Volvalerenone A, a new type of mononorsesquiterpenoid with an unprecedented 3,12-oxo bridge from Valeriana officinalis

Tetrahedron Letters

Volumn 51, Issue 41, 2010, Pages 5451-5453

  Wang, Peng Cheng ^a,c   Ran, Xin Hui ^a   Chen, Rui ^a   Li, Liang Chun ^d   Xiong, Shan Shan ^e   Liu, Yu Qing ^a   Luo, Huai Rong ^a   Zhou, Jun ^a   Zhao, You Xing ^a,b  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b INSTITUTE OF TROPICAL BIOSCIENCE AND BIOTECHNOLOGY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^d CHENGDU INSTITUTE OF BIOLOGY   (China)

^e YUNNAN UNIVERSITY   (China)

Author keywords

AChE inhibitory activity; Mononorsesquiterpenoid; Valeriana officinalis; Valerianacae; Volvalerenone A

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITOR; NERVE GROWTH FACTOR; SESQUITERPENOID; TACRINE; UNCLASSIFIED DRUG; VOLVALERENONE A;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; NERVE FIBER GROWTH; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; VALERIANA OFFICINALIS; X RAY CRYSTALLOGRAPHY;

VALERIANA; VALERIANA OFFICINALIS;

EID: 79958775901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.023     Document Type: Article

References (32)

1. P.J. Houghton J. Pharm. Pharmacol. 51 1999 505 512
2. C.S. Yuan, S. Mehendale, Y.P. Xiao, H.H. Aung, J.T. Xie, and M.K. Ang-lee Anesth. Analg. 98 2004 353 358
3. A.L. Piccinelli, S. Arana, A. Caceres, E.B. Roberta, S. Raffaella, and R. Luca J. Nat. Prod. 67 2004 1135 1140
4. WHO monographs on selected medicinal plants: Radix valerianae; WHO: Geneva, Switzerland, 1999; Vol. 1, pp 267-276.
5. Y.P. Tang, X. Liu, and B. Yu J. Nat. Prod. 6 2002 1949 1952
6. R. Bos, H. Hendriks, A.P. Bruins, J. Kloosterman, and G. Sipma Phytochemistry 25 1985 133 135
7. D.S. Ming, D.Q. Yu, Y.Y. Yang, and C.M. He Tetrahedron Lett. 38 1997 5205 5208
8. T. Kurt, and W. Kerstin Tetrahedron Lett. 7 1966 445 448
9. H.R. Pharmaratne, N.P. Nanayakkara, and I.K. Khan Planta Med. 15 2002 661 662
10. S. Lin, Y.H. Shen, H.L. Li, X.W. Yang, T. Chen, L.H. Lu, Z.S. Huang, R.H. Liu, X.K. Xu, W.D. Zhang, and H. Wang J. Nat. Prod. 72 2009 650 655
11. L.L. Yu, C.R. Han, R. Huang, Y.P. Lv, S.H. Gui, and Y.G. Chen Pharmazie 61 2006 486 488
12. R. Wang, D. Xiao, Y.H. Bian, X.Y. Zhang, B.J. Li, L.S. Ding, and S.L. Peng J. Nat. Prod. 71 2008 1254 1257
13. E.A. Carlini Pharmacol. Biochem. Behav. 75 2003 501 512
14. P.D. Leathwood, F. Chauffard, E. Heck, and R. Munoz-Box Pharmacol. Biochem. Behav. 17 1982 65 71
15. P. Morazzoni, and E. Bombardelli Fitoterapia 66 1995 99 112
16. H. Miguel, Feistelb, S. Hartwig, L. Romanus, H. Mirjam, and W. Hilke Phytomedicine 15 2008 2 15
17. B. Hazelhoff, D. Smith, and T.M. Malingre Arch. Int. Pharmacodyn. 257 1982 274 287
18. N. Murakami, Y. Ye, M. Kawanishi, S. Aoki, N. Kudo, M. Yoshida, E. Nakayama, T. Shiodac, and M. Kobayashia Bioorg. Med. Chem. Lett. 12 2002 2807 2810
19. C. Clara, D.P. Rita, S. Stefania, P. Annalisa, and O. Francesco J. Ethnopharmacol. 112 2007 361 367
20. P.C. Wang, J.M. Hu, X.H. Ran, Z.Q. Cheng, H.Z. Jiang, Y.Q. Liu, J. Zhou, and Y.X. Zhao J. Nat. Prod. 72 2009 1682 1685
21. + 275.1259).
22. 2 = 0.1357. The crystal structure of compound 1 was solved by direct method SHLXS-97 (Sheldrick, 1990) and expanded using the difference Fourier technique, refined by the program SHLXL-97 (Sheldrick, 1997), and the full-matrix least-squares calculations. Crystallographic data for the structure of compound 1 have been deposited with the Cambridge Crystallographic Data Centre (deposition no. CCDC 776982). These data can be obtained free of charge via www.ccdc.cam.ac.uk/data- request/cif, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
23. Y. Zhang, Y.T. Di, Q. Zhang, S.Z. Mu, C.J. Tan, X. Fang, H.P. He, C.S. Li, and X.J. Hao Org. Lett. 11 2009 5414 5417
24. Q. Zhang, Y.T. Di, C.S. Li, X. Fang, C.J. Tan, Z. Zhang, Y. Zhang, H.P. He, S.L. Li, and X.J. Hao Org. Lett. 11 2009 2357 2359
25. H.M. Ge, C.H. Zhu, D.H.L. Shi, D. Zhang, D.Q. Xie, J. Yang, S.W. Ng, and R.X. Tan Chem. Eur. J. 14 2008 376 381
26. S.P. Karna, and M. Dupuis J. Comput. Chem. 12 1991 487 504
27. R.K. Kondru, W. Peter, and D.N. Beratan J. Am. Chem. Soc. 120 1998 2204 2205
28. Frisch, M. J. Gaussian 03, revision E. 01; gaussian, Inc.: Wallingford, CT, 2004 (see Supplementary data for complete reference).
29. J. Ramharter, and J. Mulzer Org. Lett. 11 2009 1151 1153
30. The Unites States Pharmacopeia and the National Formulary (USP 24/NF 19); The United States Pharmacopeial Convention: Rockville (MD), 2000, pp 2533-2534.
31. G.L. Ellman, K.D. Courtney, V.J. Andres, and R.M. Featherstone Biochem. Pharmacol. 7 1961 88 95
32. H. Imagawa, H. Saijo, T. Kurisaki, H. Yamamoto, M. Kubo, Y. Fukuyama, and M. Nishizawa Org. Lett. 11 2009 1253 1255