citrus phytochemicals - texas a&m university
TRANSCRIPT
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CitrusPhytochemicals
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Designer Foods
Functional Foods
Hypernutritious Foods
Nutraceuticals
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Nutraceuticals
Nutraceuticals is a generic descriptionof food composites containing naturaland biologically active phytochemicals
with disease-preventing and life-sustaining functions alone or in
combination.
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Chemopreventive agents
• Micronutrients–vitamins, beta carotene,
molybdenum, calcium• Phytochemicals• Synthetics
–vitamin derivatives–piroxicam–tamoxifen
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Phytochemicals
• Carotenoids• Indole• Saponins
• Coumarins• Dietary Fiber• Isoflavones• Protease
inhibitors
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Phytochemicals
• Organosulfides• Isothiocynates• Indoles• Dithiolthiones
• Polyphenols• Flavonoids• Tannins• Folic acid
Contd.
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Chemopreventive agents(Based on their mechanisms of action)
• Blocking agents• Suppressing agents
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CANCER CHEMOPREVENTIVE AGENTS
1. BLOCKING AGENTS -- prevent carcinogens from reaching or reacting with the DNA, the genetic information.
2. SUPPRESSIVE AGENTS -- inhibit the expression of cancer in cells that have already been exposed to a carcinogen.
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Cancer Producing Compounds
Blocking Agents
Cells Attacked By Cancer Producing Compounds
Suppressing Agents
Cancer Wattenburg, 1993
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Chemopreventive agents
• Blocking agents– Flavonoids– Indoles– Isothiocynates– Diallyl sulfides– D-limonene
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MECHANISM OF ACTION (BLOCKING AGENTS)
1. Inhibit the formation of the active carcinogen.
2. Increase the rate at which the active carcinogen is inactivated.
3. Act as scavengers for the active forms of carcinogens.
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Chemopreventive agents
• Suppressing agents–D-limonene–Diallyl sulfides– vitamin D–vitamin A and retinoids–monoterpenes–carotenoids– polyphenols
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Anticarcingenic mechanisms
• Antioxidant effects
• Increased activity of enzymes thatdetoxify carcinogens
• Effect on cell differentiation• Blocked formation of nitrosamines• Altered estrogen metabolism• Decreased cell proliferation• Maintenance of normal DNA repair
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THREE-PHASE MECHANISM FOR CHEMICAL CARCINOGENESIS
1. INITIATION - normal cells to latent tumor cells.
2. PROMOTION - latent tumor cells to carcinoma in situ.
3. PROGRESSION - carcinoma in situ to invasive carcinoma.
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Initiation
Promotion
Phase I enzymes
Oxidative damageFree radicals
Lycopene, Lutein,Zeaxanthin and Beta carotene
Procarcinogens
CarcinogensElectrophiles
DNA Damage
Phase II enzymesGlutathione S-transferase
LimonoidsFlavonoids
Tumor
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• Carotenoids– Lycopene -Prostate Cancer– Beta carotene– Lutein and zeaxanthin-Blindness– Beta cryptoxanthin
Health Promoting Compounds
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Carotenoid Concentrations• Lycopene- Grapefruit
– 3362 ug/100 g wet wt (Mangels etal.,1993)
– 350 ug/100 g wet wt (Gross et al., 1987)
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Carotenoid Concentrations(ug/100g)
Carotenoids Oranges PinkGrf
WhiteGrf
Mandarins Lemons
Beta Carotene 39 1310 14 38 3
AlphaCarotene
20 0 1 20 0
Lutein +Zeaxanthin
14 0 10 20 12
Lycopene 0 3362 0 0 0
BetaCryptoxanthin
149 0 0 106 0
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Clinton, 1998. Nutrition Reviews 56(2):35-51.
Food Lycopene content mg/100g
Tomato (fresh) 0.88-4.20
Grapefruit (raw pink) 3.36Tomato (cooked) 3.7
Tomato (sauce) 6.2
Tomato Paste 5.40-150.00
Tomato soup, condensed 7.99Tomato Powder, drum or spray
dried112.63-126.49
Tomato Juice 5.00-11.60
Guava (fresh) 5.4Watermelon 2.3
Papaya (fresh) 2.00-5.30Ketchup 9.90-13.44
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Lycopene Variation Among Texas Grapefruits
Star R
ubyI-4
8
Rio R
ed
Ray R
uby
Hender
son
Ruby Red
Thomso
n Pin
k
Marsh
White
Duncan W
hite0
2
4
6
8
10
12
14ppm
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Beta carotene
Star Rubya
I-48b
Hendersonbc
Rio Redcd
Ray Rubyd
Ruby Rede
Thomsonf
Marshg
Duncang
0
2
4
6
8
10ug/g fresh wt
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Texasa
Floridab
02468
10121416
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Beta carotene
Lycopene
Florida
Texas
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LIMONOIDS WITH ANTICANCER ACTIVITY
• Limonin• Limonin 17-ß-D-glucopyranoside• Limonin carboxymethoxime• Deoxylimonin
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INACTIVE LIMONOIDS
• Limonol• Deoxylimonic acid• Ichangensin• 17,19-didehydrolimonoic acid• Nomilinic acid 17-ß-D-glucopyranoside
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LIMONOIDS WITH PARTIAL ACTIVITY
• Nomilin• Nomilin 17-ß-D-glucopyranoside• Obacunone
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EPIDEMILOGICAL EVIDENCE
1. oral cavity. 5. pancreas.2. larynx. 6. lung.3. esophagus. 7. colon.4. stomach. 8. rectum.
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LIMONOID GLUCOSIDES
1. Tasteless.2. Soluble in water.3. Human consumption (already pre- sent in citrus and citrus products in relatively high concentrations).4. Can be prepared from by-products of juice processing plants (seeds and citrus molasses).
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Limonoid Concentrations
• Limonoid glucosides– Limonin 17-beta D-glucopyranoside
(54-180 ppm)– Oranges-320 ppm– Grapefruit -195 ppm– Lemon-90 ppm
• LG 1000
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• Anticarcarcinogenic activities (Lam and
Hasegawa, 1989; Lam et al., 1989, 1994;
Miller et al., 1989; Gutherie et al., 1997,
1998)
• Act as natural pest control agents (Alford et
al., 1986; Klocke and Kubo, 1987)
• Excellent chemotaxonomic markers
(Hasegawa and Ifuku, 1994)
Biological Activity of Citrus Limonoids
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O
O
O
O
O
O
O
O
O
O
O
O
OAc
O
O
O
O
O O
CH2OH
OHHO
OHCOOH
OO
O
OH
COOH
-Glucose
O
O
O
OAc
COOH
Limonin Nomilin
Obacunone Glucoside Noimilinic acid Glucoside
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Cancer cells used (MTTmethod)
• The HL-60 (human leukemia cancer)• SKOV3 (human ovary cancer)• Hela (human cervical cancer cells)• BGC-823 (human stomach cancer)• Bel-7402 (human liver cancer)• MCF-7 human breast cancer cell
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Effect of different limonoids on the percentage ofviability MCF-7 cells affected by limoniods.
Limonoid concentrations
0 20 40 60 80 100 120 140
Per
cent
age
of v
iabi
lity
of M
CF
-7 h
uman
bre
ast c
ance
r ce
lls
-20
0
20
40
60
80
100
120
Nomilin Limonin Glucoside mixture Nomilinic acid glucosideObacunone glucoside
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Foods with cancer preventative properties
Incr
easi
ng im
port
ance Garlic
CabbageLicorice
Soybeans GingerUmbelliferae
(carrots, celery, parsnips)
Onions Tea TurmericCitrus (orange, lemon, grapefruit)
Whole Wheat Flax Brown RiceSolanacae (tomato, eggplant, peppers)
Cruciferous (broccoli, cauliflower, Brussels sprouts)
Oats Mints Oregano CucumberRosemary Sage Potato Thyme Chives
Cantaloupe Basil Tarragon Barley Berries
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• Flavonoids- Breast cancer andheart diseases–Naringin–Hesperetin
Health Promoting Compounds
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Antioxidant Activity• Reactive oxygen Species (ROS) play major role many diseases. To counteract ROS and prevent their possible damage to biological molecules all oxygen-consuming organisms have antioxidant systems.• Antioxidant enzymes: superoxide dismuatase, catalase, and glutathione peroxidase.
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Total Antioxidant capacity
• ORAC- Oxygen RadicalAbsorbance Capacity can bemeasured by COBAS FARA IIanalyzer
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ORAC of commercial orange juice and vitamin C from juice
Wang et al., 1996. J. Agric. Food Chem. 14(3):701-705.Juice Vit. C Juice Vit. C Juice Vit. C Juice Vit. C Juice Vit. C
0
5
10
15
20ORAC (micromoles Trolox eq./ml)
Grape Grapefruit Tomato Orange Apple
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Antioxidant Activity of Fruits
Wang et al., 1996. J. Agric. Food Chem. 14(3):701-705.
Strawberry Plum Orange Grapefruit Grapefruit Tomato Grape Grape0
20
40
60
80
100
120
140
160ORAC (micromoles of Trolox equvivalents/g of dry matter)
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Pectin• Used traditionally for jelly preparation• Modified pectin can prevent prostate cancer• Pectin can reduce levels of serum cholesterol
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How much we need?
• To consume about 6g of pectinonly about 170 g of grapefruitpulp is sufficient (Baker, 1994)
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Apples 0.71-0.84Apricots 0.71-1.32Bananas 0.59-1.28Beans 0.27-1.11Blackberries 0.68-1.19Carrots 1.17-2.92Cherries 0.24-0.54Dewberries 0.51-1.00Grapes 0.09-0.28Grapefruit 3.30-4.50Lemons 2.8-2.99Loganberries 0.59Oranges 2.34-2.38Raspberries 0.97Squash 1.00-2.00
Pectin Content in Different Fruits (% fresh wt)
Baker, 1997
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Dietary Fiber
Dietary fiberdenotes all plantcell wallcomponents thatcannot bedigested by ananimal’s ownenzymes.
• Pectin• gums• lignin• Cellulose• Hemicellulose• pentosans
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Citrus Pectin Health Benefits• Modified Citrus Pectin (MCP) prevent
cancer metastasis, inhibiting cancer cellproliferation
• Hypoglycemic Effect• Hypocholesterolemic Effect• Hemostasis• Modulate human immune function• Detoxification
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Steps in the process of tumor dissemination
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Schematic representation of aggregation of tumorcell to normal cell and pectin function
Raz and LOtan, 1987
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Probable mechanism of pectinhypocholesterol effect
Farnandez, et al., 1990
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Pectin HypocholesterolemicAction
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Pectin HemostasisFunction
Pectin can shorten the coagulationtime of blood and act as anantagonist of heparin when injectedintravenously.
Pectin sulfate can behave as stronganticoagulant.
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Parts of the citrus fruit which contain pectin
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Components of Pectin• Molecular Weight
• Polygalacturonic Acid• Galacturonic Acid Content• Methoxyl Esters• Neutral Sugar Content
• Ions• Proteins
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Structure of Pectin
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•••••
•••••
•••••••
Linear galacturonan
Side ChainRhamnogalacturonan
Structure of Pectin
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Modified Citrus Pectin
• Mol Wt should be less than 10 KD
• MC should be less than 8%
• Galactose and uronic acid may enhance
the effect
• Higher Mol Wt and higher MC increase
its hypocholesterol effect.
Pienta et al., 1995; Briggs 1997
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Fibroblast Growth FactorSignaling System
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Factor-Receptor
• Cell needs to communicate to eachother.
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• Fibroblast growth factor (FGF) isubiquitous and a mediator ofdevelopmental processes in theembryo and homeostasis.
• Inappropriate FGF signaltransduction may contribute todefect, tumor growth,cardiovascular disease, diabetes,etc.
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Components of FGF
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• FGF factor, currently 19 geneproducts)
• FGF receptor, (Transmembranetyrosine kinases) currently 4 geneproducts
• Heparan sulfate proteoglycans(FGFRHS)
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FGFR FGF
FGFR
FGF FGFR
FGF
FGFR FGF
Stimulation
Inhibition
No StimulationNo Inhibition
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Inhibitors (Heparin Mimics)
• Suramin• Suramin analogs
• pentosan polysulfate• Carrageenans• Dextran• Dextran derivatives
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FPLC Elution Profile
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Variation of Pectin Contentand Composition inDifferent Citrus Species
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0.00
1.00
2.00
3.00
4.00
5.00
6.00
lem tan org gra
F/A L
Ext
ract
ion
Rat
e (%
of
fres
h w
eigh
t)
Pectin Extraction Rate in Different Citrus Species
d a b cb bba
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Changes of Pectin Contentand Composition Due to
Harvest Season
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0
1
2
3
4
5
6
Aug Sep Nov Jan Mar May
F A L
Pectin Extraction RateE
xtra
ctio
n R
ate
(% o
f fr
esh
wei
ght)
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0
20
40
60
80
100
120
140
160
180
200
Aug Sep Nov Jan Mar May
F A L
mg/
g of
Pec
tin
Wei
ght
Variation of Pectin Sugar Content
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0
10
20
30
40
50
60
70
Aug Sep Nov Jan Mar May
rhamnose arabinose xylosemannose galactose glucose
Per
cent
age
(% o
f to
tal s
ugar
wt.
)
Harvest Month
Variation of pectin sugar composition
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In Vitro Effects ofCitrus Pectin on the
FGF SignalingSystem
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Spec
ific
bou
nd (
% o
f co
ntro
l)
Pectin Concentration (µg/ml)
Pectin Inhibit FGF-1 Binding to FGFR1
-20
0
20
40
60
80
100
0 3 30 300
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0
20
40
60
80
100
120
0 0.001 0.01 0.1 1 10
Pectin Added Heparin Only
% o
f M
axim
um B
indi
ng
Heparin Concentration (µg/ml)
Pectin Inhibit FGF-1 Binding to FGFR1
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Autoradiography of pectin inhibition activity
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-0.2
0
0.2
0.4
0.6
0.8
1
Lemon Grapefruit Tangerine Orange
Citrus Species
Flavedo/Albedo Lamella
Inhibition activities of pectin
Inhi
bitio
n A
ctiv
ity
c a a aa a bb
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0
0.2
0.4
0.6
0.8
1
AUG SEP NOV JAN MAR MAY
F A L
Inhibition activities of pectinIn
hibi
tion
Act
ivity
a
a a ab
a
a a a a b ab a a b a a bc a a ab
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Foods with cancer preventative properties
Incr
easi
ng im
port
ance Garlic
CabbageLicorice
Soybeans GingerUmbelliferae
(carrots, celery, parsnips)
Onions Tea TurmericCitrus (orange, lemon, grapefruit)
Whole Wheat Flax Brown RiceSolanacae (tomato, eggplant, peppers)
Cruciferous (broccoli, cauliflower, Brussels sprouts)
Oats Mints Oregano CucumberRosemary Sage Potato Thyme Chives
Cantaloupe Basil Tarragon Barley Berries
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Case Control and Cohort Studiesof All Types of CancerFruit No. of studies
Inverse PositiveVegetables 55 9
Fruits 29 5
Tomatoes 35 10
Carrots 50 7
Citrus Fruit 26 6
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Phytochemicals in Fruits and Vegetables to Improve Human Health
Project Director: Bhimu PatilCollaborators:
Drs. L.M.Pike, D. R. Lineberger, W. L. McKeehan, Rosemary Walzem E. G. Miller, G. B. Cobb, K.E. Dooley, N. Turner, Lisa Appelt,
and M. Skaria, Texas A&M University SystemDr. G.D. Stoner, Ohio State University
Dr. J. W. Fahey, Johns Hopkins UniversityDr. I. G. Goldman, Univ. of Wisconison
Dr. J. Heimendinger, AMC Cancer Research CenterDr. Fred Kachik, Univ. of Maryland
Dr. M. Farooqui, University of Texas, Pan-American
College Station, Kingsville, Weslaco, Lubbock, Houston, Dallas,Stephenville,
Start date: Spring 2001 http:// Phytochemicals.tamu.edu
Dr. Gene Lester, USDA-ARS WeslacoDr. Clare Hasler, University of Illionois