A novel retinoic acid analogue, 7-hydroxy retinoic acid, isolated from cyanobacteria

Biochimica et Biophysica Acta - General Subjects

Volumn 1810, Issue 4, 2011, Pages 414-419

  Kaya, Kunimitsu ^a   Shiraishi, Fujio ^b   Uchida, Hideaki ^c   Sano, Tomoharu ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NATIONAL INSTITUTE FOR ENVIRONMENTAL STUDIES   (Japan)

^c YOKOGAWA ANALYTICAL SYSTEMS INC   (Japan)

Author keywords

7 hydroxy retinoic acid; Cyanobacteria; RAR agonistic activity; UV stability

Indexed keywords

7 HYDROXY RETINOIC ACID; RETINOIC ACID DERIVATIVE; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CONTROLLED STUDY; CYANOBACTERIUM; DRUG ISOLATION; FRACTIONATION; HYDROGENATION; MICROCYSTIS AERUGINOSA; MOLECULAR STABILITY; NONHUMAN; PHOTOSENSITIVITY; PRIORITY JOURNAL; SPIRULINA;

HUMANS; MICROCYSTIS; RECEPTORS, RETINOIC ACID; SPIRULINA; TRETINOIN; TWO-HYBRID SYSTEM TECHNIQUES;

ANIMALIA; CYANOBACTERIA; MICROCYSTIS AERUGINOSA; SPIRULINA SP.;

EID: 79551628068     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2010.11.009     Document Type: Article

References (34)

1. R.A. Heyman, D.J. Mangelsdorf, J.A. Dyck, R.B. Stein, and G. Rabjohn R.M Evans, and C. Thaller. 9-cis Retinoic acid is a high affinity ligand for the retinoid-X receptor Cell 68 1992 397 406
2. A.A. Levin L.J.bSturzenbecker, S. Kazmer, T. Bosakowski, C. Huseltonc, G. Allenby, J. Speck, C. Kratzeisen, M. Rosenberger, A. Lovey, and J.F. Grippo. 9-cis Retinoic acid stereoisomer binds and activates the nucleo receptor RXR-alpha Nature 355 1992 359 361
3. J.C. Kraft, T. Schuh, and M. Juchau and. Kimelman. The retinoid-X receptor-ligand, 9-cis retinoic acid, is a potential regulator of early Xenopus development Proc. Natl. Acad. Sci. USA 91 1994 3067 3071 (Pubitemid 24130176)
4. A.M. McCormick, J.L. Napoli, H.K. Schnoes, and H.F. Deluca Isolation and identification of 5, 6-epoxyretinoic acid-biologically-active metabolite of retinoic acid Biochemistry 17 1978 4085 4090 (Pubitemid 9036529)
5. C.A. Frolik, A.B. Roberts, T.E. Tavela, P.P. Roller, D.L. Newton, and M.B. Sporn Isolation and identification of 4-hydroxyretinoic acid and 4-oxoretinoic acid-Invitro metabolites of all trans- retinoic acid in hamster trachea and liver Biochemistry 18 1979 2092 2097 (Pubitemid 9173562)
6. J.A. White Y-D. Guo, K. Baetz, B. Beckett-Jones, J. Banasoro, K. Hsu, F. J. Dilworth, G. Jones, and M. Petkovich, Identification of retinoic acid-inducible all trans-retinoic acid 4-hydroxylase J. Biol. Chem. 271 1996 29922 29927
7. H. Fujii, T. Sato, S. Kaneko, O. Gotoh, Y. Fujii-Kuriyama, K. Osawa, and S. Kato S, and Hamada, H. Metabolic inactivation of retinoic acid by a novel P450 differentially expressed in developing mouse embryos EMBO J. 16 1997 4163 4173 (Pubitemid 27298169)
8. J.A. White, and B. Beckett-Jones Y-D. Guo, F. J. Dilworth, J. Bonasoro, G. Jones, and M. Petkovich, cDNA cloning of human retinoic acid-metabolizing enzyme (hP450RAI) indentifies a novel family of Cytochromes P450 J. Biol. Chem. 272 1997 18538 18541 (Pubitemid 27318190)
9. W. Ray, G. Bain, M. Yao, and D.I. Gottlieb CYP26, a novel mammalian Cytochrome P450, Is induced by retinoic acid and defines a new family J. Biol. Chem. 272 1997 18702 18708 (Pubitemid 27318214)
10. S.S. Abu-Abed, B.R. Beckett, H. Chiba, J.V. Chithalen, G. Jones, D. Metzger, P. Chambon, and M. Petkovich Mouse P450RAI (CYP26) expression and retinoic acid-inducible retinoic acid metabolism in F9 cells are regulated by retinoic acid receptor γ and retinoid X receptor α Proc. Natl. Acad. Sci. USA 77 1997 3230 3233
11. M.H. Zile, H.K. Schnoes, and H.F. DeLuca Characterization of retinyl beta-glucuronide as minor metabolite of retinoic acid in bile Proc. Natl. Acad. Sci. USA 77 1980 3230 3233 (Pubitemid 10016926)
12. M.H. Zile, R.C. Inborn, and H.F. DeLuca Metabolites of all-trans-retinoic acid in bile- identification of all-trans retinoyl and 13-cis- retinyl glucronides J. Biol. Chem. 257 1982 35373543
13. M.H. Zile, R.C. Inborn, and H.F. DeLuca Metabolism in vivo of all-trans retinoic acid- biosynthesis of 13-cis retinoic acid and all-trans retinyl and 13-cis retinyl glucronides in the intestinal-mucosa of the rat J. Biol. Chem. 257 1982 3544 3550 (Pubitemid 12077136)
14. G.J. Fisher, and J.J. Voorhees Molecular mechanisms of retinoid actions in skin FASEB J. 10 1996 1002 1013 (Pubitemid 26285976)
15. J.L. Napoli Retinoic acid biosynthesis and metabolism FEBS J. 10 1996 993 1001 (Pubitemid 26285975)
16. E. Grenier, F.S. Maupas, J.F. Beaulieu, E. Seidman, E. Delvin, A. Sane, E. Tremblay, C. Carofalo, and E. Levy Effect of retinoic acid on cell proliferation and differentiation as well as on lipid synthesis, lipoprotein secretion, and apolipoprotein biogenesis Am. J. Physiol. Gastrointest. Liver Physiol. 293 2007 G1178 G1189
17. J.R. Mora, M. Iwata, B. Eksteen, S.Y. Song, T. Junt, B. Senman, K.L. Otipoby, A. Yokota, H. Takeuchi, P. Ricciardi-Castagnolo, K. Rajewsky, D.H. Adams, and U.H. von Andrian Generation of gut-himing IgA-secreting B cells by intestinal dendritic cells Science 314 2006 1157 1160 (Pubitemid 44789048)
18. M. Iwata, Y. Eshima, and H. Kagechika Retinoic acids exert direct effects on T cells to suppress T(h)1 development and enhance T(h)2 development via retinoic acid receptors Int. Immunol. 15 2003 1017 1025 (Pubitemid 36987299)
19. C.N. Ellis, L.E. Milikan, E.B. Smith, D.M. Chalker, L.J. Swinyer, I.H. Katz, R.S. Berger, O.H. Mills, M. Baker, M. Verschoore, and C. Loesche Comparison of adapalene 0.1% solution and tretinoin 0.025% gel in the topical treatment of acne vulgaris Br. J. Dermatol. 139 Suppl 52 1998 41 47
20. C.A. Frolik, P.P. Roller, A.B. Roberts, and M.B. Sporn In vitro and in vivo metabolism of all trans and 13-cis retinoic acid in hamsters J. Biol. Chem. 255 1980 8057 8062
21. T. Sano, and H. Takagi and KJ. Kaya, A Dhb-microcystin from the filamentous cyanobacterium Planktothrix rubescens Phytochemistry 65 2004 2159 2162 (Pubitemid 38981672)
22. R. Kamata, F. Shiraishi, J. Nishikawa, J. Yonemoto, and H. Shiraishi Screening and detection of the in vitro agonistic activity of xenobiotics on the retinoic receptor Toxicol. in Vitro 22 2008 1050 1061
23. K. Kaya, K. Uchida, and T. Kusumi Identification of taurine-containing lipid in Tetrahymena pyriformis NT-1 Biochim. Biophys. Acta 835 1985 77 82 (Pubitemid 15019650)
24. S. Kikuchi, T. Kubo, and K. Kaya Cylindrospermopsin determination using 2-[4-(2- hydroxyethyl)-1-piperazinyl]ethanesulfonic acid (HEPES) as the internal standard Anal. Chim. Acta 583 2007 124 127 (Pubitemid 46037632)
25. J.V. Chithalen, L. Luu, M. Petkovich, and G. Jones HPLC-MS/MS analysis of the products generated from all-trans-retinoic acid using recombinant human CYP26A J. Lipid Res. 43 2002 1133 1142 (Pubitemid 34760885)
26. M. Windholz, S. Budavari, L.Y. Stroumtsos, M.R. Fertig, Retinoic Acid, "The Merck Index" Ninth edition 1976 Merck & Co. Inc, Rahway N.J., U.S.A 7961
27. R.M. Silverstein, G.C. Bassler, and T.C. Morrill R.M. Silverstein, G.C. Bassler, T.C. Morrill, Chapter 7. Utraviolet Spectrometry, pp269-270 "Spectrometric Identification of Organic Compounds" Fifth edition 1991 John Wiley & Sons Inc New York, USA
28. G.A. Codd, S.M.F.O. Azevedo, S.N. Bagchi, M.D. Burch, W.W. Carmichael, W.R. Harding, K. Kaya, and H.C. Utkilen Cyanonet: Aglobal Network for Cyanobacterial Bloom and Toxin Risk Management UNESCO Technical Documents in Hydrology 76 2005 UNESCO'S Workshops Paris France 138
29. K. Kaya D-Y. Liu, U-W.Shen, B-D. Xiao, and T. Sano, Selective control of toxic Microcystis water blooms using lysine and malonic acid: an enclosure experiment Environ. Toxicol. 20 2005 170 179
30. P.J. Proteau, W.H. Gerwick, F. Garcia-Pichel, and R. Castenholz The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria Experimentia 49 1993 825 829 (Pubitemid 23285605)
31. V. Bultel-Poncé, F. Felix-Theodore, and C. Sarthon J-F. Ponge, and B. Bodo, New pigments from the terrestrial cyanobacterium Scytonema sp. collected on the Mitaraka Inselberg, French Guyana J. Nat. Prod. 67 2004 678 681 (Pubitemid 38533945)
32. J.G. Dillon, C.M. Tatsumi, P.G. Tandingan, and R.W. Castenholz Effect of environmental factors on the synthesis of scytomenin, a UV-screening pigment, in a cyanobacterium (Chroococcidiopsis sp.) Arch. Microbiol. 177 2002 322 331 (Pubitemid 34230669)
33. C.S. Cockell The biological effects of high ultraviolet radiation on early Earth - a theoretical evaluation J. Theor. Biol. 193 1998 717 731
34. R.P. Sinha, and D.E.-P. Häder UV-protectants in cyanobacteria Plant Sci. 174 2008 278 289