DOI QR코드

DOI QR Code

Analysis and Decrease of Cyanogenic Glucosides in Flaxseed

아마인에 함유된 시안배당체의 분석과 저감화

  • Park, Eun-Ryong (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Hong, Jin-Hwan (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Lee, Dong-Ha (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Han, Sang-Bae (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Lee, Kang-Bong (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Park, Jae-Seok (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Chung, Hyung-Wook (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Hong, Kyung-Hyun (Center for Food Standard Evaluation, Korea Food & Drug Administration) ;
  • Kim, Myung-Chul (Center for Food Standard Evaluation, Korea Food & Drug Administration)
  • 박은령 (식품의약품안전청 식품규격평가부) ;
  • 홍진환 (식품의약품안전청 식품규격평가부) ;
  • 이동하 (식품의약품안전청 식품규격평가부) ;
  • 한상배 (식품의약품안전청 식품규격평가부) ;
  • 이강봉 (식품의약품안전청 식품규격평가부) ;
  • 박재석 (식품의약품안전청 식품규격평가부) ;
  • 정형욱 (식품의약품안전청 식품규격평가부) ;
  • 홍경현 (식품의약품안전청 식품규격평가부) ;
  • 김명철 (식품의약품안전청 식품규격평가부)
  • Published : 2005.07.01

Abstract

Linustatin and neolinustatin in flaxseed are called cyanogenic glucosides which produce acetone, hydrogen cyanide (HCN) and sugar when hydrolyzed. The HCN is the chemical whose toxin is being issued in food safety. Linustatin and neolinustatin were found in flaxseed by 206.5 and 174.2 mg/100 g, respectively using a RI-HPLC and LC/MSn analysis of $80\%$ methanol extraction. Also, HCN (137.38 mg/kg) was found in flaxseed distillate by autohydrolysis and IC analysis. More than 85$\%$ of linustatin, neolinustatin and HCN were removed when flaxseed was heated for more than 2 hours in $200^{\circ}C$. Especially, HCN was decreased to $98\%$ by heating only 30 min in $200^{\circ}C$.

아마인의 linustatin과 neolinustatin은 가수분해되어 acetone, hydrogen cyanide(HCN) 그리고 sugar를 생성하는 diglucoside 시안배당체로써 가수분해물인 HCN의 독성으로 인해 식품의 안전성에 문제가 되고 있다. $80\%$ methanol 추출과 LC/MSn에 의한 정성분석과 RI-LC에 의한 아마인에서 함유된 시안배당체 함량을 조사한 결과, linustatin과 neolinustatin이 각각 평균 206.5 mg/100 g과 174.2 mg/100 g 함유되어 있었다. 또한 autohydrolysis 후 증류액으로부터 IC 분석 에 의 해 HCN 137.38 mg/kg이 가수분해되어 유리됨을 알 수 있었다. 시안배당체의 저감화를 위하여 가열처리를 수행한 결과, 아마인은 $200^{\circ}C$에서 2시간 이상 가열시 $85\%$ 이상의 linustatin과 neolinustatin 그리고 HCN의 제거효과를 보였다. 특히 $200^{\circ}C$에서 30분 가열시 $98\%$의 HCN이 제거됨을 관찰할 수 있었다.

Keywords

References

  1. Spencer KC, Seiglera DS, Nahrstedtb A. 1986. Linamarin, lotaustralin, linustatin and neolinustatin from Passiflora species. Phytochem 25: 645-647 https://doi.org/10.1016/0031-9422(86)88016-5
  2. Irena NS. 1998. Cyanogenic glucosides in Linum usitatissirnum. Phytochem 49: 59-63 https://doi.org/10.1016/S0031-9422(97)00953-9
  3. Amarowicz R, Chong X, Shahidi F. 1993. Chromatographic techniques for preparation of linustatin and neolinustatin from flaxseed: Standards for glycoside analyses. Food Chem 48: 99-101 https://doi.org/10.1016/0308-8146(93)90228-8
  4. Smith CR, Weisleder D, Miller RW, Palmer IS, Olson OE. 1980. Linustatin and neolinustatin: Cyanogenic glycosides of linseed meal that protect animals against selenium toxicity. J Org Chem 45: 507-510 https://doi.org/10.1021/jo01291a027
  5. Kobaisy M, Oomah BD, Mazza G. 1996. Determination of cyanogenic glycosides in flaxseed by barbituric acid-pyridine, pyridine-pyrazolone, and high-performance liquid chromatography methods. J Agric Food Chem 44: 3178-3181 https://doi.org/10.1021/jf950838j
  6. Wanasundara PKJPD, Shahidi F, Brosnan ME. 1999. Changes in flax (Linum usitatissmum) seed nitrogenous compounds during germination. Food Chem 65: 289-295 https://doi.org/10.1016/S0308-8146(98)00176-9
  7. Selmar D, Liebereia R, Junqueirab N, Biehl B. 1991. Changes in cyanogenic glucoside content in seeds and seedlings of Hevea species. Phytochem 30: 2135-2140 https://doi.org/10.1016/0031-9422(91)83601-G
  8. Selmar D, Liebereid R, Biehld B, Nahrstedta A, Schmidtmannb V, Wrayc V. 1987. Occurrence of the cyanogen linustatin in Hevea brasiliensis. Phytochem 26: 2400-2401 https://doi.org/10.1016/S0031-9422(00)84729-9
  9. Selmar D, Lieberei R, Beehl B. 1988. Mobilization and utilization of cyanogenic glycosides. The linustatin pathway. Plant Physiol 86: 711-716 https://doi.org/10.1104/pp.86.3.711
  10. Lei V, Amoa-Awua WKA, Brimer L. 1999. Degradation of cyanogenic glycosides by Lactobacillus plantarum strains from spontaneous cassava fermentation and other microorganisms. Int J Food Microbiol 53: 169-184 https://doi.org/10.1016/S0168-1605(99)00156-7
  11. Brimer L, Brogger Christensen S, Molgaard P, Nartey F. 1983. Determination of cyanogenic compounds by thin-layer chromatography. 1. A densitometric method for quantification of cyanogenic glycosides, employing enzyme preparations ($\beta$-glucuronidase) from Helix pomatia and picrate-impregnated ion-exchange sheets. J Agric Food Chem 31: 789-793 https://doi.org/10.1021/jf00118a027
  12. Oomah BD, Mazza G, Kenaschuk EO. 1992. Cyanogenic compounds in flaxseed. J Agric Food Chem 40: 1346-1348 https://doi.org/10.1021/jf00020a010
  13. Tylleskar T, Rosling H, Banea M, Bikangi N, Cooke RD, Poulter NH. 1992. Cassava cyanogens and konzo, an upper motoneuron disease found in Africa. The Lancet 339: 208-211 https://doi.org/10.1016/0140-6736(92)90006-O
  14. Kim DH. 1995. Food chemistry. Tamgudang, Seoul. p 726-729
  15. Feng D, Shen Y, Chavez ER. 2003. Effectiveness of different processing methods in reducing hydrogen cyanide content of flaxseed. J Sci Food Agric 83: 836-841 https://doi.org/10.1002/jsfa.1412
  16. Wanasundara PKJPD, Amarowicz R, Kara MT, Shahidi F. 1993. Removal of cyanogenic glycosides of flaxseed meal. Food Chem 48: 263-266 https://doi.org/10.1016/0308-8146(93)90138-6
  17. Spencer KC, Seiglera DS, Nahrstedtb A. 1986. Linamarin, lotaustralin, linustatin and neolinustatin from Passiflora species. Phytochem 25: 645-647 https://doi.org/10.1016/0031-9422(86)88016-5
  18. Chadha RK, Lawrence JF, Ratnayake WMN. 1995. Ion chromatographic determination of cyanide released from flaxseed under autohydrolysis conditions. Food Addit Contam 12: 527-533 https://doi.org/10.1080/02652039509374341

Cited by

  1. Flax and flaxseed oil: an ancient medicine & modern functional food vol.51, pp.9, 2014, https://doi.org/10.1007/s13197-013-1247-9
  2. Impact of extrusion processing conditions on lipid peroxidation and storage stability of full-fat flaxseed meal vol.14, pp.1, 2015, https://doi.org/10.1186/s12944-015-0076-4
  3. Quality and Antioxidant Properties of Pound Cakes Supplemented with Flaxseed Powder vol.43, pp.12, 2014, https://doi.org/10.3746/jkfn.2014.43.12.1959
  4. Effect of Dose and Administration Period of Seed Cake of Genetically Modified and Non-Modified Flax on Selected Antioxidative Activities in Rats vol.16, pp.6, 2015, https://doi.org/10.3390/ijms160614259
  5. Linseed Essential Oil - Source of Lipids as Active Ingredients for Pharmaceuticals and Nutraceuticals vol.26, pp.24, 2005, https://doi.org/10.2174/0929867325666181031105603