Siphonaxanthin, a green algal carotenoid, as a novel functional compound

Marine Drugs

Volumn 12, Issue 6, 2014, Pages 3660-3668

  Sugawara, Tatsuya ^a   Ganesan, Ponesakki ^a,b   Li, Zhuosi ^a   Manabe, Yuki ^a   Hirata, Takashi ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b SRM INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

^c SHIJONAWATE GAKUEN UNIVERSITY   (Japan)

Author keywords

Angiogenesis; Apoptosis; Carotenoid; Green algae; Inflammation; Siphonaxanthin

Indexed keywords

CAROTENOID; DEATH RECEPTOR 5; FIBROBLAST GROWTH FACTOR RECEPTOR 1; FUCOXANTHIN; IMMUNOGLOBULIN E RECEPTOR; PROTEIN BCL 2; SIPHONAXANTHIN; TUMOR NECROSIS FACTOR RELATED APOPTOSIS INDUCING LIGAND; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 2; ANGIOGENESIS INHIBITOR; XANTHOPHYLL;

ANTIANGIOGENIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; CAULERPA LENTILLIFERA; CELL VIABILITY; CODIUM FRAGILE; CONCENTRATION RESPONSE; DOWN REGULATION; DRUG EFFICACY; DRUG MECHANISM; DRUG STRUCTURE; GREEN ALGA; HUMAN; NONHUMAN; PROTEIN EXPRESSION; REVIEW; SIGNAL TRANSDUCTION; UMBRAULVA JAPONICA; UPREGULATION; ANIMAL; CELL SURVIVAL; COMPARATIVE STUDY; DRUG EFFECTS; ENDOTHELIUM CELL; ISOLATION AND PURIFICATION; METABOLISM; RAT;

ANGIOGENESIS INHIBITORS; ANIMALS; APOPTOSIS; CELL SURVIVAL; CHLOROPHYTA; ENDOTHELIAL CELLS; HUMANS; RATS; SIGNAL TRANSDUCTION; XANTHOPHYLLS;

EID: 84903531452     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12063660     Document Type: Review

References (46)

1. Mabeau, S.; Fleurence, J. Seaweed in food products: Biochemical and nutritional aspects. Trends Food Sci. Technol. 1993, 4, 103-107. (Pubitemid 23687665)
2. Fleurence, J. Seaweed proteins: Biochemical, nutritional aspects and potential uses. Trends Food Sci. Technol. 1999, 10, 25-28. (Pubitemid 29247432)
3. Peng, J.; Yuan, J.P.; Wu, C.F.; Wang, J.H. Fucoxanthin, a marine carotenoid present in brown seaweeds and diatoms: Metabolism and bioactivities relevant to human health. Mar. Drugs 2011, 9, 1806-1828.
4. Kumar, S.R.; Hosokawa, H.; Miyashita, K. Fucoxanthin: A marine carotenoid exerting anti-cancer effects by affecting multiple mechanisms. Mar. Drugs 2013, 11, 5130-5147.
5. Takaichi, S. Carotenoids in algae: Distributions, biosynthesis and functions. Mar. Drugs 2011, 9, 1101-1118.
6. 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. (Pubitemid 33136153)
7. Kotake-Nara, E.; Sugawara, T.; Nagao, A. Antiproliferative effect of neoxanthin and fucoxanthin on cultured cells. Fish. Sci. 2005, 71, 459-461. (Pubitemid 40689911)
8. Hosokawa, M.; Kudo, M.; Maeda, H.; Kohno, H.; Tanaka, T.; Miyashita, K. Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPARγ ligand, troglitazone, on colon cancer cells. Biochim. Biophys. Acta 2004, 1675, 113-119.
9. Das, S.K.; Hashimoto, T.; Shimizu, K.; Yoshida, T.; Sakai, T.; Sowa, Y.; Komoto, A.; Kanazawa, K. Fucoxanthin induces cell cycle arrest at G0/G1phase in human colon carcinoma cells through up-regulation of p21WAF1/Cip1. Biochim. Biophys. Acta 2005, 1726, 328-335.
10. Sachindra, N.M.; Sato, E.; Maeda, H.; Hosokawa, M.; Niwano, Y.; Kohno, M.; Miyashita, K. Radical scavenging and singlet oxygen quenching activity of marine carotenoid fucoxanthin and its metabolites. J. Agric. Food Chem. 2007, 55, 8516-8522. (Pubitemid 350013096)
11. 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. (Pubitemid 40724991)
12. Maeda, H.; Hosokawa, M.; Sashima, T.; Takahashi, N.; Kawada, T.; Miyashita, K. Fucoxanthin and its metabolite, fucoxanthinol, suppress adipocyte differentiation in 3T3-L1 cells. Int. J. Mol. Med. 2006, 18, 147-152.
13. Miyashita, K.; Nishikawa, S.; Beppu, A.; Tsukui, A.; Abe, M.; Hosokawa, M. The allenic carotenoid fucoxanthin, a novel marine nutraceutical from brown seaweeds. J. Sci. Food Agric. 2011, 91, 1166-1174.
14. 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. (Pubitemid 46158974)
15. Akimoto, S.; Tomo, T.; Naitoh, Y.; Otomo, A.; Murakami, A.; Mimuro, M. Identification of a new excited state responsible for the in vivo unique absorption band of siphonaxanthin in the green alga Codium fragile. J. Phys. Chem. 2007, 111, 9179-9181. (Pubitemid 47280513)
16. Chen, G.; Niu, X.; Chen, X.; Li, L.; Kuang, T.; Li, S. Characterization of chlorophyll protein complexes isolated from a siphonous green alga, Bryopsis corticulans. Photosynth. Res. 2008, 96, 75-81.
17. Mimuro, M.; Katoh, T. Carotenoids in photosynthesis: Absorption, transfer and dissipation of light energy. Pure Appl. Chem. 1991, 63, 123-130.
18. Akimoto, S.; Yokono, M.; Higuchi, M.; Tomo, T.; Takaichi, S.; Murakami, A.; Mimuro, M. Solvent effects on excitation relaxation dynamics of a keto-carotenoid, siphonaxanthin. Photochem. Photobiol. Sci. 2008, 7, 1206-1209.
19. Wang, W.; Qin, X.; Sang, M.; Chen, D.; Wang, K.; Lin, R.; Lu, C.; Shen, J.; Kuang, T. Spectral and functional studies on siphonaxanthin-type light-harvesting complex of photosystem II from Bryopsis corticulans. Photosynth. Res. 2013, 117, 267-279.
20. 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 triguetra. Biosci. Biotechnol. Biochem. 2007, 71, 1069-1072. (Pubitemid 46650949)
21. 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. (Pubitemid 46985050)
22. Ganesan, P.; Noda, K.; Manabe, Y.; Ohkubo, T.; Tanaka, Y.; Maoka, T.; Sugawara, T.; Hirata, T. Siphonaxanthin, a marine algal carotenoids from green algae, effectively induces apoptosis in human leukemia (HL-60) cells. Biochim. Biophys. Acta 2011, 1810, 497-503.
23. Srivastava, R.K. TRAIL/Apo-2L: Mechanisms and clinical applications in cancer. Neoplasia 2001, 3, 535-546. (Pubitemid 33151020)
24. Folkman, J.; Shing, Y. Angiogenesis. J. Biol. Chem. 1992, 267, 10931-10934.
25. Carmeliet, P.; Jain, R.K. Angiogenesis in cancer and other diseases. Nature 2000, 407, 249-257.
26. Folkman, J. Angiogenesis in cancer, vascular, rheumatoid and other diseases. Nat. Med. 1995, 1, 27-31.
27. Virmani, R.; Kolodgie, F.D.; Burke, A.P.; Finn, A.V.; Gold, H.K.; Tulenko, T.N.; Wrenn, S.P.; Narula, J. Atherosclerotic plaque progression and vulnerability to rupture: Angiogenesis as a source of intraplaque hemorrhage. Atheroscler. Thromb. Vasc. Biol. 2005, 25, 2054-2061. (Pubitemid 41416300)
28. Folkman, J. Influence of geometry on growth of normal and malignant cells. Adv. Pathobiol. 1976, 4, 12-28.
29. Carmeliet, P. Angiogenesis in life, disease and medicine. Nature 2005, 438, 932-936. (Pubitemid 43093958)
30. Matsubara, K.; Mori, M.; Matsuura, Y.; Kato, N. Pyridoxal 5′-phosphate and pyridoxal inhibit angiogenesis in serum-free rat aortic ring assay. Int. J. Mol. Med. 2001, 8, 505-508.
31. Matsubara, K.; Mori, M.; Matsumoto, H.; Hori, K.; Miyazawa, K. Antiangiogenic properties of a sulfated galactan isolated from a marine alga, Codium cylindricum. J. Appl. Phycol. 2003, 15, 87-90. (Pubitemid 36435000)
32. Matsubara, K.; Kaneyuki, T.; Miyake, T.; Mori, M. Antiangiogenic activity of nasunin, an antioxidant anthocyanin, in eggplant peels. J. Agric. Food Chem. 2005, 53, 6272-6275. (Pubitemid 41169372)
33. Matsubara, K.; Xue, C.; Zhao, X.; Mori, M.; Sugawara, T.; Hirata, T. Effects of middle molecular weight fucoidans on in vitro and ex vivo angiogenesis of endothelial cells. Int. J. Mol. Med. 2005, 15, 695-699.
34. Mori, M.; Sadahira, Y.; Kawasaki, S.; Hayashi, T.; Notohara, K.; Awai, M. Capillary growth from reversed rat aortic segments cultured in collagen gel. Acta Pathol. Jpn. 1988, 38, 1503-1512. (Pubitemid 19063126)
35. Kawasaki, S.; Mori, M.; Awai, M. Capillary growth of rat aortic segments cultured in collagen gel without serum. Acta Pathol. Jpn. 1989, 39, 712-718. (Pubitemid 20055673)
36. Ganesan, P.; Matsubara, K.; Ohkubo, T.; Tanaka, Y.; Noda, K; Sugawara, T.; Hirata, T. Anti-angiogenic effect of siphonaxanthin from green alga, Codium fragile. Phytomedicine 2010, 17, 1140-1144.
37. Hicklin, D.J.; Ellis, L.M. Role of vascular endothelial growth factor pathway in tumor growth and angiogenesis. J. Clin. Oncol. 2005, 23, 1011-1027. (Pubitemid 46202320)
38. Fahmy, R.G.; Dass, C.R.; Sun, L.; Chesterman, C.N.; Khachigian, L.M. Transcription factor Egr-1 supports FGF-dependent angiogenesis during neovascularization and tumor growth. Nat. Med. 2003, 9, 1026-1032. (Pubitemid 37021782)
39. Ganesan, P.; Matsubara, K.; Sugawara, T.; Hirata, T. Marine algal carotenoids inhibit angiogenesis by down-regulating FGF-2-mediated intracellular signals in vascular endothelial cells. Mol. Cell. Biochem. 2013, 380, 1-9.
40. Gilfillan, A.M.; Tkaczyk, C. Integrated signaling pathways for mast-cell activation. Nat. Rev. Immunol. 2006, 6, 218-230. (Pubitemid 43290991)
41. Sakai, S.; Sugawara, T.; Matsubara, K.; Hirata, T. Inhibitory effect of carotenoids on the degranulation of mast cells via suppression of antigen-induced aggregation of high affinity IgE receptors. J. Biol. Chem. 2009, 284, 28172-28179.
42. Field, K.A.; Holowka, D.; Baird, B. Compartmentalized activation of the high affinity immunoglobulin E receptor within membrane domains. J. Biol. Chem. 1997, 272, 4276-4280. (Pubitemid 27078498)
43. Sakai, S.; Sugawara, T.; Hirata, T. Inhibitory effect of dietary carotenoids on dinitrofluorobenzene-induced contact hypersensitivity in mice. Biosci. Biotechnol. Biochem. 2011, 75, 1013-1015.
44. Manabe, Y.; Hirata, T.; Sugawara, T. Suppressive effects of carotenoids on the antigen-induced degranulation in RBL-2H3 rat basophilic leukemia cells. J. Oleo Sci. 2014, 63, 291-294.
45. 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. (Pubitemid 34493558)
46. Asai, A.; Sugawara, T.; Ono, H.; Nagao, A. Biotransformation of fucoxanthinol to amarouciaxanthin A in mice and HepG2 cells: Formation and cytotoxicity of fucoxanthin metabolites. Drug Metab. Dispos. 2004, 32, 205-211. (Pubitemid 38176937)