Sterols and related metabolites from five species of sponges

Biochemical Systematics and Ecology

Volumn 35, Issue 7, 2007, Pages 439-446

  Santalova, Elena A ^a   Makarieva, Tatyana N ^a   Ponomarenko, Ljudmila P ^a   Denisenko, Vladimir A ^a   Krasokhin, Vladimir B ^a   Mollo, Ernesto ^b   Cimino, Guido ^b   Stonik, Valentin A ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

Author keywords

Haliclona sp.; Marine sponges; Monanchora clathrata; Oceanapia sp.; Phyllospongia madagascarensis; Scalarispongia sp.; Steroid ketones; Sterols

Indexed keywords

CHEMOTAXONOMY; METABOLITE; SPONGE; STEROL;

CRAMBEIDAE; HALICLONA; HALICLONA SP.; MONANCHORA CLATHRATA; OCEANAPIA; PHYLLOSPONGIA;

EID: 34247512055     PISSN: 03051978     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bse.2006.10.020     Document Type: Article

References (40)

1. Aiello A., Fattorusso E., and Menna M. Steroids from sponges: recent reports. Steroids 64 (1999) 687-714
2. Baker B.J., and Kerr R.G. Biosynthesis of marine sterols in marine natural products diversity and biosynthesis. In: Scheuer P.J. (Ed). Marine Natural Products - Diversity and Biosynthesis (1993), Springer-Verlag, Berlin 1-32
3. Bergquist P.R., Hofheinz W., and Oesterhelt G. Sterol composition and the classification of the Demospongiae. Biochem. Syst. Ecol. 8 (1980) 423-435
4. Bergquist P.R., Lavis A., and Cambie R.C. Sterol composition and classification of the Porifera. Biochem. Syst. Ecol. 14 (1986) 105-112
5. Bergquist P.R., Cambie R.C., and Kernan M.R. Scalarane sesterterpenes from Collospongia auris, a new Thorectid sponge. Biochem. Syst. Ecol. 18 (1990) 349-357
6. Bergquist P.R., Karuso P., Cambie R.C., and Smith D.J. Sterol composition and classification of the Porifera. Biochem. Syst. Ecol. 19 (1991) 17-24
7. Braekman J.C., Daloze D., Tavares R., Hajdu E., and Van Soest R.W.M. Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora. J. Nat. Prod. 63 (2000) 193-196
8. Brown F.J., and Djerassi C. Elucidation of the course of the electron impact induced fragmentation of α,β-unsaturated 3-ketosteroids. J. Am. Chem. Soc. 102 (1980) 807-813
9. Brown G.D. The biosynthesis of steroids and triterpenoids. Nat. Prod. Rep. 15 (1998) 653-696
10. Cafieri F., Ciminiello P., D'Auria M.V., and Santacroce C. Sterol composition of the marine sponge Crambe crambe. Biochem. Syst. Ecol. 12 (1984) 203-204
11. Castellanos L., Zea S., Osorno O., and Duque C. Phylogenetic analysis of the order Halichondrida (Porifera, Demospongiae), using 3β-hydroxysterols as chemical characters. Biochem. Syst. Ecol. 31 (2003) 1163-1183
12. Cimino G., De Stefano S., and Minale L. Polyprenyl derivatives from the sponge Ircinia spinosula: 2-polyprenylbenzoquinones, 2-polyprenylbenzoquinols, prenylated furans and a C-31 difuranoterpene. Tetrahedron 28 (1972) 1315-1324
13. Costantino V., Fattorusso E., Mangoni A., Aknin M., and Gaydou E.M. Novel 3β-methoxysteroids from the Senegalese sponge Microscleroderma spirophora. Steroids 59 (1994) 181-184
14. Crews P., and Naylor S. Sesterterpenes: An emerging group of metabolites from marine and terrestrial organisms. In: Herz W., Grisebach H., Kirby G.W., and Tamm Ch. (Eds). Progress in the Chemistry of Organic Natural Products (1985), Springer-Verlag, Wien, New York 203-269
15. D'Auria M.V., Paloma L.G., Minale L., Riccio R., Debitus C., and Lévi C. Unique 3β-O-methylsterols from the Pacific sponge Jereicopsis graphidiophora. J. Nat. Prod. 55 (1991) 311-320
16. D'Auria M.V., Paloma L.G., Minale L., and Riccio R. Jereisterol A and B: two 3β-methoxy-secosteroids from the Pacific sponge Jereicopsis graphidiophora. Tetrahedron Lett. 32 (1991) 2149-2152
17. Djerassi C. Recent studies in the marine sterol field. Pure Appl. Chem. 53 (1981) 873-890
18. Djura P., Stierle D.B., Sullivan B., Faulkner D.J., Arnold E., and Clardy J. Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (= Polyfibrospongia) echina. J. Org. Chem. 45 (1980) 1435-1441
19. Erdogan-Orhan I., Sener B., De Rosa S., Perez-Baz J., Lozach O., Leost M., Rachilin S., and Meijer L. Polyprenyl-hydroquinones and -furans from three marine sponges inhibit the cell cycle regulating phosphatase CDC25A. Nat. Prod. Res. 18 (2004) 1-9
20. Fromont J., Kerr S., Kerr R., Riddle M., and Murphy P. Chemotaxonomic relationships within, and comparisons between, the orders Haplosclerida and Petrosida (Porifera: Demospongiae) using sterol complements. Biochem. Syst. Ecol. 22 (1994) 735-752
21. Fu X., Ferreira M.L.G., Schmitz F.J., and Kelly M. Halisulfate 7, a new sesterterpene sulfate from a sponge, Coscinoderma sp. J. Nat. Prod. 62 (1999) 1190-1191
22. Hanson J.R. Sesterterpenoids. Nat. Prod. Rep. 3 (1986) 123-132
23. Kalinin V.I., Anisimov M.M., Prokofieva N.G., Avilov S.A., Afiyatullov Sh.Sh., and Stonik V.A. Biological activities and biological role of triterpene glycosides from holothuroids (Echinodermata). In: Jangoux M., and Lawrence J.M. (Eds). Echinoderm Studies vol. 5 (1996), A.A. Balkema, Rotterdam, Brookfield 139-184
24. Kanasawa A., Teshima S., and Hyodo S. Sterols of the sponges (Porifera, Demospongiae). Comp. Biochem. Physiol. 62B (1979) 521-525
25. Kernan M.R., and Faulkner D.J. Sesterterpene sulfates from a sponge of the family Halichondriidae. J. Org. Chem. 53 (1988) 4574-4578
26. Kerr R.G., and Baker B.J. Marine sterols. Nat. Prod. Rep. 8 (1991) 465-497
27. Lévi C. Lithistid sponges from the Norfolt rise: recent and Mesozoic genera. In: Reitner J., and Keupp H. (Eds). Fossil and Recent Sponges (1991), Springer-Verlag, Berlin 72-82
28. Makarieva T.N., Stonik V.A., Ponomarenko L.P., and Kalinovsky A.I. Isolation of (24R)-24,25-methylene-5α-cholestan-3β-ol, a new cyclopropane-containing sponge sterol. J. Chem. Res. (Synop.) 10 (1996) 468-469
29. Makarieva T.N., Rho J.-R., Lee H.-S., Santalova E.A., Stonik V.A., and Shin J. New sesterterpene sulfates from the sponge Darwinella australiensis. J. Nat. Prod. 66 (2003) 1010-1012
30. Phuwapraisirisan Pr., Matsunaga Sh., van Soest R.W.M., and Fusetani N. Shinsonefuran, a cytotoxic furanosesterterpene with a novel carbon skeleton, from the deep-sea sponge Stoeba extensa. Tetrahedron Lett. 45 (2004) 2125-2128
31. Ponomarenko L.P., Makarieva T.N., and Stonik V.A. A new nortriterpenoid from the deep-sea sponge Sarcotragus spinulosus. Russ. Chem. Bull. 47 (1998) 2017-2019
32. Ponomarenko L.P., Kalinovsky A.I., and Stonik V.A. New scalarane-based sesterterpenes from the sponge Phyllospongia madagascarensis. J. Nat. Prod. 67 (2004) 1507-1510
33. Santalova E.A., Makarieva T.N., Gorshkova I.A., Dmitrenok A.S., Krasokhin V.B., and Stonik V.A. Sterols from the toxic marine sponges. Biochem. Syst. Ecol. 32 (2004) 153-167
34. Seldes A.M., Rovirosa J., San Martin A., and Gros E.G. Steroids from aquatic organisms - XII. Sterols from the Antarctic sponge Homaxinella balfourensis (Ridley and Dendy). Comp. Biochem. Physiol. 83B (1986) 841-842
35. Sheikh Y.M., and Djerassi C. Steroids from sponges. Tetrahedron 30 (1974) 4095-4103
36. Stonik V.A., Makarieva T.N., and Dmitrenok A.S. Sarcochromenol sulfates A-C and sarcohydroquinone sulfates A-C, new natural products from the sponge Sarcotragus spinulosus (Schmidt). J. Nat. Prod. 55 (1992) 1256-1260
37. Stonik V.A. Marine polar steroids. Russ. Chem. Rev. 70 (2001) 673-715
38. Van Altena I.A., and Miller A. A study of the terpenoids of the sponge Euryspongia sp. Aust. J. Chem. 42 (1989) 2181-2190
39. Volkman J.K. Sterols in microorganisms. Appl. Microbiol. Biotechnol. 60 (2003) 495-506
40. Wells R.J. New metabolites from Australian marine species. Pure Appl. Chem. 51 (1979) 1829-1846