by Santosh, Yafei, Magnet. Introduction. The world’s largest fruit crop, with approximately 65 million metric tons produced annually. (. Mazza. 1995). Total . of 1610 phytochemical compound record (. ID: 549263
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Phytochemicals in Grape
by Santosh, Yafei, Magnet
Slide2Introduction
The world’s largest fruit crop, with approximately 65 million metric tons produced annually. (Mazza 1995)Total of 1610 phytochemical compound record (Pezzuto 2008)
Slide3Introduction
LuteinLycopeneCatechinResveratrolAnthocyaninZeaxanthinQuercetinMelatonin
Slide4Resveratrol
Slide5Resveratrol
Resveratrol is a naturally occurring polyphenolic phytoalexin A potent antioxidant (Cadenas and Barja, 1999) Potentially benefits Cancer Cardiovascular disease and other diseases Both in vivo and in vitro (Bradamante and others 2004, Pezzuto 2008, Afaq and others 2003, Sengottuvelan and others 2006, Jang and others 1997)
Slide6Cardiovascular
disease
Slide7Cardiovascular disease
The cardioprotective effect of resveratrol in humans has yet to be demonstrated
(Bradamante and others 2004)
Slide8Cardiovascular disease
In vitro and in vivo studies on animal model It may provide protection by a number of mechanisms Inhibition of (LDL) oxidation Inhibition of platelet aggregationSynthesis of proatherogenic eicosanoids Expression of procoagulant tissue factorInhibition of cell proliferationIncreased vasorelaxation and upregulation of NO synthase
(Bradamante and others 2004)
Slide9Inhibition of (LDL) oxidation
During LDL oxidation Polyunsaturated fatty acids are converted to fatty acid hydroperoxidesConjugated double bonds with a characteristic absorbance at 234 nm
(Brito and others 2002)
Slide10Inhibition of (LDL) oxidation
The increase in the absorbance intensity is significantly reduced by the pre-incubator of LDL with resveratrol (2, 4 or 6 M) in a concentration dependent manner.
pointing out that resveratrol affords an efficient protection against the ferrylmyoglobin-mediated LDL oxidation.
(Brito and others 2002)
Slide11Potential Chemoprevention
Slide12Chemoprevention
Mediate positive responses with tumor transplant models for gastric cancers (Zhou and others 2005)Hepatoma (Wu and others 2004) Neuroblastoma (Chen and others 2004)Mammary (Garvin and others 2006)Glioma (Chen and others 2006)Laryngeal (Li and others 2005) However, activity was not observed with 4T1 breast cancer (Bove and others 2002) and leukemia (Gao and others 2002)
Slide13Chemoprevention
Chemopreventative activity Inhibits the cyclooxygenase activity of COX-1Induces quinone reductase activityReduces inflammatory
(Jang and others 1997)
Slide14Inflammation
(Jang and others 1997)
Resveratrol significantly reduced pedal edema both in the acute phase (3 to 7 hours) and in the chronic phase (24 to 144 hours) in the carrageenan-induced model of inflammation in
rats.
Reveratrol (, 3mg per kilogram of body weight; , 8 mg/kg) phenylbutazone () indomethacin () control group ()
Slide15COX-1 and COX-2
COX catalyzes the conversion of arachidonic acid Pro-inflammatory substances such as prostaglandinsStimulated tumor cell growthsuppress immune surveillance Activate carcinogens to forms that damage genetic material
Slide16COX-1 and COX-2
(Jang and others 1997)
Indomethacin (
) on COX-1 activity Resveratrol on COX-1 () or COX-2 () activity
Resveratrol inhibit the cyclooxygenase activity of COX-1 and this activity correlates with antitumor promotion.Although its inhibitory activity was less than indomethacin
Slide17Skin cancer
Resveratrol also shows potentially prevention of short-term ultraviolet B radiation-mediated damages in hairless mice Reduces cutaneous edamaInhibit reactive oxygen speciesInhibit lipid peroxidation
(Afaq and others 2003)
Slide18UVB-mediated skin edema
Bi-fold skin thickness and ear punch weight were evaluated 24 h after UVB irradiation To observe the protective effect of resveratrol on UVB-mediated skin edema
(Afaq and others 2003)
Slide19UVB-mediated skin edema
The exposure of the mice to UVB (180
mJ/cm2) resulted in a significant increase in bi-fold skin thickness and ear punch weight Pretreatment of skin with resveratrol was found to result in a significant inhibition in the increases in bi-fold skin thickness and ear punch weight 24 h after UVB irradiation compared to the UVB-alone group
(Afaq and others 2003)
Slide20Human Clinical trail
Although animal studies data indicate promising activity of resveratrol human clinical trail and studies data are still limited (Walle and others 2004, Zamora-Ros and others 2006)
Slide21Plasma concentration
For oral dose, an
early peak of total radioactivity was reached at about 1 h after the dose and at 6 h after the dose, there was second peak For Intravenous, there was a rapid fall of the plasma concentrations of total radioactivity
Oral 25-mg (110 mol) () Intravenous 0.2-mg (0.8 mol) () 14C-resveratrol doses in human subjects
Slide22Recovery of total radioactivity in urine and feces
The
overall recoveries in urine and feces were 70.5 to 97.6% after the oral 53.5 to 91.2% after the intravenous dose
Slide23LC/MS of urinary excretion
Resveratrol
(RV) Metabolites (M1–M5)
M1 was a resveratrol monoglucuronideM2 was an isomeric resveratrol monoglucuronideM3 was a dihydroresveratrol monoglucuronide.M4 was a resveratrol monosulfateM5 was dihydroresveratrol sulfate
Slide24Resveratrol and metabolite in plasma
Resveratrol
(RV) Major sulfate conjugates M4/M5
10-min samples, unchanged resveratrol with an estimated concentration range of 3.7 to 16.4 ng/ml. Two subjects also demonstrated a major metabolite peak with an estimated concentration of 9 to 13.5 ng/ml30-min samples, the plasma from subjects 1 and 2 had no resveratrol, whereas in subject 3 there was a small amount of resveratrol left, but mostly the sulfate conjugate, M4/M5. samples obtained beyond 30 min, there was no unchanged resveratrol detected in any of the subjects.
Slide25Anthocyanin
Slide26Anthocyanin
Anthocyanins are a group of abundant and widely consumed flavonoid
constituentsAntioxidant activity (Castaneda-Ovando and others 2009)Disease prevention Cardiovascular illnesses Diabetes Visual dysfunction
Figure 1. General anthocyanins structure
Slide27Antioxidant activities
React with free radicalsInterrupt the propagation of new free radical speciesChelate metal ions such as Fe2+ Catalyze lipid oxidation to alter their redox potentialsSignificantly improve certain immune responses
(Hertog and others 1993)
Slide28Antioxidant activities
Figure 2. Plots showing the correlation of total anthocyanin content of samples with (a) antiradical activity, (b) reducing power and (c) with hydroxyl free radical scavenging activity
Slide29Anthocyanins and cardiovascular disease
Increased consumption of anthocyanins lowers the risk of cardiovascular disease (CVD)May regulate different signaling pathways involved in the development of CVD
(Demrow and others 1995)
Slide30Anthocyanins and cardiovascular disease
Figure 3. Representative tracing of the hemodynamic effect of intravenous grape juice
(
Demrow and others 1995)
Slide31Anthocyanins and anti-diabetic properties
Consumption of fruits and vegetables decrease the incidence of type-2 diabetesProtect pancreatic β-cells from glucose induced oxidative stress
(Al-Awwadi and others 2005)
Slide32Anthocyanins and anti-diabetic properties
Figure 4. Insulin secreted by compounds 3 and 7-9 at 4 and 10 mM glucose concentrations
(Jayaprakasam and others 2005)
Slide33Anthocyanins and anti-diabetic properties
Figure 5. Percent inhibition of COX-1 and COX-2 enzymes by Vioxx, Celebrex, aspirin, naproxen, and ibuprofen
(Zhang and others 2004)
Slide34Anthocyanins and vision improvement
British Royal Air Force aviators ate bilberry jam to improve their night visionImpaired visual function is a techno-stress syndromecaused by concentrated work on video display terminals in today’s computerised society
Slide35Anthocyanins and vision improvement
Table 1. Contrast sensitivity before and after administration in placebo and anthocyanoside group
(Lee and others 2005)
Slide36Melatonin in grapes
Structure : Precursor : tryptophan.
Slide37Sources of melatonin
Slide38Metabolic Pathyway
Four enzymes from Try to MelMelatonin regulates your sleep and wake cycles.Light also affects the amount of melatonin production in your body
Slide39Dynamic and cyclic nature of melatonin production
Human blood levels range from 20 picograms per milliliter in the morning to 55 pg/mL at night (a picogram is one-trillionth of a gram). Natural production of melatonin by the human body declines with age.Melatonin are used to treat jet lag or Insomnia(lack of sleep), (SAD).Melatonin supplement how safe are they? Overdose? Contamination? OTC or requires prescription?
Slide40Melatonin’s functions in plants
Photo-periodic reactions in higher plants. Night signalsAntioxidant activity ( protection of germen to oxidative stress).Redox cycling doesn’t occur in melatonin(suicidal antioxidant);stable end productGrowth stimulating factor
Slide41Melatonin concentration in plants??
Slide42GRAPES
Melatonin in grapes:
It is available in wide concentrations ranging from pg to
ug
/g tissue ( cultivars, ripeness, harvest time , light intensity).
Skins and seeds contain more melatonin than pulp/juice. Red grapes contain higher melatonin than white one.
In wine , fermentation also generates
melatoinin
synthesized by yeasts.
When plants defense activator,
Benzothiadiazole
(BTH) is used to treat grape vine, increase in concentration of melatonin has been observed. Melatonin is found considerably higher in some cultivars, such as
Nebbiolo
, and which can be raised further by BTH treatment.
Melatonin isomers also exists in grapes.
Slide43Melatonin concentration in the eight grape cultivars examined and in the two plasma samples used as control
SampleMelatonina (pg ml−1)Melatoninb (ng g−1)Plasma control 110.6 ± 3.2NDPlasma control 2134.7 ± 10.3NDBarbera25.5 ± 2.50.633Croatina304.6 ± 23.40.870Cabernet Sauvignon183.6 ± 18.80.422Cabernet Franc2.4 ± 0.60.005Marzemino14.9 ± 4.10.031Nebbiolo428.3 ± 32.10.965Sangiovese255.5 ± 16.30.332Merlot114.2 ± 7.20.264Merlot, BTH-treated301.5 ± 22.50.726aMelatonin concentration in plasma and grape skin extracts as determined by ELISA (means ± SE from three extraction experiments).bMelatonin content in ng, referred to 1 g of grape skin and calculated from the means in the other column of data.Iriti et al.(2006)
Slide44HEALTH SIGNIFICANCE
Is melatonin a Panacea ??
Slide45References supporting antioxidant activities of melatonin
Galano
, A., Tan, D. X., & Reiter, R. J. (2011). Melatonin as a natural ally
against oxidative stress
: a physicochemical examination.
Journal of pineal research
,
51
(1), 1-16.
Rodriguez, C., Mayo, J. C.,
Sainz
, R. M.,
Antolin
, I., Herrera, F.,
Martín
, V., & Reiter, R. J. (2004). Regulation of
antioxidant enzymes
: a significant role for melatonin.
Journal of pineal research
,
36
(1), 1-9.
Tan, D. X., Manchester, L. C.,
Terron
, M. P., Flores, L. J., & Reiter, R. J. (2007).
One molecule, many derivatives
: A never‐ending interaction of melatonin with reactive oxygen and nitrogen species?.
Journal of pineal research
,
42
(1), 28-42.
Reiter, R. J., Tan, D. X.,
Osuna
, C., &
Gitto
, E. (2000). Actions of melatonin in the
reduction of oxidative stress
.
Journal of Biomedical Science
,
7
(6), 444-458.
Slide46Antioxidant activity : mechanisms
Figure . Hypothetical pathways involved in melatonin regulation of antioxidant enzyme gene expression and activity.
Slide47Some of the proposed mechanisms by which melatonin interferes with the growth of estrogen-mediated mammary cancer cell growth.
Slide48References supporting to treat sleep disorders in Alzheimer’s disease patients.
Cardinali
, D. P.,
Brusco
, L. I.,
Liberczuk
, C., &
Furio
, A. M. (2002). The use of melatonin in Alzheimer's disease.
Neuro
endocrinology letters
,
23
, 20-23.
Slide49Sewerynek, E. (2002). Melatonin and the cardiovascular system. Neuro endocrinology letters, 23, 79.
Melatonin may reduce blood pressure via the following mechanisms:
1) by a direct effect on the hypothalamus;
2) as an antioxidant which lowers blood pressure;
3) by decreasing the level of
catecholamines
, or
4) by relaxing the smooth muscle in the aorta wall.
Slide50Melatonin and immune system
Carrillo-
Vico
, A., Guerrero, J. M.,
Lardone
, P. J., & Reiter, R. J. (2005). A review of the
multiple actions of melatonin on the immune system.
Endocrine
,
27
(2), 189-200.
Skwarlo-Sonta
, K. (2002
). Melatonin in immunity: comparative aspects.
Neuro
endocrinology letters
,
23
, 61.
Szczepanik
, M. (2007).
Melatonin and its influence on immune system
.
Journal of physiology and pharmacology
,
58
(6), 115-124.
Slide51Hypothetical scheme of melatonin regulation of cytokine production.
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