Prenylated flavonoids, promising nutraceuticals with impressive biological activities

Trends in Food Science and Technology

Volumn 44, Issue 1, 2015, Pages 93-104

  Yang, Xiaoman ^a,b   Jiang, Yueming ^a   Yang, Jiali ^a,b   He, Jirui ^a,b   Sun, Jian ^c   Chen, Feng ^d   Zhang, Mingwei ^e   Yang, Bao ^a  

^a SOUTH CHINA INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c NATIONAL ENGINEERING RESEARCH CENTER FOR NON FOOD BIOREFINERY   (China)

^d CLEMSON UNIVERSITY   (United States)

^e INSTITUTE OF ANIMAL SCIENCE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; DIETARY SUPPLEMENTS;

FLAVONOID; HIGH SPECIFICITY; NUTRACEUTICALS; PRENYLATED FLAVONOIDS; PRENYLTRANSFERASE; STRUCTURAL CHARACTERISTICS;

FLAVONOIDS;

EID: 84953364587     PISSN: 09242244     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tifs.2015.03.007     Document Type: Review

References (78)

1. Adesanya S.A., O'Neill M.J., Roberts M.F. Structure-related fungi toxicity of isoflavonoids. Physiological and Molecular Plant Pathology 1986, 29:95-103.
2. Akashi T., Sasaki K., Aoki T., Ayabe S.-i., Yazaki K. Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin. Plant Physiology 2009, 149:683-693.
3. Baliga M.S., Shivashankara A.R., Haniadka R., Dsouza J., Bhat H.P. Phytochemistry, nutritional and pharmacological properties of Artocarpus heterophyllus Lam (jackfruit): a review. Food Research International 2011, 44:1800-1811.
4. Barron D., Ibrahim R.K. Isoprenylated flavonoids - a survey. Phytochemistry 1996, 43:921-982.
5. Bohlmann F., Gören N.A. Three prenylated flavanoids from Helichrysum athrixiifolium. Phytochemistry 1984, 23:1338-1339.
6. Bonitz T., Alva V., Saleh O., Lupas A.N., Heide L. Evolutionary relationships of microbial aromatic prenyltransferases. PLoS One 2011, 6:e27336.
7. Botta B., Delle Monache G., Menendez P., Boffi A. Novel prenyltransferase enzymes as a tool for flavonoid prenylation. Trends in Pharmacological Sciences 2005, 26:606-608.
8. Botta B., Vitali A., Menendez P., Misiti D., Monache G.D. Prenylated flavonoids: pharmacology and biotechnology. Current Medicinal Chemistry 2005, 12:717-739.
9. Bourjot M., Apel C., Martin M.T., Grellier P., Nguyen V.H., Gueritte F., et al. Antiplasmodial, antitrypanosomal, and cytotoxic activities of prenylated flavonoids isolated from the stem bark of Artocarpus styracifolius. Planta Medica 2010, 76:1600-1604.
10. Butt M.S., Nazir A., Sultan M.T., Schroen K. Morus alba L. nature's functional tonic. Trends in Food Science & Technology 2008, 19:505-512.
11. Cerqueira F., Cordeiro-Da-Silva A., Araujo N., Cidade H., Kijjoa A., Nascimento M.S.J. Inhibition of lymphocyte proliferation by prenylated flavones: Artelastin as a potent inhibitor. Life Sciences 2003, 73:2321-2334.
12. Chadwick L.R., Pauli G.F., Farnsworth N.R. The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties. Phytomedicine 2006, 13:119-131.
13. Cos P., De Bruyne T., Apers S., Vanden Berghe D., Pieters L., Vlietinck A.J. Phytoestrogens: recent developments. Planta Medica 2003, 69:589-599.
14. Cottiglia F., Casu L., Bonsignore L., Casu M., Floris C., Leonti M., et al. New cytotoxic prenylated isoflavonoids from Bituminaria morisiana. Planta Medica 2005, 71:254-260.
15. Cuyckens F., Claeys M. Mass spectrometry in the structural analysis of flavonoids. Journal of Mass Spectrometry 2004, 39:1-15.
16. Dat N.T., Binh P.T., Quynh le T.P., Van Minh C., Huong H.T., Lee J.J. Cytotoxic prenylated flavonoids from Morus alba. Fitoterapia 2010, 81:1224-1227.
17. Dell'Agli M., Galli G.V., Dal Cero E., Belluti F., Matera R., Zironi E., et al. Potent inhibition of human phosphodiesterase-5 by icariin derivatives. Journal of Natural Products 2008, 71:1513-1517.
18. Delmulle L., Bellahcene A., Dhooge W., Comhaire F., Roelens F., Huvaere K., et al. Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine 2006, 13:732-734.
19. Delmulle L., Vanden Berghe T., Keukeleire D.D., Vandenabeele P. Treatment of PC-3 and DU145 prostate cancer cells by prenylflavonoids from hop (Humulus lupulus L.) induces a caspase-independent form of cell death. Phytotherapy Research 2008, 22:197-203.
20. Di Pietro A., Conseil G., Perez-Victoria J.M., Dayan G., Baubichon-Cortay H., Trompier D., et al. Modulation by flavonoids of cell multidrug resistance mediated by P-glycoprotein and related ABC transporters. Cellular and Molecular Life Sciences 2002, 59:307-322.
21. Gao X., Deeb D., Liu Y., Gautam S., Dulchavsky S.A., Gautam S.C. Immunomodulatory activity of xanthohumol: inhibition of T cell proliferation, cell-mediated cytotoxicity and Th1 cytokine production through suppression of NF-kappa B. Immunopharmacology and Immunotoxicology 2009, 31:477-484.
22. García-Lafuente A., Guillamón E., Villares A., Rostagno M.A., Martínez J.A. Flavonoids as anti-inflammatory agents: implications in cancer and cardiovascular disease. Inflammation Research 2009, 58:537-552.
23. Gester S., Metz P., Zierau O., Vollmer G. An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement. Tetrahedron 2001, 57:1015-1018.
24. Heide L. Prenyl transfer to aromatic substrates: genetics and enzymology. Current Opinion in Chemical Biology 2009, 13:171-179.
25. Henderson M.C., Miranda C.L., Stevens J.F., Deinzer M.L., Buhler D.R. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Xenobiotica 2000, 30:235-251.
26. Jukupovic J., Paredes L., Bohlmann F., Watson L. Prenyl flavanes from Marshallia species. Phytochemistry 1988, 27:3273-3275.
27. Kawamura T., Hayashi M., Mukai R., Terao J., Nemoto H. An efficient method for C8-prenylation of flavonols and flavanones. Synthesis-Stuttgart 2012, 44:1308-1314.
28. Kim S.J., Son K.H., Chang H.W., Kang S.S., Kim H.P. Tyrosinase inhibitory prenylated flavonoids from Sophora flavescens. Biological & Pharmaceutical Bulletin 2003, 26:1348-1350.
29. Ko W., Kang T., Kim N., Lee S., Kim Y., Ko G., et al. Lavandulylflavonoids: a new class of in vitro apoptogenic agents from Sophora flavescens. Toxicology In Vitro 2000, 14:429-433.
30. Kumano T., Tomita T., Nishiyama M., Kuzuyama T. Functional characterization of the promiscuous prenyltransferase responsible for furaquinocin biosynthesis: Identification of a physiological polyketide substrate and its prenylated reaction products. Journal of Biological Chemistry 2010, 285:39663-39671.
31. Kumazawa S., Ueda R., Hamasaka T., Fukumoto S., Fujimoto T., Nakayama T. Antioxidant prenylated flavonoids from propolis collected in Okinawa, Japan. Journal of Agricultural and Food Chemistry 2007, 55:7722-7725.
32. Kuzuyama T., Noel J.P., Richard S.B. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 2005, 435:983-987.
33. Lane G., Biggs D., Russell G., Sutherland O.W., Williams E.M., Maindonald J., et al. Isoflavonoid feeding deterrents for Costelytra zealandica structure -activity relationships. Journal of Chemical Ecology 1985, 11:1713-1735.
34. Lv X., Chen K., Ge B., Ma H., Song P., Cheng K. Comparative study on effect of 8-prenylnaringenin and naringenin on activity of osteoclasts cultured in vitro. China Journal of Chinese Materia Medica 2013, 1992-1996.
35. Milligan S.R., Kalita J.C., Pocock V., Van de Kauter V., Stevens J.F., Deinzer M.L., et al. The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids. Journal of Clinical Endocrinology & Metabolism 2000, 85:4912-4915.
36. Morimoto S., Tanabe H., Nonaka G.I., Nishioka I. Tannins and related-compounds. 62. Prenylated flavan-3-ols and procyanidins from Illicium-anisatum. Phytochemistry 1988, 27:907-910.
37. Nascimento M.S.J., Cidade H., Pinto M., Kijjoa A. Anticomplementary activity of prenylated flavones from Artocarpus elasticus. Pharmaceutical and Pharmacological Letters 1997, 7:135-137.
38. Nešuta O., López-Abán J., Shariati F., Yepes E., Navrátilová A., Šmejkal K., et al. Polyphenols as inhibitors of NO production in LPS-stimulated rat macrophages. Journal of Natural Pharmaceutical 2011, 2:15-19.
39. Neves M.P., Cidade H., Pinto M., Silva A., Gales L., Damas A.M., et al. Prenylated derivatives of baicalein and 3, 7-dihydroxyflavone: synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis. European Journal of Medicinal Chemistry 2011, 46:2562-2574.
40. Neves M.P., Lima R.T., Choosang K., Pakkong P., Jose Nascimento M.d.S., Helena Vasconcelos M., et al. Synthesis of a natural chalcone and its prenyl analogs - evaluation of tumor cell growth-inhibitory activities, and effects on cell cycle and apoptosis. Chemistry & Biodiversity 2012, 9:1133-1143.
41. Nguyen Tien D., Phung Thi Xuan B., Le Thi Phuong Q., Chau Van M., Hoang Thanh H., Lee J.J. Cytotoxic prenylated flavonoids from Morus alba. Fitoterapia 2010, 81:1224-1227.
42. Nijveldt R.J., van Nood E., van Hoorn D.E.C., Boelens P.G., van Norren K., van Leeuwen P.A.M. Flavonoids: a review of probable mechanisms of action and potential applications. The American Journal of Clinical Nutrition 2001, 74:418-425.
43. Quan W., Lee H.J., Kim C.Y., Noh C.W., Um B.H., Oak M.-H., et al. Anti-allergic prenylated flavonoids from the roots of Sophora flavescens. Planta Medica 2008, 74:168-170.
44. de Rijke E., Out P., Niessen W.M.A., Ariese F., Gooijer C., Brinkman U.A. Analytical separation and detection methods for flavonoids. Journal of Chromatography A 2006, 1112:31-63.
45. Rodriguez R.J., Miranda C.L., Stevens J.F., Deinzer M.L., Buhler D.R. Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes. Food and Chemical Toxicology 2001, 39:437-445.
46. Sasaki K., Mito K., Ohara K., Yamamoto H., Yazaki K. Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens. Plant Physiology 2008, 146:1075-1084.
47. Sasaki K., Tsurumaru Y., Yamamoto H., Yazaki K. Molecular characterization of a membrane-bound prenyltransferase specific for isoflavone from Sophora flavescens. Journal of Biological Chemistry 2011, 286:24125-24134.
48. Sasaki K., Tsurumaru Y., Yazaki K. Prenylation of flavonoids by biotransformation of yeast expressing plant membrane-bound prenyltransferase SfN8DT-1. Bioscience Biotechnology and Biochemistry 2009, 73:759-761.
49. Shen G., Huhman D., Lei Z., Snyder J., Sumner L.W., Dixon R.A. Characterization of an isoflavonoid-specific prenyltransferase from Lupinus albus. Plant Physiology 2012, 159:70-80.
50. Shin H.J., Kim H.J., Kwak J.H., Chun H.O., Kim J.H., Park H., et al. A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5. Bioorganic & medicinal chemistry letters 2002, 12:2313-2316.
51. Shou Q.-Y., Fu R.-Z., Tan Q., Shen Z.-W. Geranylated flavonoids from the roots of Campylotropis hirtella and their immunosuppressive activities. Journal of Agricultural and Food Chemistry 2009, 57:6712-6719.
52. Simons R., Gruppen H., Bovee T.F., Verbruggen M.A., Vincken J.P. Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs). Food & Function 2012, 3:810-827.
53. Simons R., Vincken J.-P., Bakx E.J., Verbruggen M.A., Gruppen H. A rapid screening method for prenylated flavonoids with ultra-high-performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts. Rapid Communications in Mass Spectrometry 2009, 23:3083-3093.
54. Simons R., Vincken J.-P., Mol L.M., The S.M., Bovee T.H., Luijendijk T.C., et al. Agonistic and antagonistic estrogens in licorice root (Glycyrrhiza glabra). Analytical and Bioanalytical Chemistry 2011, 401:305-313.
55. Simons R., Vincken J.-P., Roidos N., Bovee T.F.H., van Iersel M., Verbruggen M.A., et al. Increasing soy isoflavonoid content and diversity by simultaneous malting and challenging by a fungus to modulate estrogenicity. Journal of Agricultural and Food Chemistry 2011, 59:6748-6758.
56. Sofi S.N., Shakeel-u R., Qazi P.H., Lone S.H., Bhat H.M., Bhat K.A. Isolation, identification, and simultaneous quantification of five major flavonoids in Epimedium elatum by high performance liquid chromatography. Journal of Liquid Chromatography & Related Technologies 2014, 37:1104-1113.
57. Somjen D., Katzburg S., Vaya J., Kaye A.M., Hendel D., Posner G.H., et al. Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues. The Journal of Steroid Biochemistry and Molecular Biology 2004, 91:241-246.
58. Stec E., Li S.-M. 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. Archives of Microbiology 2012, 194:589-595.
59. Stevens J.F., Ivancic M., Hsu V.L., Deinzer M.L. Prenylflavonoids from Humullus lupulus. Phytochemistry 1997, 44:1575-1585.
60. Stevens J.F., Page J.E. Xanthohumol and related prenylflavonoids from hops and beer: to your good health. Phytochemistry 2004, 65:1317-1330.
61. Stevens J.F., Taylor A.W., Deinzer M.L. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A 1999, 832:97-107.
62. Suffness M., Douros J. Current status of the NCI plant and animal product program. Journal of Natural Products 1982, 45:1-14.
63. Sugiyama A., Linley P.J., Sasaki K., Kumano T., Yamamoto H., Shitan N., et al. Metabolic engineering for the production of prenylated polyphenols in transgenic legume plants using bacterial and plant prenyltransferases. Metabolic Engineering 2011, 13:629-637.
64. Tahara S., Katagiri Y., Ingham J.L., Mizutani J. Prenylated flavonoids in the roots of yellow lupin. Phytochemistry 1994, 36:1261-1271.
65. Tekel J., de Keukeleire D., Rong H.J., Daeseleire E., van Peteghem C. Determination of the hop-derived phytoestrogen, 8-prenylnaringenin, in beer by gas chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry 1999, 47:5059-5063.
66. Terao J., Mukai R. Prenylation modulates the bioavailability and bioaccumulation of dietary flavonoids. Archives of Biochemistry and Biophysics 2014, 559:12-16.
67. Thongnest S., Lhinhatrakool T., Wetprasit N., Sutthivaiyakit P., Sutthivaiyakit S. Eriosema chinense: a rich source of antimicrobial and antioxidant flavonoids. Phytochemistry 2013, 96:353-359.
68. Tischer S., Metz P. Selective C-6 prenylation of flavonoids via europium(III)-catalyzed Clasien rearrangement and cross-metathesis. Advanced Synthesis & Catalysis 2007, 349:147-151.
69. Tsimogiannis D.I., Oreopoulou V. The contribution of flavonoid C-ring on the DPPH free radical scavenging efficiency. A kinetic approach for the 3',4'-hydroxy substituted members. Innovative Food Science & Emerging Technologies 2006, 7:140-146.
70. Tsurumaru Y., Sasaki K., Miyawaki T., Momma T., Umemoto N., Yazaki K. An aromatic prenyltransferase-like gene HlPT-1 preferentially expressed in lupulin glands of hop. Plant Biotechnology 2010, 27:199-204.
71. Wen L.R., Wu D., Jiang Y.M., Prasad K.N., Lin S., Jiang G.X., et al. Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and evaluation of anticancer activities. Journal of Functional Foods 2014, 6:555-563.
72. Xu M.-J., Wu B., Ding T., Chu J.-H., Li C.-Y., Zhang J., et al. Simultaneous characterization of prenylated flavonoids and isoflavonoids in Psoralea corylifolia L. by liquid chromatography with diode-array detection and quadrupole time-of-flight mass spectrometry. Rapid Communications in Mass Spectrometry 2012, 26:2343-2358.
73. Yang B., Chen F., Hua Y.L., Huang S.S., Lin S., Wen L.R., et al. Prooxidant activities of quercetin, p-courmaric acid and their derivatives analysed by quantitative structure-activity relationship. Food Chemistry 2012, 131:508-512.
74. Yang B., Jiang Y.M., Shi J., Chen F., Ashraf M. Extraction and pharmacological properties of bioactive compounds from longan (Dimocarpus longan Lour.) fruit - a review. Food Research International 2011, 44:1837-1842.
75. Yazaki K., Sasaki K., Tsurumaru Y. Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry 2009, 70:1739-1745.
76. Zeng L., Fukai T., Nomura T., Zhang R.Y., Lou Z.C. Phenolic constituents of Glycyrrhiza species. 8. 4 new prenylated flavonoids, glyasperin-a, glyasperin-b, glyasperin-c, and glyasperin-d from the roots of Glycyrrhiza-aspera. Heterocycles 1992, 34:575-587.
77. Zhao F., Watanabe Y., Nozawa H., Daikonnya A., Kondo K., Kitanaka S. Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). Journal of Natural Products 2005, 68:43-49.
78. Zheng Z.-P., Chen S., Wang S., Wang X.-C., Cheng K.-W., Wu J.-J., et al. Chemical components and tyrosinase inhibitors from the twigs of Artocarpus heterophyllus. Journal of Agricultural and Food Chemistry 2009, 57:6649-6655.