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Carotenoids, Novel Polyene Polyketones and New Capsorubin Isomers as Efficient Quenchers of Singlet Molecular Oxygen

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Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications

Part of the book series: Molecular and Cell Biology Updates ((MCBU))

Summary

The singlet molecular oxygen (1O2) quenching activity of carotenoids and newly synthesized polyene polyketones and capsorubin isomers was examined using the thermodissociable endoperoxide of 3,3′-(1,4-naphthylene) dipropionate (NDPO2) as 1O2 source and a germanium diode to monitor 1O2 photoemission. C28-polyenetetrone (1) exhibits the highest physical quenching rate constant with 1O2 (kq = 16 × 109 M-441s-1). For comparison, the rate constant for the most efficient biological carotenoid, lycopene (3) is kq = 9 × 109 M-1s-1 and that of β-carotene (5) kq = 9 × 109 M-1s-1. The presence of two oxalyl chromophores at the ends of the polyene chain seems to enhance the 1O2 quenching ability in the C28 -polyene-tetrone (1). C28-polyene-tetrone-diacetal (2) (kq = 9 × 109 M-1 s-1) and C40-epiisocapsorubin (4) (kq = 8 × 109 M-1 s-1) also have high 1O2 quenching abilities.

Due to the high singlet oxygen quenching abilities, C28-polyene-tetrone (1), C28-polyene-tetrone-diacetal (2) and C40-epiisocapsorubin (4) may have potential use in preventing 1O2-induced damage in biological and nonbiological systems.

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Authors and Affiliations

  1. Institut fur Physiologische Chemie I, Universitat Dusseldorf, Dusseldorf, Germany

    Thomas P. A. Devasagayam & Helmut Siesa

  2. Institut fur Organische Chemie und Makromolekulare Chemie I, Universitat Dusseldorf, Dusseldorf, Germany

    Hans Ippendorf, Thomas Werner & Hans Dieter Martin

Authors
  1. Thomas P. A. Devasagayam
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  2. Hans Ippendorf
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  3. Thomas Werner
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  4. Hans Dieter Martin
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  5. Helmut Siesa
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Editor information

Editors and Affiliations

  1. Malaysian Palm Oil Promotion Council, Bangunan Getah Asli 148 Jalan Ampang, 50450, Kuala Lumpur, Malaysia

    A. S. H. Ong

  2. Dept. of Molecular and Cell Biology 251 Life Science Addition, Membrane Bioenergetics Group, Berkeley, California, 94720, USA

    L. Packer

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© 1992 Birkhäuser Verlag, Basel/Switzerland

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Devasagayam, T.P.A., Ippendorf, H., Werner, T., Martin, H.D., Siesa, H. (1992). Carotenoids, Novel Polyene Polyketones and New Capsorubin Isomers as Efficient Quenchers of Singlet Molecular Oxygen. In: Ong, A.S.H., Packer, L. (eds) Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications. Molecular and Cell Biology Updates. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-7432-8_21

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  • DOI: https://doi.org/10.1007/978-3-0348-7432-8_21

  • Publisher Name: Birkhäuser Basel

  • Print ISBN: 978-3-0348-7434-2

  • Online ISBN: 978-3-0348-7432-8

  • eBook Packages: Springer Book Archive

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