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Carotenoid


DATA No : VCA0005 INFORMANT : Masayoshi Ito

NAME : (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-12',13',20'-trinor-b,b-caroten-19,11-olide

COMMON NAME: Peridinin
SYMBOL:
FORMULA: C39H50O7 MOL.WT (average) : 630.810


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Anti-tumor activity (Ref. 0097/0217).
Quencher of singlet oxygen in Gonyaulax polyedra (Ref. 1269).
Light-harvesting pigment (Ref. 0008/0009/0042/0043/0044/0046/0221/0222).
An energy transfer pathway in a peridinin-chlorophyll a protein complex (PCP) of Alexandrium tamarense (dinoflagellate) is studied by the femtosecond up-conversion method (Ref. 1114). A peridinin-chlorophyll a protein complex (PCP) of Alexandrium cohorticula (dinoflagellate) contains 37 kDa peptide, 12 peridinin and 2 chlorophyll a molecules per monomer (Ref. 1167).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:107-109degC (Ref. 0042)
127-131degC (Ref. 0041)

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:(210degC, 70 eV) m/z (ion, intensity relative to base peak in %): 630 (M, 36), 612 (M-18, 30), 594 (M-18-18, 2), 586 (M-44, 1), 570 (M-60, 9), 568 (M-18-44, 2), 552 (M-18-60, 8), 538(M-92, 6), 221 (10), 181 (33) (Ref. 0033/0037/0041)

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
TLC (silica plates, 0.5 mm, Kieselgel 60 Merck, hexane-acetone 7:3) Rf = 0.2 (Ref. 0033)
HPLC (column: LiChrosorb CN(7 mm) 0.4times25 cm, eluent: MeOH-acetone-hexane 1:10:89, flow: 1.5 ml/min) tR = 28 min (Ref. 0002/0003/0004)
HPLC (column: Ultrasphere 5CN 0.46times25 cm, eluent: hexane-isopropyl acetate-acetone-methnol 76:17:7:0.1, flow: 1.5 ml/min) tR = 11.39 min (Ref. 0033)
HPLC (column: Silica Spheri 0.46times25 cm, eluent: hexane-isopropyl acetate-acetone-methnol 76:17:7:0.1, flow: 2.0 ml/min) tR = 24.90 min (Ref. 0033)
SOURCE
Marine dinoflagellate (Gyrodinium resplendens, Amphidinium carterae, etc.) (Ref. 0039/0040/0042/0043)
Marine phytoplankton (Bacilliarophyceae, Dinophyceae, Prymnesiophyceae, Prasinophyceae, Chlorophyceae, Cryptophyceae, Rhodophyceae, Cyanophyceae) (Ref. 0034)
Sea squirt (Botrylloides violaceus) (Ref. 0041)
Sea anemone (Anemonia sulcata) (Ref. 0045)
CHEMICAL SYNTHESIS
The C22-allenic sulphone and the C15-5,6-epoxy-formyl ester were synthesized from the common starting meterial, (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone, in 13 and 12 steps, respectively. Rection with the formyl ester with the sulphone in the presence of LDA at -78degC provided peridinin accompanying with its 11'E-isomer.(Ref. 0001/0002/0031)
METABOLISM
Shell fish (Mytilus edulis): Peridinin a_right peridinoniol a_right pyrrhoxanthinol a_right Hydrate-pyrrhoxanthinol (Ref. 0404)
GENETIC INFORMATION

NOTE
Numbering and stereochemistry are revised (Ref. 1165).
REFERENCES
[0001]
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)
[TOP]

[0002]
AUTHOR:Yamano,Y. and Ito,M.
TITLE:First Total Synthesis of pm-Peridinin, pm-Pyrrhoxanthin and the Optically Active Peridinin
JOURNAL:J. Chem. Soc., Perkin Trans. 1
VOL: PAGE : 1599 -1610 (1993)
[TOP]

[0003]
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)
[TOP]

[0004]
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)
[TOP]

[0008]
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)
[TOP]

[0009]
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)
[TOP]

[0031]
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)
[TOP]

[0033]
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)
[TOP]

[0036]
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)
[TOP]

[0037]
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)
[TOP]

[0039]
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)
[TOP]

[0040]
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)
[TOP]

[0041]
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)
[TOP]

[0042]
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)
[TOP]

[0043]
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)
[TOP]

[0044]
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)
[TOP]

[0045]
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)
[TOP]

[0046]
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)
[TOP]

[0047]
AUTHOR:Johansen,J.E.,Borch.G., and Liaaen-Jensen,S.
TITLE:Chirality of peridinin and dinoxanthin
JOURNAL:Phytochemistry
VOL:19 PAGE : 441 -444 (1980)
[TOP]

[0097]
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)
[TOP]

[0217]
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)
[TOP]

[0221]
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)
[TOP]

[0222]
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)
[TOP]

[0404]
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)
[TOP]

[1114]
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)
[TOP]

[1165]
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)
[TOP]

[1167]
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)
[TOP]

[1269]
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)
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