Flavanols

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The Science of Flavonoids Erich Grotewold See book keywords and concepts

Figure 8.1), flavanols (or catechins) (e.g., epicatechin and gallocatechin) (Figure 8.2), anthocyanidins (e.g., cyanidin and pelargonidin) (Figure 8.3), and isoflavones (e.g., genistein and daidezin) (Figure 8.1) (Ross and Kasum, 2002). Flavonol Kaempferol Quercetin Qucrcetagetin Myricetin Isoflavone BiocnaninA Daidzein Genistein Flavan Naringenin Tarjfolin Fustin Nobiletm Tangeretm Figure 8.1 Structure of select flavones, flavonols, flavanones, flavanols, isoflavones, and flavans.

The 150 Healthiest Foods on Earth: The Surprising, Unbiased Truth About What You Should Eat and Why Jonny Bowden, Ph.D., C.N.S. See book keywords and concepts

The health benefits come from the flavanols and antioxidants, and those are found in real cocoa— in fact, that's the stuff that makes cocoa kind of bitter. So if you want the benefits of these flavanols in your diet, you've got to get the real deal chocolate—high-cocoa-content dark chocolate. You'll see the best of these bars with labels that say things like "60 percent cocoa" (70 percent or higher is even better, but much harder to find). Milk chocolate and white chocolate have virtually none of these health benefits.

The particular class of flavonoids found in cocoa are called flavanols, and the flavanols in cocoa prevent fatlike substances in the bloodstream from clogging the arteries. When you reduce the blood's ability to clot, you also reduce the risk of heart attack and stroke. (That's why they sometimes tell you to take a baby aspirin—for the same reason.) All these things make blood platelets less likely to stick together and cause clots. As an extra bonus, cocoa also contains magnesium, one of the most important minerals for heart health.

So if you want the benefits of these flavanols in your diet, you've got to get the real deal chocolate—high-cocoa-content dark chocolate. You'll see the best of these bars with labels that say things like "60 percent cocoa" (70 percent or higher is even better, but much harder to find). Milk chocolate and white chocolate have virtually none of these health benefits. Plus, the commercial candy bars are loaded with extra sugar, fat, waxes, and chemicals that are not what you want to be adding to your diet. And the more chocolate is processed, the more the beneficial flavonoids are lost.

The Science of Flavonoids Erich Grotewold See book keywords and concepts

Rice-Evans, C, 1995, Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants, Arch Biochem Biophys, 322: 339-346. Sastre, J., Pallardo, F. V., and Vina, J., 2000, Mitochondrial oxidative stress plays a key role in aging and apoptosis, IUBMB Life, 49: 427-435. Sazuka, M., Murakami, S., Isemura, M., Satoh, K., and Nukiwa, T., 1995, Inhibitory effects of green tea infusion on in vitro invasion and in vivo metastasis of mouse lung carcinoma cells, Cancer Lett, 98: 27-31. Schreier, P., 2005, Chemopreventive compounds in the diet, Dev Ophthalmol, 38: 1-58.

Structure of select flavones, flavonols, flavanones, flavanols, isoflavones, and flavans. They are widely distributed in foods and beverages of plant origin, such as fruits, vegetables, tea, cocoa, and wine. Numerous publications report their content in various foods (Kelm et al., 2005; Schreier, 2005). Within the subgroups of the flavonols and the flavones, the flavonol quercetin is the most frequently occurring compound in foods. Also common are kaempferol, myricetin, and the flavones apigenin and luteolin. Tea and onions are the main dietary sources of flavonols and flavones.

Identification and quantitation of flavanols and proanthocyanidins in foods: how good are the datas? Clin Dev Immunol, 12: 35-41. Khan, M. A., and Baseer, A., 2000, Increased malondialdehyde levels in coronary heart disease, J Pak Med Assoc, 50: 261-264. Khan, W. A., Wang, Z. Y„ Athar, M., Bickers, D. R., and Mukhtar, H., 1988, Inhibition of the skin tumorigenicity of (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene by tannic acid, green tea polyphenols and quercetin in Senear mice, Cancer Lett, 42: 7-12. Khanduja, K. L., Gandhi, R. K., Pathania, V.

Nuclear localization of flavonols also has been shown in Arabidopsis thaliana (Peer et al, 2001; Buer and Muday, 2004; Saslowsky et al, 2005) and flavanols in Tsuga canadensis, Taxus baccata, Metasequoia glyptostroboides, Coffea arabica, Prunus avium, and Camellia sinesis (Feucht et al, 2004a, 2004b). Catechin binding of histone proteins has been demonstrated in plants (Polster et al, 2003; Feucht et al, 2004b), suggesting that catechins might modulate nonspecific gene transcription.

Nutrition in the Prevention and Treatment of Disease Ann M. Coulston and Carol J. Boushey See book keywords and concepts

Flavanols for cardiovascular health: the science behind the sweetness. J. 152. Hypertens. 23(8), 1453-1459. 135. Rivas, M., et al. (2002). Soy milk lowers blood pressure in 153. men and women with mild to moderate essential hypertension. J. Nutr. 132(7), 1900-1902. 136. Teede, H. J., et al. (2006). Randomised, controlled, cross- 154. over trial of soy protein with isoflavones on blood pressure and arterial function in hypertensive subjects. J. Am. Coll. Nutr. 25(6), 533-540. Kreijkamp-Kaspers, S., et al. (2005).

A comparison of the antimutagenic potential of green, black and decaffeinated teas: Contribution of flavanols to the antimutagenic effect. Mutagenesis 11, 597-603. Gastrointestinal Health and Disease CHAPTER 30 ^ Intestinal Microflora and Diet in Health MERLIN W. ARIEFDJOHAN AND DENNIS A. SAVAIANO Department of Foods and Nutrition, Purdue University, West Lafayette, Indiana Contents I. Introduction 707 II. Distribution and Diversity of the Human Intestinal Microflora 707 III. Bacterial Colonization, Succession, and Metabolism 709 IV. Functions of the GI Tract Microflora 711 V.

The Science of Flavonoids Erich Grotewold See book keywords and concepts

Several flavonoids and phenolic compounds, including the epicatechin/gallate family of flavanols, are powerful inhibitors of nitrous acid-dependent nitration and DNA deamination in vitro (Oldreive et al., 1998). 2.3. Protective effects of flavonoids The protective effects of flavonoids in biological systems are ascribed to their capacity to transfer free radical electrons, chelate metal catalysts (Ferrali et al., 1997), activate antioxidant enzymes (Elliott et al., 1992), reduce alpha-tocopherol radicals (Hirano et al, 2001), and inhibit oxidases (Cos et al., 1998).

Foods that Fight Cancer Richard Beliveau, Ph.D. and Denis Gingras, Ph.D. See book keywords and concepts

It is this phytochemical content, in fact, that is responsible PRINCIPAL GROUPS OF PHYTOCHEMICALS FOUND IN FRUITS AND VEGETABLES Family Polyphenols Terpenes Sulfur compounds (sulfides) Saponins Flavonoids Phenolic acids Non-flavonoids —\ Carotenoids Monoterpenes Diallyl sulfides Isothiocyanates Triterpenoids Steroids Subclass Anthocyanidins Flavones flavanols Flavanones Flavonols Isoflavones Tanins Hydroxycinnamates Hydroxybenzoates Stibenes Coumarins Lignans Table 7 for the organoleptic properties that are so characteristic of these foods (bitterness, as-tringency, odour . . .

One class of compounds predominates, making up about one-third of the weight of the tea leaf: these are the polyphenols known as flavanols, more commonly known as catechins. Catechins are the heavyweights responsible for the anticancer activity of green tea. Like all other polyphenols, catechins are complex molecules that play a very important role in plant physiology. They possess antifungal and anti-bacterial properties that allow the plant to successfully resist invasion by a large number of pathogens.

Indian Herbal Remedies: Rational Western Therapy, Ayurvedic and Other Traditional Usage, Botany C. P. Khare See book keywords and concepts

The yellowish needles showed high concentration of flavanols, whereas browning needles contain very low amounts of flavanols. The needles contain an essential oil (0.55 %-0.82 %). The main components of the oil are limonene and phellandrene. The needles of a sample from Netherlands contained glycoside bound volatile compounds. Two lectins (glycoproteins) AAAi and AAA2 have been isolated from the bark. They showed agglutinating activity on human blood group A, B and 0. The fatty acid in the bark are palmitic, lino-leic, linolenic, oleic, and 14-methylhexadecanoic acid.

The ABC Clinical Guide to Herbs Mark Blumenthal See book keywords and concepts

ANTIOXIDANT: scavenges DPPH (UG more potent than UT reflected as lower IC50 value despite lower concentrations of alkaloids and flavanols), protects against deoxyribose degradation in a dose-dependent manner, and inhibits ABTS-radicals (Sandoval etal, 2002, 2000); effectively scavenges free radicals and inhibits lipid peroxidation (Piscoya etal.

Wirth and Wagner, 1997), sterols (p-sitosterol, stigmasterol, campesterol) (Senatore et al, 1989), flavanols (catechin, epigallocatechin, epicatechin and epigallocatechin) (Sandoval etai, 2002), tannins (Wagner etai, 1985b) and CAEs (Sheng ^/., 2001). Pharmacological Actions Human • Uncaria guianensis ANTI-INFLAMMATORY: significantly reduced pain associated with activity in patients with osteoarthritis of the knee (Piscoya et al, 2001). • Uncaria tomentosa—unspecified preparations ANTIMUTAGENIC: ingestion for 15 days decreased mutagenicity of one smoker's urine (Rizzi et al, 1993).

DPPH (UG more potent than UT despite lower concentrations of alkaloids and flavanols), protects against deoxyribose degradation in a dose-dependent manner, and inhibits ABTS-radicals (Sandoval etal., 2002); effectively scavenges free radicals and inhibits lipid peroxidation (Piscoya etal., 2001); protects human gastric epithelial cells from apoptosis induced by DPPH, peroxynitrite and H202 (Miller etal, 2001).

Fundamentals of Pharmacognosy and Phytotherapy Dr. Michael Heinrich, Joanne Barnes, Simon Gibbons and Elizabeth M. Williamson See book keywords and concepts

Cyclization can then occur to give a pyranone ring containing flavanone nucleus, which can either have the C2-C3 bond oxidized (unsaturated) to give the flavones or be hydroxylated at position C3 of the pyranone ring to give the flavanol group of flavonoids. The flavanols may then be further oxidized to yield the anthocyanins, which contribute to the brilliant blues of flowers and the dark colour of red wine.

Outsmart Your Cancer: Alternative Non-Toxic Treatments That Work Tanya Harter Pierce See book keywords and concepts

The seven subgroups of phytoestrogens are: isoflavones, coumestans, flavanones, flavones, flavanols, lignans, and chalcones. The isoflavones and coumestans are the most powerful of the phytoestrogens, with about a 10-fold stronger estrogenic effect than the others. Virtually all plants, including vegetables, fruits, seeds, legumes, and grains, have some form of phytoestrogen in them. Flavanones are primarily concentrated in citrus fruits, lignans are found in all fruits, vegetables, and cereals, and the stronger isoflavones and coumestans are mostly found in legumes.

The ABC Clinical Guide to Herbs Mark Blumenthal See book keywords and concepts

Antioxidant • Scavenges DPPH (UG more potent than UT despite lower concentrations of alkaloids and flavanols), protects against deoxyribose degradation in a dose-dependent manner, and inhibits ABTS-radicals (Sandoval etal, 2002; 2000). • Effectively scavenges free radicals and inhibits lipid peroxidation (Piscoya et al, 2001). • Protects human gastric epithelial cells from apoptosis induced by DPPH, peroxynitrite and H202 (Miller et al, 2001). • Reduces peroxynitrite-induced apoptosis in human gastric epithelial cells and in macrophages (Sandoval-Chacon et al, 1998).

Prescription for Dietary Wellness: Using Foods to Heal Phyllis A. Balch, CNC See book keywords and concepts

Tannins are generally categorized into two subgroups: hydrolyzable tannins, which include gallotannins, ellagitannins, and caffetannins; and condensed tannins, which are the oligomers and polymers of flavanols and include the proanthocyanidins.

Cancer & Natural Medicine: A Textbook of Basic Science and Clinical Research John Boik See book keywords and concepts

Proanthocyanidins are dimers of flavanols. In France, where much of the basic research on flavanols has taken place, they are termed "procyanidols" or in French "oligomeres procyanidoliques", or OPC. The abbreviation OPC is now used in many countries to refer to proanthocyanidins. The distribution of these compounds vary between plant species.

Certain flavanols are sometimes referred to by the trademark term pycnogenols, coined by the French researcher Professor Jack Masquelier. The term pycnogenol means "that which creates condensation," and refers to the tendency of flavanols to create dimers (two identical compounds joined together), oligomers (a few joined together), and polymers (many joined together). One group of flavanol dimers and oligomers are termed proanthocyanidins, and are discussed below in item 5. 3) Flavones and Flavonols. Flavones and flavonols are the most widely occurring flavonoids.

The ABC Clinical Guide to Herbs Mark Blumenthal See book keywords and concepts

Meyer-Buchtela, 1999; Scholz and Bertram, 1995). After fermentation from green tea to black tea, about 15% of the catechins remain unchanged and the rest convert into theaflavines and thearubigins. The components of prepared black tea infusion measured in weight % of extracted solids include 3-10% catechins, 12-18% thearubigins, 3—6% theaflavines, 6-8% flavonols, 10—12% phenolic acids and depsides, 8—11% xanthine alkaloids, 13-15% amino acids, and about 10% minerals (Graham, 1992).

U. tomentosa (Sandoval etal, 2002, 2000; Miller etal, 2001).The U. tomentosa plants occur naturally as two chemotypes that appear botanically identical, but are chemically different in their alkaloid content (Laus et al, 1997). One chemotype contains predominantly POAs with little or no TOAs, and the other contains TOAs with either no POAs or up to a considerable amount. TOAs are reported to act antagonistically to some POA activity (Wurm etal, 1998).

The Encyclopedia of Psychoactive Plants: Ethnopharmacology and Its Applications Christian Ratsch See book keywords and concepts

Constituents The entire plant contains flavanols, flavonoid compounds, tanning agents, vitamins (especially C), minerals, a glycoside, and arbutin derivatives (Pahlow 1993,254*). The inebriating constituents of the berries are apparently a metabolic product or a constituent of a parasitic fungus (Sclerotina megalospora Wot.) that often infects the fruits (Frohne and Pfander 1983, 111*). To date, however, no constituent has been isolated or identified (Roth et al. 1994, 718*).

The A.D.D. Nutrition Solution: A Drug-Free Thirty-Day Plan Marcia Zimmerman, C.N. See book keywords and concepts

These remarkable flavanols protect vitamin C and enhance its numerous antioxidant and coenzyme effects, especially in the brain and eyes. These, and antihistamine, anti-inflammatory, and immune-boosting effects, make OPCs an essential part of my 30-Day Plan, but that's not all they do! OPCs affect the metabolic enzymes that regulate neurotransmitters in ways that are not entirely clear and are now being studied extensively.

Beating Cancer with Nutrition Patrick Quillin, PhD,RD,CNS See book keywords and concepts

Some of the main categories of bioflavonoids include: 0 anthocyanins; deep purple compounds found in black grapes, beets, red onions, and berries {} catechins and epigallocatechin, which are polyphenols found in apples and green tea () ellagic acid, a true anti-cancer compound found in cranberries, raspberries, and other berries, v" flavones, found in citrus fruit, red grapes and green beans 0 flavanols, such as quercetin, myricetin, found in kale, spinach, onions, apples, and black tea () flavanones, such as hesperidin and naringen found in citrus fruits of grapefruit, oranges and lemons.

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