Quinone/hydroquinone sesquiterpenes

Mini-Reviews in Organic Chemistry

Volumn 7, Issue 3, 2010, Pages 230-254

  Marcos, I S ^a   Conde, A ^a   Moro, R F ^a   Basabe, P ^a   Diez, D ^a   Urones, J G ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Drimane; Rearranged drimane; Sesquiterpenes quinone hydroquinone

Indexed keywords

METABOLITES; OLEFINS;

DRIMANE; ISOLATED STRUCTURES; REARRANGED DRIMANE; SECONDARY METABOLITES; SESQUITERPENE QUINONE/HYDROQUINONE; SESQUITERPENES; SYNTHESISED;

BIOACTIVITY;

EID: 77957201024     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019310791384128     Document Type: Article

References (182)

1. Capon, R. J. Studies in Natural Products Chemistry, Structure and Chemistry (Part C); Atta-Ur Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 15, pp. 289-326.
2. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 2008, 25, 1180.
3. Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2009, 26, 170.
4. Fujimoto, H.; Nakamura, E.; Kim, Y. P.; Okuyama, E.; Ishibashi, M.; Sassa, T. Immunomodulatory constituents from an ascomycete, Eupenicillium crus- taceum, and revised absolute structure of macrophorin D. J. Nat. Prod. 2001, 64, 1234.
5. Zhi-Hui, D.; Ze-Jun, D.; Ji-Kai, L. Albaconol, A novel prenylated resorcinol (=Benzene-1,3-diol) from basidiomycetes Albatrellus confluens. Helv. Chim. Acta 2001, 84, 259.
6. Kono, K.; Tanaka, T.; Ogita, T.; Hosoya, T.; Kohama, T. F-12509A, a new sphingosine kinase inhibitor, produced by a discomycete. J. Antibiot. 2000, 53, 459.
7. Minale, L.; Sodano, R.; Sodano, G. Avarol a novel sesquiterpenoid hydroquinone with a rearranged drimane skeleton from the sponge Dysidea avara. Tetrahedron Lett. 1974, 15, 3401.
8. Djura, P.; Stierle, D. B.; Sullivan, B.; Faulkner, D. J. Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (.ident.Polyfibrospongia) echina. J. Org. Chem. 1980, 45, 1435.
9. Laube, T.; Beil, W.; Seifert, K. Total synthesis of two 12-nordrimanes and the pharmacological active sesquiterpene hydroquinone yahazunol. Tetrahe- dron 2005, 61, 1141.
10. Laube, T.; Schröder, J.; Stehle, R.; Seifert, K. Total synthesis of yahazunol, zonarone and isozonarone. Tetrahedron 2002, 58, 4299. pharmacological activities of some sesquiterpene quinones and hydroquinones. Bioorg. Med. Chem. 2009, 17, 1422.
11. Kurata, K.; Taniguchi, K.; Suzuki, M. Cyclozonarone, a sesquiterpene- substituted benzoquinone derivative from the brown alga Dictyopteris undulada. Phytochemistry 1996, 41, 749.
12. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 2003, 20, 392.
13. Talpir, R.; Rudi, A.; Kashman, Y. Three new sesquiterpene hydroquinones from marine origin. Tetrahedron 1994, 50, 4179.
14. Yong, K. W. L.; Jankam, A.; Hooper, J. N. A.; Suksamrarn, A.; Garson, M. A. Stereochemical evaluation of sesquiterpene quinones from two sponges of the genus Dactylospongia and the implication for enantioselective processes in marine terpene biosíntesis. Tetrahedron 2008, 64, 6341.
15. Alvarez-Manzaneda, E.; Chahboun, R.; Cabrera, E.; Alvarez, E.; Haidour, E.; Ramos, J. M.; Alvarez-Manzaneda, R.; Tapia, R.; Es-Samti, H.; Fernández, A.; Barranco, I. A convenient enantiospecific route towards bioactive merosesquiterpenes by cationic-resin-promoted friedel-crafts alkylation with, enones. Eur. J. Org. Chem. 2009, 1139.
16. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 1996, 13, 307.
17. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 1995, 12, 223.
18. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2001, 18, 1.
19. Bernet, A.; Schröder, J.; Seifert, K. Total synthesis of the marine sesquiter- pene quinones hyatellaquinone and spongiaquinone. Helv. Chim. Acta 2003, 86, 2009.
20. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 2001, 18, 650.
21. Maezawa, N.; Furuichi, N.; Tsuchikawa, H.; Katsumura, S. Synthesis of a novel sphingosine kinase inhibitor ()-F-12509A and determination of its ab- solute configuration. Tetrahedron Lett. 2007, 48, 4865.
22. Wijeratne, E. M. K.; Paranagama, P. A.; Marron, M. T.; Gunatilaka, M. K.; Arnold, A. E.; Gunatilaka, A. A. L. Sesquiterpene quinones and related me- tabolites from Phyllosticta spinarum, a fungal strain endophytic in Platy- cladus orientalis of the sonoran desert. J. Nat. Prod. 2008, 71, 218.
23. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 2002, 19, 650.
24. McNamara, C. E.; Larse, 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.
25. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 2006, 23, 943.
26. Blunt, J. W.; Copp, B. R.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2007, 24, 31.
27. 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.
28. Jankam, A.; Somerville, M. J.; Hooper, J. N. A.; Brecknell, D. J.; Suksam- rarn, A.; Garson, M. A. Dactylospongiaquinone, a new meroterpenoid from the Australian marine sponge Dactylospongia n. sp. Tetrahedron 2007, 63, 1577.
29. Mitome, H.; Nagasawa, T.; Miyaoka, H.; Yamada, Y.; Soest, W. M. Dacty- loquinones C, D and E novel sesquiterpenoid quinones, from the Okinawan marine sponge, Dactylospongia elegans. Tetrahedron 2002, 58, 1693.
30. Piña, I. C.; Sanders, M. L.; Crews, P. Puupehenone Congeners from an Indo- Pacific Hyrtios Sponge. J. Nat. Prod. 2003, 66, 2.
31. Blunt, J. W.; Copp, B. R.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2005, 22, 15.
32. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 1998, 15, 73.
33. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 1998, 15, 113.
34. Urban, S.; Capon, R. J. Deoxyspongiaquinones: new sesquiterpene quinones and hydroquinones from a southern australian marine sponge Euryspongia sp. Aust. J. Chem. 1996, 49, 611.
35. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 1999, 16, 155.
36. Blunt, J. W.; Copp, B. R.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2006, 23, 26.
37. Quideau, S.; Lebon, M.; Lamidey, A. M. Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxi- dative activation route. Org. Lett. 2002, 4, 3975.
38. El Sayed, K. A.; Bartyzel, P.; Shen, X. D.; Perry, T. L.; Zjawiony, J. K.; Hamann, M. T. Marine natural products as antituberculosis agents. Tetrahe- dron 2000, 56, 949.
39. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Enantiospecific synthesis of (+)-Puupehenone from (-)-Sclareol and protocatechualdehyde. Tetrahedron Lett. 1997, 38, 2325.
40. Nasu, E. S.; Yeung, B. K. S.; Hamann, M. T.; Scheuer, P. J. Puupehenone- related metabolites from two Hawaiian sponges, Hyrtios sp. J. Org. Chem. 1995, 60, 7290.
41. Urban, S.; Capon, R. J. Absolute stereochemistry of puupehenone and related metabolites. J. Nat. Prod. 1996, 59, 900.
42. Ciavatta, M. L.; Lopez Gresa, M. P.; 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.
43. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Synthesis and antitumor activity of puupehedione and related compounds. Tetrahedron 1999, 55, 15181.
44. Chan, J. A.; Freyer, A. J.; Carte, B. K.; Hemling, M. E.; Hofmann, G. A.; Mattern, M. R.; Mentzer, M. A.; Westley, J. W. Protein kinase c inhibitors: Novel spirosesquiterpene aldehydes from a marine sponge Aka (=Siphonodictyon) coralliphagum. J. Nat. Prod. 1994, 57, 1543.
45. Grube, A.; Assman, M.; Lichte, E.; Sasse, F.; Pawlik, J. R.; Köck, M. Bioactive Metabolites from the caribbean sponge Aka coralliphagum. J. Nat. Prod. 2007, 70, 504.
46. Fenical, W.; Sims, J. J.; Squatrito, D.; Wing, R. M.; Radlick, P. Marine natural products. VII. Zonarol and isozonarol, fungitoxic hydroquinones from the brown seaweed Dictyopteris zonarioides. J. Org. Chem. 1973, 38, 2383.
47. Barrero, A. F.; 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.
48. Ciminio, G.; De Stefano, S.; Minale, L. Chromazonarol, a chroman- sesquiterpenoid from the sponge Disidea pallescens. Experientia 1975, 31, 1117.
49. Perez-García, E.; Zubía, E.; Ortega, M. J.; Carballo, J. L. Merosesquiterpenes from Two Sponges of the Genus Dysidea. J. Nat. Prod. 2005, 68, 653.
50. Faulkner, D. J. Marine natural products: metabolites of marine algae and herbivorous marine molluscs. Nat. Prod. Rep. 1984, 1, 251.
51. Ochi, M.; Kotsuki, H.; Muraoka, K.; Tokoroyama, T. The Structure of Yaha- zunol, a New Sesquiterpene-substituted Hydroquinone from the Brown Sea- weed Dictyopteris undulata Okamura. Bull. Chem. Soc. Jpn. 1979, 52, 629.
52. Sullivan, B.; Djura, P.; McIntyre, E.; Faulkner, J. Antimicrobial constituents of the sponge Siphonodictyon coralliphagum. Tetrahedron 1981, 37, 979.
53. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 1988, 5, 613.
54. Sullivan, B. W.; Faulkner, D. J.; Matsumoto, G. K.; Cun-Heng, H.; Clardy, J. Metabolites of the burrowing sponge Siphonodictyon coralliphagum. J. Org. Chem. 1986, 51, 4568.
55. Mukku, V. J. R. V.; Edrada, R. A.; Schmitz, F. J.; Shanks, M. K.; Chaudhuri, B.; Fabbro, D. New Sesquiterpene Quinols from a Micronesian Sponge, Aka sp. J. Nat. Prod. 2003, 66, 686.
56. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 1994, 11, 533.
57. Rodríguez, 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.
58. Fraga, B. M. Natural sesquiterpenoids Nat. Prod. Rep. 2005, 22, 465.
59. Song, F. H.; Fan, X.; Xu, X. L.; Zhao, J. L.; Han, L. J.; Shi, J. G. A new sesquiterpene-substituted benzoic acid from the brown alga Dictyopteris di- varicata. Chin. Chem. Lett. 2004, 15, 316.
60. Fraga, B. M. Natural sesquiterpenoids. Nat. Prod. Rep. 1997, 14, 145.
61. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2000, 17, 7.
62. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 1997, 14, 259.
63. Coval, S. J.; Conover, M. A.; Mierzwa, R.; King, A.; Puar, M. S.; Phife, D. W.; Pai, J. K.; Burrier, B. E.; Ahn, H. S.; Boykow, G. C.; Patel, M.; Pomponi, S. A. Wiedendiol-A and -B, cholesteryl ester transfer protein inhibitors from the marine sponge Xestospongia wiedenmayeri. Bioorg. Med. Chem. Lett. 1995, 5, 605.
64. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes. Tetrahedron 1998, 54, 5635.
65. Chackalamannil, S.; Wang, Y.; Xia, Y.; Czarniecki, M. An efficient synthe- sis of Wiedendiol-A from (+)-sclareolide. Tetrahedron Lett. 1995, 36, 5315.
66. Arima, Y.; Kinoshita, M.; Akita, H. Natural product synthesis from (8aR)- and (8aS)-bicyclofarnesols: synthesis of (+)-wiedendiol A, (+)- norsesterterpene diene ester and ()-subersic acid. Tetrahedron Asymmetry 2007, 18, 1701.
67. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Enantiospecific Synthesis of Wiedendiol-B from ()-Sclareol and (+)-cis-Abienol. Tetrahe- dron Lett. 1997, 38, 8101.
68. Alvarez-Manzaneda, E. J.; Chahboun, R.; Pérez, I. B.; Cabrera, E.; Alvarez, E., Alvarez-Manzaneda, R. First Enantiospecific Synthesis of the Antitumor Marine Sponge Metabolite ()-15-Oxopuupehenol from ()-Sclareol. Org. Lett. 2005, 7, 1477.
69. Killday, K. B.; Wright, A. E.; Jackson, R. H.; Sills, M. A. 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.
70. Spyroudis, S. Hydroxyquinones: synthesis and reactivity. Molecules 2000, 5, 1291.
71. Urban, S.; Capon, R. J. Marine sesquiterpene quinones and hydroquinones: acid-catalyzed rearrangements and stereochemical investigations. Aust. J. Chem. 1994, 47, 1023.
72. Swersey, J. C.; Barrows, L. R.; Ireland, C. M. Mamanuthaquinone: an antim- icrobial and cytotoxic metabolite of Fasciospongia sp. Tetrahedron Lett. 1991, 32, 6687.
73. Stahl, P.; Kissau, M.; 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.
74. Carté, B.; Rose, C.; B.; Faulkner, D. J.. 5-Epi-Ilimaquinone, a metabolite of the sponge Fenestraspongia sp. J. Org. Chem. 1985, 50, 2785.
75. 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.
76. Utkina, N. K.; Denisenko, V. A.; Scholokova, O. V.; Virovaya, M.; Prokof'eva, N. G. Cyclosmenospongine, a new sesquiterpenoid aminoqui-none from an Australian marine sponge Spongia sp. Tetrahedron Lett. 2003, 44, 101.
77. Bourguet-Kondracki, M. L., Martin, M. T.; Guyot, M. Smenoqualone a novel sesquiterpenoid from the marine sponge Smenospongia sp. Tetrahedron Lett. 1992, 33, 8079.
78. Nakamura, M.; Suzuki, A.; Nakatani, M.; Fuchikami, T.; Inoue, M.; Katoh, T. An efficient synthesis of (+)-aureol via boron trifluoride etherate- promoted rearrangement of (+)-arenarol. Tetrahedron Lett. 2002, 43, 6929.
79. Lakshmi, V.; Gunasekera, S. P.; Schmitz, F. J.; Ji, X.; Helm, D. Acid- catalyzed rearrangement of arenerol. J. Org. Chem. 1990, 55, 4709.
80. Suzuki, A.; Nakatani, M.; Nakamura, M.; Kawaguchi, K.; Inoue, M.; Katoh, T. Highly improved synthesis of (+)-Aureol via (-)-Neoavarone and (-)-Neo- avarol, by employing salcomine oxidation and acid-induced rearrange- ment/cyclization strategy. Synlett 2003, 3, 329.
81. Nakatani, M.; Nakamura, M.; Suzuki, A.; Kawaguchi, K.; Fuchikami, T.; Inoue, M.; Katoh, T. Enantioselective total synthesis of (+)-aureol via a BF3·Et2O-promoted rearrangement/cyclization reaction of (+)-arenarol. ARKIVOC 2003, 45.
82. Sakurai, J.; Oguchi, T.; Watanabe, K.; Abe, H.; Kanno, S.; 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.
83. Kochanowska, A. J.; Rao, K. V.; Childress, S.; El-Alfy, A.; Matsumoto, R. R.; Kelly, M.; Stewart, G. S.; Suftka, K. J.; Hamann, M. T. Secondary me- tabolites from three florida sponges with antidepressant activity. J. Nat. Prod. 2008, 71, 186.
84. Hu, J. F.; Schetz, J. A.; Kelly, M.; Peng, J. N.; Ang, K. K. H.; Flotow, H.; Leong, C. Y.; Ng, S. B.; Buss, A. D.; Wilkins, S. P.; Hamann, M. T. New an- tiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the jamaican sponge Smenospongia aurea. J. Nat. Prod. 2002, 65, 476.
85. Longley, R. E.; McConell, O. J.; Essich, E.; Harmody, D. Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity. J. Nat. Prod. 1993, 56, 915.
86. Tymiak, A. A.; Rinehart, K. L.; Bakus, G. J. Constituents of morphologically similar sponges: Aplysina and smenospongia species. Tetrahedron 1985, 41, 1039.
87. Wright, A. E.; Rueth, S. A.; Cross, S. S. An antiviral sesquiterpene hydro- quinone from the marine sponge Strongylophora hartmani. J. Nat. Prod. 1991, 54, 1108.
88. Li, Y.; Zhang, Y.; Shen, X.; Guo, Y. A novel sesquiterpene quinone from Hainan sponge Dysidea villosa. Bioorg. Med. Chem. Lett. 2009, 19, 390.
89. De Giulio, A.; De Rosa, S.; Di Venzo, G.; Strazzullo, G. Further bioactive derivative of avarol from Dysidea avara. Tetrahedron 1990, 46, 7971.
90. Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction. J. Am. Chem. Soc. 2002, 124, 12261.
91. Ling, T.; Xiang, A. X.; Theodorakis, E. A. Enantioselective total synthesis of avarol and avarone. Angew. Chem. Int. Ed. 1999, 38, 3089.
92. Radeke, H. S.; Digits, C. A.; Bruner, S. D.; Snapper, M. L. New tools for studying vesicular-mediated protein trafficking: synthesis and evaluation of ilimaquinone analogs in a non-radioisotope-based antisecretory assay. J. Org. Chem. 1997, 62, 2823.
93. An, J.; Wiemer, D. F. Stereoselective synthesis of (+)-Avarol, (+)-Avarone, and some nonracemic analogues. J. Org. Chem. 1996, 61, 8775.
94. Crispino, A.; De Giulio, A.; De Rosa, S.; Strazullo, G. A new bioactive derivative of avarol from the marine sponge Dysidea avara. J. Nat. Prod. 1989, 52, 646.
95. De Rosa, S.; DeGiulio, 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.
96. Sarma, A. S.; Chattopadhyay, P. Synthetic studies of trans-clerodane diterpe- noids and congeners: stereocontrolled total synthesis of (+)-avarol. J. Org. Chem. 1982, 47, 1727.
97. Locke, E. P.; Hecht, S. M. Enantiospecific total synthesis of (+)- and (-)- avarone and -avarol. Chem. Commun. 1996, 2717.
98. Hirsch, S.; Rudi, A.; Kashman, Y. New avarone and avarol derivatives from the marine sponge Dysidea cinerea. J. Nat. Prod. 1991, 54, 92.
99. Stewart, M.; Fell, P. M.; Blunt, J. W.; Munro, M. H. G. Avarol and related compounds from the new zealand marine sponge Dysidea sp. Aust. J. Chem. 1997, 50, 341.
100. Salmoun, M.; Devijver, C.; daloze, D.; Braekman, J. C.; Gomez, R.; Klui- jver, M.; Soest, R. W. M. New sesquiterpene/quinones from two sponges of the genus Hyrtios. J. Nat. Prod. 2000, 63, 452.
101. Capon, R. J. The Acid-catalyzed rearrangement and absolute stereochemistry of isospongiaquinone. J. Nat. Prod. 1990, 53, 753.
102. Stahl, P.; Waldmann, H. Asymmetric synthesis of the nakijiquinones- selective inhibitors of the Her-2/Neu protooncogene. Angew. Chem. Int. Ed. 1999, 38, 3710.
103. Urban, S.; Capon, R. J. 5-epi-Isospongiaquinone, a new sesquiter- pene/quinone antibiotic from an australian marine sponge, Spongia hispida. J. Nat. Prod. 1992, 55, 1638.
104. Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. Total synthesis of (-)-Ilimaquinone. J. Org. Chem. 1995, 60, 1114.
105. Venkateswarlu, Y.; Faulkner, D. J. Smenochromenes, unusual macrocyclic sesquiterpene hydroquinone derivatives from a Seychelles sponge of the ge- nus Smenospongia. J. Org. Chem. 1991, 56, 6271.
106. Sladic, D.; Gasic, M. J. reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order dictyoceratida. Molecules 2006, 11, 1.
107. Schmitz, F. J.; Lakshmi, V.; Powel, D. R.; Helm, D. Arenarol and arenarone: sesquiterpenoids with rearranged drimane skeletons from the marine sponge Dysidea arenaria. J. Org. Chem. 1984, 49, 241.
108. Yoo, H.-D.; Leung, D.; Sanghara, J.; Daley, D.; van Soest, R.; Andersen, R. J. Isoarenarol, A new protein kinase inhibitor from the marine sponge Dysidea arenaria. Pharm. Biol. 2003, 41, 223.
109. Kwak, J. H.; Schmitz, F. J.; Kelly, M. Sesquiterpene quinols/quinones from the micronesian sponge Petrosaspongia metachromia. J. Nat. Prod. 2000, 63, 1153.
110. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2002, 19, 1.
111. Iguchi, K.; Sahashi, A.; Kohno, J.; Yamada, Y. New sesquiterpenoid hydro- quinone and quinones from the okinawan marine sponge (Dysidea sp.) Chem. Pharm. Bull. 1990, 38, 1121.
112. Luibrand, R. T.; Erdman, T. R.; Vollmer, J. J.; Scheuer, P. J. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge. Tetrahedron 1979, 35, 609.
113. 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.
114. Oda, T.; Wang, W.; Ukai, K.; Nakazawa, T.; Mochizuki, M. A sesquiterpene quinone, 5-Epi-smenospongine, promotes TNF- production in LPS- stimulated RAW 264.7 cells. Mar. Drugs 2007, 5, 151.
115. Shen, Y.; Hsieh, P. New sesquiterpene hydroquinones from a taiwanese marine sponge Polyfibrospongia australis. J. Nat. Prod. 1997, 60, 93.
116. Kondracki, M.; Guyot, M. Biologically active quinone and hydroquinone sesquiterpenoids from the sponge smenospongia sp. Tetrahedron 1989, 45, 1995.
117. Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 1990, 7, 269.
118. Capon, R. J.; MacLeod, J. K. Revision of the absolute stereochemistry of ilimaquinone. J. Org. Chem. 1987, 52, 5059.
119. Poigny, S.; Guyot, M.; Samadi, M. Efficient total synthesis of ()- ilimaquinone. J. Org. Chem. 1998, 63, 5890.
120. Ling, T.; Poupon, E.; Rueden, E. J.; Theodorakis, E. A. Synthesis of ()- ilimaquinone via a radical decarboxylation and quinone addition reaction. Org. Lett. 2002, 4, 819.
121. Shen, Y.; Hsieh, P. New sesquiterpene hydroquinones from a taiwanese marine sponge Polyfibrospongia australis. J. Nat. Prod. 1997, 60, 93.
122. Cao, S.; Gao, Z.; Thomas, S. J.; Hetch, S. M.; Lazo, J. S.; Kingston, D. G. I. marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase J. Nat. Prod. 2004, 67, 1716.
123. Kondracki, M.; Guyot, M. Smenospongine: A cytotoxic and antimicrobial aminoquinone isolated from Smenospongia sp. Tetrahedron Lett. 1987, 28, 5815.
124. Aoki, S.; Kong, D.; Matsui, K.; Kobayashi, M. Smenospongine, a spongean sesquiterpene aminoquinone, induces erythroid differentiation in K562 cells. Anti-Cancer Drugs 2004, 15, 363.
125. Kondracki, M.; Guyot, M. Smenospongine: A cytotoxic and antimicrobial aminoquinone isolated from Smenospongia sp. Tetrahedron Lett. 1987, 28, 5815.
126. 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.
127. Blunt, J. W.; Copp, B. R.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2003, 20, 1.
128. Blunt, J. W.; Copp, B. R.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2004, 21, 1.
129. Anderson, J. C.; Pearson, D. J. A strategy for the synthesis of popolohuanone E: formal total synthesis of (±)-arenarol. J. Chem. Soc, Perkin Trans. 1 1998, 2023.
130. Watson, A. T.; Park, K.; Wiemer, D. F. Application of the nickel-mediated neopentyl coupling in the total synthesis of the marine natural product arenarol. J. Org. Chem. 1995, 60, 5102.
131. Haruo, Y.; Hasegawa, T.; Tanaka, H.; Takahashi, T. Total synthesis of (±)- smenospondiol by Titanium(III)-Mediated tandem radical cyclization. Synlett 2001, 12, 1935.
132. Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y.; Hirata, Y. Dictyoceratin-A and -B, novel antimicrobial terpenoids from the okinawan marine sponge Hippospongia sp. Tetrahedron 1986, 42, 4197.
133. Schröder, J.; Matthes, B.; Seifert, K. Total synthesis of the marine sesquiter- pene quinone ()-cyclozonarone. Tetrahedron Lett. 2001, 42, 8151.
134. Cortés, M.; Valderrama, J. A.; Cuellar, M.; Armstrong, V.; Preite, M. Synthesis of (+)-cyclozonarone and the absolute configuration of naturally occurring ()-cyclozonarone. J. Nat. Prod. 2001, 64, 348.
135. Goclick, E.; Knig, G. M.; Wright, A. D.; Kaminsky, R. Pelorol from the tropical marine sponge Dactylospongia elegans. J. Nat. Prod. 2000, 63, 1150.
136. 2+ ATPase of skeletal muscle myosin. Bioorg. Med. Chem. 2003, 11, 3077.
137. 2+ ATPase of skeletal muscle myosin. Bioorg. Med. Chem. 2005, 13, 999.
138. Toyooka, N.; Nagaoka, M.; Sasaki, E.; Hongbo, Q.; Kakuda, H.; Nemoto, H. Model studies toward the total synthesis of halenaquinol and halenaquinone. Tetrahedron 2002, 58, 6097.
139. Roll, D. M.; Scheuer, P. J.; Matsumoto, G. K.; Clardy, J. Halenaquinone, a pentacyclic polyketide from a marine sponge. J. Am. Chem. Soc. 1983, 105, 6177.
140. Schmitz, F. J.; Bloor, S. J. Xesto- and halenaquinone derivatives from a sponge, Adocia sp., from Truk lagoon. J. Org. Chem. 1988, 53, 3922.
141. Kienzler, M. A.; Suseno, S.; Trauner, D. Vinyl Quinones as Diels Alder Dienes: concise synthesis of ()-Halenaquinone. J. Am. Chem. Soc. 2008, 130, 8604.
142. Sutherland, H. S.; Souza, F. E. S.; Rodrigo, R. G. A. A short synthesis of (±)- halenaquinone. J. Org. Chem., 2001, 66, 3639.
143. Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. Catalytic asymmetric synthesis of halenaquinone and halenaquinol. Synthesis 1998, 581.
144. Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. Catalytic Asymmet- ric Synthesis of Halenaquinone and Halenaquinol. J. Org. Chem. 1996, 61, 4876.
145. Harada, N.; Sugioka, T.; Ando, Y.; Hiyoshi, N.; Uda, H.; Kuriki, T. Total synthesis of (+)-halenaquinol and (+)-halenaquinone. Experimental proof of their absolute stereostructures theoretically determined. J. Am. Chem. Soc. 1988, 110, 8483.
146. Kobayashi, M.; Shimizu, N.; Kitagawa, I.; Kyogoku, Y.; Harada, N.; Uda, H. Absolute stereostructures of halenaquinol and halenaquinol sulfate, penta- cyclic hydroquinones from the okinawan marine sponge xestospongia sapra, as determined by theoretical calculation of CD spectra. Tetrahedron Lett. 1985, 26, 3833.
147. Harada, N.; Uda, H.; Kobayashi, M; Shimizu, N.; Kitagawa, I. Absolute stereochemistry of the halenaquinol family, marine natural products with a novel pentacyclic skeleton, as determined by the theoretical calculation of circular dichroism spectra. J. Am. Chem. Soc. 1989, 111, 5668.
148. 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, 14, 713.
149. Laurent, D.; Jullian, V.; Parenty, A.; Knibiehler, M.; Dorin, D.; Schmitt, S.; Lozach, O.; Lebouvier, N.; Frostin, M.; Alby, F.; Maurel, S.; Doerig, C.; Meijer, L.; Sauvain, M. Antimalarial potential of xestoquinone, a protein kinase inhibitor isolated from a Vanuatu marine sponge Xestospongia sp. Bioorg. Med. Chem. 2006, 14, 4477.
150. Sutherland, H. S.; Higgs, K. C.; Taylor, N. J.; Rodrigo, R. Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives. Tetrahedron 2001, 57, 309.
151. Maddaford, S. P.; Andresen, N. G.; Cristofoli, W. A.; Keay, B. A. Total synthesis of (+)-Xestoquinone using an asymmetric palladium-catalyzed polyene cyclization. J. Am. Chem. Soc. 1996, 118, 10766.
152. Harada, N.; Sugioka, T.; Soutome, T.; Hiyoshi, N.; Uda, H.; Kuriki, T. Synthesis and absolute stereochemistry of (+)-adociaquinones A and B. Tet- rahedron Asymmetry 1995, 6, 375.
153. Kanematsu, K.; Soejima, S.; Wang, G. Formal total synthesis of xestoqui- none via furan ring transfer reaction strategy. Tetrahedron Lett. 1991, 32, 4761.
154. Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. Total synthesis and absolute stereochemistry of (+)-xestoquinone and xestoquinol. J. Org. Chem. 1990, 55, 3158.
155. Kobayashi, J.; Hirase, T.; Shigemori, H.; Ishibashi, M.; Bae, M. A.; Tsuji, T.; Sasaki, T. New pentacyclic compounds from the okinawan marine sponge Xestospongia sapra. J. Nat. Prod. 1992, 55, 994.
156. Gianinni, C.; Debitus, C.; Lucas, R.; Ubeda, A.; Payá, M.; Hooper, J. N. A.; D'Auria, M. V. New sesquiterpene derivatives from the sponge Dysidea spe- cies with a selective inhibitor profile against human phospholipase A2 and other leukocyte functions. J. Nat. Prod. 2001, 64, 612.
157. de Guzman, 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 hydroxyquinone from a philippine Dysidea sponge. J. Org. Chem. 1998, 63, 8042.
158. Mitome, H.; Nagasawa, T.; Miyaoka, H.; Yamada, Y.; van Soest, R. W. M. A new sesquiterpenoid quinone and other related compounds from the oki- nawan marine sponge Dactylospongia elegans. J. Nat. Prod. 2003, 66, 46.
159. Chambers, C.; Trauner, H.; Trauner, D. Concise total synthesis of (-)- frondosin B using a novel palladium-catalyzed cyclization. Angew. Chem. Int. Ed. 2002, 41, 1569.
160. Chambers, C.; Trauner, H.; Trauner, D. Palladium-catalyzed couplings to nucleophilic heteroarenes: the total synthesis of ()-frondosin B. Tetrahe- dron 2004, 60, 9675.
161. 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 inter- leukin-8 receptors. Tetrahedron 1997, 53, 5047.
162. Li, X.; Keon, A. E.; Sullivan, J. A.; Ovaska, T. V. Studies toward frondosin A and its analogues. Formal Total Synthesis of (±)-Frondosin A. Org.Lett. 2008, 10, 3287.
163. Mehta, G.; Likhite, N. S. A total synthesis of (±)-frondosins A and B. Tetra- hedron Lett. 2008, 49, 7113.
164. Trost, B. M.; Hu, Y.; Horne, D. B. Total synthesis of (+)-Frondosin A. application of the Ru-Catalyzed [5+2] cycloaddition. J. Am. Chem. Soc. 2007, 129, 11781.
165. Hallock, Y. F.; Cardellina, J. H.; Boyd, M. R. (-)-Frondosins A and D, HIV- inhibitory sesquiterpene hydroquinone derivatives from Euryspongia sp. Nat. Prod. Lett. 1998, 11, 153.
166. Amade, P.; Chevelot, L.; Perzanowski, H. P.; Scheuer, P.J. A Dimer of Puupehenone. Helv. Chim. Acta 1983, 66, 1672.
167. 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.
168. Rodriguez, A. D.; Yoshida, W. Y.; Scheur, J. Popolohuanone A and B. two new sesquiterpenoid aminoquinones from a pacific sponge Dysidea sp. Tetrahedron 1990, 46, 8025.
169. Alvi, K. A.; Díaz, M. C.; Crews, P. Evaluation of new sesquiterpene quinones from two Dysidea sponge species as inhibitors of protein tyrosine kinase. J. Org. Chem. 1992, 57, 6604.
170. Carney, J. R.; Scheuer, P. J. Popolohuanone E, a topoisomerase-II inhibitor with selective lung tumor cytotoxicity from the Pohnpei sponge Dysidea sp. Tetrahedron Lett. 1993, 34, 3727.
171. Kawano, H.; Itoh, M.; Katoh, T.; Terahima, S. Studies toward the synthesis of popolohuanone E: Synthesis of natural (+)-arenarol related to the proposed biogenetic precursor of popolohuanone E. Tetrahedron Lett. 1997, 38, 7769.
172. Anderson, J. C.; Denton, R. M.; Wilson, C. A biomimetic strategy for the synthesis of the tricyclic dibenzofuran-1,4-dione core of popolohuanone E. Org. Lett. 2005, 7, 123.
173. Katoh, T.; Nakatani, M.; Shikita, S.; Sampe, R.; Ishiwata, A.; Ohmori, O.; Nakamura, M.; Terashima, S. Studies toward the total synthesis of popolo- huanone E: Enantioselective synthesis of 8-O-Methylpopolohuanone E. Org. Lett. 2001, 3, 2701.
174. 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.
175. Bernet, A.; Seifert, K. A new approach to sesquiterpene arenes of the 9,11- drimenyl type (=[(1E,2RS,4aRS,8aRS)-octahydro-2,5,5,8a- tetramethylnaphthalen-1(2H)-ylidene] methyl type). Helv. Chim. Acta 2006, 89, 784.
176. Kobayashi, J.; Madono, T.; Shigemori, I. 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.
177. 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.
178. Yang, L.; Williams, D. E.; Mui, A.; Ong, C.; Krystal, G.; van Soest, R.; Andersen, R. J. Synthesis of pelorol and analogues: Activators of the inositol 5-Phosphatase SHIP. Org. Lett. 2005, 7, 1073.
179. Blunt, J. W.; Copp, B. R.; Munro, M. H.; Northcote, P. T.; Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 2008, 25.
180. Dave, M.-N.; Kusumi, T.; Ishitsuka, M.; Iwashita, T.; Kakisawa, M. A piscicidal chromanol and a chromenol from the brown alga Dictyopteris un- dulata. Heterocycles 1984, 22, 2301.
181. Wright, A. E.; Cross, S. S.; Burres, N. S.; Koehn, F. Antivial and antitumor terpene hydroquinones from marine sponge and methods of use. Harbor Branch Oceanographics Institution, Inc., USA, PCT WO 9112250 A1 August 22, 1991.
182. Suna, H.; Arai, M.; Tsubotani, Y.; Hayashi, A.; Setiawan, A. Dysideamine, a new sesquiterpene aminoquinone, protects hippocampal neuronal cells against iodoacetic acid-induced cell death. Bioorg. Med. Chem. 2009, 17, 3968.