Epoxycarotenoids and cancer. Review

Current Bioactive Compounds

Volumn 8, Issue 2, 2012, Pages 109-141

  Gagez, Anne Laure ^a   Thiéry, Valérie ^a   Pasquet, Virginie ^a   Cadoret, Jean Paul ^b   Picot, Laurent ^a  

^a UNIVERSITÉ DE LA ROCHELLE   (France)

^b IFREMER   (France)

Author keywords

Cancer; Carotenoid; Epoxycarotenoid; Epoxyxanthophyll; MDR; Pigment

Indexed keywords

ANTINEOPLASTIC AGENT; CAPSANTHIN 3,6 EPOXIDE; CAPSOCHROME; CAROTENOID; CRASSOSTREAXANTHIN A; CUCURBITAXANTHIN A; CUCURBITAXANTHIN A 3' ESTER; DIADINOCHROME A; DIADINOCHROME B; DINOCHROME A; DINOCHROME B; EPOXY BETA CAROTENE; EPOXYCAROTENOID; FOLIACHROME; FOLIAXANTHIN; FUCOXANTHIN; HALOCYNTHIAXANTHIN; LUTEIN 5,8 EPOXIDE; MONOEPOXY ALPHA CAROTENE; NEOCHROME; NEOXANTHIN; PERIDININ; PERIDININ 5,8 FURANOXIDE; PYRRHOXANTHIN; SULCATOXANTHIN; TROLLIXANTHIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIOLAXANTHIN; VIOLEOXANTHIN; ZEAXANTHIN 5,6 EPOXIDE;

ABELSON MURINE LEUKEMIA ONCOVIRUS; ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; BLADDER CANCER; BRAIN CANCER; BREAST CANCER; BURKITT LYMPHOMA; CANCER CELL; CELL STRAIN CACO 2; CELL STRAIN HCT116; CELL STRAIN HEPG2; CELL STRAIN HL 60; CELL STRAIN LNCAP; CELL STRAIN MCF 7; CHRONIC MYELOID LEUKEMIA; COLON CANCER; DRUG METABOLISM; DRUG STRUCTURE; HELA CELL; HUMAN; HUMAN T CELL LEUKEMIA VIRUS INFECTION; IN VITRO STUDY; INTESTINE ABSORPTION; KIDNEY CANCER; LEUKEMIA; LIVER CANCER; LUNG CANCER; LYMPHOMA; MELANOMA; NEOPLASM; NEUROBLASTOMA CELL; NONHUMAN; OSTEOSARCOMA CELL; OVARY CANCER; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIMARY EFFUSION LYMPHOMA; PRIORITY JOURNAL; PROSTATE CANCER; REVIEW; STOMACH ADENOCARCINOMA; STOMACH CANCER; T CELL LEUKEMIA; UMBILICAL VEIN ENDOTHELIAL CELL; UTERINE CERVIX CANCER; UTERUS CANCER;

EID: 84863952717     PISSN: 15734072     EISSN: 18756646     Source Type: Journal    
DOI: 10.2174/157340712801784787     Document Type: Review

References (142)

1. Etoh, H.; Utsunomiya, Y.; Komori, A.; Murakami, Y.; Oshima, S.; Inakuma, T. Carotenoids in human blood plasma after ingesting paprika juice. Biosci., Biotechnol., Biochem., 2000, 64, 1096-1098.
2. Asai, A.; Terasaki, M.; Nagao, A. An epoxide-furanoid rearrangement of spinach neoxanthin occurs in the gastrointestinal tract of mice and in vitro: formation and cytostatic. Nutr. Cancer, 2004, 2237-2243.
3. Sugawara, T.; Baskaran, V.; Tsuzuki, W.; Nagao, A. Brown algae fucoxanthin is hydrolyzed to fucoxanthinol during absorption by Caco-2 human intestinal cells and mice. J. Nutr., 2002, 132, 946-951.
4. Sangeetha, R.K.; Bhaskar, N.; Divakar, S.; Baskaran, V. Bioavailability and metabolism of fucoxanthin in rats: structural characterization of metabolites by LC-MS (APCI). Mol. Cell. Biochem., 2010, 333, 299-310.
5. Barua, A.B.; Olson, J.A. Xanthophyll epoxides, unlike betacarotene monoepoxides, are not detectibly absorbed by humans. J. Nutr., 2001, 131, 3212-3215.
6. Khachik, F.; Spangler, C.J.; Smith, J.C.J.; Canfield, L. M.; Steck, A.; Pfander, H. Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal. Chem., 1997, 69, 1873-1881.
7. Perez-Galvez, A.; Martin, H.D.; Sies, H.; Stahl, W. Incorporation of carotenoids from paprika oleoresin into human chylomicrons. Br. J. Nutr., 2003, 89, 787-793.
8. Czeczuga-Semeniuk, E.; Woczyski, S. Dietary carotenoids in normal and pathological tissues of corpus uteri. Folia Histochem. Cytobiol., 2008, 46, 283-290.
9. Maoka, T.; Mochida, K.; Kozuka, M.; Ito, Y.; Fujiwara, Y.; Hashimoto, K.; Enjo, F.; Ogata, M.; Nobukuni, Y.; Tokuda, H.; Nishino, H. Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L. Cancer Lett., 2001, 172, 103-109.
10. Murakami, A.; Nakashima, M.; Koshiba, T.; Maoka, T.; Nishino, H.; Yano, M.; Sumida, T.; Kim, O.K.; Koshimizu, K.; Ohigashi, H. Modifying effects of carotenoids on superoxide and nitric oxide generation from stimulated leukocytes. Cancer Lett., 2000, 149, 115-123.
11. Maoka, T.; Akimoto, N.; Murakoshi, M.; Sugiyama, K.; Nishino, H. Carotenoids in clams, Ruditapes philippinarum and Meretrix petechialis. J. Agric. Food Chem., 2010, 58, 5784-5788.
12. Matsuno, T.; Tani, Y.; Maoka, T.; Matsuo, K.; Komori, T. Isolation and structural elucidation of cucurbitaxanthin A and B from pumpkin Cucurbita maxima. Phytochemistry, 1986, 25, 2837-2840.
13. Deli, J.; Molnár, P.; Matus, Z.; Tóth, G. Carotenoid composition in the fruits of red paprika (Capsicum annuum var. lycopersiciforme rubrum) during ripening; biosynthesis of carotenoids in red paprika. J. Agric. Food Chem., 2001, 49, 1517-1523.
14. Goss, R.; Jakob, T. Regulation and function of xanthophyll cycledependent photoprotection in algae. Photosyn. Res., 2010, 106, 103-122.
15. Cha, K.H.; Koo, S.Y.; Lee, D.U. Antiproliferative effects of carotenoids extracted from Chlorella ellipsoidea and Chlorella vulgaris on human colon cancer cells. J. Agric. Food Chem., 2008, 56, 10521-10526.
16. Alberte, R.S.; Andersen, R.A. Antheraxanthin, a light harvesting carotenoid found in a chromophyte alga. Plant Physiol., 1986, 80, 583-587.
17. Czeczuga, B.; Cifuentest, B.; Reynaud, R.A. Carotenoids in Lichens from the Canary Islands. Systematics, 1988, 16, 117-118.
18. Czeczuga, B.; Kantvilas, G. Carotenoids in Lichens From Tasmanian Forests. Aust. J. Bot., 1990, 38, 517.
19. Molnár, J.; Gyémánt, N.; Mucsi, I.; Molnár, A.; Szabó, M.; Körtvélyesi, T.; Varga, A.; Molnár, P.; Tóth, G. Modulation of multidrug resistance and apoptosis of cancer cells by selected carotenoids. In Vivo, 2004, 18, 237-244.
20. Ugocsai, K.; Varga, A.; Molnár, P.; Antus, S.; Molnár, J. Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP. In Vivo, 2005 19, 433-438.
21. Molnár, J.; Gyémánt, N.; Tanaka, M.; Hohmann, J.; Bergmann-Leitner, E.; Molnár, P.; Deli, J.; Didiziapetris, R.; Ferreira, M.J.U. Inhibition of multidrug resistance of cancer cells by natural diterpenes, triterpenes and carotenoids. Curr. Pharm. Des., 2006, 12, 287-311.
22. Molnar, J.; Engi, H.; Hohmann, J.; Molnar, P.; Deli, J.; Wesolowska, O.; Michalak, K.; Wang, Q. Reversal of multidrug resitance by natural substances from plants. Curr. Top. Med. Chem., 2010, 10, 1757-1768.
23. Mummery, R.; Valadon, L.G.R.; Rothschild, M. Carotenoids in the larvae and food plant of Manduca sexta and in the green and blue larval forms of Hyalophora cecropia. Physiol. Entomol., 1976, 1, 51-54.
24. Deli, J.; Erzsébet,. Carotenoid 5,6-, 5,8-and 3,6-epoxides.; Arkivoc vii, ARKAT USA Inc, 2004; pp. 150-168.
25. Gyémánt, N.; Tanaka, M.; Molnár, P.; Deli, J.; Mándoky, L.; Molnár, J. Reversal of multidrug resistance of cancer cells in vitro: modification of drug resistance by selected carotenoids. Anticancer Res., 2006, 26, 367-374.
26. Duitsman, P.K.; Barua, A.B.; Becker, B.; Olson, J.A. Effects of epoxycarotenoids, beta-carotene, and retinoic acid on the differenciation and viability of the leukemia cell line NB4 in vitro. Int. J. Vitamin Nutr. Res., 1999, 69, 303-308.
27. Crupi, P.; Milella, R.A.; Antonacci, D. Simultaneous HPLC-DADMS (ESI+) determination of structural and geometrical isomers of carotenoids in mature grapes. J. Mass Spectr., 2010, 45, 971-980.
28. Deli, J.; Matus, Z.; Tóth, G. Carotenoid composition in the fruits of Asparagus officinalis. J. Agric. Food Chem., 2000, 48, 2793-6.
29. Britton, G.; Liaaen-Jensen, S.; Pfander, H. Carotenoids Handbook, Birkhauser Verlag: Basel, 2004.
30. Hertzberg, S.; Liaaen Jensen, S. Bacterial carotenoids XX. The carotenoids of Mycobacterium phlei strain Vera. 2. The structures of the phlei-xanthophylls--two novel tertiary glucosides. Acta Chem. Scand., 1967, 21, 15-41.
31. Francis, G.W.; Strand, L.P.; Lien, T.; Knutsen, G. Variations in the carotenoid content of Chlamydomonas reinhardii throughout the cell cycle. Arch. Microbiol., 1975, 104, 249-254.
32. Czeczuga, B. Investigations on carotenoids in amphibia-II. Carotenoids occurring in various parts of the body of certain species. Comp. Bioch. Physiol. Part B: Biochem. Mol. Biol., 1980, 65, 623-630.
33. Roussel, M.J.; Lanotte, M. Maturation sensitive and resistant t(15;17) NB4 cell lines as tools for APL physiopathology: nomenclature of cells and repertory of their known genetic alterations and phenotypes. Oncogene, 2001, 20, 7287-7291.
34. Saha, M.; Rempt, M.; Grosser, K.; Pohnert, G.; Weinberger, F. Surface-associated fucoxanthin mediates settlement of bacterial epiphytes on the rockweed Fucus vesiculosus. Biofouling, 2011, 27, 423-433.
35. Beutler, M.; Wiltshire, K.H.; Meyer, B.; Moldaenke, C.; Lüring, C.; Meyerhöfer, M.; Hansen, U.P.; Dau, H. A fluorometric method for the differentiation of algal populations in vivo and in situ. Photosyn. Res., 2002, 72, 39-53.
36. LaRoche, J.; Henry, D.; Wyman, K.; Sukenik, A.; Falkowski, P. Cloning and nucleotide sequence of a cDNA encoding a major fucoxanthin-, chlorophyll a/c-containing protein from the chrysophyte Isochrysis galbana: implications for evolution of the cab gene family. Plant Mol. Biol., 1994, 25, 355-368.
37. Kim, S.M.; Shang, Y.F.; Um, B.H. A preparative method for isolation of fucoxanthin from Eisenia bicyclis by centrifugal partition chromatography. Phytochem. Anal, 2011, 22, 322-329.
38. Maeda, H.; Hosokawa, M.; Sashima, T.; Funayama, K.; Miyashita, K. Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tissues. Biochem. Biophys. Res. Commun., 2005, 332, 392-397.
39. Yan, X.; Chuda, Y.; Suzuki, M.; Nagata, T. Fucoxanthin as the major antioxidant in Hijikia fusiformis, a common edible seaweed. Biosci., Biotechnol., Biochem., 1999, 63, 605-607.
40. Maoka, T. Recent progress in structural studies of carotenoids in animals and plants. Arch. Biochem. Biophys., 2009, 483, 191-195.
41. Maoka, T. Carotenoids in marine animals. Marine Drugs, 2011, 9, 278-293.
42. Nishino, H.; Tsushima, M.; Matsuno, T.; Tanaka, Y.; Okuzumi, J.; Murakoshi, M.; Satomi, Y.; Takayasu, J.; Tokuda, H.; Nishino, A. Anti-neoplastic effect of halocynthiaxanthin, a metabolite of fucoxanthin. Anticancer Drugs, 1992, 3, 493-497.
43. Okuzumi, J.; Nishino, H.; Murakoshi, M.; Iwashima, A.; Tanaka, Y.; Yamane, T.; Fujita, Y.; Takahashi, T. Inhibitory effects of fucoxanthin, a natural carotenoid, on N-myc expression and cell cycle progression in human malignant tumor cells. Cancer Lett.,1990, 55, 75-81.
44. Yamamoto, K.; Ishikawa, C.; Katano, H.; Yasumoto, T.; Mori, N. Fucoxanthin and its deacetylated product, fucoxanthinol, induce apoptosis of primary effusion lymphomas. Cancer Lett., 2011, 300, 225-234.
45. Ishikawa, C.; Tafuku, S.; Kadekaru, T.; Sawada, S.; Tomita, M.; Okudaira, T.; Nakazato, T.; Toda, T.; Uchihara, J.N.; Taira, N.; Ohshiro, K.; Yasumoto, T.; Ohta, T.; Mori, N. Anti-adult T-cell leukemia effects of brown algae fucoxanthin and its deacetylated product, fucoxanthinol. Int. J. Cancer, 2008, 123, 2702-2712.
46. Yu, R.X.; Hu, X.M.; Xu, S.Q.; Jiang, Z.J.; Yang, W. Effects of fucoxanthin on proliferation and apoptosis in human gastric adenocarcinoma MGC-803 cells via JAK/STAT signal pathway. Eur. J. Pharmacol., 2011, 657, 10-19.
47. Konishi, I.; Hosokawa, M.; Sashima, T.; Kobayashi, H.; Miyashita, K. Halocynthiaxanthin and fucoxanthinol isolated from Halocynthia roretzi induce apoptosis in human leukemia, breast and colon cancer cells. Comp. Biochem. Physiol. Toxicol. Pharmacol., 2006, 142, 53-59.
48. Moreau, D.; Tomasoni, C.; Jacquot, C.; Kaas, R.; Le Guedes, R.; Cadoret, J.P.; Muller-Feuga, A.; Kontiza, I.; Vagias, C.; Roussis, V.; Roussakis, C. Cultivated microalgae and the carotenoid fucoxanthin from Odontella aurita as potent anti-proliferative agents in bronchopulmonary and epithelial cell lines. Environ. Toxicol. Pharmacol., 2006, 22, 97-103.
49. Kotake-Nara, E.; Asai, A.; Nagao, A. Neoxanthin and fucoxanthin induce apoptosis in PC-3 human prostate cancer cells. Cancer Lett., 2005, 220, 75-84.
50. Kotake-Nara, E.; Kushiro, M.; Zhang, H.; Sugawara, T.; Miyashita, K.; Nagao, A. Carotenoids affect proliferation of human prostate cancer cells. J. Nutr., 2001, 131, 3303-3306.
51. Satomi, Y.; Nishino, H. Implication of mitogen-activated protein kinase in the induction of G1 cell cycle arrest and gadd45 expression by the carotenoid fucoxanthin in human cancer cells. Biochim. Biophys. Acta, 2009, 1790, 260-266.
52. Satomi Y. Fucoxanthin induces GADD45A expression and G1 arrest with SAPK/JNK activation in LNCap human prostate cancer cells. Anticancer Res., 2012, 32 (3), 807-813.
53. Hosokawa, M.; Kudo, M.; Maeda, H.; Kohno, H.; Tanaka, T.; Miyashita, K. Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPARgamma ligand, troglitazone, on colon cancer cells. Biochim. Biophys. Acta, 2004, 1675, 113-119.
54. Das, S.K.; Hashimoto, T.; Shimizu, K.; Yoshida, T.; Sakai, T.; Sowa, Y.; Komoto, A.; Kanazawa, K. Fucoxanthin induces cell cycle arrest at G0/G1 phase in human colon carcinoma cells through up-regulation of p21WAF1/Cip1. Biochim. Biophys. Acta, 2005, 1726, 328-935.
55. Das, S.K.; Hashimoto, T.; Kanazawa, K. Growth inhibition of human hepatic carcinoma HepG2 cells by fucoxanthin is associated with down-regulation of cyclin D. Biochim. Biophys. Acta, 2008, 1780, 743-749.
56. Liu, C.L.; Huang, Y.S.; Hosokawa, M.; Miyashita, K.; Hu, M.L. Inhibition of proliferation of a hepatoma cell line by fucoxanthin in relation to cell cycle arrest and enhanced gap junctional intercellular communication. Chem.-Biol. Interact., 2009, 182, 165-172.
57. Zhang, Z.; Zhang, P.; Hamada, M.; Takahashi, S.; Xing, G.; Liu, J.; Sugiura, N. Potential chemoprevention effect of dietary fucoxanthin on urinary bladder cancer EJ-1 cell line. Oncol. Rep., 2008, 20, 1099-1103.
58. Ganesan, P.; Noda, K.; Manabe, Y.; Ohkubo, T.; Tanaka, Y.; Maoka, T.; Sugawara, T.; Hirata, T. Siphonaxanthin, a marine carotenoid from green algae, effectively induces apoptosis in human leukemia (HL-60) cells. Biochim. Biophys. Acta, 2011, 1810, 497-503.
59. Okuzumi, J.; Takahashi, T.; Yamane, T.; Kitao, Y.; Inagake, M.; Ohya, K.; Nishino, H.; Tanaka, Y. Inhibitory effects of fucoxanthin, a natural carotenoid, on N-ethyl-N'-nitro-nnitrosoguanidine-induced mouse duodenal carcinogenesis. Cancer Lett., 1993, 68, 159-168.
60. Kim, J.M.; Araki, S.; Kim, D.J.; Park, C.B.; Takasuka, N.; Baba-Toriyama, H.; Ota, T.; Nir, Z.; Khachik, F.; Shimidzu, N.; Tanaka, Y.; Osawa, T.; Uraji, T.; Murakoshi, M.; Nishino, H.; Tsuda, H. Chemopreventive effects of carotenoids and curcumins on mouse colon carcinogenesis after 1,2-dimethylhydrazine initiation. Carcinogenesis, 1998, 19, 81-85.
61. Nishino, H. Cancer prevention by carotenoids. Mutat. Res., 1998, 402, 159-163.
62. Kim, K.N.; Heo, S.J.; Kang, S.M.; Ahn, G.; Jeon, Y.J. Fucoxanthin induces apoptosis in human leukemia HL-60 cells through a ROSmediated Bcl-xL pathway. Toxicol. Vitro, 2010, 24, 1648-1654.
63. Kotake-Nara, E.; Terasaki, M.; Nagao, A. Characterization of apoptosis induced by fucoxanthin in human promyelocytic leukemia cells. Biosci., Biotechnol., Biochem., 2005, 69, 224-227.
64. Murakami, C.; Takemura, M.; Sugiyama, Y.; Kamisuki, S.; Asahara, H.; Kawasaki, M.; Ishidoh, T.; Linn, S.; Yoshida, S.; Sugawara, F.; Yoshida, H.; Sakaguchi, K.; Mizushina, Y. Vitamin A-related compounds, all-trans retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases. Biochim. Biophys. Acta 2002, 1574, 85-92.
65. Heo, S.J.; Jeon, Y.J. Protective effect of fucoxanthin isolated from Sargassum siliquastrum on UV-B induced cell damage. J. Photochem. Photobiol., 2009, 95, 101-107.
66. Shimoda, H.; Tanaka, J.; Shan, S.J.; Maoka, T. Anti-pigmentary activity of fucoxanthin and its influence on skin mRNA expression of melanogenic molecules. J. Pharm. Pharmacol., 2010, 62, 1137-1145.
67. Yoshiko, S.; Hoyoku, N. Fucoxanthin, a natural carotenoid, induces G1 arrest and GADD45 gene expression in human cancer cells. In Vivo, 2007, 21, 305-310.
68. Jee, H.; Nam, K.T.; Kwon, H.J.; Han, S.U.; Kim, D.Y. Altered expression and localization of connexin32 in human and murine gastric carcinogenesis. Digest. Dis. Sci., 2011, 56, 1323-1332.
69. Holder, J.W.; Elmore, E.; Barrett, J.C. Gap junction function and cancer. Cancer Res. 1993, 53, 3475-3485.
70. Zhang, L.X.; Cooney, R.V.; Bertram, J.S. Carotenoids enhance gap junctional communication and inhibit lipid peroxidation in C3H/10T1/2 cells: relationship to their cancer chemopreventive action. Carcinogenesis, 1991, 12, 2109-2114.
71. Hossain, M.Z.; Wilkens, L.R.; Mehta, P.P.; Loewenstein, W.; Bertram, J.S. Enhancement of gap junctional communication by retinoids correlates with their ability to inhibit neoplastic transformation. Carcinogenesis, 1989, 10, 1743-1748.
72. Sugawara, T.; Matsubara, K.; Akagi, R.; Mori, M.; Hirata, T. Antiangiogenic activity of brown algae fucoxanthin and its deacetylated product, fucoxanthinol. J. Agric. Food Chem., 2006, 54, 9805-9810.
73. Yoshida, T.; Maoka, T.; Das, S.K.; Kanazawa, K.; Horinaka, M.; Wakada, M.; Satomi, Y.; Nishino, H.; Sakai, T. Halocynthiaxanthin and peridinin sensitize colon cancer cell lines to tumor necrosis factor-related apoptosis-inducing ligand. Mol. Cancer Res., 2007, 5, 615-625.
74. Sugawara, T.; Yamashita, K.; Sakai, S.; Asai, A.; Nagao, A.; Shiraishi, T.; Imai, I.; Hirata, T. Induction of Apoptosis in DLD-1 Human Colon Cancer Cells by Peridinin Isolated from the Dinoflagellate, Heterocapsa triquetra. Biosci., Biotechnol., Biochem., 2007, 71, 1069-1072.
75. Maoka, T.; Akimoto, N.; Tsushima, M.; Komemushi, S.; Mezaki, T.; Iwase, F.; Takahashi, Y.; Sameshima, N.; Mori, M.; Sakagami, Y. Carotenoids in marine invertebrates living along the Kuroshio Current Coast. Marine Drugs, 2011, 9, 1419-1427.
76. Shaker, K.H.; Müller, M.; Ghani, M.A.; Dahse, H.M.; Seifert, K. Terpenes from the soft corals Litophyton arboreum and Sarcophyton ehrenbergi. Chem. Biodivers., 2010, 7, 2007-2015.
77. Sugawara, T.; Yamashita, K.; Asai, A.; Nagao, A.; Shiraishi, T.; Imai, I.; Hirata, T. Esterification of xanthophylls by human intestinal Caco-2 cells. Arch. Biochem. Biophys., 2009, 483, 205-212.
78. Maoka, T.; Fujiwara, Y.; Hashimoto, K.; Akimoto, N. Carotenoids in three species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam). J. Agric. Food Chem., 2005, 53, 8357-8364.
79. Keskitaloo, J.; Bergguist, G.; Gardestrom, P.; Jansson, S. A Cellular Timetable of Autumn Senescence 1. Society, 2005, 139, 1635-1648.
80. Kao, T.H.; Chen, C.J.; Chen, B.H. Carotenoid composition in Rhinacanthus nasutus (L.) Kurz as determined by HPLC-MS and affected by freeze-drying and hot-air-drying. Analyst, 2011, 136, 3194-3202.
81. Inbaraj, B.S.; Chien, J.T.; Chen, B.H. Improved high performance liquid chromatographic method for determination of carotenoids in the microalga Chlorella pyrenoidosa. J. Chromatogr., 2006, 1102, 193-199.
82. Rodríguez-Meizoso, I.; Jaime, L.; Santoyo, S.; Cifuentes, A.; García-Blairsy Reina, G.; Señoráns, F.J.; Ibáñez, E. Pressurized fluid extraction of bioactive compounds from Phormidium species. J. Agric. Food Chem., 2008, 56, 3517-3523.
83. Terasaki, M.; Asai, A.; Zhang, H.; Nagao, A. A highly polar xanthophyll of 9'-cis-neoxanthin induces apoptosis in HCT116 human colon cancer cells through mitochondrial dysfunction. Mol. Cell. Biochem., 2007, 300, 227-237.
84. Chang, J.M.; Chen, W.C.; Hong, D.; Lin, J.K. The inhibition of DMBA-induced carcinogenesis by neoxanthin in hamster buccal pouch. Nutr. Cancer, 1995, 24, 325-333.
85. Deli, J.; Molnar, P.; Osz, E.; Toth, G. Analysis of carotenoids in the fruits of Asparagus falcatus: isolation of 5,6-diepikarpoxanthin. Chromatographia, 2000, 51, 183-187.
86. Küpper, H.; Seibert, S.; Parameswaran, A. Fast, sensitive, and inexpensive alternative to analytical pigment HPLC: quantification of chlorophylls and carotenoids in crude extracts by fitting with Gauss peak spectra. Anal. Chem., 2007, 79, 7611-7627.
87. Maoka, T.; Tsushima, M.; Nishino, H. Isolation and characterization of dinochrome A and B, Anti-carcinogenic Active Carotenoids from the Fresh Water Red Tide Peridinium bipes. Chem. Pharm. Bull., 2002, 50, 1630-1633.
88. Dembitsky, V.M.; Poovarodom, S.; Leontowicz, H.; Leontowicz, M.; Vearasilp, S.; Trakhtenberg, S.; Gorinstein, S. The multiple nutrition properties of some exotic fruits: Biological activity and active metabolites. Food Res. Int., 2011, 44, 1671-1701.
89. Kishimoto, S.; Maoka, T.; Nakayama, M.; Ohmiya, A. Carotenoid composition in petals of chrysanthemum (Dendranthema grandiflorum (Ramat.) Kitamura). Phytochemistry, 2004, 65, 2781-2787.
90. Kishimoto, S.; Maoka, T.; Sumitomo, K.; Ohmiya, A. Analysis of carotenoid composition in petals of calendula (Calendula officinalis L.). Biosci., Biotechnol., Biochem., 2005, 69, 2122-2128.
91. Suzuki, M.; Watanabe, K.; Fujiwara, S.; Kurasawa, T.; Wakabayashi, T.; Tsuzuki, M.; Iguchi, K.; Yamori, T. Isolation of peridinin-related norcarotenoids with cell growth-inhibitory activity from the cultured dinoflagellate of Symbiodinium sp., a symbiont of the Okinawan soft coral Clavularia viridis, and analysis of fatty acids of the dinoflagellate. Chem. Pharm. Bull., 2003, 51, 724-727.
92. Hornero-Méndez, D.; Mínguez-Mosquera, M.I. Carotenoid pigments in Rosa mosqueta hips, an alternative carotenoid source for foods. J. Agric. Food Chem., 2000, 48, 825-828.
93. Pasquet, V.; Morisset, P.; Ihammouine, S.; Chepied, A.; Aumailley, L.; Berard, J.B.; Serive, B.; Kaas, R.; Lanneluc, I.; Thiery, V.; Lafferriere, M.; Piot, J.M.; Patrice, T.; Cadoret, J.P.; Picot, L. Antiproliferative Activity of violaxanthin isolated from bioguided fractionation of Dunaliella tertiolecta Extracts. Marine Drugs, 2011, 9, 819-831.
94. Häder, D.P.; Lebert, M.; Sinha, R.P.; Barbieri, E.S.; Helbling, E.W. Role of protective and repair mechanisms in the inhibition of photosynthesis in marine macroalgae. Photochem. Photobiol. Sci: Official journal of the European Photochemistry Association and the European Society for Photobiology, 2002, 1, 809-814.
95. Bonente, G.; Ballottari, M.; Truong, T.B.; Morosinotto, T.; Ahn, T.K.; Fleming, G.R.; Niyogi, K.K.; Bassi, R. Analysis of LhcSR3, a protein essential for feedback de-excitation in the green alga Chlamydomonas reinhardtii. PLoS Biol., 2011, 9, e1000577.
96. Goss, R. Substrate specificity of the violaxanthin de-epoxidase of the primitive green alga Mantonielle squamata (Prasinophyceae). Planta, 2003, 217, 801-812.
97. Tanabe, Y.; Shitara, T.; Kashino, Y.; Hara, Y.; Kudoh, S. Utilizing the effective xanthophyll cycle for blooming of Ochromonas smithii and O. itoi (Chrysophyceae) on the snow surface. PloS One, 2011, 6, e14690.
98. Szabolcs, J. Some Studies on the Stereochemistry of Carotenoids. Pure Appl. Chem., 1976, 47, 147-159.
99. Eugster Conrad H. Carotenoid structures, old and new problems. Phytochemistry, 1985, 57, 639-647.
100. Czeczuga, B. Changes in the content of carotenoids in specimens of Helix pomatia (L.) (Mollusca: Gastropoda: Helicidae) in the period of their life activity. Compar. Biochem. Physiol. Part B: Biochem. Mol. Biol., 1985, 80, 657-660.
101. Matus, Z.; Molnár, P.; Szabó, L. G. Main carotenoids in pressed seeds (Cucurbitae semen) of oil pumpkin (Cucurbita pepo convar. pepo var. styriaca). Acta Pharm. Hungarica, 1993, 63, 247-256.
102. Asai, A.; Sugawara, T.; Ono, H.; Nagao, A. Biotransformation of fucoxanthinol into amarouciaxanthin A in mice and HepG2 cells: formation and cytotoxicity of fucoxanthin metabolites. Drug Metab. Dispos.: Biological Fate Of Chemicals, 2004, 32, 205-211.
103. Asai, A.; Yonekura, L.; Nagao, A. Low bioavailability of dietary epoxyxanthophylls in humans. Br. J. Nutr., 2008, 100, 273-277.
104. Hashimoto T.; Ozaki Y.; Mizuno M.; Yoshida M.; Nishitani Y; Azuma T.; Komoto A.; Moaka T.; Tanino Y.; Kanazawa K. Pharmacokinetics of fucoxanthinol in human plasma after the oral administration of kombu extract. Br. J. Nutr., 2011, 16, 1-4.
105. Vogel, P. Derivatives of 7-oxabicyclo[2.2.1]heptane in nature and as useful synthetic intermediates. Tetrahedron, 1999, 55, 13521-13642.
106. Grung, M.; Liaaen-jensen, S. Algal Carotenoids 52*; Secondary Carotenoids of Algae 3; Carotenoids in a natural bloom of Euglena sanguinea. Biochem. System. Ecol., 1993, 21, 757-763.
107. Molnár, P.; Deli, J.; Tóth, G.; Häberli, A.; Pfander, H.; Bernhard, K. (9Z)-capsanthin-5,6-epoxide, a new carotenoid from the fruits of Asparagus falcatus. J. Nat. Prod., 2001, 64, 1254-1255.
108. Molnár, P. Research of the (E/Z)-isomerization of carotenoids in Pécs since the 1970s. Arch. Biochem. Biophys., 2009, 483, 156-164.
109. Maoka, T.; Hashimoto, K.; Akimoto, N.; Fujiwara, Y. Structures of five new carotenoids from the oyster Crassostrea gigas. J. Nat. Prod., 2001, 64, 578-581.
110. Lorand, T.; Molnar, P.; Deli, J.; Toth, G. FT-IR study of some seco-and apocarotenoids. J. Biochem. Biophys. Methods, 2002, 53, 251-258.
111. Molnár, P.; Szabolcs, J. Citraurin epoxide, a new carotenoid from valencia orange peel. Phytochemistry, 1980, 19, 633-637.
112. Liaaen-jensen, S. New structures. Pure Appl. Chem., 1976, 47, 129-145.
113. Tsushima, M.; Mune, E.; Maoka, T.; Matsuno, T. Isolation of stereoisomeric epoxy carotenoids and new acetylenic carotenoid from the common freachwater goby Rhinogobius brunneus. J. Nat. Prod., 2000, 63, 960-964.
114. Guglielmi, G.; Lavaud, J.; Rousseau, B.; Etienne, A.L.; Houmard, J.; Ruban, A.V. The light-harvesting antenna of the diatom Phaeodactylum tricornutum. Evidence for a diadinoxanthin-binding subcomplex. FEBS J., 2005, 272, 4339-4348.
115. Venn, A.A.; Wilson, M.A.; Trapido-Rosenthal, H.G.; Keely, B.J.; Douglas, A.E. The impact of coral bleaching on the pigment profile of the symbiotic alga, Symbiodinium. Plant, Cell Environ., 2006, 29, 2133-2142.
116. Johansen, J.E.; Svec, W.A.; Liaaen-Jensen, S.; Haxo, F.T. Carotenoids of the dinophyceae. Phytochemistry, 1974, 13, 2261-2271.
117. Bjørnland, T. Gyroxanthin-the first allenic acetylenic carotenoid. Tetrahedron, 2000, 56, 9047-9056.
118. Hertzberg, S.; Partali, V.; Liaaen-Jensen, S. Animal carotenoids. 32. Carotenoids of Mytilus edulis (edible mussel). Acta Chem. Scand.-Series B, 1988, 42, 495-503.
119. Aakermann, T.; Guillard, R.R.L.; Liaaen-Jensen, S. Algal carotenoids 55. Structure elucidation of P457. Part1. Reisolation, Derivatization and synthesis of model compounds. Acta Chem. Scand., 1993, 47, 1207-1213.
120. Englert, G.; Aakemann, T.; Schiedt, K.; Liaaen-Jensen, S. Structure elucidation of the algal carotenoid (3S,5R,6R,3'S,5'R,6'S)-13'-cis-7',8'-dihydroneoxanthin-20'-AL 3'-beta-lactoside (P457). Part 2, Nmr studies. J. Nat. Prod., 1995, 58, 1675-1682.
121. Gross, J.; Eckhardt, G. Structures of persicaxanthin, persicachrome and other apocarotenols of various fruits. Phytochemistry, 1981, 20, 2267-2269.
122. Egeland, E. Ten minor carotenoids from prasinophyceae (chlorophyta). Phytochemistry, 1995, 40, 515-520.
123. Maoka, T.; Akimoto, N.; Yim, M.J.; Hosokawa, M.; Miyashita, K. New C37 skeletal carotenoid from the clam, Paphia amabillis. J. Agric. Food Chem., 2008, 56, 12069-12072.
124. Matsuno, T.; Tsushima, M.; Maoka, T. Salmoxanthin, deepoxysalmoxanthin, and 7,8-didehydrodeepoxysalmoxanthin from the Salmon Oncorhynchus keta. J. Nat. Prod., 2001, 64, 507-510.
125. Egeland, E.S.; Guillard, R.R.L.; Liaaen-Jensen, S. Additional carotenoid prototype representatives and a general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta). Science, 1997, 44, 1087-1097.
126. Egeland, E.S.; Johnsen, G.; Eikrem, W.; Throndsen, J.; Liaaen-Jensen, S. Pigments of Bathycoccus prasinos (Prasinophyceae): Methodological and chemosystematic implications. J. Phycol., 1995, 31, 554-561.
127. Egeland, E. Carotenoids from further prasinophytes. Biochem. Syst. Ecol., 1995, 23, 747-755.
128. Foss, P.; Guillard, R.R.L.; Liaaen-Jensen, S. Carotenoids from eucaryotic ultraplankton clones (prasinophyceae). Phytochemistry, 1985, 25, 119-124.
129. Gross, J.; Carmon, M.; Lifshitz, A.; Sklarz, B. Structural elucidation of some orange juice carotenoids. Phytochemistry, 1975, 14, 249-252.
130. Rodriguez, E.B.; Rodriguez-amaya, D.B. Formation of apocarotenals and epoxycarotenoids from α-carotene by chemical reactions and by autoxidation in model systems and processed foods. Food Chem., 2007, 101, 563-572.
131. Maoka, T.; Akimoto, N.; Ishiguro, K.; Yoshinaga, M.; Yoshimoto, M. Carotenoids with a 5,6-dihydro-5,6-dihydroxy-beta-end group, from yellow sweet potato "Benimasari", Ipomoea batatas Lam. Phytochemistry, 2007, 68, 1740-1745.
132. Nagy, V.; Agócs, A.; Turcsi, E.; Molnár, P.; Szabó, Z.; Deli, J. Latoxanthin, a minor carotenoid isolated from the fruits of yellow paprika (Capsicum annuum var. lycopersiciforme flavum). Tetrahedron Lett., 2007, 48, 9012-9014.
133. Maoka, T.; Akimoto, N.; Kuroda, Y.; Hashimoto, K.; Fujiwara, Y. Pittosporumxanthins, cycloaddition products of carotenoids with alpha-tocopherol from seeds of Pittosporum tobira. J. Nat. Prod., 2008, 71, 622-627.
134. Fujiwara, Y.; Hashimoto, K.; Manabe, K.; Maoka, T. Structures of tobiraxanthins A1, A2, A3, B, C and D, new carotenoids from the seeds of Pittosporum tobira. Tetrahedron Lett., 2002, 43, 4385-4388.
135. Maoka, T.; Fujiwara, Y.; Hashimoto, K.; Akimoto, N. 5-Hydroxyseco-carotenoids from Pittosporum tobira. Phytochemistry, 2006, 67, 2120-2125.
136. Brown, J.S. Functional Organization of Chlorophyll a and Carotenoids in the Alga, Nannochloropsis salina. Plant Physiol., 1987, 83, 434-437.
137. Mangoni, O.; Imperatore, C.; Tomas, C.R.; Costantino, V.; Saggiomo, V.; Mangoni, A. The new carotenoid pigment moraxanthin is associated with toxic microalgae. Marine Drugs, 2011, 9, 242-255.
138. Meléndez-Martínez, A.J.; Vicario, I.M.; Heredia, F.J. Effect of ascorbic acid on deterioration of carotenoids and colour in ultrafrozen orange juice. J. Food Compos. Anal., 2009, 22, 295-302.
139. Deli, V. J.; Mólnar, P.; Toth, G.; Baumeler, A.; Eugster, C.H. 80. Cycloviolaxanthin (= (3S,5R,6R,3'S,5'R,6'R)-3,6:3',6'-Diepoxy 5,6,5',6'-tetrahydro-α,-carotin-5,5'-diol), ein neues Carotinoid aus Paprika (Capsicum annuum). Helv. Chim. Acta, 1991, 74, 819-824.
140. Lakshminarayana, R.; Aruna, G.; Sangeetha, R.K.; Bhaskar, N.; Divakar, S.; Baskaran, V. Possible degradation/biotransformation of lutein in vitro and in vivo: isolation and structural elucidation of lutein metabolites by HPLC and LC-MS (atmospheric pressure chemical ionization). Free Radic. Biol. Med., 2008, 45, 982-993.
141. Liu, I.S. Isolation and identification of carotenoids in the yeast Rhodotorula aurantiaca C.B.S. 317, PhD Thesis, The Rhode Island Kingston University, 1973.
142. Karrer, P.; Jucker, E.; Steinlin, K. Rubichrome, a new carotenoid with a furanoid ring system, occuring in nature. Helv. Chim. Acta, 1947, 30, 531-535.