Human tear film and meibum. Very long chain wax esters and (O-acyl)-omega-hydroxy fatty acids of meibum

Igor A. Butovich, Jadwiga C. Wojtowicz, Mike Molai

Research output: Contribution to journalArticle

94 Citations (Scopus)

Abstract

Human meibum was targetly analyzed for the presence of intact wax esters (WEs) and related compounds by means of reverse-phase HPLC in combination with ion trap mass spectrometry. The major detected WEs were based on C18:n (n = 1-4) unsaturated FAs ranking in the following order of abundance: C18:1> C18:2> C18:3> C18:4. The major fatty alcohols (FAls) found in WE were of saturated nature and varied from C18:0 to C28:0. The three most abundant species were C18:1-FA esters of C24:0, C25:0, and C26:0-FAl. Typically, a major compound based on C18:1-FA and a saturated FAl was accompanied by a few related compounds based on a C18:2, C18:3, and C18:4-FA. Contrary to previous reports, no epoxy-WEs or epoxy-FAs were detected in fresh and 1-year-old meibum samples. More than 20 (O-acyl)-ω-hydroxy-FAs (OAHFAs) were observed. The main detected OAHFAs were based on very long-chain ω-hydroxy-FA (C30:1, C32:1, and C34:1) acylated through their ω-hydroxyls by a C18:1-FA. Due to their amphiphilic anionogenic nature, OAHFAs may be responsible for stabilization of the tear fi lm lipid layer by creating an interface between the vast pool of strictly nonpolar lipids of meibum (WEs, cholesteryl esters, etc.) and the aqueous subphase beneath it, a role previously attributed to phospholipids.

Original languageEnglish (US)
Pages (from-to)2471-2485
Number of pages15
JournalJournal of Lipid Research
Volume50
Issue number12
DOIs
StatePublished - Dec 1 2009

Fingerprint

Hydroxy Acids
Waxes
Tears
Esters
Fatty Acids
Fatty Alcohols
Lipids
Cholesterol Esters
Hydroxyl Radical
Mass spectrometry
Phospholipids
Stabilization
Ions
Mass Spectrometry
High Pressure Liquid Chromatography

Keywords

  • Dry eye epoxides
  • High pressure liquid chromatography
  • Ion trap mass spectrometry
  • Lipids
  • Meibomian gland secretions
  • Tear film lipid laver
  • Tears
  • Very long-chain fatty acids and alcohols

ASJC Scopus subject areas

  • Biochemistry
  • Cell Biology
  • Endocrinology

Cite this

Human tear film and meibum. Very long chain wax esters and (O-acyl)-omega-hydroxy fatty acids of meibum. / Butovich, Igor A.; Wojtowicz, Jadwiga C.; Molai, Mike.

In: Journal of Lipid Research, Vol. 50, No. 12, 01.12.2009, p. 2471-2485.

Research output: Contribution to journalArticle

@article{0578af4fa3df4283812cb30c360a1ae2,
title = "Human tear film and meibum. Very long chain wax esters and (O-acyl)-omega-hydroxy fatty acids of meibum",
abstract = "Human meibum was targetly analyzed for the presence of intact wax esters (WEs) and related compounds by means of reverse-phase HPLC in combination with ion trap mass spectrometry. The major detected WEs were based on C18:n (n = 1-4) unsaturated FAs ranking in the following order of abundance: C18:1> C18:2> C18:3> C18:4. The major fatty alcohols (FAls) found in WE were of saturated nature and varied from C18:0 to C28:0. The three most abundant species were C18:1-FA esters of C24:0, C25:0, and C26:0-FAl. Typically, a major compound based on C18:1-FA and a saturated FAl was accompanied by a few related compounds based on a C18:2, C18:3, and C18:4-FA. Contrary to previous reports, no epoxy-WEs or epoxy-FAs were detected in fresh and 1-year-old meibum samples. More than 20 (O-acyl)-ω-hydroxy-FAs (OAHFAs) were observed. The main detected OAHFAs were based on very long-chain ω-hydroxy-FA (C30:1, C32:1, and C34:1) acylated through their ω-hydroxyls by a C18:1-FA. Due to their amphiphilic anionogenic nature, OAHFAs may be responsible for stabilization of the tear fi lm lipid layer by creating an interface between the vast pool of strictly nonpolar lipids of meibum (WEs, cholesteryl esters, etc.) and the aqueous subphase beneath it, a role previously attributed to phospholipids.",
keywords = "Dry eye epoxides, High pressure liquid chromatography, Ion trap mass spectrometry, Lipids, Meibomian gland secretions, Tear film lipid laver, Tears, Very long-chain fatty acids and alcohols",
author = "Butovich, {Igor A.} and Wojtowicz, {Jadwiga C.} and Mike Molai",
year = "2009",
month = "12",
day = "1",
doi = "10.1194/jlr.M900252-JLR200",
language = "English (US)",
volume = "50",
pages = "2471--2485",
journal = "Journal of Lipid Research",
issn = "0022-2275",
publisher = "American Society for Biochemistry and Molecular Biology Inc.",
number = "12",

}

TY - JOUR

T1 - Human tear film and meibum. Very long chain wax esters and (O-acyl)-omega-hydroxy fatty acids of meibum

AU - Butovich, Igor A.

AU - Wojtowicz, Jadwiga C.

AU - Molai, Mike

PY - 2009/12/1

Y1 - 2009/12/1

N2 - Human meibum was targetly analyzed for the presence of intact wax esters (WEs) and related compounds by means of reverse-phase HPLC in combination with ion trap mass spectrometry. The major detected WEs were based on C18:n (n = 1-4) unsaturated FAs ranking in the following order of abundance: C18:1> C18:2> C18:3> C18:4. The major fatty alcohols (FAls) found in WE were of saturated nature and varied from C18:0 to C28:0. The three most abundant species were C18:1-FA esters of C24:0, C25:0, and C26:0-FAl. Typically, a major compound based on C18:1-FA and a saturated FAl was accompanied by a few related compounds based on a C18:2, C18:3, and C18:4-FA. Contrary to previous reports, no epoxy-WEs or epoxy-FAs were detected in fresh and 1-year-old meibum samples. More than 20 (O-acyl)-ω-hydroxy-FAs (OAHFAs) were observed. The main detected OAHFAs were based on very long-chain ω-hydroxy-FA (C30:1, C32:1, and C34:1) acylated through their ω-hydroxyls by a C18:1-FA. Due to their amphiphilic anionogenic nature, OAHFAs may be responsible for stabilization of the tear fi lm lipid layer by creating an interface between the vast pool of strictly nonpolar lipids of meibum (WEs, cholesteryl esters, etc.) and the aqueous subphase beneath it, a role previously attributed to phospholipids.

AB - Human meibum was targetly analyzed for the presence of intact wax esters (WEs) and related compounds by means of reverse-phase HPLC in combination with ion trap mass spectrometry. The major detected WEs were based on C18:n (n = 1-4) unsaturated FAs ranking in the following order of abundance: C18:1> C18:2> C18:3> C18:4. The major fatty alcohols (FAls) found in WE were of saturated nature and varied from C18:0 to C28:0. The three most abundant species were C18:1-FA esters of C24:0, C25:0, and C26:0-FAl. Typically, a major compound based on C18:1-FA and a saturated FAl was accompanied by a few related compounds based on a C18:2, C18:3, and C18:4-FA. Contrary to previous reports, no epoxy-WEs or epoxy-FAs were detected in fresh and 1-year-old meibum samples. More than 20 (O-acyl)-ω-hydroxy-FAs (OAHFAs) were observed. The main detected OAHFAs were based on very long-chain ω-hydroxy-FA (C30:1, C32:1, and C34:1) acylated through their ω-hydroxyls by a C18:1-FA. Due to their amphiphilic anionogenic nature, OAHFAs may be responsible for stabilization of the tear fi lm lipid layer by creating an interface between the vast pool of strictly nonpolar lipids of meibum (WEs, cholesteryl esters, etc.) and the aqueous subphase beneath it, a role previously attributed to phospholipids.

KW - Dry eye epoxides

KW - High pressure liquid chromatography

KW - Ion trap mass spectrometry

KW - Lipids

KW - Meibomian gland secretions

KW - Tear film lipid laver

KW - Tears

KW - Very long-chain fatty acids and alcohols

UR - http://www.scopus.com/inward/record.url?scp=70849130750&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70849130750&partnerID=8YFLogxK

U2 - 10.1194/jlr.M900252-JLR200

DO - 10.1194/jlr.M900252-JLR200

M3 - Article

VL - 50

SP - 2471

EP - 2485

JO - Journal of Lipid Research

JF - Journal of Lipid Research

SN - 0022-2275

IS - 12

ER -