A lipidomic platform establishment for structural identification of skin ceramides with non-hydroxyacyl chains

Jung Hoon Shin, Jong Cheol Shon, Kyohoon Lee, Sunki Kim, Chang Seo Park, Eung Ho Choi, Choong Hwan Lee, Hye Suk Lee, Kwang Hyeon Liu

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The stratum corneum (SC) is the outermost layer of skin that functions as a barrier and protects against environmental influences and transepidermal water loss. Its unique morphology consists of keratin-enriched corneocytes embedded in a distinctive mixture of lipids containing mainly ceramides, free fatty acids, and cholesterol. Ceramides are sphingolipids consisting of sphingoid bases, which are linked to fatty acids by an amide bond. Typical sphingoid bases in the skin are composed of dihydrosphingosine (dS), sphingosine (S), phytosphingosine (P), and 6-hydroxysphingosine (H), and the fatty acid acyl chains are composed of non-hydroxy fatty acid (N), α-hydroxy fatty acid (A), ω-hydroxy fatty acid (O), and esterified ω-hydroxy fatty acid (E). The 16 ceramide classes include several combinations of sphingoid bases and fatty acid acyl chains. Among them, N-type ceramides are the most abundant in the SC. Mass spectrometry (MS)/MS analysis of N-type ceramides using chip-based direct infusion nanoelectrospray-ion trap mass spectrometry generated the characteristic fragmentation pattern of both acyl and sphingoid units, which could be applied to structural identification of ceramides. Based on the MS/MS fragmentation patterns of N-type ceramides, comprehensive fragmentation schemes were proposed. In addition, mass fragmentation patterns, which are specific to the sphingoid backbone of N-type ceramides, were found in higher m/z regions of tandem mass spectra. These characteristic and general fragmentation patterns were used to identify N-type ceramides in human SC. Based on established MS/MS fragmentation patterns of N-type ceramides, 52 ceramides (including different classes of NS, NdS, NP, and NH) were identified in human SC. The MS/MS fragmentation patterns of N-type ceramides were characterized by interpreting their product ion scan mass spectra. This information may be used to identify N-type ceramides in the SC of human, rat, and mouse skin.

Original languageEnglish
Pages (from-to)1917-1932
Number of pages16
JournalAnalytical and Bioanalytical Chemistry
Volume406
Issue number7
DOIs
Publication statusPublished - 2014 Jan 1

Fingerprint

Ceramides
Skin
Mass spectrometry
Fatty Acids
Cornea
Tandem Mass Spectrometry
Hydroxy Acids
phytosphingosine
Ions
Sphingolipids
Sphingosine
Keratins
Nonesterified Fatty Acids
Amides
Rats
Mass Spectrometry

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry

Cite this

Shin, Jung Hoon ; Shon, Jong Cheol ; Lee, Kyohoon ; Kim, Sunki ; Park, Chang Seo ; Choi, Eung Ho ; Lee, Choong Hwan ; Lee, Hye Suk ; Liu, Kwang Hyeon. / A lipidomic platform establishment for structural identification of skin ceramides with non-hydroxyacyl chains. In: Analytical and Bioanalytical Chemistry. 2014 ; Vol. 406, No. 7. pp. 1917-1932.
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abstract = "The stratum corneum (SC) is the outermost layer of skin that functions as a barrier and protects against environmental influences and transepidermal water loss. Its unique morphology consists of keratin-enriched corneocytes embedded in a distinctive mixture of lipids containing mainly ceramides, free fatty acids, and cholesterol. Ceramides are sphingolipids consisting of sphingoid bases, which are linked to fatty acids by an amide bond. Typical sphingoid bases in the skin are composed of dihydrosphingosine (dS), sphingosine (S), phytosphingosine (P), and 6-hydroxysphingosine (H), and the fatty acid acyl chains are composed of non-hydroxy fatty acid (N), α-hydroxy fatty acid (A), ω-hydroxy fatty acid (O), and esterified ω-hydroxy fatty acid (E). The 16 ceramide classes include several combinations of sphingoid bases and fatty acid acyl chains. Among them, N-type ceramides are the most abundant in the SC. Mass spectrometry (MS)/MS analysis of N-type ceramides using chip-based direct infusion nanoelectrospray-ion trap mass spectrometry generated the characteristic fragmentation pattern of both acyl and sphingoid units, which could be applied to structural identification of ceramides. Based on the MS/MS fragmentation patterns of N-type ceramides, comprehensive fragmentation schemes were proposed. In addition, mass fragmentation patterns, which are specific to the sphingoid backbone of N-type ceramides, were found in higher m/z regions of tandem mass spectra. These characteristic and general fragmentation patterns were used to identify N-type ceramides in human SC. Based on established MS/MS fragmentation patterns of N-type ceramides, 52 ceramides (including different classes of NS, NdS, NP, and NH) were identified in human SC. The MS/MS fragmentation patterns of N-type ceramides were characterized by interpreting their product ion scan mass spectra. This information may be used to identify N-type ceramides in the SC of human, rat, and mouse skin.",
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A lipidomic platform establishment for structural identification of skin ceramides with non-hydroxyacyl chains. / Shin, Jung Hoon; Shon, Jong Cheol; Lee, Kyohoon; Kim, Sunki; Park, Chang Seo; Choi, Eung Ho; Lee, Choong Hwan; Lee, Hye Suk; Liu, Kwang Hyeon.

In: Analytical and Bioanalytical Chemistry, Vol. 406, No. 7, 01.01.2014, p. 1917-1932.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A lipidomic platform establishment for structural identification of skin ceramides with non-hydroxyacyl chains

AU - Shin, Jung Hoon

AU - Shon, Jong Cheol

AU - Lee, Kyohoon

AU - Kim, Sunki

AU - Park, Chang Seo

AU - Choi, Eung Ho

AU - Lee, Choong Hwan

AU - Lee, Hye Suk

AU - Liu, Kwang Hyeon

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AB - The stratum corneum (SC) is the outermost layer of skin that functions as a barrier and protects against environmental influences and transepidermal water loss. Its unique morphology consists of keratin-enriched corneocytes embedded in a distinctive mixture of lipids containing mainly ceramides, free fatty acids, and cholesterol. Ceramides are sphingolipids consisting of sphingoid bases, which are linked to fatty acids by an amide bond. Typical sphingoid bases in the skin are composed of dihydrosphingosine (dS), sphingosine (S), phytosphingosine (P), and 6-hydroxysphingosine (H), and the fatty acid acyl chains are composed of non-hydroxy fatty acid (N), α-hydroxy fatty acid (A), ω-hydroxy fatty acid (O), and esterified ω-hydroxy fatty acid (E). The 16 ceramide classes include several combinations of sphingoid bases and fatty acid acyl chains. Among them, N-type ceramides are the most abundant in the SC. Mass spectrometry (MS)/MS analysis of N-type ceramides using chip-based direct infusion nanoelectrospray-ion trap mass spectrometry generated the characteristic fragmentation pattern of both acyl and sphingoid units, which could be applied to structural identification of ceramides. Based on the MS/MS fragmentation patterns of N-type ceramides, comprehensive fragmentation schemes were proposed. In addition, mass fragmentation patterns, which are specific to the sphingoid backbone of N-type ceramides, were found in higher m/z regions of tandem mass spectra. These characteristic and general fragmentation patterns were used to identify N-type ceramides in human SC. Based on established MS/MS fragmentation patterns of N-type ceramides, 52 ceramides (including different classes of NS, NdS, NP, and NH) were identified in human SC. The MS/MS fragmentation patterns of N-type ceramides were characterized by interpreting their product ion scan mass spectra. This information may be used to identify N-type ceramides in the SC of human, rat, and mouse skin.

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