Cytotoxic terpene quinones from marine sponges

Marine Drugs

Volumn 8, Issue 12, 2010, Pages 2849-2870

  Gordaliza, Marina ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Avarol; Avarone; Cytotoxicity; Terpene hydroquinone; Terpene quinone

Indexed keywords

2',5' O (4 BROMOBENZOYL)AVAROL; 3',4' (ETHYLENEDITHIO)AVARONE; 4' (METHYLAMINO)AVARONE; ANTINEOPLASTIC AGENT; AVAROL; AVARONE; GLYCINYLILIMAQUINONE; HYDROQUINONE; ILIMAQUINONE; NAKIJIQUINONE A; NAKIJIQUINONE B; NAKIJIQUINONE C; NAKIJIQUINONE D; NAKIJIQUINONE G; NAKIJIQUINONE H; NAKIJIQUINONE I; NAKIJIQUINONE J; NAKIJIQUINONE K; NAKIJIQUINONE L; NAKIJIQUINONE M; NAKIJIQUINONE N; NAKIJIQUINONE O; NAKIJIQUINONE P; NAKIJIQUINONE R; POLYFIBROSPONGOL; QUINONE DERIVATIVE; SESQUITERPENE; SMENOSPONDIOL; SMENOSPONGINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G1 PHASE; CONCENTRATION RESPONSE; CYTOSTASIS; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; FLOW CYTOMETRY; HUMAN; IC 50; IN VITRO STUDY; NONHUMAN; REVIEW; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

DICTYOCERATIDA;

EID: 78650651122     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md8122849     Document Type: Review

References (115)

1. Skropeta, D. Deep-sea natural products. Nat. Prod. Rep. 2008, 25, 1131-1166.
2. Thornburg, C.; Zabriskie, T.M.; McPhail, K.L. Deep-sea hydrothermal: Potencial hot spot for natural products discovery. J. Nat. Prod. 2010, 73, 489-499.
3. Molinski, T.T.; Dalisay, D.S.; Lievens, S.L.; Saludes, J.P. Drug development from marine natural products. Nat. Rev. Drug Discov. 2009, 8, 69-85.
4. Simmons, T.L.; Andrianasolo, E.; McPhail, K.; Flatt. P.; Grewick, W.H. Marine natural products as anticancer drugs. Mol. Cancer Ther. 2005, 4, 333-342.
5. Villa, F.A.; Gerwick, L. Marine natural product drug discovery: Leads for treatment of inflammation, cancer, infections, and neurological disorders. Immunopharmacol. Immunotoxicol. 2010, 32, 228-237.
6. Shi, Q.; Huo, C.; Li, L.; Zhang, M. History retrospection on chemistry research of marine natural products. Zhongcaoyao 2009, 40, 1687-1695.
7. Fusetani, N. Biotechnological potential of marine natural products. Pure Appl. Chem. 2010, 82, 17-26.
8. Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2010, 27, 165-237.
9. Morris, J.C.; Phillips, A.J. Marine natural products: Synthetic aspects. Nat. Prod. Rep. 2010, 27, 1186-1203.
10. Hill, R.A. Marine natural products. Annu. Rep. Prog. Chem. B Org. Chem. 2009, 105, 150-166.
11. Nagle, D.G.; Zhou, Y.-D. Marine natural products as inhibitors of hypoxic signaling in tumors. Phytochem. Rev. 2009, 8, 415-429.
12. Arai, M.; Kobayashi, M. Chemical biology of marine natural products. Kagaku to Seibutsu 2009, 47, 275-282.
13. Glaser, K.B.; Mayer, A.M.S. A renaissance in marine pharmacology: From preclinical curiosity to clinical reality. Biochem. Pharmacol. 2009, 78, 440-448.
14. Raviña, E. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs; Wiley-WCH: Weinheim, Germany, 2010.
15. Bailly, C. Ready for comeback of natural products in oncololoy. Biochem. Pharmacol. 2009, 77, 1447-1457.
16. Cragg, G.M.; Grothaus, P.G.; Newman, D.J. Impact of natural products on developing new anti-cancer agents. Chem Rev. 2009, 109, 3012-3043.
17. Gordaliza, M. Natural products as leads to anticancer drugs. Clin. Transl. Oncol. 2007, 9, 767-776.
18. Gordaliza, M. Terpeny-purines from the sea. Mar. Drugs 2009, 7, 833-847.
19. Lee, K.-H. Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. J. Nat. Prod. 2010, 73, 500-516.
20. Miljanich, G.P. Ziconotide: Neural calcium channel blocker for treating severe chronic pain. Curr. Med. Chem. 2004, 11, 3029-3040.
21. ® (trabectedin, ET-743). A semisynthetic process solves the supply problem. Nat. Prod. Rep. 2009, 26, 322-333.
22. Alday, P.H.; Correia, J.J. Macromolecular interaction of halichondrin B analogues eribulin (E7389) and E-076349 with tubulin by analitical ultacentrifugation. Biochemistry 2009, 48, 7927-7938.
23. Smith, J.A.; Wilson, L.; Azarenko, O.; Zhu, X.; Lewis, B.M.; Littlefield, B.A.; Jordan, M.A. Eribulin binds at microtubule ends to a single site on tubulin to suppress dynamic instability. Biochemistry 2010, 49, 1331-1337.
24. Sladic, D.; Gasic, M.J. Reactivity and biological activity of marine sesquiterpene hydroquinones avarol and related compound from sponges of Order Dictyoceratida. Molecules 2006, 11, 1-33.
25. Motti, C.A.; Bourguet-Kondracki, M.-L.; Longeon, A.; Doyle, J.R.; Llewellyn, L.E.; Tapiolas, D.M.; Yin, P. Comparison of biological properties of several marine sponge-derived sesquiterpenoid quinines. Molecules 2007, 12, 1376-1388.
26. Cragg, G.M.; Newman, D.J. Industrial applications natural products for medicinal purposes. Drugs from nature: Present development and future prospects. In Natural Products in the New Millenium: Prospects and Industrial Applications; Rauter, A.P., Palma, F.B., Justino, J., Araújo, M.E., Dos Santos, S.P., Eds.; Kluwer: Dordrecht, The Netherlands, 2002; pp. 441-461.
27. Gordaliza, M.; Miguel del Corral, J.M.; Mahiques, M.M.; San Feliciano, A.; García-Grávalos, M.D. Terpenequinone with antitumor activity. PCT Int. Appl. EP 0731078 A1, 1994.
28. Miguel del Corral, J.M.; Castro, M.A.; Gordaliza, M.; Martín, M.L.; Gamito, A.M.; Cuevas, C.; San Feliciano, A. Synthesis and citotoxicity of new heterocyclic terpenylnaphthoquinones. Bioorg. Med. Chem. 2006, 14, 2816-2827.
29. Alegría, A.; Sánchez, S.; Sánchez-Cruz, P.; Nieves, I.; Cruz, N.G.; Gordaliza, M.; Martín-Martín, M.L. Terpenylnaphthoquinones are reductively activated by NADH/NADH dehydrogenase. Toxicol. Environ. Chem. 2005, 87, 237-245.
30. Alegría, A.; Cordones, E.; Marcano, Y.; Sanchez, S.; Gordaliza, M.; Martín-Martín, M.L. Reductive activation of terpenylnaphtoquinones. Toxicology 2002, 175, 167-175.
31. Bozic, T.; Novakovic, I.; Gasic, M.J.; Juranic, Z.; Stanojkovic, T.; Tufegdzic, S.; Kljajic, Z.; Sladic, D. Synthesis and biological activity of derivatives of the marine quinone avarone. Eur. J. Med. Chem. 2010, 45, 923-929.
32. 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.
33. Parks, J.; Gyeltshen, T.; Prachyawarakorn, V.; Mahidol, C.; Ruchirawat, S.; Kittakoop, P. Glutarimide alkaloids and a terpenoid benzoquinone from Cordia globifera. J. Nat. Prod. 2010, 73, 992-994.
34. Kobayashi, J. Chemistry and biology of Okinawan marine natural products. Pure Appl. Chem. 2009, 81, 1009-1018.
35. 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.
36. 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.
37. Takahashi, Y.; Kubota, T.; Kobayashi, J. Nakijiquinones E and F, new dimeric sesquiterpenoid quinones from marine sponge. Bioorg. Med. Chem. 2009, 17, 2185-2188.
38. 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.
39. Takahashi, Y.; Ushio, M.; Kubota, T.; Yamamoto, S.; Fromont, J.; Kobayashi, J. Nakijiquinones J-R, Sesquiterpenoid quinones with an qmine residue from Okinawan marine sponges. J. Nat. Prod. 2010, 73, 467-471.
40. 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.
41. Shen, Y.-C.; Hsieh, P.-W. New sesquiterpene hydroquinones from a Taiwanese marine sponge Polyfibrospongia australis. J. Nat. Prod. 1997, 60, 93-97.
42. Qiu, Y.; Wang, X.M. A new sesquiterpenoid hydroquinone from the marine sponge Dysidea arenaria. Molecules 2008, 13, 1275-1281.
43. Haruo, Y.; Hasegawa, T.; Tanaka, H.; Takahashi, T. Total Synthesis of (±)-smenospondiol by titanium(III)-mediated tandem radical cyclization. Synlett 2001, 2001, 1935-1937.
44. Kondracki, M.-L.; Davoust, D.; Guyot, M. Smenospondiol, a biologically active hydroquinone from the sponge Smenospongia sp. J. Chem. Res. (Synop.) 1989, 3, 74-75.
45. Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y. Dictyioceratin-A and B, novel antimicrobial terpenoids from Okinawan marine sponge Hippospongia sp. Tetrahedron 1986, 42, 4197-4201. (Pubitemid 16002817)
46. Rodriguez, J.; Quiñoá, E.; 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.
47. 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.
48. Kondracki, M.L.; Guyot, M. Biologically active quinine and hydroquinones sesquiterpenoids from the sponge Smenospongia sp. Tetrahedron 1989, 45, 1995-2004.
49. Evans, T.P.; Cornell, L.; Peterson, R.W.; Faulkner, D.J. Isolation and synthesis of a glycine derivative of ilimaquinone from Fasciospongia sp. Nat. Prod. Lett. 1994, 4, 287.
50. Kondracki, M.L.; Guyot, M. Smenospongine: A cytotoxic and antimicrobial aminoquinone isolated from Smenospongia sp. Tetrahedron Lett. 1987, 28, 5815-5818.
51. Kong, D.; Aoki, S.; Sowa, Y.; Sakai, T.; Kobayashi, M. Smenospongine, a sesquiterpene aminoquinone from a marine sponge, induces G1 arrest or apoptosis in different leukemia cells. Mar. Drugs 2008, 6, 480-488.
52. Aoki, S.; Kong, D.; Matsui, K.; Rachmat, R.; Kobayashi, M. Sesquiterpene aminoquinoes from a marine sponge induce erytnroid differentiation in human chronic myelogenous leukemia K562 cells. Chem. Pharm. Bull. 2004, 52, 935-937.
53. Utkina, N.K.; Denisenko, V.A.; Scholokova, O.V.; Virovaya, M.V.; Prokof'eva, N.G. Cyclosmenospongine, a new sequiterpenoid aminoquinone from an Australian marine sponge Spongia sp. Tetrahedron Lett. 2003, 44, 101-102.
54. Ling, T.; Poupon, E.; Rueden, E.J.; Kim, S.H.; Theodorakis, E.A. Unified synthesis of quinone sesquiterpenes based on a radical decarboxilation and quinone addition reaction. J. Am. Chem. Soc. 2002, 124, 12261-12267.
55. Cimino, G.; De Rosa, S.; De Stefano, S.; Cariello, L.; Zanetti, L. Structure of two biologically active sesquiterpenoid amino-quinones from de marine sponge Dysidea avara. Experientia 1982, 38, 896.
56. Cozzolino, R.; De Giulio, A.; De Rosa, S.; Strazzullo, G.; Gašic, M.J.; Sladic, D.; Zlatovic, M. Biological activities of avarol derivatives, 1. Amino derivatives. J. Nat. Prod. 1990, 53, 699-702.
57. Müller, W.E.G.; Maidhof, A.; Zahn, R.K.; Schröder, H.C.M.; Gasic, M.J.; Heidemann, D.; Bernd, A.; Kurelec, B.; Eich, E.; Seibert, G. Potent antileukemic activity of the novel cytostatic agent avarone and its analogues in vitro and in vivo. Cancer Res. 1985, 45, 4822-4826.
58. Müller, W.E.G.; Sobel, C.; Sachsse, W.; Diehl-Seifert, B.; Zahn, R.K.; Eich, E.; Kljajic, 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.
59. 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.
60. 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.
61. De Giulio, A.; De Rosa, S.; Strazzullo, G.; Diliberto, L.; Obino, P.; Marongiu, M.E.; Pani, A.; La Colle, P. Synthesis and evaluation of cytostatic and antiviral activities of 3'- and 4'-avarone derivatives. Antivir. Chem. Chemother. 1991, 4, 223-227.
62. 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.
63. 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.
64. 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.
65. 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.
66. De Giulio, A.; De Rosa, S.; Di Vincenzo, G.; Strazzullo, G. Further bioactive derivative of avarol from Dysidea avara. Tetrahedron 1990, 46, 7971-7976.
67. Sakurai, J.; Oguchi, T.; Watanabe, K.; Abe, H.; Kanno, S.-I.; Ishikawa, M.; Katoh, T. Highly efficient total synthesis of the marine natural products. (+)-avarone, (+)-avarol, (-)-neoavarone, (-)-neoavarol and (+)-aureol. Chem. Eur. J. 2008, 14, 829-837.
68. Shen, Y.-C.; Lu, C.-H.; Chakraborty, R.; Kuo, Y.-H. Isolation of sesquiterpenoids from sponge Dysidea avara and chemical modification of avarol as potencial antitumor agents. Nat. Prod. Rep. 2003, 17, 83-89.
69. Amigo, M.; Terencio, M.C.; Paya, M.; Iodice, C.; De Rosa, S. Synthesis and evaluation of diverse thio avarol derivatives as potential UVB photoprotectives candidates. Bioorg. Med. Chem. Lett. 2007, 17, 2561-2565.
70. Amigo, M.; Terencio, M.C.; Mitova, M.; Iodice, C.; Paya, M.; De Rosa, S. Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE2 generation and proliferation in HaCaT cell line. J. Nat. Prod. 2004, 67, 1459-1463.
71. 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.
72. Schmitz, F.J.; Lakshmi, V.; Powell, D.R.; Van der Helm, D. Arenarol and arenarona: Sesquiterpenoids with rearranged drimane skeletons from marine sponge Dysidea arenaria. J. Org. Chem. 1984, 49, 241-244.
73. Utkina, N.K.; Denisenko, V.A.; Krasokhin, V.B. Sesquiterpenoidd aminoquinones from marine sponge Dysidea sp. J. Nat. Prod. 2010, 73, 788-791.
74. 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. Widendiol A and B, cholesteryl esther transfer protein inhibitors from marine sponge Xetospongia widenmayeri. Bioorg. Med. Chem. Lett. 1995, 5, 605-610.
75. Chackalamannil, S.; Wang, Y.; Xia, Y.; Czarniecki, M. An efficient synthesis of wiedendiol A from (+)-sclareolide. Tetrahedron Lett. 1995, 36, 5315-5318.
76. Laube, T.; Bernet, A.; Dahse, H.-M.; Jacobsen, I.D.; Seifert, K. Synthesis and pharmacological activities of some sesquiterpene quinines and hydroquinones. Bioorg. Med. Chem. 2009, 17, 1422-1427.
77. 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.
78. Grube, A.; Assman, M.; Lichte, E.; Sasse, F.; Pawlik, J.R.; Loeck, M. Bioactive metabolites from the Caribbean sponge Aka coralliphagun. J. Nat. Prod. 2007, 70, 504-509.
79. Cimino, G.; De Stefano, S.; Minale, L. Chromazonarol, a chroman-sesquiterpenoid from sponge Dysidea pallenscens. Experientia 1975, 31, 1117.
80. 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.
81. Djura, P.; Stierle, D.B.; Sullivan, B.; Faulkner, D.J. Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (Polyfibrospongia) echina. J. Org. Chem. 1980, 45, 1435-1441.
82. 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.
83. 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.
84. 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.
85. 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.
86. Kohmoto, S.; McConnell, O.J.; Wright, A.; Koehn, F.; Thompson, W.; Lui, M.; Snader, K.M. Puupehenone, a cytotoxic metabolite from a deep water marine sponge, Stronglyophora hartmani. J. Nat. Prod. 1987, 50, 336.
87. Nasu, S.S.; Yeung, B.K.S.; Hamann, T.; Scheuer, P.J.; Kelly-Borges, M.; Goins, K. Puupehenone-related metabolites from two Hawaiian sponges, Hyrtios sp. J. Org. Chem. 1995, 60, 7290-7292.
88. Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Saez, B. Total synthesis of both enantiomers of 15-oxopuupehenol methylendioxy derivatives. Tetrahedron Lett. 1997, 38, 7249-7252.
89. Barrero, A.J.; Alvarez-Manzaneda, E.J.; Chahboun, R.; Cortes, M.; Armstrong, V. Synthesis and antitumoral activities of puupehedione and related compounds. Tetrahedron 1999, 55, 15181-15208.
90. Alvarez-Manzaneda, E.; Chhboun, R.; Cabrera, E.; Alvarez, E.; Haidour, A.; Ramos, J.M.; Alvarez-Manzaneda, R.; Tapia, R.; Es-Samti, H.; Fernandez, A.; Barranco, I. A convenient enantiospecific route towards bioactive merosesquiterpenes by cationic-resin-promoted Friedel-Crafts alkylation with α,β-enones. Eur. J. Org. Chem. 2009, 2009, 1139-1143.
91. Castro, M.E.; Gonzales-Iriarte, M.; Barrero, A.F.; Salvador-Tormo, N.; Muñoz-Chapuli, R.; Medina, M.A.; Quesada, A.R. Study of puupehenone and related compounds as inhibitors of angiogenesis. Int. J. Cancer 2004, 110, 31-38.
92. Pina, I.; Sanders, M.L.; Crews, P. Puupehenones congeners from an Indo-pacific Hyrtios sponge. J. Nat. Prod. 2003, 66, 2-6.
93. 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.
94. Swersey, J.C.; Barrows, L.R.; Ireland, C.M. Mamanuthaquinone: An antimicrobial and cytotoxic metabolite of Fasciospongia sp. Tetrahedron Lett. 1991, 32, 6687-6690.
95. 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.
96. Bourghet-Kondracki, M.-L.; Martin, M.-T.; Guyot, M. Smenoqualone a novel sesquiterpenoid from the marine sponge Smenospongia sp. Tetrahedron Lett. 1992, 33, 8079-8080.
97. 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.
98. 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, 8042-8044.
99. Li, Y.; Zhang, Y.; Shen, X.; Guo, Y.-W. A novel sesquiterpene quinine from Haian sponge Dysidea villosa. Bioorg. Med. Chem. Lett. 2009, 19, 390-392.
100. Giannini, C.; Debitus, C.; Lucas, R.; Ubeda, A.; Paya, M.; Hooper, J.N.; D'Auria, M.V. New sesquiterpene derivatives from sponge Dysidea species with a selective inhibitor profile against hyman phosfopholipase A2 and other leukocyte functions. J. Nat. Prod. 2001, 64, 612-615.
101. Alvi, K.A.; Rodríguez, J.; Diaz, M.C.; Moretti, R.; Lee, R.H.; Slate, D.L.; Crews, P. Protein tyrosine kinase inhibitory properties of planar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis. J. Org. Chem. 1993, 58, 4871-4880.
102. Casapullo, A.; Minale, L.; Zollo, F. Paniceins and related sesquiterpenoids from the Mediterranean sponge Reniera fulva. J. Nat. Prod. 1993, 56, 527-533.
103. Zubia, E.; Ortega, M.J.; Carballo, J.L.; Salva, J. Sesquiterpene hydroquinone from the sponge Reniera mucosa. Tetrahedron 1994, 50, 8153-8160.
104. 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.
105. 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.
106. Munday, R.H.; Denton, R.M.; Anderson, J.C. Asymmetric synthesis of 6'-hydroxyarenarol: The proposed biosynthetic precursor to popolohuanone E. J. Org. Chem. 2008, 73, 8033-8038.
107. 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.
108. Prokof'eva, N.G.; Utkina, N.K.; Chaikina, E.L.; Makarchenko, A.E. Biological activities of marine sesquiterpenoid quinones: Structure-activity relationships in cytotoxic and hemolytic assays. Comp. Biochem. Physiol. B: Biochem. Mol. Biol. 2004, 139, 169-173.
109. Schirmer, R.H.; Müller, J.G.; Krauth-Siegel, R.L. Disulfide-Reductase Inhibitors as Chemotherapeutic Agents: The Design of Drugs for Trypanosomiasis and Malaria. Angew. Chem. Int. Ed. Engl. 1995, 34, 141-154.
110. 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.
111. O'Brien, P.J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 1991, 80, 1-41.
112. Schröder, H.C.; Wenger, R.; Gerner, H.; Reuter, P.; Kuchino, Y.; Müller, 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.
113. Sladic, D.; Gašic, M.J. Effects of iron(II) compounds on the amount of DNA damage in Friend erythroleukemia cells induced by avarol. Role of hydroxyl radicals. J. Serb. Chem. Soc. 1994, 59, 915-920.
114. Novakovic, I.; Vujcic, Z.; Božic, T.; Božic, N.; Milosavic, N.; Sladic, D. Chemical modification of β-lactoglobulin by quinones. J. Serb. Chem. Soc. 2003, 68, 243-248.
115. Sladic, D.; Novakovic, I.; Vujcic, Z.; Božic, T.; Božic, N.; Milic, D.; Šolaja, B.; Gašic, M.J.; Protein covalent modification by biologically active quinones. J. Serb. Chem. Soc. 2004, 69, 901-907.