Structure related aggregation behavior of carotenoids and carotenoid esters

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 317, Issue , 2016, Pages 161-174

  Hempel, Judith ^a   Schädle, Christopher N ^a   Leptihn, Sebastian ^a   Carle, Reinhold ^a,b   Schweiggert, Ralf M ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Chirality; Computational modeling; Lycopene; Zeaxanthin; Carotene; Carotene

Indexed keywords

EID: 84949009784     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2015.10.024     Document Type: Article

References (44)

1. G. Britton, Overview of Carotenoid Biosynthesis, in: G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 3: Biosynthesis and Metabolism, Birkhäuser Verlag, Basel, Boston, Berlin, 1998, pp. 13-147.
2. G. Britton, S. Liaaen-Jensen, H. Pfander, Special Molecules, Special Properties, in: G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 4: Natural Functions, Birkhäuser Verlag, Basel, Boston, Berlin, 2008, pp. 1-6.
3. S. Köhn, H. Kolbe, M. Korger, C. Köpsel, B. Mayer, H. Auweter, E. Lüddecke, H. Bettermann, H.D. Martin, Aggregation and interface behaviour of carotenoids, in: G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 4: Natural Functions, Birkhäuser, Basel, Boston, Berlin, 2008, pp. 53-98.
4. M. Simonyi, Z. Bikádi, F. Zsila, and J. Deli Supramolecular exciton chirality of carotenoid aggregates Chirality 15 2003 680 698
5. F. Zsila, Z. Bikádi, Z. Keresztes, J. Deli, and M. Simonyi Investigation of the self-organization of lutein and lutein diacetate by electronic absorption, circular dichroism spectroscopy, and atomic force microscopy J. Phys. Chem. B 105 2001 9413 9421
6. T. Pullerits, S. Hess, J.L. Herek, and V. Sundström Temperature dependence of excitation transfer in LH2 of Rhodobacter sphaeroides J. Phys. Chem. B 101 1997 10560 10567
7. S. Kita, R. Fujii, R.J. Cogdell, and H. Hashimoto Characterization of fucoxanthin aggregates in mesopores of silica gel: electronic absorption and circular dichroism spectroscopies J. Photochem. Photobiol. A Chem. 313 2015 3 8
8. F.C. Spano Analysis of the UV/Vis and CD spectral line shapes of carotenoid assemblies: spectral signatures of chiral H-aggregates J. Am. Chem. Soc. 131 2009 4267 4278
9. C. Köpsel, H. Möltgen, H. Schuch, H. Auweter, K. Kleinermanns, H.D. Martin, and H. Bettermann Structure investigations on assembled astaxanthin molecules J. Mol. Struct. 750 2005 109 115
10. A.V. Ruban, P. Horton, and A.J. Young Aggregation of higher plant xanthophylls: differences in absorption spectra and in the dependency on solvent polarity J. Photochem. Photobiol. B Biol. 21 1993 229 234
11. F. Zsila, Z. Bikádi, J. Deli, and M. Simonyi Configuration of a single centre determines chirality of supramolecular carotenoid self-assembly Tetrahedron Lett. 42 2001 2561 2563
12. F. Zsila, Z. Bikádi, J. Deli, and M. Simonyi Chiral detection of carotenoid assemblies Chirality 13 2001 446 453
13. F. Zsila, J. Deli, Z. Bikádi, and M. Simonyi Supramolecular assemblies of carotenoids Chirality 13 2001 739 744
14. H.H. Billsten, V. Sundström, and T. Polívka Self-assembled aggregates of the carotenoid zeaxanthin: time-resolved study of excited states J. Phys. Chem. A 109 2005 1521 1529
15. P. Adamkiewicz, A. Sujak, and W.I. Gruszecki Spectroscopic study on formation of aggregated structures by carotenoids: role of water J. Mol. Struct. 1046 2013 44 51
16. Z. Bikádi, F. Zsila, J. Deli, G. Mády, and M. Simonyi The supramolecular structure of self-assembly formed by capsanthin derivatives Enantiomer 7 2002 67 76
17. R.E. Kopec, K.M. Riedl, E.H. Harrison, R.W. Curley Jr., D.P. Hruszkewycz, S.K. Clinton, and S.J. Schwartz Identification and quantification of apo-lycopenals in fruits, vegetables, and human plasma J. Agric. Food Chem. 58 2010 3290 3296
18. C.H. Eugster, Chemical Derivatization: Microscale Tests for the Presence of Common Functional Groups in Carotenoids, in: G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 1A: Isolation and Analysis, Birkhäuser, Basel, Boston, Berlin, 1995, pp. 71-80.
19. R.M. Schweiggert, C.B. Steingass, P. Esquivel, and R. Carle Chemical and morphological characterization of Costa Rican papaya (Carica papaya L.) hybrids and lines with particular focus on their genuine carotenoid profiles J. Agric. Food Chem. 60 2012 2577 2585
20. T. Polívka Effects of self-assembled aggregation on excited states J.T. Landrum, Carotenoids. Physical, Chemical, and Biological Functions and Properties 2010 CRC Boca Raton 137 157
21. N. Harada, Y. Takuma, and H. Uda Circular dichroic power due to chiral exciton coupling between two polyacene chromophores J. Am. Chem. Soc. 100 1978 4029 4036
22. F. Mo, X-ray crystallographic studies, in: G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 1B: Spectroscopy, Birkhäuser, Basel, Boston, Berlin, 1995, pp. 321-342.
23. Frank H. A., Christensen R. L., Excited electronic states, photochemistry and photophysics of carotenoids, in: G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 4: Natural Functions, Birkhäuser Verlag, Basel, Boston, Berlin, 2008, pp. 167-188.
24. G. Britton, UV/Visible Spectroscopy, in:G. Britton, S. Liaaen-Jensen, H. Pfander (Eds.), Carotenoids. Volume 1B: Spectroscopy, Birkhäuser Verlag, Basel, Boston, Berlin, 1995, pp. 13-62.
25. O. Wörz, and G. Scheibe On the reason for aggregation of dyes, the spectrum of photographic sensitization and biological activity Z. Naturforsch. B. 24 1969 381 390
26. Y. Mori, and Y. Mori Introductory studies on the growth and characterization of carotenoid solids: an approach to carotenoid solid engineering J. Raman Spectrosc. 32 2001 543 550
27. C. Köpsel Struktur von Carotinoidaggregaten - Spektroskopie und Modellierung von Polyenkomplexen in wäßrigen Lösungen, Ph.D. thesis 1999 Heinrich-Heine-Universität Düsseldorf
28. H. Auweter, H. Haberkorn, W. Heckmann, D. Horn, E. Lüddecke, J. Rieger, and H. Weiss Supramolecular structure of precipitated nanosize β-carotene particles Angew. Chem. Int. Ed. 38 1999 2188 2191
29. J. Milanowska, A. Polit, Z. Wasylewski, and W.I. Gruszecki Interactions of isomeric forms of xanthophyll pigment zeaxanthin with dipalmitoylphosphatidylcholine studied in monomolecular layers J. Photochem. Photobiol. B Biol. 72 2003 1 9
30. A. Ben-Amotz, A. Lers, and M. Avron Stereoisomers of β-carotene and phytoene in the alga Dunaliella bardawil Plant Physiol. 86 1988 1286 1291
31. A. Ben-Amotz, S. Mokady, S. Edelstein, and M. Avron Bioavailability of a natural isomer mixture as compared with synthetic all-trans-β-carotene in rats and chicks J. Nutr. 119 1989 1013 1019
32. J.L. Cooperstone, R.A. Ralston, K.M. Riedl, T.C. Haufe, R.M. Schweiggert, S.A. King, C.D. Timmers, D.M. Francis, G.B. Lesinski, S.K. Clinton, and S.J. Schwartz Enhanced bioavailability of lycopene when consumed as cis-isomers from tangerine compared to red tomato juice, a randomized, cross-over clinical trial Mol. Nutr. Food Res. 59 2015 658 669
33. J. Hempel, E. Amrehn, S. Quesada, P. Esquivel, V.M. Jiménez, A. Heller, R. Carle, and R.M. Schweiggert Lipid-dissolved γ-carotene, β-carotene, and lycopene in globular chromoplasts of peach palm (Bactris gasipaes Kunth) fruits Planta 240 2014 1037 1050
34. C. Wang, C.J. Berg, C.C. Hsu, B.A. Merrill, and M.J. Tauber Characterization of carotenoid aggregates by steady-state optical spectroscopy J. Phys. Chem. B 116 2012 10617 10630
35. A. Hager Formation of maxima in the absorption spectrum of carotenoids in the region around 370 nm; consequences for the interpretation of certain action spectra Planta 91 1970 38 53
36. Z. Bikádi, F. Zsila, J. Deli, G. Mády, and M. Simonyi The supramolecular structure of self-assembly formed by capsanthin derivatives Enantiomer 7 2002 67 76
37. P. Sitte Role of lipid self-assembly in subcellular morphogenesis O. Kiermayer, Cytomorphogenesis in Plants 1981 Springer New York 401 421
38. L. X.F. Wang, Z. Wang, Y. Wang, N. Wang, Z. Tamai, and J. Kido Hong Natural photosynthetic carotenoids for solution-processed organic bulk-heterojunction solar cells J. Phys. Chem. C 117 2013 804 811
39. H. Hug, M. Bader, P. Mair, and T. Glatzel Biophotovoltaics: natural pigments in dye-sensitized solar cells Appl. Energy 115 2014 216 225
40. O. Emter, H. Falk, and P. Sitte Specific carotenoids and proteins as prerequisites for chromoplast tubule formation Protoplasma 157 1990 128 135
41. R.M. Schweiggert, R.E. Kopec, M.G. Villalobos-Gutierrez, J. Högel, S. Quesada, P. Esquivel, S.J. Schwartz, and R. Carle Carotenoids are more bioavailable from papaya than from tomato and carrot in humans: a randomised cross-over study Br. J. Nutr. 111 2014 490 498
42. R.M. Schweiggert, D. Mezger, F. Schimpf, C.B. Steingass, and R. Carle Influence of chromoplast morphology on carotenoid bioaccessibility of carrot, mango, papaya, and tomato Food Chem. 135 2012 2736 2742
43. R.M. Schweiggert, and R. Carle Carotenoid deposition in plant and animal foods and its impact on bioavailability Crit. Rev. Food Sci. Nutr. 2015 10.1080/10408398.2015.1012756
44. H. Sliwka, T. Melø, B. Foss, S. Abdel-Hafez, V. Partali, G. Nadolski, H. Jackson, and S. Lockwood Electron- and energy-transfer properties of hydrophilic carotenoids Chem. Eur. J. 13 2007 4458 4466