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
Production
Country
(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
p-coumaric acid
– Phenylpropanoids

– Aromatic secondary metabolites COOH

benzoic acid
– Substitution with carboxyl or
hydroxyl groups generate a
bundle of compounds
COOH
transcinnamic acid
 Phytochemicals
• Ellagic Acid and derivatives

EA-4-
arabinoside

EA-4-
acetylarabinoside

EA-4-
acetylxyloside

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
CO OH OH
HO
HO O
CO
OH O
HO CO
HO CO HO
O
HO
HO HO

HHDP Ellagic acid

Formation of ellagic acid (Shi and others 2005)

 Phytochemicals
• Carotenoids
– Lipid soluble compounds

– Present in most plants

– Red to yellow colors

CH3 H3C OH
H3C CH3 CH3

Lutein
CH3
CH3 CH3 CH3
HO CH3
CH3
CH3 CH3 CH3
H3C

Beta-carotene CH3
CH3 CH3 CH3
H3C
 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 HO OH
Essential in biological functions

– Important content of Vitamin C in strawberry

 Phytochemicals
• Vitamin C comparison
Fruit Fiber Potassium Vitamin C Sugar
(g) (mg) (mg) (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

HO O

Quercetin-rutinoside (Rutin) OH

Quercetin-glucoside OH O Quercetin

Quercetinglucuronide OH

Kaempferol-glucuronide HO O

OH
OH O
Kaempferol

(Seeram and others 2006)

 Phytochemicals
• Anthocyanins

– Flavonoids
• Flavan-3-ol

– water-soluble pigments

– brightly colored
• Strawberry
• Blueberry R1
3'
• Grape R2
4'
+
R7 O
5' R3
7

R6 6 5
3 R4
(Seeram and others 2006)
R5
 Phytochemicals OH
+ B
HO O
A C
• Anthocyanins 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 Reference
(Fresh fruit)
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

Anthocyanins 5256 mg/kg Aaby and others 2007

 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 Breast cancer cells

Seeram & others, 2006

 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
• Bagchi D, Sen CK, Bagchi M, Atalay M. 2004. Anti-angiogenic, Antioxidant, and Anti-carcinogenic
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
• 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