Abstract
The advent of spongothymidine and spongouridine from the Caribbean sponge Tethya crypta turned the attraction of chemists toward sponges for their unique and novel compounds which have a broad spectrum of biological activity and anticancer property in particular. They find the candidates for the development of new drug analogues with the expected biological activity. The sponge compounds are having a series of bioactivity broadly classified into three groups, viz., pharmacological activity, antagonizing activities, and antifouling activity. Each group is dealt with the allied bioactivities which were observed on the range of sponge compounds during evaluation studies. The biological activities are grouped depending on their similarity and type of testing. The structural groups of the compounds include terpenoids, alkaloids, heterocycles, acetylenic compounds, steroids, and nucleosides. The uniqueness of the selected compounds derived from sponges with the observed bioactivity is discussed.
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References
Adamczeski M, Quiñoá E, Crews P (1988) Unusual anthelminthic oxazoles from a marine sponge. J Am Chem Soc 110:1598–1602
Albizati KF, Martin VA, Agharahimi MR, Stolze DA (1990) In: Scheuer PJ (ed) Bioorganic marine chemistry, vol 5. Springer, Berlin/Heidelberg
Anderson HJ, Coleman JE, Andersen RJ, Roberge M (1997) Cytotoxic peptides hemiasterlin, hemiasterlin A and hemiasterlin B induce mitotic arrest and abnormal spindle formation. Cancer Chemother Pharmacol 39:223–226
Angerhofer CK, Pezzuto JM, Konig GM, Wright AD, Sticher O (1992) Antimalarial activity of sesquiterpenes from the marine sponge Acanthella klethra. J Nat Prod 55:1787–1789
Ankisetty S, Amsler CD, McClintock JB, Baker BJ (2004) Further membranolide diterpenes from the Antarctic sponge Dendrilla membranosa. J Nat Prod 67:1172–1174
Antonov AS, Afiyatullov SS, Kalinovsky AI, Ponomarenko LP, Dmitrenok PS, Aminin DL, Agafonova IG, Stonik VA (2003) Mycalosides B-I, eight New spermostatic steroid oligoglycosides from the sponge Mycale laxissima. J Nat Prod 66:1082–1088
Aoki S, Yoshioka Y, Miyamoto Y, Higuchi K, Setiawan A, Murakami N, Chen ZS, Sumizawa T, Akiyama S, Kobayashi M (1998) Agosterol A, a novel polyhydroxylated sterol acetate reversing multidrug resistance from a marine sponge Spongia sp. Tetrahedron Lett 39:6303–6306
Assmann M, Zea S, Köck M (2001) Sventrin, a New bromopyrrole alkaloid from the Caribbean sponge Agelas sventres. J Nat Prod 64:1593–1595
Baker BJ, Scheuer PJ, Shoolery JN (1988) Papuamine, an antifungal pentacyclic alkaloid from a marine sponge, Haliclona sp. J Am Chem Soc 110:965–966
Bennet CF, Mong S, Clark MA, Kruse, LI, Crooke ST (1987) Differential effects of manoalide on secreted intracellular phospholipases. Biochem Pharmacol 36: 2079–2086; ED de Silva, PJ Scheuer Tetrahedron Lett 1980 21:1611
Bergmann W, Burke DC (1955) Contributions to the study of marine products. XXXIX. The nucleosides of sponges. III. Spongothymidine and spongouridine. J Org Chem 20:1501–1507
Bewley CA, He H, Williams DH, Faulkner DJ (1996) Aciculitins A–C: cytotoxic and antifungal cyclic peptides from the lithistid sponge Aciculites orientalis. J Am Chem Soc 118:4314–4321
Blunt JW, Copp BR, Munro MHG, Northcotec PT, Prinsep MR (2010) Marine natural products. Nat Prod Rep 27:165–237
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2014) Marine natural products. Nat Prod Rep 31:160–258
Bobzin SC, Faulkner DJ (1991) Aromatic alkaloids from the marine sponge Chelonaplysilla sp. J Org Chem 56:4403–4407
Borbone N, Marino SD, Iorizzi M, Zollo F, Debitus C, Esposito G, Iuvone T (2002) Minor steroidal alkaloids from the marine sponge Corticium sp. J Nat Prod 65:1206–1209
Brown JL (1975) The evolution of behavior. Norton, New York, pp 761
Bubb MR, Spector I, Bershadsky AD, Korn ED (1995) Swinholide A is a microfilament disrupting marine toxin that stabilizes actin dimers and severs actin filaments. J Biol Chem 270:3463–3466
Butler MS (2004) The role of natural product chemistry in drug discovery. J Nat Prod 67(12):2141–2153
Cantrell CL, Gustafson KR, Cecere MR, Pannell LK, Boyd MR (2000) Chondropsins A and B: novel antitumor cell growth-inhibitory macrolide lactams from the marine sponge Chondropsis sp. J Am Chem Soc 122:8825–8829
Capon RJ, Rooney F, Murray LM, Collins E, Sim ATR, Rostas JAP, Butler MS, Carroll AR (1998) Dragmacidins: new protein phosphatase inhibitors from a Southern Australian deep-water marine sponge, Spongosorites sp. J Nat Prod 61:660–662
Capon RJ, Skene C, Lacey E, Gill JH, Wadsworth D, Friedel T (1999) Geodin A magnesium salt: a novel nematocide from a southern Australian marine sponge, Geodia. J Nat Prod 62:1256–1259
Capon RJ, Skene C, Vuong D, Lacey E, Gill JH, Heiland K, Friedel T (2002) Equilibrating isomers: bromoindoles and a seco-xanthine encountered during a study of nematocides from the southern Australian marine sponge Hymeniacidon sp. J Nat Prod 65:368–370
Carletti I, Long C, Funel C, Amade P (2003) Yardenone A and B: new cytotoxic triterpenes from the Indian ocean sponge Axinella cf. bidderi. J Nat Prod 66:25–29
Carroll J, Johnsson EN, Ebel R, Hartman MS, Holman TR, Crews P (2001) Probing sponge-derived terpenoids for human 15-L-lipoxygenase inhibitors. J Org Chem 66:6847–6851
Carroll AR, Pierens GK, Fechner G (2002) Dysinosin a: a novel inhibitor of factor VIIa and thrombin from a new genus and species of Australian sponge of the family Dysideidae. J Am Chem Soc 124:13340–13341
Chang CWJ, Patra A, Roll DM, Scheuer PJ, Matsumoto GK, Clardy J (1984) Kalihinol-A, a highly functionalized diisocyano diterpenoid antibiotic from a sponge. J Am Chem Soc 106:4644–4646
Chang LC, Quintero SO, Hooper JNA, Bewley CA (2002) Batzelline D and Isobatzelline E from the Indopacific Sponge Zyzzya fuliginosa. J Nat Prod 65:776–778
Choi K, Hong J, Lee CO, Kim DK, Sim CJ, Im KS, Jung JH (2004) Cytotoxic furanosesterterpenes from a marine sponge Psammocinia sp. J Nat Pro 67:1186–1189
Cimino G, De Stefano S, Minale L, Fattorusso E (1972) Ircinin 1 and 2, linear sesterterpenes from the marine sponge Ircinia oros. Tetrahedron 28:333–341
Corley DG, Moore RHE, Scheuer PJ (1988) Laulimalides: new potent cytotoxic macrolides from a marine sponge and a nudibranch predator. J Org Chem 53:3644–3646
Costantino V, Fattorusso E, Mangoni A, Di Rosa M, Ianaro A (1997) Glycolipids from sponges. Plakoside A and B, two unique prenylated glycosphingolipids with immunosuppressive activity from the marine sponge Plakortis simplex. J Am Chem Soc 119:12465–12470
Costantino V, Fattorusso E, Mangoni A, Di Rosa M, Ianaro A (1999) Glycolipids from sponges, VII: simplexides, novel immunosuppressive glycolipids from the Caribbean sponge Plakortis simplex. Bioorg Med Chem Lett 9:271–276
D’Ambrosio M, Guerriero A, Debitus C, Pietra F (1996) Leucascandrolide A, a new type of macrolide: the first powerfully bioactive metabolite of calcareous sponges (Leucascandra caveolata, a new genus from the coral sea). Helv Chim Acta 79:51–60
D’Auria MV, Giannini C, Zampella A, Minale L, Debitus C, Roussakis C (1998) Crellastatin a: a cytotoxic bis-steroid sulfate from the Vanuatu marine sponge Crella sp. J Org Chem 63:7382–7388
De Guzman FS, Carte B, Troupe N, Faulkner DJ, Harper MK (1999) Neoamphimedine: a new pyridoacridine topoisomerase II inhibitor which catenates DNA. J Org Chem 64:1400–1402
De Marino S, Iorizzi M, Zollo F, Debitus C, Menou JL, Ospina LF, Alcaraz MJ, Payá M (2000) New pyridinium alkaloids from a marine sponge of the genus Spongia with a human phospholipase A2 inhibitor profile. J Nat Prod 63:322–326
De Rosa S, Crispino A, De Giulioc A, Iodice C, Tommonaro G (1997) Cavernosolide, a new sesterterpene from a Tyrrhenian sponge. J Nat Prod 60:844–846
De Rosa S, Crispino A, De Giulio A, Iodice C, Amodeo P, Tancredi T (1999) A New cacospongionolide derivative from the sponge Fasciospongia cavernosa. J Nat Prod 62:1316–1318
De Smet P, Parys JB, Callewaert G, Weidema AF, Hill E, De Smedt H, Erneux Cn Sorrentino V, Missianen L (1999) Xestospongin C is an equally potent inhibitor of the inositol 1,4,5-triphosphate receptor and the endoplasmic-reticulum Ca2+ pumps. Cell Calcium 26:9–13
Djura P, Stierle DB, Sullivan B (1980) Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (Polyfibrospongia) echina. J Org Chem 45:1435–1441
Dunbar DC, Rimoldi JM, Clark AM, Kelly M, Hamann MT (2000) Anti-cryptococcal and nitric oxide synthase inhibitory imidazole alkaloids from the calcareous sponge Leucetta cf. chagosensis. Tetrahedron 56:8795–8798
Eder C, Proksch P, Wray V, Van Soest RWM, Ferdinandus E, Pattisina LA, Sudarsono (1999) New bromopyrrole alkaloids from the indopacific sponge Agelas nakamurai. J Nat Prod 62:1295–1297
Edrada RA, Proksch P, Wray V, Christ R, Witte L, Van Soest RWM (1996a) Bioactive isoquinoline quinone from an undescribed Philippine marine sponge of the genus Xestospongia. J Nat Prod 59:973–976
Edrada RA, Proksch P, Wray V, Witte L, Müller WEG, Van Soest RWM (1996b) Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica. J Nat Prod 59:1056–1060
Edrada RA, Ebel R, Supriyono A, Wray V, Schupp P, Steube K, Van Soest R, Proksch P (2002) Swinhoeiamide A, a new highly active calyculin derivative from the marine sponge Theonella swinhoei. J Nat Prod 65:1168–1172
El Sayed KA, Kelly M, Kara UAK, Ang KKH, Katsuyama DC, Dunbar AA, Khan AA, Hamann MT (2001a) New manzamine alkaloids with potent activity against infectious diseases. J Am Chem Soc 123:1804–1808
El Sayed KA, Hamann MT, Hashish NE, Shier WT, Kelly M, Khan AA (2001b) Antimalarial, antiviral, and antitoxoplasmosis norsesterterpene peroxide acids from the Red Sea sponge Diacarnus erythraeanus. J Nat Prod 64:522–524
Erickson KL, Beutler JA, Cardellina JH, Boyd MR (1997) Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. J Org Chem 62:8188–8192
Erijman EAJ, Ingrum AL, Carney JR, Rinehart KL, Sakai R (1993) Polycyclic guanidine-containing compounds from the Mediterranean sponge Crambe crambe: the structure of 13,14,15-isocrambescidin 800 and the absolute stereochemistry of the pentacyclic guanidine moieties of the crambescidins. J Org Chem 58:4805–4808
Farkašovský JNM (2013) Bioprospecting microbial metagenome for natural products. Biol Sect Cel Mol Biol 68(6):1079–1086
Fattorusso E, Taglialatela-Scafati O (2000) Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides. Tetrahedron Lett 41:9917–9922
Fedoreev SA, Prokof_eva NG, Denisenko VA, Rebachuk NM (1989) Cytotoxic activity of aaptamines from suberitid marine sponges. Pharm Chem J 22:615–618
Ford PW, Gustafson KR, McKee TC, Shigematsu N, Maurizi LK, Pannell LK, Williams DE, De Silva ED, Lassota P, Allen TM, Van Soest R, Andersen RJ, Boyd MR (1999) Papuamides A–D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea. J Am Chem Soc 121:5899–590
French RJ, Yoshikami D, Sheets MF, Olivera BM (2010) The tetrodotoxin receptor of voltage-gated sodium channels – perspectives from interactions with μ-conotoxins. Mar Drugs 8:2153–2161
Fu X, Schmitz FJ, Borges MK, McCready TL, Holmes CFB (1998a) Clavosines A-C from the marine sponge Myriastra clavosa: potent cytotoxins and inhibitors of protein phosphatases 1 and 2A. J Org Chem 63:7957–7963
Fu X, Schmitz FJ, Tanner RS, Kelly-Borges M (1998b) Agelasines H and I, 9-methyladenine-containing diterpenoids from an Agelas sponge. J Nat Prod 61:548–550
Fusetani N, Sugawara T, Mataunaga S (1992) Theopederins A–E, potent antitumor metabolites from a marine sponge Theonella sp. J Org Chem 57:3828–3832
Fusetani N, Shinoda K, Matsunaga S (1993) A potent cytotoxic macrolide possessing two Spiro ketals from marine sponge Cinachyra sp. J Am Chem Soc 115:3917–3981
Fusetani N, Takahashi M, Matsunaga S (1994) Topsentiasterol sulfates, antimicrobial sterol sulfates possessing novel side chains, from a marine sponge, Topsentia sp. Tetrahedron 50:7765–7770
Garcia Pastor P, De Rosa S, De Giulio A, Payá M, Alcaraz MJ (1999) Modulation of acute and chronic inflammatory processes by cacospongionolide B, a novel inhibitor of human synovial phospholipase A2. Br J Pharmacol 126:301–311
Giannini C, Debitus C, Posadas I, Payá M, D’Auria MV (2000) Dysidotronic acid, a new and selective human phospholipase A2 inhibitor from the sponge Dysidea sp. Tetrahedron Lett 41:3257–3260
Giannini C, Debitus C, Lucas R, Ubeda A, Paya M, Hooper JNA (2001) New sesquiterpene derivatives from the sponge Dysidea species with a selective inhibitor profile against human phospholipase A2 and other leukocyte functions. J Nat Prod 64:612–615
Gunasekera SP, Gunasekera M, Longley RE, Schulte GK (1990) Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. J Org Chem 55:4912–4915
Gunasekera SP, McCarthy PJ, Longley RE, Pomponi SA, Wright AE (1999) Secobatzellines A and B, two new enzyme inhibitors from a deep-water Caribbean sponge of the genus Batzella. J Nat Prod 62:1208–1211
Gunasekera SP, Zuleta IA, Longley RE, Wright AE, Pomponi SA (2003) Discorhabdins S, T, and U, new cytotoxic pyrroloiminoquinones from a deep-water Caribbean sponge of the genus Batzella. J Nat Prod 66:1615–1617
Hassan W, Edrada RA, Ebel R, Wray V, Berg A, Van Soest R, Wiryowidagdo S, Proksch P (2004) New imidazole alkaloids from the Indonesian sponge Leucetta chagosensis. J Nat Prod 67:817–822
Hentschel U, Hopke J, Horn M, Friedrich AB, Wagner M, Hacker J, Moore BS (2002) Molecular evidence for a uniform microbial community in sponges from different oceans. Appl Environ Microbiol 68:4431–4440
Hirata Y, Uemura D (1986) Halichondrins – antitumor polyether macrolides from a marine sponge. Pure Appl Chem 58:701–710
Hood KA, West LM, Rouwe´ B, Northcote PT, Berridge MV, Wakefield SJ, Miller JH (2002) Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule-stabilizing activity. Cancer Res 62:3356–3360
Hooper JNA, Van Soest RWM (eds) (2002) Systema Porifera: a guide to the classification of sponges. Kluwer Academic/Plenum Publishers, New York
Hu JF, Schetz JA, Kelly M, Peng JN, Ang KK, Flotow H, Leong CY, Nq SB, Buss AD, Wilkins SP, Hamann MT (2002) New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea. J Nat Prod 65:476–480
Ichiba T, Yoshida WY, Scheuer PJ (1991) Hennoxazoles, bioactive bisoxazoles from a marine sponge. J Am Chem Soc 113:3173–3174
Iguchi K, Shimura H, Taira S, Yokoo C, Matsumoto K, Yamada Y (1994) Aragusterol B and D, New 26,27-cyclosterols from the Okinawan marine sponge of the genus Xestospongia. J Org Chem 59:7499–7502
Isbrucker RA, Cummins J, Pomponi SA, Longley RE, Wright AE (2003) Tubulin polymerizing activity of dictyostatin 1, a polyketide of marine sponge origin. Biochem Pharmacol 66:75–82
Ishiyama H, Ishibashi M, Ogawa A, Yoshida S, Kobayashi J (1997) Taurospongin a, a novel acetylenic fatty acid derivative inhibiting DNA polymerase β and HIV reverse transcriptase from sponge Hippospongia sp. J Org Chem 62:3831–3836
JimBnez C, Quiiiol E, Adamczeski M et al (1991) Novel sponge-derived amino acids. 12. Tryptophan-derived pigments and accompanying sesterterpenes from Fascaplysinopis reticulata. J Org Chem 56:3403–3410
Jiménez JI, Yoshida WY, Scheuer PJ, Lobkovsky E, Clardy J, Kelly M (2000) Honulactones: new bishomoscalarane sesterterpenes from the Indonesian sponge Strepsichordaia aliena. J Org Chem 65:6837–6840
Jiménez MS, Garzòn SP, Rodrı´guez AD (2003) Plakortides M and N, bioactive polyketide endoperoxides from the Caribbean marine sponge Plakortis halichondrioides. J Nat Prod 66:655–661
Juagdan EG, Kalindindi RS, Scheuer PJ, Kelly-Borges M (1995) Elenic acid, an inhibitor of topoisomerase II, from a sponge, Plakinastrella sp. Tetrahedron Lett 36:2905–2908
Kalaitzis JA, Leone PA, Harris L, Butler MS, Ngo A, Hooper JNA, Quinn RJ (1999) Adociasulfates 1, 7, and 8: new bioactive hexaprenoid hydroquinones from the marine Sponge Adocia sp. J Org Chem 64:5571–5574
Kashman Y, Groweiss A, Shmueli U (1980) Latrunculin, a new 2-thiazolidinone macrolide from the marine sponge Latrunculia magnifica. Tetrahedron Lett 21:3629–3632
Kato Y, Fusetani N, Matsunaga S, Hashimoto K (1986) Okinonellins A and B, two novel furanosesterterpenes, which inhibit cell division of fertilized starfish eggs, from the marine sponge Spongionella sp. Experientia 42:1299–1300
Kato Y, Fusetani N, Matsunaga S, Hashimoto K, Koseki K (1988) Isolation and structure elucidation of calyculins B, C, and D, novel antitumor metabolites, from the marine sponge Discodermia calyx. J Org Chem 53:3930–3932
Kernan MR, Faulkner DJ (1988) Sesterterpene sulfates from a sponge of the family Halichondriidae. J Org Chem 53:4574–4578
Keyzers RA, Northcote PT, Webb V (2002) Clathriol, a novel polyoxygenated 14β steroid isolated from the New Zealand marine sponge Clathria lissosclera. J Nat Prod 65:598–600
Kinnel RB, Gehrken HP, Scheuer PJ (1993) Palau’amine: a cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata. J Am Chem Soc 115:3376–3377
Kirsch G, Köng GM, Wright AD, Kaminsky R (2000) A new bioactive sesterterpene and antiplasmodial alkaloids from the marine sponge Hyrtios cf. erecta. J Nat Prod 63:825–829
Kitagawa I, Kobayashi M, Kitanaka K, Kido M, Kyogoku Y (1983) Marine natural products, XII: on the chemical constituents of the Okinawan marine sponge Hymeniacidon aldis. Chem Pharm Bull 31:2321–2328
Kobayashi J, Cheng JF, Ishibashi M, Walchli MR, Yamamura S, Ohizumi Y (1991) Penaresidin A and B, two novel azetidine alkaloids with potent actomyosin ATPase activating activity from the Okinawan marine sponge Penares sp. J Chem Soc Perkin Trans 1:1135–1138
Koiso Y, Morita K, Kobayashi M, Wang W, Ohyabu N, Iwasaki S (1996) Effects of arenastatin A and its synthetic analogs on microtubule assembly. Chemico-Biol Interact 102:183–191
Kondracki MLB, Lacombe F, Guyot M (1999) Methanol adduct of puupehenone, a biologically active derivative from the marine sponge Hyrtios species. J Nat Prod 62:1304–1305
König GM, Wright AD, Angerhofer CK (1996) Novel potent antimalarial diterpene isocyanates, isothiocyanates, and isonitriles from the tropical marine sponge Cymbastela hooperi. J Org Chem 61:3259–3267
Lim YJ, Kim JS, Im KS, Jung JH, Lee CO, Hong J, Kim DK (1999) New cytotoxic polyacetylenes from the marine sponge Petrosia. J Nat Prod 62(9):1215–1217
Luckner M (1983) Secondary metabolites in microorganisms, plants and animals. Berlin, Springer. In: Torssell KBG (ed) (1984) Natural product chemistry. A mechanistic and biosynthetic approach to secondary metabolism, 2nd edn. John Wiley, New York
Matsunaga S, Fusetani N, Konosu S (1985) Bioactive marine metabolites, VII: structures of discodermins B, C, and D, antimicrobial peptides from the marine sponge Discodermia kiiensis. Tetrahedron Lett 26:855–856
Matsunaga S, Nogata Y, Fusetani N (1998a) Thiomycalolides: new cytotoxic trisoxazole-containing macrolides isolated from a marine sponge Mycale sp. J Nat Prod 61:663–666
Matsunaga S, Kamimura T, Fusetani N (1998b) Isolation of 1-carboxymethylnicotinic acid from the marine sponge Anthosigmella cf. raromicrosclera as a cysteine protease inhibitor. J Nat Prod 61:671–672
Matsunaga S, Yamashita T, Tsukamoto S, Fusetani N (1999) Three new antibacterial alkaloids from a marine sponge Stelletta species. J Nat Prod 62:1202–1204
McConnell O, Longley RE, Koehn FE (1994) In: Gullo VP (ed) In the discovery of natural products with therapeutic potential. Butterworth-Heinemann, Boston, pp 109–174
McCormick JL, McKee TC, Cardellina JH, Leid M, Boyd MR (1996) Cytotoxic triterpenes from a marine sponge, Stelletta sp. J Nat Prod 59:1047–1050
Mooberry SL, Tien G, Hernandez AH, Plubrukarn A, Davidson BS (1999) Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents. Cancer Res 59:653–660
Moore BS (2006) Biosynthesis of marine natural products: macroorganisms (Part B). Nat Prod Rep 23:615–629
Muller WEG, Sobel C, Diehl-Seifert B, Maidhof A, Schroder HC (1987) Influence of the antileukemic and anti-human immunodeficiency virus agent avarol on selected immune responses in vitro and in vivo. Biochem Pharmacol 36:1489–1494
Munro MHG, Blunt JW, Dumdei EJ, Hickford SJH, Lill RE, Li S, Battershill CN, Duckworth AR (1999) The discovery and development of marine compounds with pharmaceutical potential. J Biotechnol 70:15–25
Murakami Y, Oshima Y, Yasumoto T (1982) Identification of okadaic acid as a toxic component of a marine dinoflagellate Prorocentrum lima. Bull Jpn Soc Sci Fish 48:69–72
Murakami Y, Takei M, Shindo K, Kitazume C, Tanaka J, Higa T, Fukamachi H (2002) Cyclotheonamide E4 and E5, New Potent Tryptase Inhibitors from an Ircinia species of sponge. J Nat Prod 65:259–261
Nakamura H, Ohizumi Y, Kaboyashi J (1984) Keramadine, a novel antagonist of serotonergic receptors isolated from the Okinawan sea sponge Agelas sp. Tetrahedron Lett 25:2475–2478
Nakamura H, Wu H, Kobayashi J, Kobayashi M, Ohizumi Y, Hirata Y (1985) Agelasidines. Novel hypotaurocyamine derivatives from the Okinawan Sea sponge Agelas nakamurai Hoshino. J Org Chem 50(14):2494–2497
Nakao Y, Oku N, Matsunaga S, Fusetani N (1998) Cyclotheonamides E2 and E3, new potent serine protease inhibitors from the marine sponge of the genus Theonella. J Nat Prod 61:667–670
Nakao Y, Uehara T, Matsunaga S, Fusetani N, Van Soest RWM (2002) Callyspongynic acid, a polyacetylenic acid which inhibits a-glucosidase, from the marine sponge Callyspongia truncata. J Nat Prod 65:922–924
Nasu SS, Yeung BKS, Hamann MT, Scheuer PJ, Kelly-Borges M, Goins K (1995) Puupehenone-related metabolites from two Hawaiian sponges, Hyrtios spp. J Org Chem 60:7290–7292
Newman DJ, Cragg GM (2004) Marine natural products and related compounds in clinical and advanced preclinical trials. J Nat Prod 67(8):1216–1238
Nicholas GM, Hong TW, Molinski TF, Lerch ML, Cancilla MT, Lebrilla CB (1999) Oceanapiside, an antifungal Bis-α, ω-amino alcohol glycoside from the marine sponge Oceanapia phillipensis. J Nat Prod 62:1678–1681
Northcote PT, Blunt JW, Munro MHG (1991) Pateamine: a potent cytotoxin from the New Zealand marine sponge, Mycale sp. Tetrahedron Lett 32:6411–6414
Okino T, Yoshimura E, Hirota H, Fusetani N (1995) Antifouling kalihinenes from the marine sponge Acanthella cavernosa. Tetrahedron Lett 36:8637–8640
Okino T, Yoshimura E, Hirota H (1996) New antifouling Kalihipyrans from the marine sponge Acanthella cavernosa. J Nat Prod 59:1081–1083
Oku N, Matsunaga S, van Soest RWM, Fusetani N (2003) Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp. J Nat Prod 66:1136–1139
Okuda RK, Klein D, Kinnel RB, Li M, Scheuer PJ (1982) Marine natural products: the past twenty years and beyond. Pure Appl Chem 54(10):1907–1914
Oliveros MB, Edrada RA, Proksch P, Wray V, Witte Nad L, Van Soest RW (1998) A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus Strongylophora. J Nat Prod 61:948–952
Ortega MJ, ZubÃa E, Carballo JL, Salva J (1996) Fulvinol, a new long-chain diacetylenic metabolite from the sponge Reniera fulva. J Nat Prod 59:1069–1071
Ovenden SPB, Capon RJ, Lacey E, Gill JH, Friedel T, Wadsworth D (1999) Amphilactams A–D: novel nematocides from southern Australian marine sponges of the genus Amphimedon. J Org Chem 64:1140–1144
Palermo JA, Brasco MFR, Cabezas E, Balzaretti V, Seldes AM (1998) Celenamide E, a tripeptide alkaloid from the Patagonian sponge Cliona chilensis. J Nat Prod 61:488–490
Patil AD, Kumar NV, Kokke WC, Bean MF, Freyer AJ, De Brosse C, Mai S, Truneh A, Faulkner DJ, Carte B, Breen AL, Hertzberg RP, Johnson RK, Westley JW, Potts BCM (1996) Novel alkaloids from the Sponge Batzella sp.: inhibitors of HIV gpl2O-Human CD4 Binding. J Org Chem 60:1182–1188
Patra A, Chang CWJ, Scheuer PJ, Van Duyne GD, Matsumoto GK, Clardy J (1984) An unprecedented triisocyano diterpenoid antibiotic from a sponge. J Am Chem Soc 106:7981–7983
Pattanayak JG, Buddadeb M (2001) Distribution of marine sponges (Porifera) in India. Proc Zool Soc Calcutta 54:73–101
Pawlik JR, Chanas B, Toonen RJ, Fenical W (1995) Defenses of Caribbean sponges against predatory reef fish.1. Chemical deterrency. Mar Ecol Prog Ser 127:183–194
Perry NB, Blunt JW, Munro MHG, Pannell LK (1988) Mycalamide a, an antiviral compound from a New Zealand sponge of the genus Mycale. J Am Chem Soc 110:4850–4851
Perry NB, Ettouati L, Litaudon M, Blunt JW, Munro MHG, Parkin S, Hope H (1994) Alkaloids from the antarctic sponge Kirkpatrickia varialosa, part 1: variolin B, a new antitumour and antiviral compound. Tetrahedron 50:3987–3992
Pettit GR, Cichacz ZA, Gao F, Herald CL, Boyd MR, Schmidt JM, Hooper JNA (1993) Isolation and structure of spongistatin 1. J Org Chem 58:1302–1304
Pettit RK, McAllister SC, Pettit GR, Herald CL, Johnson JM, Cichacz ZA (1997) A broad-spectrum antifungal from the marine sponge Hyrtios erecta. Int J Antimicrob Agents 9:147–152
Pettit GR, Cichacz ZA, Tan R, Hoard MS, Melody N, Pettit RK (1998) Antineoplastic agents. 386. Isolation of sesterstatins 1–3 from the marine sponge Hyrtios erecta. J Nat Prod 61:13–16
Qureshi A, Faulkner DJ (1999) Haplosamates A and B: new steroidal sulfamate esters from two haplosclerid sponges. Tetrahedron 55:8323–8330
Randazzo A, Debitus C, Minale L, Pastor PG, Alcaraz MJ, Payá M, Gomez-Paloma L (1998) Petrosaspongiolides M-R: new potent and selective phospholipase A2 inhibitors from the New Caledonian marine sponge Petrosaspongia nigra. J Nat Prod 61:571–575
Rashid MA, Gustafson KR, Boyd MR (2001) A new isoquinoline alkaloid from the marine sponge Haliclona species. J Nat Prod 64:1249–1250
Reyes F, MartÃn R, Rueda A, Fernández R, Montalvo D, Gómez C, Sánchez-Puelles JM (2004) Discorhabdins I and L, cytotoxic alkaloids from the sponge Latrunculia brevis. J Nat Prod 67:463–465
Ridley CP, Faulkner DJ (2003) New cytotoxic steroidal alkaloids from the Philippine sponge Corticium niger. J Nat Prod 66:1536–1539
Ross SA, Weete JD, Schinazi RF, Wirtz SS, Tharnish P, Scheuer PJ, Hamann MT (2000) Mololipids, a new series of anti-HIV bromotyramine-derived compounds from a sponge of the order Verongida. J Nat Prod 63:501–503
Rudi A, Aknin M, Gaydou EM, Kashman Y (1997) Sodwanones K, L, and M; new triterpenes from the marine sponge, Axinella weltneri. J Nat Prod 60:700–703
Rudi A, Yosief T, Loya S, Hizi A, Schleyer M, Kashman Y (2001) Clathsterol, a novel anti-HIV-1 RT sulfated sterol from the sponge Clathria species. J Nat Prod 64:1451–1453
Rudi A, Afanii R, Gravalos LG, Aknin M, Gaydou E, Vacelet J, Kashman Y (2003) Three new cyclic peroxides from the marine sponge Plakortis aff simplex. J Nat Prod 66:682–685
Rueda A, ZubÃa E, Ortega MJ, Carballo JL, Salva J (1997) New cytotoxic metabolites from the sponge Cacospongia scalaris. J Org Chem 62:1481–1485
Rueda A, ZubÃa E, Ortega MJ, Carballo JL, Salva J (1998) New metabolites from the sponge Spongia agaricina. J Nat Prod 61:258–261
Sakai R, Higa T (1986) Manzamine A, a novel antitumor alkaloid from a sponge. J Am Chem Soc 108:6404–6405
Sakai R, Kamiya H, Murata M, Shimamoto K (1997) A new neurotoxic amino acid from the Micronesian marine sponge Dysidea herbacea. J Am Chem Soc 119:4112–4116
Sandler JS, Colin PL, Hooper JNA, Faulkner DJ (2002) Cytotoxic β-carbolines and cyclic peroxides from the Palauan sponge Plakortis nigra. J Nat Prod 65:1258–1261
Santafé G, Paz V, RodrÃguez J, Jimenez C (2002) Novel cytotoxic oxygenated C29 sterols from the Colombian marine sponge Polymastia tenax. J Nat Prod 65:1161–1164
Sata NU, Matsunaga S, Fusetani N, Van Soest RWM (1999) Aurantosides D, E, and F: new antifungal tetramic acid glycosides from the marine sponge Siliquariaspongia japonica. J Nat Prod 62:969–971
Satitpatipan V, Suwanborirux K (2004) New nitrogenous germacranes from a Thai marine sponge, Axinyssa n. sp. J Nat Prod 67:503–505
Schmidt EW, Suarez CR, Bifano M, Menendez AT, Fairchild CR, Faulkner DJ (2004) Scleritodermin A, a cytotoxic cyclic peptide from the lithistid sponge Scleritoderma nodosum. J Nat Prod 67:475–478
Schwartsmann G, Da Rocha AB, Mattei J, Lopes R (2003) Marine-derived anticancer agents in clinical trials. Expert Opin Investig Drugs 12(8):1367–1383
Searle PA, Molinski TF (1995) Phorboxazoles A and B: potent cytostatic macrolides from marine sponge Phorbas Sp. J Am Chem Soc 117:8126–8131
Sera Y, Adachi K, Shizuri Y (1999a) A new epidioxy sterol as an antifouling substance from a Palauan marine sponge, Lendenfeldia chondrodes. J Nat Prod 62:152–154
Sera Y, Adachi K, Nishida F, Shizuri Y (1999b) A new sesquiterpene as an antifouling substance from a Palauan marine sponge, Dysidea herbacea. J Nat Prod 62:395–396
Sera Y, Adachi K, Fujii K, Shizuri Y (2003) A new antifouling hexapeptide from a Palauan sponge, Haliclona sp. J Nat Prod 66:719–721
Shafiq MI, Steinbrecher T, Schmid R (2012) FASCAPLYSIN as a specific inhibitor for CDK4: insights from molecular modelling. PLoS One 7(8):e42612. doi:10.1371/journal.pone.0042612
Shen YC, Hsieh PW (1997) New sesquiterpene hydroquinones from a Taiwanese marine sponge Polyfibrospongia australis. J Nat Prod 60:93–97
Shen YC, Chen CY, Kuo YH (2001) New sesquiterpene hydroquinones from a Taiwanese marine sponge, Hippospongia metachromia. J Nat Prod 64:801–803
Shimosaka A (2002) Role of NKT cells and a-galactosyl ceramide. Int J Hematol 76:277–279
Shoji N, Umeyama A, Shin K, Takeda K, Arihara S, Kobayashi J, Takei M (1992) Two unique pentacyclic steroids with cis C/D ring junction from Xestospongia bergquistia fromont, powerful inhibitors of histamine release. J Org Chem 57:2996–2997
Sipkema D, Franssen MCR, Osinga R, Tramper J, Wijffels RH (2005) Marine sponges as pharmacy. Marine Biotechnol 7:142–162
Stead P, Hiscox S, Robinson PS, Pike NB, Sidebottom PJ, Roberts AD, Taylor NL, Wright AE, Pomponi SA, Langley D (2000) Eryloside F, a novel penasterol disaccharide possessing potent thrombin receptor antagonist activity. Bioorg Med Chem Lett 10:661–664
Sun HH, Cross SS, Gunasekera M, Koehn FE (1991) Weinbersteroldisulfates A and B, antiviral steroid sulfates from the sponge Petrosia weinbergi. Tetrahedron 47:1185–1190
Tachibana K, Scheuer PJ, Tsukitani Y, Kikuchi H, Van Engen D, Clardy J, Gopichand Y, Schmitz FJ (1981) Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. J Am Chem Soc 103:2469–2471
Takei M, Burgoyne DL, Andersen RJ (1994) Effect of contignasterol on histamine release induced by antiimmunoglobulin E from rat peritoneal mast cells. J Pharm Sci 83:1234–1235
Tanaka J, Marriott G, Higa T, Higa T (2001) Cacofurans A and B, new furanoditerpenes from a marine sponge. J Nat Prod 64:1468–1470
Taylor MW, Radax R, Steger D, Wagner M (2007) Sponge associated microorganisms: evolution, ecology and biotechnological potential. Microbiol Mol Biol Rev 71:295–347
Thomas TRA, Kavlekar DP, LokaBharathi PA (2010) Marine drugs from sponge-microbe association – a review. Mar Drugs 8:1417–1468. doi:10.3390/md8041417
Torres YR, Berlinck RGS, Nascimento GGF, Fortier SC, Pessoa C, de Moraes MO (2002) Antibacterial activity against resistant bacteria and cytotoxicity of four alkaloid toxins isolated from the marine sponge Arenosclera brasiliensis. Toxicon 40:885–891
Tsujii S, Rinehart KL, Gunasekera SP, Kashman Y, Cross SS, Lui MS, Pomponi SA, Diaz MC (1988) Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin: antiviral and antitumor Bis(indoly1)imidazoles from Caribbean deep-sea sponges of the family Halichondriidae. Structural and synthetic studies. J Org Chem 53:5446–5453
Tsukamoto S, Kato H, Hirota H, Fusetani N (1996a) Ceratinamine: an unprecedented antifouling cyanoformamide from the marine sponge Pseudoceratina purpurea. J Org Chem 61:2936–2937
Tsukamoto S, Kato H, Hirota H, Fusetani N (1996b) Mauritiamine, a new antifouling oroidin dimer from the marine sponge Agelas mauritiana. J Nat Prod 59:501–503
Tsukamoto S, Kato H, Hirota H, Fusetani N (1996c) Ceratinamides A and B: new antifouling dibromotyrosine derivatives from the marine sponge Pseudoceratina purpurea. Tetrahedron 52:8181–4186
Tsukamoto S, Kato H, Hirota H, Fusetani N (1996d) Pseudoceratidine: a new antifouling spermidine derivative from the marine sponge Pseudoceratina purpurea. Tetrahedron Lett 37:1439–1440
Tsukamoto S, Kato H, Hirota H, Fusetani N (1997) Seven new polyacetylene derivatives, showing both potent metamorphosis-inducing activity in ascidian larvae and antifouling activity against barnacle larvae, from the marine sponge Callyspongia truncata. J Nat Prod 60:126–130
Tsukamoto S, Matsunaga S, Fusetani N, Van Soest RWM (1998) Acanthosterol sulfates A–J: ten new antifungal steroidal sulfates from a marine sponge Acanthodendrilla sp. J Nat Prod 61:1374–1378
Tsukamoto S, Tane K, Ohta T, Matsunaga S, Fusetani N, Van Soest RWM (2001) Four new bioactive pyrrole-derived alkaloids from the marine sponge Axinella brevistyla. J Nat Prod 64:1576–1578
Tziveleka LA, Vagias C, Roussis V (2003) Natural products with anti-HIV activity from marine organisms. Curr Top Med Chem 3(13):1512–1535
Uno M, Otha S, Otha E, Ikegami S (1996) Callyspongins a and B: novel polyacetylene sulfates from the marine sponge Callyspongia truncata that inhibit fertilization of starfish gametes. J Nat Prod 59:1146–1148
Urban S, De Almeida LP, Carroll AR, Fechner GA, Smith J, Hooper JNA, Quinn RJ (1999) Axinellamines A–D, novel imidazo-azolo-imidazole alkaloids from the Australian marine sponge Axinella sp. J Org Chem 64:731–735
Uriz MJ, Turon X, Galera J, Tur JM (1996) New light on the cell location of avarol within the sponge Dysidea avara (Dendroceratida). Cell Tissue Res 285:519–527
Utkina NK, Denisenko VA, Virovaya MV, Scholokova OV, Prokofeva NG (2002) Two new minor polybrominated Dibenzo-p-dioxins from the marine sponge Dysidea dendyi. J Nat Prod 65:1213–1215
Wang CY, Wang BG, Wiryowidagdo S, Wray V, Van Soest R, Steube KG, Guan HS, Proksch P, Ebel R (2003) Melophlins C-O, thirteen novel tetramic acids from the marine sponge Melophlus sarassinorum. J Nat Prod 66:51–56
Wellington KD, Cambie RC, Rutledge PS, Bergquist PR (2000) Chemistry of sponges, 19: novel bioactive metabolites from Hamigera tarangaensis. J Nat Prod 63:79–85
Wright AE, Pomponi SA, Cross SS, McCarthy P (1992) A new Bis(indo1e) alkaloid from a deep-water marine sponge of the genus Spongosorites. J Org Chem 57:4772–4775
Zabriskie TM, Klocke JA, Ireland CM, Marcus AH, Molinski TF, Faulkner DJ, Xu C, Clardy JC (1986) Jaspamide, a modified peptide from a Jaspis sponge, with insecticidal and antifungal activity. J Am Chem Soc 108:3123–3124
Zampella A, D’Auria MV, Paloma LG, Casapullo A, Minale L, Debitus C, Henin Y (1996) Callipeltin A, an anti-HIV cyclic depsipeptide from the New Caledonian Lithistida sponge Callipelta sp. J Am Chem Soc 118:6202–6209
Acknowledgment
I am grateful to Dr. A. Gopalakrishnan, Director, ICAR-Central Marine Fisheries Research Institute, Kochi for his support and permission to publish this work.
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Rajendran, I. (2016). Bioactive Potential of Sponge Secondary Metabolites. In: Pallela, R., Ehrlich, H. (eds) Marine Sponges: Chemicobiological and Biomedical Applications. Springer, New Delhi. https://doi.org/10.1007/978-81-322-2794-6_10
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