Ligustilide: A novel TRPA1 modulator

Pflugers Archiv European Journal of Physiology

Volumn 462, Issue 6, 2011, Pages 841-849

  Zhong, Jian ^a,b   Pollastro, Federica ^c   Prenen, Jean ^a   Zhu, Zhiming ^b   Appendino, Giovanni ^c   Nilius, Bernd ^a  

^a LABORATORY OF MOLECULAR AND CELLULAR SIGNALING   (Belgium)

^b THIRD MILITARY MEDICAL UNIVERSITY   (China)

^c UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

Chemosensation; Electrophiles; Mustard oil; Traditional Chinese medicine; TRP channels; TRPA1

Indexed keywords

ACROLEIN; ALLYL ISOTHIOCYANATE; CYSTEINE; DEHYDROLIGUSTILIDE; LIGUSTILIDE; TRANSIENT RECEPTOR POTENTIAL CHANNEL A1; TRANSIENT RECEPTOR POTENTIAL CHANNEL M8; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

AGING; ALKYLATION; ANIMAL CELL; AROMATIZATION; ARTICLE; CONTROLLED STUDY; DESENSITIZATION; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ELECTROPHILICITY; GENE; GENE ACTIVATION; GENE INTERACTION; GENE MUTATION; MOUSE; NONHUMAN; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN MOTIF; TRPA1 GENE;

4-BUTYROLACTONE; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; MEDICINE, TRADITIONAL; MICE; MOLECULAR STRUCTURE; MUSTARD PLANT; PATCH-CLAMP TECHNIQUES; PLANT OILS; TRANSIENT RECEPTOR POTENTIAL CHANNELS;

EID: 83555174763     PISSN: 00316768     EISSN: 14322013     Source Type: Journal    
DOI: 10.1007/s00424-011-1021-7     Document Type: Article

References (27)

1. G Appendino N Daddario A Minassim L De Petrocellis V Di Marzo 2005 The taming of capsaicin: reversal of the vanilloid activity of N-acylvanillamides by aromatic iodination J Med Chem 48 4663 4669 16000002 10.1021/jm050139q 1:CAS:528:DC%2BD2MXkvFSmtbY%3D (Pubitemid 40993425)
2. C Avonto O Taglialatela-Scafati F Pollastro A Minassi V Di Marzo L De Petrocellis G Appendino 2011 An NMR spectroscopic method to identify and classify thiol-trapping agents: revival of Michael acceptors for drug discovery? Angew Chem Int Ed Engl 50 467 471 21132828 10.1002/anie.201005959 1:CAS:528:DC%2BC3MXitlGiuw%3D%3D
3. JJ Beck FR Stermitz 1995 Addition of methyl thioglycolate and benzylamine to (Z)-ligustilide, a bioactive unsaturated lactone constituent of several herbal medicines. An improves synthesis of (Z)-ligustilide J Nat Prod 58 1047 1055 7561898 10.1021/np50121a009 1:CAS:528:DyaK2MXnslemsLs%3D
4. SS Chan TY Cheng G Lin 2007 Relaxation effects of ligustilide and senkyunolide A, two main constituents of Ligusticum chuanxiong, in rat isolated aorta J Ethnopharmacol 111 677 680 17222996 10.1016/j.jep.2006.12.018 1:CAS:528:DC%2BD2sXkslCgtL8%3D (Pubitemid 46617091)
5. BM Dietz D Liu GK Hagos P Yao A Schinkovitz SM Pro S Deng NR Farnsworth GF Pauli RB van Breemen JL Bolton 2008 Angelica sinensis and its alkylphthalides induce the detoxification enzyme NAD(P)H: quinone oxidoreductase 1 by alkylating Keap1 Chem Res Toxicol 21 1939 1948 18808158 10.1021/tx8001274 1:CAS:528:DC%2BD1cXhtFChsbbI
6. J Du Y Yu Y Ke C Wang L Zhu ZM Qian 2007 Ligustilide attenuates pain behavior induced by acetic acid or formalin J Ethnopharmacol 112 211 214 17350195 10.1016/j.jep.2007.02.007 1:CAS:528:DC%2BD2sXlt1amtbY%3D (Pubitemid 46711224)
7. MJM Gijbels JJ Scheffer AB Svendsen 1982 Phthalides in the essential oil from roots of Levisticum officinale Planta Med 44 207 211 17402120 10.1055/s-2007-971448 1:CAS:528:DyaL38XksFamsLg%3D (Pubitemid 12093663)
8. J Guo J Duan E Shang Y Tang D Qian 2009 Determination of ligustilide in rat brain after nasal administration of essential oil from Rhizoma chuanxiong Fitoterapia 80 168 172 19535021 10.1016/j.fitote.2009.01.003 1:CAS:528:DC%2BD1MXktFShtL0%3D
9. J Guo E Shang J Duang Y Tang D Qian 2011 Determination of ligustilide in the brain of freely moving rats using microdialysis coupled with ultra performance liquid chromatography/mass spectrometry Fitoterapia 82 441 445 21156197 10.1016/j.fitote.2010.12.002 1:CAS:528:DC%2BC3MXhvFWju7c%3D
10. A Hinman H-H Chuang DM Bautista D Julius 2007 TRP channel activation by reversible covalent modification Proc Natl Acad Sci USA 103 19564 19568 10.1073/pnas.0609598103 (Pubitemid 46026070)
11. Y Karashima N Damann J Prenen K Talavera A Segal T Voets B Nilius 2007 Bimodal action of menthol on the transient receptor potential channel TRPA1 J Neurosci 27 9874 9884 17855602 10.1523/JNEUROSCI.2221-07.2007 1:CAS:528:DC%2BD2sXhtVyksbvF (Pubitemid 47403994)
12. XR Li YZ Liang FQ Guo 2006 Analysis of volatile oil in Rhizoma ligustici chuanxiong-radix paeoniae rubra by gas chromatography-mass spectrometry and chemometric resolution Acta Pharmacol Sin 27 491 498 16539851 10.1111/j.1745-7254.2006.00305.x 1:CAS:528:DC%2BD28Xjs12jtrc%3D
13. Q Lu TQ Qiu H Yang 2006 Ligustilide inhibits vascular smooth muscle cells proliferation Eur J Pharmacol 542 136 140 16806164 10.1016/j.ejphar.2006.04.023 1:CAS:528:DC%2BD28XntlWmsLo%3D (Pubitemid 44066356)
14. LJ Macpherson AE Dubin MJ Evans F Marr PG Schultz BF Cravatt A Patapoutian 2007 Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines Nature 445 541 545 17237762 10.1038/nature05544 1:CAS:528:DC%2BD2sXhtFWhur0%3D (Pubitemid 46197634)
15. QB Mei JY Tao B Cui 1991 Advances in the pharmacological studies of radix Angelica sinensis (oliv) diels (Chinese danggui) Chin Med J (Engl) 104 776 781 1:STN:280:DyaK38%2Fjs1Ojtg%3D%3D
16. W Meyerhof 2005 Elucidation of mammalian bitter taste Rev Physiol Biochem Pharmacol 154 37 72 16032395 10.1007/s10254-005-0041-0 1:CAS:528: DC%2BD28XivFCjsrY%3D
17. B Nilius J Prenen G Owsianik 2011 Irritating channels: the case of TRPA1 J Physiol 589 1543 1549 21078588 10.1113/jphysiol.2010.200717 1:CAS:528:DC%2BC3MXlt1Shsr0%3D
18. C Peng X Xie L Wang L Guo T Hu 2009 Pharmacodynamic action and mechanism of volatile oil from Rhizoma Ligustici chaunxiong Hort. on treating headache Phytomedicine 16 23 34 10.1016/j.phymed.2008.10.010
19. MH Potashman ME Dugganm 2009 Covalent modifiers: an orthogonal approach to drug discovery J Med Chem 52 1231 1246 19203292 10.1021/jm8008597 1:CAS:528:DC%2BD1MXhs1Sltbw%3D
20. A Schinkovitz SM Pro M Main SN Chen BU Jaki DC Lankin GF Pauli 2008 Dynamic nature of the ligustilide complex J Nat Prod 71 1604 1611 18781813 10.1021/np800137n 1:CAS:528:DC%2BD1cXhtV2lu7rP
21. M Shao K Qu K Liu Y Zhang L Zhang Z Lian T Chen J Liu A Wu Y Tang H Zhu 2011 Effects of ligustilide on lipopolysaccharide-induced endotoxic shock in rabbits Planta Med 77 809 816 21104607 10.1055/s-0030-1250573 1:CAS:528:DC%2BC3MXosFKisbs%3D
22. GM Story AM Peier AJ Reeve SR Eid J Mosbacher TR Hricik TJ Earley AC Hergarden DA Andersson SW Hwang P McIntyre T Jegla S Bevan A Patapoutian 2003 ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures Cell 112 819 829 12654248 10.1016/S0092-8674(03)00158-2 1:CAS:528:DC%2BD3sXivVWjsbk%3D (Pubitemid 36378884)
23. J Tang Y Zhang TG Hartman RT Rosen CT Ho 1990 Free and glycosidically bond volatile compounds in fresh celery (Apium graveolens L.) J Agric Food Chem 38 1937 1940 10.1021/jf00100a013 1:CAS:528:DyaK3cXlsFWjtb4%3D
24. J Wang JR Du Y Wang X Kuang CY Wang 2010 Z-Ligustilide attenuates lipopolysaccharide-induced proinflammatory response via inhibiting NF-kappab pathway in primary rat microglia Acta Pharmacol Sin 31 791 797 20581853 10.1038/aps.2010.71
25. Wu XM, Qian ZM, Zhu L, Du F, Yung WH, Gong Q, Ke Y (2011) Neuroprotective effect of ligustilide against ischemia-reperfusion injury via up-regulation of erythropoietin and down-regulation of RTP801. Br J Pharmacol, in press
26. R Yan NL Ko S-L Li YK Tam G Lin 2008 Pharmacokinetics and metabolism of ligustilide, a major bioactive component in Rhizoma chuanxiong, in the rat Drug Metab Dispos 36 400 408 18039808 10.1124/dmd.107.017707 1:CAS:528: DC%2BD1cXht1yku7s%3D (Pubitemid 351185754)
27. L Zhang JR Du J Wang DK Yu YS Chen Y He CY Wang 2009 Z-Ligustilide extracted from radix Angelica sinensis decreased platelet aggregation induced by adp ex vivo and arterio-venous shunt thrombosis in vivo in rats Yakugaku Zasshi 129 855 859 19571521 10.1248/yakushi.129.855 1:CAS:528:DC%2BD1MXhtFSntb%2FJ