海绵Spongia sp.中一个新的D环为吡啶环的降海绵烷型二萜
收稿日期: 2021-09-22
修回日期: 2021-10-19
网络出版日期: 2021-11-09
基金资助
国家重点研发计划(2019YFD0901905); 国家重点研发计划(2018YFC0310900); 国家自然科学基金(41876145); 国家自然科学基金(81874292); 国家自然科学基金(21672084); 广州市科技计划(202102010066); 广州市科技计划(201704030042)
A New Dinorspongian Diterpene with Pyridyl D-Ring from the Marine Sponge Spongia sp.
Received date: 2021-09-22
Revised date: 2021-10-19
Online published: 2021-11-09
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)
梁咏倩 , 廖小建 , 凌珑 , 杨雅婷 , 赵冰心 , 徐石海 . 海绵Spongia sp.中一个新的D环为吡啶环的降海绵烷型二萜[J]. 有机化学, 2022 , 42(3) : 901 -904 . DOI: 10.6023/cjoc202109024
Chemical investigation of the marine sponge Spongia sp. led to a new dinorspongian diterpene dinorspongiapyridine (1) together with four known compounds 2~5. Compound 1 was the first instance of 3,4-seco-3,19-dinorspongian diterpene bearing a rare pyridyl D-ring system. The structure with absolute configuration of 1 was elucidated by the methods of NMR and X-ray diffraction. In addition, the cytotoxic activities against several cancer cell lines of 1 were evaluated. The plausible biogenetic pathway of 1 was also proposed.
Key words: sponge; Spongia; dinorspongian diterpene; pyridyl ring
| [1] | (a) Liu, L.; Zheng, Y.-Y.; Shao, C.-L.; Wang, C.-Y. Mar. Life Sci. Technol. 2019, 1, 60. |
| [1] | (b) Peng, X.-Y; Wu, J.-T; Shao, C.-L.; Li, Z.-Y.; Chen, M.; Wang, C.-Y. Mar. Life Sci. Technol. 2021, 3, 363. |
| [2] | (a) Gunasekera, S. P.; Schmitz, F. J. J. Org. Chem. 1991, 56, 1250. |
| [2] | (b) Kernan, M. R.; Cambie, R. C.; Bergquist, P. R. J. Nat. Prod. 1990, 53, 724. |
| [2] | (c) Dilip De Silva, E.; Morris, S. A.; Miao, S.; Dumdei, E.; Andersen, R. J. J. Nat. Prod. 1991, 54, 993. |
| [3] | (a) El-Desoky, A. H.; Kato, H.; Angkouw, E. D.; Mangindaan, R. E. P.; de Voogd, N. J.; Tsukamoto, S. J. Nat. Prod. 2016, 79, 1922. |
| [3] | (b) Han, G.-Y.; Sun, D.-Y.; Liang, L.-F.; Yao, L.-G.; Chen, K.-X.; Guo, Y.-W. Fitoterapia 2018, 127, 159. |
| [3] | (c) Ramirez, M. C. A.; Williams, D. E.; Gubiani, J. R.; Parra, L. L. L.; Santos, M. F. C.; Ferreira, D. D.; Mesquita, J. T.; Tempone, A. G.; Ferreira, A. G.; Padula, A. G.; Hajdu, E.; Andersen, R. J.; Berlinck, R. G. S. J. Nat. Prod. 2017, 80, 720. |
| [4] | Miyamoto, T.; Sakamoto, K.; Arao, K.; Komori, T.; Higuchi, R.; Sasaki, T. Tetrahedron 1996, 52, 8187. |
| [5] | Bobzin, S. C.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 225. |
| [6] | Keyzers, R.; Northcote, P.; Zubkov, O. Eur. J. Org. Chem. 2004, 2004, 419. |
| [7] | (a) Parrish, S. M.; Yoshida, W. Y.; Kondratyuk, T. P.; Park, E.; Pezzuto, J. M.; Kelly, M.; Williams, P. G. J. Nat. Prod. 2014, 77, 1644. |
| [7] | (b) De Marino, S.; Iorizzi, M.; Zollo, F.; Debitus, C.; Menou, J.; Ospina, L. F.; Alcaraz, M. J.; Payá, M. J. Nat. Prod. 2000, 63, 322. |
| [8] | (a) Liang, Y.-Q.; Liao, X.-J.; Lin, J.-L.; Xu, W.; Chen, G.-D.; Zhao, B.-X.; Xu, S. H. Tetrahedron 2019, 75, 3802. |
| [8] | (b) Liang, Y.-Q.; Liao, X.-J.; Zhao, B.-X.; Xu, S. H. Org. Chem. Front. 2020, 20, 3253. |
| [9] | Li, X.; Song, S.-J.; Pu, S.-J. Dong, T.; Lin, H.-W. Chin. J. Mar. Drugs 2009, 28, 21. (in Chinese) |
| [9] | (厉学, 宋少江, 朴淑娟, 董涛, 林厚文, 中国海洋药物, 2009, 28, 21.) |
| [10] | Liu, Y.; Ouyang, F.; Yu, H.-Y.; Li, L.; Wang, N.-L.; Yao, X.-S. Chin. J. Med. Chem. 2009, 19, 273. (in Chinese) |
| [10] | (刘远, 欧阳富, 于海洋, 李利, 王乃利, 姚新生, 中国药物化学杂志, 2009, 19, 273.) |
| [11] | Wang, R.-P.; Lin, H.-W.; Li, L.-Z.; Gao, P.-Y.; Xu, Y.; Song, S.-J. Biochem. Syst. Ecol. 2012, 43, 210. |
| [12] | Yuan, P.-L.; Wang, X.-P.; Chen, K.-X.; Li, Y.-M.; Jia, Q. Chin. Tradit. Pat. Med. 2016, 38, 104. (in Chinese) |
| [12] | (袁谱龙, 王雪萍, 陈凯先, 李医明, 贾琦, 中成药, 2016, 38, 104.) |
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