Phenylpropanoids from Myristica fragrans Houtt

육두구(Myristica fragrans Houtt)로부터 Phenylpropanoid의 분리

  • Song, Myoung-Chong (Biotechnology Graduate School & Plant Metabolism Research Center) ;
  • Ahn, Eun-Mi (Biotechnology Graduate School & Plant Metabolism Research Center) ;
  • Bang, Myun-Ho (Biotechnology Graduate School & Plant Metabolism Research Center) ;
  • Kim, Se-Young (Department of Oriental Medicinal Materials.Processing & Oriental Medicinal Materials.Processing Center, KyungHee University) ;
  • Rho, Yeong-Deok (Department of Oriental Medicinal Materials.Processing & Oriental Medicinal Materials.Processing Center, KyungHee University) ;
  • Kwon, Byuong-Mog (Korea Research Institute of Bioscience & Biotechnology) ;
  • Lee, Hyun-Sun (Korea Research Institute of Bioscience & Biotechnology) ;
  • Baek, Nam-In (Biotechnology Graduate School & Plant Metabolism Research Center)
  • 송명종 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 안은미 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 방면호 (경희대학교 생명공학원 및 식물대사연구센터) ;
  • 김세영 (경희대학교 한방재료가공학과 및 한방재료가공센터) ;
  • 노영덕 (경희대학교 한방재료가공학과 및 한방재료가공센터) ;
  • 권병목 (한국생명공학연구원) ;
  • 이현선 (한국생명공학연구원) ;
  • 백남인 (경희대학교 생명공학원 및 식물대사연구센터)
  • Published : 2004.09.30

Abstract

Myristica fragrans Houtt were extracted in 80% aq. MeOH and solvent fractionated sing $CHCl_3$, EtOAc, n-BuOH and water, successively. The n-BuOH fraction gave three phenylpropanoids through application of silica gel column chromatographies. The chemical structures of the phenylpropanoids were determined by the interpretation of several spectral data, including NMR and MS as meso-dihydroguaiaretic acid (1), nectandrin B (2) and syringin methyl ether (3). Compound 1, which was first isolated from this plant by authors, showed inhibitory activities with $60.0{\pm}2.1%\;(100\;{\mu}g/ml),\;42.6{\pm}0.9%\;(140\;{\mu}g/ml)\;and\;12.2{\pm}0.2%\;(200\;{\mu}g/ml)$ on ACAT(acyl-CoA:Cholesterol Acyltransferase), chitin synthase III and HMG-CoA reductase (3-hydroxy-3-methylglutaryl coenzyme A reductase), respectively. Compound 3 showed inhibitory activities with $27.2{\pm}0.9%\;(100\;{\mu}g/ml),\;45.5{\pm}0.8%\;(200\;{\mu}g/ml)$ on ACAT and chitin synthase III.

Keywords

References

  1. Herath, H. M. T. and Priyadarshani, A. M. A. (1996) Lignans from Myristica dactyloides. Phytochemistry 44, 699-703
  2. Hattori, M., Hada, S., Kawata, Y., Tezuka, Y., Kikuchi, T. and Namba, T. (1987) New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans. Chem. Phann. Bull. 35, 3315-3322 https://doi.org/10.1248/cpb.35.3315
  3. Harbome, J. B., Heywood, V. H. and Williams, C. A. (1969) Distribution of myristicin of the Umbelliferae. Phytochemistry 8, 1729-1732 https://doi.org/10.1016/S0031-9422(00)85960-9
  4. Filleur, E, Bail, 1. C., Duroux, J. L., Simon, A. and Chulia, A. I. (2001) Antiproliferative, anti-aromatase, anti-17~-HSD and antioxidant activities of lignans isolated from Myristica arentea. Planta Med. 67, 700-704 https://doi.org/10.1055/s-2001-18349
  5. Sugiyama, M., Nagayama, E. and Kikuchi, M. (1993) Lignan and phenylpropanoid glycosides from Osmanthus asiaticus. Phytochemistry 33, 1215-1219 https://doi.org/10.1016/0031-9422(93)85052-S
  6. Ericson, S. K., Shrewbery, M. A., Brooks, C. and Meyer, D. 1. (1980) Rat liver acyl-coenzyme A: cholesterol acyltransferase: its regulation in vivo and some of its properties in vitro. J. Lipid Res. 21, 930-941
  7. Jang, T. 0., Bang, M. R., Song, M. Ch., Hong, Y. R., Kim, I. Y., Chung, D. K., Pai, T. K., Kwon, B. M., Kim, Y. K., Lee, R. S., Kim, 1. 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
  8. Kleisek, D. A., Dugan, R. E., Baker, T. A. and Porter J. W. (1981) 3-Hydroxy-3-methylglutaryl coenzyme A reductase from rat liver. Methods Enzymol. 71, 462-479 https://doi.org/10.1016/0076-6879(81)71057-7
  9. Jeung, T. S., Hwang, E. 1., Lee, H. B., Lee, E. S., Kim, Y. K., Min, B. S., Bae, K. H., Bok, S. H. and Kim, S. U. (1999) Chitin synthase III inhibitory activity of ursolic acid isolated from Crataegus pinnatifida. Planta Med. 65, 261-263 https://doi.org/10.1055/s-2006-960474