DOI QR코드

DOI QR Code

Qualitative and Quantitative Analysis of Dibenzocyclooctadiene Lignans for the Fruits of Korean "Omija" (Schisandra chinensis)

한국산 오미자로부터 디벤조사이클로옥타디엔 계열 리그난 화합물 정성 및 정량 분석

  • 김헌웅 (농촌진흥청 국립농업과학원) ;
  • 신재형 (농촌진흥청 국립농업과학원) ;
  • 이민기 (농촌진흥청 국립농업과학원) ;
  • 장가희 (농촌진흥청 국립농업과학원) ;
  • 이성현 (농촌진흥청 국립농업과학원) ;
  • 장환희 (농촌진흥청 국립농업과학원) ;
  • 정석태 (농촌진흥청 국립농업과학원) ;
  • 김정봉 (농촌진흥청 국립농업과학원)
  • Received : 2015.07.30
  • Accepted : 2015.09.08
  • Published : 2015.10.30

Abstract

Background : Dibenzocyclooctadiene lignans are secondary metabolites present abundantly in the fruits belonging to the genus Schisandra. According to previous studies, Schisandra lignans exhibit anti-inflammatory, anti-cancer and anti-diabetic properties, as well as an inhibitory effect on platelet aggregation. Therefore, establishing the Korean "Omija" (Schisandra chinensis) as a lignan-rich source, in addition to identifying and quantifying the lignans, is extremely valuable. Methods and Results : Dibenzocyclooctadiene lignans were analyzed with liquid chromatography using diode array detection/mass spectrometry, from methanol extracts subsequently identified by a constructed chemical library of 50 lignans. A total of 27 components of lignan including gomisin S were identified, of which schisandrin, gomisin A, gomisin N, deoxyschisandrin, ${\gamma}$-schisandrin, and schisandrin C were identified as the major components in the Korean Omija, Schisandra chinensis. These compounds were divided into two groups, S-biphenyl and R-biphenyl based on the configurations of the stereoisomers structures with contents of 661.7 and 1350.1mg per 100 g dry weight, respectively. The total lignan content averaged 2011.4mg per 100 g dry weight, of which schisandrin and gomisin N comprised the majority (771.8 and 420.5mg per 100 g dry weight respectively). Conclusions : Lignans which are present in high quantities in the ripe fruit of Schisandra chinensis are important functional compounds that play a major role in the prevention and treatment of human diseases.

Keywords

References

  1. Chang GT, Kang SK, Kim JH, Chung KH, Chang YC and Kim CH. (2005). Inhibitory effect of the Korean herbal medicine, Dae-Jo-Whan, on platelet activating factor induced platelet aggregation. Journal of Ethnopharmacology. 102:430-439. https://doi.org/10.1016/j.jep.2005.07.003
  2. Deng X, Chen X, Cheng W, Shen Z and Bi K. (2008). Simultaneous LC-MS quantification of 15 lignans in Schisandra chinensis(Turcz.) Baill fruit. Chromatographia. 67:559-566. https://doi.org/10.1365/s10337-008-0589-3
  3. Gu BH, Minh NV, Lee SH, Lim SW, Lee YM, Lee KS and Kim DK. (2010). Deoxyschisandrin inhibits $H_2O_2$ induced apoptotic cell death in intestinal epithelial cells through nuclear factor KB. International Journal of Molecular Medicine. 26:401-406.
  4. Guo LY, Hung TM, Bae KH, Shin EM, Zhou HY, Hong YN, Kang SS, Kim HP and Kim YS. (2008). Anti-inflammatory effects of schisandrin isolated from the fruit of Schisandra chinensis Baill. European Journal of Pharmacology. 591:293-299. https://doi.org/10.1016/j.ejphar.2008.06.074
  5. He XG, Lian LZ and Lin LZ. (1997). Analysis of lignan constituents from Schisandra chinensis by liquid chromatographyelectrospray mass spectrometry. Journal of Chromatography A. 757:81-87. https://doi.org/10.1016/S0021-9673(96)00685-1
  6. Huang T, Shen P and Shen Y. (2005). Preparative separation and purification of deoxyschisandrin and γ-schisandrin from Schisandra chinensis(Turcz.) Baill by high-speed counter-current chromatography. Journal of Chromatography A. 1066:239-242. https://doi.org/10.1016/j.chroma.2005.01.025
  7. Huang TL, Lin JCT, Chyau CC, Lin KL and Chang CMJ. (2013). Purification of lignans from Schisandra chinensis fruit by using column fractionation and supercritical antisolvent precipitation. Journal of Chromatography A. 1282:27-37. https://doi.org/10.1016/j.chroma.2013.01.091
  8. Ikeya Y, Taguchi H and Yosioka I. (1978). The constituents of Schizandra chinensis Baill. The structures of two new lignans, pre-gomisin and gomisin. Journal of Chemical and Pharmaceutical Bulletin. 26:682-684. https://doi.org/10.1248/cpb.26.682
  9. Ikeya Y, Taguchi H, Yosioka I and Kobayashi H. (1979a). The constituents of Schizandra chinensis Baill. III. The structures of four new lignans, gomisin H and its derivatives, angeloyl-,tigloyl- and benzoyl-gomisin H. Chemical and Pharmaceutical Bulletin. 27:1576-1582. https://doi.org/10.1248/cpb.27.1576
  10. Ikeya Y, Taguchi H, Yosioka I and Kobayashi H. (1979b). The constituents of Schizandra chinensis Baill. V. The structures of four new lignans, gomisin N, gomisin O, epigomisin O and gomisin E, and transformation of gomisin N to deangeloylgomisin B. Chemical and Pharmaceutical Bulletin. 27:2695-2709. https://doi.org/10.1248/cpb.27.2695
  11. Ikeya Y, Taguchi H and Yosioka I. (1979c). The constituents of Schizandra chinensis Baill. The cleavage of the methylenedioxy moiety with lead tetraacetate in benzene, and the structure of angeloylgomisin Q. Chemical and Pharmaceutical Bulletin. 27:2536-2538. https://doi.org/10.1248/cpb.27.2536
  12. Ikeya Y, Taguchi H and Yosioka I. (1980a). The constituents of Schizandra chinensis Baill. VII. The structures of three new lignans, (−)-gomisin $K_1$ and (+)-gomisins $K_2$ and $K_3$. Chemical and Pharmaceutical Bulletin. 28:2422-2427. https://doi.org/10.1248/cpb.28.2422
  13. Ikeya Y, Taguchi H, Yosioka I and Kobayashi H. (1980b). The constituents of Schizandra chinensis Baill. VIII. The structures of two new lignans, tigloylgomisin P and angeloylgomisin P. Chemical and Pharmaceutical Bulletin. 28:3357-3361. https://doi.org/10.1248/cpb.28.3357
  14. Ikeya Y, Taguchi H and Yosioka I. (1982a). The constituents of Schizandra chinensis Baill. VII. The structures of γ-schizandrin and four new lignans, (−)-gomisin $L_1$ and $L_2$, $({\pm})$-gomisins $M_1$ and (+)-gomisin $M_2$. Chemical and Pharmaceutical Bulletin. 30:132-139. https://doi.org/10.1248/cpb.30.132
  15. Ikeya Y, Ookawa N, Taguchi H and Yosioka I. (1982b). The constituents of Schizandra chinensis Baill. XI. The structures of three new lignans, angeloylgomisin O, and angeloyl- and benzoylisogomisin O. Chemical and Pharmaceutical Bulletin. 30:3202-3206. https://doi.org/10.1248/cpb.30.3202
  16. Ikeya Y, Taguchi H and Yosioka I. (1982c). The constituents of Schizandra chinensis Baill. XII. Isolation and structures of new lignans, gomisin R, the absolute structures of wuweizisu C and isolation of schisantherin D. Chemical and Pharmaceutical Bulletin. 30:3207-3211. https://doi.org/10.1248/cpb.30.3207
  17. Ikeya Y, Kanatani H, Hakozaki M, Taguchi H and Mitsuhashi H. (1988a). The constituents of Schizandra chinensis Baill. XV. Isolation and structure determination of two new lignans, gomisin S and gomisin T. Chemical and Pharmaceutical Bulletin. 36:3974-3979. https://doi.org/10.1248/cpb.36.3974
  18. Ikeya Y, Taguchi H, Mitsuhashi H, Takeda S, Kase Y and Aburada M. (1988b). A lignan from Schizandra chinensis. Phytochemistry. 27:569-573. https://doi.org/10.1016/0031-9422(88)83143-1
  19. Ikeya Y, Miki E, Okada M, Mitsuhashi H and Chai JG. (1990). Benzoylgomisin Q and benzoylgomisin P, two new lignans from Schisandra sphenanthera Rehd. et Wils. Chemical and Pharmaceutical Bulletin. 38:1408-1411. https://doi.org/10.1248/cpb.38.1408
  20. Ikeya Y, Sugama K, Okada M and Mitsuhashi H. (1991). Two lignans from Schisandra sphenanthera. Phytochemistry. 30:975-980. https://doi.org/10.1016/0031-9422(91)85290-G
  21. Kang MG, Kim YH, Im AR, Nam BS, Chae SW and Lee MY. (2014). Antidepressant-like effects of Schisandra chinensis Baillon water extract on animal model induced by chronic mild stress. Korean Journal of Medicinal Crop Science. 22:196-202. https://doi.org/10.7783/KJMCS.2014.22.3.196
  22. Kim MG, Lee CH and Lee HS. (2010). Anti-platelet aggregation activity of lignans isolated from Schisandra chinensis fruits. Journal of the Korean Society for Applied Biological Chemistry. 53:740-745. https://doi.org/10.3839/jksabc.2010.112
  23. Kwon DY, Kim DS, Yang HJ and Park SM. (2011). The lignanrich fractions of Fructus Schisandrae improve insulin sensitivity via the PPAR-γ pathways in in vitro and in vivo studies. Journal of Ethnopharmacology. 135:455-462. https://doi.org/10.1016/j.jep.2011.03.037
  24. Lee JH, Beak IY, Ko JM, Shim KB, Kang NS, Kim HT, Kang CH, Park KY, Park KH and Ha TJ. (2008). Correlation of lignan contents with protein and oil contents in the seeds of Sesamum indicum L. Journal of Applied Biological Chemistry. 51:20-27. https://doi.org/10.3839/jabc.2008.005
  25. Lu Y and Chen DF. (2009). Analysis of Schisandra chinensis and Schisandra sphenanthera. Journal of Chromatography A. 1216:1980-1990. https://doi.org/10.1016/j.chroma.2008.09.070
  26. Oh SY, Kim YH, Bae DS, Um BH, Pan CH, Kim CY, Lee HJ and Lee JK. (2010). Anti-inflammatory effects of gomisin N, gomisin J, schisandrin C isolated from the fruit of Schisandra chinensis. Bioscience, Biotechnology, and Biochemistry. 74:285-291. https://doi.org/10.1271/bbb.90597
  27. Rangkadilok N, Pholphana N, Mahidol C, Wongyai W, Saengsooksree K, Nookabkaew S and Satayavivad J. (2010). Variation of sesamin, sesamolin and tocopherols in sesame (Sesamum indicum L.) seeds and oil products in Thailand. Food Chemistry. 122:724-730. https://doi.org/10.1016/j.foodchem.2010.03.044
  28. Taguchi H and Ikeya Y. (1977). The constituents of Schizandra chinensis Baill. The structures of two new lignans, gomisin F and G, and the absolute structures of gomisin A, B, and C. Chemical and Pharmaceutical Bulletin. 25:364-366. https://doi.org/10.1248/cpb.25.364
  29. Wang BL, Hu JP, Tan W, Sheng L, Chen H and Li Y. (2008). Simultaneous quantification of four active schisandra lignans from a traditional Chinese medicine Schisandra chinensis (Wuweizi) in rat plasma using liquid chromatography/mass spectrometry. Journal of Chromatography B. 865:114-120. https://doi.org/10.1016/j.jchromb.2008.02.016
  30. Wang YH, Qiu C, Wang DW, Hu ZF, Yu BY and Zhu DN. (2011). Identification of multiple constituents in the traditional Chinese medicine formula Sheng-Mai San and rat plasma after oral administration by HPLC-DAD-MS/MS. Journal of Pharmaceutical and Biomedical Analysis. 54:1110-1127. https://doi.org/10.1016/j.jpba.2010.11.034
  31. Wei H, Sun L, Tai Z, Gao S, Xu W and Chen W. (2010). A simple and sensitive HPLC method for the simultaneous determination of eight bioactive components and fingerprint analysis of Schisandra sphenanthera. Analytica Chimica Acta. 662:97-104. https://doi.org/10.1016/j.aca.2009.12.039
  32. Yang JM, Ip PSP, Yeung JHK and Che CT. (2011). HPLC-MS analysis of Schisandra lignans and their metabolites in Caco-2 cell monolayer and rat everted gut sac models and in rat plasma. Acta Pharmaceutica Sinica B. 1:46-55. https://doi.org/10.1016/j.apsb.2011.04.007
  33. Yuan G, Liu Y, Li T, Wang Y, Sheng Y and Guan M. (2011). Simultaneous and rapid determination of main lignans in different parts of Schisandra sphenanthera by micellar electrokinetic capillary chromatography. Molecules. 16:3713-3722. https://doi.org/10.3390/molecules16053713
  34. Zhu M, Chen XS and Wang KX. (2007). Variation of the lignan content of Schisandra chinensis(Turcz.) Baill. and Schisandra sphenanthera Rehd. et Wils. Chromatographia. 66:125-128. https://doi.org/10.1365/s10337-007-0261-3

Cited by

  1. Chemical Components Composition on Different Parts of Fruit in Schisandra chinensis Baillon vol.45, pp.6, 2016, https://doi.org/10.3746/jkfn.2016.45.6.851