Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: Absolute configuration, and their estrogenic and anti-proliferative activity

European Journal of Medicinal Chemistry

Volumn 59, Issue , 2013, Pages 265-273

  Liu, Han Wei ^a   Yu, Xiu Zhu ^a   Padula, Daniele ^b   Pescitelli, Gennaro ^b   Lin, Zhi Wei ^c   Wang, Fei ^c   Ding, Kai ^d   Lei, Ming ^a   Gao, Jin Ming ^a  

^a NORTHWEST A F UNIVERSITY   (China)

^b UNIVERSITY OF PISA   (Italy)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

^d SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Antitumor agents; Circular dichroism; Estrogenic activity; Natural products; Schisandra sphenathera Rehd. et Wils; Structure elucidation

Indexed keywords

6,7 SECOSCHISANTHEROL A; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]BUTYRATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]DECANOATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]DODECANOATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]HEPTANOATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]HEXANOATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]NONYLATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]OCTANOATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]PALMITATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]PENTANOATE; 6,7,8,9,9,18,18 HEPTAHYDRO 1,2,3,14 TETRAMETHOXY 8 METHYL[DIBENZO[A,C]CYCLOOCTENE]TETRADECANOATE; ANTINEOPLASTIC AGENT; ESTROGEN; GOMISIN; LIGNAN DERIVATIVE; OXOALDEHYDE; SCHISANDRIN A1; SCHISANTHEROL A; UNCLASSIFIED DRUG; WUWEIZISU C;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CALCULATION; CANCER CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DOSE RESPONSE; DRUG CYTOTOXICITY; DRUG POTENCY; ESTROGEN ACTIVITY; HUMAN; HUMAN CELL; HUMAN TISSUE; NONHUMAN; PLANT STEM; SCHISANDRA; SCHISANDRA SPHENATHERA; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTROGENS; HUMANS; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUANTUM THEORY; SCHISANDRA;

EID: 84870663765     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.11.003     Document Type: Article

References (48)

1. Y. Lu, and D.-F. Chen J. Chromatogr. A 1216 2009 1980 1990
2. Y.C. Shen, Y.B. Cheng, T.W. Lan, C.C. Liaw, S.S. Liou, Y.H. Kuo, and A.T. Khalil J. Nat. Prod. 70 2007 1139 1145
3. C.C. Liu, M.H. Abd El-Razek, C.C. Liaw, Y.B. Cheng, C.K. Chen, C.T. Chien, Y.H. Kuo, S.S. Liou, and Y.C. Shen Planta Med. 76 2010 1605 1610
4. X.N. Li, J.X. Pu, X. Du, L.M. Yang, H.M. An, C. Lei, F. He, X. Luo, Y.T. Zheng, Y. Lu, W.L. Xiao, and H.D. Sun J. Nat. Prod. 72 2009 1133 1141
5. W.L. Xiao, L.M. Yang, H.B. Zhang, Y.B. Xue, G.Y. Yang, J.X. Pu, R.R. Wang, Y.T. Zheng, and H.D. Sun Chem. Pharm. Bull. 58 2010 852 855
6. W. Ma, X. Ma, H. Huang, P. Zhou, and D. Chen Chem. Biodiversity 4 2007 966 972
7. Y.B. Cheng, M.T. Chang, Y.W. Lo, C.J. Ho, Y.C. Kuo, C.T. Chien, S.Y. Chen, S.S. Liou, Y.H. Kuo, and Y.C. Shen J. Nat. Prod. 72 2009 1663 1668
8. X. Ci, R. Ren, K. Xu, H. Li, Q. Yu, Y. Song, D. Wang, R. Li, and X. Deng Inflammation 33 2010 126 136
9. Y. Jiang, G.Z. Yang, Y. Chen, M.C. Liao, X.M. Liu, S. Chen, L. Liu, and X.X. Lei Helv. Chim. Acta 94 2011 491 496
10. F. He, J.-X. Pu, S.-X. Huang, Y.-Y. Wang, W.-L. Xiao, L.-M. Li, J.-P. Liu, H.-B. Zhang, Y. Li, and H.-D. Sun Org. Lett. 12 2010 1208 1211
11. R. Ren, G.J. Luo, H.M. Li, Z.Y. Wu, H.Z. Li, and R.T. Li Chin. Chem. Lett. 20 2009 601 603
12. Y. Ikeya, E. Miki, M. Okada, H. Mitsuhashi, and J.G. Chai Chem. Pharm. Bull. 38 1990 1408 1411
13. L. Li, and H. Xue Planta Med. 1985 217 219
14. H. Taguchi, and Y. Ikeya Chem. Pharm. Bull. 25 1977 364 366
15. Y. Ikeya, H. Taguchi, and I. Yosioka Chem. Pharm. Bull. 30 1982 3207 3211
16. Y. Ikeya, H. Taguchi, H. Sasaki, K. Nakajima, and I. Yosioka Chem. Pharm. Bull. 28 1980 2414 2421
17. Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi Chem. Pharm. Bull. 28 1980 3357 3361
18. W.H. Ma, J.C. He, P.S. Duan, T. Han, C.J. Zheng, and L.P. Qin Biochem. Syst. Ecol. 38 2010 1156 1159
19. H. Tsukamoto, S. Hisada, and S. Nishibe Chem. Pharm. Bull. 32 1984 2730 2735
20. H. Yin, H. Fu, H. Hua, and Y. Pei J. Shenyang Pharm. Univ. 23 2006 641 645
21. F. Xie, C. Zhang, B. Yu, M. Zhang, and Z. Wang Chin. Pharm. J. 43 2008 1066 1069
22. S.J. Jiang, Y.H. Wang, and D.F. Chen Chin. J. Nat. Med. 3 2005 78 82
23. M. Chen, Z. Liao, and D. Chen Helv. Chim. Acta 87 2004 1368 1376
24. Y. Ikeya, H. Taguchi, I. Yosioka, and H. Kobayashi Chem. Pharm. Bull. 27 1979 1383 1394
25. K. Mislow, M.A.W. Glass, R.E. O'Brien, P. Rutkin, D.H. Steinberg, J. Weiss, and C. Djerassi J. Am. Chem. Soc. 84 1962 1455 1478
26. P. Rashidi-Ranjbar, and J. Sandström J. Mol. Struct. 246 1991 25 32
27. J. Gawroński, P. Grycz, M. Kwit, and U. Rychlewska Chem. Eur. J. 8 2002 4210 4215
28. L.-N. Li, and H. Xue Phytochemistry 29 1990 2730 2732
29. N. Harada, and K. Nakanishi Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry 1983 University Science Books Mill Valley, CA
30. J.-H. Yang, H.-Y. Zhang, X. Du, W. Wang, W.-L. Xiao, J. Wen, J.-X. Pu, X.-C. Tang, and H.-D. Sun Tetrahedron 67 2011 4498 4504
31. Y.-W. Choi, S. Takamatsu, S.I. Khan, P.V. Srinivas, D. Ferreira, J. Zhao, and I.A. Khan J. Nat. Prod. 69 2005 356 359
32. R. Schobert, W. Kern, W. Milius, T. Ackermann, and M. Zoldakova Tetrahedron Lett. 49 2008 3359 3362
33. J. Autschbach, L. Nitsch-Velasquez, and M. Rudolph R. Naaman, D.N. Beratan, D. Waldeck, Topics in Current Chemistry vol. 298 2011 Springer Berlin/Heidelberg 1 98
34. G. Pescitelli, L. Di Bari, and N. Berova Chem. Soc. Rev. 40 2011 4603 4625
35. G. Pescitelli, T. Kurtán, U. Flörke, and K. Krohn Chirality 21 2009 E181 E201
36. G. Kerti, T. Kurtán, A. Borbás, Z.B. Szabó, A. Lipták, L. Szilágyi, Z. Illyés-Tünde, A.C. Bényei, S. Antuš, M. Watanabe, E. Castiglioni, G. Pescitelli, and P. Salvadori Tetrahedron 64 2008 1676 1688
37. G. Pescitelli Chirality 24 2012 718 724
38. L.S. Richelson, H.W. Wahner, L.J. Melton, and B.L. Riggs New Engl. J. Med. 311 1984 1273 1275
39. R.T. Turner, B.L. Riggs, and T.C. Spelsberg Endocr. Rev. 15 1994 275 300
40. S. Davison, and S.R. Davis Clin. Endocrinol. 58 2003 249 261
41. M.-T. Ling, X. Wang, X. Zhang, and Y.-C. Wong Differentiation 74 2006 481 487
42. G.M. Sheldrick SHELXTL-97-A Program for Refining Crystal Structure 1997 University of Goettingen Goettingen, Germany
43. L. Yang, Q. Chen, F. Wang, and G. Zhang J. Ethnopharmacol. 135 2011 553 560
44. H. Qiu, B. Yang, Z.-C. Pei, Z. Zhang, and K. Ding J. Biol. Chem. 285 2010 32638 32646
45. J.C. Qin, Y.M. Zhang, J.M. Gao, M.S. Bai, S.X. Yang, H. Laatsch, and A.L. Zhang Bioorg. Med. Chem. Lett. 19 2009 1572 1574
46. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnemberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.02 2009 Gaussian, Inc. Wallingford CT
47. All references about DFT functionals and basis sets can be found in the on-line documentation for Gaussian'09 at www.gaussian.com/g-tech/g-ur/g09help. htm
48. T. Bruhn, Y. Hemberger, A. Schaumlöffel, and G. Bringmann Specdis v. 1.53 (beta) 2012 University of Würzburg Germany