臺灣博碩士論文加值系統

五味子是一種常見的傳統中藥材，而由初步活性測試顯示五味子具有良好的調解血糖之活性。將五味子分離萃取後，共得到35個化合物，其中29個化合物經1H-NMR、UV、IR與文獻比對確認，分別為macelignan (76)、schisandrin A (78)、gomisin K3 (80)、gomisin J (81)、schisandrin B (83)、gomisin N (84)、gomisin M2 (85)、gomisin L2 (86)、(-)-gomisin L1 (87)、(S)-angeloylgomisin M1 (90)、(R)-angeloylgomisin M1 (90)、schisandrin C (91)、schisandrin (93)、angeloylgomisin H (94)、tigloylgomisin H (95)、gomisin A (100)、schisandrinen A (101)、gomisin R (113)、gomisin F(126)、gomisin G (128)、gomisin P(130)、tiglogomisin P (132)、gomisin B (135)、schisanchinin A (142)、gomisin D (153)、trimethyl citrate (164)、β-sitosterol (165)、1,1'-(4'',4''',5'',5''',6'',6'''-hexamethoxybiphenyl-2'',2'''-diyl)bis(propan-2-one) (166)、5-hydroxymethylfuran-2-carboxaldehyde (167)。其中，trimethyl citrate (164)為首次由本植物分離得到；1,1'-(4'',4''',5'',5''',6'',6'''-hexamethoxybiphenyl-2'',2'''-diyl)bis(propan-2-one) (166) 為首次由天然來源分離得到的化合物。另外6個化合物SC-A、SC-B、SC-C、SC-D、SC-E與SC-F，經由各類光譜及CD光譜確認為新化合物。
針對化合物的活性試驗結果顯示，在1.0mg/mL的濃度下，有32個化合物對抑制α-glucosidase活性顯示不錯抑制活性；另外，在1.0mg/mL的濃度下，有24個化合物於IC50試驗中表現出良好的活性。
由本研究顯示，五味子低極性成分中所含的木脂素類化合物對於抑制α-glucosidase有很好的活性，在未來對於糖尿病的治療方面是很有潛力的研究題材。

The dried fruits of Schisandra chinensis is a common traditional Chinese medicine. Based on the research, the extracts of Schisandra chinensis showed good antidiabetic activity. Thirty-five compounds were obtained and comfirmed by 1H-NMR, UV, and IR：
macelignan (76)、schisandrin A (78)、gomisin K3 (80)、gomisin J (81)、schisandrin B (83)、gomisin N (84)、gomisin M2 (85)、gomisin L2 (86)、(-)-gomisin L1 (87)、(S)-angeloylgomisin M1 (90)、(R)-angeloylgomisin M1 (90)、schisandrin C (91)、schisandrin (93)、angeloylgomisin H (94)、tigloylgomisin H (95)、gomisin A (100)、schisandrinen A (101)、gomisin R (113)、gomisin F(126)、gomisin G (128)、gomisin P(130)、tiglogomisin P (132)、gomisin B (135)、schisanchinin A (142)、gomisin D (153)、trimethyl citrate (164)、β-sitosterol (165)、1,1'-(4'',4''',5'',5''',6'',6'''-hexamethoxybiphenyl-2'',2'''-diyl)bis(propan-2-one) (166)、5-hydroxymethylfuran-2-carboxaldehyde (167), and SC-A~F .
Among them, the compound trimethyl citrate (164) was first isolated from this plant, and 1,1'-(4'',4''',5'',5''',6'',6'''-hexamethoxybiphenyl-2'',2'''-diyl)bis(propan-2-one) (166) was isolated from the natural sources for the first time. In addition, SC-A, SC-B, SC-C, SC-E and SC-F were identified as new structures according to their various spectrum.
The result of the activity test demonstrated that thirty-two compounds have good activities in the concentration of 1.0mg/mL on inhibiting α-glucosidase. In addition, twenty-four compounds have excellent activities in the concentration of 1.0mg/mL on IC50 test. This research shows that the lignins in low polarity fraction of Schisandra chinensis has significant activities on inhibiting α-glucosidase. Therefore, it is a potential research material on diabete treatment in the future.

誌 謝 I
中 文 摘 要 II
英 文 摘 要 III
目 錄 IV
第一章 緒論 1
第一節 植物型態 1
第二節 研究背景與目的 2
第二章 文獻探討 7
第一節 五味子植物之藥理與藥效 7
第二節 五味子植物之成分回顧 13
第三章 材料與方法 31
第一節 儀器與材料 31
第二節 活性測試 33
3.2.1 抑制α-glucosidase活性 33
3.2.2 清除DPPH自由基活性測試 34
3.2.3 清除過氧化氫能力之測定 35
3.2.4 抑制氫過氧化物產生之測定 36
3.2.5 共軛雙烯之測定 37
3.2.6 微脂粒氧化作用之抑制 38
第四章 五味子之萃取與分離 39
第五章 五味子化合物之構造研究 43
第一節 Macelignan (76)構造研究 49
第二節 Schisandrin B (83)構造研究 51
第三節 Schisandrin (93)構造研究 53
第四節 Gomisin G (128)構造研究 55
第五節 Schisanchinin A (142)構造研究 58
第六節 Gomisin D (153)構造研究 61
第七節 1,1'-(4'',4''',5'',5''',6'',6'''-Hexamethoxybiphenyl-2'',2'''-diyl)bis (propan-2-one) (166)構造研究 63
第八節 SC-A構造研究 65
第九節 SC-B構造研究 67
第十節 SC-C構造研究 71
第十一節 SC-D構造研究 75
第十二節 SC-E構造研究 78
第十三節 SC-F構造研究 80
第十四節 Trimethyl citrate (164)構造研究 82
第六章 五味子化合物之活性測試研究 84
第七章 結論 92
參考文獻 93
附錄 光譜數據 100
附錄 植物的萃取與分離 116

[1]張俊榮, 符紅, 藥材選購須知: 旺文社股份有限公司, 1997.
[2]中國醫藥管理局, 中華本草: 上海科學技術出版社, 2000.
[3]林興中, "糖尿病病因", 財團法人糖尿病關懷基金會, 2006.
取自網址http://www.dmcare.org.tw/up3/2006-4-%E6%9E%97%E8%88%88%E4%B8%AD.pdf (網路期刊，擷取日期04, 2015)
[4]李建南, "妊娠與糖尿病", 衛教學會會訊, p. 1, 2008.
取自網址https://www.tade.org.tw/upload/people/28.pdf (網路期刊，擷取日期04, 2015)
[5]劉紹毅, "自由基簡介",中華民國血液淨化醫學會雜誌, 財團法人台灣血液淨化基金會, 2005.
取自網址 http://www.fbpf.org.tw/front/bin/ptdetail.phtml?Part=cc0041&Category=129510 (網路期刊，擷取日期04, 2015)
[6]吳崇榮, "糖尿病慢性併發症的致病機轉和未來展望", 台灣醫界, vol. 47, 2004.
取自網址http://www.tma.tw/magazine/ShowRepID.asp?rep_id=1678 (網路期刊，擷取日期04, 2015)
[7]王月婷, 王秋平, "糖尿病的神經血管疾病、抗氧化劑與醣化作用", 台南市立醫院社區健康促進委員會, 2003.
取自網址http://cn.24drs.com/gate/gb/www.tmh.org.tw/communityimprove/show_h.php?id=806
[8]康景軒, "自由基與糖尿病,"吃出健康的智慧:來自哈佛醫學院的健康新理念: 化學工業出版社, p. 27, 2009.
[9]李時珍原著, 紫圖編繪, 圖解本草綱目: 陝西師範大學出版社, 2009.
[10]S. H. Jo, K. S. Ha, K. S. Moon, O. H. Lee, H. D. Jang, and Y. I. Kwon, "In vitro and in vivo anti-hyperglycemic effects of Omija (Schizandra chinensis) fruit," Int J Mol Sci, vol. 12, pp. 1359-1370, 2011.
[11]H. Bae, R. Kim, Y. Kim, E. Lee, H. J. Kim, and Y. P. Jang, et al., "Effects of Schisandra chinensis Baillon (Schizandraceae) on lipopolysaccharide induced lung inflammation in mice," J Ethnopharmacol, vol. 142, pp. 41-47, 2012.
[12]Y. J. Lee, J. Y. Cho, J. H. Kim, W. K. Park, D. K. Kim, and M. R. Rhyu, "Extracts from Schizandra chinensis fruit activate estrogen receptors: a possible clue to its effects on nitric oxide-mediated vasorelaxation," Biol Pharm Bull, vol. 27, pp. 1066-1069, 2004.
[13]J. S. You, T. L. Pan, and Y. C. Hou, "Schisandra chinensis protects against adriamycin-induced cardiotoxicity in rats," Chang Gung Med J, vol. 29, pp. 63-70, 2006.
[14]M. R. Rhyu, E. Y. Kim, B. K. Yoon, Y. J. Lee, and S. N. Chen, "Aqueous extract of Schizandra chinensis fruit causes endothelium-dependent and -independent relaxation of isolated rat thoracic aorta," Phytomedicine, vol. 13, pp. 651-657, 2006.
[15]E. H. Choi, N. Lee, H. J. Kim, M. K. Kim, S. G. Chi, and D. Y. Kwon, et al., "Schisandra fructus extract ameliorates doxorubicin-induce cytotoxicity in cardiomyocytes: altered gene expression for detoxification enzymes," Genes Nutr, vol. 2, pp. 337-345, 2008.
[16]J. Y. Park, H. K. Shin, Y. J. Lee, Y. W. Choi, S. S. Bae, and C. D. Kim, "The mechanism of vasorelaxation induced by Schisandra chinensis extract in rat thoracic aorta," J Ethnopharmacol, vol. 121, pp. 69-73, 2009.
[17]E. Y. Kim, I. H. Baek, and M. R. Rhyu, "Cardioprotective effects of aqueous Schizandra chinensis fruit extract on ovariectomized and balloon-induced carotid artery injury rat models: effects on serum lipid profiles and blood pressure," J Ethnopharmacol, vol. 134, pp. 668-675, 2011.
[18]J. Y. Park, Y. W. Choi, J. W. Yun, J. U. Bae, K. W. Seo, and S. J. Lee, et al., "Gomisin J from Schisandra chinensis induces vascular relaxation via activation of endothelial nitric oxide synthase," Vascul Pharmacol, vol. 57, pp. 124-130, 2012.
[19]J. Y. Park, J. W. Yun, Y. W. Choi, J. U. Bae, K. W. Seo, and S. J. Lee, et al., "Antihypertensive effect of gomisin A from Schisandra chinensis on angiotensin II-induced hypertension via preservation of nitric oxide bioavailability," Hypertens Res, vol. 35, pp. 928-934, 2012.
[20]J. M. Yang, P. S. Ip, C. T. Che, and J. H. Yeung, "Relaxant effects of Schisandra chinensis and its major lignans on agonists-induced contraction in guinea pig ileum," Phytomedicine, vol. 18, pp. 1153-1160, 2011.
[21]J. M. Yang, Y. F. Xian, P. S. Ip, J. C. Wu, L. Lao, and H. H. Fong, et al., "Schisandra chinensis reverses visceral hypersensitivity in a neonatal-maternal separated rat model," Phytomedicine, vol. 19, pp. 402-408, 2012.
[22]M. Zhu, K. F. Lin, R. Y. Yeung, and R. C. Li, "Evaluation of the protective effects of Schisandra chinensis on Phase I drug metabolism using a CCl4 intoxication model," J Ethnopharmacol, vol. 67, pp. 61-68, 1999.
[23]K. J. Kim, K. Y. Yoon, H. D. Hong, and B. Y. Lee, "Schisandra chinensis prevents hepatic lipid peroxidation and oxidative stress in rats subjected to heat environmental stress," Phytother Res, vol. 26, pp. 1674-1680, 2012.
[24]N. Cheng, N. Ren, H. Gao, X. Lei, J. Zheng, and W. Cao, "Antioxidant and hepatoprotective effects of Schisandra chinensis pollen extract on CCl4-induced acute liver damage in mice," Food Chem Toxicol, vol. 55, pp. 234-240, 2013.
[25]Y. Takimoto, H. Y. Qian, E. Yoshigai, T. Okumura, Y. Ikeya, and M. Nishizawa, "Gomisin N in the herbal drug gomishi (Schisandra chinensis) suppresses inducible nitric oxide synthase gene via C/EBPbeta and NF-kappaB in rat hepatocytes," Nitric Oxide, vol. 28, pp. 47-56, 2013.
[26]李斌, 孟憲軍, 薛雪, 吳倩, 李元甦, 汪豔群, "北五味子乙素清除自由基及體外抑菌作用的研究," 食品科學, vol. 32, pp. 79-82, 2011.
[27]S. H. Kim, M. H. Joo, and S. H. Yoo, "Structural identification and antioxidant properties of major anthocyanin extracted from Omija (Schizandra chinensis) fruit," J Food Sci, vol. 74, pp. C134-140, 2009.
[28]X. Chen, Y. Zhang, Y. Zu, and L. Yang, "Chemical composition and antioxidant activity of the essential oil of Schisandra chinensis fruits," Nat Prod Res, vol. 26, pp. 842-849, 2012.
[29]C. J. Liu, S. Q. Zhang, J. S. Zhang, Q. Liang, and D. S. Li, "Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis (Turcz.) Baill," Nat Prod Res, vol. 26, pp. 2199-2203, 2012.
[30]M. Zhang, M. Liu, M. Xiong, J. Gong, and X. Tan, "Schisandra chinensis fruit extract attenuates albuminuria and protects podocyte integrity in a mouse model of streptozotocin-induced diabetic nephropathy," J Ethnopharmacol, vol. 141, pp. 111-118, 2012.
[31]Y. J. Lee, J. W. Shim, Y. J. Lee, Y. H. Park, H. Y. Lee, and S. D. Kim, et al., "Identification of a novel compound that stimulates intracellular calcium increase and CXCL8 production in human neutrophils from Schisandra chinensis," Biochem Biophys Res Commun, vol. 379, pp. 928-932, 2009.
[32]R. D. Lin, Y. W. Mao, S. J. Leu, C. Y. Huang, and M. H. Lee, "The immuno-regulatory effects of Schisandra chinensis and its constituents on human monocytic leukemia cells," Molecules, vol. 16, pp. 4836-4849, 2011.
[33]Y. Chen, J. Tang, X. Wang, F. Sun, and S. Liang, "An immunostimulatory polysaccharide (SCP-IIa) from the fruit of Schisandra chinensis (Turcz.) Baill," Int J Biol Macromol, vol. 50, pp. 844-848, 2012.
[34]Y. H. Kang and H. M. Shin, "Inhibitory effects of Schizandra chinensis extract on atopic dermatitis in NC/Nga mice," Immunopharmacol Immunotoxicol, vol. 34, pp. 292-298, 2012.
[35]S. K. Lee, S. D. Kim, H. Y. Lee, S. H. Baek, M. J. Ko, and B. G. Son, et al., "alpha-Iso-cubebene, a natural compound isolated from Schisandra chinensis fruit, has therapeutic benefit against polymicrobial sepsis," Biochem Biophys Res Commun, vol. 426, pp. 226-231, 2012.
[36]S. K. Lee, S. D. Kim, M. Kook, H. Y. Lee, J. S. Park, and Y. H. Park, et al., "Therapeutic effects of alpha-iso-cubebenol, a natural compound isolated from the Schisandra chinensis fruit, against sepsis," Biochem Biophys Res Commun, vol. 427, pp. 547-552, 2012.
[37]Y. S. Jung, S. K. Lee, C. Y. Ok, E. J. Cho, J. S. Park, and Y. W. Choi, et al., "Role of CXCR2 on the immune modulating activity of alpha-iso-cubebenol a natural compound isolated from the Schisandra chinensis fruit," Biochem Biophys Res Commun, vol. 431, pp. 433-436, 2013.
[38]L. Y. Guo, T. M. Hung, K. H. Bae, E. M. Shin, H. Y. Zhou, and Y. N. Hong, et al., "Anti-inflammatory effects of schisandrin isolated from the fruit of Schisandra chinensis Baill," Eur J Pharmacol, vol. 591, pp. 293-299, 2008.
[39]Y. J. Lee, S. Y. Park, S. G. Kim, J. Park da, J. S. Kang, and S. J. Lee, et al., "Identification of a novel compound that inhibits iNOS and COX-2 expression in LPS-stimulated macrophages from Schisandra chinensis," Biochem Biophys Res Commun, vol. 391, pp. 1687-1692, 2010.
[40]S. Y. Oh, Y. H. Kim, D. S. Bae, B. H. Um, C. H. Pan, and C. Y. Kim, et al., "Anti-inflammatory effects of gomisin N, gomisin J, and schisandrin C isolated from the fruit of Schisandra chinensis," Biosci Biotechnol Biochem, vol. 74, pp. 285-291, 2010.
[41]S. Y. Park, J. Park da, Y. H. Kim, Y. Kim, Y. W. Choi, and S. J. Lee, "Schisandra chinensis alpha-iso-cubebenol induces heme oxygenase-1 expression through PI3K/Akt and Nrf2 signaling and has anti-inflammatory activity in Porphyromonas gingivalis lipopolysaccharide-stimulated macrophages," Int Immunopharmacol, vol. 11, pp. 1907-1915, 2011.
[42]M. G. Dilshara, R. G. Jayasooriya, C. H. Kang, S. Lee, S. R. Park, and J. W. Jeong, et al., "Downregulation of pro-inflammatory mediators by a water extract of Schisandra chinensis (Turcz.) Baill fruit in lipopolysaccharide-stimulated RAW 264.7 macrophage cells," Environ Toxicol Pharmacol, vol. 36, pp. 256-264, 2013.
[43]H. Y. Min, E. J. Park, J. Y. Hong, Y. J. Kang, S. J. Kim, and H. J. Chung, et al., "Antiproliferative effects of dibenzocyclooctadiene lignans isolated from Schisandra chinensis in human cancer cells," Bioorg Med Chem Lett, vol. 18, pp. 523-526, 2008.
[44]D. Hwang, S. Y. Shin, Y. Lee, J. Hyun, Y. Yong, and J. C. Park, et al., "A compound isolated from Schisandra chinensis induces apoptosis," Bioorg Med Chem Lett, vol. 21, pp. 6054-6057, 2011.
[45]T. Zhao, G. Mao, R. Mao, Y. Zou, D. Zheng, and W. Feng, et al., "Antitumor and immunomodulatory activity of a water-soluble low molecular weight polysaccharide from Schisandra chinensis (Turcz.) Baill," Food Chem Toxicol, vol. 55, pp. 609-616, 2013.
[46]S. R. Kim, M. K. Lee, K. A. Koo, S. H. Kim, S. H. Sung, and N. G. Lee, et al., "Dibenzocyclooctadiene lignans from Schisandra chinensis protect primary cultures of rat cortical cells from glutamate-induced toxicity," J Neurosci Res, vol. 76, pp. 397-405, 2004.
[47]T. M. Hung, M. Na, B. S. Min, T. M. Ngoc, I. Lee, and X. Zhang, et al., "Acetylcholinesterase inhibitory effect of lignans isolated from Schizandra chinensis," Arch Pharm Res, vol. 30, pp. 685-690, 2007.
[48]J. P. Wang, S. L. Raung, M. F. Hsu, and C. C. Chen, "Inhibition by gomisin C (a lignan from Schizandra chinensis) of the respiratory burst of rat neutrophils," Br J Pharmacol, vol. 113, pp. 945-953, 1994.
[49]Y. W. Choi, K. Kim, J. Y. Jo, H. L. Kim, Y. J. Lee, W. J. Shin, et al., "Wuweizisu C from Schisandra chinensis decreases membrane potential in C6 glioma cells," Acta Pharmacol Sin, vol. 29, pp. 1006-1012, 2008.
[50]W. Caichompoo, Q. Y. Zhang, T. T. Hou, H. J. Gao, L. P. Qin, and X. J. Zhou, "Optimization of extraction and purification of active fractions from Schisandra chinensis (Turcz.) and its osteoblastic proliferation stimulating activity," Phytother Res, vol. 23, pp. 289-292, 2009.
[51]E. Y. Oh, J. Y. Jang, Y. H. Choi, Y. W. Choi, and B. T. Choi, "Inhibitory effects of 1-O-methyl-fructofuranose from Schisandra chinensis fruit on melanogenesis in B16F0 melanoma cells," J Ethnopharmacol, vol. 132, pp. 219-224, 2010.
[52]V. V. Giridharan, R. A. Thandavarayan, S. Sato, K. M. Ko, and T. Konishi, "Prevention of scopolamine-induced memory deficits by schisandrin B, an antioxidant lignan from Schisandra chinensis in mice," Free Radic Res, vol. 45, pp. 950-958, 2011.
[53]D. Hu, Y. Cao, R. He, N. Han, Z. Liu, and L. Miao, et al., "Schizandrin, an antioxidant lignan from Schisandra chinensis, ameliorates Aβ1-42-induced memory impairment in mice," Oxid Med Cell Longev, doi:10.1155/2012/721721, vol. 2012, 2012.
[54]B. Wei, Q. Li, R. Fan, D. Su, X. Ou, and K. Chen, et al., "UFLC-MS/MS method for simultaneous determination of six lignans of Schisandra chinensis (Turcz.) Baill. in normal and insomniac rats brain microdialysates and homogenate samples: towards an in-depth study for its sedative-hypnotic activity," J Mass Spectrom, vol. 48, pp. 448-458, 2013.
[55]O. Yoshimoto, and H. Yoshio, "New sesquiterpenoids from Schisandra chinensis," Tetrahedron Letters, vol. 9, pp. 2483-2485, 1968.
[56]O. Yoshimoto, and H. Yoshio, "Structure of sesquicarene," Tetrahedron Letters, vol. 9, pp. 1251-1254, 1968.
[57]S. X. Huang, Q. B. Han, C. Lei, J. X. Pu, W. L. Xiao, and J. L. Yu, et al., "Isolation and characterization of miscellaneous terpenoids of Schisandra chinensis," Tetrahedron, vol. 64, pp. 4260-4267, 2008.
[58]R. A. Flath, R. T. Cunningham, T. R. Mon, and J. O. John, "Male lures for mediterranean fruitfly (Ceratitis capitata wied.): Structural analogs of alpha-copaene," J Chem Ecol, vol. 20, pp. 2595-2609, 1994.
[59]J. R. Wang, Z. B. Zhao, and Y. W. Guo, "A new highly oxygenated nortriterpenoid from Schisandra chinensis," J Asian Nat Prod Res, vol. 13, pp. 551-555, 2011.
[60]Q. Y. Song, K. Jiang, Q. Q. Zhao, K. Gao, X. J. Jin, and X. J. Yao, "Eleven new highly oxygenated triterpenoids from the leaves and stems of Schisandra chinensis," Org Biomol Chem, vol. 11, pp. 1251-1258, 2013.
[61]S. X. Huang, R. T. Li, J. P. Liu, Y. Lu, Y. Chang, and C. Lei, et al., "Isolation and characterization of biogenetically related highly oxygenated nortriterpenoids from Schisandra chinensis," Org Lett, vol. 9, pp. 2079-2082, 2007.
[62]Y. B. Xue, Y. L. Zhang, J. H. Yang, X. Du, J. X. Pu, and W. Zhao, et al., "Nortriterpenoids and lignans from the fruit of Schisandra chinensis," Chem Pharm Bull, vol. 58, pp. 1606-1611, 2010.
[63]S. X. Huang, L. B. Yang, W. L. Xiao, C. Lei, J. P. Liu, and Y. Lu, et al., "Wuweizidilactones A-F: novel highly oxygenated nortriterpenoids with unusual skeletons isolated from Schisandra chinensis," Chemistry, vol. 13, pp. 4816-4822, 2007.
[64]J. R. Wang, T. Kurtan, A. Mandi, and Y. W. Guo," Structure and absolute stereochemistry of nortriterpenoids from Schisandra chinensis (Turcz.) Baill," Eur J Org Chem, vol. 28, pp. 5471-5482, 2012.
[65]Y. M. Shi, X. Y. Li, X. N. Li, X. Luo, Y. B. Xue, and C. Q. Liang, et al., "Schicagenins A-C: three cagelike nortriterpenoids from leaves and stems of Schisandra chinensis," Org Lett, vol. 13, pp. 3848-3851, 2011.
[66]S. X. Huang, J. Yang, H. Huang, L. M. Li, W. L. Xiao, and R. T. Li, et al., "Structural characterization of schintrilactone, a new class of nortriterpenoids from Schisandra chinensis," Org Lett, vol. 9, pp. 4175-4178, 2007.
[67]H. sakurai, T. Nikaido, T. Ohmoto, Y. Ikeya, and H. Mitsuhashi, "Inhibitors of adenosine 3', 5'-cyclic monophosphate phosphodiesterase from schisandra chinensis and the structure activity relationship of lignans," Chem Pharm Bull, vol. 40, pp. 1191-1195, 1992.
[68]J. S. Liu, M. F. Huang, Y. L. Gao, and J. A. Findlay, "The structure of chicanine, a new lignan from Schisandra sp.," Can J Chem, vol. 59, pp. 1680-1684, 1981.
[69]Y. Ikeya, H. Taguchi, and I. Yosioka, "The constituents of Schizandra chinensis BAILL. The structures of two new lignans, pre-gomisin F and gomisin J," Chem Pharm Bull, vol. 26, pp. 682-684, 1978.
[70]Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi, "The constituents of Schizandra chinensis BAILL. IV. The structures of two new lignans, pre-gomisin and gomisin J," Chem Pharm Bull, vol. 27, pp. 1583-1588, 1979.
[71]I. S. Lee, K. Y. Jung, S. R. Oh, S. H. Park, K. S. Ahn, and H. K. Lee, "Structure-activity relationships of lignans from Schisandra chinensis as platelet activating factor antagonists," Biol Pharm Bull, vol. 22, pp. 265-267, 1999.
[72]Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi, "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," Chem Pharm Bull, vol. 27, pp. 2695-2709, 1979.
[73]Y. Ikeya, H. Taguchi, H. Mitsuhashi, S. Takeda, Y. Kase, and M. Aburada, "A lignan from Schizandra Chinensis," Phytochemistry, vol. 27, pp. 569-573, 1988.
[74]I. S. Lee, H. K. Lee, N. T. Dat, M. S. Lee, J. W. Kim, and D. S. Na, et al., "Lignans with inhibitory activity against NFAT transcription from Schisandra chinensis," Planta Med, vol. 69, pp. 63-64, 2003.
[75]Y. W. Choi, S. Takamatsu, S. I. Khan, P. V. Srinivas, D. Ferreira, and J. Zhao, et al., "Schisandrene, a dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans," J Nat Prod, vol. 69, pp. 356-359, 2006.
[76]X. X. Liang, G. T. Liu, Q. H. Chen, H. Sun, D. L. Chen, and F. P. Wang, "Synthesis and MDR inhibitory activity evaluation of derivatives of schizandrin A," J Asian Nat Prod Res, vol. 12, pp. 549-556, 2010.
[77]K. Smejkal, T. Slapetova, P. Krmencik, P. Babula, S. Dall'Acqua, and G. Innocenti, et al., "Evaluation of cytotoxic activity of Schisandra chinensis lignans," Planta Med, vol. 76, pp. 1672-1677, 2010.
[78]K. Smejkal, T. Slapetova, P. Krmencik, R. Kubinova, P. Suchy, and S. Dall'Acqua, et al., "Evaluation of the antiradical activity of Schisandra chinensis lignans using different experimental models," Molecules, vol. 15, pp. 1223-1231, 2010.
[79]Y. Ikeya, H. Taguchi, and I. Yosioka, "The constituents of Schizandra chinensis BAILL. VII. The structures of three new lignans, (-)-gomisin K1 and (+)-gomisins K2 and K3," Chem Pharm Bull, vol. 28, pp. 2422-2427, 1980.
[80]D. Hu, Z. Yang, H. Wang, N. Han, and Z. Liu, "Dibenzocyclooctadiene lignans from Schizandra chinensis and their inhibittory activity on NO production in lipopolysaccharide-activated microglia cells," Phytochemistry, vol. 104, pp. 72-78, 2014.
[81]K.M. Ko, "Schisandrin B preparation", US, US2007/20345 A1, 2007.
[82]Y. Ikeya, H. Taguchi, and I. Yosioka, "The constituents of Schizandra chinensis BAILL. X. The structures of γ-schizandrin and four new lignans, (-)-gomisins L1 and L2, (±)-gomisin M1 and (+)-gomisin M2," Chem Pharm Bull, vol. 30, pp. 132-139, 1982.
[83]M. Tanaka, T. Ohshima, H. Mitsuhashi, M. Maruno, and T. Wakamatsu, "Total syntheses of the lignans isolated from Schizandra chinensis," Terrahedron, vol. 51, pp. 11693-11702, 1995.
[84]N. Chen, P. Y. Chiu, and K. M. Ko, "Schisandrin B enhances cerebral mitochondrial antioxidant status and structural integrity, and protects against cerebral ischemia/reperfusion injury in rats," Biol Pharm Bull, vol. 31, pp. 1387-1391, 2008.
[85]P. Y. Chiu, H. Y. Leung, and K. M. Ko, "Schisandrin B enhances renal mitochondrial antioxidant status, functional and structural integrity, and protects against gentamicin-induced nephrotoxicity in rats," Biol Pharm Bull, vol. 31, pp. 602-605, 2008.
[86]S. Y. Pan, H. Dong, X. Y. Zhao, C. J. Xiang, H. Y. Fang, and W. F. Fong, et al., "Schisandrin B from Schisandra chinensis reduces hepatic lipid contents in hypercholesterolaemic mice," J Pharm Pharmacol, vol. 60, pp. 399-403, 2008.
[87]P. Y. Chiu, D. H. Mak, M. K. Poon, and K. M. Ko, "Role of cytochrome P-450 in schisandrin B-induced antioxidant and heat shock responses in mouse liver," Life Sci, vol. 77, pp. 2887-2895, 2005.
[88]X. Hu, "Methods of application of chemical compounds having therapeutic activities in treating cancers", US, US2005/0282910 A1, 2005.
[89]Y. Ikeya, H. Taguchi, and I. Yosioka, "The constituents of Schizandra chinensis BAILL. XII. Isolation and structure of a new lignan, gomisin R, the absolute structure of wuweizisu C and isolation of schisantherin D," Chem Pharm Bull, vol. 30, pp. 3207-3211, 1982.
[90]Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi, "The constituents of Schizandra chinensis BAILL. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F, and G, and the absolute structure of schizandrin," Chem Pharm Bull, vol. 27, pp. 1383-1394, 1979.
[91]J. C. Jung, I. A. Khan, and Y. W. Choi, "Isolation and synthesis of dibenzocyclooctadiene lignans: (±)‐schizandrin and its analogues," Synthetic Communications, vol. 36, pp. 2259-2268, 2006.
[92]W. F. Fong, C. K. Wan, G. Y. Zhu, A. Chattopadhyay, S. Dey, and Z. Zhao, et al., "Schisandrol A from Schisandra chinensis reverses P-glycoprotein-mediated multidrug resistance by affecting Pgp-substrate complexes," Planta Med, vol. 73, pp. 212-220, 2007.
[93]M. Tanaka, C. Mukaiyama, H. Mitsuhashi, M. Maruno, and T. Wakamatsu, "Synthesis of optically pure gomisi lignans: the total synthesis of (+)-schizandrin, (+)-gomisin A, and (+)-isoschizandrin in naturally occurring forms," J. Org. Chem, vol. 60, pp. 4339-4352, 1995.
[94]M. Blunder, E. M. Pferschy-Wenzig, W. M. Fabian, A. Hufner, O. Kunert, and R. Saf, et al., "Derivatives of schisandrin with increased inhibitory potential on prostaglandin E(2) and leukotriene B(4) formation in vitro," Bioorg Med Chem, vol. 18, pp. 2809-2815, 2010.
[95]Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi, "The constituents of Schizandra chinensis BAILL.Ⅲ. The structures of four new lignans, gomisin H, and its derivatives, angeloyl-, tigloyl- and benzoyl-gomisin H," Chem Pharm Bull, vol. 27, pp. 1576-1582, 1979.
[96]Y. Ikeya, H. Taguchi, and I. Yosioka, "The constituents of Schizandra chinensis BAILL. The structures of three new lignans, angeloylgomisin H, tigloylgomisin H and benzoylgomisin H, and the absolute structure of schizandrin," Chem Pharm Bull, vol. 26, pp. 328-331, 1978.
[97]Y. Ikeya, H. Kanatani, M. Hakozaki, H. Taguchi, and H. Mitsuhashi, "The constituents of Schizandra chinensis BAILL. XV. Isolation and structure determination of two new lignans, gomisin S and gomisin T," Chem Pharm Bull, vol. 36, pp. 3974-3979, 1988.
[98]Y. Ikeya and H. Taguchi, "The constituents of Schizandra chinensis BAILL. I. The structures of gomisin A, B and C," Chem Pharm Bull, vol. 23, pp. 3296-3298, 1975.
[99]J. Y. Park, S. J. Lee, M. R. Yun, K. W. Seo, S. S. Bae, and J. W. Park, et al.,"Gomisin A from Schisandra chinensis induces endothelium-dependent and direct relaxation in rat thoracic aorta," Planta Medica, vol. 73, pp. 1537-1542, 2007.
[100]D. Hwang, S. Y. Shin, Y. Lee, J. Hyun, Y. Yong, and J. C. Park, et al.,"A compound isolated from Schisandra chinensis induces apoptosis," Bioorg Med Chem Lett, vol. 21, pp. 6054-6057, 2011.
[101]Y. Ikeya, H. Taguchi, I. Yosioka, and N. Ookawa, "The constituents of Schizandra chinensis BAILL. XI. The structures of three new lignans, angeloylgomisin O, and angeloyl- and benzoylisogomisin O," Chem Pharm Bull, vol. 30, pp. 3202-3206, 1982.
[102]Y. Ikeya, H. Taguchi, and I. Yosioka, "The constituents of Schizandra chinensis BAILL. The cleavage of the methylenedioxy moiety with lead tetraacetate in benzene, and the structure of angeloylgomisin Q," Chem Pharm Bull, vol. 27, pp. 2536-2538, 1979.
[103]Y. Ikeya and H. Taguchi, "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," Chem Pharm Bull, vol. 25, pp. 364-366, 1977.
[104]Y. Ikeya, H. Taguchi, and I. Yosioka, and H. Kobayashi, "The constituents of Schizandra chinensis BAILL. The structure of two new lignans, gomisin N and tigloylgomisin G," Chem Pharm Bull, vol. 26, pp. 3257-3260, 1978.
[105]Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi, "The constituents of Schizandra chinensis BAILL. VIII. The structures of two new lignans, tigloylgomisin P and angeloylgomisin P," Chem Pharm Bull, vol. 28, pp. 3357-3361, 1980.
[106]董文雪, 舒永志, 劉意, 何泉泉, 延在昊, "南五味子屬植物化學成分及藥理作用研究發展," 中草藥Chinese Traditional and Herbal Drugs, vol. 45, pp. 1938-1959, 2014.
[107]A. R. Carroll, R. W. Read, and W. C. Taylor, "Intramolecular oxidative coupling of aromatic compounds. VII. A convenient synthesis of (±)-deoxyschizandrin," Aust J Chem, vol. 47, pp. 1579-1589, 1994.
[108]X. M. Gao, R. R. Wang, D. Y. Niu, C. Y. Meng, L. M. Yang, and Y. T. Zheng, et al., "Bioactive dibenzocyclooctadiene lignans from the stems of Schisandra neglecta," J Nat Prod, vol. 76, pp. 1052-1057, 2013.
[109]M. A. Brook, F. Gonzaga, and H. Tian, "Chelating silicon-based polymers", US, PCT/CA2006/001291, 2007.
[110]P. Heretsch, F. Thomas, A. Aurich, H. Krautscheid, D. Sicker, and A. Giannis, "Syntheses with a chiral building block from the citric acid cycle: (2R,3S)-isocitric acid by fermentation of sunflower oil," Angew Chem Int Ed Engl, vol. 47, pp. 1958-1960, 2008.
[111]J. Holecek, A. Lycka, D. Micak, L. Nagy, G. Vanko, and J. Brus, et al., "Infrared, 119Sn, 13C and 1H NMR, 119Sn and 13C CP/MAS NMR and moessbauer spectral study of some tributylstannyl citrates and propane-1,2,3-tricarboxylates, " Collect Czech Chem Commun, vol. 64, pp. 1028-1048, 1999.
[112]R. Arora, A. P. Vig, and S. Arora, "Lipid Peroxidation: A Possible Marker for Diabetes," J Diabetes Metab, doi:10.4172/2155-6156, S11:007, 2013.