Identification of GABA A receptor modulators in Kadsura longipedunculata and assignment of absolute configurations by quantum-chemical ECD calculations

Phytochemistry

Volumn 72, Issue 18, 2011, Pages 2385-2395

  Zaugg, Janine ^a   Ebrahimi, Samad Nejad ^a,b   Smiesko, Martin ^a   Baburin, Igor ^c   Hering, Steffen ^c   Hamburger, Matthias ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

^c MEDICAL UNIVERSITY OF VIENNA   (Austria)

Author keywords

Circular dichroism; GABA A receptor; HPLC based activity profiling; Kadsura longipedunculata; Lignans; Quantum chemical calculations; Schisandraceae; Terpenoids

Indexed keywords

4 AMINOBUTYRIC ACID A RECEPTOR; GABAERGIC RECEPTOR AFFECTING AGENT; PLANT EXTRACT;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; KADSURA; METABOLISM; OOCYTE; PATCH CLAMP; XENOPUS LAEVIS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GABA AGENTS; KADSURA; OOCYTES; PATCH-CLAMP TECHNIQUES; PLANT EXTRACTS; RECEPTORS, GABA-A; XENOPUS LAEVIS;

KADSURA; KADSURA JAPONICA; KADSURA LONGIPEDUNCULATA; SCHISANDRA CHINENSIS; SCHISANDRACEAE; XENOPUS LAEVIS;

EID: 80054950667     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.08.014     Document Type: Article

References (58)

1. M. Adams, S. Zimmermann, M. Kaiser, R. Brun, and M. Hamburger A protocol for HPLC-based activity profiling for natural products with activities against tropical parasites Nat. Prod. Comm. 4 2009 1377 1381
2. J. Ai, X. Wang, and M. Nielsen Honokiol and magnolol selectively interact with GABAA receptor subtypes in vitro Pharmacology 63 2001 34 41 (Pubitemid 32623459)
3. I. Baburin, S. Beyl, and S. Hering Automated fast perfusion of Xenopus oocytes for drug screening Pflug. Arch. Eur. J. Phy. 453 2006 117 123 (Pubitemid 44454892)
4. F. Bohlmann, M. Ahmed, R.M. King, and H. Robinson Acetylenic compounds from Bidens graveolens Phytochemistry 22 1983 1281 1283
5. G. Bringmann, T. Bruhn, K. Makismenka, and Y. Hemberger The assignement of absolute stereostructures through quantum chemical circular dichroism calculations Eur. J. Org. Chem. 17 2009 2717 2727
6. 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 Oxygenated lignans from the fruits of Schisandra arisanensis J. Nat. Prod. 72 2009 1663 1668
7. T. da Silva, and L.M.X. Lopes Aryltetralone lignans and 7, 8-seco-lignans from Holostylis reniformis Phytochemistry 65 2004 751 759 (Pubitemid 38315136)
8. H. Danz, S. Stoyanova, P. Wippich, A. Brattstroem, and M. Hamburger Identification and isolation of the cyclooxygenase-2 inhibitory principle in Isatis tinctoria Planta Med. 67 2001 411 416 (Pubitemid 32652575)
9. K. Dittmann, C. Gerhaeuser, K. Klimo, and M. Hamburger HPLC-based activity profiling of Salvia miltiorrhiza for MAO A and iNOS inhibitory activities Planta Med. 70 2004 909 913 (Pubitemid 39457799)
10. C. Enzell, and H. Erdtman The chemistry of the natural order Cupressales-XXI Cuparene and Cuparenic acid, two sesquiterpenic compounds with a new carbon skeleton Tetrahedron 4 1958 361 368
11. J. Fluegge Grundlagen der Polarimetrie 1970 De Gruyter-Verlag Berlin
12. Frisch, M. J.; Trucks, H. B.; Schlegel, H. B.; Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr.; T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, 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, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc.; Wallingford CT.; 2004.
13. N. Fujita Über die Früche der Schizandra chinensis Bail Und Kadsura japonica Dun Arch. Pharm. Ber. Deutsch. Pharm. Ges. 267 1929 532 540
14. Haensel, R.; Keller, K.; Rimpler, H.; Schneider, G.; 1993. Hagers Handbuch der pharmazeutischen Praxis. Springer Verlag.
15. J.L. Hancke, R.A. Burgos, and R. Ahumada Schisandra chinensis (Turcz.) Baill Fitoterapia 70 1999 451 471
16. J.P. Hou, and J. Youyu The Healing Power of Chinese Herbs and Medicinal Recipes 2005 The Haworth Press New York, London, Oxford
17. F. Huang, Y. Xiong, L. Xu, S. Ma, and C. Dou Sedative and hypnotic activities of the ethanol fraction from Fructus Schisandrae in mice and rats J. Ethnopharmacol. 110 2007 471 475 (Pubitemid 46386359)
18. Y. Ikeya, H. Taguchi, H. Sasaki, K. Nakajima, and I. Yosioka The constituents of Schizandra chinensis BAILL. VI. 13C nuclear magnetic resonance spectroscopy of dibenzocyclooctadiene lignans Chem. Pharm. Bull 28 1980 2414 2421
19. 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. 27 1979 2695 2709
20. S. Ito, K. Endo, H. Honma, and K. Ota New constituents of Thujopsis dolabrata Tetrahedron Lett. 42 1965 3777 3781
21. H.N. Kamel, Y. Ding, X.C. Li, D. Ferreira, F.R. Fronczek, and M. Slattery Beyond Polymaxenolide: Cembrane-Africane Terpenoids from the Hybrid Soft Coral Sinularia maxima × S Polydactyla J. Nat. Prod. 72 2009 900 905
22. S. Khom, I. Baburin, E.N. Timin, A. Hohaus, W. Sieghart, and S. Hering Pharmacological properties of GABA(A) receptors containing gamma1 subunits Mol. Pharmacol. 69 2006 640 649 (Pubitemid 43121961)
23. H.J. Kim, I. Baburin, S. Khom, S. Hering, and M. Hamburger HPLC-based activity profiling approach for the discovery of GABA(A) receptor ligands using an automated two microelectrode voltage clamp assay on Xenopus oocytes Planta Med. 74 2008 521 526 (Pubitemid 351655969)
24. C.-L. Lee The extractive components of formosan lauraceous plants I Four lignans from the bark of Machilus zuihoensis forma longipaniculata Kexue-Fazhan 9 1981 578 583
25. Y. Li, I. Plitzko, J. Zaugg, S. Hering, and M. Hamburger HPLC-based activity profiling for GABA(A) receptor modulators: a new dihydroisocoumarin from Haloxylon scoparium J. Nat. Prod. 73 2010 768 770
26. Liu, J.; Tao, Y.; Huang, M.; 1988. Studies on the constituents of Schisandra henryi. V. Structures of wulignan A1, A2, epiwulignan A1 and epischisandrone Huaxue Xuebao 46, 483-488.
27. Y. Lu, and D.F. Chen Analysis of Schisandra chinensis and Schisandra sphenanthera J. Chromatogr. A 1216 2009 1980 1990
28. C. Methfessel, V. Witzemann, T. Takahashi, M. Mishina, S. Numa, and B. Sakmann Patch clamp measurements on Xenopus laevis oocytes: currents through endogenous channels and implanted acetylcholine receptor and sodium channels Pflug. Arch. Eur. J. Phy. 407 1986 577 588 (Pubitemid 17049013)
29. M. Miyazawa, H. Kasahara, and H. Kameoka O-Demethylation of meso-dimethyldihydroguaiaretic acid in Spodoptera litua Phytochemistry 46 1997 1173 1175 (Pubitemid 28000412)
30. H. Mohler The rise of a new GABA(A) pharmacology Neuropharmacology 60 2011 1042 1049
31. N. Nakatani, K. Ikeda, H. Kikuzaki, M. Kido, and Y. Yamaguchi Diaryldimethylbutane lignans from Myristica argentea and their antimicrobial action against Streptococcus mutans Phytochemistry 27 1988 3127 3129
32. A. Nayek, M.G.B. Drew, and S. Ghosh Convenient route to enantiopure aryl cyclopentanes via Diels-Alder reaction of assymetric dienes. Total synthesis of (+)-herbertene and (+)-cuparene Tetrahedron 59 2003 5175 5181 (Pubitemid 36929739)
33. R.W. Olsen, and W. Sieghart International Union of Pharmacology LXX. Subtypes of gamma-aminobutyric acid(A) receptors: classification on the basis of subunit composition, pharmacology, and function. Update Pharmacol. Rev. 60 2008 243 260
34. N. Ookawa, Y. Ikeya, H. Taguchi, and I. Yosioka The constituents of Kadsura japonica Dunal I. The structures of three new lignans, acetyl- angeloyl- and caproyl-binankadsurin A. Chem. Pharm. Bull. 29 1981 123 127 (Pubitemid 11131685)
35. L. Opletal, H. Sovova, and M. Bartlova Dibenzo[a, c]cyclooctadiene lignans of the genus Schisandra: importance, isolation and determination J. Chromatogr. B 812 2004 357 371 (Pubitemid 39535421)
36. H. Pajouhesh, and G.R. Lenz Medicinal chemical properties of successful central nervous system drugs NeuroRx 2 2005 541 553 (Pubitemid 41393264)
37. A. Panossian, and G. Wikman Pharmacology of Schisandra chinensis Bail.: an overview of Russian research and uses in medicine J. Ethnopharmacol. 118 2008 183 212
38. Y.Q. Pei, W. Yue, J.R. Cui, and H.Y. Yao A study of the central pharmacological action of piperine and its derivatives Yao Xue Xue Bao 15 1980 198 205
39. O. Potterat, and M. Hamburger Natural products in drug discovery - concepts and approaches for tracking bioactivity Curr. Org. Chem. 10 2006 899 920
40. O. Potterat, K. Wagner, G. Gemmecker, J. Mack, C. Puder, R. Vettermann, and R. Streicher BI-32169, a bicyclic 19-peptide with strong glucagon receptor antagonist activity from Streptomyces sp J. Nat. Prod. 67 2004 1528 1531 (Pubitemid 39298622)
41. S.K. Sadhu, E. Okuyama, H. Fujimoto, and M. Ishibashi Separation of Leucas aspera, a medicinal plant of Bangladesh, guided by prostaglandin inhibitory and antioxidant activities Chem. Pharm. Bull. 51 2003 595 598 (Pubitemid 41656816)
42. R.K.M. Saunders Monograph of Kadsura (Schisandraceae) Systematic Botany Monographs 54 1998 1 106
43. R.K.M. Saunders Monograph of Schisandra (Schisandraceae) Systematic Botany Monographs 58 2000 1 146
44. A.W. Schrecker Meso-Dihydroguaiaretic acid and its derivatives J. Am. Chem. Soc. 79 1957 3823 3827
45. E.A. Stoeger Arzneibuch der Chinesischen Medizin. Monographien des Arzneibuches der Volksrepublik China 2000 und 2005 2009 Deutscher Apotheker Verlag Stuttgart
46. W. Tang, and G. Eisenbrand Handbook of Chinese Medicinal Plants. Chemistry, Pharmacology, Toxicology 2011 Wiley-VCH Weinheim
47. W.C. Tayone, M. Honma, S. Kanamaru, S. Noguchi, K. Tanaka, T. Nehira, and M. Hashimoto Stereochemical Investigations of Isochromenones and Isobenzofuranones Isolated from Leptosphaeria sp. KTC 727 J. Nat. Prod. 74 2011 425 429
48. A. Urzua, A.J. Freyer, and M. Shamma 2, 5-Diaryl-3, 4- dimethyltetrahydrofuranoid lignans Phytochemistry 26 1987 1509 1511
49. B.G. Wang, X. Hong, L. Li, J. Zhou, and X.J. Hao Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation Planta Med. 66 2000 6107 6112
50. Q. Wang, Y. Yang, Y. Li, W. Yu, and Z.J. Hou An efficient method for the synthesis of lignans Tetrahedron 62 2006 6107 6112 (Pubitemid 43728076)
51. H. Wei, L. Sun, Z. Tai, S. Gao, W. Xu, and W. Chen A simple and sensitive HPLC method for the simultaneous determination of eight bioactive components and fingerprint analysis of Schisandra sphenanthera Anal. Chim. Acta 662 2010 97 104
52. P.-G. Xiao, L.-J. Xu, W. Xiao, and Y. Peng Argument on the correct Chinese name of genus Kadsura Kaempf.ex Juss Yao Xue Xue Bao 45 2010 1064 1066
53. Yang, X.; Baburin, I.; Plitzko, I.; Hering, S.; Hamburger, M.; 2011. HPLC-based activity profiling for GABA(A) receptor modulators from the traditional Chinese herbal drug Kushen (Sophora flavescens root). Mol. Diversity DOI: 10.1007/s11030-010-9297-7.
54. J. Zaugg, I. Baburin, B. Strommer, H.J. Kim, S. Hering, and M. Hamburger HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site J. Nat. Prod. 73 2010 185 191
55. Zaugg, J.; Eickmeier, E.; Ebrahimi, S.; Baburin, I.; Hering, S.; Hamburger, M.; 2011a. HPLC-based activity profiling for positive GABA(A) receptor modulators in Acorus calamus L. J. Nat. Prod. dx.doi.org/10.1021/ np200181d.
56. J. Zaugg, E. Eickmeier, D.C. Rueda, S. Hering, and M. Hamburger HPLC-based activity profiling of Angelica pubescens roots for new positive GABA(A) receptor modulators in Xenopus oocytes Fitoterapia 82 2011 434 440
57. Zaugg, J.; Khom, S.; Eigenmann, D.; Baburin, I.; Hamburger, M.; Hering, S.; 2011c. Identification and characterization of GABA(A) receptor modulatory and sedative diterpenes from Biota orientalis twigs and leaves. J. Nat. Prod. submitted for publication.
58. M. Zhu, X.-S. Chen, and K.-X. Wang Variation of the lignan content of Schisandra chinensis (Turcz.) Baill And Schisandra sphenanthera Rehd. et Wils Chromatographia 66 2007 125 128 (Pubitemid 47030174)