Comparative and Stability Analyses of 9- and 13-Oxo-octadecadienoic Acids in Various Species of Tomato

TAKAHASHI, Haruya; KIM, Young-Il; HIRAI, Shizuka; GOTO, Tsuyoshi; OHYANE, Chie; TSUGANE, Taneaki; KONISHI, Chiaki; Fujii, Takashi; INAI, Shuji; IIJIMA, Yoko; AOKI, Koh; Shibata, Daisuke; Takahashi, Nobuyuki; KAWADA, Teruo

doi:10.1271/bbb.2012e2

Cited by 4 publications

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“…Furthermore, we compared the PPARα reporter activities in response to 13-oxo-ODA vs. 9-oxo-ODA ( Fig. 1A ), which is an isomer of 13-oxo-ODA [19] and acts as a PPARα activator [18] . Interestingly, the luciferase activity generated by 13-oxo-ODA was stronger than that of 9-oxo-ODA ( Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In mouse primary hepatocytes, 9-oxo-ODA enhanced fatty acid oxidation via PPARα activation and consequently inhibited triglyceride accumulation [18] . Interestingly, we developed that processed products such as tomato juice contain 13-oxo-9,11-octadecadenoic acid (13-oxo-ODA), an isomer of 9-oxo-ODA, which was not present in fresh tomato fruit [19] .…”

Section: Introductionmentioning

confidence: 99%

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Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice

et al. 2012

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Dyslipidemia is a major risk factor for development of several obesity-related diseases. The peroxisome proliferator-activated receptor α (PPARα) is a ligand-activated transcription factor that regulates energy metabolism. Previously, we reported that 9-oxo-10,12-octadecadienoic acid (9-oxo-ODA) is presented in fresh tomato fruits and acts as a PPARα agonist. In addition to 9-oxo-ODA, we developed that 13-oxo-9,11-octadecadienoic acid (13-oxo-ODA), which is an isomer of 9-oxo-ODA, is present only in tomato juice. In this study, we explored the possibility that 13-oxo-ODA acts as a PPARα agonist in vitro and whether its effect ameliorates dyslipidemia and hepatic steatosis in vivo. In vitro luciferase assay experiments revealed that 13-oxo-ODA significantly induced PPARα activation; moreover, the luciferase activity of 13-oxo-ODA was stronger than that of 9-oxo-ODA and conjugated linoleic acid (CLA), which is a precursor of 13-oxo-ODA and is well-known as a potent PPARα activator. In addition to in vitro experiment, treatment with 13-oxo-ODA decreased the levels of plasma and hepatic triglycerides in obese KK-Ay mice fed a high-fat diet. In conclusion, our findings indicate that 13-oxo-ODA act as a potent PPARα agonist, suggesting a possibility to improve obesity-induced dyslipidemia and hepatic steatosis.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice

et al. 2012

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“…Digestive samples and standard peptides were deproteinized with 50% acetonitrile and filtered through a 0.2 m PVDF membrane (Whatman, Brentford, UK) before analysis. An Acquity UPLC system (Waters, Milford, MA, USA) coupled to a Xevo quadrupole time-of-flight (QTOF) mass spectrometer (Waters) equipped with an electrospray ionization (ESI) source operating in positive-ion mode with a lock-spray interface for accurate mass measurements was used in the qualitative and quantitative analysis of peptides (13). Instrument control was performed using MassLynx 4.1 software (Waters).…”

Section: Quantitative Ultra-high-performance Liquid Chromatography-mamentioning

confidence: 99%

Characterization of Tyr‐Leu‐Gly, a novel anxiolytic‐like peptide released from bovine α _S ‐casein

et al. 2013

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We found previously that dipeptide YL exhibits orally active anxiolytic activity comparable to diazepam. The YL sequence is often observed in the primary structure of natural food proteins. In the present study, we investigated whether YL and YL analogues are released from bovine αS-casein by gastrointestinal proteases. YLG, corresponding to αS1-casein (aa 91-93), was more effectively released from αS-casein than YL by pepsin-pancreatin digestion, mimicking gastrointestinal enzymatic conditions. Using the synthetic model peptide, we determined that trypsin cleaved the N terminus of YLG, and elastase and carboxypeptidase contributed to cleave the C-terminus. YLG exhibited orally active anxiolytic-like activity in the elevated plus maze and open-field tests in mice. The anxiolytic-like activity of YLG was inhibited by WAY100135, SCH23390 or bicuculline, antagonists of serotonin 5-HT1A, dopamine D1, and GABA(A) receptors, respectively; however, YLG had no affinity for these receptors. The pepsin-pancreatin digest of αS-Casein also exhibited anxiolytic-like activity. Meanwhile, anxiolytic-like activity of α-casozepine, an αS1-casein-derived decapeptide with YL sequence in the N terminus, was blocked by WAY100135, SCH23390, or bicuculline, equally to YLG and YL; however, it was not detected in the pepsin-pancreatic digest. Taken together, we found that YLG is released after pepsin-pancreatic digestion of αS-casein and exhibits potent anxiolytic-like activity via activation of serotonin, dopamine, and the GABA receptor system.

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“…An Acuity ultra-high performance LC system (Waters, Milford, MA, USA) coupled to a Xevo quadrupole TOF mass spectrometer (Waters) equipped with an ESI source operating in positive ion mode with a lock-spray interface for accurate mass measurements was used in the qualitative and quantitative analyses of peptides (Mizushige et al, 2013a;Takahashi et al, 2011). The mobile phases consisted of 0.1% formic acid in water (solvent A) and 0.1% formic acid in ACN (solvent B).…”

Section: Peptide Quantification By Uplc-qtof-msmentioning

confidence: 99%

Antidepressant-like effect of food-derived pyroglutamyl peptides in mice

et al. 2015

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Comparative and Stability Analyses of 9- and 13-Oxo-octadecadienoic Acids in Various Species of Tomato

Cited by 4 publications

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Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice

Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice

Characterization of Tyr‐Leu‐Gly, a novel anxiolytic‐like peptide released from bovine α _S ‐casein

Antidepressant-like effect of food-derived pyroglutamyl peptides in mice

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Comparative and Stability Analyses of 9- and 13-Oxo-octadecadienoic Acids in Various Species of Tomato

Cited by 4 publications

References 0 publications

Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice

Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice

Characterization of Tyr‐Leu‐Gly, a novel anxiolytic‐like peptide released from bovine α S ‐casein

Antidepressant-like effect of food-derived pyroglutamyl peptides in mice

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Product

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Characterization of Tyr‐Leu‐Gly, a novel anxiolytic‐like peptide released from bovine α _S ‐casein