華中五味子種子活性木質酚素成分之研究

黃馨嬋

doi:10.6342/NTU.2010.03522

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華中五味子種子活性木質酚素成分之研究

Bioactive Lignans from the Seeds of Schisandra sphenanthera

黃馨嬋 , Masters　　Advisor：沈雅敬　　

繁體中文 DOI： 10.6342/NTU.2010.03522

華中五味子；種子；木質酚素； aryltetralone ； dibenzocyclooctadiene ； Schisandra sphenanthera ； seeds ； ignan ； aryltetralone ； dibenzocyclooctadiene

Abstract │ Reference (92) │ Altmetrics

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This research investigated the chemical constituents of the seeds from the medicinal plant Schisandra sphenanthera. From the ethanol extract, seven new oxygenated lignans (1-7), and eleven known compounds (8-18) were isolated. New components could be classified into 6,7-seco dibenzocyclooctadiene type lignan, schisphenin B (1), aryltetralone type lignan, schisphentetralone A (2), and C18-dibenzocyclooctadiene lignans, schisphenins C-G (3-7).  The known compounds were identified as nine lignans： pre-gomisin (8), meso-dihydroguaiaretic acid (9), veraguensin (10), (－)-8epi-aristoligone (11), benzoylgomisin P (12), benzoylgomisin U (13), gomisin F (14), (＋)-gomisin K3 (15), and schisantherin D (16), together with two triterpenoids, kadsuric acid (17) and coccinic acid (18).

The structural elucidations of these compounds were determined on the basis of spectroscopic analyses of 1D-NMR (1H and 13C-NMR), 2D-NMR (COSY, HMQC, HMBC, NOESY) techniques, physical methods including optical rotation, IR, UV, CD, HRESIMS, as well as by comparison of the published data. The CD results showed that the biphenyl groups of new compounds 3-7 were all S-configuration and the analyses of NOESY correlations revealed that the octadiene moieties of them were twist-boat-chair conformation.

Biological activities of all isolated components were evaluated as well. The reporter gene assay was used to measure anti-liver fibrosis effect in this study. Compounds 1, 2, 4, 11, 13, 14, 18 were regarded as better anti-inflammatory activity substances on HSC-T6 test. Among them, 11 is the most potential one because its activity is better than the positive control, silymarin. The DPPH free-radical scavenging experiment indicated that compound 9 exhibited good effect at 0.006 M (scarvenging activity 55.4%), but it was worse than vitamin C at 0.0057 M (scarvenging activity 95.8%).

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3. Chiu, P. Y.; Leung, H. Y.; Ko, K. M. Schisandrin B enhances renal mitochondrial antioxidant status, functional and structural integrity, and protects against gentamicin-induced nephrotoxicity in rats. Biological & Pharmaceutical Bulletin 2008, 31, 602-605.
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7. Panossian, A.; Wikman, G. Pharmacology of Schisandra chinensis Baill: an overview of Russian research and uses in medicine. Journal of Ethnopharmacology 2008, 118, 183-212.
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8. Kochetkov, N. K.; Khorlin, A. Y.; Chizhov, O. S. Deoxyschizandrin. Structure and total synthesis. Tetrahedron Letters 1962, 361–363.
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10. Ikeya, Y.; Taguchi, H.; Yosioka, I. The constituents of Schizandra chinensis Baill. Isolation and structure of a new lignan, gomisin R, the absolute structure of
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