Skip to main content
SpringerLink
Log in

Mass Spectrometric Confirmation of γ-Linolenic Acid Ester-Linked Ceramide 1 in the Epidermis of Borage Oil Fed Guinea Pigs

  • Communication
  • Published:
Lipids

Abstract

Ceramide 1 (Cer1), a Cer species with eicosasphingenine (d20:1) amide-linked to two different ω-hydroxy fatty acids (C30wh:0:C32wh:1), which are, in turn, ester-linked to linoleic acid (LNA; 18:2n-6), plays a critical role in maintaining the structural integrity of the epidermal barrier. Prompted by the recovery of a disrupted epidermal barrier with dietary borage oil [BO: 36.5 % LNA and 23.5 % γ-linolenic acid (GLA; 18:3n-6)], in essential fatty acid (EFA)-deficient guinea pigs, we further investigated the effects of BO on the substitution of ester-linked GLA for LNA in these two epidermal Cer1 species by LC–MS in positive and negative modes. Dietary supplementation of BO for 2 weeks in EFA-deficient guinea pigs increased LNA ester-linked to C32wh:1/d20:1 and C30wh:0/d20:1 of Cer1. Moreover, GLA ester-linked to C32wh:1/d20:1, but not to C30wh:0/d20:1, of Cer1 was detected, which was further confirmed by the product ions of m/z 277.2 for ester-linked GLA and m/z 802.3 for the deprotonated C32wh:1/d20:1. C20-Metabolized fatty acids of LNA or GLA were not ester-linked to these Cer1 species. Dietary BO induced GLA ester-linked to C32wh:1/d20:1 of epidermal Cer1.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Abbreviations

EFA:

Essential fatty acid

BO:

Borage oil

Cer1:

Ceramide 1

GLA:

γ-Linolenic acid (18:3n-6)

FA:

Fatty acid

HCO:

Hydrogenated coconut oil

LNA:

Linoleic acid (18:2n-6)

LC:

Liquid chromatography

LC–ESI–MS/MS:

Liquid chromatography coupled with electrospray tandem mass spectrometry

m/z :

Mass/charge

MS:

Mass spectrometry

References

  1. Holleran WM, Takagi Y, Uchida Y (2006) Epidermal sphingolipids: metabolism, function, and roles in skin disorders. FEBS Lett 580:5456–5466

    Article  CAS  PubMed  Google Scholar 

  2. Bouwstra JA, Gooris GS, Dubbelaar FER, Weerheim AM, Ijzerman AP, Ponec M (1998) Role of ceramide 1 in the molecular organization of the stratum corneum lipids. J Lipid Res 39:186–196

    CAS  PubMed  Google Scholar 

  3. Bouwstra JA, Ponec M (2006) The skin barrier in healthy and diseased state. Biochim Biophys Acta 1758:2080–2095

    Article  CAS  PubMed  Google Scholar 

  4. Wertz PW, Cho ES, Downing DT (1983) Effects of essential fatty acid deficiency on the epidermal sphingolipids of the rat. Biochim Biophys Acta 753:350–355

    Article  CAS  PubMed  Google Scholar 

  5. Foster RH, Hardy G, Alany RG (2010) Borage oil in the treatment of atopic dermatitis. Nutrition 26:708–718

    Article  CAS  PubMed  Google Scholar 

  6. Chung S, Kong S, Seong K, Cho Y (2002) γ-Linolenic acid in borage oil reverses epidermal hyperproliferation in guinea pigs. J Nutr 132:3090–3097

    CAS  PubMed  Google Scholar 

  7. Ziboh VA, Miller CC, Cho Y (2000) Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr 71(suppl):361S–366S

    CAS  PubMed  Google Scholar 

  8. Mohrhauer H, Holman RT (1963) The effect of dose level of essential fatty acids upon fatty acid composition of the rat liver. J Lipid Res 4:151–159

    CAS  PubMed  Google Scholar 

  9. Merrill AH Jr, Sullards MC, Allegood JC, Kelly S, Wang E (2005) Sphingolipidomics: high-throughput, structure-specific, and quantitative analysis of sphingolipids by liquid chromatography tandem mass spectrometry. Methods 36:207–224

    Article  CAS  PubMed  Google Scholar 

  10. Hinder A, Schmelzer CEH, Rawlings AV, Neubert RHH (2011) Investigation of the molecular structure of the human stratum corneum ceramides (NP) and (EOS) by mass spectrometry. Skin Pharmacol Physiol 24:127–135

    Article  CAS  PubMed  Google Scholar 

  11. Hamaka S, Hara M, Nishio H, Otsuka F, Suzuki A, Uchida Y (2002) Human epidermal glycosylceramides are major precursors of stratum corneum ceramides. J Invest Dermatol 119:416–423

    Article  Google Scholar 

  12. Hansen HS, Jensen B (1985) Essential function of linoleic acid esterified in acylglucosylceramide and acylceramide in maintaining the epidermal water permeability barrier. Evidence from feeding studies with oleate, linoleate, arachidonate, columbinate and alpha-linolenate. Biochim Biophys Acta 834:357–363

    Article  CAS  PubMed  Google Scholar 

  13. Ponec M, Weerheim A, Lankhorst P, Wertz P (2003) New acylceramide in native and reconstructed epidermis. J Invest Dermatol 120:581–588

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This study was supported by a grant of the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea (Grant No.: HN13C0076).

Author information

Authors and Affiliations

  1. College of Pharmacy, Chungbuk National University, Cheongju, Korea

    Kyong-Oh Shin, Cho-Hee Seo & Yong-Moon Lee

  2. Department of Medical Nutrition, Graduate School of East–West Medical Science, Kyung Hee University, Yongin-Si, Gyeonggi-do, Korea

    Kunpyo Kim, Sanghun Jeon & Yunhi Cho

Authors
  1. Kyong-Oh Shin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kunpyo Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sanghun Jeon
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Cho-Hee Seo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yong-Moon Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yunhi Cho
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yunhi Cho.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shin, KO., Kim, K., Jeon, S. et al. Mass Spectrometric Confirmation of γ-Linolenic Acid Ester-Linked Ceramide 1 in the Epidermis of Borage Oil Fed Guinea Pigs. Lipids 50, 1051–1056 (2015). https://doi.org/10.1007/s11745-015-4056-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-015-4056-2

Keywords

Search

Navigation