Biotechnology Letters

, Volume 39, Issue 7, pp 1019–1024 | Cite as

Bioconversion of lutein by Enterobacter hormaechei to form a new compound, 8-methyl-α-ionone

Original Research Paper
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Abstract

Objectives

To investigate the final product of the bioconversion of lutein by a novel lutein-degrading bacterium, Enterobacter hormaechei A20, and the kinetics of the process.

Results

A new product, 8-methyl-α-ionone, was resolved by GC–MS. The compound was further identified by NMR. A conversion yield of 90% was achieved by E. hormaechei in 36 h with 10 g lutein l−1.

Conclusions

This is the first report of the bioconversion of lutein to form 8-methyl-α-ionone. A degradation pathway is proposed.

Keywords

Bioconversion Enterobacter hormaechei Lutein 8-Methyl-α-ionone 

Notes

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (Grant No. 21476217) and Program for Science & Technology Innovation Talents in Universities of Henan Province (16HASTIT013).

Supporting information

Supplementary Figure 1—1H NMR spectrum of 8-methyl-α-ionone.

Supplementary Figure 2—13C NMR spectrum of 8-methyl-α-ionone.

Supplementary material

10529_2017_2329_MOESM1_ESM.tif (105 kb)
Supplementary material 1 (TIFF 104 kb)
10529_2017_2329_MOESM2_ESM.tif (63 kb)
Supplementary material 2 (TIFF 62 kb)

References

  1. Abate A, Brenna E, Fuganti C, Malpezzi L, Serra S (2007) The enantiomers of Iralia: preparation and odour evaluation. Tetrahedron 18:1145–1153CrossRefGoogle Scholar
  2. Armstrong GA, Hearst JE (1996) Carotenoids 2: genetics and molecular biology of carotenoid pigment biosynthesis. FASEB J 10:228–267PubMedGoogle Scholar
  3. Baldermann S, Naim M, Fleischmann P (2005) Enzymatic carotenoid degradation and aroma formation in nectarines (Prunus persica). Food Res Int 38:833–836CrossRefGoogle Scholar
  4. Bouvier F, Suire C, Mutterer J, Camara B (2003) Oxidative remodeling of chromoplast carotenoids: identification of the carotenoid dioxygenase CsCCD and CsZCD genes involved in crocus secondary metabolite biogenesis. Plant Cell 15:47–62CrossRefPubMedPubMedCentralGoogle Scholar
  5. Britton G, Liaaen-Jensen S, Pfander H (1999) Carotenoids, vol 1A. Isolation and analysis. Birkenhauser Verlag, BaselGoogle Scholar
  6. Fleischmann P, Studer K, Winterhalter P (2002) Partial purification and kinetic characterization of a carotenoid cleavage enzyme from quince fruit (Cydonia oblonga). J Agric Food Chem 50:1677–1680CrossRefPubMedGoogle Scholar
  7. Hohler A (1986) Untersuchung der Bildung und Eigenschaften von fluchtigen Nor-Carotinoiden. PhD thesis, University of Munich, GermanyGoogle Scholar
  8. Ibdah M, Azula Y, Portnoy V, Wasserman B, Bar E, Meir A, Burger Y, Hirschberg J, Schaffer AA, Katzir N, Tadmor Y, Lewinsohn E (2006) Functional characterization of CmCCD1, a carotenoid cleavage dioxygenase from melon. Phytochemistry 67:1579–1589CrossRefPubMedGoogle Scholar
  9. Krammer GE, Werkhoff P, Sommer H, Schmidt CO, Gatfield I, Bertram H-J (2002) Carotenoid degradation products in paprika powder. In: Winterhalter P, Rouseff RL (eds) Carotenoid derived aroma compounds. ACS symposium series, vol 802. ACS, Washington DC, pp 206–219Google Scholar
  10. Kumar R, Yu WL, Jiang CL, Shi CL, Zhao YP (2009) Improvement of the isolation and purification of lutein from marigold flower and its antioxidant activity. J Food Proc Eng 33:1065–1078CrossRefGoogle Scholar
  11. Legler G, Muller-Platz CM, Mentges-Hettkamp M, Pflieger Julich E (1985) On the chemical basis of the Lowry protein determination. Anal Biochem 150:278–287CrossRefPubMedGoogle Scholar
  12. Libsu S, Singh AK (2007) Development of aqua-soluble compounds based on vitamin A series molecules: synthetic transformation of beta-ionone. Indian J Chem B 46:1297–1302Google Scholar
  13. Maldonado-Robledo G, Rodríguez-Bustamante E, Sánchez-Contreras A, Rodríguez-Sanoja R, Sanchez S (2003) Production of tobacco aroma from lutein. Specific role of the microorganisms involved in the process. Appl Microbiol Biotechnol 62:484–488CrossRefPubMedGoogle Scholar
  14. Mathieu S, Terrier N, Procureur J, Bigey F, Gunata Z (2005) A carotenoid cleavage dioxygenase from Vitis vinifera L.: functional characterization and expression during grape berry development in relation to C13-norisoprenoid accumulation. J Exp Bot 56:2721–2731CrossRefPubMedGoogle Scholar
  15. Rodriguez-Bustamante E, Sanchez S (2007) Microbial production of C-norisoprenoids and other aroma compounds via carotenoid cleavage. Crit Rev Microbiol 33:211–230CrossRefPubMedGoogle Scholar
  16. Sanchez-Contreras A, Jimenez M, Sanchez S (2000) Bioconversion of lutein to products with aroma. Appl Microbiol Biotechnol 54:528–534CrossRefPubMedGoogle Scholar
  17. Schwartz SH, Qin X, Loewen MC (2004) The biochemical characterization of two carotenoid cleavage enzymes from Arabidopsis indicates that a carotenoid-derived compound inhibits lateral branching. J Biol Chem 279:46940–46945CrossRefPubMedGoogle Scholar
  18. Scragg AH (2007) The production of flavors by plant cell cultures. In: Berger RG (ed) Flavors and fragrances. Chemistry, bioprocessing and sustain-ability. Springer, Berlin, pp 599–614Google Scholar
  19. Simkin AJ, Schwartz SH, Auldridge M, Taylor MG, Klee HJ (2004) The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles β-ionone, pseudoionone, and geranylacetone. Plant J 40:882–892CrossRefPubMedGoogle Scholar
  20. Sui X, Kiser PD, Lintig J, Palczewski K (2013) Structural basis of carotenoid cleavage: from bacteria to mammals. Arch Biochem Biophys 539:203–213CrossRefPubMedGoogle Scholar
  21. Tavakoli R, Mohadjerani M, Hosseinzadeh R, Tajbakhsh M, Naqinezhad A (2012) Essential-oil and fatty-acid composition, and antioxidant activity of extracts of Ficaria kochii. Chem Biodivers 9:2732–2741CrossRefPubMedGoogle Scholar
  22. Zhao Y, Zhong GF, Yang XP, Hu XM, Mao DB, Ma YP (2015) Bioconversion of lutein to form aroma compounds by Pantoea dispersa. Biotech Lett 37:1687–1692CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2017

Authors and Affiliations

  1. 1.School of Food and Biological EngineeringZhengzhou University of Light IndustryZhengzhouChina
  2. 2.China Tobacco, Shandong Industrial Co. Ltd.JinanChina
  3. 3.Henan Provincial Collaborative Innovation Center for Food Production and SafetyZhengzhouChina

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