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11-Hydroperoxide eicosanoid-mediated 2(E),4(E)-decadienal production from arachidonic acid in the brown algae, Saccharina angustata

  • Kangsadan BoonprabEmail author
  • Kenji Matsui
  • Yoshihiko Akakabe
  • Norishige Yotsukura
  • Tadahiko Kajiwara
Article

Abstract

This work aims to propose a pathway for the production of 2(E),4(E)-decadienal from arachidonic acid (ARA) via 11-hydroperoxide eicosanoid (11 hydroperoxyeicosatetraenoic acid, 11-HPETE) through lipoxygenase (LOX) and hydroperoxide lyase (HPL) in the brown alga, Saccharina angustata, by identifying pathway intermediates through three studies. The first study investigated the biogeneration of 2(E),4(E)-decadienal in crude homogenates of fronds (CHF), while the second and third investigated whether ARA is the precursor of the pathway and if 11-HPETE is produced from ARA as an intermediate in 2(E),4(E)-decadienal generation, respectively. The results showed that 2(E),4(E)-decadienal was formed in CHF and its concentration increased after incubation. This finding led to the hypothesis that 2(E),4(E)-decadienal is formed enzymatically via LOX-HPL and consequently its biogeneration was determined. ARA was indicated to be a precursor of the pathway since, after CHF was incubated with ARA as a substrate, the amount of aldehyde increased significantly compared with that produced by CHF without ARA and without incubation. The production of 11-HPETE from ARA was also demonstrated as an intermediate reaction in 2(E),4(E)-decadienal formation via the LOX-HPL pathway. The hydroxy isomer of 11-HPETE was produced, and ARA was incubated with homogenated fronds in combination with glutathione peroxidase and glutathione to control its stability during identification. The compound was identified as 11-HPETE because the purified isomer showed the same retention time when co-injected with the standard using an HPLC technique; moreover, the same indicated mass spectrum was obtained as that of the standard via a GC/GCMS technique. The indicated pathway and the pathway for the production of short chain aldehydes [n-hexanal, 2(E),3(Z)-nonenal and 2(E),4(E)-decadienal] from ARA and linoleic acid through theirs hydroperoxides are proposed.

Keywords

Phaeophyta Saccharina angustata 2(E),4(E)-Decadienal 11 Hydroperoxyeicosatetraenoic acid Lipoxygenase Hydroperoxide lyase 

Notes

Funding information

This work was performed as part of the JSPS-NRCT Core University Program on the “Development of thermotolerant microbial resources and their applications”, with the cooperation of Japanese and Thai scientists and in association with Kasetsart University in Thailand and Yamaguchi University in Japan (1999-2010).

Supplementary material

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Fishery Products, Faculty of FisheriesKasetsart UniversityBangkokThailand
  2. 2.Department of Biological Chemistry, Faculty of AgricultureYamaguchi UniversityYamaguchiJapan
  3. 3.Field Science Center for Northern BiosphereHokkaido UniversitySapporoJapan

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