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Marine Drugs  2012 

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

DOI: 10.3390/md10081671

Keywords: glycosides, sponges, structures, activities, taxonomic distribution, biological functions

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Abstract:

Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed.

References

[1]  Stonik, V.A. Some terpenoid and steroid derivatives from echinoderms and sponges. Pure Appl. Chem. 1986, 58, 423–436, doi:10.1351/paC198658030423.
[2]  Stonik, V.A.; Kalinin, V.I.; Avilov, S.A. Toxins from sea cucumbers (Holothuroids): Chemical structures, properties, taxonomic distribution, biosynthesis and evolution. J. Nat. Toxins 1999, 8, 235–248.
[3]  Moraes, G.; Northcote, P.T.; Kalinin, V.I.; Avilov, S.A.; Silchenko, A.S.; Dmitrenok, P.S.; Stonik, V.A.; Levin, V.S. Structure of the major triterpene glycoside from the sea cucumber Stichopus mollis and evidence to reclassify this species into the new genus Australostichopus. Biochem. Syst. Ecol. 2004, 32, 637–650, doi:10.1016/j.bse.2004.02.005.
[4]  Avilov, S.A.; Kalinin, V.I.; Smirnov, A.V. Use of triterpene glycosides for resolving taxonomic problems in the sea cucumber genus Cucumaria (Holothurioidea, Echinodermata). Biochem. Syst. Ecol. 2004, 32, 715–733, doi:10.1016/j.bse.2003.12.008.
[5]  Kalinin, V.I.; Silchenko, A.S.; Avilov, S.A.; Stonik, V.A.; Smirnov, A.V. Sea cucumbers triterpene glycosides, the recent progress in structural elucidation and chemotaxonomy. Phytochem. Rev. 2005, 4, 221–236, doi:10.1007/s11101-005-1354-y.
[6]  Antonov, A.S.; Avilov, S.A.; Kalinovsky, A.I.; Anastyuk, S.D.; Dmitrenok, P.S.; Kalinin, V.I.; Taboada, S.; Bosh, A.; Avila, C.; Stonik, V.A. Triterpene glycosides from Antarctic sea cucumbers. 2. Structure of achlioniceosides A1, A2 and A3 from the sea cucumber Achlionice violaescupidata (=Rhipidothuria racowitzai). J. Nat. Prod. 2009, 72, 33–38.
[7]  Minale, L.; Riccio, R.; Zollo, F. Steroid oligoglycosides and polyhydroxysteroids from the echinoderms. Fortschr. Chem. Org. Naturst. 1993, 62, 75–308.
[8]  Stonik, V.A. Marine polar steroids. Russ. Chem. Rev. 2001, 70, 673–715, doi:10.1070/RC2001v070n08ABEH000679.
[9]  Ivanchina, N.V.; Kicha, A.A.; Stonik, V.A. Steroid glycosides from marine organisms. Steroids 2011, 76, 425–454, doi:10.1016/j.steroids.2010.12.011.
[10]  Ebada, S.S.; Lin, W.H.; Proksch, P. Bioactive sesteterpenes and triterpenes from marine sponges: Occurence and pharmacological significance. Mar. Drugs 2010, 8, 313–346, doi:10.3390/md8020313.
[11]  Hooper, J.N.A.; Van Soest, R.W.M. Systema Porifera: A Guide to the Classification of Sponges; Kluwer Academic/Plenum Publishers: Dordrecht, Netherlands, 2002.
[12]  Kitagawa, I.; Kobayashi, M.; Okamoto, Y.; Yoshikawa, M.; Hamamoto, Y. Structures of sapasinosides A1, B1, and C1, new norlanostane-triterpenoid olygoglycosides from the Palauan marine sponge Asteropus sarasinos. Chem. Pharm. Bull. 1987, 35, 5036–5039, doi:10.1248/cpb.35.5036.
[13]  Schmitz, F.J.; Ksebati, M.B.; Gunasekera, S.P.; Agarwal, S. Sarasinoside A1: A saponin containing amino sugars isolated from a sponge. J. Org. Chem. 1988, 53, 5941–5947.
[14]  Dai, H.-F.; Edrada, R.A.; Ebel, R.; Nimtz, M.; Wray, V.; Proksch, P. Norlanostane triterpenoidal saponins from the marine sponge Melophlus sarassinorum. J. Nat. Prod. 2005, 68, 1231–1237, doi:10.1021/np050152d.
[15]  Kobayashi, M.; Okamoto, Y.; Kitagawa, I. Marine natural products. XXVIII. The structures of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine new norlanostane-triterpenoidal olygoglycosides from the Palauan marine sponge Asteropus sarasinosum. Chem. Pharm. Bull. 1991, 39, 2867–2877.
[16]  Espada, A.; Jimenez, C.; Rodriguez, J.; Crews, P.; Riguera, R. Sarasinosides D-G: Four new triterpenoid saponins from the sponge Asteropus sarasinosum. Tetrahedron 1992, 48, 8685–8696.
[17]  Lee, H.-S.; Seo, Y.; Cho, K.W.; Rho, J.-R.; Shin, J.; Paul, V.J. New triterpenoid saponins from the sponge Melophlus isis. J. Nat. Prod. 2000, 63, 915–919, doi:10.1021/np990589j.
[18]  Santalova, E.A.; Denisenko, V.A.; Dmitrenok, P.S.; Berdyshev, D.V.; Stonik, V.A. Two new sarasinosides from the sponge Melophlus sarasinorum. Nat. Prod. Commun. 2006, 1, 265–271.
[19]  Jaspars, M.; Crews, P. A triterpene tetrasaccharide, formoside, from the Caribbean choristida sponge Erylus formosu. Tetrahedron Lett. 1994, 35, 7501–7504, doi:10.1016/S0040-4039(00)78328-6.
[20]  Cheng, J.-F.; Kobayashi, J.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T. Penasterol, a novel antileukemic sterol from the Okinawan marine sponge Penares sp. J. Chem. Soc. Perkin Trans. I 1988, 2403–2406.
[21]  Shoji, N.; Umeyama, A.; Motoki, S.; Arihara, S.; Ishida, T.; Nomoto, K.; Kobayashi, J.; Takei, M. Potent inhibitors of histamine release, two novel triterpenoids from the Okinawan marine sponge Penares incrustans. J. Nat. Prod. 1992, 55, 1682–1685, doi:10.1021/np50089a021.
[22]  Stead, P.; Hiscox, S.; Robinson, P.S.; Pike, N.B.; Sidebottom, P.J.; Roberts, A.D.; Taylor, N.L.; Wright, A.E.; Pomponi, S.A.; Langley, D. Eryloside F, a novel penasterol disaccharide possessing potent thrombin receptor antagonist activity. Bioorg. Med. Chem. Lett. 2000, 10, 661–664.
[23]  Kubanek, J.; Fenical, W.; Pawlik, J.R. New antifeedant triterpene glycosides from the Caribbean sponge Erylus formosus. Nat. Prod. Lett. 2001, 15, 275–285, doi:10.1080/10575630108041292.
[24]  Antonov, A.S.; Kalinovsky, A.I.; Stonik, V.A.; Afiyatullov, S.S.; Aminin, D.L.; Dmitrenok, P.S.; Mollo, E.; Cimino, G. Isolation and structures of erylosides from the Caribbean sponge Erylus formosus. J. Nat. Prod. 2007, 70, 169–178, doi:10.1021/np060364q.
[25]  Antonov, A.S.; Kalinovsky, A.I.; Dmitrenok, P.S.; Kalinin, V.I.; Stonik, V.A.; Mollo, E.; Cimino, G. New triterpene oligoglycosides from the Caribbean sponge Erylus formosus. Carbohydrate Res. 2011, 346, 2182–2192, doi:10.1016/j.carres.2011.07.008.
[26]  Shin, J.; Lee, H.-S.; Woo, L.; Rho, J.-R.; Seo, Y.; Cho, K.W.; Sim, C.J. New triterpenoid saponins from the sponge Erylus nobilis. J. Nat. Prod. 2001, 64, 767–771, doi:10.1021/np010047d.
[27]  Carmely, S.; Roll, M.; Loya, Y.; Kashman, Y. The structure of eryloside A, a new antitumor and antifungal 4-methylated steroidal glycoside from the sponge Erylus lendenfeldi. J. Nat. Prod. 1989, 52, 167–170, doi:10.1021/np50061a022.
[28]  Sandler, J.S.; Forsburg, S.L.; Faulkner, D.J. Bioactive steroidal glycosides from the marine sponge Erylus lendenfeldi. Tetrahedron 2005, 61, 1199–1206.
[29]  Fouad, M.; Al-Trabeen, K.; Badran, M.; Wray, V.; Edrada, R.A.; Proksch, P.; Ebel, R. New steroidal saponins from the sponge Erylus lendenfeldi. ARKIVOC 2004, 2004, 17–27.
[30]  Gulavita, N.K.; Wright, A.E.; Kelly-Borges, M.; Longley, R.E. Eryloside E from an Atlantic sponge Erylus goffrilleri. Tetrahedron Lett. 1994, 35, 4299–4302.
[31]  Afiyatullov, S.S.; Kalinovsky, A.I.; Antonov, A.S.; Ponomarenko, L.P.; Dmitrenok, P.S.; Aminin, D.L.; Krasokhin, V.B.; Nosova, V.M.; Kisin, A.V. Isolation and structures of erylosides from the Caribbean sponge Erylus goffrilleri. J. Nat. Prod. 2007, 70, 1871–1877.
[32]  D’Auria, M.V.; Paloma, L.G.; Minale, L.; Riccio, R. Structure characterization by two-dimentional NMR spectroscopy, of two marine triterpene olygoglycosides from a Pacific sponge of the genus Erylus. Tetrahedron 1992, 48, 491–498.
[33]  Okada, Y.; Matsunaga, S.; van Soest, R.W.M.; Fusetani, N. Sokodosides, steroid glycosides with an isopropyl chain, from the marine sponge Erylus placenta. J. Org. Chem. 2006, 71, 4884–4888.
[34]  Dasgupta, S.; Pramanik, K.; Mikhopadhyay, B. Oiligosaccharides through reactivity tuning: Convergent synthesis of the trisaccharides of the steroid glycoside sokodoside B isolated from marine sponge Erylus placenta. Tetrahedron 2007, 63, 12310–12316.
[35]  Takada, K.; Nakao, Y.; Matsunaga, S.; van Soest, R.W.M.; Fusetani, N. Nobiloside, a new neuraminidase inhibitory triterpenoidal saponin from the marine sponge Erylus nobilis. J. Nat. Prod. 2002, 65, 411–413.
[36]  Mandal, S.; Das, R.; Mukhopadhyay, B. Synthesis of two trisaccharides related to the triterpenoid saponin eryloside isolated from the sponge Erylus nobilis. Tetrahedron Asymm. 2011, 22, 1108–1113.
[37]  Antonov, A.S.; Kalinovsky, A.I.; Stonik, V.A.; Evtushenko, E.V.; Elyakov, G.B. Structure of Ulososide A—New triterpene glycoside from the sponge Ulosa sp. Izvestia AN SSSR. Ser. Khim. 1994, 1326–1329.
[38]  Antonov, A.S.; Kalinovsky, A.I.; Stonik, V.A. Ulososide B, a new unusual norlanostane-triterpene glycoside and its genuine aglycone from the Madagascar sponge Ulosa sp. Tetrahedron Lett. 1998, 39, 3807–3808.
[39]  Antonov, A.S.; Dmitrenok, P.S.; Stonik, V.A. New triterpene glycosides from the sponge Ulosa sp. Bioorgan. Khimiya. 2002, 28, 209–214.
[40]  Cafieri, F.; Fattorusso, E.; Taglialatela-Scafati, O. Ectyoplasides A–B—Unique triterpene olygoglycosides from the Caribbean sponge Ectyoplasia ferox. Eur. J. Org. Chem. 1999, 231–238.
[41]  Campagnuolo, C.; Fattorusso, E.; Taglialatela-Scafari, O. Feroxosides A–B, two norlanostane tetraglycosides from the Caribbean sponge Ectyoplasia ferox. Tetrahedron 2001, 57, 4049–4055.
[42]  Ravi, B.N.; Wells, R.J.; Croft, K.D. Malabaricane triterpenes from a Fijian collection of the sponge Jaspis stellifera. J. Org. Chem. 1981, 46, 1998–2001.
[43]  McCabe, T.; Clardy, J.; Minale, L.; Pizza, C.; Zollo, F.; Riccio, R. A triterpenoid pigment with isomalabaricane skeleton from the marine sponge Stelletta sp. Tetrahedron Lett. 1982, 23, 3307–3310.
[44]  Tabudravu, J.N.; Jaspars, M. Stelliferin riboside, a triterpene monosaccharide isolated from the Fijian sponge Geodia globostellifera. J. Nat. Prod. 2001, 64, 813–815, doi:10.1021/np010019v.
[45]  Hirashima, M.; Tsuda, K.; Hamada, T.; Okumara, H.; Furukawa, T.; Akiyama, S.; Tajitsu, Y.; Ikeda, R.; Komatsu, M.; Doe, M.; et al. Cytotoxic isomalabaricane derivatives and a monocyclic triterpene glycoside from a sponge Rhabdastrella globostellata. J. Nat. Prod. 2010, 73, 1512–1518.
[46]  Clement, J.A.; Li, M.; Hecht, S.M.; Kingston, D.G.I. Bioactive isomalabaricane triterpenoids from Rhabdastrella globostellata that stabilize the binding of DNA polymerase β to DNA. J. Nat. Prod. 2006, 69, 373–376.
[47]  Fouad, M.; Edrada, R.A.; Ebel, R.; Wray, V.; Muller, W.E.G.; Lin, W.H.; Proksch, P. Cytotoxic isomalabaricane triterpenoids from the marine sponge Rhabdastrella globostellata. J. Nat. Prod. 2006, 69, 211–218, doi:10.1021/np050346t.
[48]  Ksebati, M.B.; Schmitz, F.J.; Gunasekera, S.P. Pouosides A–E, novel triterpene galactosides from a marine sponge Asteropus sp. J. Org. Chem. 1988, 53, 3917–3921.
[49]  Lee, J.-H.; Jang, K.H.; Lee, Y.-J.; Lee, H.-S.; Sim, C.J.; Oh, K.-B.; Shin, J. Triterpene galactoside of the pouoside class and corresponding aglycones from the sponge Lipastrotethya sp. J. Nat. Prod. 2011, 74, 2563–2570, doi:10.1021/np200748g.
[50]  Shmueli, U.; Carmely, A.; Groweiss, A.; Kashman, Y. Sipholenol and sipholenone, two new triterpenes from the marine sponge Siphonochalina siphonella (Levi). Tetrahedron Lett. 1981, 22, 709–712.
[51]  Kashman, Y.; Groweiss, A.; Carmely, S.; Kinamoni, Z.; Czarkie, D.; Rotem, M. Recent research in marine natural products from the Red Sea. Pure Appl. Chem. 1982, 54, 1995–2010.
[52]  Fernandez, J.J.; Souto, M.L.; Norte, M. Marine polyether triterpenes. Nat. Prod. Rep. 2000, 17, 235–246.
[53]  Jain, S.; Laphookheio, S.; Shi, Z.; Fu, L.; Akiyama, S.; Chen, Z.S.; Youssef, D.T.A.; Rob, W.M.; van Soest, R.W.M.; El Sayed, K.A. Reversal of P-glycoprotein-mediated multidrug resistance by sipholane triterpenoids. J. Nat. Prod. 2007, 70, 928–931.
[54]  Kashman, Y.; Yosief, T.; Carmeli, S. New triterpenoids from the Red Sea sponge Siphonochalina siphonella. J. Nat. Prod. 2001, 64, 175–180.
[55]  Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. A new aspect of the high-field NMR application of Mosher’s method. The absolute configuration of marine terpenoid sipholenol A. J. Org. Chem. 1991, 56, 1296–1298.
[56]  Northcote, P.T.; Andersen, R.J. Xestovanin A and secoxestovanin A, triterpenoid glycosides with new carbon skeletons from the sponge Xestospongia vanilla. J. Am. Chem. Soc. 1989, 111, 6276–6280, doi:10.1021/ja00198a044.
[57]  Morris, S.A.; Northcote, P.T.; Andersen, R.J. Triterpenoid glycosides from the Northeastern Pacific marine sponge Xestospongia vanilla. Can. J. Chem. 1991, 69, 1352–1364.
[58]  Hirota, H.; Takayama, S.; Miyashiro, S.; Ozaki, Y.; Ikegami, S. Structure of a novel steroidal saponin, pachastrelloside A, obtained from a marine sponge of the genus Pachastrella. Tetrahedron Lett. 1990, 31, 3321–3324.
[59]  Ryu, G.; Choi, B.W.; Lee, B.H.; Hwang, K.-H.; Lee, U.C.; Jeong, D.S.; Lee, N.H. Wondosterols A–C, three steroidal glycosides from a Korean marine two-sponge association. Tetrahedron 1999, 55, 13171–13178.
[60]  Cachet, N.; Regalado, E.L.; Genta-Jouve, G.; Mehiri, M.; Amade, P.; Thomas, O.P. Steroidal glycosides from the marine sponge Pandaros acanthifolium. Steroids 2009, 74, 746–750.
[61]  Regalado, E.L.; Tasdemir, D.; Kaiser, M.; Cachet, N.; Amade, P.; Thomas, O.P. Antiprotozoal steroidal saponins from the marine sponge Pandaros acanthifolium. J. Nat. Prod. 2010, 73, 1404–1410.
[62]  Regalado, E.; Turk, T.; Tasdemir, D.; Gorjanc, M.; Kaiser, M.; Thomas, O.P.; Fernandez, R.; Amade, P. Cytotoxic and haemolytic steroidal glycosides from the Caribbean sponge Pandaros acanthifolium. Steroids 2011, 76, 1389–1396, doi:10.1016/j.steroids.2011.07.010.
[63]  Regalado, E.; Jimenez-Romero, C.; Genta-Jouve, G.; Tasdemir, D.; Amade, P.; Nogueiras, C.; Thomas, O.P. Acanthifoliosides, minor steroidal saponins from the sponge Pandaros acanthifolium. Tetrahedron 2011, 67, 1011–1018.
[64]  Stonik, V.A.; Makarieva, T.N.; Antonov, A.S.; Elyakov, G.B. Steroidal saponins from the sponge Mycale purpurea. Khimiya Prirod. Soedin. 1981, 1, 104–105.
[65]  Kalinovsky, A.I.; Antonov, A.S.; Dmitrenok, P.S.; Evtuschenko, E.V.; Stonik, V.A. Mycaloside A, a new steroid oligoglycoside with an unprecedented structure from the Caribbean sponge Mycale laxissima. Tetrahedron Lett. 2002, 43, 523–525.
[66]  Antonov, A.S.; Afiyatullov, S.S.; Kalinovsky, A.I.; Ponomarenko, L.P.; Dmitrenok, P.S.; Aminin, D.L.; Stonik, V.A. ycalosides B–J, eight new spermostatic steroid oligoglycosides from the sponge Mycale laxissima. J. Nat. Prod. 2003, 66, 1082–1088.
[67]  Afiyatullov, S.S.; Antonov, A.S.; Kalinovsky, A.I.; Dmitrenok, P.S. Two new steroid oligoglycosides from the Caribbean sponge Mycale laxissima. Nat. Prod. Commun. 2008, 3, 1581–1586.
[68]  Yeung, B.K.S.; Hamann, M.T.; Scheuer, P.J.; Kelly-Borges, M. Hapaioside: 19-norpregnane glycoside from the sponge Cribrochalina olemda. Tetrahedron 1994, 50, 12593–12598.
[69]  Gabant, M.; Schmitz-Afonso, I.; Gallard, J.-F.; Menou, J.-L.; Laurent, D.; Debitus, C.; Al-Mourabit, A. Sulfated steroids: Ptilosteroids A–C and ptilosaponosodes A and B from the Solomon Islands marine sponge Ptilocaulis spiculifer. J. Nat. Prod. 2009, 72, 760–763.
[70]  Linington, R.G.; Robertson, M.; Gauthier, A.; Finlay, B.B.; van Soest, R.; Andersen, R.J. Caminoside A, an antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia. Org. Lett. 2002, 4, 4089–4092.
[71]  Linington, R.G.; Robertson, M.; Gauthier, A.; Finlay, B.B.; MacMillan, J.B.; Molinski, T.F.; van Soest, R.; Andersen, R.J. Caminosides B–D, antimicrobial glycolipids isolated from the marine sponge Caminus sphaeroconia. J. Nat. Prod. 2006, 69, 173–177.
[72]  MacMillan, J.B.; Linington, R.G.; Andersen, R.J.; Molinski, T.F. Stereochemical assignment in acyclic lipids across long distance by circular dichroism: absolute stereochemistry of the aglycone of caminoside A. Angew. Chem. Int. Ed. 2004, 43, 5946–5951.
[73]  Sun, J.; Han, X.; Yu, B. First total synthesis of caminoside A, an antimicrobial glycolipid from sponge. Synlett 2005, 3, 437–440.
[74]  Zhang, Z.; Zong, C.; Song, G.; Lv, G.; Chun, Y.; Wang, P.; Ding, N.; Li, Y. Total synthesis of caminoside B, a novel antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia. Carbohydrate Res. 2010, 345, 750–760.
[75]  Warabi, K.; Zimmerman, W.T.; Shen, J.; Gauthier, A.; Robertson, M.; Finlay, B.B.; van Soest, R.; Andersen, R.J. Pachymoside A—a novel glycolipid isolated from the marine sponge Pachymatisma johnstonia. Can. J. Chem. 2004, 82, 102–112, doi:10.1139/v03-183.
[76]  Costantino, V.; Fattorusso, E.; Mangoni, A.; Di Rosa, M.; Ianaro, A. Glycolipids from Sponges. VII. Simplexides, novel immunosuppressive glycolipids from the Caribbean sponge Plakortis simplex. Bioorg. Med. Chem. Lett. 1999, 9, 271–276.
[77]  Costantino, V.; Fattorusso, E.; Imperatore, C.; Mangoni, A. Glycolipids from sponges. Part 17. Clathrosides and isoclathrosides, unique glycolipids from the Caribbean sponge Agelas clathrodes. J. Nat. Prod. 2006, 69, 73–78, doi:10.1021/np050331v.
[78]  Rao, M.R.; Faulkner, D.J. Clavosolides A and B, dimeric macrolides from the Philippines sponge Myriastra clavosa. J. Nat. Prod. 2002, 65, 386–388, doi:10.1021/np010495l.
[79]  Erickson, K.L.; Gustafson, K.R.; Pannell, L.K.; Beutler, J.A.; Boyd, M.R. New dimeric macrolide glycosides from the marine sponge Myriastra clavosa. J. Nat. Prod. 2002, 65, 1303–1306.
[80]  Rezanka, T.; Dembitsky, V.M. Ten-membered substituted cyclic 2-oxecanone (decalactone) derivatives from Latrunculia corticata, a Red Sea sponge. Eur. J. Org. Chem. 2003, 2144–2152.
[81]  Makarieva, T.N.; Denisenko, V.A.; Stonik, V.A.; Milgrom, Y.M.; Rashkes, Y.V. hizochalin, a novel secondary metabolite of mixed biosynthesis from the sponge Rhizochalina incrustata. Tetrahedron Lett. 1989, 30, 6581–6584.
[82]  Makarieva, T.N.; Guzii, A.G.; Denisenko, V.A.; Dmitrenok, P.S.; Santalova, E.A.; Pokanevich, E.V.; Molinski, T.F.; Stonik, V.A. Rhizochalin A, a novel two-headed sphingolipid from the sponge Rhizochalina incrustata. J. Nat. Prod. 2005, 68, 255–257.
[83]  Makarieva, T.N.; Guzii, A.G.; Denisenko, V.A.; Dmitrenok, P.S.; Stonik, V.A. New two-headed sphingolipid-like compounds from the marine sponge Oceanapia sp. Russ. Chem. Bull. 2008, 57, 669–673.
[84]  Makarieva, T.N.; Dmitrenok, P.S.; Zakharenko, A.M.; Denisenko, V.A.; Guzii, A.G.; Li, R.; Skepper, C.K.; Molinski, T.F.; Stonik, V.A. Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in α,ω-bifunctionalized ketosphingolipids. J. Nat. Prod. 2007, 70, 1991–1998.
[85]  Molinski, T.F.; Makarieva, T.N.; Stonik, V.A. (–)-Rhizochalin is a dimeric enantiomorphic (2R)-sphingolipid: Absolute configuration of pseudo-C2V-symmetric bis-2-amino-3-alkanols by CD. Angew. Chem. Int. Ed. 2000, 39, 4076–4079, doi:10.1002/1521-3773(20001117)39:22<4076::AID-ANIE4076>3.0.CO;2-D.
[86]  Makarieva, T.N.; Zakharenko, A.M.; Dmitrenok, P.S.; Guzii, A.G.; Denisenko, V.A.; Savina, A.S.; Dalisay, D.S.; Molinski, T.F.; Stonik, V.A. Isorhizochalin, a minor unprecedented bipolar sphingolipid of stereodivergent biogenesis from the Rhizochalina incrustata. Lipids 2009, 44, 1155–1162, doi:10.1007/s11745-009-3360-0.
[87]  Nicholas, G.M.; Hong, T.W.; Molinski, T.F.; Lerch, M.L.; Cancilla, M.T.; Lebrilla, C.B. Oceanapiside, an antifungal bis-α,ω-amino alcohol glycoside from the marine sponge Oceanapia phillipensis. J. Nat. Prod. 1999, 62, 1678–1681.
[88]  Nicholas, G.M.; Molinski, T.F. Enantiodivergent biosynthesis of the dimeric sphingolipid oceanapiside from the marine sponge Oceanapia phillipensis. Determination of remote stereochemistry. J. Am. Chem. Soc. 2000, 122, 4011–4019.
[89]  Zhou, B.-N.; Mattern, M.P.; Johnson, R.K.; Kingston, D.G.I. Structure and stereochemistry of a novel bioactive sphingolipid from a Calyx sp. Tetrahedron 2001, 57, 9549–9554.
[90]  Makarieva, T.N.; Denisenko, V.A.; Dmitrenok, P.S.; Guzii, A.G.; Santalova, E.A.; Stonik, V.A.; MacMillan, J.B.; Molinski, T.F. Oceanalin A, a hybrid α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp. Org. Lett. 2005, 7, 2897–2900.
[91]  Fedorov, S.N.; Makarieva, T.N.; Guzii, A.G.; Shubina, L.K.; Kwak, J.Y.; Stonik, V.A. Marine two-headed sphingolipid-like compound rhizochalin inhibits EGF-induced transformation of JB6 P+ Cl41 cells. Lipids 2009, 44, 777–785.
[92]  Jin, J.-O.; Shastina, V.; Park, J.-I.; Han, J.-Y.; Makarieva, T.; Fedorov, S.; Rasskazov, V.; Stonik, V.; Kwak, J.-Y. Differential induction of apoptosis of leukemic cells by rhizochalin, two headed sphingolipids from sponge and its derivatives. Biol. Pharm. Bull. 2009, 32, 955–962, doi:10.1248/bpb.32.955.
[93]  Sibirtsev, J.T.; Shastina, V.V.; Menzorova, N.I.; Makarieva, T.N.; Rasskazov, V.A. Ca2+, Mg2+-dependent DNase involvement in apoptotic effects in spermatozoa of sea urchin Strongylocentrotus intermedius induced by two-headed sphingolipid rhizochalin. Mar. Biotechnol. 2011, 13, 536–543.
[94]  Fusetani, N.; Sata, N.; Asai, N.; Matsunaga, S. Isolation and structure elucidation of erylusamine B, a new class of marine natural products, which blocked an IL-6 receptor, from the marine sponge Erylus placenta Thiele. Tetrahedron Lett. 1993, 34, 4067–4070.
[95]  Sata, N.; Asai, N.; Matsunaga, S.; Fusetani, N. Erylusamines, IL-6 receptor antagonists, from the marine sponge, Erylus placenta. Tetrahedron 1994, 50, 1105–1110.
[96]  Goobes, R.; Rudi, A.; Kashman, Y. Three new glycolipids from a Red Sea sponge of the genus Erylus. Tetrahedron 1996, 52, 7921–7928.
[97]  Kubanek, J.; Pawlik, J.R.; Eve, T.M.; Fenical, W. Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes. Mar. Ecol. Prog. Ser. 2000, 207, 69–77.
[98]  Pawlik, J.R. The chemical ecology of sponges on Caribbean reefs: Natural products shape natural systems. BioScience 2011, 61, 888–898.
[99]  Kubanek, J.; Whalen, K.E.; Engel, S.; Kelly, S.R.; Henkel, T.R.; Fenical, W.; Pawlik, J.R. Multiple defensive roles for triterpene glycosides from two Caribbean sponges. Oecologia 2002, 131, 125–136.
[100]  Engel, S.; Pawlik, J.R. Allelopathic activities of sponge extracts. Mar. Ecol. 2000, 207, 273–281.
[101]  Kelly, S.R.; Jensen, P.R.; Henkel, T.P.; Fenical, W.; Pawlik, J.R. Effects of Caribbean sponge extracts on bacterial attachment. Aquat. Microb. Ecol. 2003, 31, 175–182.
[102]  Cohen, S.A.P.; Hatt, H.; Kubanek, J.; McCarty, N.A. Reconstitution of a chemical defense signaling pathway in a heterologous system. J. Exp. Biol. 2008, 211, 599–605.
[103]  Cohen, S.P.; Haack, K.K.V.; Halstead-Nissloch, G.W.; Bernard, K.F.; Hatt, H.; Kubanek, J.; McCarty, N.A. Identification of RL-TGR, a coreceptor involved in aversive chemical signaling. Proc. Natl. Acad. Sci. USA 2010, 107, 12339–12344.

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