Skip to main content
SpringerLink
Log in

Steroid and Triterpenoid Oligoglycosides of Marine Origin

  • Chapter
Saponins Used in Traditional and Modern Medicine

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 404))

Abstract

Saponins have been considered for along time typical metabolites of plant origin. It has been only in the last two decades that the world-wide investigation of marine organisms as sources of new bioactive metabolites disclosed the wide distribution of these molecules also among marine animals. Today saponins are recognized as the most common characteristic metabolites in two classes of the phylum Echinodermata (Holothuroidea and Asteroidea). Furthermore, several steroid and triterpenoid oligoglycosides have been isolated from different species of marine sponges, more rarely Anthozoans, and also from fishes of the genus Pardachirus, where they have been shown to act as shark repellents. This communication offers a general view of the distribution of steroid andtriterpenoidoligoglycosides among marine organisms and focuses on a number of recent examples to discuss structural characteristics, biological activities, and methods of investigation.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. I. Kitagawa, M. Kobayashi, Y. Okamoto, M. Yoshikawa, and Y. Hamamoto, Structures of saranosides A1, B1, and C1; new norlanostane triterpenoid oligoglycosides from the paluan marine sponge, Asteropus sarasinosum, Chem. Pharm. Bull. 35: 5036 (1987).

    Article  PubMed  CAS  Google Scholar 

  2. F. J. Schmitz, M. B. Ksebati, P. Gunasekera, and S. Agarwal, Saranosides Al: a saponin containing amino sugars isolated from a sponge, J. Org. Chem. 53: 5941 (1988).

    Article  CAS  Google Scholar 

  3. H. Hirota, S. Takayama, S. Miyashiro, Y. Ozaki, and S. Ikegami, Structure of a novel steroidal saponin, pachastrelloside A, obtained from a marine sponge of the genus Pachastrella, Tetrahedron Len. 31: 3321 (1990).

    Article  CAS  Google Scholar 

  4. S. Carmely, M. Roll, Y. Loya, and Y. Kashman, The structure of eryloside, a new antitumor and antifungal 4-methylated steroidal glycosides from the sponge Erylus lendenfeldi, J. Nat. Prod. 52: 167 (1989).

    Article  PubMed  CAS  Google Scholar 

  5. M. V. D’Auria, L. Gomez Paloma, L. Minale, and R. Riccio, Structure characterization by two-dimensional nmr spectroscopy, of two marine triterpene oligoglycosides from a Pacific sponge of the genus Erylus, Tetrahedron 48: 491 (1992).

    Article  Google Scholar 

  6. M. M. Bandurraga and W. Fenical, Isolation of muricins. Evidence of a chemical adaptation against fouling in the marine octocoral Muricea fruticosa (Gorgonacea), Tetrahedron 41: 1057 (1985).

    Article  CAS  Google Scholar 

  7. J. M. Wasylyk, G. E. Martin, A. J. Weinheimer, and M. Alain, Isolation and structure identification of a new pregnane glycoside from the gorgonian Pseudoplexaura wayenaori, J. Nat. Prod. 52: 391 (1989).

    Article  CAS  Google Scholar 

  8. N. Fusetani, K. Yasukawa, S. Matsunaga, and K. Hashimoto, Dimorphosides A and B, novel steroid glycosides from the gorgonian Anthoplexaura dimorpha, Tetrahedron Lett. 28: 1187 (1987).

    Article  CAS  Google Scholar 

  9. L. M. V. Tillekeratne, G. K. Liyanage, W. D. Ratnassoriya, M. B. Ksebati, and F. J. Schmitz, A new spermatostatic glycoside from the soft coral Sinularia crispa, J. Nat. Prod. 52: 1143 (1989).

    Article  PubMed  CAS  Google Scholar 

  10. M. Kobayashi, F. Kanda, S. R. Damarla, D. V. Rao, and Ch. B. Rao, Marine sterols. Polyhydroxysterols of the soft corals of the Andaman and Nicobar coasts. (2). Isolation and structures of three 1613hydroxy steroidal glycosides from an Alcyonium sp. soft coral, Chem.Pharm. Bull. 38: 2400 (1990).

    Article  CAS  Google Scholar 

  11. M. Kobayashi, Y. Kiyota, S. Orito, Y. Kyogoku, and I. Kitagawa, Five new steroidal glycosides, pregnedioside-A and -B, and their three monoacetals, from an Okinawan soft coral of Alcyonium sp., Tetrahedron Lett. 25: 3731 (1984).

    Article  CAS  Google Scholar 

  12. K. Tachibana, M. Sakaitanai, and K. Nakanishi, Pavoninins: shark-repelling ichthyotoxins from the defense secretion of the Pacific sole, Science 226: 703 (1984).

    Article  PubMed  CAS  Google Scholar 

  13. K. Tachibana, M. Sakaitanai, and K. Nakanishi, Pavonins, shark-repelling and ichthyotoxic steroid Nacettylglucosaminides from the defense secretion of the sole Pardachirus pavininus (Soleidae), Tetrahedron 41: 1027 (1985).

    Article  CAS  Google Scholar 

  14. K. Tachibana and S. H. Gruber, Shark-repellent lipophilic constituents in the defense secretion of the moles sole (Pardachirus marmoratus), Toxicon 26: 839 (1988).

    Article  PubMed  CAS  Google Scholar 

  15. K. Tachibana, Chemical defense in fishes, In Biorganic Marine Chemistry, vol. 2, P.J. Scheuer Ed., Springer-Verlag, Berlin-Heidelberg, New York, Tokyo (1988).

    Google Scholar 

  16. G. Habermehl and G. Volkwein, Aglycones of the toxins from the cuvierian organs of Holothuria forskali and a new nomenclature for the aglycones from the holothuroideae, Toxicon 9: 319 (1971).

    Article  PubMed  CAS  Google Scholar 

  17. V. A. Stonik and G. B. Elyakov, Secondary metabolites from echinoderms as chemotaxonomic markers, In Bioorganic Marine Chemistry, vol. 2, P. J. Scheuer, Ed., Springer-Verlag, Berlin-Heidelberg New York Tokyo, (1988).

    Chapter  Google Scholar 

  18. J. F. Verbist, Pharmacological effects of compounds from echinoderm, In Echinoderm Studies, M. Jangoux and J. M. Lawrence, Eds., A. A. Balkema, Rotterdam, Brookfield, (1993).

    Google Scholar 

  19. Kitagawa, T. Nishino, and Y. Kyogoku, Structure of holothurin A, a biologically active triterpeneoligoglycoside from the sea cucumber Holothuria leucospilota Brandt, Tetrahedron Lett. 1419 (1979).

    Google Scholar 

  20. I. Kitagawa, T. Nishino, T. Matsuno, H. Akutsu, and Y. Kyogoku, Structure of holothurin B, a biologically active triterpene-oligoglycoside from the sea cucumber Holothuria leucospilota Brandt, Tetrahedron Len. 985 (1978).

    Google Scholar 

  21. V. A. Stonik, and G. B. Elyakov, Structure and biologic activities of sponge and sea cucumber toxins, in Handbook of natural toxins and venoms, vol. 3, A. Tu, ed., Marcel Dekker Inc., New York, (1988).

    Google Scholar 

  22. Kitagawa, M. Kobayashi, T. Inamoto, T. Yasuzawa, and Y. Kyogoku, The structures of six antifungal oligoglycosides, stichlorosides A1, A2, B1, B2, C1, and C2, from the sea cucumber Stichopus chloronotus (Brandt), Chem. Pharm. Bull. 29: 2387 (1981).

    Article  CAS  Google Scholar 

  23. I. Kitagawa, M. Kobayashi, T. Inamoto, T. Yasuzawa, Y. Kyogoku, and M. Kido, Stichlorogenol and dehydrostichlorogenol, genuin aglycones of stichlorosides A1, A2, B1, B2, C1, and C2, from the sea cucumber Stichopus chloronotus (Brandt), Chem. Pharm. Bull. 29: 1189 (1981).

    Article  CAS  Google Scholar 

  24. V.I. Kalinin, A. I. Kalinovsky, V.A. Stonik, P. S. Dmitrenok, and Yu. N. El’Kin, Structure of psolusoside B - nonholostane triterpene glycoside from sea cucumbers of genus Psolus, Chem. Nat. Compd. 25: 311 (1989).

    Article  Google Scholar 

  25. S. A. Avilov, V. I. Kalinin, A. I. Kalinovsky, and V. A. Stonik, Cucumarioside G2 - the minor triterpene glycoside from the sea cucumber Eupentacta fraudatrix, Chem. Nat. Compd. 27: 382 (1991).

    Article  Google Scholar 

  26. S. A. Avilov, A. I. Kalinovsky, and V. A. Stonik, Two new triterpene glycoside from the sea cucumber Duasmodactyla kurilensis, Chem. Nat. Compd. 27: 188 (1991).

    Article  Google Scholar 

  27. T. Miyamoto, K. Togawa, R. Higuchi, T. Komori, and T. Sasaki, Structures of four new triterpenoid oligoglycosides: DS-penaustrosides A, B, C, and D from the sea cucumber Pentacta australis, J. Nat. Prod 55: 940 (1992).

    Article  PubMed  CAS  Google Scholar 

  28. G. G. Habermehl and H. Chr. Krebs, Toxins of echinoderms, In Studies in Natural Products Chemistry, vol. 7, Atta-Ur-Rahman Ed., B. V. Elsevier Science Publishers, Amsterdam (1990).

    Google Scholar 

  29. L. Minale, R. Riccio, and F. Zollo, Structural Studies on Chemical Constituents of echinoderms. In: -Studies in Natural Products Chemistry - Bioactive Natural Products, Atta-ur-Rahman, Ed., Elsevier Science B. V., Amsterdam, (1993).

    Google Scholar 

  30. Y. Hashimoto and T. Yasumoto, Confirmation of saponin as a toxic principle of starfish, Bull. Jpn. Soc. Scient. Fish. 26: 1132 (1960).

    Article  Google Scholar 

  31. A. M. Mackie, R. Lasker, and P. T. Gram, Avoidance reactions of mollusc Baccinum undatum to saponin-like surface active substances in extracts of the starfish Asterias rubens and Marthasterias glacialis, Comp. Biochem. Physiol. 36B: 415 (1968).

    Google Scholar 

  32. S. Ikegami, Y. Kamiya, and S. Tamura, Isolation and characterization of spawning inhibitors in ovary of the starfish Asterias amurensis, Agr. Biol. Chem. 36: 2005 (1972).

    Google Scholar 

  33. Y. Fujimoto, T. Yamada, T. Ikekawa, I. Nishiyama, T. Matsui, and M. Hoshi, Structure of acrosome reaction-inducing steroidal saponins from the egg jelly of the starfish Asterias amurensis, Chem. Pharm. Bull. 35: 1829 (1987).

    Article  CAS  Google Scholar 

  34. N. Fusetani, Y. Kato, K. Hashimoto, T. Komori,Y. Itakura, and T. Kawasaky, Biological activities of asterosaponins with special reference to structure-activity relationships, J. Nat. Prod. 47: 997 (1984).

    Article  CAS  Google Scholar 

  35. L. Andersson, L. Bohlin, M. Iorizzi, R. Riccio, L. Minale, and W. Moreno Lopez, Biological activity of saponins and saponin -like compounds from starfish and brittle-stars, Toxicon 27: 179 (1989).

    Article  PubMed  CAS  Google Scholar 

  36. M. Iorizzi, B. Bryan, J. McClintock, L. Mingle, E. Palagiano, S. Maurelli, R. Riccio, and F. Zollo, Chemical and biological investigation of the polar constituents of the starfish Luidia clathrata, collected in the Gulf of Mexico, J. Nat. Prod. 58: 653 (1995).

    Article  PubMed  CAS  Google Scholar 

  37. L. Minale, R. Riccio, and F. Zollo, Steroidal oligoglycosides and polydroxysteroids from echinoderms, in: Progress in the Chemistry of Organic Natural Products, vol. 62, W. Herz, G.W. Kirby, W. Steglich, Ch. Tamm, eds., Springer-Verlag, Wien, New York, (1993).

    Google Scholar 

  38. Y. Hashimoto. Marine Toxins and Other Bioactive Marine Metabolites, Japan Scientific Societies Press, Tokyo, (1979).

    Google Scholar 

  39. D. J. Burnel and J. W. ApSimon, Echinoderm saponins, in: Marine Natural Products - Chemical and Biological Perspective, vol. V, P. J. Scheuer Ed., Academic Press, New York, San Francisco, (1983).

    Google Scholar 

  40. F. De Simone, A. Dirai, E. Finamore, L. Minale, C. Pizza, R. Riccio, and F. Zollo, Starfish saponins. Part 5. Structure of sepositoside A, a novel steroidal cyclic glycoside from the starfish Echinaster sepositus, J. Chem. Soc., Perkin Trans 1, 1855 (1981).

    Google Scholar 

  41. R. Riccio, L. Mingle, C. Pizza, F. Zollo, and J. Pusset, Starfish saponins. Part 8. Structure of nodosidoside, a novel type of steroidal glycoside from the starfish Protoreaster nodosus, Tetrahedron Lett. 23: 2899 (1982).

    Article  CAS  Google Scholar 

  42. I. Kitagawa and M. Kobayashi, Saponin and sapogenol. XXVI. Steroidal saponins from the starfish Acanthaster planci L. (Crown of the Thorns). (2). Structure of the major saponin thornasteroside A, Chem. Pharm. Bull. 23: 1864 (1978).

    Article  Google Scholar 

  43. Bruno, L. Minale, C. Pizza, F. Zollo, R. Riccio, and F. A. Mellon, Starfish saponins, part 14. Structures of the steroidal glycosides sulphates from the starfish Astropecten scoparius, J. Chem. Soc., Perkin Trans 1: 1875 (1984).

    Google Scholar 

  44. M. V. D’ Auria, M. Iorizzi, L. Minale, and R. Riccio, Starfish saponins, part 40. Structure of two new “asterosaponins” from the starfish Patiria miniata: patirioside A and patirioside B, J.Chem. Soc., Perkin Trans. 1: 1019 (1990).

    Google Scholar 

  45. R. Riccio, M. Iorizzi, and L. Minale, Starfish saponins XXX. Isolation of sixteen steroidal glycosides and three polydroxysteroids from the Mediterranean starfish Coscinasterias tenuispina, Bull. Soc. Chim. Belg. 95: 869 (1986).

    Article  CAS  Google Scholar 

  46. M. Iorizzi, L. Mingle, R. Riccio, M. Debray, and J. L. Menou, Starfish saponins, part 23. Steroidal glycosides from the starfish Halytile regularis, J. Nat. Prod. 49: 67 (1986).

    Article  CAS  Google Scholar 

  47. M. V. D’ Auria, A. Fontana, L. Mingle, and R. Riccio, Starfish saponins XLII. Isolation of twelve steroidal glycosides from the Pacific ocean starfish Henricia laeviuscola, Gazz. Chim. Ital. 120: 155 (1990).

    Google Scholar 

  48. M. Iorizzi, L. Minale, R. Riccio, T. Higa, and J. Tanaka, Starfish saponins. Part 46. Steroidal glycosides and polyhdroxysteroids from the starfish Culcita novaeguineae, J. Nat. Prod. 54: 1254 (1991).

    Article  PubMed  CAS  Google Scholar 

  49. E. Palagiano, M. Iorizzi, L. Minale, F. Zollo, L. Gomez Paloma, J. McClintock, P. Bryan, T. Hopkins, Downeyoside A and B, two novel sulphated steroid glucuronides from the starfish Henricia downeyae, Tetrahedron 51: 12293 (1995).

    Article  CAS  Google Scholar 

  50. E. Palagiano, F. Zollo, L. Minale, M. Iorizzi, P. Bryan, J. McClintock, T. Hopkins, J. Nat. Prod. (submitted).

    Google Scholar 

  51. S. De Marino, M. Iorizzi, L. Minale, and F. Zollo, Isolation of thirthy polydroxysteroids and steroid glycosides from an antarctic starfish of the genus Echinaster, Eight International Symposium on Marine Natural Products, Tenerife 10–15th September 1995, P68, p. 221.

    Google Scholar 

  52. T. Komori, T. Kawasaki, and H. R. Schulten, Field desorption and fast atom bombardment mass spectroscopy of biologically active natural oligoglycosides, Mass Spectrom. Rev., 4: 255 (1985).

    Article  CAS  Google Scholar 

  53. M. Iorizzi, L. Minale, and R. Riccio, Starfish saponins. Part 39. Steroidal oligoglycosides sulphates and polydroxysteroids from the starfish Asterina pectinifera, Gazz. Chim. Ital. 120: 147 (1990).

    CAS  Google Scholar 

  54. R. Riccio, L. Minale, S. Bano, and V. Uddin Ahmad, Starfish saponins. Part 32. Structure of a novel steroidal 5–0-methyl galactofuranoside from the starfish Astropecten indicus, Tetrahedron Lett. 28: 2291 (1987).

    Google Scholar 

  55. R. Riccio, L. Minale, S. Bano, N. Bano, and V. Uddin Ahmad, Starfish saponins. Part 33. Two novel steroidal xylofuranosides from the starfish Astropecten indicus, Gazz. Chim. Ital. 117: 755 (1987).

    CAS  Google Scholar 

  56. C. Pizza, P. Pezzullo, L. Minale, E. Breitmaier, J. Pusset, and P. Tirard, Starfish saponins. Part 20. Two novel steroidal glycosides from the starfish Acanthaster planci, J. Chem. Research, (S) 76, (M) 969 (1985).

    Google Scholar 

  57. C. Pizza, L. Minale, D. Laurent, and J. Menou, Starfish saponins. Part 27. Steroidal glycosides from the starfish Choriaster granulatus, Gazz. Chim. Ital. 115: 585 (1985).

    CAS  Google Scholar 

  58. F. Zollo and L. Minale, Starfish saponins, part 37. Steroidal glycoside sulfates from the starfish of the genus Pisaster, J. Nat. Prod. 52: 693 (1989).

    Article  CAS  Google Scholar 

  59. R. Riccio, M. V. D’ Auria, M. Iorizzi, L. Minale, D. Laurent, and D. Duhet, Starfish saponins. Part 25. Steroidal glycosides from the starfish Gomophia watsoni, Gazz. Chim. Ital. 115: 405 (1985).

    CAS  Google Scholar 

  60. F. De Riccardis, M. Iorizzi, L. Minale, R. Riccio, and C. Debitus, The first occurrence of polyhydroxylated steroids with phosphate conjugation from the starfish Tremaster novaecaledoniae, Tetrahedron Lett. 33: 1097 (1992).

    Article  Google Scholar 

  61. M. Iorizzi, G.Bifulco, F. De Riccardis, L. Minale, R. Riccio, and F. Zollo, Starfish saponins, part 53. A reinvestigation of the polar steroids from the starfish Oreaster reticulatus: isolation of twentytwo constituents, sixteen steroidal oligoglycosides and six polyhydroxysteroids, J. Nat. Prod. 58: 10 (1995).

    Article  PubMed  CAS  Google Scholar 

  62. F. Zollo, E. Finamore, and L. Minale, Starfish saponins. Part 24. Two novel steroidal glycoside sulphates from the starfish Echinaster sepositus, Gazz. Chim. Ital. 115: 303 (1985).

    CAS  Google Scholar 

  63. M. Iorizzi, F. De Riccardis, L. Minale, and R. Riccio, Starfish saponins, Part 52. Chemical constituents from the starfish Echinaster brasiliensis, J. Nat. Prod. 56: 2149 (1993).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, Italy

    L. Minale, M. Iorizzi, E. Palagiano & R. Riccio

Authors
  1. L. Minale
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Iorizzi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. Palagiano
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. Riccio
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Biochemistry and Molecular Biology, Oklahoma State University, 246B Noble Research Center, 74078-0454, Stillwater, Oklahoma, USA

    George R. Waller

  2. Institute of Pharmaceutical Science School of Medicine, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734, Japan

    Kazuo Yamasaki

Additional information

Dedicated to professor Antonio Gonzalez, Universidad de La Laguna, Tenerife, Spain on the occasion of his 50th anniversary of work in the field of natural products chemistry.

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Springer Science+Business Media New York

About this chapter

Cite this chapter

Minale, L., Iorizzi, M., Palagiano, E., Riccio, R. (1996). Steroid and Triterpenoid Oligoglycosides of Marine Origin. In: Waller, G.R., Yamasaki, K. (eds) Saponins Used in Traditional and Modern Medicine. Advances in Experimental Medicine and Biology, vol 404. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1367-8_28

Download citation

  • DOI: https://doi.org/10.1007/978-1-4899-1367-8_28

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-1369-2

  • Online ISBN: 978-1-4899-1367-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation