinein A was initially tested using the murine macrophage RAW264.7 model, and the results showed that it showed good inhibitory effect on NO production at a concentration of 25 μmol/L, as well as proinflammatory factors (IL-6, IL-1β and TNF-α).

Key words: Dorsmerunin A, total synthesis, anti-inflammatory activity, mechanism

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Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.

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Fig. & Tab. 5

Figure 1. In vitro anti-inflammatory activity of Dorsmerunin A

Scheme 1. Benzofuran natural products and drugs

Scheme 2. Synthetic route of Dorsmerunin A

Concentration/(μmol•L^–1)	Survival rate/%
1.5625	109.5
3.125	97.25
6.25	96.36
12.5	81.81
25	61.34

Table 1. Toxicity of Dorsmerunin A

Figure 2. Preliminary anti-inflammatory mechanism of Dorsmerunin A

References 18

[1]	Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2016, 79, 629. doi: 10.1021/acs.jnatprod.5b01055 pmid: 26852623
[2]	Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2020, 83, 770. doi: 10.1021/acs.jnatprod.9b01285 pmid: 32162523
[3]	Wang, W.; Li, N.; Wang, J.; Chen, G.; Huang, R.; Zhao, W.; Li, J.; Si, Y. Phytochemistry 2016, 131, 107. doi: 10.1016/j.phytochem.2016.09.005
[4]	Wang, W. J.; Wang, L.; Liu, Z.; Jiang, R. W.; Liu, Z. W.; Li, M. M.; Zhang, Q. W.; Dai, Y.; Li, Y. L.; Zhang, X. Q.; Ye, W. C. Phytochemistry 2016, 122, 238. doi: 10.1016/j.phytochem.2015.11.013
[5]	He, R.; Zhang, Y.; Wu, L.; Nie, H.; Huang, Y.; Liu, B.; Deng, S.; Yang, R.; Huang, S.; Nong, Z.; Li, J.; Chen, H. Phytochemistry 2017, 138, 170. doi: 10.1016/j.phytochem.2017.01.011
[6]	Ruiz-Vásquez, L.; Mesia, L. R.; Reina-Artiles, M.; López- Rodríguez, M.; González-Platas, J.; Giménez, C.; Cabrera, R.; González-Coloma, A. Phytochem. Lett. 2018, 28, 47. doi: 10.1016/j.phytol.2018.07.002
[7]	Adem, F. A.; Kuete, V.; Mbaveng, A. T.; Heydenreich, M.; Ndakala, A.; Irungu, B.; Efferth, T.; Yenesew, A. Fitoterapia 2018, 128, 26. doi: 10.1016/j.fitote.2018.04.019
[8]	Naik, R.; Harmalkar, D. S.; Xu, X.; Jang, K.; Lee, K. Eur. J. Med. Chem. 2015, 90, 379. doi: 10.1016/j.ejmech.2014.11.047
[9]	Wang, X. Q.; Liu, L. X.; Li, Y.; Sun, C. J.; Chen, W.; Li, L.; Zhang, H. B.; Yang, X. D. Eur. J. Med. Chem. 2013, 62, 111. doi: 10.1016/j.ejmech.2012.12.040
[10]	Shamsuzzaman, H. K. Eur. J. Med. Chem. 2015, 97, 483. doi: 10.1016/j.ejmech.2014.11.039
[11]	Gao, H.; Zhang, X.; Pu, X. J.; Zheng, X.; Liu, B.; Rao, G. X.; Wan, C. P.; Mao, Z. W. Bioorg. Med. Chem. Lett. 2019, 29, 806. doi: 10.1016/j.bmcl.2019.01.025
[12]	Wang, M. X.; Deng, Y. H.; Shao, Z. H. Chin. J. Org. Chem. 2020, 40, 812. (in Chinese) doi: 10.6023/cjoc202000014
	(王美馨, 邓玉华, 邵志会, 有机化学, 2020, 40, 812.) doi: 10.6023/cjoc202000014
[13]	Nevagi, R. J.; Dighe, S. N.; Dighe, S. N. Eur. J. Med. Chem. 2015, 97, 561. doi: 10.1016/j.ejmech.2014.10.085
[14]	Mao, Z. W.; Zheng, X.; Lin, Y. P.; Hu, C. Y.; Wang, X. L.; Wan, C. P.; Rao, G. X. Bioorg. Med. Chem. Lett. 2016, 26, 3421. doi: 10.1016/j.bmcl.2016.06.055
[15]	Ma, Y.; Zheng, X.; Gao, H.; Wan, C.; Rao, G.; Mao, Z. Molecules 2016, 21, 1684. doi: 10.3390/molecules21121684
[16]	Mao, Z. W.; Jiang, Y.; Rao, G. X. J. Yunnan Univ., Nat. Sci. Ed. 2015, 24, 16. (in Chinese)
	(毛泽伟, 姜圆, 饶高雄, 云南民族大学学报(自然科学版), 2015, 24, 16.)
[17]	Gouthami, P.; Chavan, L. N.; Chegondi, R.; Chandrasekhar, S. J. Org. Chem. 2018, 83, 3325. doi: 10.1021/acs.joc.8b00360
[18]	Huang, C. Y.; Kuo, C. W.; Kavala, V.; Yao, C. F. Eur. J. Org. Chem. 2016, 2016, 2720. doi: 10.1002/ejoc.201600314

Dorsmerunin A的全合成及其抗炎活性研究

Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A

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