DOI QR코드

DOI QR Code

Chemical change of urushiol during heating process of Toxicodendron vernicifluum resin

Urushiol의 화학적 변화를 통한 건칠(乾漆)의 포제법(炮製法) 고찰

  • Kim, Jung-Hoon (Division of Pharmacology, School of Korean Medicine, Pusan National Univ.) ;
  • Doh, Eui jeong (Research Center of Traditional Korean Medicine, Wonkwang Univ.) ;
  • Lee, Guemsan (Research Center of Traditional Korean Medicine, Wonkwang Univ.)
  • 김정훈 (부산대학교 한의학전문대학원 약물의학부) ;
  • 도의정 (원광대학교 한국전통의학연구소) ;
  • 이금산 (원광대학교 한국전통의학연구소)
  • Received : 2020.01.10
  • Accepted : 2020.03.25
  • Published : 2020.03.30

Abstract

Objectives : Heating process is the traditional processing method that has been applied to reduce the toxicity of dried resin of Toxicodendron vernicifluum (Anacardiacea) used as Geon-chil (乾漆, Lacca Rhois Exsiccata or Toxicodendri Resina). Urushiol, which is found in the plants of Toxicodendron genus, is a toxic compound that is absorbed into the skin and induces allergic dermatitis by being contacted. Hence, the reduction of urushiol level by heating processing of Geon-chil is crucial method for its medicinal application. Methods : Due to lack of Geon-chil processing-related articles, the articles researching the processing of lacquer (漆), as a coating material, were collected and analyzed to investigate the chemical change of urushiol during heating process. Results : The results demonstrate that the resin which was collected from the sap of T. vernicifluum tree was dried under warm and humid conditions repeatedly. During primary drying process, the laccase, a copper-containing enzyme in the resin, participated in the formation of urushiol polymers and thereafter urushiol-related toxicity could be reduced by making a lacquer harder and more stable. Moreover, heating a lacquer over 200℃ could cause thermo-degradation of urushiol polymers, and vaporized thermally degraded urushiol monomers and their by-products, which were determined using pyrolysis/GC-MS. Conclusions : These results support that heating process being performed over 200 ℃, such as stir-frying (炒) or calcination (煅), reduces the urushiol content in Geon-chil and hence, its medicinal use can be more stable without urushiol-related allergic reactions.

Keywords

References

  1. Ministry of Korean Food and Drug Safety. The Korean Herbal Pharmacopoeia. The Part 1. KFDA Notification No. 2019-72.
  2. Herbology editorial committee of Korean medicine schools. Herbology. Seoul : Yeonglimsa. 2016 : 477-8.
  3. Jeong SH, Cho SH, Lee SC, Kim SY. Immunohistochemical study on allergic contact dermatitis and systemic contact dermatitis to urushiol (Rhus verniciflua). Korean J. Dermatol. 1997 ; 35(6) : 1052-8.
  4. Johnson RA, Haer H, Kirkpatrick CH, Dawson CR, Khurana RG. Comparison of the contact allergenicity of the four pentadecylcatechols derived from poison ivy urushiol in human subjects. J. Allergy Clin. Immunol. 1972 ; 49(1) : 27-35. https://doi.org/10.1016/0091-6749(72)90120-0
  5. Ma XM, Lu R, Miyakoshi T. Recent advances in research on lacquer allergy. Allergol. Int. 2012 ; 61 : 45-50. https://doi.org/10.2332/allergolint.11-RA-0324
  6. Lee WJ, Kang JE, Choi JH, Jeong ST, Kim MK, Choi HS. Comparison of the flavonoid and urushiol content in different parts of Rhus verniciflua Stokes grown in Wonju and Okcheon. Korean J. Food Sci. Technol. 2015 ; 47(2) : 158-63. https://doi.org/10.9721/KJFST.2015.47.2.158
  7. Kumanotani J. Enzyme catalyzed durable and authentic oriental lacquer: a natural microgel-printable coating by polysaccharide-glycoprotein-phenolic lipid complexes. Prog. Org. Coat. 1998 ; 34 : 135-46. https://doi.org/10.1016/S0300-9440(97)00115-X
  8. Yang J, Deng J, Zhu J, Liu W, Zhou M, Li D. Thermal polymerization of lacquer sap and its effects on the properties of lacquer film. Prog. Org. Coat. 2016 ; 94 : 41-8. https://doi.org/10.1016/j.porgcoat.2016.01.021
  9. McGovern TW, Barkley TM. Botanical dermatology. Int. J. Dermatol. 1998 ; 37(5) : 321-34. https://doi.org/10.1046/j.1365-4362.1998.00385.x
  10. Koo JS, Lee SN, Seo BI. A philological study on poisoning of herbal medicines used to activate blood flow and remove blood stasis(活血祛瘀藥). Kor. J. Herbol. 2010 ; 25(2) : 21-39. https://doi.org/10.6116/KJH.2010.25.2.021
  11. Ha H, Kim Y, Kweon K, Kim J. Review of the domestic research trends in the study of Korean herbal medicine with anti-inflammation effects. Kor. J. Herbol. 2011 ; 26(4) : 15-22. https://doi.org/10.6116/KJH.2011.26.4.015
  12. Choi HS. MicroRNA expression in leukemia cell line(K562 cell) using Rhus verniciflua Stokes. Kor. J. Herbol. 2019 ; 34(6) : 71-8.
  13. unknown. Shennongbencaojing[神農本草經]. Han period, 25-220. In: Ma GH, ed. Shennongbencaojing Jijiao[神農本草經輯注]. Beijing, China: People's Medical Publishing House. 2013 : 204-5.
  14. Tao HJ. Mingyibielu[名醫別錄]. Han period, 456-536. In : Shang ZJ, ed. Mingyibielu(Jijiaoben) [名醫別錄(輯校本)]. Beijing, China: People's Medical Publishing House. 1986 : 37-8.
  15. Tao HJ. Bencaojingjizhu[本草經集注]. Liang period, 456-536. In : Shang ZJ, Shang YS, ed. Bencaojing jizhu(Jijiaoben)[本草經集注(輯校本)]. Beijing, China: People's Medical Publishing House. 1994 : 219-20.
  16. Su J, et al. Xinxiubencao[新修本草]. Tang period, 659. In : He QH, ed. Xinxiubencao. Beijing, China:Shanxi Science & Technology Publishing House. 2012 : 271.
  17. unknown. Rihuazibencao[日華子本草]. Five Dynasties and Ten Kingdoms period, 908-923. In: Shang ZJ, ed. Rihuazibencao(Jishiben).Shubencao(Jifuben) [日華子本草(輯釋本).蜀本草(輯复本)]. Hefei, China: Anhui Science & Technology Press. 2005 : 116-7.
  18. Zhang YX, et al. Jiayoubencao[嘉祐本草]. Song period, 1060. In : Shang ZJ, ed. Jiayoubencaojijiaoben[嘉祐本草輯复本]. Beijing, China: Traditional Chinese Medicine Classics Press. 2009 : 282-3.
  19. Tang SW, et al. Jingshizhenghezhengleibeiyongbencao [經史政和證 類備用本草]. Song period, 1116. In : Guo JS, Jin XM, Zhao YM, ed. Zhengleibencao[證類本草]. Beijing, China: China Medical Science Press. 2011 : 390-1.
  20. Kou ZS. Bencaoyanyi[本草衍義]. Song preiod, 1116. In : Zhang LJ, ed. Bencaoyanyi[本草衍義]. Beijing, China: China Medical Science & Technology Press. 2012 : 52.
  21. Liu WQ, et al. Bencaopinhuijingyao[本草品彙精要]. Ming period, 1505. In : Lu Z, Li ZY, ed. Bencaopinhuijingyao[本草品彙精要]. Beijing, China: China Press of Traditional Chinese Medicine. 2013 : 393-4.
  22. Chen JM. Bencaomengquan[本草蒙筌]. Ming period, 1565. In : Zhang RX, Han XJ, Zhao HL, ed. Bencaomengquan[本草蒙筌]. Beijing, China: China Press of Traditional Chinese Medicine. 2008 : 236.
  23. Li ZZ. Leigongpaozhiyaoxingjie[雷公炮製藥性解]. Ming period, 1622. In : Bao LF, ed. Lizhongzi Yixuequanshu[李中梓醫學全書]. Beijing, China: China Press of Traditional Chinese Medicine. 1999 : 622.
  24. Ni ZM. Bencaohuiyan[本草彙言]. Ming period, 1624. In : Zheng JS, Zhen XY, Yang MX, ed. Bencaohuiyan[本草彙言]. Beijing, China: China Press of Traditional Chinese Medicine. 2005 : 358-9.
  25. Lu ZY. Bencaochengyabanji[本草乘雅半偈]. Ching period, 1647. In : Zhang YP, ed. Bencaochengyabanjii[本草乘雅半偈]. Beijing, China: China Medical Science and Technology Press. 2014 : 63.
  26. Wang A. Bencaobeiyao[本草備要]. Ching period, 1683. Beijing, China: People's Medical Publishing House. 2005 : 155-6.
  27. Liu RJ. Bencaoshu[本草述]. Ching period, 1691. Beijing, China: China Press of Traditional Chinese Medicine. 2005 : 551.
  28. Zhang L. Benjingfengyuan[本經逢原]. Ching period, 1695. In : Gu M, Yang YZ, ed. Benjingfengyuan[本經逢原]. China: China Medical Science & Technology Press. 2011 : 176-7.
  29. Wang RA. Bencaoyidu[本草易讀]. Ching period. Beijing, China: People's Medical Publishing House. 1987 : 296.
  30. Wu YL. Bencaocongxin[本草從新]. Ching period, 1757. In : Qu JF, Dou QH, ed. Bencaocongxin[本草從新]. China:Tianjin Science & Technology Press. 2004 : 100.
  31. Yan J, Shi W, Hong W. Depeibencao[得配本草]. Ching period, 1761. In : Zheng JS, ed. Depeibencao[得配 本草]. China:People's Medical Publishing House. 2007 : 216.
  32. Yang ST. Bencaoshugouyuan[本草述鉤元]. Ching period, 1833. In : Huang X, Cui XY ed. Bencaoshugouyuan Shiyi[本草述鉤元釋義]. China: Shanxi Science & Technology Press. 2009 : 678-80.
  33. Zhao QG. Bencaoqiuyuan[本草求原]. Ching period, 1848. Beijing, China: China Press of Traditional Chinese Medicine. 2016 : 229.
  34. Lee SK, George SD, Antholine WE, Hedman B, Hodgson KO, Solomon EI. Nature of the intermediate formed in the reduction of $O_2\;to\;H_2O$ at the trinuclear copper cluster active site in native laccase. J. Am. Chem. Soc. 2002 ; 124(21) : 6180-93. https://doi.org/10.1021/ja0114052
  35. Watanabe H, Fujimoto A, Takahara A. Characterization of catechol-containing natural thermosetting polymer "Urushiol" thin film. J. Polym. Sci. 2013 ; 51 : 3688-92. https://doi.org/10.1002/pola.26770
  36. Oshima R, Yamauchi Y, Watanabe C, Kumanotani J. Enzymic oxidative coupling of urushiol in sap of the lac tree, Rhus vernicifera . J. Org. Chem. 1985 ; 50 : 2613-21. https://doi.org/10.1021/jo00215a002
  37. Nagase K, Kamiya Y, Kimura T, Hozumi K, Miyakoshi T. The relationship between the change of progress time in the urushi liquid by the enzymic polymerization and the natural dryring property occurring under a low humidity environment. Bull. Chem. Soc. Jpn. 2001 ; 10 : 587-93.
  38. Niimura N, Miyakoshi T. Structural study of oriental lacquer film during the hardening process. Talanta. 2006 ; 70(1) : 146-52. https://doi.org/10.1016/j.talanta.2005.12.039
  39. Ma XM, Lu R, Miyakoshi T. Application of pyrolysis gas chromatography/mass spectrometry in lacquer research: A review. Polymers. 2014 ; 6 :132-44. https://doi.org/10.3390/polym6010132
  40. Park J, Ahn SA. Analysis of dried Asian lacquer by pyrolysis/GC/MS. Anal. Sci. Technol. 2018 ; 31(2) : 78-87. https://doi.org/10.5806/AST.2018.31.2.78
  41. Cheong SH, Choi YW, Min BS, Choi HY. Polymerized urushiol of the commercially available Rhus product in Korea. Ann. Dermatol. 2010 ; 22(1) : 16-20. https://doi.org/10.5021/ad.2010.22.1.16
  42. Kawai K, Nakagawa M, Kawai K, Miyakoshi T, Miyashita K, Asami T. Heat treatment of Japanese lacquerware renders in hypoallergenic. Contact Dermatitis. 1992 ; 27(4) : 244-9. https://doi.org/10.1111/j.1600-0536.1992.tb03254.x