Quantitative structure-activity relationship (QSAR) for neuroprotective activity of terpenoids

Life Sciences

Volumn 80, Issue 9, 2007, Pages 835-841

  Chang, Hyun Joo ^a   Kim, Hyun Jung ^a   Chun, Hyang Sook ^a  

^a Korea Food Research Institute   (South Korea)

Author keywords

In vitro simulated ischemia model; Neuroprotective activity; Quantitative structure activity relationship; SH SY5Y; Terpenoids; trans caryophyllene

Indexed keywords

BETA PINENE; BORNEOL; BORNYL ACETATE; CARYOPHYLLENE; CARYOPHYLLENE OXIDE; CINEOLE; DIZOCILPINE; METHYLEUGENOL; NEUROPROTECTIVE AGENT; PHYTOL; PINENE; TERPENOID; TERPINENE; TERPINEOL; UNCLASSIFIED DRUG; VERBENOL;

ARTICLE; BRAIN DAMAGE; BRAIN ISCHEMIA; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG CONFORMATION; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOPHILICITY; NEUROPROTECTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; ISCHEMIA; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; NEUROPROTECTIVE AGENTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

EID: 33846554894     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2006.11.009     Document Type: Article

References (38)

1. Ahmad A.S., Ansari M.A., Ahmad M., Saleem S., Yousuf S., Hoda M.N., and Islam F. Neuroprotection by crocetin in a hemi-parkinsonian rat model. Pharmacology, Biochemistry and Behavior 81 (2005) 805-813
2. Angioni A., Barr A., Cereti E., Barile D., Coïsson J.D., Arlorio M., Dessi S., Coroneo V., and Cabras P. Chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L. Journal of Agricultural and Food Chemistry 52 (2004) 3530-3535
3. Bouvier F., Rahier A., and Camara B. Biogenesis, molecular regulation and function of plant isoprenoids. Progress in Lipid Research 44 (2005) 357-429
4. Chun H.S., Chang H.-J., Choi E.H., Kim H.J., and Ku K.H. Molecular and absorption properties of 12 soy isoflavones and their structure-activity relationship with selected biological activities. Biotechnology Letters 27 (2005) 1105-1111
5. Defeudis F.V. Bilobalide and neuroprotection. Pharmacological Research 46 (2002) 565-568
6. 2 cannabinoid receptors. Journal of Medicinal Chemistry 43 (2000) 2300-2309
7. Giamakis A., Kretsi O., Chinou I., and Spyripoulos C.G. Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and β-pinene by in vitro cultures. Phytochemistry 58 (2001) 351-355
8. Griffin S.G., Wyllie S.G., Markham J.L., and Leach D.N. The role of structure and molecular properties of terpenoids in determining their antimicrobial activity. Flavour and Fragrance Journal 14 (1999) 322-332
9. Grodnitzky J.A., and Coats J.R. QSAR evaluation of monoterpenoids' insecticidal activity. Journal of Agricultural and Food Chemistry 50 (2002) 4576-4580
10. Han Y. Ginkgo terpene component has an anti-inflammatory effect on Candida albicans-caused arthritic inflammation. International Immunopharmacology 5 (2005) 1049-1056
11. Hermens J. Prediction of environmental toxicity based on structure-activity relationships using mechanistic information. Science of the Total Environment 171 (1995) 235-242
12. Hsiao G., Fong T.H., Tzu N.H., Lin K.H., Chou D.S., and Sheu J.R. A potent antioxidant, lycopene, affords neuroprotection against microglia activation and focal cerebral ischemia in rats. In Vivo 18 (2004) 351-356
13. İşcan G., Kírímer N., Kürkcüoǧlu M., Baser H.C., and Demírcí F. Antimicrobial screening of Mentha piperita essential oils. Journal of Agricultural and Food Chemistry 50 (2002) 3943-3946
14. Jackson S.J., Diemel L.T., Pryce G., and Baker D. Cannabinoids and neuroprotection in CNS inflammatory disease. Journal of Neurological Sciences 233 (2005) 21-25
15. Ka M.-H., Choi E.H., Chun H.S., and Lee K.-G. Antioxidative activity of volatile extracts isolated from Angelica tenuissimae roots, peppermint leaves, pine needles, and sweet flag leaves. Journal of Agricultural and Food Chemistry 53 (2005) 4124-4129
16. Keyser J.D., Sulter G., and Luiten P.G. Clinical trials with neuroprotective drugs in acute ischaemic stroke: are we doing the right thing?. Trends in Neuroscience 22 (1999) 535-540
17. Kim H.J., and Chun H.S. Structure-activity relationships of organosulfur compounds as inhibitors of cytochrome P450 1-mediated activation of benzo[a] pyrene in a human cell model. Biotechnology Letters 24 (2002) 2041-2046
18. Kim J.M., Lee J.-C., Chang N., Chun H.S., and Kim W.-K. S-Allyl-l-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase. Free Radical Research 40 (2006) 827-835
19. Koroshetz W.J., and Moskowitz M.A. Emerging treatments for stroke in humans. Trends in Pharmacological Science 17 (1996) 227-233
20. Kovatcheva A., Buchbauer G., Golbraikh A., and Wolschann P. QSAR modeling of α-campholenic derivatives with sandalwood odor. Journal of Chemical Information and Computer Sciences 43 (2003) 259-266
21. Lastres-Becker I., Molina-Holgado F., Ramos J.A., Mechoulam R., and Fernández-Ruiz J. Cannabinoids provide neuroprotection against 6-hydroxydopamine toxicity in vivo and in vitro: relevance to Parkinson's disease. Neurobiology of Disease 19 (2005) 96-107
22. Li D.-Q., Duan Y.-L., Bao Y.-M., Liu C.-P., Liu Y., and An L.-J. Neuroprotection of catalpol in transient global ischemia in gerbils. Neuroscience Research 50 (2004) 169-177
23. Lipton P. Ischemic cell death in brain neurons. Physiological Reviews 79 (1999) 1431-1568
24. Logani S., Chen M.C., Tran T., Le T., and Raffa R.B. Actions of Ginkgo Biloba related to potential utility for the treatment of conditions involving cerebral hypoxia. Life Sciences 67 (2000) 1389-1396
25. Mazzatorta P., Smiesko M., Piparo E.L., and Benfenati E. QSAR model for predicting pesticide aquatic toxicity. Journal of Chemical Information and Modeling 45 (2005) 1767-1774
26. Mhin B.J., Lee J.E., and Choi W. Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxin: chlorination pattern and molecular quadrupole moment. Journal of American Chemical Society 124 (2002) 144-148
27. Miglio G., Varsaldi F., Francioli E., Battaglia A., Canonico P.L., and Lombardi G. Cabergoline protects SH-SY5Y neuronal cells in an in vitro model of ischemia. European Journal of Pharmacology 489 (2004) 157-165
28. Murakami A., Tanaka T., Lee J.-Y., Surh Y.-J., Kim H.W., Kawabata K., Nakamura Y., Jiwajinda S., and Ohigashi H. Zerumbone, a sesquiterpene in subtropical ginger, suppresses skin tumor initiation and promotion stages in ICR mice. International Journal of Cancer 110 (2004) 481-490
29. 2L receptors in human neuroblastoma SH-SY5Y cells. Journal of Neurochemistry 66 (1996) 2390-2393
30. Osakada F., Kawato Y., Kume T., Katsuki H., Sugimoto H., and Akaike A. Serofendic acid, a sulfur-containing diterpenoid derived from fetal calf serum, attenuates reactive oxygen species-induced oxidative stress in cultured striatal neurons. Journal of Pharmacology and Experimental Therapeutics 311 (2004) 51-59
31. Pei Z., and Cheung R.T.F. Melatonin protects SH-SY5Y neuronal cells but not cultured astrocytes from ischemia due to oxygen and glucose deprivation. Journal of Pineal Research 34 (2003) 194-201
32. Pringle A.K., Iannotti F., Wilde G.J.C., Chad J.E., Seeley P.J., and Sundstrom L.E. Neuroprotection by both NMDA and non-NMDA receptor antagonists in in vitro ischemia. Brain Research 755 (1997) 36-46
33. Rawal A., Muddeshwar M., and Biswas S. Effect of Rubia cordifolia, Fagonia cretica linn, and Tinospora cordifolia on free radical generation and lipid peroxidation during oxygen-glucose deprivation in rat hippocampal slices. Biochemical and Biophysical Research Communications 324 (2004) 588-596
34. Selassie C.D., Mekapati S.B., and Verma R.P. QSAR: then and now. Current Topics in Medicinal Chemistry 2 (2002) 1357-1379
35. Siedle B., García-Pineres A.J., Murillo R., Schulte-Mönting J., Castro V., Rüngeler P., Klaas C.A., Da Costa F.B., Kisiel W., and Merfort I. Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NK-kB. Journal of Medicinal Chemistry 47 (2004) 6042-6054
36. Tsao R., and Coats J.R. Starting from nature to make better insecticides. Chemtech 25 (1995) 23-28
37. Verma R.P., and Hansch C. A comparison between two polarizability parameters in chemical-biological interactions. Bioorganic and Medicinal Chemistry 13 (2005) 2355-2372
38. Zhu W., Chen G., Hu L., Luo X., Gui C., Luo C., Puah C.M., Chen K., and Jiang H. QSAR analyses on ginkgolides and their analogues using CoMFA, CoMSIA, and HQSAR. Bioorganic and Medicinal Chemistry 13 (2005) 313-322