Dihydrocystodytine G, a new tetracyclic aromatic alkaloid isolated from a specimen of the marine tunicate Cystodytes sp. collected off Rufisque - Senegal

  • Mohamet Diop Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP: 5005, Dakar Fann, Sénégal
  • Abou Moussa Sow Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP: 5005, Dakar Fann, Sénégal
  • Mouhamadou Fofana Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP: 5005, Dakar Fann, Sénégal
  • Bédié Mbow Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP: 5005, Dakar Fann, Sénégal
  • Dior Samb Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP: 5005, Dakar Fann, Sénégal
Keywords: tunicate, Cystodytes sp., pyridoacridine alkaloids, marine metabolites

Abstract

Our recent research on the brown tunic of Cystodytes sp. has led to the isolation of four tetracyclic aromatic alkaloids. Among these compounds, cystodytin B (1) and cystodytin G (2) have already been well characterized. Cystodytin L (3) was also found, a compound we had previously identified and published. Above all, the study highlighted the discovery of a new alkaloid: Dihydrocystodytine G (4).

The chemical structures of these compounds were elucidated by combining the determination of specific rotatory power ([α]D), various spectroscopic techniques (1D and 2D NMR), mass spectrometry and comparison with literature data. In addition, the absolute C-12 configuration of compounds 2 to 4 was established as R using electron circular dichroism (ECD) spectroscopy and time-dependent DFT (Density Functional Theory) calculations. 

In this article, we describe the isolation and structural elucidation of this new compound.

References

Cadelis, M. M., & Copp, B. R. (2023). Marine pyridoacridine, pyridoacridone and pyrroloacridine alkaloids. In The alkaloids (Vol. 90, pp. 97-157). Elsevier. https://doi.org/10.1016/bs.alkal.2023.06.001

Kobayashi, J., Cheng, J.-F., Wälchli, M. R., Nakamura, H., Hirata, Y., Sasaki, T., & Ohizumi, Y. (1988). Cystodytins A, B, and C, novel tetracyclic aromatic alkaloids with potent antineoplastic activity from the Okinawan tunicate Cystodytes dellechiajei. The Journal of Organic Chemistry, 53(8), 1800-1804. https://doi.org/10.1021/jo00243a039

Barnes, E. C., Said, N. A. B. M., Williams, E. D., Hooper, J. N. A., & Davis, R. A. (2010). Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge, Ecionemia geodides. Tetrahedron, 66(1), 283-287. https://doi.org/10.1016/j.tet.2009.10.109

Li, T., Ding, T., & Li, J. (2019). Medicinal purposes: Bioactive metabolites from marine-derived organisms. Mini-Reviews in Medicinal Chemistry, 19(2), 138-164. https://doi.org/10.2174/1389557517666170927113143

Agrawal, M. S., & Bowden, B. F. (2007). Nordehydrocyclodercitin, a hexacyclic pyridoacridine alkaloid from the marine ascidian, Aplidium sp. Natural Product Research, 21(9), 782-786. https://doi.org/10.1080/14786410601132212

Bontemps, N., Bry, D., López-Legentil, S., Simon-Levert, A., Long, C., & Banaigs, B. (2010). Structures and antimicrobial activities of pyridoacridine alkaloids isolated from different chromotypes of the ascidian Cystodytes violatinctus. Journal of Natural Products, 73(6), 1044-1048. https://doi.org/10.1021/np900751k

Ibrahim, S. R. M., & Mohamed, G. A. (2016). Marine pyridoacridine alkaloids: Biosynthesis and biological activities. Chemistry & Biodiversity, 13(1), 37-47. https://doi.org/10.1002/cbdv.201400434

Kumar, A., Bhagat, K. K., Singh, A. K., Singh, H., Angre, T., Verma, A., Khalilullah, H., Jaremko, M., Emwas, A.-H., & Kumar, P. (2023). Medicinal chemistry perspective of pyrido[2,3-d]pyrimidines as anticancer agents. RSC Advances, 13(10), 6872-6908. https://doi.org/10.1039/D3RA00056G

Yasuhara-Bell, J., & Lu, Y. (2010). Marine compounds and their antiviral activities. Antiviral Research, 86(3), 231-240. https://doi.org/10.1016/j.antiviral.2010.03.009

Copp, B. R., Kayser, O., Brun, R., & Kiderlen, A. F. (2003). Antiparasitic activity of marine pyridoacridone alkaloids related to the ascididemins. Planta Medica, 69(6), 527-531. https://doi.org/10.1055/s-2003-40640

Diop, M., Sow, A. M., Fofana, M., Mbow, B., & Samb, D. (2023). Cystodytin L, a pyridoacridine alkaloid from the Senegalese tunicate Cystodytes sp. Earthline Journal of Chemical Sciences, 9(2), 177-188. https://doi.org/10.34198/ejcs.9223.177188

Kobayashi, J., Cheng, J.-F., Wälchli, M. R., Nakamura, H., Hirata, Y., Sasaki, T., & Ohizumi, Y. (1988). Cystodytins A, B, and C, novel tetracyclic aromatic alkaloids with potent antineoplastic activity from the Okinawan tunicate Cystodytes dellechiajei. The Journal of Organic Chemistry, 53(8), 1800-1804. https://doi.org/10.1021/jo00243a039

Kobayashi, J., Tsuda, M., Tanabe, A., Ishibashi, M., Cheng, J.-F., Yamamura, S., & Sasaki, T. (1991). Cystodytins D-I, new cytotoxic tetracyclic aromatic alkaloids from the Okinawan marine tunicate Cystodytes dellechiajei. Journal of Natural Products, 54(6), 1634-1638. https://doi.org/10.1021/np50078a022

Jiang, D., Chen, Y., & Wang, S. (2022). Total synthesis of marine alkaloids cystodytins A-K. The Journal of Organic Chemistry, 87(16), 11063-11072. https://doi.org/10.1021/acs.joc.2c01317

Published
2025-08-21
How to Cite
Diop, M., Sow, A. M., Fofana, M., Mbow, B., & Samb, D. (2025). Dihydrocystodytine G, a new tetracyclic aromatic alkaloid isolated from a specimen of the marine tunicate Cystodytes sp. collected off Rufisque - Senegal. Earthline Journal of Chemical Sciences, 12(3), 359-366. https://doi.org/10.34198/ejcs.12325.359366
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Articles