Planta Med 2016; 82(09/10): 816-831
DOI: 10.1055/s-0042-103245
Reviews
Georg Thieme Verlag KG Stuttgart · New York

Chemical and Biological Aspects of Marine Sponges from the Family Mycalidae

Leesa J. Habener
1   Environmental Futures Research Institute, School of Environment, Griffith University, Gold Coast, Australia
,
John N. A. Hooper
2   Biodiscovery and Geosciences Program, Queensland Museum, Brisbane, Australia
,
Anthony R. Carroll
1   Environmental Futures Research Institute, School of Environment, Griffith University, Gold Coast, Australia
› Author Affiliations
Further Information

Publication History

received 03 September 2015
revised 29 January 2016

accepted 06 February 2016

Publication Date:
22 March 2016 (online)

Abstract

Sponges are a useful source of bioactive natural products. Members of the family Mycalidae, in particular, have provided a variety of chemical structures including alkaloids, polyketides, terpene endoperoxides, peptides, and lipids. This review highlights the compounds isolated from Mycalid sponges and their associated biological activities. A diverse group of 190 compounds have been reported from over 40 specimens contained in 49 references. Over half of the studies have reported on the biological activities for the compounds isolated. The polyketides, in particular the macrolides, displayed potent cytotoxic activities (< 1 µM), and the alkaloids, in particular the 2,5-disubstituted pyrrole derivatives, were associated with moderate cytotoxic activities (1–20 µM). The pyrrole alkaloids and the cyclic peroxides appear to be phylogenetically restricted to sponges and thus might prove useful when applied to sponge taxonomy. The observed diversity of chemical structures suggests this family makes a good target for targeted biodiscovery projects.

Supporting Information

 
  • References

  • 1 Munro MHG, Blunt JW, Dumdei EJ, Hickford SJH, Lill RE, Li S, Battershill CN, Duckworth AR. The discovery and development of marine compounds with pharmaceutical potential. J Biotechnol 1999; 35: 15-25
  • 2 van Soest RWM, Boury-Esnault N, Hooper JNA, Rützler K, de Voogd NJ, Alvarez de Glasby B, Hajdu E, Pisera AB, Manconi R, Schönberg C, Janussen D, Tabachnick KR, Klautau M, Picton B, Kelly M, Vacelet J, Dohrmann M, Díaz MC, Cardenas P. World Porifera Database, 2015. Available at. http://www.marinespecies.org/porifera Accessed May 25, 2015
  • 3 van Soest RWM, Boury-Esnault N, Vacelet J, Dohrmann M, Erpenbeck D, De Voogd NJ, Santodomingo N, Vanhoorne B, Kelly M, Hooper JNA. Global diversity of sponges (Porifera). PLoS One 2012; 7: e35105
  • 4 van Soest RWM, Hajdu E. Family Mycalidae Lundbeck, 1905. In: Hooper JNA, van Soest RWM, editors Systema Porifera: a guide to the classification of sponges. New York, USA: Kluwer Academic/Plenum Publishers; 2002: 669-690
  • 5 Perry NB, Blunt JW, Munro MH, Pannell LK. Mycalamide A, an antiviral compound from a New Zealand sponge of the genus Mycale . J Am Chem Soc 1988; 110: 4850-4851
  • 6 Northcote PT, Blunt JW, Munro MHG. Pateamine: a potent cytotoxin from the New Zealand marine sponge, Mycale sp. Tetrahedron Lett 1991; 32: 6411-6414
  • 7 West LM, Northcote PT, Battershill CN. Peloruside A: a potent cytotoxic macrolide isolated from the New Zealand marine sponge Mycale sp. J Org Chem 2000; 65: 445-449
  • 8 Venkatesham U, Rama Rao M, Venkateswarlu Y. New 5-alkylpyrrole-2-carboxaldehyde derivatives from the sponge Mycale tenuispiculata . J Nat Prod 2000; 63: 1318-1320
  • 9 Fusetani N, Sugawara T, Matsunaga S, Hirota H. Cytotoxic metabolites of the marine sponge Mycale adhaerens Lambe. J Org Chem 1991; 56: 4971-4974
  • 10 Wang RP, Lin HW, Li LZ, Gao PY, Xu Y, Song SJ. Monoindole alkaloids from a marine sponge Mycale fibrexilis . Biochem Syst Ecol 2012; 43: 210-213
  • 11 Cardellina JH, Nigh D, VanWagenen BC. Plant growth regulatory indoles from the sponges Dysidea etheria and Ulosa ruetzleri . J Nat Prod 1986; 49: 1065-1067
  • 12 Dellar G, Djura P, Sargent MV. Structure and synthesis of a new bromoindole from a marine sponge. J Chem Soc Perkin Trans 1 1981; 1679-1680
  • 13 Li L, Deng Z, Fu H, Li J, Proksch P, Lin W. Chemcial constituents from the marine sponge Iotrochoto birotulata . Pharmazie 2003; 58: 680-681
  • 14 Dillman RL, Cardellina JH. Aromatic secondary metabolites from the sponge Tedania ignis . J Nat Prod 1991; 54: 1056-1061
  • 15 Guerriero A, DʼAmbrosio M, Pietra F, Debitus C, Ribes O. Pteridines, sterols, and indole derivatives from the Lithistid sponge Corallistes undulatus of the Coral sea. J Nat Prod 1993; 56: 1962-1970
  • 16 Guella G, Mancini I, Duhet D, Richer de Forges B, Pietra F. Ethyl 6-bromo-3-indolcarboxylate and 3-hydroxyacetal-6-bromoindole, novel bromoindoles from the sponge Pleroma menoui of the Coral sea. Z Naturforsch C 1989; 44: 914-916
  • 17 Capon RJ, Skene C, Vuong D, Lacey E, Gill JH, Heiland K, Friedel T. Equilibrating isomers: bromoindoles and a seco-xanthine encountered during a study of nematocides from the Southern Australian marine sponge Hymeniacidon sp. J Nat Prod 2002; 65: 368-370
  • 18 Rasmussen T, Jensen J, Anthoni U, Christophersen C, Nielsen PH. Structure and synthesis of bromoindoles from the marine sponge Pseudosuberites hyalinus . J Nat Prod 1993; 56: 1553-1558
  • 19 Bao B, Zhang P, Lee Y, Hong J, Lee CO, Jung JH. Monoindole alkaloids from a marine sponge Spongosorites sp. Mar Drugs 2007; 5: 31-39
  • 20 Rudolph KE, Liberio MS, Davis RA, Carroll AR. Pteridine-, thymidine-, choline-and imidazole-derived alkaloids from the Australian ascidian, Leptoclinides durus . Org Biomol Chem 2013; 11: 261-270
  • 21 Fu X, Schmitz FJ, Tanner RS. Chemical constituents of halophilic facultatively anaerobic bacteria. J Nat Prod 1995; 58: 1950-1954
  • 22 Venkateswarlu Y, Rama Rao M, Farooq Biabani M. 5-Alkylpyrrole-2-carboxaldehydes from the sponges Mycalecarmia monanchrorata and Mycale mytilorum . Indian J Chem B 1996; 35: 876-877
  • 23 Stierle DB, Faulkner DJ. Metabolites of the marine sponge Laxosuberites species. J Org Chem 1980; 45: 4980-4982
  • 24 Ortega MJ, Zubia E, Carballo JL, Salvá J. New cytotoxic metabolites from the sponge Mycale micracanthoxea . Tetrahedron 1997; 53: 331-340
  • 25 Compagnone RS, Oliveri MC, Piña IC, Marques S, Rangel HR, Dagger F, Suárez AI, Gómez M. 5-Alkylpyrrole-2-carboxaldehydes from the Caribbean sponges Mycale microsigmatosa and Desmapsamma anchorata . Nat Prod Lett 1999; 13: 203-211
  • 26 Reddy GB, Dhananjaya N. Chemical investigation of Mycale mytilorum and a study on toxicity and antidiabetic activity of 5-octadecylpyrrole-2-carboxaldehyde. Bioorg Med Chem 2000; 8: 27-36
  • 27 Ortega MJ, Zubía E, Sánchez MC, Salvá J, Carballo JL. Structure and cytotoxicity of new metabolites from the sponge Mycale cecilia . Tetrahedron 2004; 60: 2517-2524
  • 28 Hertiani T, Edrada RA, van Soest RWM, Sudarsono. Muller WEG, Proksch P. Chemical investigation on Indonesian marine sponge Mycale phyllophila . Maj Farm Indones 2009; 20: 104-111
  • 29 Mao SC, Liu Y, Morgan JB, Jekabsons MB, Zhou YD, Nagle DG. Lipophilic 2, 5-disubstituted pyrroles from the marine sponge Mycale sp. inhibit mitochondrial respiration and HIF-1 activation. J Nat Prod 2009; 72: 1927-1936
  • 30 Zhou X, Lin X, Guo X, Yang B, Yang XW, Liu Y. Chemical constituents of the sponge Mycale species from South China sea. Rec Nat Prod 2013; 7: 119-123
  • 31 Bowden BF, Clezy PS, Coll JC, Ravi BN, Tapiolas DM. Studies of Australian soft corals. XXXIV. A new substituted pyrrole from a soft coral-sponge association. Aust J Chem 1984; 37: 227-230
  • 32 Loukaci A, Muricy G, Brouard JP, Guyot M, Vacelet J, Boury-Esnault N. Chemical divergence between two sibling species of Oscarella (Porifera) from the Mediterranean Sea. Biochem Syst Ecol 2004; 32: 893-899
  • 33 Barrow RA, Murray LM, Lim TK, Capon RJ. Mirabilins (A–F): New alkaloids from a Southern Australian marine sponge, Arenochalina mirabilis . Aust J Chem 1996; 49: 767-773
  • 34 Gros E, Al-Mourabit A, Martin MT, Sorres J, Vacelet J, Frederich M, Aknin M, Kashman Y, Gauvin-Bialecki A. Netamines H–N, tricyclic alkaloids from the marine sponge Biemna laboutei and their antimalarial activity. J Nat Prod 2014; 77: 818-823
  • 35 El-Naggar M, Conte M, Capon RJ. Mirabilins revisited: polyketide alkaloids from a Southern Australian marine sponge, Clathria sp. Org Biomol Chem 2010; 8: 407-412
  • 36 Patil AD, Freyer AJ, Offen P, Bean MF, Johnson RK. Three new tricyclic guanidine alkaloids from the sponge Batzella sp. J Nat Prod 1997; 60: 704-707
  • 37 Ferreira EG, Wilke DV, Jimenez PC, de Oliveira JR, Pessoa ODL, Silveira ER, Viana FA, Pessoa C, de Moraes MO, Hajdu E, Costa-Lotufo LV. Guanidine alkaloids from Monanchora arbuscula: Chemistry and antitumor potential. Chem Biodivers 2011; 8: 1433-1445
  • 38 Hua HM, Peng J, Fronczek FR, Kelly M, Hamann MT. Crystallographic and NMR studies of antiinfective tricyclic guanidine alkaloids from the sponge Monanchora unguifera . Bioorg Med Chem 2004; 12: 6461-6464
  • 39 Berlinck RG, Trindade-Silva AE, Santos MF. The chemistry and biology of organic guanidine derivatives. Nat Prod Rep 2012; 29: 1382-1406
  • 40 Grkovic T, Blees JS, Bayer MM, Colburn NH, Thomas CL, Henrich CJ, Peach ML, McMahon JB, Schmid T, Gustafson KR. Tricyclic guanidine alkaloids from the marine sponge Acanthella cavernosa that stabilize the tumor suppressor PDCD4. Mar Drugs 2014; 12: 4593-4601
  • 41 Sorek H, Rudi A, Gueta S, Reyes F, Martin MJ, Aknin M, Gaydou E, Vacelet J, Kashman Y. Netamines A–G: seven new tricyclic guanidine alkaloids from the marine sponge Biemna laboutei . Tetrahedron 2006; 62: 8838-8843
  • 42 Capon RJ, Miller M, Rooney F. Mirabilin G: a new alkaloid from a Southern Australian marine sponge, Clathria species. J Nat Prod 2001; 64: 643-644
  • 43 Santos MF, Harper PM, Williams DE, Mesquita JT, Pinto EG, da Costa-Silva TA, Hajdu E, Ferreira AG, Santos RA, Murphy PJ, Andersen RJ, Tempone AG, Berlinck RG. Anti-parasitic guanidine and pyrimidine alkaloids from the marine sponge Monanchora arbuscula . J Nat Prod 2015; 78: 1101-1112
  • 44 Tavares R, Daloze D, Braekman JC, Hajdu E, Van Soest RWM. 8β-Hydroxyptilocaulin, a new guanidine alkaloid from the sponge Monanchora arbuscula . J Nat Prod 1995; 58: 1139-1142
  • 45 Harbour GC, Tymiak AA, Rinehart jr. KL, Shaw PD, Hughes jr. R, Mizsak SA, Coats JH, Zurenko GE, Li LH, Kuentzel SL. Ptilocaulin and isoptilocaulin, antimicrobial and cytotoxic cyclic guanidines from the Caribbean sponge Ptilocaulis aff. P. spiculifer (Lamarck, 1814). J Am Chem Soc 1981; 103: 5604-5606
  • 46 Coello L, Martín MJ, Reyes F. 1, 5-Diazacyclohenicosane, a new cytotoxic metabolite from the marine sponge Mycale sp. Mar Drugs 2009; 7: 445-450
  • 47 Matsunaga S, Sugawara T, Fusetani N. New mycalolides from the marine sponge Mycale magellanica and their interconversion. J Nat Prod 1998; 61: 1164-1167
  • 48 Riego E, Hernández D, Albericio F, Álvarez M. Directly Linked Polyazoles: Important Moieties in Natural Products. Synthesis (Mass) 2005; 12: 1907-1922
  • 49 Fusetani N, Yasumuro K, Matsunaga S, Hashimoto K. Mycalolides A–C, hybrid macrolides of ulapualides and halichondramide, from a sponge of the genus Mycale . Tetrahedron Lett 1989; 30: 2809-2812
  • 50 Phuwapraisirisan P, Matsunaga S, van Soest RW, Fusetani N. Isolation of a new mycalolide from the marine sponge Mycale izuensis . J Nat Prod 2002; 65: 942-943
  • 51 Tsukamoto S, Koimaru K, Ohta T. Secomycalolide A: A New Proteasome Inhibitor Isolated from a Marine Sponge of the Genus Mycale . Mar Drugs 2005; 3: 29-35
  • 52 Liu Y, Ji H, Zhang S, Jung JH, Xu T. Trisoxazole macrolides from the sponge Sarcotragus species. Chem Nat Compd 2008; 44: 140-141
  • 53 Rashid MA, Gustafson KR, Cardeilina JH, Boyd MR. Mycalolides D and E, new cytotoxic macrolides from a collection of the stony coral Tubastrea faulkneri . J Nat Prod 1995; 58: 1120-1125
  • 54 Matsunaga S, Nogata Y, Fusetani N. Thiomycalolides: new cytotoxic trisoxazole-containing macrolides isolated from a marine sponge Mycale sp. J Nat Prod 1998; 61: 663-666
  • 55 Sirirak T, Kittiwisut S, Janma C, Yuenyongsawad S, Suwanborirux K, Plubrukarn A. Kabiramides J and K, trisoxazole macrolides from the sponge Pachastrissa nux . J Nat Prod 2011; 74: 1288-1292
  • 56 Kobayashi J, Murata O, Shigemori H, Sasaki T. Jaspisamides A–C, new cytotoxic macrolides from the Okinawan sponge Jaspis sp. J Nat Prod 1993; 56: 787-791
  • 57 Kernan MR, Faulkner DJ. Halichondramide, an antifungal macrolide from the sponge Halichondria sp. Tetrahedron Lett 1987; 28: 2809-2812
  • 58 Kernan MR, Molinski TF, Faulkner DJ. Macrocyclic antifungal metabolites from the Spanish dancer nudibranch Hexabranchus sanguineus and sponges of the genus Halichondria . J Org Chem 1988; 53: 5014-5020
  • 59 Kobayashi J, Tsuda M, Fuse H, Sasaki T, Mikami Y. Halishigamides A–D, new cytotoxic oxazole-containing metabolites from Okinawan sponge Halichondria sp. J Nat Prod 1997; 60: 150-154
  • 60 Shin J, Lee HS, Kim JY, Shin HJ, Ahn JW, Paul VJ. New macrolides from the sponge Chondrosia corticata . J Nat Prod 2004; 67: 1889-1892
  • 61 Matsunaga S, Fusetani N, Hashimoto K, Koseki K, Noma M. Bioactive marine metabolites. Part 13. Kabiramide C, a novel antifungal macrolide from nudibranch eggmasses. J Am Chem Soc 1986; 108: 847-849
  • 62 Matsunaga S, Fusetani N, Hashimoto K, Koseki K, Noma M, Noguchi H, Sankawa U. Further kabiramides and halichondramides, cytotoxic macrolides embracing trisoxazole, from the Hexabranchus egg masses. J Org Chem 1989; 54: 1360-1363
  • 63 Roesener JA, Scheuer PJ. Ulapualide A and B, extraordinary antitumor macrolides from nudibranch eggmasses. J Am Chem Soc 1986; 108: 846-847
  • 64 Suenaga K, Kimura T, Kuroda T, Matsui K, Miya S, Kuribayashi S, Sakakura A, Kigoshi H. Synthesis and biological activity of mycalolide analogs. Tetrahedron 2006; 62: 8278-8290
  • 65 Saito S, Watabe S, Ozaki H, Fusetani N, Karaki H. Mycalolide B, a novel actin depolymerizing agent. J Biol Chem 1994; 269: 29710-29714
  • 66 Hori M, Saito S, Shin YZ, Ozaki H, Fusetani N, Karaki H. Mycalolide-B, a novel and specific inhibitor of actomyosin ATPase isolated from marine sponge. FEBS Lett 1993; 322: 151-154
  • 67 Schmitz FJ, Gunasekera SP, Yalamanchili G, Hossain MB, van der Helm D. Tedanolide: a potent cytotoxic macrolide from the Caribbean sponge Tedania ignis . J Am Chem Soc 1984; 106: 7251-7252
  • 68 Chevallier C, Bugni TS, Feng X, Harper MK, Orendt AM, Ireland CM. Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp. J Org Chem 2006; 71: 2510-2513
  • 69 Whitson EL, Pluchino KM, Hall MD, McMahon JB, McKee TC. New candidaspongiolides, tedanolide analogues that selectively inhibit melanoma cell growth. Org Lett 2011; 13: 3518-3521
  • 70 Nishimura S, Matsunaga S, Yoshida M, Hirota H, Yokoyama S, Fusetani N. 13-Deoxytedanolide, a marine sponge-derived antitumor macrolide, binds to the 60 S large ribosomal subunit. Bioorg Med Chem 2005; 13: 449-454
  • 71 Singh AJ, Razzak M, Teesdale-Spittle P, Gaitanos TN, Wilmes A, Paterson I, Goodman JM, Miller JH, Northcote PT. Structure-activity studies of the pelorusides: new congeners and semi-synthetic analogues. Org Biomol Chem 2011; 9: 4456-4466
  • 72 Clardy J. Stopping trouble before it starts. ACS Chem Biol 2006; 1: 17-19
  • 73 Romo D, Rzasa RM, Shea HA, Park K, Langenhan JM, Sun L, Akhiezer A, Liu JO. Total synthesis and immunosuppressive activity of (−)-pateamine A and related compounds: Implementation of a β-lactam-based macrocyclization. J Am Chem Soc 1998; 120: 12237-12254
  • 74 Singh AJ, Xu CX, Xu X, West LM, Wilmes A, Chan A, Hamel E, Miller JH, Northcote PT, Ghosh AK. Peloruside B, a potent antitumor macrolide from the New Zealand marine sponge Mycale hentscheli: isolation, structure, total synthesis, and bioactivity. J Org Chem 2009; 75: 2-10
  • 75 Hood KA, West LM, Rouwé B, Northcote PT, Berridge MV, Wakefield SJ, Miller JH. Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule-stabilizing activity. Cancer Res 2002; 62: 3356-3360
  • 76 Miller JH, Singh AJ, Northcote PT. Microtubule-stabilizing drugs from marine sponges: focus on peloruside A and zampanolide. Mar Drugs 2010; 8: 1059-1079
  • 77 Perry NB, Blunt JW, Munro MH, Thompson AM. Antiviral and antitumor agents from a New Zealand sponge, Mycale sp. 2. Structures and solution conformations of mycalamides A and B. J Org Chem 1990; 55: 223-227
  • 78 West LM, Northcote PT, Hood KA, Miller JH, Page MJ. Mycalamide D, a new cytotoxic amide from the New Zealand marine sponge Mycale species. J Nat Prod 2000; 63: 707-709
  • 79 Venturi V, Davies C, Singh AJ, Matthews JH, Bellows DS, Northcote PT, Keyzers RA, Teesdale-Spittle PH. The protein synthesis inhibitors mycalamides A and E have limited susceptibility toward the drug efflux network. J Biochem Mol Toxicol 2012; 26: 94-100
  • 80 Simpson JS, Garson MJ, Blunt JW, Munro MHG, Hooper JNA. Mycalamides C and D, cytotoxic compounds from the marine sponge Stylinos n. species. J Nat Prod 2000; 63: 704-706
  • 81 Dyshlovoy SA, Fedorov SN, Kalinovsky AI, Shubina LK, Bokemeyer C, Stonik VA, Honecker F. Mycalamide A shows cytotoxic properties and prevents EGF-induced neoplastic transformation through inhibition of nuclear factors. Mar Drugs 2012; 10: 1212-1224
  • 82 Burres NS, Clement JJ. Antitumor activity and mechanism of action of the novel marine natural products mycalamide-A and-B and onnamide. Cancer Res 1989; 49: 2935-2940
  • 83 Hood K, West L, Northcote P, Berridge M, Miller J. Induction of apoptosis by the marine sponge (Mycale) metabolites, mycalamide A and pateamine. Apoptosis 2001; 6: 207-219
  • 84 Phuwapraisirisan P, Matsunaga S, Fusetani N. Mycapolyols A–F, new cytotoxic metabolites of mixed biogenesis from the marine sponge Mycale izuensis . Org Lett 2005; 7: 2233-2236
  • 85 Pettit GR, Kamano Y, Dufresne C, Cerny RL, Herald CL, Schmidt JM. Isolation and structure of the cytostatic linear depsipeptide dolastatin 15. J Org Chem 1989; 54: 6005-6006
  • 86 Cardellina JH, Marner FJ, Moore RE. Malyngamide A, a novel chlorinated metabolite of the marine cyanophyte Lyngbya majuscula . J Am Chem Soc 1979; 101: 240-242
  • 87 Simmons TL, McPhail KL, Ortega-Barría E, Mooberry SL, Gerwick WH. Belamide A, a new antimitotic tetrapeptide from a Panamanian marine cyanobacterium. Tetrahedron Lett 2006; 47: 3387-3390
  • 88 Teta R, Irollo E, Della Sala G, Pirozzi G, Mangoni A, Costantino V. Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research. Mar Drugs 2013; 11: 4451-4463
  • 89 Giordano F, Mayol L, Notaro G, Piccialli V, Sica D. Structure and absolute configuration of two new polybrominated C15 acetogenins from the sponge Mycale rotalis . J Chem Soc Chem Commun 1990; 1990: 1559-1561
  • 90 Notaro G, Piccialli V, Sica D, Mayol L, Giordano F. A further C15 nonterpenoid polybromoether from the encrusting sponge Mycale rotalis . J Nat Prod 1992; 55: 626-632
  • 91 Imre S, Aydogmus Z, Guner H, Lotter H, Wagner H. Polybrominated non-terpenoid C15 compounds from Laurencia paniculata and Laurencia obtusa . Z Naturforsch C 1995; 50: 743-747
  • 92 Suzuki M, Sasage Y, Ikura M, Hikichi K, Kurosawa E. Structure revision of okamurallene and structure elucidation of further C15 non-terpenoid bromoallenes from Laurencia intricata . Phytochemistry 1989; 28: 2145-2148
  • 93 Butler M, Capon R, Nadeson R, Beveridge A. Aromatic bisabolenes from an Australian marine sponge, Arenochalina sp. J Nat Prod 1991; 54: 619-623
  • 94 McEnroe FJ, Fenical W. Structures and synthesis of some new antibacterial sesquiterpenoids from the gorgonian coral Pseudopterogorgia rigida . Tetrahedron 1978; 34: 1661-1664
  • 95 Wright AE, Pomponi SA, McConnell OJ, Kohmoto S, McCarthy PJ. (+)-Curcuphenol and (+)-curcudiol, sesquiterpene phenols from shallow and deep water collections of the marine sponge Didiscus flavus . J Nat Prod 1987; 50: 976-978
  • 96 Peng J, Franzblau SG, Zhang F, Hamann MT. Novel sesquiterpenes and a lactone from the Jamaican sponge Myrmekioderma styx . Tetrahedron Lett 2002; 43: 9699-9702
  • 97 Georgantea P, Ioannou E, Vagias C, Roussis V. Bisabolane and chamigrane sesquiterpenes from the soft coral Pseudopterogorgia rigida . Phytochem Lett 2014; 8: 86-91
  • 98 Gaspar H, Feio SS, Rodrigues AI, Van Soest RWM. Antifungal activity of (+)-curcuphenol, a metabolite from the marine sponge Didiscus oxeata . Mar Drugs 2004; 2: 8-13
  • 99 Corriero G, Madaio A, Mayol L, Piccialli V, Sica D. Rotalin A and B, two novel diterpene metabolites from the encrusting Mediterranean sponge Mycale rotalis (Bowerbank). Tetrahedron 1989; 45: 277-288
  • 100 Rudi A, Benayahu Y, Kashman Y. Mycgranol, a new diterpene from the marine sponge Mycale aff. graveleyi . J Nat Prod 2005; 68: 280-281
  • 101 Fattorusso E, Romano A, Taglialatela-Scafati O, Bavestrello G, Bonelli P, Calcinai B. Coelodiol and coeloic acid, ent-isocopalane diterpenes from the Indonesian sponge Coelocarteria cfr. singaporensis . Tetrahedron Lett 2006; 47: 2197-2200
  • 102 Gavagnin M, Ungur N, Castelluccio F, Muniain C, Cimino G. New minor diterpenoid diacylglycerols from the skin of the nudibranch Anisodoris fontaini . J Nat Prod 1999; 62: 269-274
  • 103 Zubía E, Gavagnin M, Scognamiglio G, Cimino G, Giusto GB. Spongiane and ent-isocopalane diterpenoids from the Mediterranean sponge Spongia zimocca . J Nat Prod 1994; 57: 725-731
  • 104 Capon RJ. Two new norsesterterpene cyclic peroxides from a marine sponge, Mycale (Carmia) cf. spongiosa . J Nat Prod 1991; 54: 190-195
  • 105 Higa T, Kuniyoshi M. Biologically active terpenoids from sponges. In: Fingerman M, Nagabhushanam R, editors Biomaterials from aquatic and terrestrial organisms. Enfield, NH, USA: Science Publishers; 2006: 393-450
  • 106 Capon RJ, Rochfort SJ, Ovenden SP. Cyclic peroxides and related norterpenes from a southern Australian marine sponge, Mycale sp. J Nat Prod 1997; 60: 1261-1264
  • 107 Capon RJ, Macleod JK. Structural and stereochemical studies on marine norterpene cyclic peroxides. Tetrahedron 1985; 41: 3391-3404
  • 108 Albericci M, Braekman JC, Daloze D, Tursch B. Chemical studies of marine invertebrates–XLV: The chemistry of three norsesterterpene peroxides from the sponge Sigmosceptrella laevis . Tetrahedron 1982; 38: 1881-1890
  • 109 Albericci M, Collart-Lempereur M, Braekman JC, Dalcze D, Tursch B, Declercq J, Germain G, Van Meerssche M. Chemical studies of marine invertebrates. XLI. Sigmosceptrellin-A methyl ester a nor-sesterterpenoid peroxide from the sponge Sigmosceptrella laevis . Tetrahedron Lett 1979; 29: 2687-2690
  • 110 Capon RJ, MacLeod JK. Structural and stereochemical studies on marine norterpene cyclic peroxides, Part 2. J Nat Prod 1987; 50: 225-229
  • 111 Tanaka J, Higa T, Suwanborirux K, Kokpol U, Bernardinelli G, Jefford CW. Bioactive norsesterterpene 1, 2-dioxanes from a Thai sponge, Mycale sp. J Org Chem 1993; 58: 2999-3002
  • 112 Capon RJ, Rochfort SJ, Ovenden SP, Metzger RP. Mycaperoxides F and G and a related norterpene ketone from southern Australian marine sponges, Mycale species. J Nat Prod 1998; 61: 525-528
  • 113 Phuwapraisirisan P, Matsunaga S, Fusetani N, Chaitanawisuti N, Kritsanapuntu S, Menasveta P. Mycaperoxide H, a new cytotoxic norsesterterpene peroxide from a Thai marine sponge Mycale sp. J Nat Prod 2003; 66: 289-291
  • 114 Salmoun M, Braekman JC, Dewelle J, Darro F, Kiss R, De Voogd NJ, Van Soest RWM. New terpenoids from two Indonesian marine sponges. Nat Prod Res 2007; 21: 149-155
  • 115 Youssef DTA. Tasnemoxides A–C, new cytotoxic cyclic norsesterterpene peroxides from the Red Sea sponge Diacarnus erythraenus . J Nat Prod 2004; 67: 112-114
  • 116 Ibrahim SR, Ebel R, Wray V, Müller WE, Edrada-Ebel R, Proksch P. Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa . J Nat Prod 2008; 71: 1358-1364
  • 117 Capon RJ, MacLeod JK, Willis AC. Trunculins A and B, norsesterterpene cyclic peroxides from a marine sponge, Latrunculia brevis . J Org Chem 1987; 52: 339-342
  • 118 Chao CH, Chou KJ, Wang GH, Wu YC, Wang LH, Chen JP, Sheu JH, Sung PJ. Norterpenoids and related peroxides from the Formosan marine sponge Negombata corticata . J Nat Prod 2010; 73: 1538-1543
  • 119 Ovenden SP, Capon RJ. Nuapapuin A and sigmosceptrellins D and E: new norterpene cyclic peroxides from a Southern Australian marine sponge, Sigmosceptrella sp. J Nat Prod 1999; 62: 214-218
  • 120 Hattori T, Adachi K, Shizuri Y. New ceramide from marine sponge Haliclona koremella and related compounds as antifouling substances against macroalgae. J Nat Prod 1998; 61: 823-826
  • 121 Muralidhar P, Radhika P, Krishna N, Rao DV, Rao CB. Sphingolipids from marine organisms: a review. Nat Prod Sci 2003; 9: 117-142
  • 122 Cutignano A, Nuzzo G, DʼAngelo D, Borbone E, Fusco A, Fontana A. Mycalol: a natural lipid with promising cytotoxic properties against human anaplastic thyroid carcinoma cells. Angew Chem Int Ed Engl 2013; 125: 9426-9430
  • 123 Seetharamsingh B, Rajamohanan P, Reddy DS. Total Synthesis and structural revision of mycalol, an anticancer natural product from the marine source. Org Lett 2015; 17: 1652-1655
  • 124 Magnusson CD, Haraldsson GG. Ether lipids. Chem Phys Lipids 2011; 164: 315-340
  • 125 Antonov AS, Afiyatullov SS, Kalinovsky AI, Ponomarenko LP, Dmitrenok PS, Aminin DL, Agafonova IG, Stonik VA. Mycalosides B–I, eight new spermostatic steroid oligoglycosides from the sponge Mycale laxissima . J Nat Prod 2003; 66: 1082-1088
  • 126 Zhou X, Sun J, Ma W, Fang W, Chen Z, Yang B, Liu Y. Bioactivities of six sterols isolated from marine invertebrates. Pharm Biol 2014; 52: 187-190
  • 127 Mohamed GA, Abd-Elrazek AE, Hassanean HA, Alahdal AM, Almohammadi A, Youssef DT. New fatty acids from the Red Sea sponge Mycale euplectellioides . Nat Prod Res 2014; 28: 1082-1090
  • 128 Rochfort SJ, Gable RW, Capon RJ. Mycalone: a new steroidal lactone from a Southern Australian marine sponge, Mycale sp. Aust J Chem 1996; 49: 715-718
  • 129 Stonard RJ, Petrovich JC, Andersen RJ. A new C26 sterol peroxide from the opisthobranch mollusk Adalaria sp. and the sea pen Virgularia sp. Steroids 1980; 36: 81-86
  • 130 Findlay JA, Patil AD. A novel sterol peroxide from the sea anenome Metridium senile . Steroids 1984; 44: 261-265
  • 131 Jiménez C, Quiñoá E, Castedo L, Riguera R. Epidioxy sterols from the tunicates Dendrodoa grossularia and Ascidiella aspersa and the Gastropoda Aplysia depilans and Aplysia punctata . J Nat Prod 1986; 49: 905-909
  • 132 Mansoor TA, Hong J, Lee CO, Bae SJ, Im KS, Jung JH. Cytotoxic sterol derivatives from a marine sponge Homaxinella sp. J Nat Prod 2005; 68: 331-336
  • 133 Perianayagam JB, Sharma S, Pillai K, Pandurangan A, Kesavan D. Evaluation of antimicrobial activity of ethanol extract and compounds isolated from Trichodesma indicum (Linn.) R. Br. root. J Ethnopharmacol 2012; 142: 283-286
  • 134 Afiyatullov SS, Antonov AS, Kalinovsky AI, Dmitrenok PS. Two new steroid oligoglycosides from the Caribbean sponge Mycale laxissima . Nat Prod Commun 2008; 3: 1581-1586
  • 135 Kalinovsky AI, Antonov AS, Afiyatullov SS, Dmitrenok PS, Evtuschenko EV, Stonik VA. Mycaloside A, a new steroid oligoglycoside with an unprecedented structure from the Caribbean sponge Mycale laxissima . Tetrahedron Lett 2002; 43: 523-525
  • 136 Antonov AS, Kalinovsky AI, Stonik VA. Ulososide B, a new unusual norlanostane-triterpene glycoside and its genuine aglycone from the Madagascar sponge Ulosa sp. Tetrahedron Lett 1998; 39: 3807-3808
  • 137 Cachet N, Regalado EL, Genta-Jouve G, Mehiri M, Amade P, Thomas OP. Steroidal glycosides from the marine sponge Pandaros acanthifolium . Steroids 2009; 74: 746-750
  • 138 Campagnuolo C, Fattorusso E, Taglialatela-Scafati O. Feroxosides A–B, two norlanostane tetraglycosides from the Caribbean sponge Ectyoplasia ferox . Tetrahedron 2001; 57: 4049-4055
  • 139 Kalinin VI, Ivanchina NV, Krasokhin VB, Makarieva TN, Stonik VA. Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles. Mar Drugs 2012; 10: 1671-1710
  • 140 Nakao Y, Yoshida S, Matsunaga S, Shindoh N, Terada Y, Nagai K, Yamashita JK, Ganesan A, van Soest RWM, Fusetani N. Azumamides A–E: histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge Mycale izuensis . Angew Chem Int Ed Engl 2006; 118: 7715-7719
  • 141 Fusetani N, Matsunaga S. Bioactive sponge peptides. Chem Rev 1993; 93: 1793-1806
  • 142 Itazaki H, Nagashima K, Sugita K, Yoshida H, Kawamura Y, Yasuda Y, Matsumoto K, Ishii K, Uotani N, Nakai H, Terui A, Yoshimatsu S, Ikenishi Y, Nakagawa Y. Isolation and structural elucidation of new cyclotetrapeptides, trapoxins A and B, having detransformation activities as antitumor agents. J Antibiot (Tokyo) 1990; 43: 1524-1532
  • 143 Singh SB, Zink DL, Polishook JD, Dombrowski AW, Darkin-Rattray SJ, Schmatz DM, Goetz MA. Apicidins: Novel cyclic tetrapeptides as coccidiostats and antimalarial agents from Fusarium pallidoroseum . Tetrahedron Lett 1996; 37: 8077-8080
  • 144 Gu W, Cueto M, Jensen PR, Fenical W, Silverman RB. Microsporins A and B: new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A. Tetrahedron 2007; 63: 6535-6541
  • 145 Degenkolb T, Gams W, Brückner H. Natural cyclopeptaibiotics and related cyclic tetrapeptides: structural diversity and future prospects. Chem Biodivers 2008; 5: 693-706
  • 146 Newman DJ, Cragg GM. Bioactive macrocycles from nature. In: Levin J, editor Macrocycles in drug discovery. Cambridge, UK: RSC Publishing; 2014
  • 147 Kato Y, Fusetani N, Matsunaga S, Hashimoto K. Bioactive marine metabolites IX. Mycalisines A and B, novel nucleosides which inhibit cell division of fertilized starfish eggs, from the marine sponge Mycale sp. Tetrahedron Lett 1985; 26: 3483-3486
  • 148 Isono K. Nucleoside antibiotics: structure, biological activity, and biosynthesis. J Antibiot (Tokyo) 1988; 41: 1711-1739
  • 149 McCarty RM, Bandarian V. Biosynthesis of pyrrolopyrimidines. Bioorg Chem 2012; 43: 15-25
  • 150 Larsson J, Gottfries J, Muresan S, Backlund A. ChemGPS-NP: tuned for navigation in biologically relevant chemical space. J Nat Prod 2007; 70: 789-794
  • 151 Rosén J, Lövgren A, Kogej T, Muresan S, Gottfries J, Backlund A. ChemGPS-NPWeb: chemical space navigation online. J Comput Aided Mol Des 2009; 23: 253-259
  • 152 Lee OO, Wang Y, Yang J, Lafi FF, Al-Suwailem A, Qian PY. Pyrosequencing reveals highly diverse and species-specific microbial communities in sponges from the Red Sea. ISME J 2011; 5: 650-664
  • 153 Reveillaud J, Maignien L, Eren AM, Huber JA, Apprill A, Sogin ML, Vanreusel A. Host-specificity among abundant and rare taxa in the sponge microbiome. ISME J 2014; 8: 1198-1209
  • 154 Guella G, Pietra F. Rogiolenyne A, B, and C: the first branched marine C15 acetogenins. Isolation from the red seaweed Laurencia microcladia or the sponge Spongia zimocca of II Rogiolo. Helv Chim Acta 1991; 74: 47-54
  • 155 Taylor RE. Tedanolide and the evolution of polyketide inhibitors of eukaryotic protein synthesis. Nat Prod Rep 2008; 25: 854-861
  • 156 Page M, West L, Northcote P, Battershill C, Kelly M. Spatial and temporal variability of cytotoxic metabolites in populations of the New Zealand sponge Mycale hentscheli . J Chem Ecol 2005; 31: 1161-1174
  • 157 Page MJ, Northcote PT, Webb VL, Mackey S, Handley SJ. Aquaculture trials for the production of biologically active metabolites in the New Zealand sponge Mycale hentscheli (Demospongiae: Poecilosclerida). Aquaculture 2005; 250: 256-269