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Bioflavonoids (bioavailable flavonoids, vitamin P) are a class of water-soluble plant pigments with antioxidant, anti-inflammatory, antiallergenic, antiviral, and anti-carcinogenic properties. This is the collective name given to rutin, hesperidin and quercetin and a range of other naturally occurring compounds including the oligomeric pro-cyanidins found in red wine. Strictly speaking, bioflavonoids are not true vitamins, though they are sometimes referred to as vitamin P. They are essential for the absorption of vitamin C, and the two should be taken together. Bioflavonoids are extremely necessary for the absorption of vitamin C, and bioflavonoids should be taken together. The human body does not produce bioflavonoids, they must be supplied through diet.
Bioflavonoids have antioxidant, anti-inflammatory, antiallergenic, antiviral, and anti-carcinogenic properties. Like vitamin A, vitamin C and vitamin E, bioflavonoids are antioxidants. Antioxidants can rid the body of free radicals, toxic byproducts of chemical reactions that take place in the body every day. The body is exposed to free radicals through exercise, pollution, smoking, and many other factors. Bioflavonoids are often used in vitamin C formulas because they enhance the absorption and action of this vitamin. Bioflavonoids help maximize the benefits of vitamin C by inhibiting its breakdown in the body.
Some of the most well known flavonoids, for example, include:
PCO(Proanthocyanidins)
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most potent PCOs are those bound to other PCOs |
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exist in many plants and red wine |
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commercially available sources are from grape seeds and bark from the maritime pine | |
| Quercetin |
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serves as backbone for other flavonoids such as citrus flavonoids: rutin, quercitrin, hesperidin |
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these derivatives have sugar molecules attached to the backbone |
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most active of the flavonoids | |
| Citrus bioflavonoids |
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include rutin, quercitrin, hesperidin, naringin |
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standardized mixture of rutinosides known as hydroxyethylrutosides (HER) |
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clinical results have been obtained in treatment of capillary permeability, easy bruising, hemorrhoids, and varicose veins | |
| Green Tea Polyphenols |
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derived from tea plant camellia sinensis |
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produced by steaming the fresh cut leaf |
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polyphenol indicates presence of phenolic ring in the chemical structure |
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polyphenols = flavonoids |
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polyphenols in green tea: catechin, epicatechin, epicatechin gallate, epigallocatechin gallate, and proanthocyanidins |
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epigallocatechin gallate = most significant active compound | |
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What is Bioflavonoids?
Bioflavonoids are a group of naturally occurring plant compounds, which act primarily as plant pigments and antioxidants. They exhibit a host of biological activities, most notably for their powerful antioxidant properties. Bioflavonoids work with other antioxidants to offer a system of protection. Numerous studies have shown their unique role in protecting vitamin C from oxidation in the body, thereby allowing the body to reap more benefits from vitamin C.
Bioflavonoids are present in all botanical supplement products and foods. In fact, many medicinal herbs owe their curative actions to the bioflavonoids they contain. Besides the important antioxidant effects, bioflavonoids help the body maintain health and function in many ways. They have been shown to be anti-mutagenic, anti-carcinogenic, anti-aging, and promote structure and function in the circulatory system.
Where it is found
Bioflavonoids are abundant in the pulp and rinds of citrus fruits and other foods containing vitamin C, including red wine, green tea, onions, grapefruit seeds, apples, and other fruits and berries. Many medicinal plants contain bioflavonoids such as ginkgo biloba, hawthorn and Chinese scullcap. Citrus flavonoids are found in citrus fruits, rutin in buckwheat, epigallocatechin gallate (EGCG) in green tea, anthocyanidins in bilberry, and naringenin in grapefruit. Oligomeric proanthocyanidins, are found in grape seeds and skins. Quercetin is found in onions, tea, and apples.
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Benefits / uses
The main health benefits of bioflavonoids fall into two categories: health-promoting effects and therapeutic effects. The health-promoting effects include better eyesight, improved cardiovascular health, increased capillary strength, improved structure of connective tissues and appearance of skin, and a stronger immune system. Bioflavonoids also offer the health-promoting effect of lowering the risk of some diseases, such as atherosclerosis, cancer, arthritis, and gastrointestinal disorders. The therapeutic applications include treating a variety of diseases and disorders. Several of these are coronary heart disease, allergies, inflammation, hemorrhoids, respiratory diseases, viral infections, some types of cancer, and peptic ulcers.
PCO’s
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increase intracellular Vitamin C levels |
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decrease capillary permeability and fragility |
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scavenge oxidants and free radicals |
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inhibit destruction of collagen |
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crosslinks collagen fibers to reinforce the natural crosslinking |
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prevents free radical damage |
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inhibits enzymatic cleavage of collagen by enzymes secreted by leukocytes in inflammation and microbes in infections |
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prevents release and synthesis and compounds that promote inflammation and allergies (histamines, prostaglandins, leukotrienes) |
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antioxidant effects are beneficial in: |
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aging process |
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chronic degenerative diseases (heart disease, arthritis, and cancer) |
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fat and cholesterol oxidation | |
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antioxidants are produced by: |
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inhibiting xanthine oxidase noncompetitively(oxygen free radicals) | |
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on the cellular level: PCOs are incorporated into the cell membranes along with the antioxidant effects offer great protection to cells against free radical damage. | |
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| Quercetin |
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anti-inflammatory activity due to inhibition of initial processes of inflammation |
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inhibits manufacture and release of histamine |
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potent antioxidant activity and Vitamin C sparing action |
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beneficial effects for diabetics |
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helps prevent diabetic cataracts, and retinopathy |
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enhances insulin secretion |
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protects pancreatic beta cells from free radical damage |
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antiviral activity |
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activity vs. herpes virus type 1, parainfluenzae3, polio virus type 1, and respiratory syncytial virus |
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in vivo, inhibits viral infection |
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may be of some benefit in the common cold | |
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| Citrus Bioflavonoids |
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antioxidant effects |
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increase intracellular Vitamin C, rutin, hesperidin, and HER |
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beneficial effects on capillary permeability and blood flow like PCOs |
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anti-allergy and anti-inflammatory effects like quercetin |
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| Green Tea Polyphenols |
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Potent antioxidant effects |
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Increase activity of antioxidant enzymes in the small intestines, liver, lungs, and small bowel |
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Inhibit formation of cancer causing compounds like nitrosamines in vitro |
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Suppressing activation of carcinogens |
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Trapping cancer causing agents |
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Forms of cancer that green tea prevents best: |
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Cancers of GI tract (stomach, small intestine, pancreas, colon) |
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Cancer of the lungs |
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Estrogen related cancers (inhibits estrogen interaction with its receptor) | |
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Consumption of green tea with meals inhibits formation of nitrosamines (nitrites combined with amino acids) | |
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Doses
No dosage has been determined but 500 mg per day is indicated for supplementation, typically recommended dosage for women in menopause is 1000 - 1500 milligrams a day.
Possible Side effects / Precautions / Possible Interactions:
Bioflavonoids are generally safe. Excesses will be stored to a limited extent in the body, though most of the excess will be eliminated in the urine and sweat. No consistent toxicity has been linked to the bioflavonoids. However, extremely high doses may cause diarrhea, pregnant women are advised not to take megadoses of bioflavonoids.
Research studies / References
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Flavonoids (isoflavonoids and neoflavonoids)., IUPAC Compendium of Chemical Terminology |
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Galeotti, F; Barile, E; Curir, P; Dolci, M; Lanzotti, V (2008). "Flavonoids from carnation (Dianthus caryophyllus) and their antifungal activity". Phytochemistry Letters 1: 44. doi:10.1016/j.phytol.2007.10.001. |
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Spencer, Jeremy P. E. (2008). "Flavonoids: modulators of brain function?". British Journal of Nutrition 99: ES60-77. doi:10.1017/S0007114508965776. PMID 18503736. |
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"Therapeutic potential of inhibition of the NF-κB pathway in the treatment of inflammation and cancer". Yamamoto and Gaynor 107 (2): 135 -- Journal of Clinical Investigation. http://www.jci.org/cgi/content/full/107/2/135?ijkey=a1e09ce2dbca283cec170598f2410b15d5f4304f&keytype2=tf_ipsecsha. |
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Cushnie TPT, Lamb AJ (2005). "Antimicrobial activity of flavonoids". International Journal of Antimicrobial Agents 26 (5): 343-356. doi:10.1016/j.ijantimicag.2005.09.002. PMID 16323269. |
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Cushnie TPT, Lamb AJ (2011). "Recent advances in understanding the antibacterial properties of flavonoids". International Journal of Antimicrobial Agents Epub ahead of print. doi:10.1016/j.ijantimicag.2011.02.014. PMID 21514796. |
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de Sousa RR, Queiroz KC, Souza AC, Gurgueira SA, Augusto AC, Miranda MA, Peppelenbosch MP, Ferreira CV, Aoyama H. (2007). "Phosphoprotein levels, MAPK activities and NFkappaB expression are affected by fisetin". J Enzyme Inhib Med Chem 22 (4): 439-444. doi:10.1080/14756360601162063. PMID 17847710. |
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Bagchi Manashi, Mark Milnes, Casey Williams, Jaya Balmoori, Xumei Ye, Sidney Stohs and Debasis Bagchi (1999). "Acute and chronic stress-induced oxidative gastrointestinal injury in rats, and the protective ability of a novel grape seed proanthocyanidin extract". Nutrition Research 19 (8): 1189-1199. doi:10.1016/S0271-5317(99)00080-9. |
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Lotito SB, Frei B (2006). "Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: cause, consequence, or epiphenomenon?". Free Radic. Biol. Med. 41 (12): 1727-46. doi:10.1016/j.freeradbiomed.2006.04.033. PMID 17157175. |
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Scientific Opinion on the substantiation of health claims related to various food(s)/food constituent(s) and protection of cells from premature aging, antioxidant activity, antioxidant content and antioxidant properties, and protection of DNA, proteins and lipids from oxidative damage pursuant to Article 13(1) of Regulation (EC) No 1924/20061, EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA)2, 3 European Food Safety Authority (EFSA), Parma, Italy, EFSA Journal 2010; 8(2):1489 |
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Williams RJ, Spencer JP, Rice-Evans C (April 2004). "Flavonoids: antioxidants or signalling molecules?". Free Radical Biology & Medicine 36 (7): 838-49. doi:10.1016/j.freeradbiomed.2004.01.001. PMID 15019969. |
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a b c "Studies force new view on biology of flavonoids", by David Stauth, EurekAlert!. Adapted from a news release issued by Oregon State University. URL accessed |
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UCLA news May 2008 - Fruits, vegetables, teas may protect smokers from lung cancer |
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Schuier M, Sies H, Illek B, Fischer H (1 October 2005). "Cocoa-related flavonoids inhibit CFTR-mediated chloride transport across T84 human colon epithelia". J. Nutr. 135 (10): 2320-5. PMID 16177189. http://jn.nutrition.org/cgi/reprint/135/10/2320. |
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Thirman MJ, Gill HJ, Burnett RC, Mbangkollo D, McCabe NR, Kobayashi H et al. (1993). "Rearrangement of the MLL gene in acute lymphoblastic and acute myeloid leukemias with 11q23 chromosomal translocations". N Engl J Med 329 (13): 909-14. doi:10.1056/NEJM199309233291302. PMID 8361504. |
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Strick R, Strissel PL, Borgers S, Smith SL, Rowley JD (2000). "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia". Proc Natl Acad Sci U S A 97 (9): 4790-5. doi:10.1073/pnas.070061297. PMC 18311. PMID 10758153. |
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http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=10758153. |
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Barjesteh van Waalwijk van Doorn-Khosrovani S, Janssen J, Maas LM, Godschalk RW, Nijhuis JG, van Schooten FJ (2007). "Dietary flavonoids induce MLL translocations in primary human CD34+ cells". Carcinogenesis 28 (8): 1703-9. doi:10.1093/carcin/bgm102. PMID 17468513. |
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http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=17468513. |
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Ross JA (1998). "Maternal diet and infant leukemia: a role for DNA topoisomerase II inhibitors?". Int J Cancer Suppl 11: 26-8. PMID 9876473. |
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Ross JA (2000). "Dietary flavonoids and the MLL gene: A pathway to infant leukemia?". Proc Natl Acad Sci U S A 97 (9): 4411-3. doi:10.1073/pnas.97.9.4411. PMC 34309. PMID 10781030. |
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http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=10781030. |
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Spector LG, Xie Y, Robison LL, Heerema NA, Hilden JM, Lange B et al. (2005). "Maternal diet and infant leukemia: the DNA topoisomerase II inhibitor hypothesis: a report from the children's oncology group". Cancer Epidemiol Biomarkers Prev 14 (3): 651-5. doi:10.1158/1055-9965.EPI-04-0602. PMID 15767345. http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=15767345. |
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Delphinidin Modulates the DNA-Damaging Properties of Topoisomerase II Poisons. Esselen, Jessica Fritz, Melanie Hutter and Doris Marko, Chem. Res. Toxicol., 2009, 22 (3), pp 554-564 doi:10.1021/tx800293v |
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Bandele, O.J.; Clawson, S.J.; Osheroff, N. (2008). "Dietary polyphenols as topoisomerase II poisons: B-ring substituents determine the mechanism of enzyme-mediated DNA cleavage enhancement". Chemical Research in Toxicology (6): 1253-1260doi:10.1021/tx8000785 |
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Paul Knekt, Jorma Kumpulainen, Ritva Järvinen, Harri Rissanen, Markku Heliovaara, Antti Reunanen, Timo Hakulinen, and Arpo Aromaa (September 2002). "Flavonoid intake and risk of chronic diseases". Am J Clin Nutr 76 (3): 560-8. PMID 12198000. |
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American Cancer Society, Quercetin |
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Lee KW, Kim YJ, Lee HJ, Lee CY (December 2003). "Cocoa has more phenolic phytochemicals and a higher antioxidant capacity than teas and red wine". J. Agric. Food Chem. 51 (25): 7292-5. doi:10.1021/jf0344385. PMID 14640573. |
|
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"Cocoa nutrient for 'lethal ills'". BBC News. http://news.bbc.co.uk/2/hi/health/.stm.[dead link] |
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Tsushida T., Suzuki, M. (1996) Content of flavonol glucosides and some properties of enzymes metabolizing the glucosides in onion. J. Jap. Soc. Food Sci. Technol., 43, 642-649. |
|
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Slimestad R, Fossen T, Vagen IM (December 2007). "Onions: a source of unique dietary flavonoids". J. Agric. Food Chem. 55 (25): 10067-80. doi:10.1021/jf0712503. PMID 17997520. |
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Marotti, M.; Piccaglia, R. (2002). "Characterization of Flavonoids in Different Cultivars of Onion (Allium cepa L.)". Journal of Food Science 67 (3): 1229. doi:10.1111/j.1365-2621.2002.tb09482.x. |
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Justesen U, Knuthsen P (2001). "Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes". Food Chem. 73 (2): 245-50. doi:10.1016/S0308-8146(01)00114-5. |
|
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Ewald C, Fjelkner-Modig S, Johansson K, Sjoholm I, akesson B (1999). "Effect of processing on major flavonoids in processed onions, green beans, and peas". Food Chem. 64 (2): 231-5. doi:10.1016/S0308-8146(98)00136-8. |
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Spedding G, Ratty A, Middleton E (September 1989). "Inhibition of reverse transcriptases by flavonoids". Antiviral Res. 12 (2): 99-110. doi:10.1016/0166-3542(89)90073-9. PMID 2480745. |
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The Lancet, (December 2007). "The devil in the dark chocolate". Lancet 370 (9605): 2070. doi:10.1016/S0140-6736(07)61873-X. PMID 18156011. http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(07)61873-X. |
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Serafini et al; Bugianesi, Rossana; Maiani, Giuseppe; Valtuena, Silvia; De Santis, Simone; Crozier, Alan (August 2003). "Plasma antioxidants from chocolate". Nature 424 (6952): 1013. doi:10.1038/4241013a. PMID 12944955. http://www.nature.com/nature/journal/v424/n6952/full/4241013a.html. |
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Serafini, M., Crozier, A., Bugianesi, R., Maiani, G., Valtuena, S., and Santis, S.D. (2003). "Nutrition: milk and absorption of dietary flavanols". Nature 424 (6952): 1013. doi:10.1038/4241013a. PMID 12944955. |
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Ververidis Filippos, F; Trantas Emmanouil, Douglas Carl, Vollmer Guenter, Kretzschmar Georg, Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal 2 (10): 1214-34. doi:10.1002/biot.200700084. PMID 17935117. |
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Hwang EI, Kaneko M, Ohnishi Y, Horinouchi S (May 2003). "Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster". Appl. Environ. Microbiol. 69 (5): 2699-706. doi:10.1128/AEM.69.5.2699-2706.2003. PMC 154558. PMID 12732539. http://aem.asm.org/cgi/pmidlookup?view=long&pmid=12732539. |
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Phenolics:figure 4 |
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Trantas Emmanouil, E; Panopoulos Nickolas, Ververidis Filippos (2009). "Metabolic engineering of the complete pathway leading to heterologous biosynthesis of various flavonoids and stilbenoids in Saccharomyces cerevisiae". Metabolic Engineering 11 (6): 355-366. doi:10.1016/j.ymben.2009.07.004. PMID 19631278. |
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Ververidis Filippos, F; Trantas Emmanouil, Douglas Carl, Vollmer Guenter, Kretzschmar Georg, Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part II: Reconstruction of multienzyme pathways in plants and microbes". Biotechnology Journal 2 (10): 1235-49. doi:10.1002/biot.200700184. PMID 17935118. | |
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