Journal of the Korean Society of Food Science and Nutrition (한국식품영양과학회지)

The Korean Society of Food Science and Nutrition (한국식품영양과학회)
권호 표지
DOI QR코드

DOI QR Code

Identification of Shikonin and Its Derivatives from Lithospermum erythrorhizon

야생 및 재배 지치뿌리의 Shikonin 화합물 확인

  • Kim, Jin-Sook (National Rural Resources Development Institute, RDA) ;
  • Han, Young-Sil (Dept. of Food and Nutrition, Sookmyung Women's University) ;
  • Kang, Myung-Hwa (Dept. of Food Science and Nutrition, Hoseo University)
  • 김진숙 (농업과학기술원 농촌자원개발연구소) ;
  • 한영실 (숙명여자대학교 식품영양학과) ;
  • 강명화 (호서대학교 식품영양학과)
  • Published : 2006.02.01
Download PDF
⟨ Previous Next ⟩

Abstract

In this study, phytochemicals from the wold and cultivated Lithospermum erythrorhizon (gromwell), which has been used for medicinal purpose or natural coloring material from the old days, were extracted by methanol and fractionated with hexane. The shikonin compounds in the fraction was isolated and their chemical structures were identified by $^1H$ and $^{13}C-NMR$. It was found that compound I was the shikonin substance with molecular weight of 288.3 and chemical formula of $C_{16}H_{16}O_5$, and compound II being deoxyshikonin substance with molecular weight of 272.3 and chemical formula of $C_{16}H_{16}O_4$. The Quantities of these compounds in the wild and cultivated gromwells was determined.

야생 및 재배지치의 methanol 추출물로 조제한 n-herane 용매 분획물에 대하여 shikonin 및 그 유도체 화합물을 표품으로 해서 HPLC/MS로 물질을 분리하였다. 분리된 물질의 구조 확인을 위해 $^1H-NMR$, $^{13}C-NMR$을 통해 분석한 결과, compound I은 화학식이 $C_{16}H_{16}O_5$이며 분자량이 288.3인 shikonin이었고, compound II는 화학식이 $C_{16}H_{16}O_4$이며 분자량이 272.3인 deoxyshikonin것으로 밝혀내었다. 야생지치에 함유된 shikonin과 deoxyshikonin은 $2.23\%,\;0.87\%$이었고, 재배지치에는 각각 $2.24\%,\;0.41\%$이었다. 지치의 동정된 색소물질 총량은 야생지치 $3.12\%$, 재배지치 $2.64\%$로 야생지치가 재배지치보다 유의적으로 많았다(p<0.05).

Keywords

References

  1. 이창복. 2003. 대한식물도감(하). 향문사, 서울. p 97-107
  2. 이춘녕, 김우정. 1985. 천연향신료와 식용색소. 향문사, 서울
  3. Kyogoku K, Terayama H, Tachi Y, Suzuki T, Komatsu M. 1973. Studies on the constituents of 'Shikonin'I. Structure of three new shikonin derivatives and isolation of anhydro alkannin. Shoyakugaku Zassi 27: 24-30
  4. Hsu HY, Chen YP, Hong M. 1982. The chemical constitutes of oriental herbs. Oriental Healing Arts Institute. p 170
  5. Hisamichi S, Yoshizaki F. 1982. Studies on the shikonin I. Structures of new minor pigments and isolation of two isomers of shikonin derivatives from Lithospermum erythrorhizon Sieb. et Zucc. Shoyakugaku Zasshi 36: 154-159
  6. Morito L, Kishi T, Ikegami S. 1985. Naphthoquinone der-ivates from Lithospermum erythrorhizon Siebold et Zuccarint. Tetrahedron Letters 52: 4739-4745
  7. Morito I, Hirata Y. 1966. New naphthoquinone derivates from Lithospermum erythrorhizon. Tetrahedron Letters 31: 3677-3680
  8. Tang W, Eisenbrand G. 1992. Chinese drugs of plant origin. Springer Verlag, Berlin, Heidelberg, Germany. p 613-619
  9. Schmid HV, Zenk MH. 1971. $\rho$-Hydroxybenzoic acid and mevalonic acid as precursors of the plant naphthoquinone alkanin. Tetrahedron Letters 44: 4151-4158
  10. Tusukada M, Fukui H, Hhabara C, Tabata M. 1983. Com-parative studies on naphthoquinone derivatives in various crude drugs 'Zicao (shikonin)'. Shoyakugaku Zasshi 37: 299- 303
  11. 谷村顯雄, 片山條, 遠縢英美, 黑川和男, 吉積智司. 1979. 天然着色料. 光琳, 東京. p 373-403
  12. Han TY, Back YS, Kim SY, Jung YS, Yoon HY. 1998. Development and utilization of natural food colorants. Korea Food Institute, Sungnam, Korea
  13. Hwang SY, Hwang BY, Kang SS, Kim CM, Park JH, Bae KH, Son KH, Lee SH, Chang SY, Kamg SJ, Lee KS. 2000. Isolation and quantative analysis of acetylshikonin from Lithospermi radix. Kor J Pharmacogn 31: 295-299
  14. Konnol C, Mizuno T, Hikino H. 1985. Isolation and hy-poglycemic activity of Lithospermum erythrorhizon roots. Planta Medica 51: 157-158 https://doi.org/10.1055/s-2007-969434
  15. Kang MY, Shin SY, Nam SH. 2003. Correlation of anti-oxidant and antimutagenic activity with content of pigments and phenolic compounds of colored rice seeds. Korean J Food Sci Technol 35: 968-974
  16. Kim JS. 2005. Identification of coloring substance from Lithospermum erythrorhizon and the quality of Kangjung with its extract. PhD Dissertation. Sookmyung Women's Univ., Seoul, Korea
  17. Kim BH, Park KW, Kim JY, Jeoung IY, Yang GH, Cho YS, Yee ST, Seo KI. 2004. Purification and characterization of anticarcinogenic compound from Corni fructus. Korean J Food Sci Tech 36: 1001-1007
  18. Lee JH. 1996. The antioxidizing, nitrate-scavenging and antimutagenic activities of Ecklonia stolonifea. MS Thesis. Bukyoung National Univ., Busan, Korea
  19. Nishida K, Kobayash K. 1992. Dyeing properties of natural dyes under aftertreatment using metallic mordants. American Dyestuff Reporter 81(5): 61-63
  20. Yoo KS. 1980. Studies on an analytical method and indica-tive characters on shikonin. PhD Dissertation. Seoul Univ., Seoul, Korea
  21. Hiroshi F, FerojHasan AFM, Tomohiro U, Masaharu K. 1998. Formation and secretion of new brown benzoquinone by hairy root cultures of Lithospermum erythrorhizon. Phytochemistry 47: 1037-1039 https://doi.org/10.1016/S0031-9422(97)00694-8
  22. Tetsuya A, Changqi Z, Hajime M, Keisuke K, Toshihiro Y, Shirou F, Setsuko S, Motoyoshi S, Yukio O. 2000. Quantitative determination of shikonin on Shiunko. Natural Medicine 54: 81-85

Cited by

  1. Enhancement of Whitening Effects of Lithospermum erythrorhizon Extracts by Ultra High Pressure vol.19, pp.2, 2011, https://doi.org/10.7783/KJMCS.2011.19.2.097
  2. Antioxidant Activity of Solvent Fractions from Cultivated and Wild Gromwell vol.39, pp.6, 2010, https://doi.org/10.3746/jkfn.2010.39.6.789
  3. Improved cosmetic activity by optimizing the Lithospermum erythrorhizon extraction process vol.67, pp.1, 2015, https://doi.org/10.1007/s10616-013-9657-0
  4. Studies on Seed Germination Characteristics and Patterns of Protein Expression of Lithospermum erythrorhizon by Plant Growth Regulators and Seed Primings vol.22, pp.6, 2014, https://doi.org/10.7783/KJMCS.2014.22.6.435
  5. 페놀 화합물로부터 HMG-CoA reductase 저해 활성 물질 탐색 vol.27, pp.3, 2006, https://doi.org/10.5352/jls.2017.27.3.325
  6. 황기, 지치 복합물의 연골세포에서의 Matrix Metalloproteinases 저해 효과 및 유효성분의 분석 vol.27, pp.4, 2006, https://doi.org/10.7783/kjmcs.2019.27.4.247