Advertisement

European Food Research and Technology

, Volume 232, Issue 3, pp 389–395 | Cite as

Effect on garlic greening and thermal stability of 1-(2′-hydroxybenzene-1′-carboxy-ethyl) pyrrole

  • Dan Wang
  • Xihong Li
  • Xiaoyan Zhao
  • Guanghua ZhaoEmail author
Original Paper

Abstract

1-(2′-Hydroxybenzene-1′-carboxy-ethyl) pyrrole (P-Tyr) was synthesized to study its effect on garlic greening. The puree of freshly harvested garlic bulbs turned green after being soaked in solutions of P-Tyr, and with increasing concentration, the green color of the puree became deeper. The thermal stability of P-Tyr was studied by differential scanning calorimetry. Thermodynamic analysis showed that the conversion of P-Tyr followed an Arrhenius relationship, where the delta enthalpy (H) and activation energy (Ea) were 399.102 J/g and 82.137 ± 3.243 kJ/mol, respectively. Furthermore, the relationships between the degree of conversion of P-Tyr and time or temperature were reported. This study demonstrated that the evaluated P-Tyr is stable over a wide range of temperatures and time.

Keywords

1-(2′-Hydroxybenzene-1′-carboxy-ethyl) pyrrole Garlic Green pigment Thermal stability 

Notes

Acknowledgments

This work was supported by Postdoctoral Science Foundation of China (20100470789) and the National Natural Science Foundation of China (31000786).

References

  1. 1.
    Bai B, Chen F, Liao X, Zhao G, Hu X (2005) Mechanism of the greening color formation of “Laba” garlic, a homemade Chinese food product. J Agric Food Chem 53:7103–7107CrossRefGoogle Scholar
  2. 2.
    Bai B, Li L, Hu X, Wang Z, Zhao G (2006) Increase in the permeability of tonoplast of garlic (Allium sativum) by monocarboxylic acids. J Agric Food Chem 54:8103–8107CrossRefGoogle Scholar
  3. 3.
    Imai S, Akita K, Tomotake M, Swada H (2006) Identification of two novel pigment precursors and a reddish-purple pigment involved in the blue-green discoloration of onion and garlic. J Agric Food Chem 54:843–847CrossRefGoogle Scholar
  4. 4.
    Imai S, Akita K, Tomotake M, Sawada H (2006) Model studies on precursor system generating blue pigment in onion and garlic. J Agric Food Chem 54:848–852CrossRefGoogle Scholar
  5. 5.
    Kubec R, Velíšek J (2007) Allium discoloration: the color-forming potential of individual thiosulfinates and amino acids: structural requirements for the color-developing precursors. J Agric Food Chem 55:3491–3497CrossRefGoogle Scholar
  6. 6.
    Kubec R, Hrbáčová M, Musah RA, Velíšek J (2004) Allium discoloration: precursors involved in onion pinking and garlic greening. J Agric Food Chem 52:5089–5094CrossRefGoogle Scholar
  7. 7.
    Kim WJ, Cho JS, Kim KH (1999) Stabilization of ground garlic color by cysteine, ascorbic acid, trisodium phosphate and sodium metabisulfite. J Food Qual 22:681–691CrossRefGoogle Scholar
  8. 8.
    Adams JB, Brown HM (2007) Discoloration in raw and processed fruits and vegetables. Food Sci Nutr 47:319–333Google Scholar
  9. 9.
    Lukes TM (1986) Factors governing the greening of garlic Puree. J Food Sci 51(1577):1581–1582Google Scholar
  10. 10.
    Block E (1992) The organosulfur chemistry of the genus Allium—implications for the organic chemistry of sulfur. Angew Chem (International ed. in English) 31:1135–1178CrossRefGoogle Scholar
  11. 11.
    Wang D, Nanding H, Han N, Chen F, Zhao G (2008) 2-(1H-Pyrrolyl) carboxylic acids as pigment precursors in garlic greening. J Agric Food Chem 56:1495–1500CrossRefGoogle Scholar
  12. 12.
    Wang D, Yang X, Wang Z, Hu X, Zhao G (2009) Isolation and identification of one kind of yellow pigments from model reaction systems related to garlic greening. Food Chem 117:296–301CrossRefGoogle Scholar
  13. 13.
    Lee CH, Parkin KL (1998) Relationship between thiosulfinates and pink discoloration in onion extracts, as influenced by pH. Food Chem 61:345–350CrossRefGoogle Scholar
  14. 14.
    Hidalgo FJ, Zamora R (1995) Characterization of the products formed during microwave irradiation of the non enzymatic browning lysine/(E)-4,5-Epoxy-(E)-2-heptenal model system. J Agric Food Chem 43:1023–1028CrossRefGoogle Scholar
  15. 15.
    Zamora R, Hidalgo FJ (1995) Linoleic acid oxidation in the presence of amino compounds produces pyrroles by carbonyl amine reactions. Biochim Biophys Acta 1258:319–327Google Scholar
  16. 16.
    Zamora R, Alaiz M, Hidalgo FJ (1997) Feed-back inhibition of oxidative stress by oxidized lipid/amino acid reaction products. Biochemistry 36:15765–15771CrossRefGoogle Scholar
  17. 17.
    Hidalgo FJ, Alaiz M, Zamora R (1998) A spectrophotometric method for the determination of proteins damaged by oxidized lipids. Anal Biochem 262:129–136CrossRefGoogle Scholar
  18. 18.
    Wang D, Hu X, Zhao G (2008) Effect of the side chain size of 1-alkyl-pyrroles on antioxidant activity and “Laba” garlic greening. Int J Food Sci Technol 43:1880–1886CrossRefGoogle Scholar
  19. 19.
    Costa EM, Filho JM, Nascimento TG, Macêdo RO (2002) Thermal characterization of the quercetin and rutin flavonoids. Thermochim Acta 392–393:79–84CrossRefGoogle Scholar
  20. 20.
    Gloede J, Poduška K, Gross H, Rudinger J (1968) Amino acids and peptides. LXXX. α-Pyrrolo analogues of α-amino acids. Collect Czechoslov Chem Commun 33:1307–1314Google Scholar
  21. 21.
    Sircar L, Winters RT, Quin J III, Lu GH, Major TC, Panek RL (1993) Nonpeptide angiotensin II receptor antagonists. I. Synthesis and in vitro structure-activity relationships of 4-[[[(1H-pyrrol-1-ylacetyl) amino] phenyl] imidazole derivatives as angiotensin II receptor antagonists. J Med Chem 36:1735–1745CrossRefGoogle Scholar
  22. 22.
    Li L, Hu D, Jiang Y, Chen F, Hu X, Zhao G (2008) Relationship between γ-Glutamyl transpeptidase activity and garlic greening, as controlled by temperature. J Agric Food Chem 56(3):941–945CrossRefGoogle Scholar
  23. 23.
    Perrenot B, Widmann G (1991) TG and DSC kinetics of thermal decomposition and crystallization processes. J Therm Anal 37:1785–1792CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Dan Wang
    • 1
    • 2
    • 3
  • Xihong Li
    • 1
  • Xiaoyan Zhao
    • 2
  • Guanghua Zhao
    • 3
    • 4
    • 5
    Email author
  1. 1.Key Laboratory of Food Nutrition and SafetyTianjin University of Science & Technology, Ministry of EducationTianjinChina
  2. 2.Vegetable Research CenterBeijing Academy of Agriculture and Forestry SciencesBeijingChina
  3. 3.College of Food Science and Nutritional EngineeringChina Agricultural UniversityBeijingChina
  4. 4.Engineering Research Centre for Fruits and Vegetables Processing, Ministry of EducationBeijingChina
  5. 5.Key Laboratory of Fruits and Vegetables Processing, Ministry of AgricultureBeijingChina

Personalised recommendations