Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Biotransformation Process for the Production of Sotolon as a Natural Flavour Enhancer

천연 향미소재 소톨론 생산을 위한 생물전환공정

  • Jang, In-Hwan (Dept. of Food and Biotechnology and Dept. of Innovative Industrial Technology, Hoseo University) ;
  • Kang, Min-Sook (Dept. of Food and Nutrition, Hoseo University) ;
  • Chae, Hee-Jeong (Dept. of Food and Biotechnology and Dept. of Innovative Industrial Technology, Hoseo University)
  • 장인환 (호서대학교 식품생물공학 및 벤처전문대학원 첨단산업기술) ;
  • 강민숙 (호서대학교 식품영양학) ;
  • 채희정 (호서대학교 식품생물공학 및 벤처전문대학원 첨단산업기술)
  • Published : 2004.03.31
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Abstract

Biotransformation process using microorganisms was examined to improve the bioconversion rate for the production of sotolon from the raw material. First, the extraction condition was optimized with regard to solvent type and pretreatment conditions. Dichloromethane was selected as a suitable solvent for the extraction of sotolon and sotolon-related compounds. Second, various microorganisms such as lactic acid-producing bacteria, yeast and fungi were tested for the biotransformation. Among the tested microbes, Agaricus blazei showed the highest conversion rate. Additives including amino acids, salts, and organic acids were investigated to test their effects on bioconversion. When the solution was added by isoleucine, ${\alpha}-ketoglutaric\;acid$, ascorbate, and $FeSO_4$ and later incubated by culture broth containing the mycelium of Agaricus blazei, the sotolon content increased up to about 77 times as compared to that of the raw material.

소톨론은 호로파(fenugreek)라는 콩과식물을 원료 물질로 하여 여러 가지 전환반응에 의해 생산될 수 있는 천연향미소재로서 본 연구에서는 생물 전환율을 높이기 위한 미생물이나 효소원을 탐색하였다. 원료로부터 소톨론을 추출하기 위한 유기용매로서 dichloromethane이 선별되었다. 효소원으로 사용될 수 있는 유산균, 효모, 사상균 등의 여러가지 미생물에 대한 스크리닝 결과 신령버섯(Agaricus blazei)이 높은 전환율을 보였다. 다양한 첨가물 및 전처리 조건에 따른 전환율을 조사한 결과 호로파 현탁액에 isoleucine, ${\alpha}-ketoglutaric$ acid, ascorbate, $FeSO_4$ 등의 첨가물을 첨가한 후 신령버섯의 균사체 배양액을 혼합하여 반응시키는 공정을 통하여 원료의 초기 소톨론 함량을 대략 77배 수준으로 높일 수 있었다.

Keywords

References

  1. Kim, W. J. (1986) manufacture and possibilities of nature taste enhancer. Korean J. Food Sci. Technol. 19, 46-51
  2. Dubois, R, Rigaud, J. and Dekimpe, J. (1976) IdentiScation of 4,5-dimethy1tetrahydro-furanedione-2,3 in vin jaune. Lebensm. Wiss. Technol. 9, 366-368
  3. Munch, R, Hofmann, T. and Schieberle, P. (1997) Comparison of key odorants generated by thermal treatment of commercial and self-prepared yeast extract: Influence of the amino acid composition on odorant formation. J. Agric. Food. Chem. 45, 1338-1344 https://doi.org/10.1021/jf960658p
  4. Haefele, C., Bonfils C. and Sauvaire, Y. (1997) Characterization of a dioxygenase from Trigonella foenumgraecum involved in 4-hydroxyiso1eucine biosynthesis. Phytochemistry 44, 563-566 https://doi.org/10.1016/S0031-9422(96)00620-6
  5. Girardon, R, Sauvaire, Y, Baccou, J. C. and Bessiere, J. M. (1986) Identitication of 3-hydroxy-4,5-dimethy1-2(5H)-furanone in the aroma of fenugreek seeds. Lebensm. Wiss. Technol. 19, 44-46
  6. Kobayashi, A. (1989) In Flavor Chemistry: Sotolon: identification, formation and effect on flavor. Teranishi. R., (ed.), ACS, Washington D. C., pp. 49-59
  7. Fowden, L., Pratt, H. M. and Smith, A. (1973) 4-Hydroxyisoleusine from seed of Trieonella foenumgraecum. Phytochemistry 12, 1701-1707 https://doi.org/10.1016/0031-9422(73)80390-5
  8. Pham, T. T, Guichard, E., Schlich, P. and Charpentier, C. (1995) Optimal conditions for the formation of sotolon from $\alpha$ -ketobutyric acid in the French 'vin jaune'. J. Agric. Food. Chem. 43, 2616-2619 https://doi.org/10.1021/jf00058a012
  9. Masuda, M., Okawa, E. and Nishimura, K. (1984) Identification of 4,5-dimethy1-3-hydroxy-2 (5H) furanone (sotolon) and 9 hydroxynonanone in botrytised wine and evaluation of the roles of compounds characteristic of it. Agric. Biol. Chem. 48, 2707-2710
  10. Sauvaire, Y, Girardon, J., Baccou, C. and Risterucci, A. M. (1984) Changes in growth, Proteins and free amino acids of developing seed and pod of fenugreek. Phytochemistry 23, 479-486 https://doi.org/10.1016/S0031-9422(00)80363-5
  11. Molham, A. H. and Amalam, R. (1998) Antidiabetic and hypocholesterolaemic effects of fenugreek. Phytother. Res. 12, 233-242 https://doi.org/10.1002/(SICI)1099-1573(199806)12:4<233::AID-PTR294>3.0.CO;2-V
  12. Broca, C., Manteghetti, M., Gross, R., Baissac, Y, Jacob, M. Petit, R, Sauvaire, Y. and Ribes, G. (2000) 4-hydroxyiso1eucine: effects of synthetic and natural analogues on insulin secretion. Eur. J. Pharmacol. 390, 339-345 https://doi.org/10.1016/S0014-2999(00)00030-3
  13. Chatterjee, B. R, Saker, N. and Rao, A. S. (1982) Serological and chemical investigations of the anomenc configuration of sugar units in the D-galactomannan of fenugreek (Trigonella foenumgraecum) seeds. Carbohyd. Res. 104, 348-353 https://doi.org/10.1016/S0008-6215(00)82598-7
  14. Lerch, K. (1994) Compounds and process for making a Havorant, U.S. Patent 5,449,823
  15. Batenburg, A. M., WesdorP, J. J. (1999) Process for the preparation of sotolon, U.S. Patent 6,087,138
  16. Blank, I., Jaeger, D. and Zurbriggen, B. D. (1998) Flavorant prepared from trigoneta foenum-graecum seed, U.S. Patent 6,013,289