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Q: Phytonutrient research ( Answered 5 out of 5 stars,   2 Comments )
Question  
Subject: Phytonutrient research
Category: Science > Chemistry
Asked by: integro-ga
List Price: $200.00
Posted: 18 Mar 2003 05:12 PST
Expires: 17 Apr 2003 06:12 PDT
Question ID: 177695
I am interested in information on the following phytonutrients:

Ellagic Acid, indole-3-carbinol, lycopene, sulforaphane

For each one, I would like to know:
1. Which oragnic family it belongs to.
2. The molecular and structural formula.
3. The IUPAC and common name(s).
4. The physical and chemical properties.
5. Types of reactions it can undergo, along with the most common usage
of reactants to get a useful product.
6. If there are any medicinal functions (if so, elaborate).
7. A list of food or herbal sources in which it is found.

Pictures and/or diagrams are grately appreciated!

Request for Question Clarification by easterangel-ga on 19 Mar 2003 01:13 PST
I have compiled most of the data except for the IUPAC Nomenclature.
Searching on the IUPAC website does not produce any results. Would the
absence of the IUPAC Nomenclature still be accepted as a legitimate
answer.

Just let me know. :)

Clarification of Question by integro-ga on 21 Mar 2003 11:38 PST
easterangel: Your response (omitting IUPAC nomenclature) is acceptable!
Answer  
Subject: Re: Phytonutrient research
Answered By: easterangel-ga on 21 Mar 2003 18:26 PST
Rated:5 out of 5 stars
 
Hi! Thanks for the question and for accepting my proposal for an
answer.

I will try to answer your query point by point and separated it by
category. Answers would consist of one link or even a word or a
snippet from the article. Whenever possible I also included links with
pictures and diagrams.

Ellagic Acid:

1. Family and/or Group:

“Ellagic Acid is a member of the ellagitannin family of compounds.”

“Ellagic Acid”
http://www.ellagic-research.org/summary.htm 

2. The molecular, structural formula, physical and chemical
properties.
http://www.red-raspberry.org/ellagicacid.htm

Molecular Weight: 344 || Formula:C17H12O8
http://www.pl.barc.usda.gov/achem_detail.cfm?chemical_id=361 

Ellagic Acid Values
http://www.sturmsberryfarm.com/nutrition.htm#ellagic 

3. Types of reactions it can undergo, along with the most common usage
of reactants to get a useful product.

“Many plants produce ellagic acid in a complex with glucose that forms
a family of chemicals known as ellagitannins. These biochemicals are
water-soluble and easily absorbed in the diet. When recrystallized
from the melt, ellagic acid will slowly crystallize, forming beautiful
sheets of dendritic needle-like crystals.”

Ellagic Acid (Movie Included)
http://micro.magnet.fsu.edu/optics/intelplay/moviegallery/timelapse/ellagicacid.html

“Ellagic acid is a phenolic compound found in plants in the form of
hydrolyzable tannins called ellagitannins. Ellagitannins are esters of
glucose with hexahydroxydiphenic acid; when hydrolyzed, they yield
Ellagic acid, the dilactone of hexahydroxydiphenic acid. Ellagic acid
is a very stable compound and is readily absorbed through the
gastrointestinal system in mammals, including humans.”

“Ellagic acid is a phenolic compound found in plants!”
http://greenwoodhealth.net/np/ellagic.htm 


4. Medicinal Functions:

“Simply put, clinical studies are showing that Ellagic Acid may be one
of the most potent ways to prevent cancer, inhibit the growth of
cancer cells, and arrest the growth of cancer in subjects with a
genetic predisposition for the disease.”

“The ELLAGIC ACID Information Site”
http://www.ellagic-acid.org/ 

5. Food Sources

“Ellagic Acid is a naturally occurring polyphenolic constituent found
in 46 different fruits and nuts, like pomegranate, red raspberry,
strawberry, blueberry and walnuts.”

“The ELLAGIC ACID Information Site”
http://www.ellagic-acid.org/ 

“Berries are the most common food sources of Ellagic acid. The
relative amount of Ellagic acid in average number of micrograms per
gram of dry weight fruit extract is highest in red raspberries at
1500mcg, followed by strawberries at 630 mcg, walnuts at 590 mcg,
pecans at 330 mcg, and cranberries at 120 mcg. Torre, et al.,
performed a quantitative evaluation of red raspberries that was
published in the Journal of Food Sciences in 1977:”

“Ellagic acid is a phenolic compound found in plants!”
http://greenwoodhealth.net/np/ellagic.htm 


-------------
Indole-3-carbinol:

1. Family and/or Group:  

“It is a member of the class of sulfur-containing chemicals called
glucosinolates.1 It is formed from parent compounds whenever
cruciferous vegetables are crushed or cooked.2 3 Indole-3-carbinol and
other glucosinolates (e.g., other indoles and isothiocyanates such as
sulforaphane) are antioxidants…”

“Indole-3-Carbinol”
http://www.vitamins.com/HealthNotes/Supp/Indole_3_Carbinol.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

2. The molecular, structural formula, physical and chemical
properties.

Molecular Formula: C10H10N2O
Molecular Weight: 174.20
Assay: 98.0% Min

“Indole Derivatives”
http://www.accordchem.com/indole.htm 

3. Types of reactions it can undergo, along with the most common usage
of reactants to get a useful product.

“The process begins when I3C is ingested.  Stomach acid converts it
into a variety of products that ultimately induce the enzyme
cytochrome P450, which signals the body to metabolize estrogen via the
2-hydroxylation pathway.  By funneling estrogen into this "tumor
suppressor" pathway, I3C essentially "vacuums" away the estrogen.[4]

Indole-3-Carbinol stimulates the rate at which the body expels
estrogen through 2-hydroxylation.  Bradlow and a group of researchers
investigated the effects on humans of short-term oral exposure to I3C,
administering 400 mg of I3C daily to test subjects for one week. 
After I3C was consumed, the extent of 2-hydroxylation jumped from 29.3
percent to 45.6 percent.  In another study, 12 healthy volunteers
ingested 6 - 7 mg of I3C per kg of body weight, per day over one-week.
 After exposure to I3C, the rate of 2-hydroxylation in the subjects
increased by 50 percent.[5-6]”

“I3C is a powerful anti-carcinogen in and of itself, but studies have
shown that certain substances taken in conjunction with I3C boost its
effects.  Some investigators have suggested that taking ascorbic acid
(Vitamin C) along with I3C will produce ascorbigen, an even more
crucial anticarcinogen than I3C.[25]”

“Indole-3-Carbinol (I3C) -- A Powerful Anti-estrogen /
Anti-carcinogen”
http://www.dietsexercise.com/Indole-3-Carbinol-I3C-anti-estrogen-1.htm

4. Medicinal Functions:

“Feeding indole-3-carbinol or broccoli extracts rich in
indole-3-carbinol has dramatically reduced the frequency, size, and
number of tumors in laboratory rats exposed to a carcinogen. It
appears to be especially protective against breast13 14 15 16 and
cervical17 18 cancer because of a number of actions, including an
ability to increase the breakdown of estrogen. However, while most
animal studies report protective effects, a few indicate that
indole-3-carbinol may actually promote cancer formation in certain
situations, depending upon the chemical initiator of cancer, method of
exposure, and species of animal studied.19 20”

“Indole-3-Carbinol”
http://www.vitamins.com/HealthNotes/Supp/Indole_3_Carbinol.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

5. Food Sources:

“Broccoli, brussel sprouts, cabbage, cauliflower, collards, kale,
kohlrabi, mustard greens, rapeseed, rutabaga, turnip

“Indole-3-Carbinol (Indole-3-Methanol)”
http://members.xoom.virgilio.it/glioblastoma/memo_pad/memo_integrative/memo_potential_supplements/memo_brassicas/cassileth_i3c.htm

“For those who appreciate the anticarcinogenic effects of I3C, is it
enough to increase your intake of broccoli or cabbage?  According to
researchers, the answer is no.  In order to consume enough cruciferous
vegetables to have a positive effect, research suggests that a pound
or more of cabbage or cauliflower would be the required dosage, more
than most people would like to consume.  Bradlow recommends consuming
at least 300 mg of I3C daily, the minimum dose his studies have found
to be effective in human subjects.”

“Indole-3-Carbinol (I3C) -- A Powerful Anti-estrogen /
Anti-carcinogen”
http://www.dietsexercise.com/Indole-3-Carbinol-I3C-anti-estrogen-1.htm


--------------
Lycopene

1. Family and/or Group:  

“Lycopene, found primarily in tomatoes, is a member of the carotenoid
family—which includes beta-carotene and similar compounds found
naturally in food—and has potent antioxidant capabilities.”

“Lycopene”
http://www.vitamins.com/HealthNotes/Supp/Lycopene.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

2. The molecular, structural formula, physical and chemical
properties.

“Lycopene is a phytochemical, synthesized by plants and microorganisms
but not by animals. It is an acyclic isomer of beta-carotene. This
highly unsaturated hydrocarbon contains 11 conjugated and 2
unconjugated double bonds, making it longer than any other carotenoid.
As a polyene, it undergoes cis-trans isomerization induced by light,
thermal energy, and chemical reactions.”

“Biochemistry of Lycopene”
http://chemistry.about.com/library/weekly/aa050401a.htm 

Chemical Structure of Lycopene
http://chemistry.about.com/library/graphics/bllyco2.htm 

Lycopene Graphic
http://micro.magnet.fsu.edu/phytochemicals/pages/lycopene.html 

3. Types of reactions it can undergo, along with the most common usage
of reactants to get a useful product.

“Lycopene occurs in the diet predominantly in tomatoes and tomato
products, but is also found in apricots and water melons amongst other
plant foods, though in smaller amounts. Unlike other carotenoids
lycopene does not exert pro-vitamin A activity, making all of this
nutrient available for its antioxidant function in the body. Interest
in this nutrient was first raised in 1989 when it was discovered that
the singlet oxygen quenching ability of lycopene (in-vitro) is at
least twice as high as that of beta-carotene. An inverse relationship
between lycopene intake or serum values and risk has been observed in
certain types of cancers, in particular prostate, pancreas and
stomach. Depleted lycopene serum concentrations have also been found
in those suffering from certain inflammatory conditions and immune
disorders.”

Nutriscience
http://www.wassen.com/profres1/nutritional-supplements-Nutriscience.htm

4. Medicinal Functions:

Asthma, exercise-induced
Prostate cancer
Atherosclerosis (prevention only)
Cancer risk reduction
Immune function
Macular degeneration

“A study conducted by Harvard researchers examined the relationship
between carotenoids and the risk of prostate cancer.1 Of the
carotenoids studied, only lycopene was clearly linked to protection.
The men who had the greatest amounts of lycopene in their diet (6.5 mg
per day or more) showed a 21% decreased risk of prostate cancer
compared with those eating the least.”

“Lycopene”
http://www.vitamins.com/HealthNotes/Supp/Lycopene.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

5. Food Sources:

“Tomatoes and tomato-containing foods are high in lycopene. In the
Harvard study, the only tomato-based food that did not correlate with
protection was tomato juice.”

“Other foods that contain lycopene include watermelon, pink
grapefruit, and guava.”

“Lycopene”
http://www.vitamins.com/HealthNotes/Supp/Lycopene.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

“Lycopene (see chemical structure), a carotenoid in the same family as
beta-carotene, is what gives tomatoes, pink grapefruit, apricots, red
oranges, watermelon, rosehips, and guava their red color.”

“Biochemistry of Lycopene”
http://chemistry.about.com/library/weekly/aa050401a.htm 


----------------
Sulforaphane

1. Family and/or Group: 

“Sulforaphane is one of a class of chemicals called isothiocyanates.
Sulforaphane and other isothiocyanates are antioxidants and potent
stimulators of natural detoxifying enzymes in the body.”

“Sulforaphane”
http://www.vitamins.com/HealthNotes/Supp/Sulforaphane.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

2. The molecular, structural formula, physical and chemical
properties.

Graphic
http://micro.magnet.fsu.edu/micro/gallery/phytochemicals/phytochemical.html

Sulfur Chemistry including Sulforaphane Reaction
http://www-anorganik.chemie.uni-wuerzburg.de/schenk/sulfur.html 

3. Types of reactions it can undergo, along with the most common usage
of reactants to get a useful product.

“Sulforaphane has been isolated as a potent isothiocyanate inducer.
Research indicates that isothiocyanates have a double effect in
helping detoxify harmful substances from the body by firstly down-
regulating Phase I Enzymes and inducing Phase II Enzymes that help
with the detoxification of unwanted metabolites in the body.”

“The Phase I Enzymes (cytochrome P-450 enzyme system) turn unwanted
substances into a form that is easier to dispose from the body.
However, this process can in certain instances increase toxicity of
the intermediary metabolites formed, before they are worked on by
Phase II Enzymes, which are involved with the final step of their
removal.”

“Nutriscience”
http://www.wassen.com/profres1/nutritional-supplements-Nutriscience.htm

4. Medicinal Functions:

“Human studies with sulforaphane and other cruciferous-vegetable
components have shown that these compounds stimulate the body’s
production of detoxification enzymes and exert antioxidant effects.”

“Preliminary studies suggest that in order to cut the risk of cancer
in half, the average person would need to eat about two pounds of
broccoli or similar vegetables per week. Since the concentration of
sulforaphane is much higher in broccoli sprouts than in mature
broccoli, the same reduction in risk theoretically might be had with a
weekly intake of just over an ounce of sprouts.”

“Sulforaphane”
http://www.vitamins.com/HealthNotes/Supp/Sulforaphane.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

5. Food Sources:

“Sulforaphane is found in highest concentrations in broccoli sprouts,
but it is also found in mature broccoli and other cruciferous
vegetables, such as cauliflower, cabbage, and kale.”

“Sulforaphane”
http://www.vitamins.com/HealthNotes/Supp/Sulforaphane.htm?xs=C180ABC4A7E143E6BAA887562B0ED898

Search terms used:         
“Ellagic acid”, “indole-3-carbinol”, lycopene, sulforaphane
chemistry chemical structure reactions foods 
        
I hope these links would help you in your research. Before rating this
answer, please ask for a clarification if you have a question or if
you would need further information.
        
Thanks for visiting us.         
        
Regards,         
Easterangel-ga         
Google Answers Researcher
integro-ga rated this answer:5 out of 5 stars

Comments  
Subject: Re: Phytonutrient research
From: carpediem-ga on 18 Mar 2003 08:14 PST
 
Hello integro

I am currently doing research on indole-3-carbinol. The following pdf
file contains 25 pages of information including diagrams.

http://ntp-server.niehs.nih.gov/htdocs/Chem_Background/ExSumPdf/Indolecarbinol.pdf

carpediem
Subject: Re: Phytonutrient research
From: trinity_ah-ga on 18 Mar 2003 20:31 PST
 
It's my first time on the site, but if I understand correctly, only
researchers can answer questions and be compensated.  I don't want to
mess anything up here, but I already have some of the information you
are looking for... minus the stuff on indole-3-carbinol, which
carpediem has already provided.  Let me know if you want what I've
got.

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