Isolation and chemical modification of clerodane diterpenoids from Salvia species as potential agonists at the κ-opioid receptor

Chemistry and Biodiversity

Volumn 4, Issue 7, 2007, Pages 1586-1593

  Li, Yiqiang ^a   Husbands, Stephen M ^a   Mahon, Mary F ^b   Traynor, John R ^c   Rowan, Michael G ^a  

^a University of Bath   (United Kingdom)

^b University of Bath Claverton Down   (United Kingdom)

^c UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10ALPHA 1 ACETOXY 7,17:12,17:15,16 TRIEPOXY 2 HYDROXYCLERODA 3,13(16),14 TRIENE 18,19 OLID; 10ALPHA 2 ACETOXY 7,17:12,17:15,16 TRIEPOXY 1 HYDROXYCLERODA 3,13(16),14 TRIENE 18,19 OLID; CLERODANE DERIVATIVE; DELTA OPIATE RECEPTOR; DITERPENOID; INDIUM 111; KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; MU OPIATE RECEPTOR; PLANT EXTRACT; PLANT MEDICINAL PRODUCT; SALVIA EXTRACT; SALVIARIN; SALVIFARICIN; SALVIFARIN; SPLENDIDIN; SPLENOLIDE B; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMICAL MODIFICATION; CHINESE HAMSTER; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; SALVIA; SALVIA FARINACEA; SALVIA SPLENDENS; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANALGESICS, OPIOID; ANIMALS; CELL LINE, TUMOR; CHO CELLS; CRICETINAE; CRICETULUS; DITERPENES; DITERPENES, CLERODANE; HUMANS; PLANT EXTRACTS; RECEPTORS, OPIOID, KAPPA; SALVIA;

SALVIA; SALVIA DIVINORUM; SALVIA FARINACEA; SALVIA SPLENDENS;

EID: 34547525373     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200790138     Document Type: Article

References (28)

1. C. Epling, C. D. Játiva, Bot. Museum Leaflets Harvard Univ. 1962, 20, 75.
2. D. Y. W. Lee, Z. Ma, L.-Y. Liu-Chen, W. A. Carlezon Jr., B. M. Cohen, Bioorg. Med. Chem. 2005, 13, 5635
3. A. K. Bigham, T. A. Munro, M. A. Rizzacasa, R. M. Robins-Browne, J. Nat. Prod. 2003, 66, 1242
4. T. A. Munro, M. A. Rizzacasa, J. Nat. Prod. 2003, 66, 703
5. L. J. Valdés III, H. M. Chang, D. C. Visger, M. Koreeda, Org. Lett. 2001, 3, 3935.
6. M. Koreeda, L. Brown, L. J. Valdés III, Chem. Lett. 1990, 2015
7. L. J. Valdés III, W. M. Butler, G. M. Hatfield, A. G. Paul, M. Koreeda, J. Org. Chem. 1984, 49, 4716
8. A. Ortega, J. F. Blount, P. S. Manchand, J. Chem. Soc., Perkin Trans. 1 1982, 2505.
9. D. J. Siebert, J. Ethnopharmacol. 1994, 43, 53.
10. B. L. Roth, K. Baner, R. Westkaemper, D. J. Siebert, K. C. Rice, S. Steinberg, P. Emsberger, R. B. Rothman, Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11934.
11. D. J. Sheffler, B. L. Roth, Trends Pharmacol. Sci. 2003, 24, 107.
12. K. Tidgewell, W. W. Harding, A. Lozama, H. Cobb, K. Shah, P. Kannan, C. M. Dersch, D. Parrish, J. R. Deschamps, R. B. Rothman, T. E. Prisinzano, J. Nat. Prod. 2006, 69, 914
13. D. Y. W. Lee, V. V. R. Karnati, M. He, L.-Y. Liu-Chen, C. Beguin, W. A. Carlezon Jr., B. M. Cohen, Bioorg. Med. Chem. Lett. 2005, 15, 3744
14. C. Beguin, M. R. Richards, Y. Wang, Y. Chen, L.-Y. Liu-Chen, Z. Ma, D. Y. W. Lee, W. A. Carlezon Jr., B. M. Cohen, Bioorg. Med. Chem. Lett. 2005, 15, 2761.
15. W. W. Harding, K. Tidgewell, N. Byrd, H. Cobb, C. M. Dersch, E. R. Butelman, R. B. Rothman, T. E. Prisinzano, J. Med. Chem. 2005, 48, 4765.
16. G. Savona, M. P. Paternostro, F. Piozzi, J. R. Hanson, P. B. Hitchcock, S. A. Thomas, J. Chem. Soc., Perkin Trans. 1 1978, 643.
17. L. Eguren, J. Fayos, A. Perales, G. Savona, B. Rodriguez, Phytochemistry 1984, 23, 466.
18. J. S. Yadav, B. V. S. Reddy, K. Sadashiz, K. Harikishan, Tetrahedron Lett. 2002, 43, 2099
19. M. Bandini, M. Fagioli, A. Melloni, A. Umani-Ronchi, Adv. Synth. Catal. 2004, 346, 573.
20. C. L. Neilan, S. M. Husbands, S. Breeden, M. C. Ko, M. D. Aceto, J. W. Lewis, J. H. Woods, J. R. Traynor, Eur. J. Pharmacol. 2004, 499, 107
21. S. M. Husbands, C. Neilan, J. Broadbear, P. Grundt, S. Breedon, M. D. Aceto, J. H. Woods, J. W. Lewis, J. R. Traynor, Eur. J. Pharmacol. 2005, 509, 117.
22. F. Yan, P. D. Mosier, R. B. Westkaemper, J. Stewart, J. K. Zjawiony, T. A. Vortherms, D. J. Sheffler, B. L. Roth, Biochemistry 2005, 44, 8643.
23. B. E. Kane, M. J. Nieto, C. R. McCurdy, D. M. Ferguson, FEBS J. 2006, 273, 1966.
24. G. M. Sheldrick, SHELXS-97 and SHELXL-97, University of Göttingen, Germany, 1997.
25. G. Savona, M. P. Paternostro, P. Franco, J. Chem. Soc., Perkin Trans. 1 1979, 533.
26. K. O. Lee, H. Akil, J. H. Woods, J. R. Traynor, Eur. J. Pharmacol. 1999, 378, 323.
27. J. Zhu, L. Y. Luo, J. G. Li, C. Chen, L. Y. Liu-Chen, J. Pharmacol. Exp. Ther. 1997, 282, 676.
28. O. H. Lowry, N. G. Rosenberg, A. L. Farr, R. J. Randell, J. Biol. Chem. 1951, 139, 265.