Isolation and identification of lignans as Antioxidant from loaves of Catalpa ovata G. $D_{ON}$

개오동나무 잎으로부터 항산화 활성을 갖는 lignan 화합물의 분리 및 동정

  • 국주희 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 마승진 ;
  • 문제학 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 박근형 (전남대학교 식품공학과 및 농업과학기술연구소)
  • Published : 2003.12.01

Abstract

The methanol extract from leaves of Catalpa ovata 6. DoN showed DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging activity, and its antioxidative compounds were studied. The ethyl acetate-soluble neutral fraction from the methanol extract was successively purified with silica gel adsorption column chromatography, Sephadex LH-20 column chromatography and HPLC. Three antioxidative compounds were isolated and identified as piperitol, pinoresinol and lariciresinol by HR-MS and NMR spectroscopic analyses. The DPPH radical-scavenging activity of the identified compounds decreased in the order of lariciresinol > pinoresinol > piperitol.

개오동나무 (Catalpa ovata G. Don) 잎의 MeOH 추출물은 DPPH 라디칼 소거활성을 나타냈으며, 이에 개오동나무 잎에 함유된 항산화물질을 구명하고자 하였다. MeOH 추출물을 용매분획하여 EtOAc 가용 중성획분을 얻고, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography로 정제한 다음 HPLC에 의해 3종의 활성물질을 단리하였다. 단리된 물질들은 HR-MS, 1H-NMR, 13C-NMR, 2D-NMR 등의 기기분석에 의해 piperitol, pinoresinol, lariciresinol로 동정하였다. 이들 물질들을 대상으로 DPPH 라디칼 소거활성을 조사한 결과, lariciresinol ($SC_{50}$/, 19$\mu\textrm{g}$/mL) > pinoresinol ($SC_{50}$/, 31$\mu\textrm{g}$/mL) > piperitol ($SC_{50}$/, 59$\mu\textrm{g}$/mL)의 순으로 항산화활성이 나타났다.

Keywords

References

  1. Trends in Food Sci. Technol v.6 The contribution of plant food antioxidants to human health Ramarathnam,N.;T.Osawa;H.Ochi;S.Kawakishi https://doi.org/10.1016/S0924-2244(00)88967-0
  2. Nat. Prod. Rep. Dietary antioxidants in disease prevention Gordon,M.H.
  3. J. Am. Oil Chem. Soc. v.52 Toxicological and biochemistry of butylated hydroxytoluene, butylated hydroxyanisole Branen,A.L. https://doi.org/10.1007/BF02901825
  4. J. Wood Research Soc. Jpn. v.8 The chemistry of wood extractives. Ⅲ. Constinuents of Catalpa ovata G.Don Imamura,H.;M.Suda
  5. J. Nat. Prod. v.61 Antitumor-promoting naphthoquinones from Catalpa ovata Fujiwara,A.;T.Mori;A.Iida;S.Ueda;Y.Hano;T.Nomura;H.Tokuda;H.Nishino https://doi.org/10.1021/np9800147
  6. Chem. Pharm. Bull. v.49 Studies on the constituents of Catalpa species.Ⅵ. Monoterpene glycosides from the fallen leaves of Catalpa ovata G. Don Machida,K.;M.Ando;Y.Yaoita;R.Kakuda;M.Kikuchi https://doi.org/10.1248/cpb.49.732
  7. Phytochemistry v.14 Two new flavone glycosides from Catalpa ovata Okuda,T.;T.Yoshida;I.Ono https://doi.org/10.1016/0031-9422(75)85376-3
  8. Chem. Pharm. Bull. v.46 Studies on the constituents of Catalpa species. Ⅱ. Iridoids from catalpae fructus Machida,K.;M.Ogawa;M.Kikuchi https://doi.org/10.1248/cpb.46.1056
  9. J. Microbiol. Biotechnol. v.12 Antibacterial and antifungal activities of a naphthoquienone derivative isolated from the fruits fo Catalpa ovata G.Don Kuk,J.H.;S.J.Ma;J.H.Moon;K.Y.Kim;S.H.Choi;K.H.Park
  10. Nature v.181 Antioxidant determinations by the use of a satble free radical Blois,M.S. https://doi.org/10.1038/1811199a0
  11. Biosci. Biotech. Biochem. v.58 A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish Takao,T.;F.Kitatani;N.Watanabe;A.Yagi;K.Sakata https://doi.org/10.1271/bbb.58.1780
  12. Nat. Prod. Rep. Lignans, neolignans, and related compounds Ward,R.S.
  13. Tetrahedron Lett. v.35 (+)-Pinoresinol synthase: a stereoselective oxidase catalysing 8,8'-lignan formation in Forsythia intermedia Pare,P.W.;H.B.Wang;L.B.Davin;N.G.Lewis https://doi.org/10.1016/S0040-4039(00)76953-X
  14. Tetrahedron Lett. v.26 Four new lignans from Aptosimum spinescens(Thunbg.) Brieskom,C.H.;H.Huber
  15. Planta Med. v.53 (+)-Priperitol from Paulownia tomentosa Ina,H.;M.Ono;Y.Sashida;H.Iida https://doi.org/10.1055/s-2006-962791
  16. Phytochemistry v.47 Biosynthesis of antioxidant lignans in Sesamum indicum seeds Kato,M.J.;A.Chu;L.B.Davin;N.G.Lewis https://doi.org/10.1016/S0031-9422(97)00727-9
  17. KJWS v.9 The search for naturally occuring herbicidal compounds. Ⅱ. Isolation of pinoresimol from Rhathiolepis ovata Briat and its biological activity Ahn,J.W.;J.S.Choi;K.Y.Cho
  18. Phytochemistry v.49 Antioxidative activities of constituents isolated from Pandanus odoratissimus Jong,T.T.;S.W.Chau https://doi.org/10.1016/S0031-9422(98)00390-2
  19. Phytochemistry v.31 Antimicrobial activities of the lignans from Abies koreana Wilson Kim,Y.G.;J.S.Jo;C.K.Moon
  20. Biosci. Biotech. Biochem. v.56 Structure of novel antioxidative lignan glucosides isolated from sesame seed Katsuzaki,H.;M.Kawasumi;S.Kawakishi;T.Osawa https://doi.org/10.1271/bbb.56.2087
  21. Nippon Shokuhin Kagaku Kogaku Kaishi v.46 Antioxidative lignans from industrial wastewater in cleaning of black sesame seed Nagashima,M.;Y.Fukuda;R.Ito https://doi.org/10.3136/nskkk.46.382
  22. Anticancer Res. v.15 Discovery of natural product chemopreventive agents utilizing HL-60 cell differentiation as a model Suh,N.;L.lutengi;H.H.S.Fong;A.D.Kinghorn;J.M.Pezzuto
  23. Plant Growth Regulation v.37 Isolation and identification of plant growth inhibitors as candidate for allelopathic substance from aqueous leachate from mesquite (Prosopis juliflora (Sw.) DC) leaves Kiroshi,N.;F.Yoshiharu;Y.Kosumi;K.Seiji;Y.Shosuke;H.Koji;S.Takahisa https://doi.org/10.1023/A:1020579101938
  24. Natural Med. v.54 Analysis of gastric mucous membrane-protective compounds in Coptidis rhizoma Hiroyuki,H.;T.Takashi;Y.Yukako;Y.Toshio;S.Tetsuro