Acetylenic aquatic anticancer agents and related compounds

Natural Product Communications

Volumn 1, Issue 9, 2006, Pages 773-811

  Dembitsky, Valery M ^a   Levitsky, Dmitri O ^b   Gloriozova, Tatyana A ^c   Poroikov, Vladimir V ^c  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITÉ DE NANTES   (France)

^c INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

Author keywords

Acetogenins; Acetylenic; Activity; Alcohols; Algae; Alkaloids; Anticancer; Aquatic; Carotenoids; Cyanobacteria; Cytotoxic; Fatty Acids; Fish; Glycerols; Lipids; Metabolites; Polyacetylenes; Polyethers; Predicted; Sesquiterpens; Sponges; Sterols

Indexed keywords

EID: 33845342036     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0600100914     Document Type: Review

References (300)

1. Dembitsky VM, Levitsky DO. (2006) Acetylenic terrestrial anticancer agents. Natural Product Communications, 1, 405-429.
2. Simmons TL, Andrianasolo E, McPhail K, Flatt P, Gerwick WH. (2005) Marine natural products as anticancer drugs. Molecular and Cancer Therapy, 4, 333-342
3. (b) Mayer AM, Gustafson KR. (2004) Marine pharmacology in 2001-2: antitumor and cytotoxic compounds. European Journal of Cancer, 40, 2676-2704.
4. Mayer AM, Gustafson KR. (2003) Marine pharmacology in 2000: Antitumor and cytotoxic compounds. International Journal of Cancer, 105, 291-299
5. (b) Kim J, Park EJ. (2002) Cytotoxic anticancer candidates from natural resources. Current Medicinal Chemistry: Anti-Cancer Agents, 2, 485-537.
6. Cragg GM, Newman DJ. (1999) Discovery and development of antineoplastic agents from natural sources. Cancer Investigation, 17, 153-163
7. (b) Fusetani N. (2004) Search for drug leads from Japanese marine invertebrates. Yuki Gosei Kagaku Kyokaishi, 62, 1073-1079.
8. Belarbiel H, Contreras GA, Chisti Y, Garcia CF, Molina GE. (2003) Producing drugs from marine sponges. Biotechnological Advances, 21, 585-598
9. (b) Dembitsky VM. (2004) Astonishing diversity of natural surfactants. 1. Glycosides of fatty acids and alcohols, Lipids, 39, 933-953.
10. Arif JM, Al-Hazzani AA, Kunhi M, Al-Khodairy F. (2004) Novel marine compounds: Anticancer or genotoxic? Journal of Biomedicine and Biotechnology, 2, 93-98
11. (b) Dembitsky VM. (2005) Astonishing diversity of natural surfactants. 2. Polyether glycosidic ionophores and macrocyclic glycosides, Lipids, 40, 219-248.
12. Dembitsky VM. (2005) Astonishing diversity of natural surfactants. 3. Carotenoid glycosides and isoprenoid glycolipids, Lipids, 40, 535-557
13. (b) Amador ML, Jimeno J, Paz-Ares L, Cortes-Funes H, Hidalgo M. (2003) Progress in the development and acquisition of anticancer agents from marine sources. Anne of Oncology, 14, 1607-1615.
14. Kim J, Park EJ. (2002) Cytotoxic anticancer candidates from natural resources. Current Medicinal Chemistry: Anti-Cancer Agents, 2, 485-537
15. (b) Dembitsky VM. (2006) Astonishing diversity of natural surfactants. 7. Biological active hemi- and monoterpenoid glycosides. Lipids, 41, 1-27
16. Wilmotte A. (1994) Molecular evolution and taxonomy of the cyanobacteria. Advances in Photosynthesis, 1, 1-25
17. (b) Skulberg OM, Carmichael WW, Codd GA, Skulberg R. (1993) Taxonomy of toxic Cyanophyceae (Cyanobacteria ). Algal Toxins Seafood Drinking Water, 145-164.
18. Inoue I. (2004) Biological evolution and symbiosis. IDEM, 58, 29-35
19. (b) Maeda H, Higashibaba D, Usui C, Ueno K. (2003) Study on microorganism evolution by DNA analysis. Gekkan Chikyu, Gogai, 42, 193-196.
20. Kuroiwa T. (2000) Origin and evolution of chloroplasts. Hikari ga Hiraku Seimei Kagaku, 2, 89-105
21. (b) Adams, DG. (2000) Cyanobacterial phylogeny and development: questions and challenges. Prokaryotic Development, 51-81.
22. Burja AM, Banaigs B, Abou-Mansour E, Grant BJ, Wright PC. (2001) Marine cyanobacteria: A prolific source of natural products. Tetrahedron, 57, 9347-9377
23. (b) Gerwick WH, Tong TL, Sitachitta N. (2001) In The Alkaloids: Chemistry and Biology; Cordell GA., Ed.; Academic Press: San Diego, Vol. 57, Chapter 2, pp 75-184.
24. Nagatsu A. (1997) Components of blue-green algae. Nagoya-shiritsu Daigaku Yakugakubu Kenkyu Nenpo, 44, 1-12
25. (b) Kent UM, Jushchyshyn MI, Hollenberg PF. (2001) Mechanism-based inactivators as probes of cytochrome P450 structure and function. Current Drug Metabolism, 2, 215-243.
26. Macdonald RL, Greenfield LJ (1997) Mechanisms of action of new antiepileptic drugs. Current Opinion in Neurology, 10, 121-128
27. (b) Kalviainen R, Keranen T, Riekkinen PJ. (1993) Place of newer antiepileptic drugs in the treatment of epilepsy. Drugs, 46, 1009-1024.
28. Berry DE, Chan JA, Mackenzie L, Hecht SM.(1991) 9-Octadecynoic acid - a novel DNA-binding agent. Chemical Research in Toxicology, 4, 195-198
29. (b) Ehrhart G. (1936) Unsaturated group in therapeutic substances. Medical und Chemical Abhandl. Medico-Chemical Forschungsstatten I. G. Farbenind, 3, 366-374.
30. Luesch H, Yoshida WY, Moore RE, Paul VJ. (2000) Apramides A-G, novel lipopeptides from the marine cyanobacterium Lyngbya majuscula. Journal of Natural Products, 63, 1106-1112
31. (b) Williams PG, Yoshida WY, Moore RE, Paul VJ. (2004) Micromide and guamamide: cytotoxic alkaloids from a species of the marine cyanobacterium Symploca. Journal of Natural Products, 67, 49-53.
32. Jimenez JI, Scheuer PJ. (2001) New lipopeptides from the Caribbean cyanobacterium Lyngbya majuscula. Journal of Natural Products, 64, 200-203.
33. Hooper GJ, Orjala J, Schatzman RC, Gerwick WH. (1998) Carmabins A and B, new lipopeptides from the Caribbean cyanobacterium Lyngbya majuscula. Journal of Natural Products, 61, 529-533.
34. Horgen FD, Yoshida WY, Scheuer PJ. (2000) Malevamides A-C, new depsipeptides from the marine cyanobacterium Symploca laete-viridis. Journal of Natural Products, 63, 461-467.
35. Nogle LM, Gerwick WH. (2002) Isolation of four new cyclic depsipeptides, antanapeptins A-D, and dolastatin 16 from a Madagascan collection of Lyngbya majuscula. Journal of Natural Products, 65, 21-24.
36. Luesch H, Pangilinan RY, Moore RE, Paul VJ. (2001) Pitipeptolides A and B, new cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula. Journal of Natural Products, 64, 304-307.
37. Sitachitta N, Williamson RT, Gerwick WH. (2000) Yanucamides A and B, two new depsipeptides from an assemblage of the marine cyanobacteria Lyngbya majuscula and Schizothrix species. Journal of Natural Products, 63, 197-200.
38. Williams PG, Yoshida WY, Quon MK, Moore RE, Paul VJ. (2003) Ulongapeptin, a cytotoxic cyclic depsipeptide from a Palauan marine cyanobacterium Lyngbya sp. Journal of Natural Products, 66, 651-654.
39. Han B, Goeger D, Maier CS, Gerwick WH. (2005) The wewakpeptins, cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. Journal of Organic Chemistry, 70, 3133-3139.
40. Tan LT, Sitachitta N, Gerwick WH. (2003) The guineamides, novel cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. Journal of Natural Products, 66, 764-771.
41. Wan F, Erickson KL. (2001) Georgamide, a new cyclic depsipeptide with an alkynoic acid residue from an Australian cyanobacterium. Journal of Natural Products, 64, 143-146.
42. Filimonov D, Poroikov V, Borodina Yu, Gloriozova T. (1999) Chemical Similarity Assessment through multilevel neighborhoods of atoms: definition and comparison with the other descriptors. Journal of Chemical Information and Computer Sciences, 39, 666-670
43. (b) Poroikov VV, Filimonov DA, Borodina YuV, Lagunin AA, Kos A. (2000) Robustness of biological activity spectra predicting by computer program PASS for non-congeneric sets of chemical compounds. Journal of Chemical Information and Computer Sciences, 40, 1349-1355.
44. Anzali S, Barnickel G, Cezanne B, Krug M, Filimonov D, Poroikov V. (2001) Discriminating between drugs and nondrugs by Prediction of activity spectra for substances (PASS). Journal of Medicinal Chemistry, 44, 2432-2437
45. (b) Poroikov VV, Filimonov DA. (2002) How to acquire new biological activities in old compounds by computer prediction. Journal of Computer-Aided Molecular Design, 16, 819-824.
46. Stepanchikova AV, Lagunin AA, Filimonov DA, Poroikov V. (2003) Prediction of biological activity spectra for substances: Evaluation on the diverse sets of drug-like structures. Current Medicinal Chemistry, 10, 225-233
47. (b) Geronikaki A, Dearden J, Filimonov D, Galaeva I, Garibova T, Gloriozova T, Krajneva V, Lagunin A, Macaev F, Molodavkin G, Poroikov V, Pogrebnoi S, Shepeli F, Voronina T, TsitlakidouM, Vlad L. (2004) Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation. Journal of Medicinal Chemistry, 47, 2870-2876.
48. Poroikov V, Filimonov D. (2005) PASS: Prediction of Biological Activity Spectra for Substances. In:Predictive Toxicology . Helma C. (Ed), Taylor & Francis, 459-478; (h) http://www.ibmc.msk.ru/PASS.
49. Dembitsky VM, Gloriozova T, Poroikov VV. (2005). Novel antitumor agents: marine sponge alkaloids, their synthetic analogues and derivatives. Mini-Reviews in Medicinal Chemistry, 5, 319-336.
50. Xu N, Fan X, Yan X, Tseng CK. (2004) Screening marine algae from China for their antitumor activities. Journal of Applied Phycology, 16, 451-456.
51. Xu N, Fan X, Han L, Yan X, Zeng C. (2001) Screening marine algae from Shandong coast for antitumor activity. Haiyang Yu Huzhao, 32, 408-413.
52. Harada H, Kamei Y. (1998) Dose-dependent selective cytotoxicity of extracts from marine green alga, Cladophoropsis vaucheriaeformis, against mouse leukemia L1210 cells. Biological & Pharmaceutical Bulletin, 21, 386-389.
53. Nemanich JW, Theiler RF, Hager LP. (1978) The occurrence of cytotoxic compounds in marine organisms. Editor(s): Kaul, PN, Sindermann, CJ. Drugs Food Sea Myth Reality? International Symposium, Meeting Date 1977, pp. 123-136. Publisher: University of Oklahoma, Norman, Oklahoma.
54. Ktari L, Longeon A, Guyot M. (2001) Biological activities of marine algae from Tunisian coasts. Journal de Recherche Oceanographique (France), 26, 37-41.
55. Mendonça P. (1998) Estudos farmacológicos do extrato da alga Liagora farinosa. Dissertação, pp.156
56. (b) Mendonça P, Freitas JC. (2000) Toxic activity in the organic extract of the seaweed Liagora farinosa (Rhodophyta., Nemaliales). Brazilian Journal of Medical and Biological Research, 27, 131-142.
57. Lad W. (1991) Acaricidal activity of 5 marine algae extracts on female Boophilus microplus (Acari, Ixodidae). Florida Entomologist, 74, 404-408.
58. Mizukoshi S, Kato F, Matsuoka H, Nakamura K, Noda H. (1995) Immunosuppressive effects of marine algae on experimental murine models. Nippon Suisan Gakkaishi, 61, 889-894.
59. Paul VJ, Fenical W. (1980) Toxic acetylene-containing lipids from the red marine alga Liagora farinosa Lamouroux. Tetrahedron Letters, 21, 3327-3330
60. (b) Nugteren DH, Christ-Hazelhof E. (1987) Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesis. Prostaglandins, 33, 403-417.
61. Soliman FM, Fathy MM, Moussa MY. (2000) Phytochemical and biological investigation of the green alga: Caulerpa prolifera Lamx. Bulletin of the Faculty of Pharmacy (Cairo University), 38, 99-107.
62. Barbier P, Guise S, Huitorel P, Amade P, Pesando D, Briand C, Peyrot V. (2001) Caulerpenyne from Caulerpa taxifolia has an antiproliferative activity on tumor cell line SK-N-SH and modifies the microtubule network. Life Sciences, 70, 415-429.
63. Fischel JL, Lemee R, Formento P, Caldani C, Moll JL, Pesando D, Meinesz A, Grelier P, Pietra F. (1995) Cell-growth-inhibitory effects of caulerpenyne, a sesquiterpenoid from the marine alga Caulerpa taxifolia. Anticancer Research, 15, 2155-2160.
64. Valls R, Lemee R, Piovetti L, Amade P, Bouaicha N. (1995) Determination of caulerpenyne, a toxin of the green alga Caulerpa taxifolia. Acta Botanica Gallica, 142, 131-135.
65. Guerriero A, Marchetti F, D'Ambrosio M, Senesi S, Dini F, Pietra F. (1993) New ecotoxicologically and biogenetically relevant terpenes of the tropical green seaweed Caulerpa taxifolia which is invading the Mediterranean. Helvetica Chimica Acta, 76, 855-864.
66. Lemee R, Pesando D, Durand-Clement M, Dubreuil A, Meinesz A, Guerriero A, Pietra F. (1993) Preliminary survey of toxicity of the green alga Caulerpa taxifolia introduced into the Mediterranean. Journal of Applied Phycology, 5, 485-493
67. (b) Jung V, Thibaut T, Meinesz A, Pohnert G. (2002) Comparison of the wound-activated transformation of caulerpenyne by invasive and noninvasive Caulerpa species of the Mediterranean. Journal of Chemical Ecology, 28, 2091-2105.
68. De Napoli L, Fattorusso E, Magno S, Mayol L. (1981) Furocaulerpin, a new acetylenic sesquiterpenoid from the green alga Caulerpa prolifera. Experientia, 37, 1132.
69. Mendiola J, Hernández H, Sariego I, González Z, Rojas L, Robles Laurencio R, Otero A, Ramírez A, Marcos Z, Hernández A. (2004) In vitro antimalarial activity and cytotoxicity against human macrophage cell line of extracts of marine organisms collected in the North West coast of Cuba. Plantas medicinales, Reviews de la Cuba Farmaceutica, Supl. Esp., 23-28
70. (b) Sabina H, Tasneem S, Sambreen Kausar Y, Choudhary MI, Aliya R (2005) Antileishmanial activity in the crude extract of various seaweeds from the coast of Karachi, Pakistan Pakistan Journal of Botany, 37, 163-168.
71. Erickson KL. (1983) Constituents of Laurencia. Marine Natural Products: Chemical and Biological Perspectives, 5, 131-257
72. (b) Kurosawa E, Suzuki M. (1983) Metabolic products of red seaweed, Laurencia. Kagaku to Seibutsu, 21, 23-32.
73. Fukuzawa A, Kurosawa E. (1979) On the structures of laurallene and laurepoxide, constituents of Laurencia nipponica Yamada, and studies on growth locality of the species. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 22, 611-618
74. (b) Howard BM, Fenical W. (1981) The scope and diversity of terpenoid biosynthesis by the marine alga Laurencia. Progress in Phytochemistry, 7, 263-300.
75. Aknin M.(1994) New secondary metabolites isolated from marine organisms from the coast of Senegal. A means for studying the chemistry of the India Oceans. Journal of Nature, 6, 12-20
76. (b) Koenig GM, Wright AD. (1997) Marine and aquatic environments: sources of novel and biologically active secondary metabolites. Chemika Chronika, Genike Ekdose (Greece), 59, 106-108.
77. Koenig GM, Wright AD. (1997) Marine organisms. Producers of pharmacologically active secondary substances. Pharmazie in Unserer Zeit, 26, 281-288
78. (b) Crespo Pereira R, Laneuville Teixeira V. (1999) Sesquiterpenes of the marine algae Laurencia Lamouroux (Ceramiales, Rhodophyta). Quimica Nova, 22, 369-374.
79. Gonzalez AG, Martin JD, Norte M, Rivera P, Ruano JZ. (1984) Marine natural products from the Atlantic zone. 41. Two new C15 acetylenes from the marine red alga Laurencia obtusa. Tetrahedron, 40, 3443-3447
80. (b) Mihopoulos N, Vagias C, Scoullos M, Roussis V. (1999) Laurencienyne B, a new acetylenic cyclic ether from the red alga Laurencia obtusa. Natural Product Letters, 13, 151-156.
81. Aydogmus Z, Imre S. (1999) A new halogenated C15 non-terpenoid compound from the marine red alga, Laurencia obtusa. Acta Pharmaceutica Turcica, 41, 93-95
82. (b) Suzuki T, Koizumi K, Suzuki M, Kurosawa E. (1983) Constituents of marine plants. 57. Kumausynes and deacetylkumausynes, four new halogenated C-15 acetylenes from the red alga Laurencia nipponica Yamada. Chemistry Letters, 10, 1643-1644.
83. Dilip de Silva E, Schwartz RE, Scheuer PJ, Shoolery JN. (1983) Srilankenyne, a new metabolite from the sea hare Aplysia oculifera. Journal of Organic Chemistry, 48, 395-396
84. (b) Fukuzawa A, Takasugi Y, Murai A, Nakamura M, Tamura M. (1991) Biosynthesis of medium-sized bromo ethers isolated from the red alga, Laurencia nipponica. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 33, 345-352.
85. Aydogmus Z, Imre S, Ersoy L, Wray V. (2004) Halogenated secondary metabolites from Laurencia obtusa. Natural Product Research, 18, 43-49
86. (b) Imre S, Oztunc A, Islimyeli S. (1987) Chemical investigation of some marine organisms collected from Turkish waters. Turk Kimya Dergisi, 11, 119-128.
87. Dembitsky VM, Tolstikov AG, Tolstikov GA. (2003) Natural halogenated non-terpenoid C15 acetogenins of marine organisms. Chemistry of Sustainable Development, 11, 329-340
88. (b) Bermejo A, Figadere B, Zafra-Polo MC, Barrachina I, Estornell E, Cortes D. (2005) Acetogenins from Annonaceae. Recent progress in isolation, synthesis, and mechanisms of action. Natural Product Reports, 22, 269-303.
89. Li Y, Fu L. (2004) Antitumoral effects of Annonaceous acetogenins. Zhongguo Yaolixue Tongbao, 20, 245-247
90. (b) Pietra F. (1993) Chance: the natural products of the marine area Il Rogiolo, and other stories. Gazzetta Chimica Italiana, 123, 343-358.
91. Kitagawa I, Kobayashi M. (1989) Antitumor natural products isolated from marine organisms. Gan to Kagaku Ryoho, 16, 1-8
92. (b) Uemura D. (1987) Antitumor polyethermacrolides produced by sponges. Kagaku, Zokan (Kyoto), 111, 145-153.
93. Iliopoulou D, Vagias C, Harvala C, Roussis V. (2002) C15 acetogenins from the red alga Laurencia obtusa. Phytochemistry, 59, 111-116
94. (b) Kaul PN, Kulkarni SK, Kurosawa E. (1978) Novel substances of marine origin as drug metabolism inhibitors. Journal of Pharmacy and Pharmacology, 30, 589-590
95. (c) Fukuzawa A, Masamune T. (1981) Laurepinnacin and isolaurepinnacin, new acetylenic cyclic ethers from the marine red alga Laurencia pinnata Yamada. Tetrahedron Letters, 22, 4081-4084.
96. Ladygin VG. (2002) Current state of carotenoid biosynthesis in chloroplasts of eukaryotes. Zhurnal Obshchei Biologii, 63, 299-325
97. (b) Miki W. (1992) Recent advances in carotenoid studies-metabolisms and bioactivities. Journal of Nutrition and Science of Vitaminology (Tokyo). Spec No: 469-472.
98. Romer S. (1999) Carotenoids in higher plants and algae. NATO Science Series, 3: High Technology, 64, 217-223
99. (b) Liaaen- Jensen S. (1989) Studies on algal carotenoids. Pure and Applied Chemistry, 61, 369-372
100. (e) Liaaen-Jensen S. (1985) Carotenoids of lower plants - recent progress. Pure and Applied Chemistry, 57, 649-658
101. Weedon BCL. (1967) Carotenoids. Recent advances. Chemistry in Britain, 3, 424-432.
102. Maoka T, Tsushima M, Nishino H. (2002) Isolation and characterization of dinochrome A and B, anti-carcinogenic active carotenoids from the fresh water red tide Peridinium bipes. Chemical & Pharmaceutical Bulletin, 50, 1630-1633.
103. Tsushima M, Maoka T, Katsuyama M, Kozuka M, Matsuno T, Tokuda H, Nishino H, Iwashima A. (1995) Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters. Biological & Pharmaceutical Bulletin, 18, 227-233.
104. Wu JT, Kuo-Huang LL, Lee J. (1998) Algicidal effect of Peridinium bipes on Microcystis aeruginosa. Current Microbiology, 37, 257-261.
105. Fiksdahl A, Liaaen-Jensen S. (1988) Algal carotenoids. Part 38. Diacetylenic caroteneoids from Euglena viridis. Phytochemistry, 27, 1447-1450
106. (b) Heelis DV, Kernick W, Phillips GO, Davies K. (1979) Separation and identification of the carotenoid pigments of stigmata isolated from light-grown cells of Euglena gracilis strain Z. Archiv fuer Mikrobiologie, 121, 207-211.
107. Nitsche H. (1973) Heteroxanthin in Euglena gracilis. Archiv fuer Mikrobiologie, 90, 151-155
108. (b) Strain HH, Aitzetmueller K, Svec WA, Katz JJ. (1970) Structure of heteroxanthine, a unique xanthophyll from the Xanthophyceae (Heterokontae). Journal of the Chemical Society, Chemical Communications, 14, 876-877.
109. Strain HH, Benton FL, Grandolfo MC, Aitzetmueller K, Svec WA, Katz JJ. (1970) Heteroxanthine, diatoxanthine, and diadinoxanthine from Tribonema aequale. Phytochemistry, 9, 2561-2565.
110. Fiksdahl A, Withers N, Guillard RRL, Liaaen-Jensen S. (1984) Algal carotenoids. Part 31. Carotenoids of the Raphidophyceae - a chemosystematic contribution. Comparative Biochemistry and Physiology, 78B, 265-271
111. (b) Buchel C, Wilhelm C, Lenartz- Weiler I. (1988) The molecular analysis of the light adaptation reactions in the yellow-green alga Pleurochloris meiringensis (Xanthophyceae). Botanica Acta, 101, 306-310.
112. Oono M, Kikuchi K, Oonishi S, Nishino H, Tsushima Y. (1995) Anticancer agents containing carotenoids. Japan Kokai Tokkyo Koho, 5 pp. Japanese Patent: JP 07101872 A2 19950418 Heisei. Application: JP 93-248267 19931004.
113. Youssef DTA, Yoshida WY, Kelly M, Scheuer PJ. (2000) Polyacetylenes from a Red Sea sponge Callyspongia species. Journal of Natural Products, 63, 1406-1410.
114. Hallock YF, Cardellina JH, 2nd, Balaschak MS, Alexander MR, Prather TR, Shoemaker RH, Boyd MR. (1995) Antitumor activity and stereochemistry of acetylenic alcohols from the sponge Cribrochalina vasculum. Journal of Natural Products, 58, 1801-1807.
115. Gunasekera SP, Faircloth GT, Wright AE, Thompson WC, Burres N. (1991) Immunosuppressant and antitumor acetylenic alcohols from Cribrochalina vasculum. 6 pp. US Patent 5073572 A 19911217 Application: US 90-481475 19900216
116. (b) Gunasekera SP, Faircloth GT. (1990) New acetylenic alcohols from the sponge Cribrochalina vasculum. Journal of Organic Chemistry, 55, 6223-6225.
117. Zhou G-X, Molinski T. (2003) Long-chain acetylenic ketones from the Micronesian sponge Haliclona sp. Importance of the 1- yn-3-ol group for antitumor activity. Marine Drugs, 1, 46-53
118. (b) Rashid M, Gustafson KR, Boyd MR. (2000) Pellynol I, a new cytotoxic polyacetylene from the sponge Pellina sp. Natural Product Letters, 14, 387-392
119. Fu X., Abbas SA., Schmitz FJ, Vidavsky I, Gross ML, Laney M, Schatzman RC, Cabuslay RD. (1997) New acetylenic metabolites from the marine sponge Pellina triangulate, Tetrahedron, 53, 799-814.
120. Watanabe K, Tsuda Y, Yamane Y, Takahashi K, Iguchi K, Naoki H, Fujita T. (2000) Structures and enantiomeric ratios of strongylodiols A-G, new diynediols from the Okinawan marine sponge Strongylophora sp. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 42, 367-372
121. (b) Watanabe K, Tsuda Y, Hamada M, Omori M, Mori G, Iguchi K, Naoki H, Fujita T, Van Soest RWM. (2005) Acetylenic strongylodiols from a Petrosia (Strongylophora) Okinawan marine sponge. Journal of Natural Products, 68, \ 1001-1005.
122. Kim JS, Lim YJ, Im KS, Jung JH, Shim CJ, Lee CO, Hong J, Lee H. (1999) Cytotoxic polyacetylenes from the marine sponge Petrosia sp. Journal of Natural Products, 62, 554-559
123. (b) Kim JS, Im KS, Jung JH, Kim Y-L, Kim J, Shim CJ, Lee C-O. (1998) New bioactive polyacetylenes from the marine sponge Petrosia sp. Tetrahedron, 54, 3151-3158.
124. Kim D-K, Lee M-Y, Lee HS, Lee DS, Lee J-R, Lee B-J, Jung JH. (2002) Polyacetylenes from a marine sponge Petrosia sp. inhibit DNA replication at the level of initiation. Cancer Letters (Shannon, Ireland), 185, 95-101.
125. (b) Choi HJ, Bae S-J, Kim ND, Jung JH, Choi YH. (2004) Induction of apoptosis by dideoxypetrosynol A, a polyacetylene from the sponge Petrosia sp., in human skin melanoma cells. International Journal of Molecular Medicine, 14, 1091-1096
126. Aoki S, Matsui K, Murakami N, Nakajima T, Kobayashi M. (2001) Neuronal differentiation inducing activity and synthetic study of lembehyne A, a novel polyacetylene, isolated from a marine sponge of Haliclona sp. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 43, 305-310
127. (b) Aoki S, Matsui K, Tanaka K, Satari R, Kobayashi M. (2000) Lembehyne A, a novel neuritogenic polyacetylene, from a marine sponge of Haliclona sp. Tetrahedron, 56, 9945-9948.
128. Aoki S, Matsui K, Takata T, Hong W, Kobayashi M. (2001) Lembehyne A, a spongean polyacetylene, induces neuronal differentiation in neuroblastoma cell. Biochemical and Biophysical Research Communications, 289, 558-563
129. (b) Aoki S, Matsui K, Takata T, Kobayashi M. (2003) In situ photoaffinity labeling of the target protein for lembehyne A, a neuronal differentiation inducer. FEBS Letters, 544, 223-227
130. Aoki S. (2004) Searching for new candidates for cancer chemotherapy from natural products and analysis of those target molecules. Natural Medicines (Tokyo), 58, 251-257.
131. Ortega MJ, Zubia E, Carballo JL, Salva J. (1996) Fulvinol, a new long-chain diacetylenic metabolite from the sponge Reniera fulva. Journal of Natural Products, 59, 1069-1071.
132. Kobayashi M, Mahmud T, Tajima H, Wang W, Aoki S, Nakagawa S, Mayumi T, Kitagawa I. (1996) Marine natural products. XXXVI. Biologically active polyacetylenes, adociacetylenes A, B, C, and D, from an Okinawan marine sponge of Adocia sp. Chemical & Pharmaceutical Bulletin, 44, 720-724.
133. Isaacs S, Kashman Y, Loya S, Hizi A, Loya Y. (1993) Petrosynol and petrosolic acid, two novel natural inhibitors of the reverse transcriptase of human immunodeficiency virus from Petrosia sp. Tetrahedron, 49, 10435-10438
134. (b) Fusetani N, Shiragaki T, Matsunaga S, Hashimoto K. (1987) Bioactive marine metabolites. 20. Petrosynol and petrosynone, antimicrobial C30 polyacetylenes from the marine sponge Petrosia sp.: determination of the absolute configuration. Tetrahedron Letters, 28, 4313-4314.
135. Shen Y-C, Prakash CVS. (2000) Two new acetylenic derivatives and a new meroditerpenoid from a Taiwanese marine sponge Strongylophora durissima. Journal of Natural Products, 63, 1686-1688
136. (b) Wright AE, McConnell OJ, Kohmoto S, Lui MS, Thompson W, Snader KM. (1987) Duryne, a new cytotoxic agent from the marine sponge Cribrochalina dura. Tetrahedron Letters, 28, 1377-1380
137. Wright AE, Thompson WC, Lui MS. (1987) Novel polyacetylene compositions extracted from the marine sponge, Cribrochalina dura, and their use as antitumor agents. PCT International Application, 24 pp. WO 8704703 A1 19870813.
138. Dai J-R, Hallock YF, Cardellina JH, II, Boyd MR. (1996) Vasculyne, a new cytotoxic acetylenic alcohol from the marine sponge Cribrochalina vasculum. Journal of Natural Products, 59, 88-89.
139. Shin J, Seo Y, Cho KW, Rho J-R, Paul VJ. (1998) Osirisynes A-F, highly oxygenated polyacetylenes from the sponge Haliclona osiris. Tetrahedron, 54, 8711-8720
140. (b) Shin J, Seo Y, Cho KW, Rho J-R, Paul VJ. (1998) Osirisynes A-F, highly oxygenated polyacetylenes from the sponge Haliclona osiris. Tetrahedron, 54, 14636-14643.
141. Ishiyama H, Ishibashi M, Kobayashi J. (1996) Taurospongin A, novel acetylene derivative from Okinawan marine sponge Hippospongia sp. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 38, 469-474.
142. Youssef DTA, Van Soest RWM, Fusetani N. (2003) Callyspongamide A, a new cytotoxic polyacetylenic amide from the Red Sea sponge Callyspongia fistularis. Journal of Natural Products, 66, 861-862.
143. Youssef DTA, Van Soest RWM, Fusetani N. (2003) Callyspongenols A-C, new cytotoxic C22-polyacetylenic alcohols from a Red Sea sponge, Callyspongia species. Journal of Natural Products, 66, 679-681
144. (b) Rotem M, Kashman Y. (1979) New polyacetylenes from the sponge Siphonochalina sp. Tetrahedron Letters, 3193-3196.
145. Lee H-S, Rho J-R, Sim CJ, Shin J. (2003) New acetylenic acids from a sponge of the genus Stelletta. Journal of Natural Products, 66, 566-568.
146. Schmitz FJ, Gopichand Y. (1978) (7E, 13, 15Z)-14, 16-Dibromo-7, 13, 15-hexadecatrien-5-ynoic acid. A novel dibromo acetylenic acid from the marine sponge Xestospongia muta. Tetrahedron Letters, 39, 3637-3640
147. (b) Ichiba T, Scheuer PJ, Kelly- Borges M. (1993) Sponge-derived polyunsaturated C16 di- and tribromo-carboxylic acids. Helvetica Chimica Acta, 76, 2814-2816.
148. Shin J, Seo Y, Cho KW. (1998) Five New Polyacetylenes from a Sponge of the Genus Petrosia. Journal of Natural Products, 61, 1268-1273.
149. Seo Y, Cho KW, Lee HS, Rho JR, Shin J. (1999) New acetylenic enol ethers of glycerol from the sponge Petrosia sp. Journal of Natural Products, 62, 122-126.
150. Rogers EW, Molinski TF. (2005) A cytotoxic carotenoid from the marine sponge Prianos osiros. Journal of Natural Products, 68, 450-452
151. (b) Kitamura A, Tanaka J, Higa T. (1996) New cytotoxic carotenoids from the sponge Phakellia stelliderma. Journal of Natural Toxins, 5, 219-224.
152. Matsuno T. (2001) Aquatic animal carotenoids. Fisheries Science, 67, 771-783
153. (b) Lee WL, Gilchrist BM. (1985) Carotenoid patterns in twenty-nine species of sponges in the order Poecilosclerida (Porifera: Demospongiae): a possible tool for chemosystematics. Marine Biology (Berlin), 86, 21-35.
154. Tanaka Y, Katayama T. (1977) Biochemical studies on the carotenoids in Porifera. The structure of a new carotenoid, tethyatene in sea sponge, Tethya amamensis. Nippon Suisan Gakkaishi, 43, 1229-1232
155. (b) Hertzberg S, Bergquist P, Liaaen- Jensen S. (1989) Carotenoid sulfates. 6. Further occurrence of sulfated carotenoids in Ianthella species (Desmospongia). Biochemical Systematics and Ecology, 17, 51-53.
156. Hertzberg S, Englert G, Bergguist P, Liaaen-Jensen S. (1986) Animal carotenoids. Part 30. Carotenoids of the sponge Polymastia granulosa (Hadromerida). Bulletin des Societes Chimiques Belges, 95, 801-814
157. (b) Czeczuga B. (1976) The carotenoids of fresh-water sponges of the genus Spongilla. Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Biologiques, 24, 469-471.
158. Liaaen-Jensen S, Renstroem B, Ramdahl T, Hallenstvet M, Bergquist P. (1982) Carotenoids of marine sponges. Biochemical Systematics and Ecology, 10, 167-174
159. (b) Tanaka Y, Soejima T, Katayama T. (1978) Biochemical studies of the carotenoids in porifera. Distribution of the carotenoids in porifera. Nippon Suisan Gakkaishi, 44, 1283-1285.
160. Aiello A, Fattorusso E, Menna M, Pansini M. (1995) Chemical analysis of the sponge Suberites massa coming from the Lagoon of Venice: isolation of a new diacetylenic carotenoid. Journal fuer Praktische Chemie/Chemiker-Zeitung, 337, 397-400
161. (b) Liaaen-Jensen S, Hertzberg S. (1995) Example 11: Carotenoid sulfates. Carotenoids, 1A, 283-286.
162. Hertzberg S, Bergquist P, Liaaen-Jensen S. (1989) Carotenoid sulfates. 6. Further occurrence of sulfated carotenoids in Ianthella species (Desmospongia). Biochemical Systematics and Ecology, 17, 51-53
163. (b) Tanaka Y, Inoue T. (1988) Occurrence of a new carotenoid 7, 8-didehydroaaptopurpurin in sea sponge Tedania digitata. Nippon Suisan Gakkaishi, 54, 155.
164. Litchfield C, Liaaen-Jensen S. (1980) Animal carotenoids. Part 23. Carotenoids of the marine sponge, Microciona prolifera. Comparative Biochemistry and Physiology, 66B, 359-65
165. (b) Tanaka Y, Katayama T. (1979) Biochemical studies on the carotenoids in Porifera. The structure of tedaniaxanthin. Part 2. Nippon Suisan Gakkaishi, 45, 633-634.
166. Tanaka Y, Katayama T. (1980) Biochemical studies on the carotenoids in porifera. The structure of isotedaniaxanthin. Nippon Suisan Gakkaishi, 46, 381-383
167. (b) Hamasaki T, Okukado N, Yamaguchi M. (1973) Two natural acetylenic aromatic carotenoids. Bulletin of the Chemical Society of Japan, 46, 1884-1885.
168. Zampella A, D'Auria MV, Minale L, Debitus C, Roussakis C. (1996) Callipeltoside A: A cytotoxic aminodeoxy sugarcontaining macrolide of a new type from the marine lithistida sponge Callipelta sp. Journal of the American Chemical Society, 118, 11085-11088
169. (b) Zampella A, D'Auria MV, Minale L, Debitus C. (1997) Callipeltosides B and C, two novel cytotoxic glycoside macrolides from a marine Lithistida sponge Callipelta sp. Tetrahedron, 53, 3243-3248.
170. Grassia A, Bruno I, Debitus C, Marzocco S, Pinto A, Gomez-Paloma L, Riccio R. (2001) Spongidepsin, a new cytotoxic macrolide from Spongia sp. Tetrahedron, 57, 6257-6260.
171. Gallimore WA, Kelly M, Scheuer PJ. (2001) Gelliusterols A-D, new acetylenic sterols from a sponge, Gellius species. Journal of Natural Products, 64, 741-744
172. (b) Steiner E, Djerassi C, Fattorusso E, Magno S, Mayol L, Santacroce C, Sica D. (1977) Isolation, structure determination and synthesis of new acetylenic steroids from the sponge Calyx nicaaensis. Helvetica Chimica Acta, 60, 475-481.
173. Onken D, Heublein D. (1970) Acetylenated steroids. Pharmazie, 25, 3-9
174. (b) Nagahisa A, Spencer RW, Orme-Johnson WH. (1983) Acetylenic mechanism-based inhibitors of cholesterol side chain cleavage by cytochrome P-450scc. Journal of Biological Chemistry, 258, 6721-6723.
175. Beress L. (1982) Biologically active compounds from coelenterates. Pure and Applied Chemistry, 54, 1981-1994
176. (b) Davies- Coleman MT, Beukes DR. (2004) Ten years of marine natural products research at Rhodes University. South African Journal of Science, 100, 539-544.
177. Venkateswarlu Y, Reddy NS, Venkatesham U. (2001) Novel bioactive compounds from the soft corals chemistry and biomedical applications. Recent Advances in Marine Biotechnology, 6, 101-129
178. (b) Ji Y-B, Wang Y, Lin W-H. (2004) Study on chemical constituents and biological activities of soft coral. Harbin Shangye Daxue Xuebao, Ziran Kexueban, 20, 261-265.
179. Anjaneyulu ASR, Rao GV. (1997) Chemical constituents of the soft coral species of Sarcophyton genus: a review. Journal of the Indian Chemical Society, 74, 272-278
180. (b) Anjaneyulu ASR, Rao GV. (1995) The chemical constituents of the soft coral species of Sinularia genus: a review. Journal of Scientific & Industrial Research, 54, 637-649.
181. Fusetani N, Toyoda T, Asai N, Matsunaga S, Maruyama T. (1996) Montiporic acids A and B, cytotoxic and antimicrobial polyacetylene carboxylic acids from eggs of the scleractinian coral Montipora digitata. Journal of Natural Products, 59, 796-797.
182. Alam N, Bae BH, Hong J, Lee CO, Im KS, Jung JH. (2001) Cytotoxic diacetylenes from the stony coral Montipora species. Journal of Natural Products, 64, 1059-1063.
183. Bae BH, Im KS, Choi WC, Hong J, Lee C-O, Choi JS, Son BW, Song J-I, Jung JH. (2000) New acetylenic compounds from the stony coral Montipora sp. Journal of Natural Products, 63, 1511-1514.
184. Higa T, Tanaka J, Kohagura T, Wauke T. (1990) Bioactive polyacetylenes from stony corals. Chemistry Letters, 1, 145-148.
185. Zagalsky PF, Herring PJ. (1977) Studies on the blue astaxanthin-proteins of Velella velella (Coelenterata: Chondrophora). Philosophical Transactions of the Royal Society of London, Series B: Biological Sciences, 279, 289-326.
186. (a)Lindberg DR, Matzen BL. (2004) Anna Meyer and the distinction between grades and clades in early models of gastropod evolution. Invertebrate Biology, 123, 212-217
187. (b) Roopnarine PD. (1999) Systematics, biogeography and extinction of Chionine bivalves (Bivalvia: Veneridae) in tropical America: Early Oligocene-recent. Malacologia, 38, 103-142.
188. Aneiros A, Garateix A. (2004) Bioactive peptides from marine sources: pharmacological properties and isolation procedures. Journal of Chromatography B, 803, 41-53
189. (b) Dembitsky VM, Levitsky DO. (2004) Arsenolipids. Progress in Lipid Research, 43, 403-448
190. Avila C. (1995) Natural products of opisthobranch molluscs: A biological review. Oceanography and Marine Biology, 33, 487-559.
191. Cimino G, Crispino A, Di Marzo V, Gavagnin M, Ros JD. (1990) Oxytoxins, bioactive molecules produced by the marine opisthobranch mollusk Oxynoe olivacea from a diet-derived precursor. Experientia, 46, 767-770
192. (b) Targett NM, McConnell OJ. (1982) Detection of secondary metabolites in marine macroalgae using the marsh periwinkle, Littorina irrorata Say, as an indicator organism. Journal of Chemical Ecology, 8, 115-124.
193. Walker RP, Faulkner DJ. (1981) Chlorinated acetylenes from the nudibranch Diaulula sandiegensis. Journal of Organic Chemistry, 46, 1475-1478
194. (b) Cimino G, De Stefano S, De Rosa S, Sodano G, Villani G. (1980) Novel metabolites from some predator-prey pairs. Bulletin des Societes Chimiques Belges, 89, 1069-1073.
195. Strain HH. (1949) Hopkinsiaxanthin , a xanthophyll of the sea slug. Biological Bulletin (Woods Hole), 97, 206-209
196. (b) McBeth JW. (1972) Carotenoids from nudibranchs. II. Partial characterization of hopkinsiaxanthin. Comparative Biochemistry and Physiology, 41B, 69-77
197. McBeth JW. (1972) Carotenoids from nudibranchs. Comparative Biochemistry and Physiology, 41B, 55-68.
198. Fujiwara Y, Maoka T, Ookubo M, Matsuno T. (1992) Crassostreaxanthins A and B, novel marine carotenoids from the oyster Crassostrea gigas. Tetrahedron Letters, 33, 4941-4944
199. (b) Maoka T. (1997) A new apocarotenoid from the marine shellfish Mytilus coruscus. Journal of Natural Products, 60, 616-617.
200. Maoka T, Fujiwara Y, Hashimoto K, Akimoto N. (2005) Carotenoids in three species of Corbicula clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese freshwater Corbicula clam). Journal of Agricultural and Food Chemistry, 53, 8357-8364.
201. Ha B-S, Baek S-H, Kim S-Y. (2000) Carotenoids components of tunicata, shellfishes and its inhibitory effects on mutagenicity and growth of tumor cell. Han'guk Sikp'um Yongyang Kwahak Hoechi, 29, 922-934.
202. Partali V, Tangen K, Liaaen-Jensen S. (1989) Carotenoids in food chain studies. III. Resorption and metabolic transformation of carotenoids in Mytilus edulis (edible mussel). Comparative Biochemistry and Physiology, 92B, 239-246
203. (b) Hertzberg S, Partali V, Liaaen-Jensen S. (1988) Animal carotenoids. 32. Carotenoids of Mytilus edulis (edible mussel). Acta Chemica Scandinavica, 42B, 495-503.
204. Nishino H, Satomi Y, Tokuda H, Hishino A, Iwashima A, Tanaka Y, Yamano Y, Shibata Y, Torihara M, Tamai Y, Ito M. (1991) Anti-tumor activity of peridinin and its structurally related butenolide compounds. Journal of Kyoto Prefectural University of Medicine, 100, 831-835
205. (b) Nishino H. (1998) Cancer prevention by carotenoids. Mutation Research, 402, 159-163
206. Matsuno T, Maoka T, Hiraoka K. (1981) A new acetylenic carotenoid from sea mussels. Nippon Suisan Gakkaishi, 47, 143.
207. Campbell SA, Mallams AK, Waight ES, Weedon BCL, Barbier M, Lederer E, Salaque A. (1967) Pectenoxanthin, cynthiaxanthin and a new acetylenic carotenoid, pectinolone. Chemical Communications, 941-942
208. (b) Matsuno T, Hiraoka K, Maoka T. (1981) Carotenoid in the gonad of scallop. Nippon Suisan Gaku, 47, 383-390.
209. Maoka T, Matsuno M. (1988) Isolation and structural elucidation of three new acetylenic carotenoids from the Japanese sea mussel Mytilus coruscus. Nippon Suisan Gaku, 54, 1443-1447
210. (b) Fujiwara Y, Maoka T, Ookubo M, Matuno T. (1992) Crassostreaxanthin A and B, novel marine carotenoids from the oyster Crassostrea gigas. Tetrahedron Letters, 33, 4941-4944.
211. Tsushima M, Maoka T, Matuno T. (2001) Structure of carotenoids with 5, 6-dihydro-â-end groups from the spindle shell Fushinus perplexus. Journal of Natural Products, 64, 1139-1142
212. (b) Vershinin A. (1996) Carotenoids in Mollusca: approaching the functions. Comparative Biochemistry and Physiology, 113B, 63-71.
213. Maoka T, Fujiwara Y, Hashimoto K, Akimoto N. (2005) Structure of new carotenoids from Corbicula clam Corbicula japonica. Journal of Natural Products, 68, 1341-1344
214. Ballard CE, Yu H, Wang B. (2002) Recent developments in depsipeptide research. Current Medicinal Chemistry, 9, 471-498
215. (b) Rodriguez J, Fernandez R, Quinoa E, Riguera R, Debitus C, Bouchet P. (1994) Onchidin: a cytotoxic depsipeptide with C2 symmetry from a marine mollusk. Tetrahedron Letters, 35, 9239-9242
216. Fernandez R, Rodriguez, J, Quiñoa E, Riguera R, Muñoz L, Fernandez-Suarez M, Debitus C. (1996) Onchidin B. A new cyclodepsipeptide from the marine mollusc Onchidium sp. Journal of the American Chemical Society, 118, 11635-11643.
217. Reese MT, Gulavita NK, Nakao Y, Hamann MT, Yoshida WY, Coval SJ, Scheuer PJ. (1996) Kulolide: a cytotoxic depsipeptide from a cephalaspidean mollusk, Philinopsis speciosa. Journal of the American Chemical Society, 118, 11081-11084
218. (b) Nakao Y, Yoshida WY, Szabo CM, Baker BJ, Scheuer PJ. (1998) More peptides and other diverse constituents of the marine mollusk Philinopsis speciosa. Journal of Organic Chemistry, 63, 3272-3280.
219. Pettit GR, Xu J-P, Hogan F, Cerny RL. (1998) Antineoplastic agents. 369. Isolation and structure of dolastatin 17. Heterocycles, 47, 491-496
220. (b) Pettit GR, Xu J-P. (1998) Isolation and structural elucidation of the cytostatic linear and cyclo-depsipeptides dolastatin 16, dolastatin 17, and dolastatin 18. PCT Int. Appl. 57 pp. WO 9836765 A1 19980827, Application: WO 98-US3455 19980223.
221. Kelly MS. (2005) Echinoderms: their culture and bioactive compounds. Progress in Molecular and Subcellular Biology, 39, 139-165
222. (b) Miyamoto T. (2005) Pharmaceutical and bioactive materials from echinoderms. Kaiyo Seibutsu Seibun no Riyo, 145-158
223. Smiley S. (1990) A review of echinoderm oogenesis. Journal of Electron Microscopy Technique, 16, 93-114.
224. Yokota Y. (2005) Bioresources from echinoderms. Progress in Molecular and Subcellular Biology, 39, 251-266
225. (b) Parisi G, Pierantoni R. (1977) Carotenoids in Cryptomonas species. I. Bollettino - Societa Italiana di Biologia Sperimentale, 53, 575-81
226. Czeczuga B. (1984) Investigations of carotenoids in some animals of the Adriatic Sea - VI. Representatives of sponges, annelids, mollusks and echinodermates. Comparative Biochemistry and Physiology, 78B, 259-264.
227. Gross J, Carmon M, Lifshitz A, Sklarz B. (1975) Carotenoids of the invertebrates of the Red Sea (Eilat shore). Carotenoids of the crinoid Lamprometra klunzingeri (Echinodermata). Comparative Biochemistry and Physiology, 52B, 459-564.
228. Czeczuga B. (1977) Investigations of carotenoids in some animals of the Adriatic Sea. V. Echinodermata. Hydrobiologia, 54, 177-180.
229. Tsushima M, Byrne M, Amemiya S, Matsuno T. (1995) Comparative biochemical studies of carotenoids in sea urchins- III. Relationship between developmental mode and carotenoids in the Australian echinoids Heliocidaris erythrogramma and H. tuberculata and a comparison with Japanese species. Comparative Biochemistry and Physiology, 110B, 719-723
230. (b) Tsushima M, Kawakami T, Matsuno T. (1993) Metabolism of carotenoids in sea - urchin Pseudocentrotus depressus. Comparative Biochemistry and Physiology, 106B, 737-41.
231. Tsushima M, Matsuno T. (1990) Comparative biochemical studies of carotenoids in sea - urchins - I. Comparative Biochemistry and Physiology, 96B, 801-810
232. (b) Tsushima M, Amemiya S, Matsuno T. (1993) Comparative biochemical studies of carotenoids in sea - urchins -II. The more primitive sea - urchins belonging to the orders Cidaroida, Echinothurioida, Diadematoida and Arabacioida. Comparative Biochemistry and Physiology, 106B, 729-735.
233. Francis GW, Upadhyay RR, Liaaen Jensen S. (1970) Animal carotenoids. 4. Carotenoids of Asterias rubens. Asterinic acid. Acta Chemica Scandinavica, 24, 3050-3052
234. (b) Bernhard K, Englert G, Meister W, Vecchi M, Renstroem B, Liaaen-Jensen S. (1982) Carotenoids of the carotenoprotein asteriarubin. Optical purity of asterinic acid. Helvetica Chimica Acta, 65, 2224-2229.
235. Shone CC, Britton G, Goodwin TW. (1979) The violet carotenoprotein of the starfish, Asterias rubens. Comparative Biochemistry and Physiology, 62B, 507-513
236. (b) Tanaka Y. (1978) Comparative biochemical studies on carotenoids in aquatic animals. Kagoshima Daigaku Suisangakubu Kiyo, 27, 355-422.
237. Tanaka Y, Katayama T. (1976) Biochemical studies on carotenoids in Echinodermata. The structure of an astaxanthin-like pigment (7, 8-didehydroastaxanthin) and the carotenoids in starfish. Nippon Suisan Gakkaishi, 42, 807-812
238. (b) De Nicola MG. (1959) Composition of new keto carotenoids related to the metabolism of astaxanthin in starfish. Bollettino delle Sedute della Accademia Gioenia di Scienze Naturali in Catania, 5, 201-214.
239. Fontaine AR. (1962) Pigments in Ophiocomina nigra. III. Carotenoid pigments. Journal of the Marine Biological Association U.K. 42, 33-47
240. (b) Maoka T, Tsushima M, Matsuno T. (1989) New acetylenic carotenoids from the starfishes Asterina pectinifera and Asterias amurensis. Comparative Biochemistry and Physiology, 93B, 829-834.
241. Matsuno T, Tsushima M. (1995) Comparative biochemical studies of carotenoids in sea cucumbers. Comparative Biochemistry and Physiology, 111B, 597-605
242. (b) Euler H, Hellstrom H. (1934) Asteric acid, a carotenoid acid from starfish. Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 223, 89-97.
243. Elgsaeter A, Tauber Jd, Liaaenjensen S. (1978) Animal carotenoids .15. Carotenoid distribution and carotenoprotein of Asterias rubens. Biochimica et Biophysica Acta, 530, 402-411
244. (b) Francis Gw, Upadhyay Rr, Liaaenje.S. (1970) Animal carotenoids .4. Carotenoids of asterias-rubens - Asterinsaure. Acta Chemica Scandinavica, 24, 3050-3055.
245. Howell KL, Billett DSM, Tyler PA. (2004) Feeding ecology of deep-sea seastars (Echinodermata: Asteroidea): a pigment biomarker approach. Marine Ecology-Progress Series, 266, 103-110
246. (b) Goodwin TW. (1969) Pigments in echinodermata. Chemical Zoology, 3, 135-147
247. Vevers HG. (1966) Pigmentation. Physiology of Echinodermata, 4, 267-275.
248. Kobayashi J, Ishibashi M. (2000) Bioactive secondary metabolites from Okinawan sponges and tunicates. Studies in Natural Products Chemistry, 23D, 185-231.
249. Fujita M, Nakao Y, Matsunaga S, van Soest RW, Itoh Y, Seiki M, Fusetani N. (2003) Callysponginol sulfate A, an MT1-MMP inhibitor isolated from the marine sponge Callyspongia truncata. Journal fo Natural Products, 66, 569-571
250. (b) Fujita M, Nakao Y, Matsunaga S, Nishikawa T, Fusetani N. (2002) Sodium 1-(12-hydroxy)octadecanyl sulfate, an MMP2 inhibitor, isolated from a tunicate of the family Polyclinidae. Journal of Natural Products, 65, 1936-1938.
251. Gavagnin M, Castelluccio F, Antonelli A, Templado J, Cimino G. (2004) Unusual C21 linear polyacetylenic alcohols from an Atlantic ascidian. Lipids, 39, 681-685.
252. Matsuno T, Ookubo M, Nishizawa T, Shimizu I. (1984) Carotenoids of sea squirts. I. New marine carotenoids, halocynthiaxanthin and mytiloxanthinone from Halocynthia roretzi. Chemical & Pharmaceutical Bulletin, 32, 4309-4315
253. (b) Choi B-D, Kang S-J, Choi Y-J, Youm M-G, Lee K-H. (1994) Utilization of ascidian (Halocynthia roretzi) tunic. 3. Carotenoid compositions of ascidian tunic. Han'guk Susan Hakhoechi, 27, 344-350.
254. Matsuno T, Nishino H. (1992) Anticancer agents containing halocynthiaxanthin. Japan Kokai Tokkyo Koho, 5 pp. Japanese Patent: JP 04120019 A2 19920421 Heisei
255. (b) Nishino H, Tsushima M, Matsuno T, Tanaka Y, Okuzumi J, Murakoshi M, Satomi Y, Takayasu J, Tokuda H, Anti-neoplastic effect of halocynthiaxanthin , a metabolite of fucoxanthin. Anti-Cancer Drugs, 3, 493-497.
256. McDonald LA, Capson TL, Krishnamurthy G, Ding W-D, Ellestad GA, Bernan VS, Maiese WM, Lassota P, Discafani C. (1996) Namenamicin, a new enediyne antitumor antibiotic from the marine ascidian Polysyncraton lithostrotum. Journal of the American Chemical Society, 118, 10898-10899.
257. Castillo R, Negre-Sadargues G, Lenel R. (1982) General survey of the carotenoids in Crustacea. (Eds): Britton G, Goodwin TW. (1982) Carotenoid Chemistry and Biochemistry, Proceedings of International Symposium on Carotenoids, 6th Meeting, Date 1981, 211-224. Publisher: Pergamon, Oxford, UK
258. (b) Lenel R, Castillo R, Negre-Sadargues G. (1983) Carotenoid pigments. The importance of their role in the physiology of Crustacea. Oceanis, 9, 61-72.
259. Linan-Cabello MA, Paniagua-Michel J, Hopkins PM. (2002) Bioactive roles of carotenoids and retinoids in crustaceans. Aquaculture Nutrition, 8, 299-309
260. (b) Fraser PD, Bramley PM. (2004) The biosynthesis and nutritional uses of carotenoids. Progress in Lipid Research, 43, 228-265
261. Ghidalia W. (1985) Structural and biological aspects of pigments in crustaceans. Bliss DE, Mantel LH. Eds, Biology of Crustacea, 9, 301-394. Publisher: Academic, Orlando, Fla.
262. Lederer E. (1938) Carotenoids of invertebrates. Bulletin de la Societe de Chimie Biologique, 20, 567-610
263. (b) Gilchrist BM, Lee WL. (1972) Carotenoid pigments and their possible role in reproduction in the sand crab, Emerita analoga. Comparative Biochemistry and Physiology, 42B, 263-294.
264. Matsuno T, Watanabe T, Nagata S. (1974) Carotenoid pigments of crustacea. II. Carotenoid pigments of Scyllarides squamosus (=Scyllarus sieboldi) and Parribacus antarcticus (= Parribacus ursus-major). Nippon Suisan Gakkaishi, 40, 619-624
265. (b) Matsuno T, Maoka T. (1988) Carotenoids of crustacea - VI. The carotenoids of crab Paralithodes brevipes (Hanasakigani in Japanese). Nippon Suisan Gakkaishi, 54, 1437-1442.
266. Czeczuga B. (1977) Occurrence of carotenoids in certain crustaceans of the Black Sea. Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Biologiques, 25, 511-514.
267. Mente E. (2003) Nutrition, Physiology, and Metabolism in Crustaceans. 140 pp. Publisher: Science, Enfield, NH, USA
268. (b) Dixon DR, Pruski AM, Dixon LR, Jr, Awadhesh N. (2002) Marine invertebrate eco-genotoxicology: A methodological overview. Mutagenesis, 17, 495-507.
269. Bhakuni DS. (1994) Bioactive metabolites of the marine invertebrates-mollusks, echinoderms, tunicates and crustaceans: Part II. Journal of Scientific & Industrial Research, 53, 340-53
270. (b) Ikeda T. (1988) Metabolism and chemical composition of crustaceans from the Antarctic mesopelagic zone. Deep-Sea Research, 35A, 1991-2002.
271. Negre-Sadargues G. (1978) Metabolic transformations of carotenoid pigments in crustaceans: Literature survey. Annee Biologique, 17, 415-454
272. (b) Huggins AK, Munday KA. (1968) Crustacean metabolism. Advances in Comparative Physiology and Biochemistry, 3, 271-378.
273. Vonk HJ. (1960) Digestion and metabolism. Physiology of Crustacea, 1, 291-316
274. (b) Schonborn EG. (1912) The metabolism of crustaceae. Zeitschrift fuer Biologie (Munich), 57, 534-544.
275. Liaaen-Jensen, S. (2004) Basic carotenoid chemistry. Oxidative Stress and Disease, 13, 1-30
276. (b) Matsuno, T. (1992) Carotenoids in fish and their metabolism. Hikaku Seiri Seikagaku, 9, 59-72.
277. Sueki K, Ito Y. (1991) Use of carotenoids in food, drugs, and feed. New Food Industry, 33, 33-40
278. (b) Ito Y, (1988) Role of carotenoids in animals. New Food Industry, 30, 30-35.
279. Goodwin TW. (1986) Metabolism, nutrition, and function of carotenoids. Annual Review of Nutrition, 6, 273-297
280. (b) Crozier GF. (1974) Pigments of fishes. Chemical Zoology, 8, 509-521.
281. Matsuno T, Nagata S, Sato Y, Watanabe T. (1974) Comparative biochemical studies of carotenoids in fishes. II. Carotenoids of horse mackerel, swellfishes, porcupine fishes, and striped mullet Nippon Suisan Gakkaishi, 40, 579-584
282. (b) Matsuno T, Katsuyama M, Iwasaki N. (1975) Comparative biochemical studies of carotenoids in fishes. IV. Carotenoids in six species of Gobioninaeous fishes. Nippon Suisan Gakkaishi, 41, 351-355.
283. Matsuno T, Katsuyama M. (1975) Comparative biochemical studies of carotenoids in fishes. VI. Carotenoids of Japanese sculpins and white gobies. Nippon Suisan Gakkaishi, 41, 675-679
284. (b) Matsuno T, Katsuyama M, Uemura M. (1975) Comparative biochemical studies of carotenoids in fishes. VII. Carotenoids of common ice- fish and sea smelt. Nippon Suisan Gakkaishi, 41, 681-684.
285. Matsuno T, Katsuyama M. (1976) Comparative biochemical studies of carotenoids in fishes. XI. Carotenoids of two species of flying fish, mackerel pike, killifish, three-spined stickleback, and Chinese eight-spined stickleback. Nippon Suisan Gakkaishi, 42, 761-763
286. (b) Matsuno T, Katsuyama M. (1976) Comparative biochemical studies of carotenoids in fish. XIII. Carotenoids in six species of Leuciscinaeous fish. Nippon Suisan Gakkaishi, 42, 847-850.
287. Katsuyama M, Matsuno T. (1979) Isolation and identification of rhodoxanthin from the fish, Tilapia nilotica. Nippon Suisan Gakkaishi, 45, 1045
288. (b) Matsuno T, Katsuyama M. (1979) Comparative biochemical studies of carotenoids in fishes. XIV. Carotenoids of Tilapia. I. Nippon Suisan Gakkaishi, 45, 1533-1538.
289. Matsuno T, Nagata S, Katsuyama M, Matsutaka H, Maoka T, Akita T. (1980) Comparative biochemical studies of carotenoids in fishes. XVIII. Carotenoids of cultured fishes. Japanese char, brook trout, lake trout, Masu trout, red-spotted Masu trout, rainbow trout and brown trout. Nippon Suisan Gakkaishi, 46, 473-478
290. (b) Matsuno T, Katsuyama M. (1979) Comparative biochemical studies of carotenoids in fishes. XV. Carotenoids of piranha, bluegill, flamingo cichlid, red devil and formosan snakehead. Nippon Suisan Gakkaishi, 45, 1539-1541.
291. Fujita T, Satake M, Watanabe T, Kitajima C, Miki W, Yamaguchi K, Konosu S. (1983) Chemistry and utilization of plankton. IV. Pigmentation of cultured red sea bream with astaxanthin diester purified from krill oil. Nippon Suisan Gakkaishi, 49, 1855-1861.
292. Matsuno T, Katsuyama M, Maoka T, Hirono T, Komori T. (1985) Reductive metabolic pathways of carotenoids in fish (3S, 3'S)- astaxanthin to tunaxanthin A, B and C. Comparative Biochemistry and Physiology, 80B, 779-789.
293. Matsuno T, Maoka T, Ikuno Y. (1986) Comparative biochemical studies of carotenoids in fish. XXVII. Carotenoids in the eggs of three species of Cyprinidae. Comparative Biochemistry and Physiology, 83B, 335-337.
294. Matsuno T, Katsuyama M, Ikuno Y, Yamashita E, Ha BS. (1990) Comparative biochemical studies of carotenoids in fish XXXIV. The occurrence of eight stereoisomers of tunaxanthin from the freshwater fish Siniperca scherzeri. Nippon Suisan Gakkaishi, 56, 651-654.
295. Ando S, Osada K, Saneyoshi M. (1991) Characteristics of carotenoid features in muscle and ovary from anadromous and river resident types of Alaskan dolly varden charr (Salvelinus malma malma). Comparative Biochemistry and Physiology, 100B, 63-65.
296. Lee H-H, Park M-Y, Kweon M-J, Baek S-H, Kim S-Y, Kang D-S, Ha B-S. (1996) Comparison of carotenoid pigments in mandarin fish, Siniperca scherzeri, and Korean perch, Coreoperca herzi, in the family Serranidae. Han'guk Yongyang Siklyong Hakhoechi (Korea), 25, 87-93.
297. Yamashita E, Maruyama Y, Katsuyama M, Tsushima M, Arai S, Matsuno T. (1998) The presence and origin of an apocarotenoid, Galloxanthin in ayu Plecoglossus altivelis. Fisheries Science, 64, 826-830.
298. Kim HS, Kim Y, Cho SH, Jo J-Y. (1999) Effects of dietary carotenoids on the nuptial color of the bitterling (Rhodeus uyekii). Han'guk Susan Hakhoechi, 32, 276-279.
299. Kim H-Y, Baek S-H, Kim S-Y, Geong K-I, Kweon M-J, Kim J-H, Ha B-S. (1999) Metabolism of dietary carotenoids and effects to improve the body color of oily bittering, Acheilognathus koreensis. Han'guk Sikp'um Yongyang Kwahak Hoechi, 28, 1099-1106.
300. Tsushima M, Mune E, Maoka T, Matsuno T. (2000) Isolation of stereoisomeric epoxy carotenoids and new acetylenic carotenoid from the common freshwater goby Rhinogobius brunneus. Journal of Natural Produ ucts, 63, 960-964.