Skip to main content

Biosynthetic Oils, Fats, Terpenes, Sterols, Waxes: Analytical Methods, Diversity, Characteristics

  • Reference work entry

Abstract:

In the last century water distillation, the method of choice for many centuries to extract hydrophilic compounds from complex biological matrices, was more and more replaced by various chromatographic methods. At the same time chemical degradation steps to elucidate the structure of the compounds were replaced by physical methods. The current development goes to hyphenated instruments where multi-dimensional separations are combined with the subsequent structure elucidation of the individual compounds. The considerable improvements achieved in the analytical field led to the discovery and characterization of compounds never recognized before and allowed new insights in chemical ecology. Although essential oils, fats and waxes have been used for thousands of years, their main compositions have been revealed only in the last two centuries. Today more than 50,000 terpenes and about the same number of hydrocarbons are known. Since more sophisticated analytical instruments with higher sensitivities and resolutions become available each year their numbers are still increasing. With the growing numbers of compounds available new applications in various fields are realized. Although still in its infancy, this also includes a deeper understanding of the ecological functions of these hydrophobic compounds, which in itself presents many novel applications.

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

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   1,499.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD   549.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  • Abraham W-R (2001) Bioactive sesquiterpenes produced by fungi: are they useful for humans as well? Curr Med Chem 8: 583–606.

    PubMed  CAS  Google Scholar 

  • Abraham W-R, Knoch I, Witte L (1990) Biosynthesis of the terpenoidic polyketide fusalanipyrone Phytochemistry. 29: 2877–2878.

    Article  CAS  Google Scholar 

  • Barry III CE, Lee RE, Mdluli K, Sampson AE, Schroeder BG, Slayden RA, Yuan Y (1998) Mycolic acids: structure, biosynthesis and physiological functions. Prog Lipid Res 37: 143–179.

    Article  PubMed  CAS  Google Scholar 

  • Bentley R (2006) The nose as a stereochemist. Enantiomers and odor. Chem Rev 106: 4099–4112.

    Article  PubMed  CAS  Google Scholar 

  • Berger TA (1996) Separation of a gasoline on an open tubular column with 1.3 million effective plates. Chromatographia 42: 63–71.

    Article  CAS  Google Scholar 

  • Bhosale P, Bernstein PS (2005) Microbial xanthophylls. Appl Microbiol Biotechnol 68: 445–455.

    Article  PubMed  CAS  Google Scholar 

  • Bicchi C, Cordero C, Liberto E, Rubiolo P, Sgorbini B (2004) Automated headspace solid-phase dynamic extraction to analyse the volatile fraction of food matrices. J Chromatogr A 1024: 217–226.

    Article  PubMed  CAS  Google Scholar 

  • Bicchi C, D’Amato A, Rubiolo P (1999) Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oil, aroma and flavour fields. J Chromatogr A 843: 99–121.

    Article  PubMed  CAS  Google Scholar 

  • Blomberg J, Schoenmakers PJ, Brinkman UAT (2002) Gas chromatographic methods for oil analysis. J Chromatogr A 972: 137–173.

    Article  PubMed  CAS  Google Scholar 

  • Bowman JP, McCammon SA, Nichols DS, Skerratt JH, Rea SM, Nichols PD, McMeekin TA (1997) Shewanella gelidimarina. sp. nov. and Shewanella frigidimarina sp. nov., novel Antarctic species with the ability to produce eicosapentaenoic acid (20:5 omega 3) and grow anaerobically by dissimilatory Fe(III) reduction. Int J Syst Bacteriol 47: 1040–1047.

    Article  PubMed  CAS  Google Scholar 

  • Brondz I (2002) Development of fatty acid analysis by high-performance liquid chromatography, gas chromatography, and related techniques. Anal Chim Acta 465: 1–37.

    Article  CAS  Google Scholar 

  • Butler WR, Guthertz LS (2001) Mycolic acid analysis by high-performance liquid chromatography for identification of Mycobacterium. species. Clin Microbiol Rev 14: 704–726.

    Article  PubMed  CAS  Google Scholar 

  • Byrdwell WC (2001) Atmospheric pressure chemical ionization mass spectrometry for analysis of lipids. Lipids 36: 327–346.

    Article  PubMed  CAS  Google Scholar 

  • Chernushevich IV, Loboda AV, Thomson BA (2001) An introduction to quadrupole/time-of-flight mass spectrometry. J Mass Spectrom 36: 849–865.

    Article  PubMed  CAS  Google Scholar 

  • Delong EF, King LL, Massana R, Cittone H, Murray A, Schleper C, Wakeham SG (1998) Dibiphytanyl ether lipids in nonthermophilic Crenarchaeotes. Appl Environ Microbiol 64: 1133–1138.

    PubMed  CAS  Google Scholar 

  • Dembitsky VM (2006) Anticancer activity of natural and synthetic acetylenic lipids. Lipids 41: 883–924.

    Article  PubMed  CAS  Google Scholar 

  • Dembitsky, VM, Srebnik M (2002) Natural halogenated fatty acids: their analogues and derivatives. Prog Lipid Res 41: 315–367.

    Article  PubMed  CAS  Google Scholar 

  • Demeestere K, Dewulf J, De Witte B, Van Langenhove H (2007) Sample preparation for the analysis of volatile organic compounds in air and water matrices. J Chromatogr A 1153: 130–144.

    Article  PubMed  CAS  Google Scholar 

  • Dicke M, van Beek TA, Posthumus MA, Ben Dom N, van Bokhoven H, de Groot AE (1990) Isolation and identification of volatile kairomone that affects acarine predator-prey interactions. Involvement of host plant in its production. J Chem Ecol 16: 381–396.

    Article  CAS  Google Scholar 

  • Dictionary of Natural Compounds (2008) Chapman and Hall Chemical Database.

    Google Scholar 

  • Dietz C, Sanz J, Cámara C (2006) Recent developments in solid-phase microextraction coatings and related techniques. J Chromatogr A 1103: 183–192.

    Article  PubMed  CAS  Google Scholar 

  • Eyres G, Marriott PJ, Dufour JP (2006) The combination of gas chromatography-olfactometry and multidimensional gas chromatography for the characterisation of essential oils. J Chromatogr A 1150: 70–77.

    Article  PubMed  Google Scholar 

  • Feng X, Siegel MM (2007) FTICR-MS applications for the structure determination of natural products. Anal Bioanal Chem 389: 1341–1363.

    Article  PubMed  CAS  Google Scholar 

  • Friedman L, Miller GJ (1971) Odor incongruity and chirality. Science 172: 1044–1046.

    Article  PubMed  CAS  Google Scholar 

  • Furr HC (2004) Analysis of retinoids and carotenoids: problems resolved and unsolved. J Nutr 134: 281S–285S.

    PubMed  CAS  Google Scholar 

  • Gershenzon J, Dudareva N (2007) The function of terpene natural products in the natural world. Nat Chem Biol 3: 408–414.

    Article  PubMed  CAS  Google Scholar 

  • Goldstein AH, Galbally IE (2007) Known and unexplored organic constituents in the Earth’s atmosphere. Environ Sci Technol 41: 1514–1521.

    Article  PubMed  CAS  Google Scholar 

  • Griffiths WJ (2003) Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids. Mass Spectrom Rev 22: 81–152.

    Article  PubMed  CAS  Google Scholar 

  • Gübitz G, Schmid MG (2006) Chiral separation principles in chromatographic and electromigration techniques. Mol Biotechnol 32: 159–180.

    Article  PubMed  Google Scholar 

  • Harborne JB (2001) Twenty-five years of chemical ecology. Nat Prod Rep 18: 361–379.

    Article  PubMed  CAS  Google Scholar 

  • Hoye TR, Jeffrey CS, Shao F (2007) Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons. Nat Protoc 2: 2451–2458.

    Article  PubMed  CAS  Google Scholar 

  • Hu LH, Sim KY (1999) Cytotoxic polyprenylated benzoylphloroglucinol derivatives with an unusual adamantyl skeleton from Hypericum sampsonii. (Guttiferae). Org Lett 1: 879–882.

    Article  PubMed  CAS  Google Scholar 

  • Jiang J, Cane DE (2008) Geosmin biosynthesis. Mechanism of the fragmentation-rearrangement in the conversion of germacradienol to geosmin. J Am Chem Soc 130: 428–429.

    Article  PubMed  CAS  Google Scholar 

  • Juarez MP, Fernandez GC (2007) Cuticular hydrocarbons of triatomines. Comp Biochem Physiol Mol Integr Physiol 147: 711–730.

    Article  CAS  Google Scholar 

  • Kimura M, Tokai T, Takahashi-Ando N, Ohsato S, Fujimura M (2007) Molecular and genetic studies of Fusarium.Trichothecene biosynthesis: pathways, genes and evolution. Biosci Biotechnol Biochem 71: 2105–2123.

    Article  PubMed  CAS  Google Scholar 

  • King JW (2002) Supercritical fluid extraction: present status and prospects. Grasas y Aceites 53: 8–21.

    Article  CAS  Google Scholar 

  • Koga Y, Morii H (2006) Special methods for the analysis of ether lipid structure and metabolism in archaea. Anal Biochem 348: 1–14.

    Article  PubMed  CAS  Google Scholar 

  • Kuo MS, Zielinski RJ, Cialdella JI, Marschke CK, Dupuis MJ, Li GP, Kloosterman DA, Spilman CH, Marshall VP (1995) Discovery, isolation, structure elucidation, and biosynthesis of U-106305, a cholesteryl ester transfer protein inhibitor from UC 11136. J Am Chem Soc 117: 10629–10634

    Article  CAS  Google Scholar 

  • Marriot PJ, Shellie R, Cornwell C (2001) Gas chromatographic technologies for the analysis of essential oils. J Chromatogr A 936: 1–22.

    Article  PubMed  CAS  Google Scholar 

  • Mondello L, Tranchida PQ, Dugo P, Dugo G (2008) Comprehensive two-dimensional gas chromtagraphy-mass spectrometry: a review. Mass Spetrom Rev 27: 101–124.

    Article  CAS  Google Scholar 

  • Moreau RA, Whitaker BD, Hicks KB (2002) Phytosterols, phytostanols, and their conjugates in foods: structural diversity, quantitative analysis, and health-promoting uses. Prog Lipid Res 41: 457–500.

    Article  PubMed  CAS  Google Scholar 

  • Mosandl A (2004) Authenticity assessment: a permanent challenge in food flavor and essential oil analysis. J Chromatogr Sci 42: 440–449.

    PubMed  CAS  Google Scholar 

  • Panagiotopoulou PM, Tsimidou M (2002) Solid phase extraction: applications to the chromatographic analysis of vegetable oils and fats. Grasas y Aceites 53: 84–95.

    CAS  Google Scholar 

  • Pichersky E, Noel JP, Dudareva N (2006) Biosynthesis of plant volatiles: nature’s diversity and ingenuity. Science 311: 808–811.

    Article  PubMed  CAS  Google Scholar 

  • Poster DL, Schantz MM, Sander LC, Wise SA (2006) Analysis of polycyclic aromatic hydrocarbons (PAHs) in environmental samples: a critical review of gas chromatographic (GC) methods. Anal Bioanal Chem 386: 859–881.

    Article  PubMed  CAS  Google Scholar 

  • Pulfer M, Murphy RC (2003) Electrospray mass spectrometry of phospholipids. Mass Spectrom Rev 22: 332–364.

    Article  PubMed  CAS  Google Scholar 

  • Ratnayake WMN (2004) Overview of methods for the determination of trans fatty acids by gas chromatography, silver-ion thin-layer chromatography, silver-ion liquid chromatography, and gas chromatography/mass spectrometry. J AOAC Int 87: 523–539.

    PubMed  CAS  Google Scholar 

  • Rezanka T, Sigler K (2007) The use of atmospheric pressure chemical ionization mass spectrometry with high performance liquid chromatography and other separation techniques for identification of triacylglycerols. Curr Anal Chem 3: 252–271.

    Article  CAS  Google Scholar 

  • Schnee C, Köllner TG, Held M, Turlings TCJ, Gershenzon J, Degenhardt J (2006) The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc Natl Acad Sci USA 103: 1129–1134.

    Article  PubMed  CAS  Google Scholar 

  • Sherma J, Fried B (2005) Thin layer chromatographic analysis of biological samples. A review. J Liq Chromatogr Relat Technol 28: 2297–2314.

    Article  CAS  Google Scholar 

  • Su Q, Rowley KG, Balazs ND (2002) Carotenoids: separation methods applicable to biological samples. J Chromatogr B Analyt Technol Biomed Life Sci 781: 393–418.

    Article  PubMed  CAS  Google Scholar 

  • Zdero C, Bohlmann F (1990) Systematics and evolution within the Compositae, seen with the eyes of a chemist. Plant Syst Evol 171: 1–14.

    Article  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this entry

Cite this entry

Abraham, WR. (2010). Biosynthetic Oils, Fats, Terpenes, Sterols, Waxes: Analytical Methods, Diversity, Characteristics. In: Timmis, K.N. (eds) Handbook of Hydrocarbon and Lipid Microbiology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-77587-4_4

Download citation

Publish with us

Policies and ethics