Skip to main content
Log in

Four new 6-oxy purine alkaloids from the South China Sea sponge, Haliclona cymaeformis

  • Published:
Journal of Ocean University of China Aims and scope Submit manuscript

Abstract

In this study, the chemical analysis of the marine sponge spieces, Haliclona cymaeformis, collected from the South China Sea was carried out, Two pairs of regioisomers of alkyl substitutional 6-oxy purine alkaloids (1a/1b and 2a/2b) were isolated. All of them possess two structural moieties, a 6-oxy purine nucleus and a pentan-2-one or hexan-2-one alkyl chain. Among them, 1a and 2a are the major N-9-substitutional regioisomers, and 1b and 2b are the minor N-7-substitutional regioisomers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Calderón-Arancibia, J., Espinosa-Bustos, C., Cañete-Molina, Á., Tapia, R. A., Faúndez, M., Torres, M. J., Aguirre, A., Paulino, M., and Salas, C. O., 2015. Synthesis and pharmacophore modelling of 2,6,9-trisubstituted purine derivatives and their potential role as apoptosis-inducing agents in cancer cell lines. Molecules, 20: 6808–6826.

    Article  Google Scholar 

  • Chen, M., Shao, C. L., Fu, X. M., Xu, R. F., Zheng, J. J., Zhao, D. L., She, Z. G., and Wang, C. Y., 2013. Bioactive indole alkaloids and phenyl ether derivatives from a marine-derived Aspergillus sp. fungus. Journal of Natural Products, 76: 547–553.

    Article  Google Scholar 

  • Chen, M., Shao, C. L., Meng, H., She, Z. G., and Wang, C. Y., 2014a. Anti-respiratory syncytial virus prenylated dihydroquinolone derivatives from the gorgonian-derived fungus Aspergillus sp. XS-20090B15. Journal of Natural Products, 77: 2720–2724.

    Article  Google Scholar 

  • Chen, M., Fu, X. M., Kong, C. J., and Wang, C. Y., 2014b. Nucleoside derivatives from the marine-derived fungus Aspergillus versicolor. Natural Products Research, 28: 895–900.

    Article  Google Scholar 

  • Chen, M., Shao, C. L., Fu, X. M., Kong, C. J., She, Z. G., and Wang, C. Y., 2014c. Lumazine peptides penilumamides B-D and the cyclic pentapeptide asperpeptide A from a gorgonian-derived Aspergillus sp. fungus. Journal of Natural Products, 77: 1601–1606.

    Article  Google Scholar 

  • Fromtling, R. A., Galgiani, J. N., Pfaller, M. A., Espinel-Ingroff, A., Bartizal, K. F., Bartlett, M. S., Body, B. A., Frey, C., Hall, G., and Roberts, G. D., 1993. Multicenter evaluation of a broth macrodilution antifungal susceptibility test for yeasts. Antimicrobial Agents and Chemotherapy, 37: 39–45.

    Article  Google Scholar 

  • Gandelman, M., and Jacobsen, E. N., 2005. Highly enantioselective catalytic conjugate addition of N-heterocycles to alpha, beta-unsaturated ketones and imides. Angewandte Chemie International Edition, 44: 2393–2397.

    Article  Google Scholar 

  • Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65: 55–63.

    Article  Google Scholar 

  • Jiang, M. Y., Feng T., and Liu, J. K., 2011. N-Containing compounds of macromycetes. Natural Products Reports, 28: 783–808.

    Article  Google Scholar 

  • Nakao, Y., and Fusetani, N., 2010. 2.10-Marine Invertebrates: Sponges. Elsevier, Oxford, 327–362.

    Google Scholar 

  • Qi, S. H., Zhang, S., Gao, C. H., and Li, Q. X., 2008. Purine and pyrimidine derivatives from the South China Sea gorgonian Subergorgia suberosa. Chemical and Pharmaceutical Bulletin, 56: 993–994.

    Article  Google Scholar 

  • Sun, Z. H., Cai, Y. H., Fan, C. Q., Tang, G. H., Luo, H. B., and Yin, S., 2014. Six new tetraprenylated alkaloids from the South China Sea gorgonian Echinogorgia pseudossapo. Marine Drugs, 12: 672–681.

    Article  Google Scholar 

  • Wu, X. D., Mei, W. L., Shao, C. L., Nicole, J. V., Wang, H., Wang, C. Y., and Dai, H. F., 2011. Studies on the chemical constituents of sponge Haliclona cymaeformis from the South China Sea. Chinese Journal of Marine Drugs, 30: 12–17.

    Google Scholar 

Download references

Acknowledgements

We thank Dr. Changlun Shao, School of Medicine and Pharmacy, Ocean University of China, for collecting the sponge samples. This work was financially supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 16KJB350005), the Yangzhou University Foundation for Fostering Talents in the Science and Technology Innovation (No. 2016CX J052), the National Natural Science Foundation of China (Nos. 81703411, U1606403), and the Taishan Scholars Program, China.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Changyun Wang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chen, M., Wu, X., Shen, N. et al. Four new 6-oxy purine alkaloids from the South China Sea sponge, Haliclona cymaeformis. J. Ocean Univ. China 16, 1183–1186 (2017). https://doi.org/10.1007/s11802-017-3325-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11802-017-3325-5

Key words

Navigation