Purification and identification of linoleic acid hydroperoxides generated by soybean seed lipoxygenases 2 and 3

Hirotada Fukushige, Cunxi Wang, Thomas D. Simpson, Harold W. Gardner, David F. Hildebrand

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

It has been known that lipoxygenase (LOX) isozymes exhibit differences in product formation, but most product information to date is for LOX 1 among soybean (Glycine max) LOX isozymes. In this study, LOXs 2 and 3 were purified and used to generate hydroperoxide (HPOD) products in an in vitro system using linoleic acid as a substrate in the presence of either air or O2. The products were analyzed to determine their stereoisomeric characteristics. The control (no enzyme) showed only low levels of hydroperoxide production and no stereoisomeric specificity. LOX 2 shows high specificity in product formation, producing roughly 4 times more 13-HPOD than 9-HPOD, nearly all of which was 13-S(Z,E)-HPOD. LOX 3 produced more 9-HPOD than 13-HPOD at approximately a 2:1 ratio. No single stereoisomer was predominant among LOX 3 products. These results demonstrate that different isozymes of LOX have characteristic product profiles in in vitro reactions.

Original languageEnglish
Pages (from-to)5691-5694
Number of pages4
JournalJournal of Agricultural and Food Chemistry
Volume53
Issue number14
DOIs
StatePublished - Jul 13 2005

Keywords

  • Autoxidation
  • Glycine max
  • Linoleic acid hydroperoxide
  • Lipoxygenase
  • Soybean

ASJC Scopus subject areas

  • Chemistry (all)
  • Agricultural and Biological Sciences (all)

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