Richard Beliveau, Ph.D. and Denis Gingras, Ph.D. See book keywords and concepts | Daily anthocyanidin intake may attain 200 milligrams in enthusiastic berry eaters, making these compounds one of the most frequently ingested classes of polyphenols.
High anthocyanidin content, which includes proanthocyanidins (see below), may be responsible for the very strong antioxidant potential found in berries. As seen in Table 13, of all the fruits analyzed, blueberries are in first place, closely followed by raspberries, strawberries, and cranberries, and far ahead of most of the fruits and vegetables that form a regular part of our daily diet. | Erich Grotewold See book keywords and concepts | Japanese morning glory dusky mutants displaying reddish-brown or purplish-gray flowers are deficient in a novel glycosylation enzyme for anthocyanin biosynthesis, UDP-glucose: anthocyanidin 3-O-glucoside-2"-0-glucosyltransferase, due to 4-bp insertions in the gene, Plant J 42: 353-363.
Napoli, C, Lemieux, C. and Jorgensen, R., 1990, Introduction of a chimeric chalcone synthase gene into petunia results in reversible co-suppression of homologous genes in trans, Plant Cell 2: 279-289. Nesi, N., Debeaujon, I., Jond, C, Pelletier, G., Caboche, M. and Lepiniec, L. | | ANR, which is closely related in sequence to dihydroflavonol reductase (DFR) as well as the phenylpropanoid and isoflavonoid enzymes, cinnamoyl-CoA reductase, cinnamoyl alcohol dehydrogenase, and vestitone reductase, converts the product of ANS/LDOX, an anthocyanidin, to a 2,3-c«-2R,3R-flavan 3-ol (Figure 3.3). | | Role of anthocyanidin reductase, encoded by BANYULS in plant flavonoid biosynthesis, Science 299: 396-399. Xu, W., Shioiri, H., Kojima, M., and Nozue, M., 2001, Primary structure and expression of a 24-kD vacuolar protein (VP24) precursor in anthocyanin-producing cells of sweet potato in suspension culture, Plant Physiol 125: 447-455. | | The
C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity. Bioorg Med Chem Lett 13: 3853-3857. Turnbull, J. J., Nakajima, J. I., Welford, R. W., Yamazaki, M., Saito, K., and Schofield, C. J., 2004,
Mechanistic studies on three 2-oxoglutarate-dependent oxygenases of flavonoid biosynthesis, J Biol
Chemll9: 1206-1216.
Veit, M., and Pauli, G. F., 1999, Major flavonoids from Arabidopsis thaliana leaves, J Nat Prod 62: 1301-1303.
Vogt, T. | | Structure and mechanism of anthocyanidin synthase from Arabidopsis thaliana, Structure 10: 93-103. Winkel-Shirley, B., 2001a, Flavonoid biosynthesis: a colorful model for genetics, biochemistry, cell biology and biotechnology, Plant Physiol 126: 485-493. Winkel-Shirley, B., 2001b, It takes a garden. How work on diverse plant species has contributed to an understanding of flavonoid metabolism, Plant Physiol 127: 1399-1404. Xie, D. Y., Sharma, S. B., Paiva, N. L., Ferreira, D., and Dixon, R. A. | Thomson Healthcare, Inc. See book keywords and concepts | Antiulcer activity of an'anthocyanidin from Vaccinium myrtillus. Arzneimittelforschung; 38: 686-690. 1988
Mertz-Nielsen A, Munck LK, Bukhave K et al. A natural flavonoid, IdB 1027, increases gastric luminal release of prostaglandin E2 in healthy subjects. Ital J Gastroenterol; 22:288-290. 1990
Morazzoni P & Bombardelli E. Vaccinium myrtillus. Fitoterapia; 48(l):3-29. 1995
Morazzoni P & Magistretti MJ. Activity of Myrtocyan®, an anthocyanoside complex from Vaccinium myrtillus (VMA), on platelet aggregation and adhesiveness. Fitoterapia; LXI (1): 13-21. 1990
Morazzoni P & Magistretti MJ. | Marshall Editions See book keywords and concepts | Eat plenty of fruits such as blueberries and dark cherries, which contain anthocyanidin, a chemical that is also important for good eye health. Foods rich in magnesium and chromium, such as brewer's yeast, kelp, leafy greens, and apples, have beneficial effects on glaucoma.
Supplements: Some studies have shown that magnesium can dilate blood vessels and improve vision; take 250 mg twice a day. Taking 1,000 mg of vitamin C two to four times a day can significantly reduce elevated intraocular pressure in cases of glaucoma. | | Fruits such as blueberries and dark cherries contain anthocyanidin, a chemical that is also important for good eye health. Vitamin C is also found in these foods, which is helpful for building up the structures around the eye. Avoid any foods that can cause or contain free radicals. These include saturated fats, hydrogenated fats and oils or partially hydrogenated fats and oils, sugar, alcohol, and charred or grilled meats.
Supplements: Take 15 mgof lutein with a meal. Lutein is an antioxidant in the carotenoid family, which can benefit the part of the retina where macular degeneration occurs. | by Michael Murray, N.D. and Joseph Pizzorno, N.D. See book keywords and concepts | | The vibrant red color of strawberries is due to the anthocyanidin known as pelargonidin.
Strawberries' unique flavonoid content makes them a valuable protector against inflammation, cancer, and heart disease. The anti-inflammatory properties of strawberries include the ability of their flavonoids to lessen the activity of the enzyme cyclooxygenase, or COX. Nonsteroidal anti-inflammatory drugs (NSAIDs), such as aspirin and ibuprofen, block pain by blocking this enzyme, which is linked to inflammatory conditions such as rheumatoid arthritis, osteoarthritis, asthma, atherosclerosis, and cancer. | Phyllis A. Balch, CNC See book keywords and concepts | Phytochemicals: anthocyanidin, avicularin, coumarin, hyperoside, methyl salicylate, quercetin, rutin, salicin, salicylic acid, vanillin.
Tightens tissues and promotes elimination of excess fluid. Reduces inflammation and strengthens and tones the system. Good for colds, flu, nausea, digestive disorders, muscle cramps and aches, and diarrhea.
The word aspirin is derived from an old name for this plant, spirea. | David Hoffman, FNIMH, AHG See book keywords and concepts | Anthocyanins and Anthochlors
There are two main classes of flavonoid pigments that provide flower color:
Anthocyanins (red to blue colors)
Anthochlors, including chalcones and aurones (yellow petal colors)
The most common anthocyanidin (anthocyanin aglycone) is cyanidin. The other 15 known anthocyanidins, 6 of which are widely distributed, differ only in the number and position of methoxyl or hydroxyl groups. The gly-cosidal anthocyanins are incredibly numerous; cyanidin alone is found in 76 different glycosidic combinations. | James F. Balch, M.D. and Mark Stengler, N.D. See book keywords and concepts | The bioflavonoid anthocyanidin fights free radicals and helps keep the collagen around the eye healthy and flexible. Blueberries and cherries are excellent sources.
Drink a glass of clean water every two waking hours to flush out toxins and to keep the eye tissues supple. Spread your consumption of water and other liquids out across the day, so that you do not build up pressure in your eye.
Some studies have shown fish oils to lower eye pressure. Incorporate fatty fish such as salmon, mackerel, and cod into your meals two or three times a week. | Bryan Hanson, PhD See book keywords and concepts | Delphinidin, discussed in Chapter 3, is another example of an anthocyanidin (see Figure 3.11). Note that pro-anthocyanins are a type of tannin and are discussed under that heading.
Coumarins
Simple Coumarins
Coumarins are a widely distributed group of molecules with a variety of medicinal uses. Coumarin, a compound in its own right, shows the basic ring structure characteristic of the group. Aesculin, a glycoside isolated from the bark of the common horse chestnut (Aesculus hippocastanum), acts as a vascular protective agent. | Michael T. Murray, N.D. See book keywords and concepts | Widely used pharmaceutical preparations in Europe are standardized for anthocyanidin content (typically 25 percent). The following doses should be taken three times daily:
Anthocyanosides (calculated as anthocyanidin): 20-40 milligrams Bilberry extract (25 percent anthocyanidin content): 80-160 milligrams
Toxicity
Extensive toxicological investigation confirms that bilberry anthocyanoside extracts are devoid of toxic effects. Rats administered doses as high as 400 milligrams per kilogram showed no apparent side effects, and excess levels were quickly excreted through the urine and bile. | Richard Beliveau, Ph.D. and Denis Gingras, Ph.D. See book keywords and concepts | We have discovered that delphinidin, an anthocyanidin present in blueberries, has the capacity to inhibit the activity of the VEGF receptor associated with angiogenesis, at concentrations close to those occurring in food. It is interesting to observe that this activity is probably not related to the antioxidant potential of delphinidin: malvidin, a very similar compound also found in large quantities in blueberries, possesses antioxidant activity equal to that of delphinidin, but displays no ability to interfere with the receptor. | Erich Grotewold See book keywords and concepts | Petunia (Brugliera et al., 1994). Abbreviations: UDPG flavonoid 3 or 7-glucosyltransferase (UF3GTor UF7GT); anthocyanin rhamnosyltransferase (RT). enzymes that function in secondary pathways, information that is clearly important for efforts to engineer the chemical and biological characteristics of flavonoids and other metabolites.
4.3. Flavonoid Acetyltransferases
Although acetylation of flavonoids has been known for some time, it is less common and not as well understood as the other modifications. | by Michael Murray, N.D. and Joseph Pizzorno, N.D. See book keywords and concepts | | This is a natural reaction of their anthocyanidin pigments and does not make the food item unsafe to eat.
QUICK SERVING IDEAS
• Add Vi cup of fresh or frozen blueberries to your favorite smoothie recipe.
• Fresh or dried blueberries add a colorful and nutritious punch to cold breakfast cereals.
• Layer yogurt and blueberries in wineglasses and top with crystallized ginger.
• Use blueberries as a filling for breakfast crepes.
• Mix blueberry jam with savory spices to make a spread that is delicious on baked fish or chicken.
SAFETY
Blueberries contain moderate levels of oxalates. | Linda B. White, M.D. See book keywords and concepts | The Rid-of-'Roids Diet
Foods rich in fiber and in proanthocyanidin and anthocyanidin, two compounds that improve the health of blood vessels, can help prevent future hemorrhoids and help current ones heal. Blackberries, blueberries, and cherries are among the foods that contain these ingredients. If constipation is a factor, you may want to consider a fiber supplement, such as psyllium seed husks (1 tablespoon per day) mixed with water or juice. If your diet is less than healthy, add a good multivitamin to ensure that you're getting all of the important blood-vessel-healing nutrients. | Michael T. Murray, N.D. See book keywords and concepts | Cherries, hawthorn berries, blueberries, and other dark red-blue berries are rich sources of anthocyanidin and proanthocyanidin. These flavonoid molecules give the fruits their deep red-blue color, and are remarkable in their ability to prevent collagen destruction. Flavonoid-rich grape seed and hawthorn extracts are the best herbal recommendations for gout.
Hemorrhoids
Hemorrhoids are basically varicose veins of the rectum. They may be near the beginning of the anal canal (internal hemorrhoids) or at the anal opening (external hemorrhoids). | C. P. Khare See book keywords and concepts | The principal pigment is dracocarmin, an anthocyanidin. Another pigment, dracorubin has also been reported.
Use in Western herbal
Doses of 600 mg to 1.8 g were formerly given as an astringent in diarrhoea and allied ailments, but officially it is not being used internally, and is regarded as inert.
Dracaena terminalis or Chinese Colli yields Chinese Dragon's blood. It is used in dysentery and diarrhoea, and as a diaphoretic. Known as Xue jie over-the-counter. | Josef A. Brinckmann and Michael P. Lindenmaier See book keywords and concepts | C00CH3
/r0H
Salicylic acid methyl ester
U
(= Methyl salicylate) as violanthin), including quercitrin, luteolin, luteolin-7-glucoside, rutin (= vio-laquercitrin), the C-glucosides vitexin and isovitexin (8-C- and 6-C-glucosyla-pigenin, respectively), vicenin 2 and violanthin (6,8-di-C- and 6-C-rhamno-syl-8-C-glucosylapigenin), orientin and isoorientin (8-C- and 6-C-glucosyllute-olin), scoparin, saponarin and saponare-tin [2, 3]. anthocyanidin glycosides and carotenoids occur as well, including violaxanthine with four geometrical isomers [4] and zeaxanthin, among others. | Mark Blumenthal See book keywords and concepts | Antiulcer activity of an anthocyanidin from Vaccinium myrtillus. Arzneimittelforschung 1988;38:686-90.
Marcollet M, Bastide P, Tronche P. Angina protecting effect of Vaccinium myrtillus anthocyanosides aimed at the release of lactate dehydrogenase (LDH) and of its cardiac isoenzymes in the rat subjected to a swimming test. C R Seances Soc Biol Fil 1970;163:1786-9.
Martin-Aragon S, Basabe B, et al. Antioxidant action of Vaccinium myrtillus L. Phytother Res 1998; 12:S 104-6.
Martinelli E, Scilingo A, Pifferi G. | The Life Extension Editorial Staff See book keywords and concepts | The genus Vaccinium comprises nearly 200 species of berries, all showing generous amounts of flavonoid/ anthocyanidin compounds. Bilberry, Vaccinium myrtillus fructus, has historically been used in various eye conditions, including glaucoma, cataracts, macular degeneration, diabetic retinopathy, and retinitis pigmentosa. Although bilberry is not considered a curative herb in regard to glaucoma treatment, it appears to assist in halting additional damage by btinging a good flow of blood to the eyes. | Michael T. Murray, N.D. See book keywords and concepts | The following doses should be taken three times daily:
Anthocyanosides (calculated as anthocyanidin): 20-40 milligrams Bilberry extract (25 percent anthocyanidin content): 80-160 milligrams
Toxicity
Extensive toxicological investigation confirms that bilberry anthocyanoside extracts are devoid of toxic effects. Rats administered doses as high as 400 milligrams per kilogram showed no apparent side effects, and excess levels were quickly excreted through the urine and bile.1754
References
1. Grieve M: A Modern Herbal, Vol. 1. Dover Publications, New York, 1971, pp. 385-386.
2. |
Textbook of Natural Medicine 2nd Edition Volume 1Michael T. Murray, ND See book keywords and concepts | | Widely used pharmaceutical preparations in Europe are typically standardized for a 25% anthocyanidin content. Dosages are as follows:
• anthocyanosides (calculated as anthocyanidin): 20-40 mg three times/day
• Vaccinium myrtillus (25% extract): 80-160 mg three times/day
• fresh berries: 55-115 g three times/day.
TOXICOLOGY
Extensive toxicological investigation has demonstrated that V. myrtillus anthocyanoside extracts are devoid of toxic effects. | Michael T. Murray, N.D., Joseph E. Pizzorno, N.D. See book keywords and concepts | The standard dose for bilberry extracts is based on its anthocyanoside content, as calculated by its anthocyanidin percentage. Widely used pharmaceutical preparations in Europe are standardized for anthocyanidin content (typically twenty-five percent). These extracts are also available in the United States. The standard dose is 80 to 160 mg three times per day. | Michael T. Murray, N.D. See book keywords and concepts | For analytical purposes, the anthocyanoside content should always be expressed in terms of anthocyanidin. Only very small amounts of free anthocyanidins exist in nature and in bilberry extracts.
History and folk use
Bilberries have, of course, been used as food and for their high nutritive value. Medicinally, they have been utilized in the treatment of scurvy and urinary complaints (including infection and stones).1
The dried berries have been used primarily for their astringent qualities in the treatment of diarrhea and dysentery. |
Textbook of Natural Medicine 2nd Edition Volume 1Michael T. Murray, ND See book keywords and concepts | | An extract with an anthocyanidin content of 25% actually contains about 37% anthocyanosides due to the conjugation of the anthocyanidin with a glycoside. (For analytical purposes, the
GENERAL DESCRIPTION
CHEMICAL COMPOSITION
O — Glyc.
Anthocyanin
R
R'
R"
Delphinidin 3-O-glycoside
OH
OH
OH
Cyanidin 3-O-glycoside
OH
OH
H
Petunidin 3-O-glycoside
OH
OH
OCH3
Peonidin 3-O-glycoside
OCH3
OH
H
Malvidin 3-O-glycoside
OCH3
OH
OCH3
Figure 118.1 Structures of V. myrtillus anthocyanins2 Glyc. |
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