For the plants that contain them, polyphenols help protect against sunlight damage (from ultraviolet radiation), deter herbivores, prevent microbial infections, and provide pigmentation (color). And for us humans, polyphenols play a number of important roles as well. Even though polyphenols aren’t considered essential nutrients, numerous lines of evidence—from epidemiological studies, human trials, animal models, and mechanistic studies—suggest that polyphenols play a huge role in protecting against cancer, heart disease, diabetes, asthma, osteoporosis, neurodegenerative diseases, and other conditions associated with oxidative stress. In fact, a major reason foods like red wine and olive oil (as well as diets rich in both, such as the Mediterranean diet) show up as so beneficial may be due to their high polyphenol content! Along with chronic diseases, supplementing with polyphenols has been shown to protect against infections and reduce the signs of aging.
Polyphenols exert their most potent effects by acting as antioxidants—preventing cellular damage by neutralizing hazardous oxygen radicals and improving cellular health as a result (which, in turn, benefits virtually every system in the body). As a result of their antioxidant properties, polyphenols also boost the immune system and protect against both chronic and acute diseases. In addition, polyphenols can help regulate enzyme function, stimulate cell receptors, modulate the functions of inflammatory cells (including T and B lymphocytes, macrophages, platelets, and natural killer cells), alter adhesion molecule expression, affect nerve cells and cardiac muscle cells, and exert antiviral effects.
In fact, a 2013 study showed that overall mortality was reduced by 30% in participants who ate a diet rich in polyphenols (greater than 650 milligrams/day) as compared with participants who had low polyphenol intakes (less than 500 milligrams/day). For reference, fruits and vegetables typically contain 200 to 300 milligrams per 100-gram serving. In fact, apples are the main source of polyphenols in the American diet.
Polyphenols can be divided into subclasses based on chemical structure, including flavonoids, phenolic acids, flavonolignans, lignans, stilbenoids, tannins, chalcones, and curcuminoids.
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Flavonoids (also called bioflavonoids) are a diverse group of polyphenols (including more than 6,000 plant metabolites!) that may help reduce inflammation, exert antibacterial properties, and protect against heart disease and certain cancers. Although flavonoids have a range of different health effects, their benefits seem to be primarily due to helping regulate cell-signaling pathways (rather than by acting as antioxidants, which is a perk many phytonutrients offer).
Flavonoids can be classified into seven major classes: flavones, flavanones, flavonols, flavanonols, isoflavones, flavanols (also called flavan-3-ols) and anthocyanidins/anthocyanins.
Flavones are a class of flavonoids with anticancer and anti-inflammatory properties. They include apigenin, luteolin, chrysin, and baicalein, and are most abundantly found in spices and red or purple fruits and vegetables—particular parsley, thyme, and celery.
Apigenin (very high in all parts of the celery plant—including seeds and heart, along with parsley, oregano, vine spinach, and chamomile) has antimicrobial activity against a number of potential pathogens. Chrysin (found in propolis and honey, as well as carrots, chamomile, and mushrooms) has been shown to interfere with the effects of dietary fructose at the intestinal level, along with reducing intestinal inflammation. And baicalein, found in the roots of a Chinese herb called Scutellaria baicalensis, has been shown to powerfully inhibit biofilm formation in Candida albicans, while also enhancing gut barrier function, and supporting a healthy, diverse gut microbiome.
Flavanones are a type of phytonutrient found abundantly in citrus fruit (and to a lesser degree, tomatoes and some herbs such as mint), and most notably include hesperidin (the main flavanone in sweet oranges), naringin (which gives grapefruit its bitter taste), and morin (found abundantly in strawberries).
Although more research in humans is needed, studies suggest flavanones in general are powerfully cardio-protective and may also reduce risk of other degenerative diseases, such as cancer. These compounds have been shown to reduce inflammation, reduce hypertension, lower blood lipids, increase insulin sensitivity, and exert antioxidant properties. In the gut, flavanones interact with and influence the microbiota, and these interactions may be responsible for many of the biological effects of flavanones.
Flavonols can offer major disease protection by potentially increasing plasma antioxidant capacity, decreasing lymphocyte (a type of white blood cell) DNA damage, increasing activity of an antioxidant enzyme called erythrocyte superoxide dismutase, and decreasing urinary markers of oxidative damage. Flavonols include the cancer- and cardio-protective phytonutrients kaempferol (which can interrupt the growth of a variety of cancers, reduce cardiovascular disease mortality, and protect against diabetes), myricetin (which can protect cells from carcinogenic mutations and protect neurons from oxidative stress while also inhibiting the activity of some viruses), and quercetin (which may suppress inflammation in the brain and promote a healthy gut barrier).
Rich sources of flavonols include onions, apples, chives, tomatoes, broccoli, cherries, kale, leeks, and pears.
Flavononols are another subgroup of flavonoids and includes genistein, taxifolin, engeletin, and astilbin. All of these compounds are metabolized by the gut microbiota, although more research is needed to discern the connection between the impact of flavononols on the gut and their subsequent host benefits (including their anti-inflammatory properties and their ability to modulate fat and carbohydrate metabolism).
The richest sources are grapes and wine, but flavononols can also be found in macadamia nuts, nectarine, onions, prickly pear, tamarind, sorrel and anise.
Isoflavonoids (including isovlavones, isoflavanes, pterocarpans, and retenoids) and their derivatives are considered phytoestrogens, due to the fact that many of these compounds exert biological effects via estrogen receptor (as well as other biological activities that inhibit the synthesis of enzymes involved in estrogen metabolism). In general, isoflavonoids have antioxidant, antiproliferative, antimutagenic, antimicrobial, and cancer-preventative effects, particularly against hormone-related cancers (like prostate cancer, endometrial cancer, and breast cancer). The isoflavones daidzein, genistein, glycitein, formononetin, and daidzin are metabolized by the gut microbiota (particularly Clostridium and Eubacterium), and the subsequent metabolites appear responsible for the beneficial effects of soybeans found in some studies.
Most isoflavonoids are found in the Fabaceae family, which includes legumes such as soy.
Anthocyanidins and Anthocyanins
Anthocyanidins and anthocyanins appear to have anti-inflammatory, antidiabetic, anticancer, cardioprotective and neuroprotective effects and may even have pain-relieving properties due to an affinity for certain “pain-sensation” cell membrane receptors in the brain. Highly related, anthocyanins are glycosides whereas anthocyanidins are aglycones.
Anthocyanidins are uniquely and specifically capable of both crossing the blood-brain barrier and localizing in areas of the brain involved in learning and memory (e.g. hippocampus). In addition, they have powerful anti-oxidant and anti-inflammatory properties, which is important since oxidative stress and inflammation are thought to be key contributors to cognitive impairment.
Anthocyanins are said to exert neuroprotective effects through functioning as an antioxidant (induce the production of phase II detoxifying and antioxidant enzymes), promoting calcium homeostasis, by acting as anti-inflammatory agents and by inhibiting neuronal apoptosis. Anthocyanins have been associated with upregulation of phase II antioxidant and detoxifying enzymes and also with the restoration of p53 gene expression. Anthocyanins also have immunomodulatory effects, helping to increase the production of anti-inflammatory cytokines. This is linked to their ability to inhibit tumor formation. Benefits are mediated via anti-oxidant and anti-inflammatory effects, positive effects on plasma lipid levels, and modulation of glucose metabolism and endothelial function. Anthocyanins contribute to eye health; both in vitro and in vivo studies have shown their benefits in several areas including the protection of retinal cells, improved microcirculation, modulation of retinal enzyme activity, and accelerated resynthesis of rhodopsin.
These flavonoids give many fruits and vegetables a beautiful blue, purple, or deep red color (think: grapes, red cabbage, cherries, eggplant, blueberries, cranberries, raspberries, and blackberries!).
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Flavanols, also called flavan-3-ols, and not to be confused with flavonols (with two o’s!) occur in two forms: catechins and proanthocyanidins (also known as condensed tannins). Flavanols play an important role in vascular health by supporting normal blood flow and maintaining the elasticity of blood vessels, and they may also have antimicrobial, anticancer, and neuro-protective properties.
Catechins help regulate blood pressure, support weight loss, enhance the activity of antioxidant enzymes, and exhibit neuroprotective activity. Catechins are found in many types of fruit (apricots are the richest source) as well as red wine and green tea, and proanthocyanidins give certain foods and beverages their astringency—including wine, tea, grapes, peaches, berries, pears, and bitter chocolate.
Proanthocyanidins are condensed tannins with demonstrated anti-cancer, antioxidant, anti-diabetic, anti-inflammatory, anti-arthritis, neuroprotective, and antimicrobial properties. They also appear to protect against some eye diseases. Proanthocyanidins are found in apples, cinnamon, cocoa beans, blueberries, hazelnuts, sorghum, apples, pears, grapes, grape seeds, red wines, cranberry, black currants, maritime pine bark, black tea, and green tea; the highest concentrations are found in coca beans. Red Delicious and Granny Smith are the highest among the apples.
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In addition to flavonoids, non-flavonoid polyphenols play some important roles. Non-flavonoids include flavonolignans, lignans, stilbenoids, tannins, chalcones, and curcuminoids.
Tannins are astringent phytonutrients sometimes considered “antinutrients” due to their ability to bind protein and iron. But they actually offer a host of benefits for human health by serving as antioxidants, reducing blood pressure, improving blood lipids, and offering antimicrobial activity. Some tannins can benefit dental health by combating harmful oral bacteria and inhibiting plaque formation.
Wine and tea are some of the best-known sources of tannins, but other items include pomegranates, berries, nuts, persimmons, legumes, and certain herbs and spices (cloves, cumin, vanilla, cinnamon, tarragon, and thyme).
Stilbenes aren’t found in very high quantities in most foods, but one particular stilbene—resveratrol—had repeatedly shown up in the scientific literature as having strong anticancer properties. Along with its antioxidant effects, resveratrol can thwart all three stages of cancer development (initiation, promotion, and progression) by modulating the pathways involved in cell division, cell growth, cell death, inflammation, angiogenesis (the development of new blood vessels), and metastasis (the spread of tumors). Resveratrol is a major reason why red wine (and the grapes it’s made from) is strongly disease protective: the richest source is grape skins!
Other stilbenes, like rhapontigenin, pinosylvin, and pterostilbene (an analog of resveratrol and the main antioxidant in blueberries), are also being explored for their potential to protect against (or fight existing) cancer, neurological diseases, inflammation, diabetes, heart disease, and stroke. In fact, pterostilbene is emerging as a possible therapy for Alzheimer’s disease!
Coumarins are a family of polyphenol benzopyrene chemicals with anti-inflammatory, antioxidant, anticoagulant, antithrombotic, vasodilatory, antimicrobial (antiviral, antifungal, and antiparasitic), anticancer, antidiabetic, analgesic, and neuroprotective properties. At least 1300 different coumarins have been identified, many with strong pharmacological activity, in conjunction with low toxicity and few side effects, that make them excellent drug candidates. In fact, the blood thinners warfarin and coumadin are both coumarin compounds, as is the antibiotic Novobiocin and the anti-aggressive drug Batoprazine. The high coumarin content of Cassia cinnamon is why it can be toxic in large quantities, causing blood clotting problems that can result in bruising and nose bleeds, in addition to hepatotoxicity.
Lignans are found abundantly in flax seeds and sesame seeds and in smaller amounts in broccoli, kale, apricots, cabbage, and Brussels sprouts.
After we eat lignan precursors, our intestinal bacteria convert them into enterolignans called enterodiol and enterolactone, which have a steroid structure and can mimic some behaviors of estrogens, categorizing them as phytoestrogens. Although more research is needed, enterolignans have the potential to protect against hormone-associated cancers (breast cancer, ovarian cancer, prostate cancer, and uterine cancer) by blocking the action of true estrogens. Other studies suggest a role for lignans in reducing inflammation, improving glycemic control, combatting viruses, and protecting against heart disease, but we need more research and better-controlled human trials to clarify whether lignans are responsible versus other components of plant foods. Lignans are related to the fiber class lignin, both being polyphenolics derived from lignols, but while lignans tend have a low molecular weight (often dimers), lignins are highly polymerized hence their behavior as a plant fiber.
Flavonolignans are composed of a phenylpropane unit (coniferyl alcohol) and a flavonoid unit (taxifolin), and have demonstrated a number of health properties across studies. For example, they help modulate various cell-signaling properties, inhibit arachidonic acid metabolism (resulting in lower formation of pro-inflammatory mediators), and even inhibit platelet aggregation, making them potentially helpful for cardiovascular disease. A number of flavonolignans have been isolated from the milk thistle plant, most notably silybin, but also silychristin and silydianin.
Chalcones give a yellow or orange color to foods and have a range of important biological activities that could benefit our health. For example, they’ve demonstrated antioxidant, antimicrobial, anti-cancer, anti-inflammatory, and immunosuppressive effects in a range of studies. These phytonutrients may be particularly valuable in fighting cancer, as they’ve been shown to interfere with all stages of carcinogenesis (initiation, promotion, progression, angiogenesis, invasion, and metastasis), as well as helping regulate cell cycle progressions to favor apoptosis of transformed cells. In vitro, different chalcones have exhibited cytotoxic effects against different cancer cells, making them particularly useful in developing anti-cancer drugs. Chalcones also have antimicrobial activity, including against methicillin-resistant Staphylococcus aureus (MRSA). Found in citrus fruits, apples, tomatoes, shallots, bean sprouts, potatoes, fingerroot, and licorice.
Curcuminoids are natural compounds found in turmeric, primarily consisting of curcumin, demethoxycurcumin, and bisdemethoxycurcumin. Although all three have demonstrated health-protective effects, some studies show synergistic activity that makes these curcuminoids more active when combined (i.e., consuming turmeric) than when taken individually, especially when it comes to reducing cancer cell viability.
The best-studied curcuminoid is curcumin (technically known as diferuloylmethane). It was first discovered about 200 years ago by researchers who isolated the “yellow-coloring matter” from the turmeric rhizome, and named it curcumin. This compound has potent anti-inflammatory effects that make it comparable to pharmaceutical NSAIDs; in fact, studies have been done comparing curcumin to phenylbutazone in rheumatoid arthritis patients and people healing from hernia surgery, and found the curcumin was just as effective as the NSAID treatment. It works by helping regulate a number of transcription factors, protein kinases, adhesion molecules, cytokines, and enzymes involved in inflammatory processes. There’s also evidence that curcumin works as a cyclooxygenase (COX)-2 inhibitor by acting at the transcriptional level and possibly posttranslational level. It happens to be a powerful antioxidant as well, demonstrating an ability to reduce lipid peroxidation by supporting antioxidant enzymes (such as superoxide dismutase, catalase, and glutathione peroxidase), which play an important role in regulating lipid peroxidation. There’s also some in-vitro evidence that curcumin can scavenge oxygen free radicals (like superoxide anions and hydroxyl radicals) and nitric oxide involved in the initiation of lipid peroxidation. Other studies show that curcumin may have antibacterial activity, as well as the potential to lower LDL cholesterol and triglycerides (and improve the HDL/total cholesterol ratio). It’s been shown to boost brain-derived neurotrophic factor, which may play a role in combatting neurodegenerative diseases and depression. A number of studies also suggest it may inhibit tumor proliferation, making it a potentially useful adjunct to cancer treatment. Apart from all that, curcumin has strong (and somewhat complicated!) effects on the immune system. It can play a role in the activation of T cells, B cells, macrophages, neutrophils, natural killer cells, and dendritic cells, making it an important immune modulator.
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