Cystodytin L, a Pyridoacridine Alkaloid from the Senegalese Tunicate Cystodytes sp.

  • 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., cystodytin, pyridoacridine alkaloids, marine metabolites

Abstract

Chemical investigation of the brown-colored tunicate Cystodytes sp. yielded six pyridoacridine alkaloids, including the known metabolites arnoamine C (1), styelsamine C (2), cystodytin B (3), E (4) and G (5) and the new compound, cystodytin L (6).

Their chemical structures were established on the basis of combination of [α]D, physical and spectroscopic methods 1D and 2D NMR, in addition to mass spectrometry and comparison with literature data. The absolute configuration of C-12 in compounds 4-6 was identified as R by electronic circular dichroism (ECD) spectroscopy coupled with time-dependent density functional theory calculations.

References

Bregmann, W., & Feeney, R.J. (1951). Contribution to the study of marine products. J. Org. Chem., 16(6), 981-987.

Hu, Y., Chen, J., Hu, G., Yu, J., Zhu, X., Lin, Y., Chen, S., & Yuan, J. (2015). Statistical research on the bioactivity of new marine natural products discovered during the 28 years from 1985 to 2012. Mar. Drugs, 13(1), 202-221. https://doi.org/10.3390/md13010202

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

Ibrahim, S.R.M., Mohamed, G.A., Elkhayat, E.S., Fouad, M.A., & Proksch, P. (2013). Sagitol C, a new cytotoxic pyridoacridine alkaloid from the sponge Oceanapia sp. Bull. Fac. Pharm. Cairo Univ., 51, 229-232. https://doi.org/10.1016/j.bfopcu.2013.05.004

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

Plubrukarn, A., & Davidson, B.S. (1998). Arnoamines A and B, new cytotoxic pentacyclic pyridoacridine alkaloids from the ascidian Cystodytes sp. J. Org. Chem., 63(5), 1657-1659. https://doi.org/10.1021/jo9719721

Cimino, G., Crispino, A., De Rosa, S., De Stefano, S., Gavagnin, M., & Sodano, G. (1987). Studies on the structure of calliactine, the zoochrome of the sea anemone Calliactis parasitica. Tetrahedron, 43(17), 4023-4030. https://doi.org/10.1016/s0040-4020(01)81685-9

Koren-Goldshlager, G., Aknin, M., Gaydou, E.M., & Kashman, Y. (1998). Three new alkaloids from the marine tunicate Cystodytes violatinctus. J. Org. Chem., 63(14), 4601-4603. https://doi.org/10.1021/jo9721453

Cooray, N.M., Scheuer, P.J., Parkanyi, L., & Clardy, J. (1988). Shermilamine A: A pentacyclic alkaloid from a tunicate. J. Org. Chem., 53(19), 4619-4620. https://doi.org/10.1021/jo00254a049

Carroll, A.R., & Scheuer, P.J. (1990). Kuanoniamines A, B, C, and D: pentacyclic alkaloids from a tunicate and its prosobranch mollusk predator Chelynotus semperi. J. Org. Chem., 55(14), 4426-4431. https://doi.org/10.1021/jo00301a040

Ding, Q., Chichak, K., & Lown, J.W. (1999). Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Curr. Med. Chem., 6(1), 1-27. https://doi.org/10.2174/0929867306666220207205410

Marshall, K.M., & Barrows, L.R. (2004). Biological activities of pyridoacridines. Nat. Prod. Rep., 21(6), 731-751. https://doi.org/10.1039/b401662a

Bontemps, N., Bry, D., Lopez-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 dellechiajei. J. Nat. Prod., 73(6), 1044-1048. https://doi.org/10.1021/np900751k

McCarthy, P.J., Pitts, T.P., Gunawardana, G.P., Kelly-Borges, M., & Pomponi, S.A. (1992). Antifungal activity of meridine, a natural product from the marine sponge Corticium sp. J. Nat. Prod., 55(11), 1664-1668. https://doi.org/10.1021/np50089a016

Lindsay, B.S., Pearce, A.N., & Copp, B.R. (1997). Efficient and convenient pyridine ring-E formation of the cytotoxic marine alkaloid ascididemin and related analogues. Synth. Commun., 27(15), 2587-2592. https://doi.org/10.1080/00397919708004128

Luedtke, N.W., Hwang, J.S., Glazer, E.C., Gut, D., Kol, M., & Tor, Y. (2002). Eilatin Ru(II) complexes display anti-HIV activity and enantiomeric diversity in the binding of RNA. ChemBioChem, 3(8), 766-771. https://doi.org/10.1002/1439-7633(20020802)3:8%3C766::aid-cbic766%3E3.0.co;2-x

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

McDonald, L.A., Eldredge, G.S., Barrows, L.R., & Ireland, C.M. (1994). Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem., 37(22), 3819-3827. https://doi.org/10.1021/jm00048a017

Kobayashi, J., Cheng, J-F., Walchli, 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. J. Org. Chim., 53(8), 1800-1804. https://doi.org/10.1021/jo00243a038

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. J. Nat. Prod., 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. J. Org. Chem., 87(16), 11063-11072. https://doi.org/10.1021/acs.joc.2c01317

Published
2022-11-27
How to Cite
Diop, M., Sow, A. M., Fofana, M., Mbow, B., & Samb, D. (2022). 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
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Articles

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