Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Development of Biologically Active Compounds from Edible Plant Sources XXII. Isolation of Indoles from the Roots of Brassica campestris ssp rapa and their hACAT Inhibitory Activity

식용식물자원으로부터 활성물질의 탐색 XXII. 순무(Brassica campestris ssp rapa) 뿌리로부터 인돌 화합물의 분리 및 hACAT 저해 활성

  • Bang, Myun-Ho (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Lee, Dae-Young (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Oh, Young-Jun (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Han, Min-Woo (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Yang, Hye-Joung (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Chung, Hae-Gon (Ganghwa Agricultural R&D Center) ;
  • Jeong, Tae-Sook (National Research Laboratory of Lipid Metabolism & Atherosclerosis, KRlBB) ;
  • Lee, Kyung-Tae (Department of Biochemistry, College of Pharmacy, Kyung Hee University) ;
  • Choi, Myung-Sook (Department of Food Science and Nutrition, Kyungpook National University) ;
  • Baek, Nam-In (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University)
  • 방면호 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 이대영 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 오영준 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 한민우 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 양혜정 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 정해곤 (강화군 특화작목연구소) ;
  • 정태숙 (한국생명공학연구원 지질대사연구실) ;
  • 이경태 (경희대학교 약학대학) ;
  • 최명숙 (경북대학교 식품영양학과) ;
  • 백남인 (경희대학교 생명공학원 및 식물대사연구센터)
  • Published : 2008.03.31
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Abstract

The roots of Brassica campestris ssp rapa were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$. From the EtOAc fraction, three compounds were isolated through the repeated silica gel and octadecyl silica gel (ODS) column chromatography. From the results of spectroscopic data including NMR and MS, the chemical structures of the compounds were determined as caulilexin C (1), indoleacetonitrile (2) and arvelexin (3). The arvelexin (3) has been isolated from this plant for the first time. Compounds 1, 2 and 3 showed inhibitory activity on human Acyl CoA: cholesterol. transferase 1 (hACAT1) by $54.6{\pm}6.0%$, $69.2{\pm}4.7%$ and $68.6{\pm}3.7%$, and on human Acyl CoA: cholesterol transferase 2(hACAT2) by $4.8{\pm}13.4%$, $45.6{\pm}4.8%$ and $39.5{\pm}4.3%$, respectively, at 100 ${\mu}g/ml$.

순무 뿌리로부터 80% MeOH 수용액으로 추출하고 이를 여과, 감압 농축하여 MeOH추출물을 얻었다. 이를 EtOAc 분획, n-BuOH분획, $H_2O$분획으로 나누었으며, EtOAc분획으로부터 silica gel 및 ODS column chromatography를 실시하여 3종의 화합물을 분리 정제하였다. 각각에 대하여 $^1H-NMR$, $^{13}C-NMR$, DEPT 스펙트럼 및 Mass 스펙트럼 데이터를 해석하여, caulilexin C (1), indoleacetonitrile (2) 및 arvelexin (3)로 구조를 결정하였다. 화합물 3는 순무에서는 이번에 처음 분리, 보고되었다. 또한 화합물 1, 2, 및 3은 100 ${\mu}g/ml$의 농도에서 hACATl의 활성을 각각 $54.6{\pm}6.0%$, $69.2{\pm}4.7%$ 및 $68.6{\pm}3.7%$ 억제하였고, hACAT2의 활성을 각각 $4.8{\pm}13.4%$, $45.6{\pm}4.8%$ 및 $39.5{\pm}4.3%$ 억제하였다.

Keywords

References

  1. Kang, I. H. (1991) History of Culture in Korea (II). Samyangsa. Seoul. Korea. p 197
  2. Jung, B. S. and Shin, M. K. (1990) In Hyang Yak Dae Sa Jun. Young Lim Sa. Seoul, Korea. p 574
  3. Itoh, H., Yoshida, R., Mizuno, T., Kudo, M., Nikuni, S. and Karki, T. (1984) Study on the contents of volatile isothiocyanate of cultivars of Brassica vegetables. Report of the National Food Research Institute, 45, 33-41
  4. Ju, H., Chong, C., Mullin, W. and Bilble, B. (1982) Volatile isothiocyanates and nitriles from glucosinolates in rutabaga and turnip. J. Am. Soc. Hort. Sci. 107, 1050-1054
  5. Sones, K., Heaney, R. and Fenwick, G. (1984) An estimate of the mean daily intake of glucosinolates from cruciferous vegetables in the UK. J. Sci. Food Agric. 35, 712-720 https://doi.org/10.1002/jsfa.2740350619
  6. Wilkinson, A., Rhodes, M. and Fenwick, R. (1984) Myrosinase activity of cruciferous vegetables. J. Sci. Food. Agric. 35, 543- 552 https://doi.org/10.1002/jsfa.2740350511
  7. Kim, J. S., Choi, Y. H., Seo, J. H., Lee, J. W., Kim, Y. S., Ryu, S. Y., Kang, J. S., Kim, Y. K. and Kim, S. H. (2004) Chemical constituents from the Root of Brassica campestris ssp rapa. Kor. J. Pharmacogn. 35, 259-263
  8. Cho, K. H., An, S., Lee, W. S., Paik, Y. K., Kim, Y. K., and Eong, T. S. (2003) Mass-production of human ACAT-1 different substrate specificity and inhibitory regulation. Biochem. Biophys. Res. Commun. 309, 864-872 https://doi.org/10.1016/j.bbrc.2003.08.077
  9. Brecher, P. and Chan, C. T. (1980) Properties of acyl- CoA:cholesterol O-acyltransferase in aortic microsomes from atherosclerotic rabbits. Biochem Biophys Acta 1617, 458-471
  10. Kim, S. J., Choi, Y. H., Seo, J. H., Lee, J. W., Kim, Y. S., Ryu, S. Y., Kang, J. S., Kim, Y. K. and Kim, S. H. (2004) Chemical constituents from the root of Brassica campestris ssp rapa. Kor. J. Pharmacogn. 35, 259-263
  11. Mitsuo, M., Tomoko, N. and Chikako, Y. (2005) Volatile components of the leaves of Brassica rapa L. var. perviridis Bailey. Flavour Fragr. J. 20, 158-160 https://doi.org/10.1002/ffj.1335
  12. Pedras, M. S. C., Chumala, P. B. and Suchy, M. (2003) Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity. Phytochemistr 64, 949-956 https://doi.org/10.1016/S0031-9422(03)00441-2
  13. Chang, T. Y., Chang, C. Y. and Cheng, D. (1997) Acylcoenzyme A: cholesterol acyltransferase, Annu. Rev. Biochem. 66, 613-638 https://doi.org/10.1146/annurev.biochem.66.1.613
  14. Rudel, L. L., Lee, R. G. and Cockman, T. L. (2001) Acylcoenzyme A: cholesterol acyltransferase types 1 and 2: structure and function in atherosclerosis, Curr. Opin. Lipidol. 12, 121-127 https://doi.org/10.1097/00041433-200104000-00005
  15. Accad, M., Smith, S. J., Newland, D. L., Sanan, D. A., King, L. E., Linton, M. F., Fazio, S. and Farese, R. V. Massive xanthomatosis and altered composition of atherosclerotic lesions in hyperlipidemic mice lacking acyl CoA:cholesterol acyltransferase 1. J. Clin. Invest. 105, 711-719 https://doi.org/10.1172/JCI9021
  16. Ahn, E. M., Bang, M. H., Song, M. C., Park, M. H., Kim, H. Y., Kwon, B. M. and Baek, N. I. (2006) Cytotoxic and ACATinhibitory sesquiterpene lactones from the root of Ixeris dentata forma albiflora. Arch. Pharm. Res. 29, 937-941 https://doi.org/10.1007/BF02969274
  17. Yang, H. J., Song, M. J., Bang, M. H., Lee, J. H., Chung, I. S., Lee, Y. H., Jeong, T. S., Kwon, B. M., Kim, S. H., Kim, D. K., Park, M. H. and Baek, N. I. (2005) Development of Biologically Active Compounds from Edible Plant Sources XII. Flavovol glycosides from Trigonotis peduncularis Benth and its hACAT1 inhivitory activity. Koran Soc. Appl. Biol. Chem. 48, 98-102
  18. Loub, W. D., Wattenberg, L. W. and Davis, D. W. (1975) Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferous plants. J. Natl. Cancer. Inst. 54, 985-988
  19. Maskell, I. and Smithard, R. (1994) Degradation of glucosinolates during in vitro incubations of rapeseed meal with myrosinase (EC 3.2.3.1) and with pepsin (EC 3.4.23.1) hydrochloric acid and contents of porcine small intestine and caecum. Br. J. Nutr. 72, 455-466 https://doi.org/10.1079/BJN19940047