한국산 오미자로부터 디벤조사이클로옥타디엔 계열 리그난 화합물 정성 및 정량 분석
Qualitative and Quantitative Analysis of Dibenzocyclooctadiene Lignans for the Fruits of Korean “Omija” (Schisandra chinensis)
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초록
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 lignanrich 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, γ- 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 1350.1㎎ per 100 g dry weight, respectively. The total lignan content averaged 2011.4㎎ per 100 g dry weight, of which schisandrin and gomisin N comprised the majority (771.8 and 420.5㎎ 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.
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 lignanrich 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, γ- 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 1350.1㎎ per 100 g dry weight, respectively. The total lignan content averaged 2011.4㎎ per 100 g dry weight, of which schisandrin and gomisin N comprised the majority (771.8 and 420.5㎎ 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.
참고문헌 (34)
- Chang GT, "Inhibitory effect of the Korean herbal medicine, Dae-Jo-Whan, on platelet activating factor induced platelet aggregation", Journal of Ethnopharmacology, 102, pp.430~439 (2005)
- Deng X, "Simultaneous LC-MS quantification of 15 lignans in Schisandra chinensis(Turcz. )Baill fruit", Chromatographia, 67, pp.559~566 (2008)
- Gu BH, "Deoxyschisandrin inhibits H2O2 induced apoptotic cell death in intestinal epithelial cells through nuclear factor KB", International Journal of Molecular Medicine, 26, pp.401~406 (2010)
- Guo LY, "Anti-inflammatory effects of schisandrin isolated from the fruit of Schisandra chinensis Baill", European Journal of Pharmacology, 591, pp.293~299 (2008)
- He XG, "Analysis of lignan constituents from Schisandra chinensis by liquid chromatographyelectrospray mass spectrometry", Journal of Chromatography A, 757, pp.81~87 (1997)
- Huang T, "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, pp.239~242 (2005)
- Huang TL, "Purification of lignans from Schisandra chinensis fruit by using column fractionation and supercritical antisolvent precipitation", Journal of Chromatography A, 1282, pp.27~37 (2013)
- Ikeya Y, "The constituents of Schizandra chinensis Baill. The structures of two new lignans, pre-gomisin and gomisin", Journal of Chemical and Pharmaceutical Bulletin, 26, pp.682~684 (1978)
- Ikeya Y, "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, pp.1576~1582 (1979)
- Ikeya Y, "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, pp.2695~2709 (1979)
- Ikeya Y, "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, pp.2536~2538 (1979)
- Ikeya Y, "The constituents of Schizandra chinensis Baill. Ⅶ. The structures of three new lignans, (−)-gomisin K1 and (+)-gomisins K2 and K3", Chemical and Pharmaceutical Bulletin, 28, pp.2422~2427 (1980)
- Ikeya Y, "The constituents of Schizandra chinensis Baill. VIII. The structures of two new lignans, tigloylgomisin P and angeloylgomisin P", Chemical and Pharmaceutical Bulletin, 28, pp.3357~3361 (1980)
- Ikeya Y, "The constituents of Schizandra chinensis Baill. VII. The structures of γ-schizandrin and four new lignans, (−)-gomisin L1 and L2, (±)-gomisins M1 and (+)-gomisin M2", Chemical and Pharmaceutical Bulletin, 30, pp.132~139 (1982)
- Ikeya Y, "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, pp.3202~3206 (1982)
- Ikeya Y, "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, pp.3207~3211 (1982)
- Ikeya Y, "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, pp.3974~3979 (1988)
- Ikeya Y, "A lignan from Schizandra chinensis", Phytochemistry, 27, pp.569~573 (1988)
- Ikeya Y, "Benzoylgomisin Q and benzoylgomisin P, two new lignans from Schisandra sphenanthera Rehd. et Wils", Chemical and Pharmaceutical Bulletin, 38, pp.1408~1411 (1990)
- Ikeya Y, "Two lignans from Schisandra sphenanthera", Phytochemistry, 30, pp.975~980 (1991)
- 강민구, "만성스트레스로 유발된 우울증 동물모델에서 오미자 물 추출물의 항우울 효과", 한국약용작물학회지, 22(3), pp.196~202 (2014), 한국약용작물학회[DOI]
- 김민기, "Anti-platelet Aggregation Activity of Lignans Isolated from Schisandra chinensis Fruits", Applied Biological Chemistry, 53(6), pp.740~745 (2010), 한국응용생명화학회
- Kwon DY, "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, pp.455~462 (2011)
- 이진환, "Correlation of Lignan Contents with Protein and Oil Contentsin the Seeds of Sesamum indicum L.", Journal of Applied Biological Chemistry, 51(1), pp.20~27 (2008), 한국응용생명화학회
- Lu Y, "Analysis of Schisandra chinensis and Schisandra sphenanthera", Journal of Chromatography A, 1216, pp.1980~1990 (2009)
- Oh SY, "Anti-inflammatory effects of gomisin N, gomisin J, schisandrin C isolated from the fruit of Schisandra chinensis", Bioscience, Biotechnology, and Biochemistry, 74, pp.285~291 (2010)
- Rangkadilok N, "Variation of sesamin, sesamolin and tocopherols in sesame(Sesamum indicum L. )seeds and oil products in Thailand", Food Chemistry, 122, pp.724~730 (2010)
- Taguchi H, "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, pp.364~366 (1977)
- Wang BL, "Simultaneous quantification of four active schisandra lignans from a traditional Chinese medicine Schisandra chinensis(Wuweizi)in rat plasma using liquid chromatography", mass spectrometry, 2008, pp.865, 114~120
- Wang YH, "Identification of multiple constituents in the traditional Chinese medicine formula Sheng-Mai San and rat plasma after oral administration by HPLC-DAD-MS", MS, 2011, pp.54, 1110~1127
- Wei H, "A simple and sensitive HPLC method for the simultaneous determination of eight bioactive components and fingerprint analysis of Schisandra sphenanthera", Analytica Chimica Acta, 662, pp.97~104 (2010)
- Yang JM, "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, pp.46~55 (2011)
- Yuan G, "Simultaneous and rapid determination of main lignans in different parts of Schisandra sphenanthera by micellar electrokinetic capillary chromatography", Molecules, 16, pp.3713~3722 (2011)
- Zhu M, "Variation of the lignan content of Schisandra chinensis(Turcz. )Baill. and Schisandra sphenanthera Rehd. et Wils", Chromatographia, 66, pp.125~128 (2007)