Chinese Journal of Organic Chemistry >
A New Monoterpene-Phenylpropanoid from Illicium difengpi
Received date: 2022-08-24
Revised date: 2022-10-17
Online published: 2022-11-15
Supported by
National Natural Science Foundation of China(31960091); Guangxi Innovation-driven Development Special Project(Guike AA18118015); Natural Science Foundation of Guangxi Province(2018 GXNSFBA281094); Guilin Innovation Platform and Talent Plant(20210102-3)
Four compounds were isolated from the dichloromethane extract of stem bark of Illicium difengpi by using various column chromatographic methods. Their structures were identified as difengpienol D (1), (E)-3,4-methylenedioxophenyl propenal (2), dihydrocubebin (3) and pestalotiopyrone G (4) respectively by mass spectrometry (MS), infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), etc. and quantum chemical calculation method. Compound 1 was an unusual new compound formed by acyclic monoterpenoid and phenylpropanoid through C—C chain, and was also the first monoterpene-phenylpropanoid isolated from the genus Illicium. It showed weak anti-inflammatory activity.
Desheng Ning , Yuxia Fu , Lianchun Li , Zhiqi Zou , Zhenghong Pan . A New Monoterpene-Phenylpropanoid from Illicium difengpi[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1591 -1595 . DOI: 10.6023/cjoc202208033
| [1] | Sharma, J. N.; Al-Omran, A.; Parvathy, S. S. Inflammopharmacology 2007, 15, 252. |
| [2] | Laskin, J. D.; Heck, D. E.; Laskin, D. L. Trends. Endocrin. Met. 1994, 5, 377. |
| [3] | Bryan, N. S.; Bian, K.; Murad, F. Front. Biosci-Landmrk. 2009, 14, 1. |
| [4] | Kots, A. Y.; Bian, K.; Murad, F. Curr. Med. Chem. 2011, 18, 3299. |
| [5] | MacMicking, J.; Xie, Q. W.; Nathan, C. Annu. Rev. Immumol. 1997, 15, 323. |
| [6] | Wang, X. J.; Zuo, Y. M.; Wang, D. X.; Zhu, Q. Immunol. J. 2015, 31, 435. (in Chinese) |
| [6] | (王筱婧, 左艳敏, 王东兴, 祝倩, 免疫学杂志, 2015, 31, 435.) |
| [7] | Editorial Committee of Flora of China Flora of China, Vol. 30, Science Press, Beijing, 2004, p. 218. (in Chinese) |
| [7] | (中国科学院中国植物志编辑委员会, 中国植物志, 第30卷, 科学出版社, 北京, 2004, p. 218.) |
| [8] | Chines Pharmacopoeia Commission, Pharmacopoeia of the People’s Republic China, Vol. 1, Chines Medical Science Press, Beijing, 2020, p. 128. (in Chinese) |
| [8] | (国家药典委员会, 中华人民共和国中国药典, 第一部, 中国医药科技出版社, 北京, 2020, p. 128.) |
| [9] | Zou, Z. Q.; Ning, D. S.; Li, L. C.; Fu, Y. X.; Pan, Z. H. Guangxi Sci. 2020, 27, 336. (in Chinese) |
| [9] | (邹芷琪, 宁德生, 李连春, 符毓夏, 潘争红, 广西科学, 2020, 27, 336.) |
| [10] | Pan, Z. H.; Ning, D. S.; Huang, S. S.; Cheng, L.; Xia, W. M.; Peng, L. Y.; Li, D. P. Molecules 2016, 21, 607. |
| [11] | Pan, Z. H.; Cheng, L.; Ning, D. S.; Peng, L. Y.; Fu, Y. X.; Li, L. C. Phytochem. Lett. 2019, 30, 210. |
| [12] | Li, L. C.; Ning, D. S.; Fu, Y. X.; Pan, Z. H. Fitoterapia 2021, 153, 104949. |
| [13] | Youn, U. J.; Lee, I. S.; Chen, Q. C.; Na, M. K.; Jung, H. J.; Lee, S. M.; Choi, J. S.; Woo, M. H.; Bae, K.; Min, B. S. Nat. Prod. Sci. 2011, 17, 95. |
| [14] | Yahara, S.; Nishiyori, T.; Kohda, A.; Nohara, T.; Nishioka, I. Chem. Pharm. Bull. 1991, 39, 2024. |
| [15] | Zhang, K.; Ni, W.; Chen, C. X. Nat. Prod. Res. Dev. 1999, 11, 44. (in Chinese) |
| [15] | (张可, 倪伟, 陈昌祥, 天然产物研究与开发, 1999, 11, 44.) |
| [16] | Vidigal, M. C. S.; Cavalheiro, A. J.; Kato, M. J.; Yoshida, M. Phytochemistry 1995, 40, 1259. |
| [17] | Xu, J.; Aly, A. H.; Wray, V.; Proksch, P. Tetrahedron Lett. 2011, 52, 21. |
| [18] | Yan, T.; Yu, X. Y.; Sun, X. D.; Meng, D. L.; Jia, J. M. Fitoterapia 2016, 115, 37. |
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