Download Chlorogenic Acid

TOMATOES
tomatoes
Tomatoes
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herbaceous perennials
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Lycopersicon esculentum or Solanum
lycopersicum
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part of the Solanaceous (nightshade) family
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same family as potatoes and eggplants
Tomatoes were first domesticated in Mexico
Tomatoes and tomato products are a large part of the
vegetables consumed by Americans
US is the second largest producer of tomatoes
Tomatoes are a good source of:
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vitamin C
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vitamin A (as beta-carotene)
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protein (in seeds)
Phytochemicals in tomatoes
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p. coumaric acid
lycopene
chlorogenic acid
beta-carotene
flavonoids
quercetin
Lycopene
C40H56
Lycopene
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The most abundant pigment in ripe tomatoes
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80 – 90% of all pigments
Most tomatoes contain 3 to 5 mg/100g raw
material
Located in chloroplast of fruit and thylakoid
membrane of photosynthetic pigment-protein
complexes
Lycopene
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Exists as trans-isomer in nature
Can isomerize to mono or poly-cis form from:
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Heat
Light
Certain chemical reactions
Most efficient singlet oxygen and ROS
scavenger of known carotenoids
Lycopene: Heath Benefits
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Good antioxidant activity due to extended
system of conjugated double bonds
Has ability to trap peroxyl radicals
May reduce threat of CVD by:
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Reduction of inflammation
Inhibition of cholesterol synthesis
Lycopene: Health Benefits
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Antioxidant properties show anticancer effects
by :
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Preventing the growth of prostate cancer cells
Inhibiting anti-androgen
Decreases endogenous DNA strand breakages in
lymphocytes of humans
Lycopene: Health Benefits
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Increased serum lycopene levels have shown
inversely correlated relationship with many
types of cancer, such as:
Oral cavity
Esophagus
Stomach
Colon
Rectal
Pancreas
Bladder
Breast
Lycopene: Bioavailability
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Highly variable and affected by several
factors:
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Molecular linkage
Food matrix the lycopene is part of, and particle
size of lycopene containing food
Amount of lycopene consumed in meal
Levels of dietary fiber, fats, proteins and other
carotenoids consumed at the same time
Lycopene: Bioavailability
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More bioavailable in cooked, finley grated or
processed form of tomato products
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Due to the release of lycopene from the tomato
tissue matrix and disruption of plant cell walls and
lycopene-protein complexes
Heat in processing can convert trans to cis
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Cis-isomer less likely to aggregate and crystalize.
Cis-isomer more soluble in bile acids and other
lipophilic solutions.
Cis-isomer more easily transported in tissue and cell
matrices.
Lycopene: Bioavailability
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Lycopene absorption hindered when ingested
with dietary fiber or high-methoxyl petin.
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Due to the promotion of a highly-viscous condition
in the dietary tract.
Chlorogenic Acid
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Acts as an antioxidant in plants and protects
against degenerative, age-related diseases in
animals when supplied in their diet.
Is the major soluble phenolic in Solanaceous
species such as potato, tomato and eggplant.
Also accumulates to substantial levels in
apples, pears, plums and coffee.
Chlorogenic Acid
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Can limit low-density lipid (LDL) oxidation,
the major determinant of the initial events in
atherosclerosis
Removes particularly toxic reactive species by
scavenging alkylperoxyl radicals and may
prevent carcinogenesis by reducing the DNA
damage they cause
Chlorogenic Acid
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High bioavailability
Antioxidant potential of CGA is probably
more accessible than that of many flavonoids
Can be absorbed directly by the small intestine
but most CGA is absorbed in the large
intestine by esterases of the gut microflora to
release caffeic acid
Research in Tomatoes
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Gene silencing proved HQT to be the principal
route for accumulation of CGA in solanaceous
species.
Over expression of HQT in tomato caused
plants to accumulate higher levels of CGA
Showed improved antioxidant capacity and
resistance to infection by a bacterial pathogen.
Beta-carotene
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Orange colored member of the carotenoid family.
Fat soluble compound found in many fruits and
vegetables.
Second most abundant carotenoid in tomatoes after
lycopene.
Dimer of vitamin-A
Beta-carotene: Health benefits
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Conversion into retinol by the body.
Studies relating beta-carotene with reduction in
macular degeneration, anti-aging, cataract,
asthama, heart and AIDS have been done in past.
Natural antioxidant
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free radical quenching,
singlet oxygen scavenging and
lipid antioxidant capacity
Potential anticancer agent (?)
Beta-carotene: Health benefits
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Supplemental beta-carotene have been shown to
increase lung cancer incidents among smokers.
(Omenn et al, 1996 and, alpha-tocopherol beta-carotene study, 1994)
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Synthetic and all-Trans beta-carotene have been
predicted to cause increased risk of cancer. (BenAmotz et al, 1998)
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A natural diet rich in carotenoids may actually
reduce the risk of lung or other cancer. (Holick et al,
2002)
Beta-carotene: Tomatoes
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Beta-carotene accounts for 20-35% of total
carotenoids in tomatoes. (Kmiecik & Liciewska, 2000)
Some of the factors that may effect the betacarotene content in tomato are
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type of cultivars,
stage of maturation of tomato fruit,
method of processing
storage
Transgenic tomatoes
Beta-carotene: Effect of cultivar type
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In a study done on 18 different variety of
tomato beta carotene content ranged
from 0.28 mg/100gm (1447) to 1.00
mg/100gm (Poly 20) among the different
lines.
Reporting of higher beta-carotene in
tomato was done by Kmiecik &
Liciewska (2000) in a study of six
different cultivars at an average of 1.31
mg/100g. Significant difference among
cultivars was noticed.
Source: Frusciante et al, 2007 )
Beta-carotene: Stage of growth of fruit
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Quantify the carotenoid pigments during the
growth of tomato fruit after flowering was done
by Nobuyuki & Friedman (2003) .
Beta-carotene (1.2±0.1 g/100g) was only detected
after the 50th day of flowering.
Beta-carotene: Effect of processing
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Lin & Chen (2005) worked on evaluating
effect of three different heat treatments
tomatoes on the final beta-carotene.
Hot break screened tomato juice was
subjected to
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90C for 5 min prior to canning,
Boiled in water at 100C for 30 min after
canning and
HTST done at 1210C for 40 sec before canning.
No significant difference was observed.
Beta-carotene: Effect of processing
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Amount of beta-carotene
decreased continuously over
time when stored at 30±20C
without preservative, the
tomato soup with sodium
benzoate showed
significantly reduced losses.
Beta-carotene, mg/100gm
14
12
No Preservative
10
Sodium Benzoate
8
6
Percent decrease
(No Preservative)
4
Percent decrease
(Sodium Benzoate)
2
0
0
15
30
45
60
Storage period, days
Source: Vashista, A. et al 2003. Figure generated using data presented
(Vashista et al, 2003)
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Beta-carotene content in
Micra RS cultivar of tomato
reduced from 1.37 to 0.69
mg/ 100g at -200C and 0.96
at -300C, when stored for 12
months. (Lisiewska & Kmiecik,
2000)
(Source: Lisiewska & Kmiecik, 2000)
p. coumaric acid
p. coumaric acid
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para-coumaric acid
There two other isomers: o-coumaric acid and mcoumaric acid also, but p-coumaric acid is found
most often in nature
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Wikipedia information about Coumaric acid
Where is p. coumaric acid found?
Tomatoes
Peanuts
Carrots
Garlic
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Wikipedia information about Coumaric acid
Health benefits of
p. coumaric acid
p. coumaric acid inhibits the
development of stomach cancer
by using its antioxidant properties to interfere
with the development of cancer-causing
nitrosamines in the stomach
Where are nitroamines found?: pickled food and cured meats
J Biochem Mol Toxicol
p. coumaric acid decreased oxidative
damage to DNA
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Also decreased COX-2 overexpression of
colon mucosal cells in rats
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Prevented inflammation of the colon mucosal
cells
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Scandanavian Journal of Gastroenterology
p. coumaric acid “acts as an
antioxidant in the colonic mucosa
in vivo.”
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p. coumaric acid significantly induced GSTM2 (a phase II enzyme) expression in the
colon
implies antioxidant activity
“significantly decreases the basal level of the
oxidative damage of DNA.”
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British Journal of Nutrition
p. coumaric acid may be able to
inhibit gluconeogenesis
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Gluconeogenesis is the homeostatic process in which
the liver utilizes amino acids (from tissues) to create
glucose for use as energy.
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May have implications for blood glucose control in
diabetic patients.
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Patients with insulin-resistant diabetes undergo
gluconeogenesis even though their blood glucose levels are
high because the glucose can not get into tissues and the
body thinks it is starving.
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J Biochem Mol Toxicol
P. coumaric acid has also been
shown to inhibit platelet aggregation
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in humans by interfering with the arachodonic
acid clotting cascade
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makes blood less viscous and easier to pass
through vessels.
has tremendous promise in prevention of vascular
disease
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Thrombosis Center, University of Florence
Cancers prevented by
phytochemicals in tomatoes
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Prostate
Breast
Oral
Stomach
Colon
Rectal
Pancreatic
Bladder
Lung
Additional health benefits of
tomatoes
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chlorogenic acid
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shown to decrease LDL oxidation
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Decreases the likelihood of atherosclerosis
p. coumaric acid
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shown to inhibit gluconeogenisis
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has implications for glucose control in diabetics
interferes with the arachodonic acid clotting
cascade
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may decrease the likelihood of vascular disease
Health benefits (cont’d)
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Beta-carotene
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shown to decrease the likelihood of macular
degeneration
Lycopene
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May be linked with prevention of cardiovascular
disease by decreasing the cholesterol synthesis
pathway.
Lowers risk of prostate, breast, and many other
types of cancers
Efficient singlet oxygen and ROS scavenger
References
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[1] Burri, B. J. Beta-carotene and human health: a review of current research. Nutrition research. 17-3, 547-580.
[2] Frusciante, L., Carli, P., Ercolano, M.R., Pernice, R., Matteo, A.D., Fogliano, V. and Pellegrini, N. 2007.
Antioxidant nutritional quality of tomato. Molecular nutrition food research. 51, 609-617.
[3] The alpha-tocopherol, beta carotene cance prevention study group. The effect of vitamin E and beta carotene on
the incidence of lung cancer and other cancers in male smokers. New England J of medicine. 1994. 330, 1029-35.
[4] Omenn, G.S., Goodman, G.E., Thornquist, M.D., Balmes, J., Cullen, M.R., Glass, A., Keogh, J.P., Meyskens,
F.L., Valanis, B., Williams, J.H., Barnhart, S. and Hammar, S. 1996. Effects of a combination of beta carotene and
vitamin A on lung cancer and cardiovascular disease. The New England J of medine. 334, 1150-1155.
[5] Ben-Amotz, A., Yatziv, S., Sela, M., Greenberg, A., Rachmilevich, B., Shwarzman, M and Weshler, Z. 1998.
Effect of natural beta carotene supplementation in children exposed to radiation from the Chernobyl accident.
Radiation environment biophysics. 37, 187-193.
[6] Holick, C.N., Michaud, D.M., Solomon, R.S., Mayne, S.T., Pietinen, P., Taylor, P.R., Virtamo, J and Albanes, D.
2002. Dietary carotenoids, serum beta-carotene, and retinol and rish of lung cancer in the alpha-tocopherol, betacarotene chohort study. American J of epidemiology. 156, 536-547.
[7] Kmiecik, W. and Liciewska, Z. 2000. Morphology and composition of tomato cultivars. Nahrung. 44, 349-353.
[8] Nobuyuki, K. and Friedman, M. 2003. Tomatine, chlorophyll, beta-carotene and lycopene content in tomatoes
during growth and maturation. J of the science of food and agriculture. 83, 195-200.
[9] Lin, C.H. and Chen, B.H. 2005. Stability of carotenoids in tomato juice during processing. European food research
technology. 221, 274-280.
[10] Vashista, A., Kwatra, A. and Sehgal, S. 2003. Effect of storage time and preservatives on vitamin and pigment
contents of canned tomato soup. Plant foods for human nutrition. 58. 1-6.
[11] Lisiewska, Z. and Kmiecik, W. 2000. Effect of storage period and temperature on the chemical composition and
organoleptic quality of frozen tomato cubes. Food Chemistry. 70, 167-173.
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