Some Analytical Observations of Autoxidation Products of Linoleic Acid and Their Thiobarbituric Acid Reactive Substances

Kanazawa, Kazuki; Danno, Gen-ichi; Natake, Masato

doi:10.1080/00021369.1983.10865903

Cited by 5 publications

(4 citation statements)

References 9 publications

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“…3), the first peak giving major fragment ionsofm/z 186, 168, 158, 155and 143, andthe second peak of m/z 217, 185, 152 and 143. These fragmentations agreed completely with those of methylated 9-ONA23) and nonanedioic acid (NDA), 13) respectively.…”

Section: Resultssupporting

confidence: 69%

The induction of lipid peroxidation in rat liver by oral intake of 9-oxononanoic acid contained in autoxidized linoleic acid.

MINAMOTO¹,

Kanazawa

ASHIDA³

et al. 1985

Agricultural and Biological Chemistry

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A component in the autoxidation products oflinoleic acid (LA) which induced the endogenous lipid peroxidation was searched for. Secondary autoxidation products (SP) of LA induced the production of thiobarbituric acid reactive substances (TBARS) in liver as well as the LA hydroperoxides stimulated. SP were separated chromatographically into some fractions which were administered orally to rats. One fraction composed mainly of 9-oxononanoic acid (9-ONA) markedly stimulated the TBARSproduction in liver. Authentic 9-ONA also increased the lipid peroxide level as determined by a new test, as well as the activities of glutathione peroxidase and reductase in liver. Thus, hepatic lipid peroxidation was induced by orally given 9-ONAwhich was present in the autoxidation products of LA.Polyunsaturated fatty acids react easily with atmospheric oxygen and are autoxidized.1* The autoxidation products occur in our daily food, although their amounts may not be high.These products may induce endogenous lipid peroxidation, endogenous lipid peroxides having often been the cause of serious diseases2 ~5) and senescence.6~9) Kanazawa et al.l0) have reported that radioactive substances of [U-14C]SP which was orally given accumulated in liver (accounting for 2.6%) between 12 ~24 hr, and that the hepatic lipid peroxide content then remained at a high level after the radioactivity had disappeared. In nutrition, the identification of inducers of endogenous lipid peroxidation contained in autoxidation products that are orally given is important.11}

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Section: Resultssupporting

confidence: 69%

The induction of lipid peroxidation in rat liver by oral intake of 9-oxononanoic acid contained in autoxidized linoleic acid.

MINAMOTO¹,

Kanazawa

ASHIDA³

et al. 1985

Agricultural and Biological Chemistry

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“…Pryor et al (1976) proposed a mechanism that explained more adequately the reason autoxidized dienes produced very little malondialdehyde (MDA) compared to autoxidized trienes. Other researchers (Kanazawa et al, 1983;Pearson et al, 1983) have reported that MDA was not a main product nor a major thiobarbituric acid reactive substance during autoxidation of linoleic acid. The fact that each isomer of methyl arachidonate monohydroperoxide is capable of yielding TEARS (Terao and Matsushita, 1981) leaves open the possibility that each molecule of fatty acid with four or more methylene double bonds may produce two molecules of MDA.…”

Section: Resultsmentioning

confidence: 92%

Thiobarbituric acid reactive substance formation as affected by distribution of polyenoic fatty acids in individual phospholipids

Pikul¹,

Kummerow²

1991

J. Agric. Food Chem.

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“…These compounds were found to be odor-active ( Table 3 ), which likely facilitated olfactory discrimination between the fatty acid solutions and the mineral oil. The alcohols and aldehydes are well-known oxidation products of fatty acids ( Frankel et al 1981 ; Kanazawa et al 1983 ). Cao et al (2014) suggested that several aldehydes, such as octanal, nonanal, decanal, and 2-decenal, could serve as oxidation indicators for oleic acid, while hexanal was closely associated with the oxidation of linoleic acid.…”

Section: Discussionmentioning

confidence: 99%

Can humans smell tastants?

Mu,

Stieger,

Boesveldt

2024

Chemical Senses

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Although studies have shown that olfaction may contribute to the perception of tastant, literature is scarce or circumstantial, especially in humans. This study aims to (a) explore whether humans can perceive solutions of basic prototypical tastants through orthonasal and retronasal olfaction, (b) and to examine what volatile odor compounds (VOCs) underlie this ability. Solutions of five basic tastants (sucrose, sodium chloride, citric acid, monosodium glutamate (MSG), quinine dissolved in water, and two fatty acids (oleic and linoleic acid dissolved in mineral oil were prepared. Triangle discrimination tests were performed (n=41 in duplicate) to assess whether the tastant solutions can be distinguished from blanks (solvents) though ortho- and retronasal olfaction. Participants were able to distinguish all tastant solutions from blank through orthonasal olfaction. Only sucrose, sodium chloride, oleic acid, and linoleic acid were distinguished from blank by retronasal olfaction. Ethyl dichloroacetate, methylene chloride, and/or acetone were identified in the headspace of sucrose, MSG and quinine solutions but not in the headspace of water, sodium chloride and citric acid solutions. Fat oxidation compounds such as alcohols and aldehydes were detected in the headspace of the oleic and linoleic acid solutions but not the mineral oil. We conclude that prototypical tastant solutions can be discriminated from water and fatty acid solutions from mineral oil through orthonasal olfaction. Differences in the volatile headspace composition between blanks and tastant solutions may have facilitated the olfactory discrimination. These findings can have methodological implications for future studies assessing gustatory perception using these prototypical taste compounds.

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Some Analytical Observations of Autoxidation Products of Linoleic Acid and Their Thiobarbituric Acid Reactive Substances

Cited by 5 publications

References 9 publications

The induction of lipid peroxidation in rat liver by oral intake of 9-oxononanoic acid contained in autoxidized linoleic acid.

The induction of lipid peroxidation in rat liver by oral intake of 9-oxononanoic acid contained in autoxidized linoleic acid.

Thiobarbituric acid reactive substance formation as affected by distribution of polyenoic fatty acids in individual phospholipids

Can humans smell tastants?

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