Korean Journal of Food Science and Technology (한국식품과학회지)

Korean Society of Food Science and Technology (한국식품과학회)
권호 표지

Nitrite Scavenging Ability and SOD-like Activity of a Sterol Glucoside form Chrysanthemum coronarium L. var. spatiosum

쑥갓 스테롤배당체의 아질산염소거작용 및 SOD 유사활성

  • Cho, Min-Jung (Department of Food Science of Technology, Seoul National University of Technology) ;
  • Park, Mi-Jung (Department of Visual Optics, Seoul National University of Technology) ;
  • Lee, Heum-Sook (Department of Food Science of Technology, Seoul National University of Technology)
  • 조민정 (서울산업대학교 식품공학과) ;
  • 박미정 (서울산업대학교 안경광학과) ;
  • 이흠숙 (서울산업대학교 식품공학과)
  • Published : 2007.02.28
Download PDF
⟨ Previous Next ⟩

Abstract

From the total methanolic extract of Chrysanthemum coronarium L. var. spatiosum (Compositae), nitrite scavenging ability and superoxide dismutase (SOD)-like activity were analyzed as antioxidative characteristics. After successive partitioning with chloroform, n-butanol, and water, the chloroform fraction showed the most significant nitrite scavenging ability with an $IC_{50}$ value of 39 ppm compared with the values of vitamin C and chlorogenic acid, 15 ppm and 36 ppm, respectively. The active fraction was subjected to silica gel and Sephadex LH-20 column chromatography, and the compound was isolated and identified as ${\beta}-sitosterol-O-{\beta}-D-glucoside$ using $^{1}H-NMR$ and $^{13}C-NMR$ spectral data. The glucoside was further hydrolyzed and confirmed as a glycosylated ${\beta}-sitosterol$. The compound and its aglycone, ${\beta}-sitosterol$, showed different nitrite scavenging and SOD-like activity. The $IC_{50}$ value of nitrite scavenging ability of the compound was 335 ppm at pH 1.5, while that of its aglycone was 41 ppm. As for the SOD-like activity, the $EC_{50}$ values of the sterol and the glucoside were 1,291 ppm and >2,000 ppm, respectively, compared with those of vitamin C and chlorogenic acid, 38 ppm and 449 ppm, respectively.

쑥갓의 항산화 활성을 알아보기 위해 쑥갓 총 메탄올추출물의 아질산염 소거작용과 SOD 유사활성을 측정하였다. 아질산염 소거작용과 SOD 유사활성을 가지고 있는 총 메탄올 추출물로부터 클로로포름, n-부탄올 및 물 분획물을 제조하여 각각의 활성을 측정하였다. pH가 1.5일 때의 클로로포름 분획물의 $IC_{50}$값은 39ppm으로 가장 우수한 아질산염 소거작용을 보였으며, vitamin C와 chlorogenic acid의 $IC_{50}$값이 15ppm과 36ppm일 때 클로로포름 분획물은 양성대조군인 chlorogenic acid와 동등한 소거작용을 보였다. 아질산염 소거작용에 대하여 유의성 있게 높은 활성을 나타낸 클로로포름 분획물을 silica gel 컬럼크로마토그래피와 sephadex LH-20 컬럼크로마토그래피를 이용하여 분획의 활성성분인 compound I을 분리하였다. 분리된 compound를 $^{1}H-NMR$과 $^{13}C-NMR$ spectral data를 통하여 구조를 동정한 결과 compound I은 ${\beta}-sitosterol-O-{\beta}-D-glucoside$임을 확인하였다. Compound I과 그 aglycone인 ${\beta}-sitosterol$의 아질산염 소거작용과 SOD 유사활성은 다소 차이가 있었다. 양성대조군으로 사용한 vitamin C와 chlorogenic acid의 $IC_{50}$값이 pH 1.5에서 각각 15ppm과 36ppm일때 compound I의 $IC_{50}$값이 335ppm, ${\beta}-sitosterol$의 $IC_{50}$값이 41ppm으로 가수분해된 aglycone이 아질산염 소거작용이 훨씬 높았다. SOD 유사활성의 경우 vitamin C와 chlorogenic acid의 $EC_{50}$ 값은 38ppm, 449ppm으로 이와 비교시 ${\beta}-sitosterol$과 배당체의 $EC_{50}$ 값은 1,291ppm과 2,000ppm 이상으로 나타났다.

Keywords

References

  1. Mazza G, Oomah BD. Herbs, Botanicals and Teas. Technomic Publishing Co. Lancaster, UK. pp. 1-16 (2000)
  2. Cross EE, Halliwell B, Borish ET, Pryor WA, Ames BN, Saul RL, McCord JM. Oxygen radicals and human disease (clinical conference). Ann. Intren. Med. 107: 526-545 (1987)
  3. Kedziora J, Bartosz G. Down's syndrome: a pathway involving the lack of balance of reactive oxygen species. Free Radic. Biol. Med. 4: 317-330 (1988) https://doi.org/10.1016/0891-5849(88)90052-4
  4. Marnett LJ. Peroxyl free radicals: potential mediators of tumor initiation and promotiom. Carcinogenesis 8: 1365-1373 (1987) https://doi.org/10.1093/carcin/8.10.1365
  5. Patt J, Harken AH, Burton LK, Rodell TC, Piermateei D, Schorr WJ, Parker NB, Berger EM, Horesh IR, Terada LS, Linas SI, Cheronis JC, Repine JE. Xanthine oxidase derived hydrogen peroxide contributes to reperfusion induced edema in gebriI brains. J. Clin. Invest. 81: 1556-1562 (1988) https://doi.org/10.1172/JCI113488
  6. MaveIli I, Ciriolo MR, Rotilio G, De Sole P, Castorino M, Stabile A. Superoxide dismutase, glutathione peroxidase and catalase in oxidative hemolysis. A study of Fanconi's anaemia erythrocytes. Biochem. Biophys. Res. Comm. 106: 286-290 (1982) https://doi.org/10.1016/0006-291X(82)91107-X
  7. Walker R. Nitrates, nitrites and N-nitroscompounds: a review of the occurrence in food and diet and the toxicological implications. Food Addit. Contam. 7: 717-768 (1990) https://doi.org/10.1080/02652039009373938
  8. Rorald W. Naturally occurring nitrite in food. J. Jpn. Soc. Food Agric. 26: 1735-1742 (1975) https://doi.org/10.1002/jsfa.2740261116
  9. Kitani K, Minami C, Yamamoto T, Kanai S, Ivy GO, Carrillo MC. Pharmacological interventions in aging and age-associated disorders: potentials of propargylamines for human use. Ann. N. Y. Acad Sci. 959: 295-307 (2002) https://doi.org/10.1111/j.1749-6632.2002.tb02101.x
  10. Lee CB. Illustrated Flora of Korea. Hyangmoonsa, Seoul, Korea. p. 753 (1982)
  11. Harborne JB, Heywood VH, Saleh NAM. Chemosystematics of the Compositae: flavonoid patterns in the Chrysanthemum complex of the tribe Anthemideae. Phytochemistry 9: 2001-2017 (1970)
  12. Sanz JF, Falco E, Marco JA. New acetylenes from Chrysanthemum coronarium L. Liebigs. Ann. Chem. 303-305 (1989)
  13. Jang DS, Nam SH, Choi SU, Jang MS. Antibacterial activity of Chrysanthemum spp. Agr. Chem. BiotechnoI. 39: 315-319 (1996)
  14. Jang DS, Park KH, Kim HM, Hong DH, Chun HK, Kho YH, Yang MS. Biological activities of sesquiterpene lactones isolated from several Compositae plants. Part I. Cytotoxicity against cancer cell lines. Korean J. Pharmacogn. 29: 243-247 (1998)
  15. Chuda Y, Suzuki M, Nagata T, Tsushida T. Contents and cooking loss of three quinic acid derivatives from garland (Chrysanthemum coronarium L.). J. Agr. Food Chem. 46: 1437-1439 (1998) https://doi.org/10.1021/jf9708554
  16. Kee CH. The pharmacology of chinese herbs. CRC Press, Boca Raton, FL, USA. pp. 74-98 (1993)
  17. Kang HJ, Lee EJ, Sung SH, Kim YC, Song ES, Park MJ, Lee HS. Anti-hepatotoxic activity of Chrysanthemum coronarium L. var. spatiosum extract. Korean J. Food Sci. Technol. 35: 138-143 (2003)
  18. Kato H, Lee IE, Chuyen NV, Kim SB, Hayase F. Inhibition of nitrosamine formation by nondialyzable melanoidins. Agr. BioI. Chem. 51: 1333-1338 (1987) https://doi.org/10.1271/bbb1961.51.1333
  19. Peri L, Pietraforte D, Scorza G, Napolitano A, Fogliano V, Minetti M. Apples increase nitric oxide production by human saliva at the acidic pH of the stomach: a new biological function for polyphenols with a catechol group? Free Radic. BioI. Med. 39: 668-681 (2005) https://doi.org/10.1016/j.freeradbiomed.2005.04.021
  20. Bae RN, Lee SK. Factors affecting browning and its control methods in chopped garlic. J. Korean Soc. Hort. Sci. 31: 213-218 (1990)
  21. Jo KS, Kim HK, Ha JH, Park MH, Shin HS. Flavor compounds and storage stability of essential oil from garlic distillation. Korean J. Food Sci. Technol. 22: 840-845 (1990)
  22. Marklund S, Marklund G. Involvement of superoxide anion radical in the oxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur. J. Biochem. 47: 469-474 (1974) https://doi.org/10.1111/j.1432-1033.1974.tb03714.x
  23. Nakatani N, Kayano S, Kikuzaki H, Sumino K, Katagiri K, Mitani T. Identification, quantitative determination and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica.). J. Agr. Food Chem. 48: 5512-5516 (2000) https://doi.org/10.1021/jf000422s
  24. Kang BR, Park M, Lee HS. Germination dependency of antioxidative activities in brown rice. J. Korean Soc. Food Sci. Nutr. 35: 389-394 (2006) https://doi.org/10.3746/jkfn.2006.35.4.389
  25. Pouchert CJ, Behnke J. The Aldrich library of $^{13}C$ and $^1H-FT NMR spectra. Aldrich Chemical Company. Milwaukee, WI, USA. 3: 568-569 (1993)
  26. Do JC, Chai JY, Son JK. Studies on the constituents of Lycopus lucidus (II). Korean J. Pharmacogn. 22: 166-170 (1991)
  27. Awad AB, Fink CS, Trautwein EA, Ntanios FY. ${\beta}$-Sitosterol stimulates ceramide metabolism in differentiated $CaCO_2$ cells. J. Nutr. Biochem. 16: 650-655 (2005) https://doi.org/10.1016/j.jnutbio.2005.04.004
  28. Vivancos M, Moreno JJ. ${\beta}$-Sitosterol modulates antioxidant enzyme response in RAW 264.7 macrophages. Free Radic. BioI. Med. 39: 91-97 (2005) https://doi.org/10.1016/j.freeradbiomed.2005.02.025
  29. Su BN, Pawlus AD, Jung HA, Keller WJ, McLaughlin JL, Kinghorn AD. Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity. J. Nat. Prod. 68: 592-595 (2005) https://doi.org/10.1021/np0495985