Phytochemicals in
Strawberry
Jorge Cardona
Chris Duncan
Jaiprakash Patil
Outline
Introduction
Mechanisms
Phytochemical profile
Health Benefits
Introduction
Strawberry is an accessory fruit
Strawberries belong to the Rosaceae family
Perennial herb stimulated by
winter weather
Introduction
U.S. is the main strawberry producer in the
world
California and Florida (main productive
regions)
U.S., Spain, Korea, Japan and Mexico
(USDA 2005)
Introduction
Country
Production
(1000 tonnes)
Egypt
100.0
Germany
146.5
Italy
146.8
Japan
196.2
Korea
202.0
Mexico
128.9
Morocco
118.6
Poland
184.6
Russia
217.0
Spain
308.0
Turkey
200.0
United States
1,053.2
Table 1. World’s main strawberry production countries (FAO statistics 2005).
Mechanisms
• Antioxidant Capacity
Scavenging of reactive oxygen species (ROS) by flavonoids (Pietta 2000)
Mechanisms
• Metal Chelation
– Entrapment of metals
– Two or more binding
sites
– Catechol and galloyl
moieties
OH
OH
OH
HO
OH
Binding sites for trace metals (Pietta 2000)
Phytochemicals
• Phenolic Acids
HO
COOH
– Phenylpropanoids
– Aromatic secondary metabolites
p-coumaric acid
COOH
benzoic acid
– Substitution with carboxyl or
hydroxyl groups generate a
bundle of compounds
COOH
transcinnamic acid
Phytochemicals
• Ellagic Acid and derivatives
EA-4arabinoside
EA-4acetylarabinoside
EA-4acetylxyloside
Ellagic acid glycosides (left), Ellagitannin (right) Sanguiin H-6 (Mullen and others 2003; Lei 2002)
Phytochemicals
• Ellagic Acid and derivatives
HO
OH
OH
OH
O
HO
HO
CO
O
HO
CO
CO
HO
OH
OH
OH
CO
HO
O
HO
O
HO
HO
HHDP
Formation of ellagic acid (Shi and others 2005)
HO
Ellagic acid
Phytochemicals
• Carotenoids
– Lipid soluble compounds
– Present in most plants
– Red to yellow colors
CH3
H3 C CH3
HO
H3C
CH3
CH3
CH3
CH3
CH3
CH3
Beta-carotene
CH3
H3 C
OH
CH3
Lutein
CH3
CH3
CH3
H3 C
CH3
CH3
CH3
Phytochemicals
• Omega 3 fatty acids
– Fatty acids with three or more double bonds
– ALA, EPA, DHA
– Important to human health (cell signaling, membrane
fluidity)
H3C
COOH
Alpha-linolenic acid (ALA)
Phytochemicals
• Vitamin C
HO
– Ascorbic acid
O
O
HO
Water soluble vitamin
Potent antioxidant
Essential in biological functions
HO
– Important content of Vitamin C in strawberry
OH
Phytochemicals
• Vitamin C comparison
Fruit
Fiber
(g)
Potassium Vitamin C
(mg)
(mg)
Sugar
(g)
Strawberries
3
210
84
7
Apples
4
150
7
14
Grapes
1
266
6
22
Bananas
4
504
13
17
Oranges
3
252
74
13
Phytochemicals
• Vitamin C
– Recommended intake
90 mg/day (male)
75 mg/day (female)
– Content in 147g of strawberry
(8 medium strawberries)
96mg of Vitamin C
Phytochemicals
• Flavonols
OH
– The flavonols present in strawberries are:
OH
O
HO
Quercetin-rutinoside (Rutin)
Quercetin-glucoside
Quercetinglucuronide
Kaempferol-glucuronide
OH
OH
O
Quercetin
OH
O
HO
OH
OH
O
Kaempferol
(Seeram and others 2006)
Phytochemicals
• Anthocyanins
– Flavonoids
• Flavan-3-ol
– water-soluble pigments
– brightly colored
• Strawberry
• Blueberry
• Grape
R1
3'
R2
4'
+
R7
O
5'
7
R6 6
5
R3
3 R4
R5
(Seeram and others 2006)
Phytochemicals
+
O
HO
A
• Anthocyanins
OH
B
C
OH
OH
– The major anthocyanins are glycosylated
• Pelargonidin 3-glucoside is predominant
– 83% of total anthocyanins on average
• Pelargonidin 3-rutinoside (8%)
• Cyanidin 3-glucoside (7%)
(Seeram and others 2006)
Phytochemicals
• Structures of pigments found in strawberry
Anthocyanin aglycones
5-carboxypyranopelargonidin 3-glucoside
anthocyanin-flavanol condensed pigments
(Andersen and others 2004)
Phytochemicals
• What makes flavonoids good antioxidant?
– Structural arrangement of chemical bonds
• Hydroxy groups on phenolic rings
• Specific Oxygen Bonds
• Specific double bonds
OH
OH
HO
O
OH
OH
O
Phytochemicals
• The Power of Anthocyanins…
• The “French Paradox”
Phytochemicals
• Phytochemical summary
Phytochemical
Concentration
(Fresh fruit)
Reference
Phenolic Acids
85 mg/kg
Aaby and others 2007
Total Ellagic Acid
293 mg/kg
Aaby and others 2007
Carotenoids
260 μg/kg
Marinova and Ribarova 2007
ω-3 Fatty Acids
292 mg/kg
Couture and others 1988
Vitamin C
1041 mg/kg
Koplotek and others 2005
Flavonols
13 mg/kg
Aaby and others 2007
5256 mg/kg
Aaby and others 2007
Anthocyanins
Health Benefits
• Inhibition of H2O2 induced VEGF
Vascular Endothelial Growth Factor
Bagchi & others, 2004
Health Benefits
• Anti-angiogenic Activity
New blood vessel formation
Bagchi & others, 2004
Health Benefits
• Bioactivity Index
• Realties antioxidant activity and
antiproliferative activity
Sun & others, 2002
Health Benefits
• Effect of Anthocyanins on Lung Hemorrhage
Rossi & others, 2003
Health Benefits
• H2O2 Induced Cytotoxicity
Heo & Lee, 2005
Health Benefits
• H2O2 Induced Membrane Damage
Heo & Lee, 2005
Health Benefits
• Strawberry Antiproliferative Activity
Meyers & others, 2003
Health Benefits
• Anti-proliferative Activity of Fruits
Sun & others, 2002
Health Benefits
• Inhibition of Proliferation of Colon Cancer Cells
Seeram & others, 2006
Health Benefits
• Inhibition of Proliferation of Prostate & Breast
Cancer Cells
Prostate cancer cells
Seeram & others, 2006
Breast cancer cells
Health Benefits
• Inhibition of Proliferation of Prostate & Breast
Cancer Cells
Seeram & others, 2006
Health Benefits
• Cervical & Breast Cancer Inhibition
Törrönen & Määttä, 2002
Other Health Benefits
• Platelet function & cardiovascular health1
• Platelet activation reduced
• Oxidative stress & aging2
• Strawberry retards the affects oxidative stress
• age-related neurodegenerative diseases??
• Esophageal & colon cancer3
• Positive correlation with consumption of
freeze dried berries
1
Rechner & Kroner, 2005
2 Joseph & others, 2000
3 Stoner & others, 2007
Conclusion
• The main compounds in strawberry
–
–
–
–
Anthocyanins
Ellagitannins
Phenolic Acids
Vitamin C
• These contribute to a significant AOX
• Numerous Studies on Health Benefits
– Cancer
Questions?
References
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Bagchi D, Sen CK, Bagchi M, Atalay M. 2004. Anti-angiogenic, Antioxidant, and Anticarcinogenic Properties of a Novel Anthocyanin-Rich Berry Extact Formula. Biochemistry
(Moscow) 69(1):75-80.
Meyers KJ, Watkins CB, Pritts, MP, Liu RH. 2003. Antioxidant and Antiproliferative Activities of
Strawberries. J Agric Food Chem 51:6887-92.
Sun J, Chu Y-F, Wu X, Liu RH. 2002. Antioxidant and Antiproliferative Activities of Common Fruits.
J Agric Food Chem 50:7449-54.
Seeram NP, Lee R, Scheuller HS, Heber D. 2006. Identification of phenolic compounds in
strawberries by liquid chromatography electrospray ionization mass spectroscopy. Food Chem
97:1-11.
Rossi A, Serraino I, Dugo P, Di Paola R, Mondelo L, Genovese T, Morabito D, Dugo G, Sautebin L,
Caputi AP, Cuzzocrea S. 2003. Protective Effect of Anthocyanins from Blackberry in rat Model of
Acute Lung Inflammation. Free Radical Research. 37(8):891-900.
Heo JH, Lee CY. 2005. Strawberry and Its Anthocyanins Reduce Oxidative Stress-Induced
Apoptosis in PC12 Cells. J Agric Food Chem 53:1984-9.
Törrönen R, Määttä K. 2002. Bioactive substances and health benefits of strawberries. Acta
Horticulturae 567:797-801.
Stoner GD, Wang L-S, Zikri N, Chen T, Hecht SS, Huang C, Sardo C, Lechner JF. 2007. Cancer
prevention with freeze-dried berries and berry components. Cancer Biology 17:403-10.
Joseph JA, Denisova NA, Bielinski D, Fisher DR, Shukitt-Hale B. 2000. Oxidative stress protection
and vulnerability in aging: putative nutritional implications for intervention. Mechanisms of
Ageing and Development 116:141-153.
References
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Rechner AR, Kroner C. 2005. Anthocyanins and colonic metabolites of dietary polyphenols inhibit
platelet function. Thrombosis Research. 116:327-34.
USDA. 2005. Fruit and tree nuts outlook. Economic Research Service. US Department of
Agriculture
FAO 2005. World strawberry production. FAO statistics (online). Available at:
http://faostat.fao.org/
Pietta PG. 2000. Flavonoids as antioxidants. J Nat Prod 63:1035-42
Lei Z. 2002. Monomeric ellagitannins in oaks and sweetgum. Dissertation. Virginia Polytechnic
Institute and State University
Mullen W, Yokota T, Lean ME, Crozier A. 2003. Analysis of ellagitannins and conjugates of ellagic
acid and quercetin in raspberry fruits by LC-MSn. Phytochemistry 64:617-24
Shi B, He Q, Yao K, Huang W, Li Q. 2005. Production of ellagic acid from degradation of valonea
tannins by Aspergillus niger and Candida utilis. J Chem Technol Biotechnol 80:1154-9
Seeram NP, Lee R, Scheuller HS, Heber D. 2006. Identification of phenolic compounds in
strawberries by liquid chromatography electrospray ionization mass spectroscopy. Food Chem
97:1-11
Marinova D, Ribarova F. 2007. HPLC determination of carotenoids in Bulgarian berries. J Food
Comp Ana 20:370-4
Aaby K, Wrolstad RE, Ekeberg D, Skrede G. 2007. Polyphenol composition and antioxidant
capacity in strawberry purees; Impact of achene level and storage. J Agric Food Chem 55:5156-66
Klopotek Y, Otto K, Bohm V. 2005. Processing strawberries to different products alters contents
of vitamin C, total phenolics, total anthocyanins and antioxidant capacity. J Agric Food Chem
53:5640-6
Courture R, Willemot C, Avezard C, Castaigne F, Gosselin A. 1988. Improved extraction of lipids
from strawberry. Phytochem 27(7):2033-6