Skip to main content

Chemical and Biological Aspects of Water-Soluble Heterocyclic Marine Natural Products

  • Chapter
  • First Online:
Marine Natural Products

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 58))

Abstract

Water-soluble marine natural products are interesting as they generally do not penetrate into the cells but exhibit biological activities through cell surface receptors, ion channels, and glycans. Some molecules, however, interact with cell membrane and disrupt it. In this review, discovery, structures, and biological activities of water-soluble marine natural heterocyclic molecules are summarized with special emphasis on their biological activity and functions.

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

Access this chapter

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 349.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 449.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 449.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

References

  1. Shimizu Y (1985) J Nat Prod 48:223–235

    Article  CAS  PubMed  Google Scholar 

  2. Sakai R, Swanson GT (2014) Nat Prod Rep 31:273–309

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Olivera BM, Cruz LJ, Yoshikami D (1999) Curr Opin Neurobiol 9:772–777

    Article  CAS  PubMed  Google Scholar 

  4. Fritz L, Quilliam MA, Wright JL, Beale AM, Work TM (1992) J Phycol 28:439–442

    Article  Google Scholar 

  5. Stathakis CI, Yioti EG, Gallos JK (2012) Eur J Org Chem 2012:4661–4673

    Article  CAS  Google Scholar 

  6. Stonik VA, Stonik IV (2020) Molecules 25:3049

    Article  CAS  PubMed Central  Google Scholar 

  7. Toyota M, Spencer D, Sawai-Toyota S, Jiaqi W, Zhang T, Koo AJ, Howe GA, Gilroy S (2018) Science 361:1112–1115

    Article  CAS  PubMed  Google Scholar 

  8. Sakai R, Minato S, Koike K, Koike K, Jimbo M, Kamiya H (2005) Cell Tissue Res 322:491–502

    Article  CAS  PubMed  Google Scholar 

  9. Chekan JR, McKinnie SM, Moore ML, Poplawski SG, Michael TP, Moore BS (2019) Angew Chem 131:8542–8545

    Google Scholar 

  10. Brunson JK, McKinnie SM, Chekan JR, McCrow JP, Miles ZD, Bertrand EM, Bielinski VA, Luhavaya H, Oborník M, Smith GJ (2018) Science 361:1356–1358

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Maeno Y, Kotaki Y, Terada R, Cho Y, Konoki K, Yotsu-Yamashita M (2018) Sci Rep 8:1–10

    Google Scholar 

  12. Lichtenthaler HK (2010) The non-mevalonate doxp/mep (deoxyxylulose 5-phosphate/methylerythritol 4-phosphate) pathway of chloroplast isoprenoid and pigment biosynthesis. In the chloroplast. Springer, Berlin, pp 95–118

    Google Scholar 

  13. Sakai R, Kamiya H, Murata M, Shimamoto K (1997) J Am Chem Soc 119:4112–4116

    Article  CAS  Google Scholar 

  14. Sakai R, Suzuki K, Shimamoto K, Kamiya H (2004) J Org Chem 69:1180–1185

    Article  CAS  PubMed  Google Scholar 

  15. Sakai R, Kamiya H (2006) J Antibiot 59:507–511

    Article  CAS  Google Scholar 

  16. IJzendoorn DR, Botman PN, Blaauw RH (2006) Org Lett 8:239–242

    Article  CAS  PubMed  Google Scholar 

  17. Sakai M, Ishikawa Y, Takamizawa S, Oikawa M (2013) Tetrahedron Lett 54:5911–5912

    Article  CAS  Google Scholar 

  18. Tanaka K, Sakai M, Takamizawa S, Oikawa M (2015) Chem Lett 44:253–255

    Article  CAS  Google Scholar 

  19. Ridley CP, Faulkner DJ, Haygood MG (2005) Appl Environ Microbiol 71:7366–7375

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Sakai R, Yoshida K, Kimura A, Koike K, Jimbo M, Koike K, Kobiyama A, Kamiya H (2008) Chembiochem 9:543–551

    Article  CAS  PubMed  Google Scholar 

  21. Donia MS, Fricke WF, Partensky F, Cox J, Elshahawi SI, White JR, Phillippy AM, Schatz MC, Piel J, Haygood MG (2011) Proc Nat Acad Sci 108:E1423–E1432

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Sakai R, Swanson GT, Shimamoto K, Green T, Contractor A, Ghetti A, Tamura-Horikawa Y, Oiwa C, Kamiya H (2001) J Pharmacol Exp Ther 296:650–658

    CAS  PubMed  Google Scholar 

  23. Swanson GT, Green T, Sakai R, Contractor A, Che W, Kamiya H, Heinemann SF (2002) Neuron 34:589–598

    Article  CAS  PubMed  Google Scholar 

  24. Frydenvang K, Lash LL, Naur P, Postila PA, Pickering DS, Smith CM, Gajhede M, Sasaki M, Sakai R, Pentikaïnen OT (2009) J Biol Chem 284:14219–14229

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Møllerud S, Frydenvang K, Pickering DS, Kastrup JS (2017) Neuropharmacology 112:16–28

    Article  PubMed  CAS  Google Scholar 

  26. Armstrong N, Gouaux E (2000) Neuron 28:165–181

    Article  CAS  PubMed  Google Scholar 

  27. Birdsey-Benson A, Gill A, Henderson LP, Madden DR (2010) J Neurosci 30:1463–1470

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Qiu C-S, Lash-Van Wyhe L, Sasaki M, Sakai R, Swanson GT, Gereau IV RW (2011) Pain 152:1052–1060

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Oikawa M, Ikoma M, Sasaki M, Gill MB, Swanson GT, Shimamoto K, Sakai R (2010) Bioorg Med Chem 18:3795–3804

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Oikawa M, Kasori Y, Katayama L, Murakami E, Oikawa Y, Ishikawa Y (2013) Synthesis 45:3106–3117

    Article  CAS  Google Scholar 

  31. Chiba M, Fujimoto C, Sakai R, Oikawa M (2015) Bioorg Med Chem Lett 25:1869–1871

    Article  CAS  PubMed  Google Scholar 

  32. Gill M, Frausto S, Ikoma M, Sasaki M, Oikawa M, Sakai R, Swanson GT (2010) Br J Pharmacol 160:1417–1429

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Juknaite L, Sugamata Y, Tokiwa K, Ishikawa Y, Takamizawa S, Eng A, Sakai R, Pickering DS, Frydenvang K, Swanson GT (2013) J Med Chem 56:2283–2293

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Sakai R, Matsubara H, Shimamoto K, Jimbo M, Kamiya H, Namikoshi M (2003) J Nat Prod 66:784–787

    Article  CAS  PubMed  Google Scholar 

  35. Evans SV, Shing TK, Aplin RT, Fellows LE, Fleet GW (1985) Phytochemistry 24:2593–2596

    Article  CAS  Google Scholar 

  36. Mannaioni G, Alesiani M, Carlà V, Natalini B, Marinozzi M, Pellicciari R, Moroni F (1994) Eur J Pharmacol 251:201–207

    Article  CAS  PubMed  Google Scholar 

  37. Daly J (2007) Cell Mol Life Sci 64:2153–2169

    Article  CAS  PubMed  Google Scholar 

  38. Sakurada T, Gill MB, Frausto S, Copits B, Noguchi K, Shimamoto K, Swanson GT, Sakai R (2010) J Med Chem 53:6089–6099

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Yu L, Coelho JE, Zhang X, Fu Y, Tillman A, Karaoz U, Fredholm BB, Weng Z, Chen J-F (2009) Physiol Genomics 37:199–210

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Sakai R, Jares-Erijman EA, Manzanares I, Silva Elipe MV, Rinehart KL (1996) J Am Chem Soc 118:9017–9023

    Article  CAS  Google Scholar 

  41. Schmidt EW, Donia MS (2010) Curr Opin Biotechnol 21:827–833

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Taylor SW, Kammerer B, Bayer E (1997) Chem Rev 97:333–346

    Article  CAS  PubMed  Google Scholar 

  43. Uchimasu H, Matsumura K, Tsuda M, Kumagai K, Akakabe M, Fujita MJ, Sakai R (2016) Tetrahedron 72:7185–7193

    Article  CAS  Google Scholar 

  44. Jinnai D, Sawai A, Mori A (1966) Nature 212:617–617

    Article  CAS  PubMed  Google Scholar 

  45. Godecke T, Lankin DC, Nikolic D, Chen S-N, van Breemen RB, Farnsworth NR, Pauli GF (2009) J Nat Prod 72:433–437

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  46. Van Wagoner RM, Jompa J, Tahir A, Ireland CM (1999) J Nat Prod 62:794–797

    Article  PubMed  Google Scholar 

  47. Davis RA, Duffy S, Avery VM, Camp D, Hooper JN, Quinn RJ (2010) Tetrahedron Lett 51:583–585

    Article  CAS  Google Scholar 

  48. Akizawa T, Yamazaki K, Yasuhara T, Nakajima T, Roseghini M, Erspamer GF, Erspamer V (1982) Biomed Res 3:232–234

    Article  CAS  Google Scholar 

  49. Cesar LM, Mendes MA, Tormena CF, Marques MR, De Souza BM, Saidemberg DM, Bittencourt JC, Palma MS (2005) Toxicon 46:786–796

    Article  CAS  PubMed  Google Scholar 

  50. Wang W, Takahashi O, Oda T, Nakazawa T, Ukai K, Mangindaan RE, Rotinsulu H, Wewengkang DS, Kobayashi H, Tsukamoto S (2009) Tetrahedron 65:9598–9603

    Article  CAS  Google Scholar 

  51. Jiang C-S, Müller WE, Schröder HC, Guo Y-W (2012) Chem Rev 112:2179–2207

    Article  CAS  PubMed  Google Scholar 

  52. Tadokoro Y, Nishikawa T, Ichimori T, Matsunaga S, Fujita MJ, Sakai R (2017) ACS Omega 2:1074–1080

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Miyako K, Yasuda Y, Shinada T, Fujita M, Sakai R (2020) J Nat Prod 83:3156–3165

    Google Scholar 

  54. Angelina E, Andujar S, Moreno L, Garibotto F, Párraga J, Peruchena N, Cabedo N, Villecco M, Cortes D, Enriz RD (2015) Mol Inform 34:28–43

    Article  CAS  PubMed  Google Scholar 

  55. Nagatsu T, Matsuura S, Sugimoto T (1989) Med Res Rev 9:25–44

    Article  CAS  PubMed  Google Scholar 

  56. Turk T, Frangež R, Sepčić K (2007) Mar Drugs 5:157–167

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  57. Laville R, Thomas OP, Berrue F, Reyes F, Amade P (2008) Eur J Org Chem 2008:121–125

    Google Scholar 

  58. Tribalat M-A, Marra MV, McCormack GP, Thomas OP (2016) Planta Med 82:843–856

    Article  CAS  PubMed  Google Scholar 

  59. Timm C, Volk C, Sasse F, Köck M (2008) Org Biomol Chem 6:4036–4040

    Article  CAS  PubMed  Google Scholar 

  60. Sepčić K, Guella G, Mancini I, Pietra F, Serra MD, Menestrina G, Tubbs K, Macek P, Turk T (1997) J Nat Prod 60:991–996

    Article  PubMed  Google Scholar 

  61. McClelland D, Evans R, Abidin I, Sharma S, Choudhry F, Jaspars M, Sepčić K, Scott RH (2003) Br J Pharmacol 139:1399–1408

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. Malovrh P, Sepčić K, Turk T, Maček P (1999) Comp Biochem Phys Part C Pharmacol Toxicol Endocrinol 124:221–226

    CAS  Google Scholar 

  63. McLaggan D, Adjimatera N, Sepčić K, Jaspars M, MacEwan DJ, Blagbrough IS, Scott RH (2006) BMC Biotechnol 6:6

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  64. Matsunaga S, Jimbo M, Gill MB, Wyhe LL, Murata M, Nonomura K, Swanson GT, Sakai R (2011) Chembiochem 12:2191–2200

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. Matsunaga S, Kishi R, Otsuka K, Fujita MJ, Oikawa M, Sakai R (2014) Org Lett 16:3090–3093

    Article  CAS  PubMed  Google Scholar 

  66. Matsunaga S, Sakai R, Jimbo M, Kamiya H (2007) Chembiochem 8:1729–1735

    Article  CAS  PubMed  Google Scholar 

  67. Kröger N, Deutzmann R, Sumper M (1999) Science 286:1129–1132

    Article  PubMed  Google Scholar 

  68. Shiozaki H, Miyahara M, Otsuka K, Miyako K, Honda A, Takasaki Y, Takamizawa S, Tukada H, Ishikawa Y, Sakai R (2018) Org Lett 20:3403–3407

    Article  CAS  PubMed  Google Scholar 

  69. Irie R, Miyahara M, Nakamura S, Honda A, Sakai R, Oikawa M (2020) J Nat Prod

    Google Scholar 

  70. Guillen PO, Jaramillo KB, Genta-Jouve G, Thomas OP (2020) Nat Prod Rep 37:515–540

    Article  CAS  PubMed  Google Scholar 

  71. Matsumura K, Taniguchi T, Reimer JD, Noguchi S, Fujita MJ, Sakai R (2018) Org Lett 20:3039–3043

    Article  CAS  PubMed  Google Scholar 

  72. Kinnel RB, Gehrken HP, Scheuer PJ (1993) J Am Chem Soc 115:3376–3377

    Article  CAS  Google Scholar 

  73. Futaki S, Nakase I (2017) Acc Chem Res 50:2449–2456

    Article  CAS  PubMed  Google Scholar 

  74. Guillen PO, Jaramillo KB, Genta-Jouve G, Sinniger F, Rodriguez J, Thomas OP (2017) Org Lett 19:1558–1561

    Article  CAS  PubMed  Google Scholar 

  75. Oda Y, Zhang Q, Matsunaga S, Fujita MJ, Sakai R (2017) Chem Lett 46:1272–1274

    Article  Google Scholar 

  76. Goto-Inoue N, Sato T, Morisasa M, Yamashita H, Maruyama T, Ikeda H, Sakai R (2020) Sci Rep 10:1–10

    Article  CAS  Google Scholar 

  77. Oren A, Gunde-Cimerman N (2007) FEMS Microbiol Lett 269:1–10

    Article  CAS  PubMed  Google Scholar 

  78. Shinzato C, Shoguchi E, Kawashima T, Hamada M, Hisata K, Tanaka M, Fujie M, Fujiwara M, Koyanagi R, Ikuta T (2011) Nature 476:320–323

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgement

Researches conducted by RS are supported by JSPS grants 22380114, 15H04546, 18H02270, 19H03040, and 20H04758.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ryuichi Sakai .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Sakai, R. (2020). Chemical and Biological Aspects of Water-Soluble Heterocyclic Marine Natural Products. In: Kiyota, H. (eds) Marine Natural Products. Topics in Heterocyclic Chemistry, vol 58. Springer, Singapore. https://doi.org/10.1007/7081_2020_46

Download citation

Publish with us

Policies and ethics