Deveolopment of Biologically Active Compounds from Edible Plant Sources-VI - Isolation of Sterol Compounds from the Aerial Parts of Garland (Chrysanthemum coronarium L.) -

식용식물자원으로부터 활성물질의 탐색-VI - 쑥갓(Chrysanthemum coronarium L.)으로부터 sterol의 분리 -

  • Song, Myoung-Chong (Graduate School of Biotechnology & Plant Metabolism Research Center, KyungHee University) ;
  • Hong, Yoon-Hee (Graduate School of Biotechnology & Plant Metabolism Research Center, KyungHee University) ;
  • Kim, Dong-Hyun (Graduate School of Biotechnology & Plant Metabolism Research Center, KyungHee University) ;
  • Kim, Dae-Keun (Department of Pharmacy, Woosuk University) ;
  • Chung, In-Sik (Graduate School of Biotechnology & Plant Metabolism Research Center, KyungHee University) ;
  • Lee, Youn-Hyung (Graduate School of Biotechnology & Plant Metabolism Research Center, KyungHee University) ;
  • Kim, Sung-Hoon (Graduate School of East-Weat Medical Science, KyungHee University) ;
  • Park, Mi-Hyun (Erom Life Co. Ltd.) ;
  • Kim, In-Ho (Korea Food Research Institute) ;
  • Kwon, Byoung-Mog (Korea Research Institute of Bioscience & Biotechnology) ;
  • Baek, Nam-In (Graduate School of Biotechnology & Plant Metabolism Research Center, KyungHee University)
  • 송명종 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 홍윤희 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 김동현 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 김대근 (우석대학교 약학대학) ;
  • 정인식 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 이윤형 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 김성훈 (경희대학교 동서의학대학원) ;
  • 박미현 ((주)이롬라이프) ;
  • 김인호 (한국식품개발연구원) ;
  • 권병옥 (한국생명공학연구원) ;
  • 백남인 (경희대학교 생명공학원 및 식물대사연구센터)
  • Published : 2003.11.30

Abstract

The aerial parts of tile Garland (Chrysanthemum comnarium L.) were extracted in MeOH and solvent fractionated with EtOAc, n-BuOH and water, successively. EtOAc fractions gave three steroid compounds through application of silica gel column chromatographies. The chemical structures of the steroids were determined by the interpretation of several spectral data, including NMR and MS as $stigmast-5-en-3{\beta}-ol\;(1,\;{\beta}-sitosterol),\;stigmast-4-en-6{\beta}-ol-3-one$ (2), $stigmast-4-en-6{\alpha}-ol-3-one$ (3). Compounds 2 and 3 have been so far reported only in the aquatic plants, were isolated for the first time from the land plants.

쑥갓의 지상부를 MeOH로 추출하고, 추출물을 EtOAc, n-BuOH 및 물로 분배, 추출하였다. EtOAc 분획으로부터 silica gel column chromatography를 반복하여 3종의 sterol을 분리하였다. 각각의 화학구조는, NMR및 MS등의 스펙트럼을 해석하여, $stigmast-5-en-3{\beta}-ol\;(1,\;{\beta}-sitosterol),\;stigmast-4-en-6{\beta}-ol-3-one$ (2), $stigmast-4-en-6{\alpha}-3-one$ (3)으로 동정하였다. 화합물 2와 3은 육상식물에서는 처음으로 분리되었다.

Keywords

References

  1. Baek, N.-I., Ahn, E. M., Bang, M. H. and Kim, H. Y. (1997) Deveolopment of biologically active compounds from edible plant sources-I. Isolation of major components from the tuber of Ipomoea batatas Lam. J. Korean Soc. Agric. Chem. Biotechnol. 40, 583-587
  2. Han, J. T., Ahn, E. M. and Baek, N.-I. (1999) Deveolopment of biologically active compounds from edible plant sources-II. Isolation of fatty acids and sterol glycosides from the leaves of Cucurbita moschata DUCH. J. Korean Soc. Agric. Chem. Biotechnol. 42, 267-270
  3. Ahn, E. M., Jang, T. H. and Baek, N.-I. (2000) Deveolopment of biologically active compounds from edible plant sources-III. Isolation of flavonoid-glycosides from the Allium monanthum Max. J. Korean Soc. Agric. Chem. Biotechnol. 43, 314-316
  4. Baek, N.-I., Ahn, E. M., Kim, H. Y., Park, Y. D., Chang, Y. J. and Kim S. Y. (2001) Deveolopment of biologically active compounds from edible plant sources-IV. Isolation of galactosyldiglycerides from the Allium monanthum Max. Korean J. Life Sci. 11, 93-96
  5. Jang, T. O., Bang, M. H., Song, M. C., Hong, Y. H., Kim, J. Y, Chung, D. K., Pai, T. K., Kwon, B. M., Kim, Y. K., Lee, H. S., Kim, I. H. and Baek, N.-I. (2003) Deveolopment of biologically active compounds from edible plant sources-V. Phytol, ACAT (Acyl-CoA;Cholesterol Acyltransferase) inhibitory diterpenoid from the leaves of Lactuca sativa L. J. Korean Soc. Agric. Chem. Biotechnol. 42, 267-270
  6. Jung, E. B. and Shin, M. K. (1990) In 'Hyang Yak Dae Sa Jun', Young Lim Sa(3rd ed.), Seoul, Korea
  7. Kameoka, H., Kitagawa, C. and Husebe, Y. (1975) The constituents of the steam volatile oil from Chrysanthemum coronalrium L. var spatiosum. J. Agri. Chem. Soc. Japan 49, 652-657
  8. Anyos, T. and Steelink, C. (1960) Fluresent petal constituents of Chrysanthemum cormnarium L. Arch. Biochem. Biophys. 90, 63-67 https://doi.org/10.1016/0003-9861(60)90612-3
  9. Bohlmann, F. and Fritz, U. (1979) Neue lyratolester aus chrysanthemum coronarium. Phytochem. 18, 1888-1889 https://doi.org/10.1016/0031-9422(79)83083-6
  10. Sanz, J. F., Falco, E. and Marco, J. A. (1990) New acetylenes from Chrysanthemum coronarium L. Liebigs Ann. Chem. 90, 303-305
  11. Mahahiro, T. and Kazuhiro, C. (1984) Novel plant growth inhibitors and an insect antifeedant from Chrysanthemum coronarium L. Agric. Biol. Chem. 48, 1367-1369 https://doi.org/10.1271/bbb1961.48.1367
  12. Greca, M. D., Monaco, P. and Previtera, L. (1990) Stigmasterols from Typha latifolia. J. Nat. Prod. 53, 1430-1435 https://doi.org/10.1021/np50072a005
  13. James, A. and Svoboda. (1994) Steroid metabolism as a target for insect control. Lipid Biochem. Pesti. Act. 22