Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products

Pierluigi Plastina, Cinzia Benincasa, Enzo Perri, Alessia Fazio, Giuseppina Augimeri, Mieke Poland, Renger Witkamp, Jocelijn Meijerink

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

Hydroxytyrosyl esters with short, medium and long acyl chains were evaluated for their ability to reduce nitric oxide (NO) production by lipopolysaccharide-stimulated RAW264.7 macrophages. Among the compounds tested, C18 esters, namely hydroxytyrosyl stearate (HtySte) and hydroxytyrosyl oleate (HtyOle), were found to decrease NO production in a concentration-dependent manner, while the other compounds, including the parent hydroxytyrosol, were ineffective in the tested concentration range (0.5–5 μM). Further study of the potential immune-modulating properties of HtyOle revealed a significant and concentration-dependent suppression of prostaglandin E2 production. At a transcriptional level, HtyOle inhibited the expression of inducible NO synthase, cyclooxygenase-2 and interleukin-1β. Moreover, HtyOle was identified for the first time in olive oil by-products by means of high performance liquid chromatography coupled with mass spectrometry. By contrast, HtyOle was not found in intact olives. Our results suggest that HtyOle is formed during oil processing and represents a significant form in which hydroxytyrosol occurs.

Original languageEnglish
Pages (from-to)105-113
JournalFood Chemistry
Volume279
DOIs
Publication statusPublished - 1 May 2019

Fingerprint

Oleic Acid
anti-inflammatory activity
olive oil
byproducts
oleic acid
Byproducts
Anti-Inflammatory Agents
Derivatives
nitric oxide
Nitric Oxide
Esters
esters
concentration of production
Stearates
Macrophages
interleukin-1
High performance liquid chromatography
Olea
Nitric Oxide Synthase Type II
prostaglandin synthase

Keywords

  • COX-2
  • Hydroxytyrosyl ester
  • Inflammation
  • Macrophages
  • NO
  • Olive mill waste water
  • Olive oil
  • PGE

Cite this

Plastina, Pierluigi ; Benincasa, Cinzia ; Perri, Enzo ; Fazio, Alessia ; Augimeri, Giuseppina ; Poland, Mieke ; Witkamp, Renger ; Meijerink, Jocelijn. / Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products. In: Food Chemistry. 2019 ; Vol. 279. pp. 105-113.
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abstract = "Hydroxytyrosyl esters with short, medium and long acyl chains were evaluated for their ability to reduce nitric oxide (NO) production by lipopolysaccharide-stimulated RAW264.7 macrophages. Among the compounds tested, C18 esters, namely hydroxytyrosyl stearate (HtySte) and hydroxytyrosyl oleate (HtyOle), were found to decrease NO production in a concentration-dependent manner, while the other compounds, including the parent hydroxytyrosol, were ineffective in the tested concentration range (0.5–5 μM). Further study of the potential immune-modulating properties of HtyOle revealed a significant and concentration-dependent suppression of prostaglandin E2 production. At a transcriptional level, HtyOle inhibited the expression of inducible NO synthase, cyclooxygenase-2 and interleukin-1β. Moreover, HtyOle was identified for the first time in olive oil by-products by means of high performance liquid chromatography coupled with mass spectrometry. By contrast, HtyOle was not found in intact olives. Our results suggest that HtyOle is formed during oil processing and represents a significant form in which hydroxytyrosol occurs.",
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Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products. / Plastina, Pierluigi; Benincasa, Cinzia; Perri, Enzo; Fazio, Alessia; Augimeri, Giuseppina; Poland, Mieke; Witkamp, Renger; Meijerink, Jocelijn.

In: Food Chemistry, Vol. 279, 01.05.2019, p. 105-113.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products

AU - Plastina, Pierluigi

AU - Benincasa, Cinzia

AU - Perri, Enzo

AU - Fazio, Alessia

AU - Augimeri, Giuseppina

AU - Poland, Mieke

AU - Witkamp, Renger

AU - Meijerink, Jocelijn

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N2 - Hydroxytyrosyl esters with short, medium and long acyl chains were evaluated for their ability to reduce nitric oxide (NO) production by lipopolysaccharide-stimulated RAW264.7 macrophages. Among the compounds tested, C18 esters, namely hydroxytyrosyl stearate (HtySte) and hydroxytyrosyl oleate (HtyOle), were found to decrease NO production in a concentration-dependent manner, while the other compounds, including the parent hydroxytyrosol, were ineffective in the tested concentration range (0.5–5 μM). Further study of the potential immune-modulating properties of HtyOle revealed a significant and concentration-dependent suppression of prostaglandin E2 production. At a transcriptional level, HtyOle inhibited the expression of inducible NO synthase, cyclooxygenase-2 and interleukin-1β. Moreover, HtyOle was identified for the first time in olive oil by-products by means of high performance liquid chromatography coupled with mass spectrometry. By contrast, HtyOle was not found in intact olives. Our results suggest that HtyOle is formed during oil processing and represents a significant form in which hydroxytyrosol occurs.

AB - Hydroxytyrosyl esters with short, medium and long acyl chains were evaluated for their ability to reduce nitric oxide (NO) production by lipopolysaccharide-stimulated RAW264.7 macrophages. Among the compounds tested, C18 esters, namely hydroxytyrosyl stearate (HtySte) and hydroxytyrosyl oleate (HtyOle), were found to decrease NO production in a concentration-dependent manner, while the other compounds, including the parent hydroxytyrosol, were ineffective in the tested concentration range (0.5–5 μM). Further study of the potential immune-modulating properties of HtyOle revealed a significant and concentration-dependent suppression of prostaglandin E2 production. At a transcriptional level, HtyOle inhibited the expression of inducible NO synthase, cyclooxygenase-2 and interleukin-1β. Moreover, HtyOle was identified for the first time in olive oil by-products by means of high performance liquid chromatography coupled with mass spectrometry. By contrast, HtyOle was not found in intact olives. Our results suggest that HtyOle is formed during oil processing and represents a significant form in which hydroxytyrosol occurs.

KW - COX-2

KW - Hydroxytyrosyl ester

KW - Inflammation

KW - Macrophages

KW - NO

KW - Olive mill waste water

KW - Olive oil

KW - PGE

U2 - 10.1016/j.foodchem.2018.12.007

DO - 10.1016/j.foodchem.2018.12.007

M3 - Article

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EP - 113

JO - Food Chemistry

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SN - 0308-8146

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