Phytochemicals from Ruta graveolens activate TAS2R bitter taste receptors and TRP channels involved in gustation and nociception

Molecules

Volumn 20, Issue 10, 2015, Pages 18907-18922

  Mancuso, Giuseppe ^a   Borgonovo, Gigliola ^a   Scaglioni, Leonardo ^a   Bassoli, Angela ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Bitter taste; Chemesthesis; Ruta graveolens; TAS2Rs receptors; TRP channels

Indexed keywords

ESSENTIAL OIL; G PROTEIN COUPLED RECEPTOR; PLANT EXTRACT; TASTE RECEPTORS, TYPE 2; TRANSIENT RECEPTOR POTENTIAL CHANNEL; VEGETABLE OIL;

AGONISTS; CALCIUM SIGNALING; CHEMISTRY; DOSE RESPONSE; HEK293 CELL LINE; HUMAN; IC50; ISOLATION AND PURIFICATION; NOCICEPTION; RUTA; STRUCTURE ACTIVITY RELATION; TASTE;

CALCIUM SIGNALING; DOSE-RESPONSE RELATIONSHIP, DRUG; HEK293 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; NOCICEPTION; OILS, VOLATILE; PLANT EXTRACTS; PLANT OILS; RECEPTORS, G-PROTEIN-COUPLED; RUTA; STRUCTURE-ACTIVITY RELATIONSHIP; TASTE; TRANSIENT RECEPTOR POTENTIAL CHANNELS;

EID: 84947601097     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules201018907     Document Type: Article

References (42)

1. Appendino, G.; Minassi, A.; Pagani, A.; Ech-Chahad, A. The role of natural products in the ligand deorphanization of TRP channels. Curr. Pharm. Des. 2008, 14, 2-17.
2. Roland, W.S.U.; van Buren, L.; Gruppen, H.; Driesse, M.; Gouka, R.J.; Smit, G.; Vincken, J.P. Bitter Taste receptor activation by flavonoids and isoflavonoids: modelled structural requirements for activation of hTAS2R14 and hTAS2R39. J. Agric. Food Chem. 2013, 61, 10454-10466.
3. Behrens, M.; Meyerhof, W.; Hellfritsch, C.; Hofmann, T. Sweet and umami taste: Natural products, their chemosensory targets, and beyond. Angew. Chem. Int. Ed. 2011, 50, 2220-2242.
4. Meyerhof, W.; Batram, C.; Kuhn, C.; Brockhoff, A.; Chudoba, E.; Bufe, B.; Appendino, G.; Behrens, M. The molecular receptive ranges of human TAS2R bitter taste receptors. Chem. Senses 2010, 35, 157-170.
5. Brockhoff, A.; Behrens, M.; Roudnitzky, N.; Appendino, G.; Avonto, C.; Meyerhof, W. Receptor agonism and antagonism of dietary bitter compounds. J. Neurosci. 2011, 31, 14775-14782.
6. Soares, S.; Kohl, S.; Thalmann, S.; Mateus, N.; Meyerhof, W.; de Freitas, V. Different phenolic compounds activate distinct human bitter taste receptors. J. Agric. Food Chem. 2013, 61, 1525-1533.
7. Clapham, D.E. TRP channels as cellular sensors. Nature 2003, 426, 517-524.
8. Viana, F. Chemosensory properties of the trigeminal system. ACS Chem. Neurosci. 2011, 2, 38-50.
9. Green, B.G. Chemesthesis and the chemical senses as components of a "chemofensor complex". Chem. Senses 2012, 37, 201-206.
10. Benigni, R.; Capra C.; Cattorini, P.E. Piante Medicinali, Chimica, Farmacologia E Terapia; Inverni & Della: Milano, Italy, 1964; pp. 1372-1385.
11. Hale, A.L.; Meepagala, K.M.; Oliva, A.; Aliotta, G.; Duke, S.O. Phytotoxins from the leaves of Ruta graveolens. J. Agric. Food Chem. 2004, 52, 3345-3349.
12. Haddouchi, F.; Chaouche T. M.; Zaouali Y.; Ksouri R.; Attou, A.; Benmansour, A. Chemical composition and antimicrobial activity of the essential oils from four Ruta species growing in Algeria. Food Chem. 2013, 141, 253-258.
13. Ghirardini, M.P.; Carli, M.; del Vecchio, N.; Rovati, A.; Cova, O.; Valigi, F.; Agnetti, G.; Macconi, M.; Adamo, D.; Traina, M.; et al. The importance of a taste. A comparative study on wild food plant consumption in twenty-one local communities in Italy. J. Ethnobiol. Ethnomed. 2007, 3, doi:10.1186/1746-4269-3-22.
14. Sallal, A.J.; Alkofahi, A. Inibithion of the hemolytic activities of snake and scorpion venoms in vitro with plant extracts. Biomed. Lett. 1996, 53, 211-215.
15. Kataki, M.S.; Kakoti, B.B.; Bhuyan, B.; Rajkumari, A.; Rajak, P. Garden rue inhibits the arachidonic acid pathway, scavenges free radicals, and elevates FRAP: Role in inflammation. Chin. J. Nat. Med. 2014, 12, 172-179.
16. Fadlalla, K.; Watson, A.; Yehualaeshet, T.; Turner, T.; Samuel, T. Ruta graveolens extract induces dna damage pathways and blocks akt activation to inhibit cancer cell proliferation and survival. Anticancer Res. 2011, 31, 233-241.
17. Gasparro, F.P. Extracorporeal Photochemotherapy: Clinical Aspects and the Molecular Basis for Efficacy; RG Landes Company, CRC Press: Georgetown, TX, USA, 1994.
18. Browne, F.; Turner, D.; Goulden, V. Psoralen and ultraviolet A in the treatment of granuloma annulare. Photodermatol. Photo 2011, 27, 81-84.
19. Zhang, Y.; Zhang, H.; Yao, X-G.; Shen, H.; Chen, J.; Li, C.; Zheng, M.; Ye, J.; Hu, L.; Shen, X.; Jiang, H. (+)-Rutamarin as a dual inducer of both GLUT4 traslocation and expression efficiently ameliorates glucose homeostasis in insulin resistant mice. PLoS ONE 2012, 7, e31811.
20. Ratheesh, M.; Sindhu, G.; Helen, A. Anti-inflammatory effect of quinoline alkaloid skimmianine isolated from Ruta graveolens L. Inflamm. Res. 2013, 62, 367-376.
21. Park, S.-H.; Sim, Y.-B.; Kim, S.-M.; Lee, J.-K.; Lim, S.-M.; Kim, J.-K.; Suh, H.-W. Antinociception effect and mechanism of Ruta graveolens L. In mice. J. Korean Soc. Appl. Biol. Chem. 2010, 53, 593-597.
22. Oliva, A.; Lahoz, E.; Contillo, R.; Aliotta, G. Fungistatic activity of Ruta graveolens extracts and its allelochemicals. J. Chem. Ecol. 1999, 25, 519-526.
23. Oliva, A.; Meepagala, K.M.; Wedge, D.E.; Harries, D.; Hale, A.L.; Aliotta, G.; Duke, S.O. Natural fungicides from Ruta graveolens L. Leaves, including a new quinolone alkaloid. J. Agric. Food Chem. 2003, 51, 890-896.
24. Astelbauer, F.; Gruber, M.; Brem, B.; Greger, H.; Obwaller, A.; Wernsdorfer, G.; Congpuong, K.; Wersdorfer, W.H.; Walochnik, J. Activity of selected phytochemicals against Plasmodium falciparum. Acta Trop. 2012, 123, 96-100.
25. Mann, R.S.; Tiwari, S.; Smoot, J.M.; Rouseff, R.L.; Stelinski, L.L. Repellency and toxicity of plant-based essential oils and their constituents against Diaphorina citri Kuwayama (Hemiptera: Psyllidae). J. Appl. Entomol. 2012, 136, 87-96.
26. Innocent, E.; Gikonyo N.K.; Nkunya, M.H. Repellency property of long chain aliphatic methyl ketones against Anopheles gambiae s.s. Tanzan J. Health Res. 2008, 10, 50-54.
27. Bassoli, A.; Borgonovo, G.; Busnelli, G. Alkaloids and the bitter taste. In Modern Alkaloids, Structure, Isolation, Synthesis and Biology; Fattorusso, E., Taglialatela Scafati, O., Fattorusso, E., Taglialatela-Scafati, O., Eds.; Wiley VCH: Weinheim, Germany, 2007; pp. 53-70.
28. Born, S.; Levit, A.; Niv, M.Y.; Meyerhof, W.; Behrens, M. The human bitter taste receptor TAS2R10 is tailored to accommodate numerous diverse ligands. J. Neurosci. 2013, 33, 201-213.
29. Bassoli, A.; Borgonovo, G.; Caimi, S.; Scaglioni, L.; Morini, G.; Schiano Moriello A.; di Marzo, V.; de Petrocellis, L. Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens. J. Biorg. Med. Chem. 2009, 17, 1636-1639.
30. Zhang, L.; Barrit, G.J. Evidence that TRPM8 is an androgen dependent Ca2+ channel required for the survival of the prostate cancer cells. Cancer Res. 2004, 64, 8365-8373.
31. Zhang, L.; Barrit, G.J. TRPM8 is prostate cancer cells: A potential diagnostic and prognostic marker with a secretory function? Endocr. Relat. 2006, 13, 27-38.
32. Chianese, G.; Fattorusso, E.; Putra, M.Y.; Calcinai, B.; Bavestrello, G.; Schiano Moriello A.; de Petrocellis, L.; di Marzo V.; Taglialatela Scafati, O. Leuccettamols, bifunctionalised marine sphingoids, act as modulators of TRPA1 and TRPM8 channels. Mar. Drugs 2012, 10, 2435-2447.
33. Terada, Y.; Horie, S.; Takayama H.; Uchida, K.; Tominaga, M.; Watanabe, T. Activation and Inhibition of Thermosensitive TRP Channels by Voacangine, an Alkaloid Present in Voacanga africana, an African Tree. J. Nat. Prod. 2014, 77, 285-297.
34. Baraldi, P.G.; Preti, D.; Materazzi, S.; Geppetti, P. Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents. J. Med. Chem. 2010, 53, 5085-5107.
35. Knowlton, W.M.; Bifolk-Fisher, A.; Bautista, D.M.; McKemy, D.D. TRPM8 but not TRPA1 is required for neural and behavioural responses to acute noxious cold temperature and cold-mimetic in vivo. Pain 2010, 150, 340-350.
36. Brignell, J.L.; Chapman, V.; Kendall, D.A. Comparison of icilin-and cold-evoked responses of spinal neurones, and their modulation of mechanical activity, in a model of neurophatic pain. Brain Res. 2008, 1215, 87-96.
37. Zhang, Y.N.; Zhang, S.L.; Ma, L.; Zhang, Y.; Shen, X.; Wang, W.; Hu, L.H. Total synthesis of (+)-rutamarin. Adv. Synt. Catal. 2008, 350, 2373-2379.
38. Muller, M.; Byres, M.; Jaspars, M.; Kumarasamy, Y.; Middleton, M.; Nahar, L.; Shoeb, M.; Sarker, S.D. 2D NMR Spectroscopic Analyses of Archangelicin from the Seed of Angelica archangelica. Acta Pharm. 2004, 54, 277-285.
39. Liu, R.; Feng, L.; Sun, A.; Kong, L. Preparative isolation and purification of coumarins from Cnidium monnieri (L.) Cusson by high-speed counter-current chromatography. J. Chromatog. A 2004, 1055, 71-76.
40. Wu, T.S.; Shi, L.S.; Wang, J.J.; Iou, S.C.; Chang, H.C.; Chen, Y.P.; Kuo, Y.H.; Chang, Y.L.; Teng, C.M. Cytotoxic and Antiplatelet Aggregation Principles of Ruta graveolens. J. Chin. Soc. 2003, 50, 171-178.
41. Phadke, P.C.; Kelkar, S.L.; Wadia, M.S. A general synthesis of bis[coumarinyl]ethers: Synthesis of daphnoretin methyl ether. Synthesis 1986, 5, 413-415.
42. Bassoli, A.; Borgonovo, G.; Caremoli, F.; Mancuso, G. The taste of D-and L-amino acids: In vitro binding assays with cloned human bitter (TAS2Rs) and sweet (TAS1R2/TAS1R3) receptors. Food Chem. 2014, 150, 27-33.