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COMMON NAME | : | Peridinin |
SYMBOL | : | |
FORMULA | : | C39H50O7 MOL.WT (average) : 630.810 |
BIOLOGICAL ACTIVITY |
PHYSICAL AND CHEMICAL PROPERTIES |
MELTING POINT | : | 107-109![]() 127-131 ![]() |
BOILING POINT | : | |
REFRACTIVE INDEX | : | |
OPTICAL ROTATION | : | |
DENSITY | : | |
SOLUBILITY | : |
SPECTRAL DATA |
UV SPECTRA | : | lmax (nm): ethanol 472 (Ref. 0002); EtOH 475 (E 1%1cm = 1325) (Ref. 0033); hexane 431sh, 456 and 485 (Ref. 0002); acetone 465 (Ref. 0033); hexane/acetone/methanol (89:10:1) 427 sh, 457, 479 sh; hexane 425 sh, 453, 482, %III/II=61 (Ref. 1165); methanol [Spectrum 1104] |
IR SPECTRA | : | nmax(CD Cl3)/cm-1: 3600 and 3450 (OH), 1928 (allene) and 1742 (C=O) (Ref. 0002) nmax(KBr)/cm-1: 3427 (OH), 3023-2958, 2853 (CH), 1927 (allene), 1739 (C=O), 1640, 1617, 1596, 1521, 1450 (CH2), 1377 and 1364 (gem-Me), 1247 (C-O acetate), 1182, 1161, 1124, 1070, 1046, 1029, 963 (trans disubstituted C=C), 956, 940, 904 (Ref. 0033)(Ref. 1269) |
NMR SPECTRA | : | 1H-NMR d(500 MHz, CDCl3): 0.97, 1.20, 1.21 (each 3H, s, 1'-gem-Me and 5'-Me), 1.07 and 1.35 (each 3H, s, 1-gem-Me), 1.26 (1H, dd, J 12.5, 10.5, 2'ax-H), 1.38 (3H, s, 5-Me), 1.38 (1H, dd, J 12, 6, 2ax-H), 1.50 (1H, t-like, J 13, 4ax-H), 1.63 (1H, br d-like, J 12.5, 2'eq-H), 1.64 (1H, dd, J 14.5, 9, 4'ax-H), 1.80 (3H, s, 9-Me), 1.99 (1H, ddd, J 12, 4, 2, 2eq-H), 2.04 (3H, s, OAc), 2.23 (3H, s, 13'-Me), 2.28 (1H, ddd, J 13, 4, 2, 4eq-H), 2.40 (1H, ddd, J 14.5, 4, 1.5, 4'eq-H), 3.90 (1H, m, 3'-H), 5.38 (1H, tt, J 12, 4, 3-H), 5.73 (1H, s, 12'-H), 6.05 (1H, s, 8-H), 6.11 (1H, d, J 12, 10-H), 6.37 (1H, d, J 15.5, 8'-H), 6.38 (1H, dd, J 14, 11, 12-H), 6.45 (1H, d, J 12, 14'-H), 6.51 (1H, dd, J 14, 11, 15-H), 6.61 (2H, dd, J 14, 12, 11-H and 15'-H), 7.02 (1H, s, 10'-H), 7.17 (1H, d, J 15.5, 7'-H) [Spectrum 0011] (Ref. 0002/0036/0037) Previously reported 1H-NMR assignments of all-trans-(6'R)-peridinin are partly corrected (Ref. 1165). (Ref. 1269) 13C-NMR d(100.5 MHz, CDCl3): 35.79, 35.31 (1, 1'), 45.43, 47.07 (2, 2'), 68.04, 64.13 (3, 3'), 45.26, 40.90 (4, 4'), 72.60, 67.56 (5, 5'), 117.57, 70.49 (6, 6'), 202.67, 133.62 (7, 7'), 130.29, 121.78 (8, 8'), 133.93, 124.75 (9, 9'), 128.12, 136.34 (10, 10'), 131.51, 146.76 (11, 11'), 133.00, 119.26 (12, 12'), 133.94 (13'), 138.06 (14'), 128.92, 137.25 (15, 15'), 32.07, 29.52 (16, 16'), 29.15, 24.90 (17, 17'), 31.21, 19.88 (18, 18'), 14.00, 168.78 (19, 19'), 15.40 (20'), 170.50 and 21.40 (AcO) (Ref. 0036/0037) Previously reported 13H-NMR assignments of all-trans-(6'R)-peridinin are partly corrected (Ref. 1165). |
MASS SPECTRA | : | (210![]() |
OTHER SPECTRA | : | CD data in EPA solution: De 220 (-7.1), 241 (-4.9), 270 (-4.0), 296 (-0.2), 328(-2.3), 350 (0), 365 (0.5), 404 (0.3) [Spectrum 0012] (Ref. 0002/0033/3006/0047) |
CHROMATOGRAM DATA |
SOURCE |
CHEMICAL SYNTHESIS |
METABOLISM |
GENETIC INFORMATION |
NOTE |
REFERENCES |
AUTHOR | : | Ito,M.,Hirata,Y.,Shibata,Y., and Tsukida,K. |
TITLE | : | Synthesis of the 4-Alkylidenebutenolide Carotenoids, Peridinin and Pyrrhoxanthin |
JOURNAL | : | J. Chem. Soc., Perkin Trans. 1 |
VOL | : | PAGE : 197 -199 (1990) |
AUTHOR | : | Yamano,Y. and Ito,M. |
TITLE | : | First Total Synthesis of ![]() ![]() |
JOURNAL | : | J. Chem. Soc., Perkin Trans. 1 |
VOL | : | PAGE : 1599 -1610 (1993) |
AUTHOR | : | Yamano(Hirata),Y.,Sumiya,S.,Suzuki,K.,Kurimoto,Y.,Koyama,Y., Shimamura,T., and Ito,M. |
TITLE | : | A Novel Photoproduct of Peridinin, A 6S Allenic Isomer |
JOURNAL | : | Tetrahedron Lett. |
VOL | : | 33 PAGE : 2991 -2994 (1992) |
AUTHOR | : | Yamano,Y.,Sumiya,S., and Ito,M. |
TITLE | : | Carotenoids and Related Polyenes. Part 2. Photoisomerization of an Allenic Carotenoid, Peridinin, and Allenic Model Compounds |
JOURNAL | : | J. Chem. Soc., Perkin Trans. 1 |
VOL | : | PAGE : 167 -176 (1995) |
AUTHOR | : | Mimuro,M.,Nishimura,Y.,Takaichi,S.,Yamano,Y.,Ito,M.,Nagaoka,S.,Yamazaki, I.,Katoh,T., and Nagashima,U. |
TITLE | : | The effect of molecular structure on the relaxation processes of carotenoids containg a carbonyl group |
JOURNAL | : | Chem. Phys. Lett. |
VOL | : | 213 PAGE : 576 -580 (1993) |
AUTHOR | : | Yamano,Y.,Mimuro,M., and Ito,M. |
TITLE | : | Carotenoids and related polyenes. Part 4. Synthesis of carotenoid analogues containg a conjugated carbonyl group and their fluorescence properties |
JOURNAL | : | J. Chem. Soc., Perkin Trans. 1. |
VOL | : | PAGE : 2713 -2724 (1997) |
AUTHOR | : | Ito,M.,Yamano,Y., and Shibata,Y. |
TITLE | : | Synthesis and Characterization of Carotenoids by Different Methods |
JOURNAL | : | Methods Enzymol. |
VOL | : | 213 PAGE : 13 -22 (1992) |
AUTHOR | : | Haugan,J.A.,Aakermann,R., and Liaaen-Jensen,S. |
TITLE | : | Isolation of Fucoxanthin and Peridinin |
JOURNAL | : | Methods Enzymol. |
VOL | : | 213 PAGE : 231 -245 (1992) |
AUTHOR | : | Krane,J.,Aakermann,T., and Liaaen-Jensen,S. |
TITLE | : | Algal Carotenoids 47 - NMR Study of All-Trans-Peridinin, Including Complete 1H and 13C NMR Assignments |
JOURNAL | : | Magn. Reson. Chem. |
VOL | : | 30 PAGE : 1169 -1177 (1992) |
AUTHOR | : | McLean,S.,Reynolds,W.F.,John,L.M.D., and Tinto,W.F. |
TITLE | : | Total Assignment of the 1H and 13C Spectra of Peridinin |
JOURNAL | : | Magn. Reson. Chem. |
VOL | : | 30 PAGE : 362 -363 (1992) |
AUTHOR | : | Loeblich,III,A.R. and Smith,V.E. |
TITLE | : | Chloroplast Pigments of the Marine Dinoflagellate Gyrrodinium resplendens |
JOURNAL | : | Lipids |
VOL | : | 3 PAGE : 5 -13 (1968) |
AUTHOR | : | Johansen,J.E.,Svec,W.A.,Liaaen-Jensen,S., and Haxo,F.T. |
TITLE | : | Carotenoids of the Dinophyceae |
JOURNAL | : | Phytochemistry |
VOL | : | 13 PAGE : 2261 -2271 (1974) |
AUTHOR | : | Matsuno,T. and Sakaguchi,S. |
TITLE | : | Isolation of Peridinin from The Sea Squirt Botrylloides violaceus, 'Itaboya' in Japanease |
JOURNAL | : | Bull. Japn. Soc. Scientific Fisheries |
VOL | : | 50 PAGE : 1267 -1267 (1984) |
AUTHOR | : | Strain,H.H.,Svec,W.A.,Aitzetmüller,K.,Grandolfo,M.C.,Katz,J.J.,Kjfsen,H., Norgård,S.,Liaaen-Jensen,S.,Haxo,F.T, and Rapoport, P.W.F. |
TITLE | : | The Structure of Peridinin, the Characteristic Dinoflagellate Carotenoid |
JOURNAL | : | J. Am. Chem. Soc. |
VOL | : | 93 PAGE : 1823 -1825 (1971) |
AUTHOR | : | Haxo,F.T,Kycia,H.,Somers,G.F.,Bennett,A., and Siegelman,H.W. |
TITLE | : | Peridinin-Chlorophyll a Proteins of the Dinoflagellate Amphidinium carterae (Plymouth 450) |
JOURNAL | : | Plant Physiol. |
VOL | : | 57 PAGE : 297 -303 (1976) |
AUTHOR | : | Song, P. S., Koka, P., Prezelin, B. B., and Haxo, F. T. |
TITLE | : | Molecular topology of the photosynthetic light-harvesting pigment complex, peridinin-chlorophyll a-protein, from marine dinoflagellates PubMed ID:987799 |
JOURNAL | : | Biochemistry. |
VOL | : | 15 PAGE : 4422-4427 (1976) |
AUTHOR | : | Heilbron,I.M.,Jackson,H., and Jones,R.N. |
TITLE | : | The lipochromes of sea anemones. 1. Carotenoid pigments of Actinia equina, Anemonia sulcata, Actionoloba dianthus and Tealia felina |
JOURNAL | : | Biochem. J. |
VOL | : | 29 PAGE : 1384 -1388 (1935) |
AUTHOR | : | Mimuro.M. and Katoh,T. |
TITLE | : | Carotenoids in Photosynthesis: absorption, transfer and dissipation of light energy |
JOURNAL | : | Pure Appl. Chem. |
VOL | : | 63 PAGE : 123 -230 (1991) |
AUTHOR | : | Johansen,J.E.,Borch.G., and Liaaen-Jensen,S. |
TITLE | : | Chirality of peridinin and dinoxanthin |
JOURNAL | : | Phytochemistry |
VOL | : | 19 PAGE : 441 -444 (1980) |
AUTHOR | : | Nishino,H.,Satomi,Y.,Tokuda,H.,Nishino,A.,Iwashima,A.,Tanaka,Y.,Yamano,Y.,Shibata,Y.,Torihara,M.,Tamai,Y., and Ito,M. |
TITLE | : | Anti-tumor activity of peridinin and its structurally related butenolide compounds |
JOURNAL | : | J. Kyoto Pref. Univ. Med. |
VOL | : | 100 PAGE : 831 -835 (1991) |
AUTHOR | : | Tsushima, M., Maoka, T., Katsuyama, M., Kozuka, M., Matsuno, T., Tokuda, H., Nishino, H., and Iwashima, A. |
TITLE | : | 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 PubMed ID:7742789 |
JOURNAL | : | Biol Pharm Bull. |
VOL | : | 18 PAGE : 227-233 (1995) |
AUTHOR | : | Hofmann, E., Wrench, P. M., Sharples, F. P., Hiller, R. G., Welte, W., and Diederichs, K. |
TITLE | : | Structural basis of light harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae PubMed ID:8650577 |
JOURNAL | : | Science. |
VOL | : | 272 PAGE : 1788-1791 (1996) |
AUTHOR | : | Sharples, F. P., Wrench, P. M., Ou, K., and Hiller, R. G. |
TITLE | : | Two distinct forms of the peridinin-chlorophyll a-protein from Amphidinium carterae PubMed ID:8816945 |
JOURNAL | : | Biochim Biophys Acta. |
VOL | : | 1276 PAGE : 117-123 (1996) |
AUTHOR | : | Partali,V.,Tangen,K., and Liaaen-Jensen,S. |
TITLE | : | Carotenoids in food chain studies - III Resorption and metabolic transformation of carotenoids in Mytilus edulis (Edible mussel) |
JOURNAL | : | Comp. Biochem. Physiol. |
VOL | : | 92 PAGE : 239 -246 (1989) |
AUTHOR | : | Akimoto, S., Takaichi, S., Ogata, T., Nishimura, Y., Yamazaki, I., and Mimuro, M. |
TITLE | : | Excitation energy transfer in carotenoid-chlorophyll protein complexes probed by femtosecond fluorescence decays |
JOURNAL | : | Chem. Phys. Lett. |
VOL | : | 260 PAGE : 147 -152 (1996) |
AUTHOR | : | Haugan, J.A., Englert, G., Aakermann, T., Glinz, E., and Liaaen-Jensen, S. |
TITLE | : | Algal carotenoids 58. Isomerization studies on peridinin |
JOURNAL | : | Acta Chem. Scand. |
VOL | : | 48 PAGE : 769 -779 (1994) |
AUTHOR | : | Ogata, T., Kodama, M., Nomura, S., Kobayashi, M., Nozawa, T., Katoh, T., and Mimuro, M. |
TITLE | : | A novel peridinin-chlorophyll a protein (PCP) from the marine dinoflagellate Alexandrium cohorticula: a high pigment content and plural spectral forms of peridinin and chlorophyll a PubMed ID:7805874 |
JOURNAL | : | FEBS Lett. |
VOL | : | 356 PAGE : 367-371 (1994) |
AUTHOR | : | Pinto, E., Catalani, L. H., Lopes, N. P., Di Mascio, P., and Colepicolo, P. |
TITLE | : | Peridinin as the major biological carotenoid quencher of singlet oxygen in marine algae Gonyaulax polyedra PubMed ID:10679233 |
JOURNAL | : | Biochem Biophys Res Commun. |
VOL | : | 268 PAGE : 496-500 (2000) |