Skip to main content
SpringerLink
Log in

Ethyl (2S,4S)-1,4-Anhydro-3-Deoxypentitol-2-Carboxylate, a New Pentitol Analog from the Octocoral Paralemnalia thyrsoides

  • Published:
Chemistry of Natural Compounds Aims and scope

A chemical examination of the cultured octocoral Paralemnalia thyrsoides led to the isolation of a new pentitol analog, ethyl (2S,4S)-1,4-anhydro-3-deoxypentitol-2-carboxylate (1). The structure of 1 was established by spectroscopic analysis.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. D. Daloze, J. C. Braekman, P. Georget, and B. Tursch, Bull. Soc. Chim. Belg., 86, 47 (1977).

    Article  CAS  Google Scholar 

  2. B. F. Bowden, J. C. Coll, and S. J. Mitchell, Aust. J. Chem., 33, 885 (1980).

    Article  CAS  Google Scholar 

  3. R. R. Izac, P. Schneider, M. Swain, and W. Fenical, Tetrahedron Lett., 23, 817 (1982).

    Article  CAS  Google Scholar 

  4. J.-Y. Su, Y.-L. Zhong, J.-Q. Wu, and L.-M. Zeng, Chin. Chem. Lett., 2, 785 (1991).

    CAS  Google Scholar 

  5. J.-Y. Su, Y.-L. Zhong, and L.-M. Zeng, J. Nat. Prod., 56, 288 (1993).

    Article  CAS  Google Scholar 

  6. L. Zeng, Y. Zhong, J. Su, and D. Zhao, Chin. Sci. Bull., 40, 213 (1995).

    Article  CAS  Google Scholar 

  7. H.-C. Huang, C.-H. Chao, J.-H. Liao, M. Y. Chiang, C.-F. Dai, Y.-C. Wu, and J.-H. Sheu, Tetrahedron Lett., 46, 7711 (2005).

    Article  CAS  Google Scholar 

  8. H.-C. Huang, Z.-H. Wen, C.-H. Chao, A. F. Ahmed, M. Y. Chiang, Y.-H. Kuo, C.-H. Hsu, and J.-H. Sheu, Tetrahedron Lett., 47, 8751 (2006).

    Article  CAS  Google Scholar 

  9. H.-C. Huang, C.-H. Chao, J.-H. Su, C.-H. Hsu, S.-P. Chen, Y.-H. Kuo, and J.-H. Sheu, Chem. Pharm. Bull., 55, 876 (2007).

    Article  CAS  Google Scholar 

  10. A. Bishara, D. Yeffet, M. Sisso, G. Shmul, M. Schleyer, Y. Benayahu, A. Rudi, and Y. Kashman, J. Nat. Prod., 71, 375 (2008).

    Article  CAS  PubMed  Google Scholar 

  11. G.-H. Wang, H.-C. Huang, J.-H. Su, Y.-C. Wu, and J.-H. Sheu, Chem. Pharm. Bull., 58, 30 (2010).

    Article  CAS  Google Scholar 

  12. S.-Y. Cheng, E.-H. Lin, J.-S. Huang, Z.-H. Wen, and C.-Y. Duh, Chem. Pharm. Bull., 58, 381 (2010).

    Article  CAS  Google Scholar 

  13. C.-Y. Huang, J.-H. Su, B.-W. Chen, Z.-H. Wen, C.-H. Hsu, C.-F. Dai, J.-H. Sheu, and P.-J. Sung, Mar. Drugs, 9, 1543 (2011).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. S.-K. Wang, Y.-S. Lee, and C.-Y. Duh, Mar. Drugs, 10, 1528 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Y.-J. Tseng, Y.-S. Lee, S.-K. Wang, J.-H. Sheu, and C.-Y. Duh, Mar. Drugs, 11, 2501 (2013).

    Article  PubMed  PubMed Central  Google Scholar 

  16. Y.-S. Lee, T.-H. Duh, S.-S. Siao, R.-C. Chang, S.-K. Wang, and C.-Y. Duh, Mar. Drugs, 15, 392 (2017).

    Article  PubMed  PubMed Central  Google Scholar 

  17. Z.-J. Zhang, W.-F. Chen, B.-R. Peng, Z.-H. Wen, and P.-J. Sung, Nat. Prod. Commun., 13, 5 (2018).

    Google Scholar 

  18. X. Han, Q. Wang, X. Luo, X. Tang, Z. Wang, D. Zhang, S. Cao, P. Lin, and G. Li, Org. Lett., 24, 11 (2022).

    Article  CAS  PubMed  Google Scholar 

  19. R. Alen, Carbohydr. Res., 144, 163 (1985).

    Article  CAS  Google Scholar 

  20. N. L. Allinger, J. Am. Chem. Soc., 99, 8127 (1977).

    Article  CAS  Google Scholar 

  21. C.-F. Dai, Corals of Taiwan, Vol. 2, Octocorallia, Owl Publishing House Co., Ltd., Taipei, 2022, p. 267.

  22. C.-F. Dai, Octocorallia Fauna of Taiwan, Ocean Center, National Taiwan University, Taipei, 2021, pp. 436–437.

    Google Scholar 

  23. C.-F. Dai and C.-H. Chin, Octocorallia Fauna of Kenting National Park, Kenting National Park Headquarters, Pingtung, 2019, pp. 344–345.

Download references

Acknowledgment

The authors are grateful to Hsiao-Ching Yu and Chao-Lien Ho, the High Valued Instrument Center, National Sun Yat-sen University, for obtaining the mass (MS 006500) and NMR (NMR 001100) spectra (NSTC 112-2740-M-110-002). This work was mainly funded by grants from the National Museum of Marine Biology and Aquarium; the National Science and Technology Council (Grant Nos. MOST 107-2320-B-291-001-MY3, 109-2320-B-291-001-MY3, 110-2320-B-182A-011, and 111-2320-B-291-001); and Chang Gung Memorial Hospital (CMRPG3J1001~3), Taiwan, awarded to Chun-Yu Chen, Tsong-Long Hwang, and Ping-Jyun Sung.

In addition, Gia-Hung Phan and Chun-Yu Chen contributed equally to this work.

Author information

Authors and Affiliations

  1. Graduate Institute of Marine Biology, National Dong Hwa University, 944401, Pingtung, Taiwan

    Gia-Hung Phan

  2. National Museum of Marine Biology and Aquarium, 944401, Pingtung, Taiwan

    Gia-Hung Phan & Ping-Jyun Sung

  3. Department of Anesthesiology, Chang Gung Memorial Hospital, 333008, Taoyuan, Taiwan

    Chun-Yu Chen & Tsong-Long Hwang

  4. Graduate Institute of Clinical Medical Sciences, College of Medicine, Chang Gung University, 333323, Taoyuan, Taiwan

    Chun-Yu Chen

  5. Department of Pharmacy, School of Pharmaceutical Sciences, National Yang Ming Chiao Tung University, 112304, Taipei, Taiwan

    Jih-Jung Chen

  6. Department of Marine Biotechnology and Resources, National Sun Yat-sen University, 804201, Kaohsiung, Taiwan

    Zhi-Hong Wen & Ping-Jyun Sung

  7. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, 333323, Taoyuan, Taiwan

    Tsong-Long Hwang

  8. Research Center for Chinese Herbal Medicine, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, 333324, Taoyuan, Taiwan

    Tsong-Long Hwang

  9. Department of Chemical Engineering, Ming Chi University of Technology, 243303, New Taipei City, Taiwan

    Tsong-Long Hwang

  10. School of Chinese Medicine, College of Chinese Medicine, China Medical University, 404328, Taichung, Taiwan

    Yu-Chi Tsai

  11. Chinese Medicine Research and Development Center, China Medical University Hospital, 404394, Taichung, Taiwan

    Ping-Jyun Sung

Authors
  1. Gia-Hung Phan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chun-Yu Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jih-Jung Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhi-Hong Wen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tsong-Long Hwang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yu-Chi Tsai
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ping-Jyun Sung
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Yu-Chi Tsai or Ping-Jyun Sung.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2023, pp. 355–357.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Phan, GH., Chen, CY., Chen, JJ. et al. Ethyl (2S,4S)-1,4-Anhydro-3-Deoxypentitol-2-Carboxylate, a New Pentitol Analog from the Octocoral Paralemnalia thyrsoides. Chem Nat Compd 59, 417–419 (2023). https://doi.org/10.1007/s10600-023-04013-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-023-04013-8

Keywords

Search

Navigation