PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2008 | 58 | 4 |

Tytuł artykułu

Quercetin and its derivatives: chemical structure and bioactivity - a review

Autorzy

Treść / Zawartość

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Quercetin is one of the major dietary flavonoids belonging to a group of flavonols. It occurs mainly as glycosides, but other derivatives of quercetin have been identified as well. Attached substituents change the biochemical activity and bioavailability of molecules when compared to the aglycone. This paper reviews some of recent advances in quercetin derivatives according to physical, chemical and biological properties as well as their content in some plant derived food.

Słowa kluczowe

Wydawca

-

Rocznik

Tom

58

Numer

4

Opis fizyczny

p.407-413,fig.,ref.

Twórcy

autor
  • Research Group of Phytochemistry, Depatment of Chemistry, Agricultural University, Akademicka 15, 20-950 Lublin, Poland

Bibliografia

  • 1. Bartosz G., Druga twarz tlenu (The Second Face of Oxygen). 1995, PWN, Warszawa, pp. 179–203 (in Polish).
  • 2. Berardini N., Fezer R., Conrad J., Beifuss U., Carle R., Schieber A., Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins and pectin. J. Agric. Food Chem., 2005, 53, 1563–1570.
  • 3. Burda S., Oleszek W., Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem., 2001, 49, 2774–2779.
  • 4. Cermak R., Landgraf S., Wolffram S., The bioavailability of quercetin in pigs depends on the glycoside moiety and on dietary factors. J. Nutr., 2003, 133, 2802–2807.
  • 5. Cos P., Ying L., Calomme M., Hu J.P., Cimanga K., Poel B., Pieters L., Vlietinck A.J., Berghe D.V., Structure-activity realtionship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J. Nat. Prod., 1998, 61, 71–76.
  • 6. Chang Q., Wong Y.S., Identification of flavonoids in Hakmeitau beans (Vigna sinensis) by high performance liquid chromatography-electrospray mass spectrometry (LC-ESI/MS). J. Agric. Food Chem., 2004, 52, 6694–6699.
  • 7. Chen T.J., Jeng J.Y., Lin Ch.W., Wu Ch.Y., Chen Y.Ch., Quercetin inhibition of ROS- dependent and –independent apoptosis in rat glioma C6 cells. Toxicology, 2006, 223, 113–126.
  • 8. Chun S.S., Vattem D.A., Lin Y.T., Shetty K., Phenolic antioxidants from clonal oregano (Origanum vulgare) with antimicrobial activity against Helicobacter pylori. Proc. Biochem., 2005, 40, 809–816.
  • 9. Crespy V., Morand C., Besson C., Manach C., Demigne C., Remesy C., Quercetin, but not its glycosides is absorbed from the rat stomach. J. Agric. Food Chem., 2002, 50, 618–621.
  • 10. Day A.J., DuPont M.S., Ridley S., Rhodes M., Rhodes M.J.C., Morgan M.R.A., Williamson G., Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver β-glucosidase activity. FEBS Lett., 1998, 436, 71–75.
  • 11. Day A.J., Canada F.J., Diaz J.C., Kroon P.A., Mclauchlan R., Faulds C.B., Plumb G.W., Morgan M.R.A., Williamson G., Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett., 2000, 468, 166–170.
  • 12. Di Carlo G., Mascolo N., Izzo A.A., Capasso F., Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci., 1999, 65, 337–353.
  • 13. Erkoc S., Erkoc F., Keskin N., Theoretical investigation of quercetin and its radical isomers. J. Mol. Struct., 2003, 631, 141–146.
  • 14. Erlund I., Kosonen T., Alfthan G., Maenpaa J., Perttunen K., Kenraali J., Parantainen J., Aro A., Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers. Eur. J. Clin. Pharmacol., 2000, 56, 545–553.
  • 15. Flamini G., Antognoli E., Morelli I., Two flavonoids and other compounds from the aerial parts of Centaurea brakteata from Italy. Phytochemistry, 2001, 57, 559–564.
  • 16. Formica J.F., Regelson W., Review of the biology of quercetin and related bioflavonoids. Food Chem. Tox., 1995, 33, 1061–1080.
  • 17. Fossen T., Pedersen A.T., Andersen O.M., Flavonoids from red onion (Allium cepa). Phytochemistry, 1998, 47, 281–285.
  • 18. Gee J.M., DuPont M.S., Rhodes M.J., Johnson I.T., Quercetin glucosides interact with the intestinal glucose transport pathway. Free. Rad. Biol. Med., 1998, 25, 19–25.
  • 19. Goncalves B., Landbo A.K., Knudsen D., Silva A.P., Moutinho‑Pereira J., Rosa E., Meyer A.S., Effect of ripeness and postharvest storage on the phenolic profiles of cherries (Prunus avium L.). J. Agric. Food Chem., 2004, 52, 523–530.
  • 20. Goupy P., Dufour C., Loonis M., Dangles O., Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical. J. Agric. Food Chem., 2003, 51, 615–622.
  • 21. Graf B.A., Ameho C., Dolnikowski G.G., Milbury P.E., Chen Ch.Y., Blumberg J.B., Rat gastrointestinal tissues metabolize quercetin. J. Nutr., 2006, 136, 39–44.
  • 22. Grinberg L.N., Rachmilewitz E.A., Newmark H., Protective effects of rutin against hemoglobin oxidation. Biochem. Pharmacol., 1994, 48, 643–649.
  • 23. Harborne J.B., ed., The Flavonoids, Advances in Research Since 1986. 1994, Chapman & Hall, London, pp. 378–382.
  • 24. Harborne J.B., Williams Ch.A., Advances in flavonoid research since 1992. Phytochemistry, 2000, 55, 481–504.
  • 25. Hertog M.G.L., Hollman P.C.H., Katan M.B., Kromhout D., Estimation of daily intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr. Cancer, 1993, 20, 21–29.
  • 26. Hirose M., Takahashi S., Ogawa K., Futakuchi M., Shirai T., Phenolics: blocking agents for heterocyclic amine-induced carcinogenesis. Food Chem. Toxicol., 1999, 37, 985–992.
  • 27. Innocenti M., Gallori S., Giaccherini C., Ieri F., Vincieri F.F., Mulinacci N., Evaluation of the phenolic content in the aerial parts of different varieties of Cichorium intybus L. J. Agric. Food Chem., 2005, 53, 6497–6502.
  • 28. Janbaz K.H., Saeed S.A., Gilani A.H., Protective effect of rutin on paracetamol- and CCl4 –induced hepatotoxicity in rodents. Fitoterapia, 2002, 73, 557–563.
  • 29. Jürgenliemk G., Nahrstedt A., Phenolic compounds from Hypericum perforatum. Planta Medica, 2002, 68, 88.
  • 30. Kalinova J., Triska J., Vrchotova N., Distribution of vitamin E, squalene, epicatechin and rutin in common buckwheat plants (Fagopyrum esculentum Moech). J. Agric. Food Chem., 2006, 54, 5330–5335.
  • 31. Kaur Ch., Kapoor H.C., Antioxidants in fruits and vegetables – the millennium’s health. Int. J. Food Sci. Technol., 2001, 36, 703–725.
  • 32. Kim D.O., Chun O.K., Kim Y.J., Moon H.Y., Lee Ch.Y., Quantification of polyphenolics and their antioxidant capacity in fresh plums. J. Agric. Food Chem., 2003, 51, 6509–6515.
  • 33. Kuti J.O., Konuru H.B., Antioxidant capacity and phenolic content in leaf extracts of tree spinach (Cnidoscolus spp.). J. Agric. Food Chem., 2004, 52, 117–121.
  • 34. Lu Y., Foo L.Y., Polyphenolics of Salvia – a review. Phytochemistry, 2002, 59, 117–140.
  • 35. Materska M., Perucka I., Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L.). J. Agric. Food Chem., 2005, 53, 1750–1756.
  • 36. Materska M., Perucka I., Stochmal A., Piacente S., Oleszek W., Quantitative and qualitative determination of flavonoids and phenolic acid derivatives from pericarp of hot pepper fruit cv. Bronowicka Ostra. Pol. J. Food Nutr. Sci., 2003, 12/53, 72–76.
  • 37. Materska M., Perucka I., Konopacka M., Rogoliński J., Ślosarek K., Effect of 3-O-glycosylation of quercetin in 3-O rhamnosidic derivative on superoxide radical scavenging activity and reduction of DNA damages after X-ray radiation of human lymphocytes. Planta Medica (in press).
  • 38. Miyazawa M., Okuno Y., Nakamura S., Kosaka H., Antimutagenic activity of flavonoids from Pogostemon cablin. J. Agric. Food Chem., 2000, 48, 642–647.
  • 39. Morel I., Lescoat G., Cogrel P., Sergent O., Pasdeloup N., Brissot P., Cillard P., Cillard J., Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron- loaded rat hepatocyte cultures. Biochem. Pharmacol., 1993, 45, 13–19,
  • 40. Nemeth K., Piskuła M.K., Food content, processing, absorption and metabolism of onion flavonoids. Crit. Rev. Food Sci. Nutr., 2007, 47, 397–409.
  • 41. Nicolle C., Carnat A., Fraisse D., Lamaison J-L., Rock E., Michel H., Amouroux P., Remesy Ch., Characterisation and variation of antioxidant micronutrients in lettuce (Lactuca sativa folium). J. Sci. Food Agric., 2004, 84, 2061–2069.
  • 42. Obied H.K., Allen M.S., Bedgood N.R., Prenzler P.D., Robards K., Stockman R., Bioactivity and analysis of biofenols recovered from olive mill waste. J. Agric. Food Chem., 2005, 53, 823–837.
  • 43. Oomah B.D., Mazza G., Flavonoids and antioxidative activities in buckwheat. J. Agric. Food Chem., 1996, 44, 1746–1750.
  • 44. Prior R.L., Fruits and vegetables in the prevention of cellular oxidative damage. Am. J. Clin. Nutr., 2003, 78, 570–578.
  • 45. Reddy L., Odhav B., Bhoola K.D., Natural products for cancer prevention: a global perspective. Pharmacol. Ther., 2003, 99–113.
  • 46. Rice-Evans C.A., Miller J., Paganga G., Antioxidant properties of phenolic compounds. Trends Plant Sci., 1997, 2, 4, 152–159.
  • 47. Rotelli A.E., Guardia T., Juarez A.O., De la Rocha N.E., Pelzer L.E., Comparative study of flavonoids in experimental models of inflammation. Pharmacol. Res., 2003, 48, 601–606.
  • 48. Russo G.L., Ins and outs of dietary phytochemicals in cancer chemoprevention. Bioch. Pharm., 2007, 74, 533–544.
  • 49. Ryan D., Robards K., Lavee S., Determination of phenolic compounds in olives by reversed-phase chromatography and mass spectrometry. J. Chrom. A, 1999, 832, 87–96.
  • 50. Scalbert A., Morand Ch., Manach C., Remesy Ch., Absorption and metabolism of polyphenols in the gut and impact on health. Biomed. Pharmacother., 2002, 56, 276–282.
  • 51. Scalbert A., Williamson G., Dietary intake and bioavailability of polyphenols. J. Nutr., 2000, 130, 2073–2085.
  • 52. Shetty K., Role of proline-linked pentose phosphate pathway in biosynthesis of plant phenolics for functional food and environmental applications: a review. Proc. Bioch., 2004, 39, 789–803.
  • 53. Simmonds M.S.J., Importance of flavonoids in insect-plant interactions: feeding and oviposition. Phytochemistry, 2001, 56, 245–252.
  • 54. Singh R.P., Murthy C.K.N., Jayaprakasha G.K., Studies on the antioxidant activity of pomegranate (Punica granatum) peel and seed extracts using in vitro models. J. Agric. Food Chem., 2002, 50, 81–86.
  • 55. Slimestad R., Torskangerpoll K., Nateland H.S., Johannessen T., Giske N.H., Flavonoids from black chokeberries, Aronia melanocarpa. J. Food Comp. Anal., 2005a, 18, 61–68.
  • 56. Slimestad R., Verheul M.J., Seasonal variations in the level of plant constituents in greenhouse production of Cherry tomatoes. J. Agric. Food Chem., 2005b, 53, 3114–3119.
  • 57. Smith-Palmer A., Stewart J., Fyfe L., The potential application of plant essential oils as natural food preservatives in soft cheese. Food Microbiol., 2001, 18, 463–470.
  • 58. Son K.H., Kwon H.W., Chang H.W., Kim H.P., Kang S.S., Papyriflavonol A, a new prenylated flavonol from Broussonetia papyrifera. Fitoterapia, 2001, 72, 456–458.
  • 59. Souto X.C., Chiapusio G., Pellissier F., Relationships between phenolics and soil microorganisms in spruce forests: significance for natural regeneration. J. Chem. Ecol., 2000, 26, 2025–2034.
  • 60. Vilegas W., Sanommiya M., Rastrelli L., Pizza C., Isolation and structure elucidation of two new flavonoid glycosides from the infusion of Maytenus aquifolium leaves. Evaluation of the antiulcer activity of the infusion. J. Agric. Food Chem., 1999, 47, 403–406.
  • 61. Vurma M., Chung Y.K., Shellhammer T.H., Turek E.J., Yousef A.E., Use of phenolic compounds for sensitizing Listeria monocytogenes to high-pressure processing. Int. J. Food Microbiol., 2006, 106, 263–269.
  • 62. Walle T., Absorption and metabolism of flavonoids. Free Rad. Biol. Med., 2004, 36, 829–837.
  • 63. Wang L., Tu Y.Ch., Lian T.W., Hung J.T., Yen J.H., Wu M.J., Distinctive antioxidant and antiinflammatory effects of flavonols. J. Agric. Food Chem., 2006, 54, 9798–9804.
  • 64. Wiczkowski W., Piskuła M.K., Food flavonoids. Pol. J. Food Nutr. Sci., 2004, 13/54, 101–114.
  • 65. Williams Ch.A., Grayer R.J., Anthocyanins and other flavonoids. Nat. Prod. Rep., 2004, 21, 539–573.
  • 66. Williams R.J., Spencer P.E., Rice-Evans C. Flavonoids: antioxidants or signalling molecules? Free Rad. Biol. Med. 2004, 36, 838–849.
  • 67. Wolfram S., Blöck M., Ader P., Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine. J. Nutr., 2002, 132, 630–635.
  • 68. Yao L., Datta N., Tomas-Barberan F.A., Ferreres F., Martos I., Singanusong R., Flavonoids, phenolic acids and abscisic acid in Australian and New Zeland Leptospermum honeys. Food Chem., 2003, 81, 159–168.
  • 69. Zeng W., Wang S.Y., Oxygen radical absorbing capacity of phenolics in blueberries, cranberries, chokenberries and lingonberries. J. Agric. Food Chem., 2003, 51, 502–509.
  • 70. Zielińska M., Gülden M., Seibert H., Effects of quercetin and quercetin-3-O-glycosides on oxidative damage on rat C6 glioma cells. Env. Tox. Pharm., 2003, 13, 47–53.

Uwagi

PL
Rekord w opracowaniu

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

bwmeta1.element.agro-e5547df6-4ab1-4b12-8d12-587b6410416c
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.