Skip to main content
Log in

Structural reappraisal of corticatic acids, biologically active linear polyacetylenes, from a marine sponge of the genus Petrosia

  • Original Article
  • Chemistry and Biochemistry
  • Published:
Fisheries Science Aims and scope Submit manuscript

Abstract

Structural reinvestigation of corticatic acid A from a marine sponge, Petrosia sp., resulted in the revision of its structure, which conformed to the structural features of the biosynthetically related linear acetylenes isolated from Petrosia sp. In the process of isolating an authentic corticatic acid A, we isolated three new congeners and determined their structures. We also suggested that the structures of other corticatic acids need revision.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Van Soest RWM, Fusetani N, Andersen RJ (1998) Straight-chain acetylenes as chemotaxonomic markers of the marine Haplosclerida. In: Watanabe Y, Fusetani N (eds) Sponge sciences. Springer, Tokyo, pp 3–30

    Google Scholar 

  2. Hitora Y, Takada K, Okada S, Ise Y, Matsunaga S (2011) (−)-Duryne and its homologues, cytotoxic acetylenes from a marine sponge Petrosia sp. J Nat Prod 74:1262–1267

    Article  PubMed  CAS  Google Scholar 

  3. Minto RE, Blacklock BJ (2008) Biosynthesis and function of polyacetylenes and allied natural products. Prog Lipid Res 47:233–306

    Article  PubMed  CAS  PubMed Central  Google Scholar 

  4. Takayama K, Wang C, Besra GS (2005) Pathway to synthesis and processing of mycolic acid in Mycobacterium tuberculosis. Clin Microbiol Rev 18:81–101

    Article  PubMed  CAS  PubMed Central  Google Scholar 

  5. Wright AE, McConnell OJ, Kohmoto S, Lui MS, Thompson W, Snader KM (1987) Duryne, a new cytotoxic agent from the marine sponge Cribrochalina dura. Tetrahedron Lett 28:1377–1380

    Article  CAS  Google Scholar 

  6. Li H-Y, Matsunaga S, Fusetani N (1994) Corticatic acids A-C, antifungal acetylenic acids from the marine sponge, Petrosia corticata. J Nat Prod 57:1464–1467

    Article  PubMed  CAS  Google Scholar 

  7. Nishimura S, Matsunaga S, Shibazaki M, Suzuki K, Harada N, Naoki H, Fusetani N (2002) Corticatic acids D and E, polyacetylenic geranylgeranyltransferase type 1 inhibitors, from the marine sponge Petrosia corticata. J Nat Prod 65:1353–1356

    Article  PubMed  CAS  Google Scholar 

  8. Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s Method. The absolute configuration of marine terpenoids. J Am Chem Soc 113:4092–4096

    Article  CAS  Google Scholar 

  9. Seo Y, Cho KW, Rho J-R, Shin J (1998) Petrocortynes and petrosiacetylenes, novel polyacetylenes from a sponge of the genus Petrosia. Tetrahedron 54:447–462

    Article  CAS  Google Scholar 

  10. Kim JS, Lim YJ, Im KS, Jung JH, Shim CJ, Lee CO, Hong J, Lee H (1999) Cytotoxic polyacetylenes from the marine sponge Petrosia sp. J Nat Prod 62:554–559

    Article  PubMed  CAS  Google Scholar 

  11. Okamoto C, Nakao Y, Fujita T, Iwashita T, van Soest RW, Fusetani N, Matsunaga S (2007) Cytotoxic C47-polyacetylene carboxylic acids from a marine sponge Petrosia sp. J Nat Prod 70:1816–1819

    Article  PubMed  CAS  Google Scholar 

  12. Amagata T (2010) Misassigned structures: case examples from the past decade. In: Mander L, Liu H-W (eds) Comprehensive natural products II: chemistry and biology, vol 2. Elsevier, Amsterdam, pp 581–621

    Chapter  Google Scholar 

Download references

Acknowledgments

This work was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Chemical Biology of Natural Products” and JSPS KAKENHI Grant Numbers 25252037, 25712024, and 25660163 from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Shigeki Matsunaga.

Electronic supplementary material

Below is the link to the electronic supplementary material.

12562_2014_776_MOESM1_ESM.pdf

Supplementary material 1 (PDF 1081 kb). Electronic Supplementary Material Available: 1H NMR, 2D NMR, and FABMS data for corticatic acids and corticatynol. These materials are published in the online version

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Takada, K., Okada, S. & Matsunaga, S. Structural reappraisal of corticatic acids, biologically active linear polyacetylenes, from a marine sponge of the genus Petrosia . Fish Sci 80, 1057–1064 (2014). https://doi.org/10.1007/s12562-014-0776-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12562-014-0776-0

Keywords

Navigation