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Formation of cleavage products by autoxidation of lycopene

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Lipids

Abstract

The cleavage products formed by autoxidation of lycopene were evaluated in order to elucidate possible oxidation products of lycopene in biological tissues. Lycopene solubilized at 50 μM in toluene, aqueous Tween 40, or liposomal suspension was oxidized by incubating at 37°C for 72 h. Among a number of oxidation products formed, eight products in the carbonyl compound fraction were identified as 3,7,11-trimethyl-2,4,6,10-dodecatetraen-1-al, 6,10,14-trimethyl-3,5,7,9,13-pentadecapentaen-2-one, acycloretinal, apo-14′-lycopenal, apo-12′-lycopenal, apo-10′-lycopenal, apo-8′-lycopenal, and apo-6′-lycopenal. These correspond to a series of products formed by cleavage in the respective 11 conjugated double bonds of lycopene. The maximal formation of acycloretinal was 135 nM in toluene, 49 nM in aqueous Tween 40, and 64 nM in liposomal suspension. Acycloretinoic acid was also formed by autoxidation of lycopene, although its formation was lower in the aqueous media than in toluene. The pig liver homogenate had the ability to convert acycloretinal to acycloretinoic acid, comparable to the conversion of all-trans-retinal to all-trans-retinoic acid. These results suggest that lycopene might be cleaved to a series of apolycopenals and short-chain carbonyl compounds under the oxidative conditions in biological tissues and that acycloretinal is further enzymatically converted to acycloretinoic acid.

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Abbreviations

GC-MS:

gas chromatography-mass spectrometry

HPLC:

high-performance liquid chromatography

NMR:

nuclear magnetic resonance

RAR:

retinoic acid receptor

RXR:

retinoid X response

UV-VIS:

ultraviolet-visible

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Author notes

  1. Seon-Jae Kim

    Present address: Food Industrial Technology Research Center, Mokpo National University, 534-729, Chonnam, Korea

Authors and Affiliations

  1. Ministry of Agriculture, Forestry and Fisheries, National Food Research Institute, Kannondai 2-1-2, Tsukuba, 305-8642, Ibarak, Japan

    Seon-Jae Kim, Eiichi Nara, Hidetaka Kobayashi & Akihiko Nagao

  2. Department of Nutrition, School of Medicine, The University of Tokushima, 770-0042, Tokushima, Japan

    Junji Terao

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  1. Seon-Jae Kim
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  2. Eiichi Nara
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Correspondence to Akihiko Nagao.

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Kim, SJ., Nara, E., Kobayashi, H. et al. Formation of cleavage products by autoxidation of lycopene. Lipids 36, 191–200 (2001). https://doi.org/10.1007/s11745-001-0706-8

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  • DOI: https://doi.org/10.1007/s11745-001-0706-8

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