Meroterpenes from marine invertebrates: Structures, occurrence, and ecological implications

Marine Drugs

Volumn 11, Issue 5, 2013, Pages 1602-1643

  Menna, Marialuisa ^a   Imperatore, Concetta ^a   D'Aniello, Filomena ^a   Aiello, Anna ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Ascidians; Meroterpenes; Soft corals; Sponges; Terpene hydroquinone; Terpene quinone

Indexed keywords

ALISAQUINOL; ALISIAQUINONE DERIVATIVE; AVAROL; AVARONE; BENZOPYRAN DERIVATIVE; CACOSPONGIN D; CHROMAROL DERIVATIVE; CHROMENE DERIVATIVE; COSCINOQUINOL; COSCINOQUINOL DERIVATIVE; COSCINOSULFATE DERIVATIVE; DOXORUBICIN; DYSIDAVARONE DERIVATIVE; FASCIOQUINOL B; FASCIOQUINOL C; FASCIOQUINOL D; GLABRUQUINONE A; HALISULFATE DERIVATIVE; HYDROQUINONE DERIVATIVE; ILIMAQUINONE; JASPAQUINOL; MEROTERPENE DERIVATIVE; NAKIJIQUINONE DERIVATIVE; PUUPEHENONE; QUINONE DERIVATIVE; SMENODIOL; STRONGYLOPHORINE DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN;

ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ANTIVIRAL ACTIVITY; ASCIDIACEA; ASPERGILLUS; BROWN ALGA; CANCER INHIBITION; CANCER PREVENTION; CELL CYCLE ARREST; CORAL; DERMATITIS; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EHRLICH ASCITES TUMOR; GASTROINTESTINAL TUMOR; HUMAN; IC 50; LEUKEMIA; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PSORIASIS; REVIEW; SKIN CANCER; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION; URINARY TRACT TUMOR; UROCHORDATA; VIRUS INFECTION;

ALCYONACEA; ASCIDIACEA; INVERTEBRATA; PHAEOPHYCEAE; UROCHORDATA;

EID: 84878315644     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11051602     Document Type: Review

References (212)

1. Thomson, R.H. Naturally Occurring Quinones, 2nd ed.; Academic Press: London, UK, 1971; pp. 93-197.
2. Pennock, J.F. Terpenoids in Plants; Pridham, J.B., Ed.; Academic Press: London, UK, 1967; pp. 129-146.
3. Monks, T.J.; Hanzlik, R.P.; Cohen, G.M.; Ross, D.; Graham, D.G. Quinone chemistry and toxicity. Toxicol. Appl. Pharmacol. 1992, 112, 2-16.
4. O'Brien, P.J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 1991, 80, 1-41.
5. Zubìa, E.; Ortega, M.; Salvà, J. Natural products chemistry in marine ascidians of the genus Aplidium. Mini Rev. Org. Chem. 2005, 2, 546-564.
6. Menna, M.; Fattorusso, E.; Imperatore, C. Alkaloids from marine ascidians. Molecules 2011, 16, 8694-8732.
7. Menna, M.; Aiello, A. The Chemistry of Marine Tunicates. In Handbook of Marine Natural Products; Fattorusso, E., Gerwick, W.H., Taglialatela-Scafati, O., Eds.; Springer Science + Business Media: New York, NY, USA, 2012; Volume 1, pp. 295-385.
8. Fenical, W. Geranyl hydroquinone, a cancer-protective agent from the tunicate Aplidium species. Food Drugs Sea Proc. 1976, 4, 388-394.
9. Sato, A.; Shindo, T.; Kasanuki, N.; Hasegawa, K. Antioxidant metabolites from the tunicate Amaroucium multiplicatum. J. Nat. Prod. 1989, 52, 975-981. (Pubitemid 19270607)
10. Aknin, M.; Dayan, T.L.A.; Rudi, A.; Kashman, Y.; Gaydou, E.M. Hydroquinone antioxidants from the Indian Ocean tunicate Aplidium savignyi. J. Agric. Food Chem. 1999, 47, 4175-4177. (Pubitemid 29506220)
11. Garrido, L.; Zubía, E.; Ortega, M.J.; Salvá, J. New meroterpenoids from the ascidian Aplidium conicum. J. Nat. Prod. 2002, 65, 1328-1331.
12. Shubina, L.K.; Fedorov, S.N.; Radchenko, O.S.; Balaneva, N.N.; Kolesnikova, S.A.; Dmitrenok, P.S.; Bode, A.; Dong, Z.; Stonik, V.A. Desmethylubiquinone Q2 from the far-eastern ascidian Aplidium glabrum: Structure and synthesis. Tetrahedron Lett. 2005, 46, 559-562. (Pubitemid 40037904)
13. Chan, S.T.S.; Pearce, A.N.; Januario, A.H.; Page, M.J.; Kaiser, M.; McLaughlin, R.J.; Harper, J.L.; Webb, V.L.; Barker, D.; Copp, B.R. Anti-inflammatory and antimalarial meroterpenoids from the New Zealand ascidian Aplidium scabellum. J. Org. Chem. 2011, 76, 9151-9156.
14. Guella, G.; Mancini, I.; Pietra, F. Verapliquinones: Novel diprenylquinones from an Aplidium sp. (Ascidiacea) of Ile-Verte waters, Brittany. Helv. Chim. Acta 1987, 70, 621-626.
15. Appleton, D.R.; Chuen, C.S.; Berridge, M.V.; Webb, V.L.; Copp, B.R. Rossinones A and B, biologically active meroterpenoids from the Antarctic ascidian, Aplidium species. J. Org. Chem. 2009, 74, 9195-9198.
16. Howard, B.M.; Clarkson, K. Simple prenylated hydroquinone derivatives from the marine urochordate Aplidium californicum natural anticancer and antimutagenic agents. Tetrahedron Lett . 1979, 46, 4449-4452. (Pubitemid 10162459)
17. Fedorov, S.N.; Radchenko, O.S.; Shubina, L.K.; Balaneva, N.N.; Bode, A.M.; Stonik, V.A.; Dong, Z. Evaluation of cancer-preventive activity and structure-activity relationship of 3-demethylubiquinone Q2, isolated from the ascidian Aplidium glabrum and its synthetic analogs. Pharm. Res. 2006, 23, 70-81. (Pubitemid 43214662)
18. Fedorov, S.N.; Radchenko, O.S.; Shubina, L.K.; Balaneva, N.N.; Agafonova, I.G.; Bode, A.M.; Jin, J.O.; Kwak, J.Y.; Dong, Z.; Stonik, V. Anticancer activity of 3-demethylubiquinone Q2. In vivo experiments and probable mechanism of action. Anticancer Res. 2008, 28, 927-932. (Pubitemid 351578939)
19. Laird, D.W.; Poole, R.; Wikstroem, M.; van Altena, I.A. Pycnanthuquinone C, an unusual 6,6,5-tricyclic geranyltoluquinone from the western australian brown alga Cystophora harveyi . J. Nat. Prod. 2007, 70, 671-674.
20. Lumb, J.P.; Trauner, D. Pericyclic reactions of prenylated naphthoquinones: Biomimetic syntheses of mollugin and microphyllaquinone. Org. Lett. 2005, 7, 5865-5868. (Pubitemid 43052872)
21. Morimoto, S.; Komatsu, K.; Taura, F.; Shoyama, Y. Purification and characterization of cannabichromenic acid synthase from Cannabis sativa. Phytochemistry 1998, 49, 1525-1529. (Pubitemid 28559533)
22. Simon-Levert, A.; Arrault, A.; Bontemps-Subielos, N.; Canal, C.; Banaigs, B. Meroterpenes from the ascidian Aplidium aff. densum. J. Nat. Prod. 2005, 68, 1412-1415. (Pubitemid 41499442)
23. Simon-Levert, A.; Aze, A.; Bontemps-Subielos, N.; Banaigs, B.; Genevière, A.M. Antimitotic activity of methoxyconidiol, a meroterpene isolated from an ascidian. Chem. Biol. Interact. 2007, 168, 106-116.
24. Targett, N.M.; Keeran, W.S. A terpenehydroquinone from the marine ascidian Aplidium constellatum . J. Nat. Prod. 1984, 47, 556-557. (Pubitemid 14093186)
25. Rochfort, S.J.; Metzger, R.; Hobbs, L.; Capon, R.J. New chromenols from a southern Australian tunicate Aplidium solidum. Aust. J. Chem. 1996, 49, 1217-1219. (Pubitemid 126552831)
26. Carrol, A.R.; Bowden, B.F.; Coll, J.C. Studies of Australian ascidians. III. A new tetrahydrocannabinol derivative from the ascidian Synoicum costellatum. Aust. J. Chem. 1993, 46, 1079-1083.
27. Choi, H.; Hwang, H.; Chin, J.; Kim, E.; Lee, J.; Nam, S.J.; Lee, B.C.; Rho, B.J.; Kang, H. Tuberatolides, potent FXR antagonists from the korean marine tunicate Botryllus tuberatus. J. Nat. Prod. 2011, 74, 90-94.
28. Davis, R.A.; Carroll, A.R.; Quinn, R.J. Longithorols C-E. Three new macrocyclic sesquiterpene hydroquinone metabolites from the Australian ascidian Aplidium longithorax. J. Nat. Prod. 1999, 62, 1405-1409. (Pubitemid 29504104)
29. Carbone, M.; Nunez-Pons, L.; Paone, M.; Castelluccio, F.; Avila, C.; Gavagnin, M. Rossinone-related meroterpenes from the Antarctic ascidian Aplidium fuegiense. Tetrahedron 2012, 68, 3541-3544.
30. Fort, D.M.; Ubillas, R.P.; Mendez, C.D.; Jolad, S.D.; Inman, W.D.; Carney, J.R.; Chen, J.L.; Ianiro, T.T.; Hasbun, C.; Bruening, R.C.; et al. Novel antihyperglycemic terpenoid-quinones from Pycnanthus angolensis . J. Org. Chem. 2000, 65, 6534-6539.
31. Zhang, Z.; Chen, J.; Yang, Z.; Tang, Y. Rapid biomimetic total synthesis of (±)-rossinone B. Org. Lett. 2010, 12, 5554-5557.
32. Fu, X.; Hossain, M.B.; van der Helm, D.; Schmitz, F.J. Longithorone A: Unprecedented dimeric prenylated quinone from the Tunicate Aplidium longithorax. J. Am. Chem. Soc. 1994, 116, 12125-12126.
33. Fu, X.; Hossain, M.B.; Schmitz, F.J.; van der Helm, D. Longithorones, unique prenylated para- and metacyclophane type quinones from the Tunicate Aplidium longithorax. J. Org. Chem. 1997, 62, 3810-3819.
34. Davis, R.A.; Carroll, A.R.; Quinn, R.J. Longithorones J and K, two new cyclofarnesylated quinone derived metabolites from the Australian ascidian Aplidium longithorax. J. Nat. Prod. 1999, 62, 158-160. (Pubitemid 29071402)
35. Fu, X.; Ferreira, M.L.G.; Schmitz, F.J. Longithorols A and B, novel prenylated paracyclophane- and metacyclophane-tipe hydroquinones from the Tunicate Aplidium longithorax. J. Nat. Prod. 1999, 62, 1306-1310. (Pubitemid 29463336)
36. Kotha, S.; Shirbhate, M.E. Diversity-oriented approach to macrocyclic cyclophane derivatives via ring-closing metathesis. Synlett 2012, 23, 2183-2188.
37. Issa, H.H.; Tanaka, J.; Rachmat, R.; Higa, T. Floresolides, new metacyclophane hydroquinone lactones from an ascidian, Aplidium sp. Tetrahedron Lett. 2003, 44, 1243-1245. (Pubitemid 36144145)
38. Layton, M.E.; Morales, C.A.; Shair, M.D. Biomimetic synthesis of (-)-longithorone A. J. Am. Chem. Soc. 2002, 124, 773-775. (Pubitemid 34112785)
39. Aiello, A.; Fattorusso, E.; Luciano, P.; Menna, M.; Esposito, G.; Iuvone, T.; Pala, D. Conicaquinones A and B, two novel cytotoxic terpene quinones from the Mediterranean ascidian Aplidium conicum. Eur. J. Org. Chem. 2003, 2003, 898-900.
40. Aiello, A.; Fattorusso, E.; Luciano, P.; Mangoni, A.; Menna, M. Isolation and structure determination of aplidinones A-C from the Mediterranean ascidian Aplidium conicum: A successful regiochemistry assignment by quantum mechanical 13C NMR chemical shift Calculations. Eur. J. Org. Chem. 2005, 2005, 5024-5030.
41. Aiello, A.; Fattorusso, E.; Luciano, P.; Macho, A.; Menna, M.; Muñoz, E. Antitumor effects of two novel naturally occurring terpene quinones isolated from the Mediterranean ascidian Aplidium conicum. J. Med. Chem. 2005, 48, 3410-3416. (Pubitemid 40628058)
42. Carbone, A.; Lucas, C.L.; Moody, C.J. Biomimetic synthesis of the apoptosis-inducing thiazinoquinone thiaplidiaquinone A. J. Org. Chem. 2012, 77, 9179-9189.
43. Khalil, I.M.; Barker, D.; Copp, B.R. Biomimetic synthesis of thiaplidiaquinones A and B. J. Nat. Prod. 2012, 75, 2256-2260.
44. Aiello, A.; Fattorusso, E.; Luciano, P.; Menna, M.; Calzado, M.A.; Muñoz, E.; Bonadies, F.; Guiso, M.; Sanasi. M.F.; Cocco, G.; et al. Synthesis of structurally simplified analogues of aplidinone A, a pro-apoptotic marine thiazinoquinone. Bioorg. Med. Chem. 2010, 18, 719-727.
45. De Rosa, S.; de Giulio, A.; Iodice, C. Biological effects of prenylated hydroquinones: Structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays. J. Nat. Prod. 1994, 57, 1711-1716.
46. Muller, W.E.G.; Maidhof, A.; Zahn, R.K.; Schroder, H.C.; Gasic, M.J.; Heidemann, D.; Bernd, A.; Kurelec, B.; Eich, E.; Seibert, G. Potent antileukemic activity of the novel cytostatic agent avarone and its analogs in vitro and in vivo. Cancer Res. 1985, 45, 4822-4826.
47. Kondracki, M.L.; Guyot, M. Biologically active quinone and hydroquinone sesquiterpenoids from the sponge Smenospongia sp. Tetrahedron 1989, 45, 1995-2004. (Pubitemid 19089601)
48. Hamann, M.T.; Scheuer, P.J.; Kelly-Borges, M. Biogenetically diverse, bioactive constituents of a sponge, order Verongida: Bromotyramines and sesquiterpene-shikimate derived metabolites. J. Org. Chem. 1993, 58, 6565-6569. (Pubitemid 24011161)
49. Alvi, K.A.; Diaz, M.C.; Crews, P.; Slate, D.L.; Lee, R.H.; Moretti, R. Evaluation of new sesquiterpene quinones from two Dysidea sponge species as inhibitors of protein tyrosine kinase. J. Org. Chem. 1992, 57, 6604-6607. (Pubitemid 23017304)
50. Loya, S.; Tal, R.; Kashman, Y.; Hizi, A. Illimaquinone, a selective inhibitor of the RNase H activity of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 1990, 34, 2009-2012. (Pubitemid 20290304)
51. Gordaliza, M. Cytotoxic terpene quinones from marine sponges. Mar. Drugs 2010, 8, 2849-2870.
52. Benites, J.; Valderrama, J.A.; Rivera, F.; Rojo, L.; Campos, N.; Pedro, M.; Nascimento, M.S.J. Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines. Bioorg. Med. Chem. 2008, 16, 862-868 and all previous parts.
53. Ishibashi, M.; Ohizumi, Y.; Cheng, J.-F.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J . Metachromins A and B, Novel antineoplastic sesquiterpenoids from the okinawan sponge Hippospongia cf. metachromia. J. Org. Chem. 1988, 53, 2855-2858.
54. Kobayashi, J.; Murayama, T.; Ohizumi, Y.; Ohta, T.; Nozoe, S.; Sasaki, T. Metachromin C, a new cytotoxic sesquiterpenoid from the okinawan marine sponge Hippospongia metachromia . J. Nat. Prod. 1989, 52, 1173-1176. (Pubitemid 19270620)
55. Kobayashi, J.; Naitoh, N.; Sasaki, T.; Shigemori, H. Metachromins D-H, new cytotoxic sesquiterpenoids from the okinawan marine sponge Hippospongia metachromia. J. Org. Chem. 1992, 57, 5773-5776.
56. Takahashi, Y.; Kubota, T.; Fromont, J.; Kobayashi, J. Metachromins L-Q, new sesquiterpenoid quinones with an aminoacid residue from sponge Spongia sp. Tetrahedron 2007, 63, 8770-8773. (Pubitemid 47096649)
57. Takahashi, Y.; Yamada, M.; Kubota, T.; Fromont, J.; Kobayashi, J. Metachromins R-T, new sesquiterpenoids from marine sponge Spongia sp. Chem. Pharm. Bull. 2007, 55, 1731-1733. (Pubitemid 350232546)
58. Ovenden, S.P.B.; Nielson, J.L.; Liptrot, C.H.; Willis, R.H.; Tapiolas, D.M.; Wright, A.D.; Motti, C.A. Metachromins U-W: Cytotoxic merosesquiterpenoids from an Australian specimen of the sponge Thorecta reticulata. J. Nat. Prod. 2011, 74, 1335-1338.
59. Minale, L.; Riccio, R.; Sodano, G. Avarol, a novel sesquiterpenoid hydroquinone with a rearranged drimane skeleton from the sponge Disidea avara. Tetrahedron Lett. 1974, 38, 3401-3404.
60. Cimino, G.; de Rosa, S.; de Stefano, S.; Cariello, L.; Zanetti, L. Structure of two biologically active sesquiterpenoid amino-quinones from the marine sponge Dysidea avara. Experientia 1982, 38, 896.
61. De Rosa, S.; Minale, L.; Riccio, R.; Sodano, G. The absolute configuration of avarol, a rearranged sesquiterpenoid hydroquinone from a marine sponge. J. Chem. Soc. Perkin Trans. 1 1976, 1408-1414, doi:10.1039/ P19760001408.
62. Giordano, F.; Puliti, R. Structure of the 2,5-dimethyl ether of avarol, a sesquiterpenoid hydroquinone from the marine sponge Dysidea avara. Acta Cryst. 1987, C43, 985-988.
63. Müller, W.E.G.; Sobel, C.; Sachsse, W.; Diehl-Seifert, B.; Zahn, R.K.; Eich, E.; Kljajić, Z.; Schröder, H.C. Biphasic and differential effects of the cytostatic agents avarone and avarol on DNA metabolism of human and murine T and B lymphocytes. Eur. J. Cancer Clin. Oncol. 1986, 22, 473-476.
64. Müller, W.E.G.; Sobel, C.; Diehl-Seifert, B.; Maidhof, A.; Schöder, H.C. Influence of the antileukemic and anti-human immunodeficiency virus agent avarol on selected immune responses in vitro and in vivo. Biochem. Pharmacol. 1987, 36, 1489-1494.
65. Cozzolino, R.; de Giulio, A.; de Rosa, S.; Strazzullo, G.; Gašič, M.J.; Sladić, D.; Zlatović, M. Biological activities of avarol derivatives, 1. Amino derivatives. J. Nat. Prod. 1990, 53, 699-702. (Pubitemid 20311273)
66. Sarin, P.S.; Sun, D.; Thornton, A.; Müller, W.E.G. Inhibition of replication of the etiologic agent of acquired immune deficiency syndrome (human T-lymphotropic retrovirus/lymphadenopathy-associated virus) by avarol and avarone. J. Natl. Cancer Inst. 1987, 78, 663-666. (Pubitemid 17063622)
67. Schroeder, H.C.; Sarin, P.S.; Rottmann, M.; Wenger, R.; Maidhof, A.; Renneisen, K.; Muller, W.E.G. Differential modulation of host cell and HIV gene expression by combinations of Avarol and AZT in vitro. Biochem. Pharmacol. 1988, 37, 3947-3952.
68. Schroeder, H.C.; Wenger, R.; Gerner, H.; Reuter, P.; Kuchino, Y.; Sladic, D.; Muller, W.E.G. Suppression of the modulatory effects of the antileukemic and anti-human immunodeficiency virus compound avarol on gene expression by tryptophan. Cancer Res. 1989, 49, 2069-2076. (Pubitemid 19106516)
69. Schatton, W.; Schatton, M.; Pietschmamm, R. Method for the Preparation of Compositions with High Avarol Content from Sponge and Use for the Prevention and Treatment of Psoriasis and Tumors. Eur. Pat. Appl. EP 1391197 A1, 25 February 2004.
70. Iguchi, K.; Sahashi, A.; Khono, J.; Yamada, Y. New sesquiterpenoid hydroquinone and quinones from the Okinawan marine sponge (Dysidea sp.). Chem. Pharm. Bull. 1990, 38, 1121-1123. (Pubitemid 20290792)
71. Hirsch, S.; Rudi, A.; Kashman, Y.; Loya, Y. New avarone and avarol derivatives from the marine sponge Dysidea cinerea. J. Nat. Prod. 1991, 54, 92-97.
72. Crispino, A.; de Giulio, A.; de Rosa, S.; Strazzullo, G. A new bioactive derivative of avarol from the marine sponge Dysidea avara. J. Nat. Prod. 1989, 52, 646-648. (Pubitemid 19171569)
73. De Giulio, A.; de Rosa, S.; di Vincenzo, G.; Strazzullo, G. Further bioactive derivative of avarol from Dysidea avara . Tetrahedron 1990, 46, 7971-7976. (Pubitemid 20383659)
74. Loya, S.; Tal, R.; Hizi, A.; Issacs, S.; Kashman, Y.; Loya, Y. Hexaprenoid hydroquinones, novel inhibitors of the reverse transcriptase of human immunodeficiency virus type 1. J. Nat. Prod. 1993, 56, 2120-2125. (Pubitemid 24034020)
75. Schmitz, F.J.; Lakshmi, V.; Powell, D.R.; van der Helm, D. Arenarol and arenarone: Sesquiterpenoids with rearranged drimane skeletons from the marine sponge Dysidea arenaria. J. Org. Chem. 1984, 49, 241-244.
76. Luibrand, R.T.; Erdman, T.R.; Vollmer, J.J.; Scheuer, P.J.; Finer, J.; Clardy, J. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge. Tetrahedron 1979, 35, 609-612.
77. Liu, H.; Wang, G.; Namikoshi, M.; Kobayashi, H.; Yao, X.; Cai, G. Sesquiterpene quinones from a marine sponge Hippospongia sp. that inhibit maturation of starfish oocytes and induce cell cycle arrest with HepG2 cells. Pharm. Biol. 2006, 44, 522-527. (Pubitemid 44582018)
78. Cartè, B.; Rose, C.B.; Faulkner, D.J. 5-Epi-Ilimaquinone, a metabolite of the sponge Fenestraspongia sp. J. Org. Chem. 1985, 50, 2785-2787.
79. Kazlauskas, R.; Murphy, P.T.; Warren, R.G.; Wells, R.J.; Blount, J.F. New quinones from a dictyoceratid sponge. Aust. J. Chem. 1978, 31, 2685-2697.
80. Rodriguez, J.; Quinoa, H.; Riguera, R.; Peters, B.M.; Abrell, L.M.; Crews, P. The structures and stereochemistry of cytotoxic sesquiterpene quinones from Dactylospongia elegans. Tetrahedron 1992, 48, 6667-6680.
81. Capon, R.J.; MacLeod, J.K. Revision of the absolute stereochemistry of ilimaquinone. J. Org. Chem. 1987, 52, 5059-5060.
82. Nambiar, M.P.; Wu, H.C. Ilimaquinone inhibits the cytotoxicities of ricin, diphtheria toxin, and other protein toxins in Vero cells. Exp. Cell Res. 1995, 219, 671-678.
83. Takizawa, P.A.; Yucel, J.K.; Veit, B.; Faulkner, D.J.; Deerinck, T.; Soto, G.; Ellisman, M.; Malhotra, V. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone. Cell 1993, 73, 1079-1090. (Pubitemid 23180483)
84. Casaubon, R.L.; Snapper, M.L. S-adenosylmethionine reverses ilimaquinone's vesiculation of the Golgi apparatus: A fluorescence study on the cellular interactions of ilimaquinone. Bioorg. Med. Chem. Lett. 2001, 11, 133-136. (Pubitemid 32099625)
85. Lu, P.-H.; Chueh, S.-C.; Kung, F.-L.; Pan, S.-L.; Shen, Y.-C.; Guh, J.-H. Illimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway. Eur. J. Pharmacol. 2007, 556, 45-54. (Pubitemid 46074004)
86. Guzmán, F.S.; Copp, B.R.; Mayne, C.L.; Concepcion, G.P.; Mangalindan, G.C.; Barrows, L.R.; Ireland, C.M. Bolinaquinone: A novel cytotoxic sesquiterpene hydroquinone from Philippine Dysidea sponge. J. Org. Chem. 1998, 63, 8042-804.
87. Li, Y.; Zhang, Y.; Shen, X.; Guo, Y. A novel sesquiterpene quinone from Hainan sponge Dysidea villosa . Bioorg. Med. Chem. Lett. 2009, 19, 390-392.
88. Jankam, A.; Somerville, M.J.; Hooper, J.N.A.; Brecknell, D.J.; Suksamrarna, A.; Garson, M.J. Dactylospongiaquinone, a new meroterpenoid from the Australian marine sponge Dactylospongia n. sp. Tetrahedron 2007, 63, 1577-1582. (Pubitemid 46074115)
89. Yong, K.W.L.; Jankam, A.; Hooper, J.N.A.; Suksamrarn, A.; Garson, M.J. Stereochemical evaluation of sesquiterpene quinones from two sponges of the genus Dactylospongia and the implication for enantioselective processes in marine terpene biosynthesis. Tetrahedron 2008, 64, 6341-6348.
90. Utkina, N.K.; Veselova, M.V. New sesquiterpene quinones from marine sponges of the order Dictyoceratida. Chem. Nat. Compd. 1990, 26, 37-40.
91. Swersey, J.C.; Barrows, L.R.; Ireland, C.M. Mamanuthaquinone: An antimicrobial and cytotoxic metabolite of Fasciospongia sp. Tetrahedron Lett. 1991, 32, 6687-6690.
92. Talpir, R.; Rudi, A.; Kashman, Y.; Loya, Y.; Hizi, A. Three new sesquiterpene hydroquinones from marine origin. Tetrahedron 1994, 50, 4179-4184. (Pubitemid 24117436)
93. Poigny, S.; Huor, T.; Guyot, M.; Samadi, M. Synthesis of (-)-hyatellaquinone and revision of absolute configuration of naturally occurring (+)-hyatellaquinone. J. Org. Chem. 1999, 64, 9318-9320. (Pubitemid 129599477)
94. Bernet, A.; Schröder, J.; Seifert, K. Total synthesis of the marine sesquiterpene quinones hyatellaquinone and spongiaquinone. Helv. Chim. Acta 2003, 86, 2009-2020. (Pubitemid 36899510)
95. McNamara, C.E.; Larsen, L.; Perry, N.B.; Harper, J.L.; Berridge, M.V.; Chia, E.W.; Kelly, M.; Webb, V.L. Anti-inflammatory sesquiterpene-quinones from the New Zealand sponge Dysidea cf. cristagalli. J. Nat. Prod. 2005, 68, 1431-1433. (Pubitemid 41499447)
96. Coval, S.J.; Conover, M.A.; Mierzwa, R.; King, A.; Puar, M.S.; Phife, D.W.; Pai, J.K.; Burrier, R.E.; Ahn, H.S. Wiedendiol A and B, cholesteryl esther transfer protein inhibitors from marine sponge Xetospongia widenmayeri. Bioorg. Med. Chem. Lett. 1995, 5, 605-610.
97. Laube, T.; Bernet, A.; Dahse, H.-M.; Jacobsen, I.D.; Seifert, K. Synthesis and pharmacological activities of some sesquiterpene quinones and hydroquinones. Bioorg. Med. Chem. 2009, 17, 1422-1427.
98. Venkateswarlu, Y.; Faulkner, D.J.; Steiner, J.L.R.; Corcoran, E.; Clardy, J. Smenochromenes, unusual macrocyclic sesquiterpene hydroquinone derivatives from a Seychelles sponge of the genus Smenospongia . J. Org. Chem. 1991, 56, 6271-6274.
99. Goclik, E.; Konig, G.M.; Wright, A.D.; Kaminsky, R. Pelorol from the tropical marine sponge Dactylospongia elegans. J. Nat. Prod. 2000, 63, 1150-1152.
100. Sullivan, B.; Djura, P.; McIntyre, D.E.; Faulkner, D.J. Antimicrobial constituents of the sponge Siphonodictyon coralliphagum. Tetrahedron 1981, 37, 979-982. (Pubitemid 11140813)
101. Sullivan, B.; Faulkner, D.J.; Matsumoto, G.K.; He, C.H.; Clardy, J. Metabolites of the burrowing sponge Siphonodictyon coralliphagum . J. Org. Chem. 1986, 51, 4568-4573.
102. Grube, A.; Assmann, M.; Lichte, E.; Sasse, F.; Pawlik, J.R.; Koeck, M. Bioactive metabolites from the caribbean sponge Aka coralliphagum. J. Nat. Prod. 2007, 70, 504-509.
103. Kondracki, M.L.; Guyot, M. Smenospongine: A cytotoxic and antimicrobial aminoquinone isolated from Smenospongia sp. Tetrahedron Lett. 1987, 28, 5815-5818. (Pubitemid 17165544)
104. Kwak, J.H.; Schmitz, F.J.; Kelly, M. Sesquiterpene quinols/quinones from the Micronesian sponge Petrosaspongia metachromia . J. Nat. Prod. 2000, 63, 1153-1156.
105. Aoki, S.; Kong, D.; Matsui, K.; Kobayashi, M. Smenospongine, a spongean sesquiterpene aminoquinone, induces erythroid differentiation in K562 cells. Anticancer Drugs 2004, 15, 363-369. (Pubitemid 38526761)
106. Aoki, S.; Kong, D.; Matsui, K.; Rachmat, R.; Kobayashi, M. Sesquiterpene aminoquinones, from a marine sponge, induce erythroid differentiation in human chronic myelogenous leukemia, K562 cells. Chem. Pharm. Bull. 2004, 52, 935-937. (Pubitemid 41701866)
107. Ovenden, S.P.B.; Nielson, J.L.; Liptrot, C.H.; Willis, R.H.; Tapiolas, D.M.; Wright, A.D.; Motti, C.A. Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans. J. Nat. Prod. 2011, 74, 65-68.
108. Augustijns, P.; Annaert, P.; Heylen, P.; van den Mooter, G.; Kinget, R. Drug absorption studies of prodrug esters using the Caco-2 model: Evaluation of ester hydrolysis and transepithelial transport. Int. J. Pharm. 1998, 166, 45-53. (Pubitemid 28239738)
109. Giannini, C.; Debitus, C.; Lucas, R.; Ubeda, A.; Paya, M.; Hooper, J.N.A.; D'Auria, M.V. New sesquiterpene derivatives from the sponge Dysidea species with a selective inhibitor profile against human phospholipase A2 and other leukocyte functions. J. Nat. Prod. 2001, 64, 612-615. (Pubitemid 32488678)
110. Zhang, Y.; Li, Y.; Guo, Y.; Jiang, H.; Shen, X. A sesquiterpene quinone, dysidine, from the sponge Dysidea villosa, activates the insulin pathway through inhibition of PTPases. Acta Pharmacol. Sin. 2009, 30, 333-345.
111. Diaz-Marrero, A.R.; Austin, P.; van Soest, R.; Matainaho, T.; Roskelley, C.D.; Roberge, M.; Andersen, R.J. Avinosol, a meroterpenoid-nucleoside conjugate with antiinvasion activity isolated from the marine sponge Dysidea sp. Org. Lett. 2006, 8, 3749-3752. (Pubitemid 44378354)
112. Rodriguez, A.D.; Yoshida, W.Y.; Scheuer, P.J. Popolohuanone A and B. Two new sesquiterpenoid aminoquinones from Pacific sponge Dysidea sp. Tetrahedron 1990, 46, 8025-8030.
113. Carney, J.R.; Scheuer, P.J. Popolohuanone E, a topoisomerase II inhibitor eith selective lung citotoxicity from Pohnpei sponge Dysidea sp. Tetrahedron Lett. 1993, 34, 3727-3730.
114. Utkina, N.K.; Denisenko, V.A.; Krasokhin, V.B. Sesquiterpenoidd aminoquinones from marine sponge Dysidea sp. J. Nat. Prod. 2010, 73, 788-791.
115. Shigemori, H.; Madono, T.; Sasaki, T.; Mikami, Y.; Kobayashi, J. Nakijiquinones A and B, new antifungal sesquiterpenoid quinones with an amino acid residue from an Okinawan marine sponge. Tetrahedron 1994, 50, 8347-8354. (Pubitemid 24227845)
116. Kobayashi, J.; Madono, T.; Shigemori, H. Nakijiquinones C and D, new sesquiterpenoid quinones with a hydroxy amino acid residue from a marine sponge inhibiting c-erbB-2 kinase. Tetrahedron 1995, 51, 10867-10874.
117. Takahashi, Y.; Kubota, T.; Kobayashi, J. Nakijiquinones E and F, new dimeric sesquiterpenoid quinones from marine sponge. Bioorg. Med. Chem. 2009, 17, 2185-2188.
118. Takahashi, Y.; Kubota, T.; Ito, J.; Mikami, Y.; Fromont, J.; Kobayashi, J. Nakijiquinones G-I, new sesquiterpenoid quinones from marine sponge. Bioorg. Med. Chem. 2008, 16, 7561-7564.
119. Takahashi, Y.; Ushio, M.; Kubota, T.; Yamamoto, S.; Fromont, J.; Kobayashi, J. Nakijiquinones J-R, sesquiterpenoid quinones with an amine residue from Okinawan marine sponges. J. Nat. Prod. 2010, 73, 467-471.
120. Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. Total synthesis and biological evaluation of the nakijiquinones. J. Am. Chem. Soc. 2001, 123, 11586-11593. (Pubitemid 33121779)
121. Mitome, H.; Nagasawa, T.; Miyaoka, H.; Yamada, Y.; van Soest, R.W.M. Dactyloquinones A and B, new sesquiterpenoid quinones from the okinawan marine sponge Dactylospongia elegans . J. Nat. Prod. 2001, 64, 1506-1508.
122. Mitome, H.; Nagasawa, T.; Miyaoka, H.; Yamada, Y.; van Soest, R.W.M. Dactyloquinones C, D and E novel sesquiterpenoid quinones, from the Okinawan marine sponge, Dactylospongia elegans. Tetrahedron 2002, 58, 1693-1696.
123. Djura, P.; Stierle, D.B.; Sullivan, B.; Faulkner, D.J.; Arnold, E.V.; Clardy, J. Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (≡Polyfibrospongia) echina . J. Org. Chem. 1980, 45, 1435-1441.
124. Wright, A.E.; Rueth, S.A.; Cross, S.S. An antiviral sesquiterpene hydroquinone from the marine sponge Strongylophora hartmani. J. Nat. Prod. 1991, 54, 1108-1111.
125. Cimino, G.; de Stefano, S.; Minale, L. Chromazonarol, a chroman-sesquiterpenoid from sponge Dysidea pallenscens. Experientia 1975, 31, 1117.
126. Barrero, A.J.; Alvarez-Manzaneda, E.J.; Herrador, M.M.; Chahboun, R.; Galera, P. Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328. (Pubitemid 29391515)
127. Song, F.; Fan, X.; Xu, X.; Wang, S.; Li, S.; Yang, Y.; Shi, J. Studies on chemical constituents of the brown alga Dictyopteris divaricata. Zhongguo Zhong Yao Za Zhi 2006, 31, 125-128.
128. Hideaki, I.; Kazuaki, I.; Hisashi, Y. A new artificial cyclase for poliprenoids: Enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione and (-)-11′-deoxytaondiol methyl ether. J. Am. Chem. Soc. 2004, 126, 11133-11123.
129. Ravi, B.N.; Perzanowski, H.P.; Ross, R.A.; Erdman, T.R.; Scheuer, P.J.; Finer, J.; Clardy, J. Recent research in marine natural products: The puupehenones. Pure Appl. Chem. 1979, 51, 1893-1900.
130. Nasu, S.S.; Yeung, B.K.S.; Hamann, M.T.; Scheuer, P.J.; Kelly-Borges, M.; Goins, K. Puupehenone-related metabolites from two Hawaiian sponges, Hyrtios spp. J. Org. Chem. 1995, 60, 7290-7292.
131. Bourguet-Kondracki, M.L.; Debitus, C.; Guyot, M. Dipuupehedione, a cytotoxic new red dimer from a New Caledonian marine sponge Hyrtios sp. Tetrahedron Lett. 1996, 37, 3861-3864. (Pubitemid 26169851)
132. Bourguet-Kondracki, M.L.; Lacombe, F.; Guyot, M. Methanol adduct of puupehenone, a biologically active derivative from the marine sponge Hyrtios species. J. Nat. Prod. 1999, 62, 1304-1305. (Pubitemid 29463335)
133. Piña, I.C.; Sanders, M.L.; Crews, P. Puupehenone congeners from an Indo-Pacific Hyrtios sponge. J. Nat. Prod. 2003, 66, 2-6. (Pubitemid 36150806)
134. Ciavatta, M.L.; Gresa, M.P.L.; Gavagnin, M.; Romero, V.; Melck, D.; Manzo, E.; Guo, Y.W.; van Soest, R.; Cimino, G. Studies on puupehenone- metabolites of a Dysidea sp.: Structure and biological activity. Tetrahedron 2007, 63, 1380-1384. (Pubitemid 44969420)
135. Robinson, S.J.; Hoobler, E.K.; Riener, M.; Loveridge, S.T.; Tenney, K.; Valeriote, F.A.; Holman, T.R.; Crews, P. Using enzyme assays to evaluate the structure and bioactivity of sponge-derived meroterpenes. J. Nat. Prod. 2009, 72, 1857-1863.
136. Xu, W.H.; Ding, Y.; Jacob, M.R.; Agarwal, A.K.; Clark, A.M.; Ferreira, D.; Liang, Z.S.; Li, X.C. Puupehanol, a sesquiterpene-dihydroquinone derivative from the marine sponge Hyrtios sp. Bioorg. Med. Chem. Lett. 2009, 19, 6140-6143.
137. Amade, P.; Chevelot, L.; Perzanowski, H.P.; Scheuer, P.J. A dimer of puupehenone. Helv. Chim. Acta 1983, 66, 1672-1675.
138. Castro, M.E.; González-Iriarte, M.; Barrero, A.F.; Salvador-Tormo, N.; Muñoz-Chápuli, R.; Medina, M.A.; Quesada, A.R. Study of puupehenone and related compounds as inhibitors of angiogenesis. Int. J. Cancer 2004, 110, 31-38. (Pubitemid 38507201)
139. El Sayed, K.A.; Bartyzel, P.; Shen, X.; Perry, T.L.; Zjawiony, J.K.; Hamann, M.T. Marine natural products as antituberculosis agents. Tetrahedron 2000, 56, 949-953. (Pubitemid 30094161)
140. Douat-Casassus, C.; Marchand-Geneste, N.; Diez, E.; Aznar, C.; Picard, P.; Geoffre, S.; Huet, A.; Bourguet-Kondracki, M.L.; Gervois, N.; Jotereau, F.; et al. Covalent modification of a melanoma-derived antigenic peptide with a natural quinone methide. Preliminary chemical, molecular modelling and immunological evaluation studies. Mol. BioSyst. 2006, 2, 240-249.
141. Utkina, N.K.; Denisenko, V.A.; Krasokhin, V.B. Diplopuupehenone, a new unsymmetrical puupehenone-related dimer from the marine sponge Dysidea sp. Tetrahedron Lett. 2011, 52, 3765-3768.
142. Quideau, S.; Lebon, M.; Lamidey, A.M. Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route. Org. Lett. 2002, 4, 3975-3978.
143. Chan, J.A.; Freyer, A.J.; Carté, B.K.; Hemling, M.E.; Hofmann, G.H.; Mattern, M.R.; Mentzer, M.A.; Westley, J.W. Protein kinase C inhibitors: Novel spitosequiterpene aldehydes from a marine sponge Aka (=Siphonodictyon) coralliphagum. J. Nat. Prod. 1994, 57, 1543-1548.
144. Utkina, N.K.; Denisenko, V.A.; Scholokova, O.V.; Virovaya, M.V.; Prokof'eva, N.G. Cyclosmenospongine, a new sesquiterpenoid aminoquinone from an Australian marine sponge Spongia sp. Tetrahedron Lett. 2003, 44, 101-102. (Pubitemid 35453863)
145. Utkina, N.K.; Denisenko, V.A.; Scholokova, O.V.; Makarchenko, A.E. Determination of the absolute stereochemistry of cyclosmenospongine. J. Nat. Prod. 2003, 66, 1263-1265. (Pubitemid 37204235)
146. Mitome, H.; Nagasawa, T.; Miyaoka, H.; Yamada, Y.; van Soest, R.W.M. A new sesquiterpenoid quinone and other related compounds from the okinawan marine sponge Dactylospongia elegans . J. Nat. Prod. 2003, 66, 46-50.
147. Killday, K.B.; Wright, A.E. Bis(Sulfato)-cyclosiphonodictyol A, a new disulfated sesquiterpene-hydroquinone from a deep water collection of the marine sponge Siphonodictyon coralliphagum. J. Nat. Prod. 1995, 58, 958-960.
148. Patil, A.D.; Freyer, A.J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A.J.; Johnson, R.K. Frondosins, five new sesquiterpene hydroquinone derivatives with novel skeletons from the sponge Dysidea frondosa: Inhibitors of interleukin-8 receptors. Tetrahedron 1997, 53, 5047-5060. (Pubitemid 27144318)
149. Jiao, W.-H.; Huang, X.-J.; Yang, J.-S.; Yang, F.; Piao, S.-J.; Gao, H.; Li, J.; Ye, W.-C.; Yao, X.; Chen, W.-S.; et al. Dysidavarones A-D, new sesquiterpene quinones from the marine sponge Dysidea avara. Org. Lett. 2012, 14, 202-205.
150. Nakamura, H.; Kobayashi, J.; Kobayashi, M.; Ohizumi, Y.; Hirata, Y. Xestoquinone. A novel cardiotonic marine natural product isolated from the Okinawan sea sponge Xestospongia sapra . Chem. Lett. 1985, 6, 713-716.
151. Roll, D.M.; Scheuer, P.J. Halenaquinone, a pentacyclic polyketide from a marine sponge. J. Am. Chem. Soc. 1983, 105, 6177-6178.
152. Cao, S.; Foster, C.; Brisson, M.; Lazo, J.S.; Kingston, D.G.I. Halenaquinone and xestoquinone derivatives, inhibitors of Cdc25B phosphatase from a Xestospongia sp. Bioorg. Med. Chem. 2005, 13, 999-1003. (Pubitemid 40164583)
153. Concepcion, G.P.; Foderaro, T.A.; Eldredge, G.S.; Lobkovsky, E.; Clardy, J.; Barrows, L.R.; Ireland, C.M. Topoisomerase II-mediated DNA Cleavage by adocia- and xestoquinones from the philippine sponge Xestospongia sp. J. Med. Chem. 1995, 38, 4503-4507.
154. Schmitz, F.J.; Bloor, S.J. Xesto- and halenaquinone derivatives from a sponge, Adocia sp., from truk lagoon. J. Org. Chem. 1988, 53, 3922-3925.
155. Desoubzdanne, D.; Marcourt, L.; Raux, R.; Chevalley, S.; Dorin, D.;
156. Zhang, H.; Khalil, Z.G.; Capon, R.J. Fascioquinols A-F: Bioactive meroterpenes from a deep-water southern Australian marine sponge Fasciospongia sp. Tetrahedron 2011, 67, 2591-2595.
157. Standish, A.J.; Salim, A.A.; Zhang, H.; Capon, R.J.; Morona, R. Chemical inhibition of bacterial protein tyrosine phosphatase suppresses capsule production. PLoS One 2012, 7, e36312.
158. Standish, A.J.; Salim, A.A.; Capon, R.J.; Morona, R. Dual inhibition of DNA polymerase PolC and protein tyrosine phosphatase CpsB uncovers a novel antibiotic target. Biochem. Biophys. Res. Commun. 2013, 430, 167-172.
159. Tasdemir, D.; Concepción, G.P.; Mangalindan, G.C.; Harper, M.K.; Hajduc, E.; Ireland, C.M. New terpenoids from a Cacospongia sp. from the Philippines. Tetrahedron 2000, 56, 9025-9030.
160. Murray, L.M.; Johnson, A.; Diaz, M.C.; Crews, P. Geographic variation in the tropical marine sponge Jaspis cf. johnstoni : An unexpected source of new terpene-benzenoids. J. Org. Chem. 1997, 62, 5638-5641. (Pubitemid 127494918)
161. Rubio, B.K.; van Soest, R.W.M.; Crews, P. Extending the record of meroditerpenes from Cacospongia marine sponges. J. Nat. Prod. 2007, 70, 628-631. (Pubitemid 46797868)
162. Loll, P.J.; Axelsen, P.H. The structural biology of molecular recognition by vancomycin. Annu. Rev. Biophys. Biomol. Struct. 2000, 29, 265-289. (Pubitemid 30599595)
163. Carroll, J.; Jonsson, E.N.; Ebel, R.; Hartman, M.S.; Holman, T.R.; Crews, P. Probing sponge-derived terpenoids for human 15-lipoxygenase inhibitors. J. Org. Chem. 2001, 66, 6847-6851. (Pubitemid 32983063)
164. Williams, D.E.; Telliez, J.B.; Liu, J.; Tahir, A.; van Soest, R.; Andersen, R.J. Meroterpenoid MAPKAP (MK2) inhibitors isolated from the Indonesian marine sponge Acanthodendrilla sp. J. Nat. Prod. 2004, 67, 2127-2129. (Pubitemid 40092574)
165. Cichewicz, R.H.; Kenyon, V.A.; Whitman, S.; Morales, N.M.; Arguello, J.F.; Holman, T.R.; Crews, P. Redox inactivation of human 15-lipoxygenase by marine-derived meroditerpenes and synthetic chromanes: Archetypes for a unique class of selective and recyclable inhibitors. J. Am. Chem. Soc. 2004, 126, 14910-14920. (Pubitemid 39532173)
166. Braekman, J.C.; Daloze, D.; Hulot, G.; Tursch, B.; Declercq, J.P.; Germain, G.; van Meerssche, M. Chemical studies of marine invertebrates. XXXVII. Three novel meroditerpenoids from the sponge Strongylophora durissima. Bull. Soc. Chim. Belg. 1978, 87, 917-926.
167. Salva, J.; Faulkner, D.J. Metabolites of the sponge Strongylophora durissima from Maricaban Island, Philippines. J. Org. Chem. 1990, 55, 1941-1943.
168. Balbin-Oliveros, M.; Edrada, R.; Proksch, P.; Wray, V.; Witte, W.M.; van Soest, R.W.M. A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus Strongylophora. J. Nat. Prod. 1998, 61, 948-952.
169. Liu, H.; Namikoshi, M.; Akano, K.; Kobayashi, H.; Nagai, H.; Yao, X. Seven new meroditerpenoids, from the marine sponge Strongylophora strongylata, that inhibited the maturation of starfish oocytes. J. Asian Nat. Prod. Res. 2005, 7, 661-670. (Pubitemid 40909336)
170. Warabi, K.; Patrick, B.O.; Austin, P.; Roskelley, C.D.; Roberge, M.; Andersen, R.J. Strongylophorine-26, an inhibitor of cancer cell invasion: SAR revealed by synthesis of analogues. J. Nat. Prod. 2007, 70, 736-740. (Pubitemid 46953591)
171. McHardy, L.M.; Warabi, K.; Andersen, R.J.; Roskelley, C.D.; Roberge, M. Strongylophorine-26, a Rho-dependent inhibitor of tumor cell invasion that reduces actin stress fibers and induces nonpolarized lamellipodial extensions. Mol. Cancer Ther. 2005, 4, 772-778. (Pubitemid 40767121)
172. Shen, Y.C.; Prakash, C.V. Two new acetylenic derivatives and a new meroditerpenoid from a Taiwanese marine sponge Strongylophora durissima. J. Nat. Prod. 2000, 63, 1686-1688. (Pubitemid 32038619)
173. Warabi, K.; McHardy, L.M.; Matainaho, L.; van Soest, R.W.M.; Roskelley, C.D.; Roberge, M.; Andersen, R.J. Strongylophorine-26, a new meroditerpenoid isolated from the marine sponge Petrosia (Strongylophora) corticata that exhibits anti-invasion activity. J. Nat. Prod. 2004, 67, 1387-1389. (Pubitemid 39145647)
174. Mohammed, K.A.; Jadulco, R.C.; Bugni, T.S.; Harper, M.K.; Sturdy, M.; Ireland, C.M.; Strongylophorines: Natural product inhibitors of hypoxia-inducible factor-1 transcriptional pathway. J. Med. Chem. 2008, 51, 1402-1405.
175. Sasaki, S.; Tozawa, T.; van Wagoner, R.M.; Ireland, C.M.; Harper, M.K.; Satoh, T. Strongylophorine-8, a pro-electrophilic compound from the marine sponge Petrosia (Strongylophora) corticata, provides neuroprotection through Nrf2/ARE pathway. Biochem. Biophys. Res. Commun. 2011, 415, 6-10.
176. Bae, J.M.; Jeon, J.E.; Lee, Y.J.; Lee, H.S.; Sim, C.J.; Oh, K.B.; Shin, J.H. Sesterterpenes from the tropical sponge Coscinoderma sp. J. Nat. Prod. 2011, 74, 1805-1811.
177. Alea, G.V.; Carroll, A.R.; Bowden, B.F. Coscinoquinol, a new cytotoxic sesterterpene from a dictyoceratid sponge, Coscinoderma sp. Aust. J. Chem. 1994, 47, 191-194.
178. Kernan, M.R.; Faulkner, D.J. Sesterterpene sulfates from a sponge of the family Halichondriidae. J. Org. Chem. 1988, 53, 4574-4578.
179. Loukaci, A.; Le Saout, I.; Samadi, M.; Leclerc, S.; Damiens, E.; Meijer, L.; Debitus, C.; Guyot, M. Coscinosulfate, a CDC25 phosphatase inhibitor from the sponge Coscinoderma mathewsi. Bioorg. Med. Chem. 2001, 9, 3049-3054.
180. Kimura, J.; Ishizuka, E.; Nakao, Y.; Yoshida, W.Y.; Scheuer, P.J.; Kelly-Borges, M. Isolation of 1-methylherbipoline salts of halisulfate-1 and of suvanine as serine protease inhibitors from a marine sponge, Coscinoderma mathewsi. J. Nat. Prod. 1998, 61, 248-250. (Pubitemid 28136780)
181. Lee, H.S.; Lee, T.H.; Yang, S.H.; Shin, H.J.; Shin, J.; Oh, K.B. Sesterterpene sulfates as isocitrate lyase inhibitors from tropical sponge Hippospongia sp. Bioorg. Med. Chem. Lett. 2007, 17, 2483-2486.
182. Shin, D.S.; Lee, T.H.; Lee, H.S.; Shin, J.; Oh, K.B. Inhibition of infection of the rice blast fungus by halisulfate 1, an isocitrate lyase inhibitor. FEMS Microbiol. Lett. 2007, 272, 43-47.
183. De Marino, S.; Festa, C.; D'Auria, M.V.; Bourguet-Kondracki, M.-L.; Petek, S.; Debitus, C.; Andres, R.M.; Terencio, M.C.; Paya, M.; Zampella, A. Coscinolactams A and B: New nitrogen-containing sesterterpenoids from the marine sponge Coscinoderma mathewsi exerting anti-inflammatory properties. Tetrahedron 2009, 65, 2905-2909.
184. Baratte, B.; Meijer, L.; Galaktionov, K.; Beach, D. Screening for antimitotic compounds using the cdc25 tyrosine phosphatase, an activator of the mitosis-inducing p34cdc2/cyclin Bcdc13 protein kinase. Anticancer Res. 1992, 12, 873-880.
185. Isaacs, S.; Kashman, Y. Shaagrockol B and C; two hexaprenylhydroquinone disulfates from the Red Sea sponge Toxiclona toxius. Tetrahedron Lett. 1992, 33, 2227-2230.
186. Isaacs, S.; Hizi, A.; Kashman, Y. Toxicols A-C and toxiusol-New bioactive hexaprenoid hydroquinones from Toxiclona toxius . Tetrahedron 1993, 49, 4275-4282.
187. Blackburn, C.L.; Hopmann, C.; Sakowicz, R.; Berdelis, M.S.; Goldstein, L.S.B.; Faulkner, D.J. Adociasulfates 1-6, inhibitors of kinesin motor proteins from the sponge Haliclona (aka Adocia) sp. J. Org. Chem. 1999, 64, 5565-5570.
188. Blackburn, C.L.; Faulkner, D.J. Adociasulfate 10, a new merohexaprenoid sulfate from the sponge Haliclona (aka Adocia) sp. Tetrahedron 2000, 56, 8429-8432.
189. Kalaitzis, J.A.; Leone, P.A.; Harris, L.; Butler, M.S.; Ngo, A.; Hooper, J.N.A.; Quinn, R.J. Adociasulfates 1, 7, and 8: New bioactive hexaprenoid hydroquinones from the marine sponge Adocia sp. J. Org. Chem. 1999, 64, 5571-5574.
190. West, L.M.; Faulkner, D.J. Hexaprenoid hydroquinones from the sponge Haliclona (aka Adocia) sp. J. Nat. Prod. 2006, 69, 1001-1004. (Pubitemid 44252207)
191. Kalaitzis, J.A.; Quinn, R.J. Adociasulfate-9, a new hexaprenoid hydroquinone from the Great Barrier Reef sponge Adocia aculeata. J. Nat. Prod. 1999, 62, 1682-1684. (Pubitemid 30030616)
192. Barton, N.R.; Goldstein, L.S.B. Going mobile: Microtubule motors and chromosome segregation . Proc. Natl. Acad. Sci. USA 1996, 93, 1735-1742. (Pubitemid 26079826)
193. Hirokawa, N. Kinesin and dynein superfamily proteins and the mechanism of organelle transport. Science 1998, 279, 519-526. (Pubitemid 28067273)
194. Crews, P.; Harrison, B. New triterpene-ketides (merotriterpenes), haliclotriol A and B, from an indo-pacific Haliclona sponge. Tetrahedron 2000, 56, 9039-9046.
195. Trianto, A.; Hermawan, I.; de Voogd, N.J.; Tanaka, J. Halioxepine, a new meroditerpene from an Indonesian sponge Haliclona sp. Chem. Pharm. Bull. 2011, 59, 1311-1313.
196. Fisch, K.M.; Böhm, V.; Wright, A.D.; König, G.M. Antioxidative meroterpenoids from the brown alga Cystoseira crinite. J. Nat. Prod. 2003, 66, 968-975. (Pubitemid 36909845)
197. Williams, D.E.; Steinø, A.; de Voogd, N.J.; Mauk, A.G.; Andersen, R.J. Halicloic acids A and B isolated from the marine sponge Haliclona sp. collected in the Philippines inhibit indoleamine 2,3-dioxygenase. J. Nat. Prod. 2012, 75, 1451-1458.
198. Fukami, A.; Ikeda, Y.; Kondo, S.; Naganawa, H.; Takeuchi, T.; Furuya, S.; Hirabayashi, Y.; Shimoike, K.; Hosaka, S.; Watanabe Y.; Umezawa, K. Akaterpin, a novel bioactive triterpene from the marine sponge Callyspongia sp. Tetrahedron Lett. 1997, 38, 1201-1202. (Pubitemid 27076183)
199. Gray, C.A.; de Lira, S.P.; Silva, M.; Pimenta, E.F.; Thiemann, O.H.; Oliva, G.; Hajdu, E.; Andersen, R.J.; Berlinck, R.G.S. Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase. J. Org. Chem. 2006, 71, 8685-8690. (Pubitemid 44721937)
200. Hooper, G.J.; Davies-Coleman, M.T. Sesquiterpene hydroquinones from the South African soft coral Alcyonium fauri. Tetrahedron Lett. 1995, 36, 3265-3268.
201. Sheu, J.H.; Su, J.H.; Sung, P.J.; Wang, G.H.; Dai, C.F. Novel meroditerpenoid-related metabolites from the formosan soft coral Nephthea chabrolii. J. Nat. Prod. 2004, 67, 2048-2052.
202. Su, J.H.; Ahmed, A.F.; Sung, P.J.; Wu, Y.C.; Sheu, J.H. Terpenoid-related metabolites from a formosan soft coral Nephthea Chabrolii . J. Nat. Prod. 2005, 68, 1651-1655.
203. Su, J.H.; Dai, C.F.; Huang, H.H.; Wu, Y.C.; Sung, P.J.; Hsu, C.H.; Sheu, J.H. Terpenoid-related metabolites from a Formosan soft coral Nephthea chabrolii . Chem. Pharm. Bull. 2007, 55, 594-597.
204. Chen, J.W.; Luo, Y.L.; Hwang, M.J.; Peng, F.C.; Ling, K.H.J. Territrem B, a tremorgenic mycotoxin that inhibits acetylcholinesterase with a noncovalent yet irreversible binding mechanism. Biol. Chem. 1999, 274, 34916-34923.
205. Cueto, M.; MacMillan, J.B.; Jensen, P.R.; Fenical, W. Tropolactones A-D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus. Phytochemistry 2006, 67, 1826-1831.
206. Cohen, E.; Koch, L.; Myint Thu, K.; Rahamim, Y.; Aluma, Y.; Ilan, M.; Yarden, O.; Carmeli, S. Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel. Bioorg. Med. Chem. 2011, 19, 6587-6593.
207. Lopez-Gresa, M.P.; Cabedo, N.; Gonzalez-Mas, M.C.; Ciavatta, M.L.; Avila, C.; Primo, J. Terretonins E and F, inhibitors of the mitochondrial respiratory chain from the marine-derived fungus Aspergillus insuetus. J. Nat. Prod. 2009, 72, 1348-1351.
208. Zhou, Y.; Mándi, A.; Debbab, A.; Wray, V.; Schulz, B.; Müller, W.E.G.; Lin, W.H.; Proksch, P.; Kurtán, T.; Aly, A.H. New austalides from the sponge-associated fungus Aspergillus sp. Eur. J. Org. Chem. 2011, 2011, 6009-6019.
209. Bugni, T.S.; Abbanat, D.; Bernan, V.S.; Malese, W.M.; Greenstein, M.; van Wagoner, R.; Ireland, C.M. Yanuthones: Novel metabolites from a marine isolate of Aspergillus niger. J. Org. Chem. 2000, 65, 7195-7200.
210. Sanchez, J.F.; Somoza, A.D.; Kellerc, N.P.; Wang, C.C.C. Advances in Aspergillus secondary metabolite research in the post-genomic era. Nat. Prod. Rep. 2012, 29, 351-371.
211. Lo, H.; Entwistle, R.; Guo, C.; Ahuja, M.; Szewczyk, E.; Hung, J.; Chiang, Y.; Oakley, B.R.; Wang, C.C.C. Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans. J. Am. Chem. Soc. 2012, 134, 4709-4720.
212. Guo, C.; Knox, B.P.; Chiang, Y.; Lo, H.; Sanchez, J.F.; Lee, K.; Oakley, B.R.; Bruno, K.S.; Wang, C.C.C. Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid Terretonin. Org. Lett . 2012, 14, 5684-5687.