Chapter 22
Health Benefits of Edible Berry Anthocyanins: Novel Antioxidant and Anti-Angiogenic Properties 1
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Shirley Zafra-Stone , Manashi Bagchi , and Debasis Bagchi
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InterHealth Research Center, 5451 Industrial Way, Benicia, C A 94510 Creighton University Medical Center, 2500 California Plaza, Omaha, NE 68178 2
Edible berries provide for some of the richest sources of anthocyanins and antioxidants. Numerous studies have substantiated why consumption of anthocyanin-rich fruits and vegetables might retard or prevent the onset of chronic diseases. The therapeutic and pharmacologic potential of berry anthocyanins demonstrate significant chemoprotective, anti -platelet aggregation, anti-angiogenic and anti-cancer properties. A significant number of studies have discovered that berry anthocyanins are novel cardioprotectant, beneficial in reducing age-associated oxidative stress, improving neuronal and cognitive brain function as well as ocular health, and protecting genomic integrity. Anthocyanin derivatives exhibit a broad spectrum of pharmacologic, therapeutic and medicinal properties including antioxidative, anti-bacterial, anti-viral, anti-hypertensive and anti-angiogenic effects. Furthermore, anthocyanins enhance immune system and detoxification, and modulate cholesterol biosynthesis. Edible berry anthocyanins have been shown to inhibit cellular transformation and this study demonstrates the potent inhibitory effect on inducible V E G F expression. Overall, anthocyanin-rich fruits and vegetables and their constituents favorably regulate a number of mechanistic pathways to promote human health and to prevent diseases.
© 2007 American Chemical Society
Shahidi and Ho; Antioxidant Measurement and Applications ACS Symposium Series; American Chemical Society: Washington, DC, 2007.
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338 Anthocyanins are known to exhibit some of the strongest therapeutic effects of any phytochemical, and have been used as a viable therapy for disease prevention and health promotion. During the past two decades a growing number of studies have investigated the diverse medicinal and protective abilities of anthocyanins present in various fruits and vegetables. In vitro, in vivo and human clinical studies have shown that berries possess many biological functions that confer potent health benefits including cardiovascular and neurological health, blood sugar support, anti-aging, anti-inflammatory and anti cancer properties, urinary tract health, healthy vision and dermal health. In the United States, daily intake of anthocyanins in humans has been estimated to be 180-215 mg/day, which is much higher than the intake (23 mg/day) of other flavonoids (1,2). O f all the antioxidants, anthocyanins have shown their ability to penetrate into cell membranes, enhance and demonstrate therapeutic benefits. Main therapeutic benefits attributable to anthocyanins include antioxidant cytoprotection and maintaining genomic D N A integrity. Numerous studies have linked anthocyanin activity to an increase in peripheral circulation, improved vision, enhanced immune systems, and wound healing. Anthocyanins also serve as anti-inflammatory, antibacterial and anti-mutagenic agents, and provide cardioprotection by mamtaining vascular permeability. Chemistry and Bioavailability of Berry Anthocyanins Anthocyanins, a sugar or acid form of anthocyanidins, are powerful natural antioxidants of the flavonoid family. Anthocyanins represent a large group of water-soluble plant pigments of the 2-phenylbenzophyrylium (flavylium) structure (Figure 1) (1). The anthocyanin class consists of approximately 200 or more compounds chemically combined with a sugar moiety such as glucose, rhamnose, galactose, xylose and arabinose (3). The positively charged oxygen atom in the anthocyanin molecule makes it a more potent hydrogen-donating antioxidant compared to other flavonoids (4). Berry anthocyanins are one of the most important group of plant pigments visible to the human eye. Anthocyanins differ from other natural flavonoids in the range of blue to red colors imparted by the anthocyanins and by their ability to form resonance structures dependent largely upon the changes in p H (5,6). At p H 1-3 the flavylium cation is red colored, at p H 5 the colorless carbinol pseudo base (pb) is generated, and at p H 7-8 the blue purple quinoidal base (qb) is formed (7,8). Consumption of natural polyphenolic-enriched foods including strawberries, spinach or red wine has been shown to increase the serum antioxidant capacity in humans (10). The serum total antioxidant capacity was assessed following consumption of strawberries (240 g), spinach (294 g), red wine (300 ml) or vitamin C (1250 mg) in 80 elderly women using different assay techniques including oxygen radical absorbance capacity (ORAC) assay, Trolox equivalent antioxidant capacity (TEAC) assay and ferric reducing antioxidant potential (FRAP) assay. The results showed that the total antioxidant capacity of serum determined as O R A C , T E A C and F R A P , using the area under the curve,
Shahidi and Ho; Antioxidant Measurement and Applications ACS Symposium Series; American Chemical Society: Washington, DC, 2007.
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Ri H Ri = OH Ri = OH
R2
Ri = OCH3
R =H
R^OCHa R^OCHa
R = OH R = OCH
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=
: Pelargonidin : Cyanidin
H R =H R = OH =
2
: Delphinidin : Peonidin : Petunidin
2
2
2
2
3
: Malvidin
Figure 1. Chemical Structure of Anthocyanins.
increased significantly by 7-25% during the 4-h period following consumption of red wine, strawberries, vitamin C or spinach. The total antioxidant capacity of urine showed that O R A C increased (/?
