研究简报

海绵Spongia sp.中一个新的D环为吡啶环的降海绵烷型二萜

  • 梁咏倩 ,
  • 廖小建 ,
  • 凌珑 ,
  • 杨雅婷 ,
  • 赵冰心 ,
  • 徐石海
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  • a 暨南大学化学与材料学院 广州 510632
    b 广东药科大学药学院 广州 510006
† 共同第一作者

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.

  • Yongqian Liang ,
  • Xiaojian Liao ,
  • Long Ling ,
  • Yating Yang ,
  • Bingxin Zhao ,
  • Shihai Xu
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  • a College of Chemistry and Materials Science, Jinan University, Guangzhou 510632
    b College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;

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)

摘要

在对一种Spongia属海绵的化学成分研究中, 分离得到一个新的降海绵烷型二萜dinorspongiapyridine (1)和四个已知化合物2~5. 通过核磁共振波谱、单晶X-ray衍射以及对比文献的方法, 确定了这些化合物的结构及其绝对构型. 化合物1是首次发现的D环为吡啶环的3,4-裂环-3,19-双降海绵烷型二萜类化合物, 并对其细胞毒活性进行了测试. 此外, 对化合物1的生物合成途径也进行了探讨.

本文引用格式

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

Abstract

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.

参考文献

[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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