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Review

A systematic review on biological activities of prenylated flavonoids

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Pages 655-660 | Received 20 Mar 2013, Accepted 06 Oct 2013, Published online: 21 Nov 2013

References

  • Anonymous. (2007). Guidance for industry: Evidence-based review system for the scientific evaluation of health claims, U.S. Department of Health and Human Services Food and Drug Administration Centre for Food Safety and Applied Nutrition. U.S. Food and Drug Administration [Online]. Available from: http://www.fda.gov/Food/GuidanceRegulation/GuidanceDocumentsRegulatoryInformation/LabelingNutrition/ucm073332.htm [last accessed June 2007]
  • Barron D, Ibrahim RK. (1996). Isoprenylated flavonoids – A survey. Phytochemistry 43:921–82
  • Botta B, Vitali A, Menendez P, et al. (2005). Prenylated flavonoids: Pharmacology and biotechnology. Curr Med Chem 12:717–39
  • Cassidy CE, Setzer WN. (2010). Cancer-relevant biochemical targets of cytotoxic Lonchocarpus flavonoids: A molecular docking analysis. J Mol Model 16:311–26
  • Cho JK, Ryu YB, Curtis-Long MJ, et al. (2011). Inhibition and structural reliability of prenylated flavones from the stem bark of Morus lhou on β-secretase (BACE-1). Bioorg Med Chem Lett 21:2945–8
  • Cho MY, Park SY, et al. (2012). Geranyl derivative of phloroacetophenone induces cancer cell-specific apoptosis through Bax-mediated mitochondrial pathway in MCF-7 human breast cancer cells. Biol Pharm Bull 35:98–104
  • Choi EJ, Kwon HC, Sohn YC, et al. (2009). Four flavonoids from Echinosophora koreensis and their effects on alcohol metabolizing enzymes. Arch Pharm Res 32:851–5
  • Dat NT, Binh PT, Quynh TP, et al. (2010). Cytotoxic prenylated flavonoids from Morus alba. Fitoterapia 81:1224–7
  • Dufall KG, Ngadjui BT, Simeon KF, et al. (2003). Antioxidant activity of prenylated flavonoids from the West African medicinal plant Dorstenia mannii. J Ethnopharmacol 87:67–72
  • Eaves FF. (2011). Got evidence? Stem cells, bias, and the level of evidence ladder: Commentary on: “ASAPS/ASPS position statement on stem cells and fat grafting”. Aesthet Surg J 31:718–22
  • Evidence-Based Medicine Working Group. (1992). Evidence-based medicine. A new approach to teaching the practice of medicine. JAMA 268:2420–5
  • Feng T, Wang RR, Cai XH, et al. (2010). Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata. Chem Pharm Bull (Tokyo) 58:971–5
  • Habtemariam S. (2012). The anti-obesity potential of sigmoidin A. Pharm Biol 50:1519–22
  • Halabalaki M, Alexi X, Aligiannis N, et al. (2006). Estrogenic activity of isoflavonoids from Onobrychis ebenoides. Planta Med 72:488–93
  • Hatano T, Shintani Y, Aga Y, et al. (2000). Phenolic constituents of licorice: Structures of glicophenone and glicoisoflavanone, and effects of licorice phenolics on methicillin-resistant Staphylococcus aureus. Chem Pharm Bull (Tokyo) 48:1286–92
  • Hemingway P, Brereton N. (2009). What is a systematic review? Evidence based medicine [Online].. Available from: http://www.medicine.ox.ac.uk/bandolier/painres/download/whatis/syst-review.pdf [last accessed 09 April 2009]
  • Heyerick A, Vervarcke S, Depypere H, et al. (2006). A first prospective, randomized, double-blind, placebo-controlled study on the use of a standardized hop extract to alleviate menopausal discomforts. Maturitas 54:164–75
  • Huang YC, Hwang TL, Chang CS, et al. (2009). Anti-inflammatory flavonoids from the rhizomes of Helminthostachys zeylanica. J Nat Prod 72:1273–8
  • Ibrahim RK. (2005). A forty-year journey in plant research: Original contributions to flavonoid biochemistry. Can J Bot 83:433–50
  • Inui S, Hosoya T, Shimamura Y, et al. (2012). Solophenols B-D and Solomonin: New prenylated polyphenols isolated from propolis collected from the Solomon Islands and their antibacterial activity. J Agric Food Chem 60:11765–70
  • Jang J, Na M, Thuong PT, et al. (2008). Prenylated flavonoids with PTP1B inhibitory activity from the root bark of Erythrina mildbraedii. Chem Pharm Bull (Tokyo) 56:85–8
  • Jayasinghe UL, Samarakoon TB, Kumarihamy BM, et al. (2008). Four new prenylated flavonoids and xanthones from the root bark of Artocarpus nobilis. Fitoterapia 79:37–41
  • Jones G, Campbell CA, Pye BJ, et al. (1996). Repellent and oviposition-deterring effects of hop beta acids on the two-spotted spider mite, Tetranychus urticae. Pesticide Sci 47:165–9
  • Jung HA, Jeong DM, Chung HY, et al. (2008). Re-evaluation of the antioxidant prenylated flavonoids from the roots of Sophora flavescens. Biol Pharm Bull 31:908–15
  • Jung HA, Moon HE, Oh SH, et al. (2012). Kinetics and molecular docking studies of kaempferol and its prenylated derivatives as aldose reductase inhibitors. Chem Biol Interact 197:110–18
  • Jung HA, Yokozawa T, Kim BW, et al. (2010). Selective inhibition of prenylated flavonoids from Sophora flavescens against BACE1 and cholinesterases. Am J Chin Med 38:415–29
  • Kenéz A, Juhász L, Lestár Z, et al. (2007). Synthesis and antifungal activity of naturally occurring O- and C-prenylated flavanones. Acta Pharm Hung 77:5–10
  • Khaomek P, Ichino C, Ishiyama A, et al. (2008). In vitro antimalarial activity of prenylated flavonoids from Erythrina fusca. J Nat Med 62:217–20
  • Kim SJ, Son KH, Chang HW, et al. (2003). Tyrosinase inhibitory prenylated flavonoids from Sophora flavescens. Biol Pharm Bull 26:1348–50
  • Ko HH, Lu YH, Yang SZ, et al. (2005). Cytotoxic prenylflavonoids from Artocarpus elasticus. J Nat Prod 68:1692–5
  • Kretzschmar G, Zierau O, Wober J, et al. (2010). Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein. J Steroid Biochem Mol Biol 118:1–6
  • Kumazawa S, Ueda R, Hamasaka T, et al. (2007). Antioxidant prenylated flavonoids from propolis collected in Okinawa, Japan. J Agric Food Chem 55:7722–5
  • Kupperman HS, Blatt MH, Wiesbader H, Filler W. (1953). Comparative clinical evaluation of estrogenic preparations by the menopausal and amenorrheal indices. J Clin Endocrinol Metab 13:688–703
  • Lee BW, Lee JH, Gal SW, et al. (2006). Selective ABTS radical-scavenging activity of prenylated flavonoids from Cudrania tricuspidata. Biosci Biotechnol Biochem 70:427–32
  • Li X, Wang D, Xia MY, et al. (2009). Cytotoxic prenylated flavonoids from the stem bark of Maackia amurensis. Chem Pharm Bull 57:302–6
  • Ma HP, Ming LG, Ge BF, et al. (2011). Icariin is more potent than genistein in promoting osteoblast differentiation and mineralization in vitro. J Cell Biochem 112:916–23
  • Madan S, Singh GN, Kohli K, et al. (2009). Isoflavonoids from Flemingia strobilifera (L) R. Br. Roots. Acta Pol Pharm 66:297–303
  • Milligan S, Kalita J, Pocock V, et al. (2002). Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction 123:235–42
  • Ming LG, Chen KM, Xian CJ. (2011). Functions and action mechanisms of flavonoids genistein and icariin in regulating bone remodeling. J Cell Physiol 112:916–23
  • Morel S, Landreau A, Nguyen VH, et al. (2012). Preparative isolation, fast centrifugal partition chromatography purification and biological activity of cajaflavanone from Derris ferruginea stems. Phytochem Anal 23:152–8
  • Mukne AP, Viswanathan V, Phadatare AG. (2011). Structure pre-requisites for isoflavones as effective antibacterial agents. Pharmacog Rev 5:13–18
  • Niu HM, Zeng DQ, Long CL, et al. (2010). Clerodane diterpenoids and prenylated flavonoids from Dodonaea viscose. J Asian Nat Prod Res 12:7–14
  • Oh I, Yang WY, Chung SC, et al. (2011). In vitro sortase A inhibitory and antimicrobial activity of flavonoids isolated from the roots of Sophora flavescens. Arch Pharm Res 34:217–22
  • Oh WK, Kim BY, Oh H, et al. (2005). Phospholipase C gamma1 inhibitory activities of prenylated flavonoids isolated from Erythrina senegalensis. Planta Med 71:780–2
  • Omisore NO, Adewunmi CO, Iwalewa EO, et al. (2005). Antitrichomonal and antioxidant activities of Dorstenia barteri and Dorstenia convexa. Braz J Med Biol Res 38:1087–94
  • Oosterhuis WP, Bruns DE, Watine J, et al. (2004). Evidence-based guidelines in laboratory medicine: Principles and methods. Clin Chem 50:806–18
  • Paoletti T, Fallarini S, Gugliesi F, et al. (2009). Anti-inflammatory and vascularprotective properties of 8-prenylapigenin. Eur J Pharmacol 620:120–30
  • Park KH, Park YD, Han JM, et al. (2006). Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata. Bioorg Med Chem Lett 16:5580–3
  • Pedro M, Ferreira MM, et al. (2005). Artelastin is a cytotoxic prenylated flavone that disturbs microtubules and interferes with DNA replication in MCF-7 human breast cancer cells. Life Sci 7:293–311
  • Peluso MR, Miranda CL, Hobbs DJ, et al. (2010). Xanthohumol and related prenylated flavonoids inhibit inflammatory cytokine production in LPS-activated THP-1 monocytes: Structure-activity relationships and in silico binding to myeloid differentiation protein-2 (MD-2). Planta Med 76:1536–43
  • Peng J, Hartley RM, Fest GA, Mooberry SL. (2012). Amyrisins A-C, O-prenylated flavonoids from Amyris madrensis. J Nat Prod 75:494–6
  • Plazar J, Filipic M, Groothuis GM. (2008). Antigenotoxic effect of xanthohumol in rat liver slices. Toxicol in Vitro 22:318–27
  • Plazar J, Zegura B, Lah TT, Filipic M. (2007). Protective effects of xanthohumol against the genotoxicity of benzo(a)pyrene (BaP), 2-amino-3-methylimidazo [4,5-f] quinoline (IQ) and tert-butyl hydroperoxide (t-BOOH) in HepG2 human hepatoma cells. Mutat Res 63:1–8
  • Quan W, Lee HJ, Kim CY, et al. (2008). Anti-allergic prenylated flavonoids from the roots of Sophora flavescens. Planta Med 74:168–70
  • Ruddock PS, Charland M, Ramirez S, et al. (2011). Antimicrobial activity of flavonoids from Piper lanceaefolium and other Colombian medicinal plants against antibiotic susceptible and resistant strains of Neisseria gonorrhoeae. Sex Transm Dis 38:82–8
  • Sasaki H, Kashiwada Y, Shibatav H, Takaishi Y. (2012). Prenylated flavonoids from the roots of Desmodium caudatum and evaluation of their antifungal activity. Planta Med 78:1851–6
  • Shen G, Huhman D, Lei Z, et al. (2012). Characterization of an isoflavonoid-specific prenyltransferase from Lupinus albus. Plant Physiol 159:70–80
  • Shin HJ, Kim HJ, Kwak JH, et al. (2002). A prenylated flavonol, sophoflavescenol: A potent and selective inhibitor of cGMP phosphodiesterase 5. Bioorg Med Chem Lett 12:2313–16
  • Simons R, Gruppen H, Bovee TF, et al. (2012). Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs). Food Funct 3:810–27
  • Simpson B, Claudie D, Smith N, et al. (2010). Evaluation of the anti-inflammatory properties of Dodonaea polyandra, a Kaanju traditional medicine. J Ethnopharmacol 132:340–3
  • Sohn HY, Son KH, Kwon CS, et al. (2004). Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants: Morus alba L., Morus mongolica Schneider, Broussnetia papyrifera (L.) Vent, Sophora flavescens Ait and Echinosophora koreensis Nakai. Phytomedicine 11:666–72
  • Stec E, Li SM. (2012). Mutagenesis and biochemical studies on AuaA confirmed the importance of the two conserved aspartate-rich motifs and suggested difference in the amino acids for substrate binding in membrane-bound prenyltransferases. Arch Microbiol 194:589–95
  • Stevens JF, Miranda CL, Frei B, Buhler DR. (2003). Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: The alpha, beta-unsaturated keto functionality of 2′-hydroxychalcones as a novel antioxidant pharmacophore. Chem Res Toxicol 16:1277–86
  • Sun D, Hurdle JG, Lee R, et al. (2012). Evaluation of flavonoid and resveratrol chemical libraries reveals abyssinone II as a promising antibacterial lead. Chem Med Chem 7:1541–5
  • Sutthivaiyakit S, Thongnak O, Lhinhatrakool T, et al. (2009). Cytotoxic and antimycobacterial prenylated flavonoids from the roots of Eriosema chinense. J Nat Prod 72:1092–6
  • Togola A, Hedding B, Theis A, et al. (2009). 15-Lipoxygenase inhibitory effects of prenylated flavonoids from Erythrina senegalensis. Planta Med 75:1168–70
  • Ueng YF, Chen CC, Tsai CC, Soucek P. (2009). Differential inductive profiles of hepatic cytochrome P450s by the extracts of Sophora flavescens in male and female C57BL/6JNarl mice. J Ethnopharmacol 126:437–46
  • Wang Y, Tan W, Li WZ, Li Y. (2001). A facile synthetic approach to prenylated flavanones: First total syntheses of (±)-bonannione A and (±)-sophoraflavanone A. J Nat Prod 64:196–9
  • Wu JY, Chung KT, Liu YW, Lu FJ, et al. (2008). Synthesis and biological evaluation of novel C(6) modified baicalein derivatives as antioxidative agents. J Agric Food Chem 56:2838–45
  • Yazaki K, Sasaki K, Tsurumaru Y. (2009). Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry 70:1739–45
  • Zakaria I, Ahmat N, Jaafar FM, Widyawaruyanti A. (2012). Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba. Fitoterapia 83:968–72
  • Zhang Y, Li XL, Yao XS, Wong MS. (2008). Osteogenic activities of genistein derivatives were influenced by the presence of prenyl group at ring A. Arch Pharm Res 31:1534–9

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