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Metabolite analysis of long chain branched fatty acids and capsaicin biosynthesis in Capsicum annuum placenta

  • Young Soo Keum
  • Hee Won Park
  • Hyuk-Hwan Song
  • Byung-Dong Kim
  • Byoung-Cheorl Kang
  • Jeong-Han KimEmail author
Original Article

Abstract

Capsaicins, hot principles in Capsicum spp., are produced from vanillylamine and short-chain fatty acids (FAs), originated from branched amino acids. Recently a minor but clear incorporation of longer chain FAs with 14–18 carbons to novel long-chain vanillylamides was reported, which prompted further investigation on possible correlation between metabolism of capsaicins and FA precursors with metabolite profiling. Placenta of Capsicum annuum with different concentrations of capsaicins were extracted and analyzed with gas chromatography-mass spectrometry. Structures of FAs were determined after derivatization to methyl- and picolinyl esters. The results indicate cultivars with more capsaicins contain higher amount of long-chain branched FAs with 14–17 carbons. Some branched FAs showed strong correlation with the level of capsaicins. Most branched FAs are of iso-acids, where the methyl groups are attached at (ω-1) carbon, whereas only one anteiso-FA was observed in a single cultivar. In addition to saturated analogues, several mono-unsaturated branched FAs have also been detected. Location of double bond in these metabolites suggested that short-chain branched FAs may be incorporated in the middle of biosynthesis or at initial steps of long-chain FAs. Accordingly, branched medium- to long-chain FA may be derived mainly from leucine or valine, rather than isoleucine. Results indicate that the short-chain FAs are possible precursors both of capsaicins and methyl-branched longer chain FAs.

Keywords

capsaicin long chain branched fatty acid metabolite profiling 

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References

  1. Aluru MR, Mazourek M, Landry LG, Curry J, Jahn M, and O’Connell MA (2003) Differential expression of fatty acid synthase genes, Acl, Fat and Kas, in Capsicum fruit. J Exp Bot 54, 1655–1664.CrossRefGoogle Scholar
  2. Beck HC (2005) Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus. FEMS Microbiol Lett 243, 37–44.CrossRefGoogle Scholar
  3. Buckner JS, Kolattukudy PE, and Rogers L (1978) Synthesis of multimethylbranched fatty acids by avian and mammalian fatty acid synthetase and its regulation by malonyl-CoA decarboxylase in the uropygial gland. Arch Biochem Biophys 186, 152–163.CrossRefGoogle Scholar
  4. Destaillats F and Angers P (2002) One-step methodology for the synthesis of FA picolinyl esters from intact lipids. J Am Oil Chem Soc 79, 253–256.CrossRefGoogle Scholar
  5. Diaz J, Pomar F, Bernal A, and Merino F (2003) Peroxidases and the metabolism of capsaicin in Capsicum annuum L. Phytochem Rev 4, 141–157.Google Scholar
  6. Graham IA and Eastmond PJ (2002) Pathways of straight and branched chain fatty acid catabolism in higher plants. Prog Lipid Res 41, 156–181.CrossRefGoogle Scholar
  7. Hierro MTG, Robertson G, Christie WW, and Joh Y-G (1996) The fatty acid composition of the seeds of Ginkgo biloba. J Am Oil Chem Soc 73, 575–579.CrossRefGoogle Scholar
  8. Kaneda T (1991) Iso- and anteiso-fatty acids in bacteria: biosynthesis, function, and taxonomic significance. Microbiol Mol Biol Rev 55, 288–302.Google Scholar
  9. Kobata K, Saito K, Tate H, Nashimoto A, Okuda H, Takemura I, Miyakawa K, Takahashi T, Iwai K, and Watanabe T (2010) Long-chain N-vanillylacylamides from Capsicum oleoresin. J Agric Food Chem 58, 3627–3631.CrossRefGoogle Scholar
  10. Kozukue N, Han J-S, Kozukue E, Lee S-J, Kim J-A, Lee G-R, Levin CE, and Friedman M (2005) Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry. J Agric Food Chem 53, 9172–9181.CrossRefGoogle Scholar
  11. Lederer E (1964) The origin and function of some methyl groups in branchedchain fatty acids, plant sterols and quinines. Biochem J 93, 449–468.Google Scholar
  12. Millar AA and Kunst L (1997) Very-long-chain fatty acid biosynthesis is controlled through the expression and specificity of the condensing enzyme. Plant J 12, 121–131.CrossRefGoogle Scholar
  13. Ohlrogge JB (1997) Regulation of fatty acid synthesis. Ann Rev Plant Physiol Plant Mol Biol 48, 109–136.CrossRefGoogle Scholar
  14. Prasad BCN, Gururaj HB, Kumar V, Giridhar P, and Ravishankar GA (2006) Valine pathway is more crucial than phenyl propanoid pathway in regulating capsaicin biosynthesis in Capsicum frutescens Mill. J Agric Food Chem 54, 6660–6666.CrossRefGoogle Scholar
  15. Reilly CA, Ehlhardt WJ, Jackson DA, Kulanthaivel P, Mutlib AE, Espina RJ, Moody DE, Crouch DJ, and Yost GS (2003) Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells. Chem Res Toxicol 16, 336–349.CrossRefGoogle Scholar
  16. Slocombe SP, Schauvinhold I, McQuinn RP, Besser K, Welsby NA, Harper A et al. (2008) Transcriptomic and reverse genetic analyses of branchedchain fatty acid and acyl sugar production in Solanum pennellii and Nicotiana benthamiana. Plant Physiol 148, 1830–1846.CrossRefGoogle Scholar
  17. Thiele R, Mueller-Seitz E, and Petz M (2008) Chili pepper fruits: presumed precursors of fatty acids characteristic for capsaicinoids. J Agric Food Chem 56, 4219–4224.CrossRefGoogle Scholar
  18. Trenkamp S, Martin W, and Tietjen K (2004) Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides. Proc Natl Acad Sci USA 101, 11903–11908.CrossRefGoogle Scholar
  19. van der Hoeven RS and Steffens JC (2000) Biosynthesis and elongation of short- and medium-chain-length fatty acids. Plant Physiol 122, 275–282.CrossRefGoogle Scholar
  20. Yano I, Nichols BW, Morris LJ, and James AT (1971) The distribution of cyclopropane and cyclopropene fatty acids in higher plants (Malvaceae). Lipids 7, 30–34.CrossRefGoogle Scholar

Copyright information

© The Korean Society for Applied Biological Chemistry 2012

Authors and Affiliations

  • Young Soo Keum
    • 2
  • Hee Won Park
    • 1
  • Hyuk-Hwan Song
    • 1
  • Byung-Dong Kim
    • 3
  • Byoung-Cheorl Kang
    • 3
  • Jeong-Han Kim
    • 1
    Email author
  1. 1.Department of Agricultural BiotechnologySeoul National UniversityGwanakgu, SeoulRepublic of Korea
  2. 2.Department of Molecular BiotechnologyKonkuk UniversitySeoulRepublic of Korea
  3. 3.Department of Horticultural ScienceSeoul National UniversitySeoulRepublic of Korea

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