Journal of the Korean Magnetic Resonance Society (한국자기공명학회논문지)

Korean Magnetic Resonance Society (한국자기공명학회)
권호 표지
DOI QR코드

DOI QR Code

Structure determination of two new compounds isolated from a marine sponge Haliclona(Gellius) sp.

  • Lee, Kyung (Department of Oceanography, Kunsan National University) ;
  • Kim, Yun Na (Department of Plant & Biomaterials Science, Gyeongsang National University) ;
  • Jeong, Eun Ju (Department of Plant & Biomaterials Science, Gyeongsang National University)
  • Received : 2021.06.09
  • Accepted : 2021.06.19
  • Published : 2021.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Two new sesterterpenes, including a known sesterterpene, were isolated from the marine sponge Haliclona sp. collected in the Gageo island, Korea. One of the new sesterterpenes (1) was an unusual compound possessing a spiroketal moiety and the other (2) represented a four ring-fused skeleton. The planar structure of compound 1 was identical to gombaspiroketals A and B isolated from the marine sponge Clathria gombawuiensis, but the configuration for the two chiral centers was different each other. On the other hand, the skeletal structure of compound 2 was similar to that of phorone A isolated from Phorbas sp. and a compound from C. gombawuiensis, except for one configuration at C-8. However, in comparing the 1H and 13C NMR spectral data, the proton and carbon chemical shifts for the three compounds were almost consistent. The NOESY spectrum revealed that the C-8 configuration of 2 was reversed to that of the two reported compounds. The configuration for compound 2 was supported by quantum mechanical calculation for the carbon chemical shifts and DP4+ probability for the protons and carbons of 2.

Keywords

Acknowledgement

This work was supported by the research invigoration program of 2020 Gyeongsang National University.

References

  1. A. R. Carroll, B. R. Copp, R. A. Davis, P. A. Keyzers, M. R. Prinsep, Nat. Prod. Rep., 37, 175 (2020) https://doi.org/10.1039/c9np00069k
  2. L. M. Stephenson, D. E. Smith, S. P. Current, J. Org. Chem., 37, 4171 (1982)
  3. M. S. Buchanan, A. Edser, G. King, J. Whitmore, R. J. Quinn, J. Nat. Prod., 64, 300 (2001) https://doi.org/10.1021/np0004597
  4. L. V. Manes, S. Naylor, P. Crews, G. J. Bakus, J. Org. Chem., 40, 284 (1985) https://doi.org/10.1021/jo00891a004
  5. J.-R. Rho, B. S. Hwang, C. J. Sim, S. Joung, H.-Y. Lee, H.-J. Kim, Org. Lett., 11, 5590 (2009) https://doi.org/10.1021/ol902223m
  6. J.-R. Rho, B. S. Hwang, S. Joung, M. R. Byun, J. -H. Hong, H.-Y. Lee, Org. Lett., 13, 884 (2011) https://doi.org/10.1021/ol1029386
  7. J.-K. Woo, C.-K. Kim, S.-H. Kim, H. Kim, D.-C. Oh, K-.B. Oh, J. Shin, Org. Lett., 16, 2826 (2014) https://doi.org/10.1021/ol500868s
  8. W. Wang, Y. Lee, T. G. Lee, B. Mun, A. G. Giri, J. Lee, H. Kim, D. H. Hahn, I. Yang, J. Chin, H. Choi, S.-J. Nam, H. Kang, Org. Lett., 14, 4486 (2012) https://doi.org/10.1021/ol3019874
  9. J.-K. Woo, C.-K. Kim, C.-H. Ahn, D.-C. Oh, K.-B. Oh, J. Shin, J. Mat. Prod., 78, 218 (2015)
  10. W. Wang, B. Mun, Y. Lee, M. V. Reddy, Y. Park, J. Lee, H. Kim, D. Hahn, J. Chin, M. Ekins, S.-J. Nam, H. Kang, J. Nat. Prod., 76, 170 (2013) https://doi.org/10.1021/np300573m
  11. R. Forestieri, C. E. Merchant, N. J. de Voogd, T. Matainaho, T. J. Kieffer, R. J. Anderson, Org. Lett., 11, 5166 (2010) https://doi.org/10.1021/ol902066e
  12. W. Hehre, P. Klunzinger, B. Deppmeier, A. Driessen, N. Uchida, M. Hashimoto, E. Fukushi, Y. Takata, J. Nat. Prod., 82, 2299 (2019) https://doi.org/10.1021/acs.jnatprod.9b00603
  13. N. Grimblat, M. M. Zanardi, A. M. Sarotti, J. Org. Chem., 80, 12526 (2015) https://doi.org/10.1021/acs.joc.5b02396