Chinese Journal of Organic Chemistry >
Two New 2,5-Dioxopiperazines from the Marine Sponge Haliclona baeri
Received date: 2022-01-17
Revised date: 2022-02-24
Online published: 2022-03-22
Supported by
National Key Research and Development Plan of China(2019YFD0901905); National Key Research and Development Plan of China(2018YFC0310900); National Natural Science Foundation of China(41876145); National Natural Science Foundation of China(81874292); National Natural Science Foundation of China(21672084); Science and Technology Planning Project of Guangzhou(202102010066); Science and Technology Planning Project of Guangzhou(201704030042)
A series of secondary metabolites had been isolated from the sponge of genus Haliclona, most of which indicated antibacterial, cytotoxic and enzyme activities. However, few literatures about H. baeri had been reported before. In order to search more new bioactive marine natural products from this sponge, H. baeri had been studied systematically. Two new 2,5-dioxopiperazines, haliclines A (1) and B (2), together with five known ones (3~7), were isolated from the marine sponge Haliclona baeri. The structures of these compounds were elucidated by spectroscopic analysis. The absolute configurations of 1 and 2 were established by the method of electronic circular dichroism (ECD) calculation. Compound 1 represented the first example of natural 2,5-dioxopiperazine bearing an L-azetidine-2-carboxylic acid moiety. The antibacterial activities of 1 and 2 were also evaluated.
Key words： sponge; Haliclona baeri; 2,5-dioxopiperazines
Canbin Wang , Yu Lei , Xiaojian Liao , Shihai Xu , Bingxin Zhao . Two New 2,5-Dioxopiperazines from the Marine Sponge Haliclona baeri[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1839 -1842 . DOI: 10.6023/cjoc202201024
| [1] | Yu, S.; Deng, Z.; Proksch, P.; Lin, W. J. Nat. Prod. 2006, 69, 1330. |
| [2] | Cheng, Z. B.; Xiao, H.; Fan, C. Q.; Lu, Y. N.; Zhang, G.; Yin, S. Steroids 2013, 78, 1353. |
| [3] | Jia, R.; Guo, Y. W.; Huang, C. G. Nat. Prod. Res. Dev. 2013, 25, 767. |
| [4] | Casapullo, A.; Pinto, O. C.; Marzocco, S.; Autore, G.; Riccio, R. J. Nat. Prod. 2009, 72, 30103. |
| [5] | Abdjul, D. B.; Yagi, A.; Yamazaki, H.; Kirikoshi, R.; Takahashi, O.; Namikoshi, M.; Uchida, R. Phytochem. Lett. 2018, 26, 130. |
| [6] | Teruya, T.; Kobayashi, K.; Suenaga, K.; Kigoshi, H. J. Nat. Prod. 2006, 69, 135. |
| [7] | Al-Massarani, S. M.; El-Gamal, A. A.; Al-Said, M. S.; Abdel-Kader, M. S.; Ashour, A. E.; Kumar, A.; Fun, H. K. Pharmacogn. Mag. 2016, 12, 114. |
| [8] | Jang, K. H.; Kang, G. W.; Jeon, J. E.; Lim, C.; Lee, H. S.; Sim, C. J.; Shin, J. Org. Lett. 2009, 11, 1713. |
| [9] | Wu, X. D.; Mei, W. L.; Shao, C. L.; Voogd, N. J.; Wang, H.; Wang, C. Y.; Dai, H. F. Chin. J. Mar. Drugs 2011, 30, 12. (in Chinese) |
| [9] | ( 吴旭东, 梅文莉, 邵长伦, Voogd, N. J., 王辉, 王长云, 戴好富, 中国海洋药物, 2011, 30, 12.) |
| [10] | Kong, C. J.; Li, L.; Chen, M.; Cao, F.; Wang, C. Y. Chem. Nat. Compd. 2016, 52, 833. |
| [11] | Trianto, A.; Hermawan, I.; Voogd, N. J.; Tanaka, J. Chem. Pharm. Bull. 2011, 59, 1311. |
| [12] | Molinski, T. F.; Biegelmeyer, R.; Stout, E.P.; Wang, X.; Frot, M. L. J. Nat. Prod. 2013, 76, 374. |
| [13] | Randazzo, A.; Debitus, C.; Gomez-Paloma, L. Tetrahedron 2001, 57, 4443. |
| [14] | Wang, B.; Lee, K. J.; Zhang, S.; Jung, J. H.; Liu, Y. Chem. Nat. Compd. 2009, 45, 137. |
| [15] | Maarisit, W.; Abdjul, D. B.; Yamazaki, H.; Kato, H.; Rotinsulu, H.; Wewengkang, D. S.; Sumilat, D. A.; Kapojos, M. M.; Ukai, K.; Namikoshi, M. Bioorg. Med. Chem. Lett. 2017, 27, 3503. |
| [16] | Zhang, H. W.; Loveridge, S. T.; Tenney, K.; Keyzers, R. A. Nat. Prod. Res. 2016, 30, 1262. |
| [17] | Defant, A.; Mancini, I.; Raspor, L.; Guella, G.; Turk, T.; Sepčić, K. Eur. J. Org. Chem. 2011, 20, 3761. |
| [18] | Bach, B.; Gregson, R. P.; Holland, G. S.; Quinn, R. J.; Reichelt, J. L. Experientia 1978, 34, 688. |
| [19] | Wattanadilok, R.; Sawangwong, P.; Rodrigues, C.; Cidade, H.; Pinto, M.; Pinto, E.; Kijjoa, A. Mar. Drugs. 2007, 5, 40. |
| [20] | Guan, Z. B.; Liang, Y. Q.; Lin, J. L.; Liao, X. J.; Xu, S. H.; Zhao, B. X. Nat. Prod. Res. 2021, 21, 3824. |
| [21] | Liang, Y.-Q.; Liao, X.-J.; Ling, L.; Yang, Y.-T.; Zhao, B.-X.; Xu, S.-H. Chin. J. Org. Chem. 2022, 42, 901. (in Chinese) |
| [21] | ( 梁咏倩, 廖小建, 凌珑, 杨雅婷, 赵冰心, 徐石海, 有机化学, 2022, 42, 901.) |
| [22] | Yang, K.; Xu, S.-H. Chin. J. Org. Chem. 2006, 26, 56. (in Chinese) |
| [22] | 杨凯, 徐石海, 有机化学, 2006, 26, 56.) |
| [23] | Xiao, Y. F.; Xu, J. Y.; Cui, L. Z.; Wang, C. B.; Lei, Y.; Liao, X. J.; Xu, S. H.; Zhao, B. X. Nat. Prod. Res. 2021, DOI: 10.1080/14786419.2021.1941950. |
| [24] | Li, D. H.; Wang, F. P.; Xiao, X.; Zeng, X.; Gu, Q. Q.; Zhu, W. M. Arch. Pharm. Res. 2007, 30, 552. |
| [25] | Cheng, M. J.; Thanda, M. D.; Wu, C. C. Chem. Nat. Compd. 2020, 56, 289. |
| [26] | Liu, C.; Yang, X. Q; Ding, Z. T.; Zhao, L. X.; Cao, Y. R.; Xu, L. H.; Yang, Y. B. Chin. J. Nat. Med. 2011, 9, 78. |
| [27] | Li, Y.; Tang, J. S, Gao, H.; Lin, H. P.; Hong, K.; Yao, X. S. Chin. J. Mar. Drugs 2010, 29, 102. (in Chinese) |
| [27] | ( 李益, 唐金山, 高昊, 林海鹏, 洪葵, 姚新生, 中国海洋药物, 2010, 29, 102.) |
| [28] | Guo, Z. Y.; Huang, Z. J.; Wen, L.; Wan, Q.; Liu, F.; She, Z. G.; Lin, Y. C.; Zhou, S. N. J. Chin. Med. Mater. 2007, 30, 1526. (in Chinese) |
| [28] | ( 郭志勇, 黄忠京, 温露, 万乔, 刘凡, 佘志刚, 林永成, 周世宁, 中药材, 2007, 30, 1526.) |
| [29] | Tao, L.; Wang, G. C.; Huang, X. J.; Ye, W. C. Heterocycles 2013, 87, 1537. |
| [30] | Yue, Z. G.; Zi, J. C.; Zhu, C. G.; Lin, S.; Yang, Y. C.; Shi, J. G. China J. Chin. Mater. Med. 2010, 35, 2852. |
/
| 〈 |
|
〉 |
