Analytical and Bioanalytical Chemistry

, Volume 408, Issue 8, pp 2069–2082 | Cite as

Lipidomic platform for structural identification of skin ceramides with α-hydroxyacyl chains

  • Zhexue Wu
  • Jong Cheol Shon
  • Doohyun Lee
  • Kab-Tae Park
  • Chang Seo Park
  • Taeho Lee
  • Hye Suk Lee
  • Kwang-Hyeon Liu
Research Paper

Abstract

Skin ceramides are sphingolipids consisting of sphingoid bases, which are linked to fatty acids via an amide bond. Typical fatty acid acyl chains are composed of α-hydroxy fatty acid (A), esterified ω-hydroxy fatty acid (EO), non-hydroxy fatty acid (N), and ω-hydroxy fatty acid (O). We recently established a lipidomic platform to identify skin ceramides with non-hydroxyacyl chains using tandem mass spectrometry. We expanded our study to establish a lipidomic platform to identify skin ceramides with α-hydroxyacyl chains. Tandem mass spectrometry analysis of A-type ceramides using chip-based direct infusion nanoelectrospray-mass spectrometry showed the characteristic fragmentation pattern of both acyl and sphingoid units, which can be applied for structural identification of ceramides. Based on the tandem mass spectrometry fragmentation patterns of A-type ceramides, comprehensive fragmentation schemes were proposed. Our results may be useful for identifying A-type ceramides in the stratum corneum of human skin.

Keywords

Ceramide Mass spectrometry Skin lipid Stratum corneum 

Notes

Acknowledgments

This work was supported by a grant from the Bio & Medical Technology Development Program of the National Research Foundation (NRF) funded by the Ministry of Science, ICT & Future Planning (grant no. NRF-2015M3A9E1028326 and NRF-2014R1A2A2A01002582), and the Korea Healthcare Technology R&D Project, Ministry of Health and Welfare (grant no. HN13C0076), Republic of Korea. The authors have no other relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed. No writing assistance was utilized in the production of this manuscript.

Compliance with ethical standards

All individuals were enrolled with informed consent.

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

216_2015_9239_MOESM1_ESM.pdf (253 kb)
ESM 1 (PDF 151 kb)
216_2015_9239_MOESM2_ESM.xlsx (2.6 mb)
ESM 2 (XLSX 2694 kb)

References

  1. 1.
    Coderch L, Lopez O, de la Maza A, Parra JL. Ceramides and skin function. Am J Clin Dermatol. 2003;4:107–29.CrossRefGoogle Scholar
  2. 2.
    Huang HC, Chang TM. Ceramide 1 and ceramide 3 act synergistically on skin hydration and the transepidermal water loss of sodium lauryl sulfate-irritated skin. Int J Dermatol. 2008;47:812–9.CrossRefGoogle Scholar
  3. 3.
    Weerheim A, Ponec M. Determination of stratum corneum lipid profile by tape stripping in combination with high-performance thin-layer chromatography. Arch Dermatol Res. 2001;293:191–9.CrossRefGoogle Scholar
  4. 4.
    Mizutani Y, Mitsutake S, Tsuji K, Kihara A, Igarashi Y. Ceramide biosynthesis in keratinocyte and its role in skin function. Biochimie. 2009;91:784–90.CrossRefGoogle Scholar
  5. 5.
    Imokawa G, Akasaki S, Hattori M, Yoshizuka N. Selective recovery of deranged water-holding properties by stratum corneum lipids. J Invest Dermatol. 1986;87:758–61.CrossRefGoogle Scholar
  6. 6.
    Ishikawa J, Narita H, Kondo N, Hotta M, Takagi Y, Masukawa Y, et al. Changes in the ceramide profile of atopic dermatitis patients. J Invest Dermatol. 2010;130:2511–4.CrossRefGoogle Scholar
  7. 7.
    Janssens M, van Smeden J, Gooris GS, Bras W, Portale G, Caspers PJ, et al. Lamellar lipid organization and ceramide composition in the stratum corneum of patients with atopic eczema. J Invest Dermatol. 2011;131:2136–8.CrossRefGoogle Scholar
  8. 8.
    Imokawa G, Abe A, Jin K, Higaki Y, Kawashima M, Hidano A. Decreased level of ceramides in stratum corneum of atopic dermatitis: an etiologic factor in atopic dry skin? J Invest Dermatol. 1991;96:523–6.CrossRefGoogle Scholar
  9. 9.
    Lew BL, Cho Y, Kim J, Sim WY, Kim NI. Ceramides and cell signaling molecules in psoriatic epidermis: reduced levels of ceramides, PKC-alpha, and JNK. J Korean Med Sci. 2006;21:95–9.CrossRefGoogle Scholar
  10. 10.
    Motta S, Monti M, Sesana S, Caputo R, Carelli S, Ghidoni R. Ceramide composition of the psoriatic scale. Biochim Biophys Acta. 1993;1182:147–51.CrossRefGoogle Scholar
  11. 11.
    Masukawa Y, Narita H, Shimizu E, Kondo N, Sugai Y, Oba T, et al. Characterization of overall ceramide species in human stratum corneum. J Lipid Res. 2008;49:1466–76.CrossRefGoogle Scholar
  12. 12.
    t'Kindt R, Jorge L, Dumont E, Couturon P, David F, Sandra P, et al. Profiling and characterizing skin ceramides using reversed-phase liquid chromatography-quadrupole time-of-flight mass spectrometry. Anal Chem. 2012;84:403–11.CrossRefGoogle Scholar
  13. 13.
    Mutanu Jungersted J, Hellgren LI, Hogh JK, Drachmann T, Jemec GB, Agner T. Ceramides and barrier function in healthy skin. Acta Derm Venereol. 2010;90:350–3.CrossRefGoogle Scholar
  14. 14.
    Vietzke JP, Brandt O, Abeck D, Rapp C, Strassner M, Schreiner V, et al. Comparative investigation of human stratum corneum ceramides. Lipids. 2001;36:299–304.CrossRefGoogle Scholar
  15. 15.
    Thakoersing VS, van Smeden J, Mulder AA, Vreeken RJ, El Ghalbzouri A, Bouwstra JA. Increased presence of monounsaturated fatty acids in the stratum corneum of human skin equivalents. J Invest Dermatol. 2013;133:59–67.CrossRefGoogle Scholar
  16. 16.
    Uchida Y, Hara M, Nishio H, Sidransky E, Inoue S, Otsuka F, et al. Epidermal sphingomyelins are precursors for selected stratum corneum ceramides. J Lipid Res. 2000;41:2071–82.Google Scholar
  17. 17.
    Lee YS, Choi KM, Choi MH, Ji SY, Yoo JM, Lee YM, et al. Simultaneous HPLC analysis of ceramide and dihydroceramide in human hairs. Arch Pharm Res. 2009;32:1795–801.CrossRefGoogle Scholar
  18. 18.
    Yano M, Kishida E, Muneyuki Y, Masuzawa Y. Quantitative analysis of ceramide molecular species by high performance liquid chromatography. J Lipid Res. 1998;39:2091–8.Google Scholar
  19. 19.
    Samuelsson K, Sameulsson B. Gas chromatographic and mass spectrometric studies of synthetic and naturally occurring ceramides. Chem Phys Lipids. 1970;5:44–79.CrossRefGoogle Scholar
  20. 20.
    Joo KM, Nam GW, Park SY, Han JY, Jeong HJ, Lee SY, et al. Relationship between cutaneous barrier function and ceramide species in human stratum corneum. J Dermatol Sci. 2010;60:47–50.CrossRefGoogle Scholar
  21. 21.
    Farwanah H, Pierstorff B, Schmelzer CE, Raith K, Neubert RH, Kolter T, et al. Separation and mass spectrometric characterization of covalently bound skin ceramides using LC/APCI-MS and Nano-ESI-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;852:562–70.CrossRefGoogle Scholar
  22. 22.
    Han X, Gross RW. Shotgun lipidomics: electrospray ionization mass spectrometric analysis and quantitation of cellular lipidomes directly from crude extracts of biological samples. Mass Spectrom Rev. 2005;24:367–412.CrossRefGoogle Scholar
  23. 23.
    Heiskanen LA, Suoniemi M, Ta HX, Tarasov K, Ekroos K. Long-term performance and stability of molecular shotgun lipidomic analysis of human plasma samples. Anal Chem. 2013;85:8757–63.CrossRefGoogle Scholar
  24. 24.
    Shin JH, Shon JC, Lee K, Kim S, Park CS, Choi EH, et al. A lipidomic platform establishment for structural identification of skin ceramides with non-hydroxyacyl chains. Anal Bioanal Chem. 2014;406:1917–32.CrossRefGoogle Scholar
  25. 25.
    Han X. Characterization and direct quantitation of ceramide molecular species from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry. Anal Biochem. 2002;302:199–212.CrossRefGoogle Scholar
  26. 26.
    Hsu FF, Turk J, Stewart ME, Downing DT. Structural studies on ceramides as lithiated adducts by low energy collisional-activated dissociation tandem mass spectrometry with electrospray ionization. J Am Soc Mass Spectrom. 2002;13:680–95.CrossRefGoogle Scholar
  27. 27.
    Han X, Yang J, Cheng H, Ye H, Gross RW. Toward fingerprinting cellular lipidomes directly from biological samples by two-dimensional electrospray ionization mass spectrometry. Anal Biochem. 2004;330:317–31.CrossRefGoogle Scholar
  28. 28.
    Simons B, Kauhanen D, Sylvanne T, Tarasov K, Duchoslav E, Ekroos K. Shotgun lipidomics by sequential precursor ion fragmentation on a hybrid quadrupole time-of-flight mass spectrometer. Metabolites. 2012;2:195–213.CrossRefGoogle Scholar
  29. 29.
    Liebisch G, Drobnik W, Reil M, Trumbach B, Arnecke R, Olgemoller B, et al. Quantitative measurement of different ceramide species from crude cellular extracts by electrospray ionization tandem mass spectrometry (ESI-MS/MS). J Lipid Res. 1999;40:1539–46.Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  • Zhexue Wu
    • 1
  • Jong Cheol Shon
    • 1
  • Doohyun Lee
    • 1
  • Kab-Tae Park
    • 1
  • Chang Seo Park
    • 2
  • Taeho Lee
    • 1
  • Hye Suk Lee
    • 3
  • Kwang-Hyeon Liu
    • 1
  1. 1.BK21 Plus KNU Multi-Omics based Creative Drug Research Team, College of Pharmacy and Research Institute of Pharmaceutical SciencesKyungpook National UniversityDaeguRepublic of Korea
  2. 2.Department of Chemical and Biochemical EngineeringDongguk UniversitySeoulRepublic of Korea
  3. 3.College of Pharmacy and Integrated Research Institute of Pharmaceutical SciencesThe Catholic University of KoreaBucheonRepublic of Korea

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