Antiviral activity of polymethoxylated flavones from " guangchenpi", the edible and medicinal pericarps of citrus reticulata 'chachi'

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 10, 2014, Pages 2182-2189

  Xu, Jiao Jiao ^a   Wu, Xia ^a   Li, Man Mei ^a   Li, Guo Qiang ^a   Yang, Yi Ting ^b   Luo, Hu Jie ^b   Huang, Wei Huang ^a   Chung, Hau Yin ^c   Ye, Wen Cai ^a   Wang, Guo Cai ^a   Li, Yao Lan ^a  

^a JINAN UNIVERSITY   (China)

^b Infinitus China Company Ltd   (China)

^c CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

antiviral activity; Citrus reticulata 'Chachi'; polymethoxylated flavones; RSV; tangeretin

Indexed keywords

BIOASSAY; EFFLUENT TREATMENT; POLYMERASE CHAIN REACTION; SUPERCRITICAL FLUIDS; VIRUSES; ASSAYS;

ANTIVIRAL ACTIVITIES; CITRUS RETICULATA 'CHACHI; POLYMETHOXYLATED FLAVONE; RSV; TANGERETIN;

FLAVONOIDS;

ANTIVIRUS AGENT; FLAVONE DERIVATIVE; NOBILETIN; P PROTEIN, HUMAN RESPIRATORY SYNCYTIAL VIRUS; PLANT EXTRACT; TANGERETIN; VIRUS PROTEIN;

ARTICLE; CELL LINE; CHEMISTRY; CITRUS; DOSE RESPONSE; DRUG EFFECT; DRUG SCREENING; GENETICS; HUMAN; ISOLATION AND PURIFICATION; MEDICINAL PLANT; METABOLISM; METHODOLOGY; PATHOGENICITY; RESPIRATORY SYNCYTIAL PNEUMOVIRUS; VIROLOGY; VIRUS ATTACHMENT;

ANTIVIRAL AGENTS; CELL LINE; CITRUS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; FLAVONES; HUMANS; PLANT EXTRACTS; PLANTS, MEDICINAL; RESPIRATORY SYNCYTIAL VIRUSES; VIRAL STRUCTURAL PROTEINS; VIRUS ATTACHMENT;

CITRUS RETICULATA; RESPIRATORY SYNCYTIAL VIRUS; RICE STRIPE VIRUS;

EID: 84896368933     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf404310y     Document Type: Article

References (35)

1. Zheng, G. D.; Jiang, L.; Yang, D. P.; Zhou, F.; Yang, X.; Lin, L. W. Determination of five flavonoids in Pericarpium Citri Reticulate collected from different regions by HPLC Chin. Tradit. Herb. Drugs 2010, 41, 652-655
2. Xia, J.; Kotani, A.; Hakamata, H.; Kusu, F. Determination of hesperidin in Pericarpium Citri Reticulatae by semi-micro HPLC with electrochemical detection J. Pharm. Biomed. Anal. 2006, 41, 1401-1405
3. Xu, G. H.; Chen, J. C.; Liu, D. H.; Zhang, Y. H.; Jiang, P. P.; Ye, X. Q. Minerals, phenolic compounds, and antioxidant capacity of Citrus peel extract by hot water J. Food Sci. 2008, 73 (1) C11-C18
4. Tripoli, E.; Guardia, M. L.; Giammanco, S.; Majo, D. D.; Giammanco, M. Citrus flavonoids: Molecular structure, biological activity and nutritional properties: A review Food Chem. 2007, 104, 466-479
5. Barreca, D.; Bisignano, C.; Ginestra, G.; Bisignano, G.; Bellocco, E.; Leuzzi, U.; Gattuso, G. Polymethoxylated, C-and O -glycosyl flavonoids in tangelo juice and their influence on antioxidant properties Food Chem. 2013, 141, 1481-1488
6. Chen, J.; Montanari, A. M.; Widmer, W. W. Two new polymethoxylated flavones, a class of compounds with potential anticancer activity, isolated from cold pressed dancy tangerine peel oil solids J. Agric. Food Chem. 1997, 45, 364-368
7. Attaway, J. A. Citrus juice flavonoids with anticarcinogenic and antitumor properties ACS Symp. Ser. 1994, 546, 240-248
8. Ho, C.; Li, S.; Pan, M.; Lo, C. Polymethoxyflavonoids and hydroxylated polymethoxyflavonoids in Citrus peels and their potential health beneficial properties Pacifichem 2010, AGRO-253
9. Liu, L.; Xu, X. Y.; Cheng, D.; Yao, X. L.; Pan, S. Y. Structure-activity relationship of Citrus polymethoxylated flavones and their inhibitory effects on Aspergillus niger J. Agric. Food Chem. 2012, 60, 4336-4341
10. Lam, I. K.; Alex, D.; Wang, Y. H.; Liu, P.; Liu, A. L.; Du, G. H.; Yuen, L.; Simon, M. In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: Identifying sinensetin as a novel antiangiogenesis agent Mol. Nutr. Food Res. 2012, 56, 945-956
11. Johann, S.; Lopes, O. V.; Pizzolatti, M. G.; Schripsema, J.; Braz-Filho, R.; Branco, A.; Smania, A. J. Antimicrobial activity of wax and hexane extracts from Citrus spp. peels Mem. Inst. Oswaldo Cruz 2007, 102, 681-685
12. Li, S. M.; Lo, C. Y.; Dushenkov, S.; Ho, C. T. Polymethoxyflavones: Chemistry, biological activity, and occurrence in orange peel ACS Symp. Ser. 2008, 987, 191-210
13. Tominari, T.; Hirata, M.; Matsumoto, C.; Inada, M.; Miyaura, C. Polymethoxy flavonoids, nobiletin and tangeretin, prevent lipopolysaccharide- induced inflammatory bone loss in an experimental model for periodontitis J. Pharmacol. Sci. 2012, 119, 390-394
14. Yang, Y. T.; Luo, H. J.; Ye, Y. S.; Liao, J. H.; Li, Y. L. Study on the extraction of polymethoxylated flavones from Citrus reticulata 'Chachi' of different storage years Sci. Tech. Food Ind. 2011, 9, 258-260 (In Chinese)
15. Meyer, G.; Deplanche, M.; Schelcher, F. Human and bovine respiratory syncytial virus vaccine research and development Comp. Immunol. Microbiol. Infect. Dis. 2008, 31, 191-225
16. Antonelli, G.; Turriziani, O. Antiviral therapy: Old and current issues Int. J. Antimicrob. Agents 2012, 40, 95-102
17. Glatthaar Saalmüller, B.; Rauchhaus, U.; Rode, S.; Haunschild, J.; Saaalmuller, A. Antiviral activity in vitro of two preparations of the herbal medicinal product Sinupret against viruses causing respiratory infections Phytomedicine 2011, 19, 1-7
18. Li, Y. L.; Leung, K. T.; Yao, F. H.; Ooi, L. S.; Ooi, V. E. C. Antiviral flavans from the leaves of Pithecellobium cylpearia J. Nat. Prod. 2006, 69 (5) 833-835
19. Cos, P.; Vlietinck, A. J.; Berghe, D. V.; Maes, L. Anti-infective potential of natural products: How to develop a stronger in vitro 'proof-of-concept' J. Ethnopharmacol. 2006, 106, 290-302
20. Shigeta, S.; Mori, S.; Baba, M.; Ito, M.; Honzumi, K.; Nakamara, K.; Oshitani, H.; Numazaki, Y.; Matsuda, A.; Obara, T.; Shuto, S.; De Clercq, E. Antiviral activities of ribavirin, 5-ethynyl-1-D-ribofuranosylimidazole-4- carboxamide, and 6′-(R)-6′-C -methylneplanocin against several ortho-and paramyxoviruses Antimicrob. Agents Chemother. 1992, 36, 435-439
21. Ho, W. S.; Xue, J. Y.; Sun, S. S. M.; Ooi, V. E. C.; Li, Y. L. Antiviral activity of Daphnoretin isolated from Wikstroemia indica Phytother. Res. 2010, 24, 657-660
22. Li, Y. L.; But, P. P. H.; Ooi, V. E. C. Antiviral activity and mode of action of caffeoylquinic acids from Schefflera heptaphylla (L.) Frodin Antivir. Res. 2005, 68, 1-9
23. 3 against respiratory syncytial virus infection in vitro and in vivo Antivir. Res. 2000, 47, 41-51
24. Trasino, S. E.; Kim, Y. S.; Wang, T. T. Y. Ligand, receptor, and cell type-dependent regulation of ABCA1 and ABCG1 mRNA in prostate cancer epithelial cells Mol. Cancer Ther. 2009, 8, 1934-1945
25. Nagase, H.; Omae, N.; Omori, A.; Nakagawasai, O.; Tadano, T.; Yokosuka, A.; Sashida, Y.; Mimaki, Y.; Yamakuni, T.; Ohizumi, Y. Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities Biochem. Biophys. Res. Commun. 2005, 337, 1330-1336
26. Sharma, A.; Tendulkar, A. V.; Wangikar, P. P. Drug discovery against H1N1 virus (influenza A virus) via computational virtual screening approach Med. Chem. Res. 2011, 20, 1445-1449
27. Jiang, Y.; Wong, J. H.; Fu, M.; Ng, T. B.; Liu, Z. K.; Wang, C. R.; Li, N.; Qiao, W. T.; Wen, T. Y.; Liu, F. Isolation of adenosine, iso-sinensetin and dimethylguanosine with antioxidant and HIV-1 protease inhibiting activities from fruiting bodies of Cordyceps militaris Phytomedicine 2011, 18, 189-193
28. Sun, Z. W.; Pan, Y. B.; Lu, L. Respiratory syncytial virus entry inhibitors targeting the F protein Viruses 2013, 5, 211-225
29. Remer, K. A.; Brcic, M.; Jungi, T. W. Toll-like receptor-4 is involved in elicting an LPS-induced oxidative burst in neutrophils Immunol. Lett. 2003, 85, 75-80
30. Santoro, M. G.; Rossi, A.; Amici, C. NF-kappaB and virus infection: Who controls whom EMBO J. 2003, 22, 2552-2560
31. Jiang, S. E.; Ryu, K. R.; Park, S. H.; Chuang, S.; Teruya, Y.; Han, M. J.; Woo, J. T.; Kim, D. Y. Nobiletin and tangeretin ameliorate scratching behavior in mice by inhibiting the action of histamine and the activation of NF-κB, AP-1 and p38 Int. Immonopharmocol. 2013, 1705-1878
32. Asenjo, A.; Mendieta, J.; Gonmez-Puertas, P.; Villanueva, N. Residues in human respiratory syncytial virus P protein that are essential for its activity on RNA viral synthesis Virus Res. 2008, 132, 160-173
33. Lay, M. K.; Gonzalez, P. A.; Leon, M. A.; Cespedes, P. F.; Bueno, S. M.; Riedel, C. A.; Kalergis, A. M. Advances in understanding respiratory syncytial virus infection in airway epithelial cells and consequential effects on the immune response Microbes Infect. 2013, 15, 230-242
34. Kim, Y.; Lee, C. Ribavirin efficiently suppresses porcine nidovirous replication Virus Res. 2013, 171, 44-53
35. Keck, M.; Mindru, C.; Kalil, A. C.; Mercer, D. F.; Florescu, D. F. Respiratory syncytial virus lower respiratory tract infection in a pediatric liver transplant recipient treated with oral ribavirin Pediatr. Transplant. 2012, 16, E348-E351