Characterization of natural aryl hydrocarbon receptor agonists from cassia seed and rosemary

Molecules

Volumn 19, Issue 4, 2014, Pages 4956-4966

  Amakura, Yoshiaki ^a   Yoshimura, Morio ^a   Takaoka, Masashi ^a   Toda, Haruka ^a   Tsutsumi, Tomoaki ^b   Matsuda, Rieko ^b   Teshima, Reiko ^b   Nakamura, Masafumi ^c   Handa, Hiroshi ^c   Yoshida, Takashi ^a  

^a MATSUYAMA UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^c Hiyoshi Corporation   (Japan)

Author keywords

Aryl hydrocarbon receptor; Cassia seed; Health food; Reporter gene assay; Rosemary

Indexed keywords

6-METHOXY-4',5-DIHYDROXYFLAVONE-7-O-GLUCOSIDE; ANTHRAQUINONE DERIVATIVE; AROMATIC HYDROCARBON RECEPTOR; CIRSIMARITIN; FLAVONE DERIVATIVE; FLAVONOID; GLUCOSIDE; IMMUNOLOGIC FACTOR; LUCIFERASE; LUTEOLIN; NEPITRIN; PLANT EXTRACT;

AGONISTS; ANIMAL; CASSIA; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; GENE EXPRESSION; GENETICS; HUMAN; ISOLATION AND PURIFICATION; LIVER CELL; METABOLISM; MOUSE; PLANT LEAF; PLANT SEED; REPORTER GENE; RHODODENDRON; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

ANIMALS; ANTHRAQUINONES; CASSIA; CELL LINE, TUMOR; FLAVONES; FLAVONOIDS; GENE EXPRESSION; GENES, REPORTER; GLUCOSIDES; HEPATOCYTES; HUMANS; IMMUNOLOGIC FACTORS; LEDUM; LUCIFERASES; LUTEOLIN; MICE; PLANT EXTRACTS; PLANT LEAVES; RECEPTORS, ARYL HYDROCARBON; SEEDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899504527     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19044956     Document Type: Article

References (25)

1. Machala, M.; Vondrácek, J.; Bláha, L.; Ciganek, M.; Neca, J. Aryl hydrocarbon receptormediated activity of mutagenic polycyclic aromatic hydrocarbons determined using in vitro reporter gene assay. Mutat. Res. 2001, 31, 347-364.
2. Fujii-Kuriyama, Y.; Mimura, J. Molecular mechanisms of AhR functions in the regulation of cytochrome P450 genes. Biochem. Biophys. Res. Commun. 2005, 338, 311-317.
3. Nebert, D.W.; Dalton, T.P. The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis. Nat. Rev. Cancer. 2006, 6, 947-960.
4. Amakura, Y.; Tsutsumi, T.; Sasaki, K.; Nakamura, M.; Yoshida, T.; Maitani, T. Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay. Phytochemistry 2008, 69, 3117-3130.
5. Ashida, H.; Nishiumi, S.; Fukuda, I. An update on the dietary ligands of the AhR. Expert Opin. Drug Metab. Toxicol. 2008, 4, 1429-1447.
6. Wang, H.K.; Yeh, C.H.; Iwamoto, T.; Satsu, H.; Shimizu, M.; Totsuka, M. Dietary flavonoid naringenin induces regulatory T cells via an aryl hydrocarbon receptor mediated pathway. J. Agric. Food Chem. 2012, 60, 2171-2178.
7. Tan, Z.; Chang, X.; Puga, A.; Xia, Y. Activation of mitogen-activated protein kinase (MAPKs) by aromatic hydrocarbons: role in the regulation of aryl hydrocarbon receptor (AHR) function. Biochem. Pharmacol. 2002, 64, 771-780.
8. Kawajiri, K.; Kobayashi, Y.; Ohtake, F.; Ikuta, T.; Matsushima, Y.; Mimura, J.; Pettersson, S.; Pollenz, R.S.; Sakaki, T.; Hirokawa, T.; et al. Aryl hydrocarbon receptor suppresses intestinal carcinogenesis in ApcMin/+ mice with natural ligands. Proc. Natl. Acad. Sci. USA 2009, 106, 13481-13486.
9. Kimura, A.; Naka, T.; Nohara, K.; Fujii-Kuriyama, Y.; Kishimoto, T. Aryl hydrocarbon receptor regulates Stat1 activation and participates in the development of Th17 cells. Proc. Natl. Acad. Sci. USA 2008, 105, 9721-9726.
10. Quintana, F.J.; Basso, A.S.; Iglesias, A.H.; Korn, T.; Farez, M.F.; Bettelli, E.; Caccamo, M.; Oukka, M.; Weiner, H.L. Control of Treg and TH17 cell differentiation by the aryl hydrocarbon receptor. Nature 2008, 453, 65-71.
11. Veldhoen, M.; Hirota, K.; Westendorf, A.M.; Buer, J.; Dumoutier, L.; Renauld, J.; Stockinger, B. The aryl hydrocarbon receptor links TH17-cell-mediated autoimmunity to environmental toxins. Nature 2008, 453, 106-110.
12. Kiss, E.A.; Vonarbourg, C.; Kopfmann, S.; Hobeika, E.; Finke, D.; Esser, C.; Diefenbach, A. Natural aryl hydrocarbon receptor ligands control organogenesis of intestinal lymphoid follicles. Science 2011, 334, 1561-1565.
13. Hu, W.; Zhao, J.; Pei, G. Activation of aryl hydrocarbon receptor by tranilast, an anti-allergy drug, promotes miR-302 expression and reprogramming. J. Biol. Chem. 2013, 288, 22972-22984.
14. Tsutsumi, T.; Amakura, Y.; Nakamura, M.; Brown, D.J.; Clark, G.C.; Sasaki, K.; Toyoda, M.; Maitani, T. Validation of the CALUX bioassay for the screening of PCDD/Fs and dioxin-like PCBs in retail fish. Analyst 2003, 128, 486-492.
15. Overmeire, I.V.; Clark, G.C.; Brown, D.J.; Chu, M.D.; Cooke, W.M.; Denison, M.S.; Baeyens, W.; Srebrnik, S.; Goeyens, L. Analysis of Ah receptor pathway activation by brominated flame retardants. Environ. Sci. Policy 2001, 4, 345-357.
16. Han, D.; Nagy, S.R.; Denison, M.S. Comparison of recombinant cell bioassays for the detection of Ah receptor agonists. BioFactors 2004, 20, 11-22.
17. Moghaddam, G.; Ebrahimi, S.A.; Rahbar-Roshandel, N.; Foroumadi, A. Antiproliferative activity of flavonoids: Influence of the sequential methoxylation state of the flavonoid structure. Phytother. Res. 2012, 26, 1023-1028.
18. Agarwal, O.P. The anti-inflammatory action of nepitrin, a flavonoid. Agents Actions 1982, 12, 298-302.
19. Nugroho, A.; Kim, M.H.; Choi, J.; Beak, N.I.; Park, H.J. In vivo sedative and gastroprotective activities of Salvia plebeian extract and its composition of polyphenols. Arch. Pharm. Res. 2012, 35, 1403-1411.
20. Li, X.C.; Dunbar, D.C.; Elsohly, H.N.; Jacob, M.R.; Nimrod, A.C.; Walker, L.A.; Clark, A.M. A new naphthopyrone derivative from Cassia quinquangulata and structural revision of quinquangulin and its glycosides. J. Nat. Prod. 2001, 64, 1153-1156.
21. Yun-Choi, H.S.; Kim, J.H. Potential inhibitors of platelet aggregation from plant sources, V. Anthraquinones from seeds of Cassia obtusifolia and related compounds. J. Nat. Prod. 1990, 53, 630-633.
22. Begum, S.; Wahab, A.; Siddiqui, B.S.; Qamar, F. Nematicidal constituents of the aerial parts of Lantana camara. J. Nat. Prod. 2000, 63, 765-767.
23. Ly, T.N.; Shimoyamada, M.; Yamauchi, R. Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth leaves and their antioxidative activity. J. Agric. Food Chem. 2006, 54, 3786-3793.
24. Wang, M.; Li, J.; Rangarajan, M.; Shao, Y.; LaVoie, E.; Huang, T.C.; Ho, C.T. Antioxidative phenolic compounds from sage (Salvia officinalis). J. Agric. Food Chem. 1998, 46, 4869-4873.
25. Perez-Fons, L.; Garzón, M.T.; Micol, V. Relationship between the antioxidant capacity and effect of rosemary (Rosmarinus officinalis L.) polyphenols on membrane phospholipid order. J. Agric. Food Chem. 2010, 58, 161-171.