FOOD BIOCHEMISTRY
LESSON 4:
NEUTRACEUTICALS
In this lesson we will deal with what neutricueticals are and how
the play a role in our lives.
Neutricueticals
A neutraceutical can be defined as “a diet supplement that
delivers a concentrated form of a biologically active component
of food in a non-food matrix to enhance health.”
Biologically Active Components
Phytonutrients: Potentially Protective Compounds in
Plant Foods
There is overwhelming epidemiological evidence that diets rich
in fruit and vegetables are associated with a lower incidence of
cancer, cardiovascular, and other degenerative diseases. To some
extent, this may be because such diets provide less fat, and
especially saturated fat, than diets that are richer in meat. The
relatively high content of vitamins C and E and carotenoids in
plant foods may also be important. In addition, fruits and
vegetables contain a wide variety of compounds that have
(potential) protective actions. These compounds are not strictly
nutrients, in that they are not dietary essentials and have no
physiological function.
Many fruits contain salicylates, which inhibit the synthesis of
thromboxane Az, and have an anticoagulant action, in amounts
that provide the same intake as the low dose of aspirin used as
prophylaxis against thrombosis.
Plant sterols inhibit the intestinal absorption of cholesterol and
so have a useful hypocholesterolemic action. They also inhibit
endogenous synthesis of cholesterol, by inhibiting and
repressing the regulatory enzyme of cholesterol synthesis,
hydroxymethylglutaryl (HMG)-CoA reductase. Other com-
pounds synthesized from mevalonate also inhibit and repress
HMG-CoA reductase and have a hypocholesterolemic action,
including squalene (found in relatively large amounts in olive
oil), ubiquinone, and the tocotrienols.
A number of the terpenes in aromatic oils of citrus peel, herbs,
and spices inhibit the isoprenylation of the P21-ras oncogene
product. Isoprenylation is essential for the biological action of
the ras protein, which is associated with pancreatic cancer.
The Phytochemical Evolution
Phytochemicals, by the strictest definition, are chemicals that are
produced by plants. Currently, the term is being used only for
those plant chemicals that may have health-related effects but are
not considered essential nutrients (proteins, carbohydrates, fats,
minerals, and vitamins
When plants first evolved, there was little free oxygen in the
atmosphere. As oxygen levels increased, a direct result of plant
metabolism (plants take in carbon dioxide and give off
oxygen), their environment became polluted. Over time, plants
acquired new antioxidant compounds, which afforded them
protection from molecules of highly reactive oxygen. These
© Copy Right: Rai University
24
plants survived the oxygen pollution and slowly evolved into
today’s oxygen tolerant plants. Biochemical defenses against
bacteria, fungi, viruses, and damage to cell structures, especially
DNA, also became part of the plant world’s arsenal
As animal species evolved, many were able to “borrow” some
of the protective phytochemicals from the plants composing
their diets, saving these species the trouble of having to
manufacture all their own chemical defence mechanisms. This,
of course, happened to the human animal as well
The Phytochemical Revolution
Since the 1970s, increasing numbers of studies are finding
associations between the food people eat, their health, and their
life expectancy. In the ’70s, concerns focused on the role of
dietary cholesterol in causing heart disease and cancer. Although
the importance of cholesterol in the human diet turned out to
be relatively unimportant (high blood levels of cholesterol can
be dangerous, but they are not caused by eating cholesterol) it
did help to shift the focus on health from treatment to
prevention
Another discovery has focused attention on the importance of
phytochemicals. Pregnant women with diets deficient in folic
acid have a higher incidence of babies with spina bifida and
other neural tube defects. These devastating birth defects result
from incomplete development of the fetal brain, spinal cord,
skull, or spinal column, yet the majority of cases are completely
preventable with a healthy diet
During the 1980s and 1990s, numerous laboratories began
studying phytochemicals to “mine” plants for bioactive
substances that might be used as “medicines” (nutriceuticals) or
for other chemical applications. Many compounds are showing
great promise as disease fighters in the body, boosting produc-
tion or activities of enzymes, which then act by blocking
carcinogens, suppressing malignant cells, or interfering with the
processes that can cause heart disease and stroke
As an example, homocysteine is an amino acid produced by the
body, usually after eating meat, which has been established to
cause atherosclerosis, a build-up of fat and other materials on
the inside of arteries. Research has proven that diets deficient in
folic acid, and vitamins B-6 and B-12, are associated with higher
blood levels of homocysteine and a higher incidence of heart
disease and stroke. Adding nutritional supplements or foods
(such as beans, potatoes, bananas, and broccoli) can reduce
elevated homocysteine levels, lowering the risk of heart attack
and stroke
While many laboratories have been searching for and studying
individual phytochemicals, other scientists have been conduct-
ing epidemiological studies (studies of diseases in populations)
to see what effect different diets have on people. Significantly,
they’ve been able to contrast and compare genetically similar
people in different dietary environments; e.g. comparing the
2D.501
health of Japanese eating a traditional diet in Japan versus
Japanese-Americans eating a conventional American diet.
Hundreds of studies from around the world have established
that diets high in plant-based foods are associated with lower
rates of cancer and heart disease, sometimes astonishingly so.
One analysis of data from 23 epidemiological studies showed
that a diet rich in whole grains and vegetables reduced the risk
of colon cancer by 40 percent. Another study demonstrated that
women who don’t eat many fruits and vegetables have a 25
percent higher risk of developing breast cancer.
Phytochemical use comes with a caution sign, however. These
compounds aren’t always beneficial under all circumstances or in
high doses. Certain biochemicals and vitamins, at least as
provided in supplements, have been found to encourage the
growth of cancer cells and their use is being discouraged in
patients undergoing cancer treatments. And, although it has
many benefits in other circumstances, high doses of beta-
carotene supplements are associated with an increased risk of
lung cancer in male smokers.
As they occur naturally in plant foods, phytochemicals promise
to create an entirely new philosophy of “functional foods,”
eating not just to sustain minimal basic health but also eating
to prevent disease. In the future, we may tailor our diets to
include the foods that will best address our personal health
problems and risks as well as maintain optimal health.
Allyl Sulfur Compounds
Members of the allium family (onions, garlic, and leeks) contain
cysteine sulfoxide derivatives (allyl sulfur compounds), such as
allicin and alliin. When the plant cells are damaged, the enzyme
alliinase is re-leased from vacuoles and catalyzes the formation
of thiosulfinates and thiols, including the lachrymator
thiopropanal S-oxide. Their function in the plant is presumably
to provide protection against attack by pests.
The allyl sulfur compounds have two actions that may protect
against the development of cancer:
1. They reduce the activation of many pro-carcinogens to the
active carcinogen by lowering the activity of microsomal
cytochrome P 450 enzymes. They achieve this by acting as
partial substrates of the enzyme, leading to mechanism-
dependent inhibition; antagonizing the induction of
cytochrome P 450 by ethanol and various other
compounds; and by decreasing the translation of mRNA,
with no effect on transcription.
2. They increase the metabolic clearance of potential
carcinogens and their metabolites, by induction of
glutathione S-transferases.
The allyl sulfur compounds of garlic also have an anticoagulant
action (by inhibiting platelet coagulability) and inhibit choles-
terol synthesis by inactivating HMG-CoA reductase.
Ajoene - Garlic, Allium sativum, is a member of the lily family
that has been cultivated by humans as a food plant for over
10,000 years. It has been the bane of fictional vampires for
hundreds of years and a folk remedy for thousands of years.
Since the 1980s, science has been discovering that garlic does, in
fact, have numerous medicinal properties. Ironically, one of
those properties is that it acts as a blood thinner. Ajoene is a
© Copy Right: Rai University
2D.501
naturally occurring “nutriceutical” that might reduce the risk of
FOOD BIOCHEMISTRY
stroke and heart disease. Ajoene, an unsaturated sulfoxide
disulfide, is the principal chemical responsible for garlic’s
anticoagulant properties. It is a component of allicin, a sulfinyl
compound that gives garlic its strong odor and flavor. Ajoene is
currently being developed as a pharmaceutical for the treatment
of blood clotting disorders. As a naturally occurring
“nutriceutical”, this potent phytochemical might reduce the risk
of stroke and heart disease. In addition, ajoene also has been
found to have effective antimicrobial properties, inhibiting the
growth of both bacteria and fungi.
Polyphenols and flavonoids
Polyphenols are a large and diverse class of compounds, many
of which occur naturally in a range of food plants; fruits,
vegetables, and nuts and their products. The flavonoids are the
largest and best-studied group of these. They occur in plants as
glycosides and possess important antioxidant properties some
also function to defend the plants against attack, others are
pigments in flowers and fruits. A range of plant polyphenols
are either being actively developed or currently sold as dietary
supplements and/or herbal remedies. Although, these
compounds play no known role in nutrition (non-nutrients),
many of them have properties including antioxidant, anti-
mutagenic, anti-oestrogenic, anti-carcinogenic and
anti-inflammatory effects that might potentially be beneficial in
preventing disease and protecting the stability of the genome.
However not all polyphenols and not all actions of individual
polyphenols are necessarily beneficial. Some have mutagenic
and/or pro-oxidant effects, as well as interfering with essential
biochemical pathways including topoisomerase enzyme
activities, prostanoid biosynthesis and signal transduction.
There is a very large amount of in vitro data available, but far
fewer animal studies, and these are not necessarily predictive of
human effects because of differences in bacterial and hepatic
metabolism of polyphenols between species. Epidemiological
studies suggest that high green tea consumption in the
Japanese population and moderate red wine consumption in
the French population may be beneficial for heart disease and
cancer, and these effects may relate to specific polyphenols. A
small number of adequately controlled human intervention
studies suggest that some, but not all polyphenol extracts or
high polyphenol diets may lead to transitory changes in the
antioxidative capacity of plasma in humans. However, none of
these studies have adequately considered long-term effects on
DNA or the chromosome and unequivocally associated these
with polyphenol uptake. Furthermore, clinical trials have
required intravenously administered polyphenols at concentra-
tions around 1400mg/m(2) before effects are seen. These
plasma concentrations are unlikely to be achieved using the
dietary supplements currently available. More focused human
studies are necessary before recommending specific polyphenolic
supplements at specific doses in the human population.
In the 1940s, the flavonoids were known as vitamin P (for
permeability), because they were shown to have effects on the
permeability of blood capillaries. They were not shown to be
dietary essentials. By the 1970s, they were regarded as hazardous
mutagens and potential carcinogens, because they can undergo
25
 redox cycling reactions and generate oxygen radicals. By the
FOOD BIOCHEMISTRY
1990s, they were regarded as potentially protective compounds
with three types of action.
1. Although they can undergo redox cycling, they can also act
as radical trapping antioxidants.
2. They reduce the activation of many pro-carcinogens to the
active proximate carcinogen by lowering the activity of
microsomal cytochrome P 450 enzymes.
3. They increase the metabolic clearance of potential
carcinogens and their metabolites by inducing the enzymes
involved in conjugation for excretion.
Many of the glycosides are hydrolyzed by intestinal bacterial
glycosidases, and the aglycones are absorbed. Flavonoids include
proanthocyanidins, quercetin, and epicatechin, found mainly in
chocolate, tea, and wine. Red wine also contains resveratrol, a
nonpolyphenol antioxidant product of grape skins. The
“French paradox” refers to the epidemiologic finding that the
incidence of coronary heart disease was significantly lower in
wine-drinking regions of France than in areas where wine was
not the main alcoholic beverage. Subsequently, it was shown
that wine phenols inhibited the oxidation of low-density
lipoprotein (LDL), an accepted reason for the preventive effect
of polyphenols on the development of atherosclerosis. More
recent studies demonstrate that the attenuation of coronary
heart disease risk in wine drinkers is probably due as much to
their lifestyle consumption of high amounts of polyphenol-
containing fruits and vegetables as to wine. A 5-y prospective
Dutch study of 800 elderly men found that the ingestion of
flavonoids, mainly in tea, onions, and apples, was associated
with significant reduction in mortality from coronary heart
disease. In addition to antioxidant effects on LDL, other
potentially cardioprotective effects of polyphenols include
inhibition of platelet aggregation and vascular relaxation
through the production of nitric oxide. Although polyphenols
have the capacity to decrease LDL oxidation, inhibit platelet
aggregation, and induce vascular relaxation, their clinical efficacy
is modulated by many factors that include differences in wine
and tea preparation, volatility, and absorbability. For example,
green tea has a higher concentration of polphenols than black
tea, which may be affected by the method of brewing. Wine
should be consumed in moderation only, to avoid the chronic
effects of alcohol.
Glucosinolates
Glucosinolates are glucosides of sulfur-containing amino acid
derivatives found mainly in brassicas; the enzyme myrosinase in
the plant and similar intestinal bacterial enzymes catalyze
cleavage of the glycoside to form a variety of isothiocyanates,
thiocyanates, and the aglycone. The glucosinolates have two
actions that may protect against the development of cancer:
1. They reduce the activation of many pro-carcinogens to the
active proximate carcinogen by both inhibiting and.
reducing the synthesis of microsomal cytochrome P 450
enzymes.
2. They increase the metabolic clearance of potential
carcinogens and their metabolites, by the induction of
glutathione S- transferases and quinone reductases.
© Copy Right: Rai University
26
Myrosinase action on the glucosinolate progoitrin yields goitrin,
which inhibits the synthesis of thyroid hormones by inhibition
of the iodination of monoiodotyrosine to diiodotyrosine and
thus has a goitrogenic action. In addition, the thiocyanate
released by myrosinase competes with iodide for uptake into
the thyroid and may be goitrogenic when iodine status is
marginal. There is no evidence that normal consumption of
vegetables has any effect on thyroid hormone status, although
goiter is a problem when cattle are fed on large amounts of
brassicas.
Phytoestrogens
A number of compounds that occur in plant foods as glyco-
sides and other conjugates have weak estrogenic/ antiestrogenic
actions, and are collectively known as phytoestrogens. They all
have two hydroxyl groups that are the same distance apart as the
hydroxyl groups of estradiol and can bind to estrogen recep-
tors. The amounts of phytoestrogens produced increase in
response to microbial and insect attack, suggesting that they
have antibacterial or antifungal actions in the plant. They
produce typical estrogen responses in animals, with a biological
activity 1/500 to 1/1,000 of that of estradiol.
High consumption of legumes, especially soya beans, which are
rich sources of phytoestrogens, is associated with lower
incidence of breast and uterine cancer, as well as a lower
incidence of osteoporosis. The estrogenic action is probably
responsible for the effects on the development of osteoporosis,
whereas three factors may be involved in the effect on hormone-
dependent cancer:
In Asia, soybeans (Glycine max) have been cultivated as a food
crop for over five thousand years. Although the origins of the
plant are obscure, many botanists believe it to have derived
from Glycine ussuriensis, a legume family member native to
central China. Today, soy plants are cultivated around the world
with the United States being one of the leading producers.
While soy still serves as a valuable source of protein for
millions of people in Asia, over 90 percent of the soy crop
grown in the United States is used to feed livestock.
Isoflavones are multipurpose biochemicals that have several
functions in the soy plant: they contribute colour to the
soybean, protect the plant against bacterial and fungal infections,
and serve a hormone-like role (as a phytoestrogen) in plant cell
regulation.
Scientists are discovering that when people eat soy products,
such as tofu and soymilk, isoflavones and their derivatives
produce health benefits in addition to nutritional values.
Research suggests that soy isoflavones benefit humans in four
ways: as estrogens and antiestrogens, as cancer-enzyme inhibi-
tors, as antioxidants, and as immune system enhancers or
stimulants.
Soy isoflavones are phytoestrogens that are derived from the
protein fraction of the soybean and its food products (eg, soy
milk, soy flour, tofu, miso), include genistein and daidzein, and
possess estrogenic properties because of the similarities of their
chemical structures to estrogenic compounds. Clinical trials
identified the potential efficacy of soy isoflavones in the
prevention of coronary heart disease, osteoporosis, and breast
2D.501
and prostate cancer. A meta-analysis of 37 clinical studies
suggested that soy protein upto 45 g per day can lower serum
cholesterol levels by 10%, but the long-term effects of soy on
cardiac risk are unknown.
Because phytoestrogens compete with estrogen for binding to
estrogen receptors, their use could have beneficial effects in
preventing osteoporosis and sex hormone–mediated malig-
nancy, such as breast and prostate cancer. The clinical data are
mixed and inconclusive on the effect of soy isoflavones on
bone turnover and bone density. Data are mixed on whether
soy isoflavones promote or protect against breast cancer, and
one retrospective study of 1300 non-Asian women with breast
cancer history found no association of phytoestrogen use and
breast cancer risk. Although prostate cancer rates are lower in
Eastern cultures where soy products play a major role in the
diet, and although genistein inhibits the growth of prostate
cancer cells, clinical studies to date have failed to demonstrate
positive effects of dietary soy products on reducing the risk of
prostate cancer.
1. The isoflavones are mainly anti-estrogenic, because they
compete with estradiol for receptor binding, but the
phytoestrogen-receptor complex does not undergo normal
activation, thus it has only a weak effect on hormone
response elements on DNA. Even those phytoestrogens
that have a mainly estrogenic action will reduce
responsiveness to estradiol because they compete for
receptor binding but have lower biological activity.
2. The phytoestrogens increase the synthesis of sex hormone
binding globulin in the liver by stabilizing mRNA, leading
to a lower circulating concentration of free estradiol.
3. Some of the phytoestrogens inhibit aromatase and
therefore reduce the endogenous synthesis of estradiol,
especially the unregulated synthesis that occurs in adipose
tissue.
Genistein - Found in soy products, genistein is an isoflavone
derivative that is proving to be a strong inhibitor of cancer and
may be useful in the creation of new anti-cancer drugs.
Genistein, an isoflavone derivative related to coumarin, is found
in soy products and holds great promise as a natural cancer
preventative. There are a number of isoflavones in soy prod-
ucts, but research has shown that genistein is the most potent
inhibitor of the growth and spread of cancerous cells. Coupled
with epidemiological studies, which suggest a strong cancer
preventative effect of high soy diets, genistein is being scruti-
nized as a potential anti-cancer drug.
Some Active Compounds
Butyl phthalide It’s the distinctive taste and smell of celery, but
also offers protection against cancer, high blood pressure and
high cholesterol levels. No wonder the ancient Greeks gave
stalks of celery as trophies for their athletes
The distinctive smell and taste of celery and celery seed does
more than enhance our experience of soups and salads.
Scientists have discovered a natural ingredient that may also
protect us against cancer, high blood pressure and high
cholesterol.
© Copy Right: Rai University
2D.501
Native to Mediterranean areas and the Middle East, celery
FOOD BIOCHEMISTRY
(Apium graveolens) is a member of the carrot family and has
been cultivated for thousands of years. Historically, celery has
been used as a flavoring agent and for medicinal purposes. It
wasn’t until the 1600s that celery was actually used alone for
food.
Research is showing that the early use of celery as a medicine
was not unfounded. 3-n-butyl phthalide, one of the compo-
nents that gives celery its characteristic smell and taste, is
especially potent as an anti-tumor agent. Along with the
compound sedanolide, an aromatic ingredient also found in
celery, 3-n-butyl phthalide significantly reduces the incidence of
tumors in laboratory animals. Other studies suggest that this
and other phthalides may also help reduce high cholesterol.
Even though it’s high in sodium (as vegetables go), celery is
also proving to be effective at lowering blood pressure because
3-n-butyl phthalide has been demonstrated to relax the smooth
muscles that line blood vessels.
Calcium pectate - Research by the USDA has shown that
calcium pectate, a pectin fiber that adds crispness to fruits and
vegetables, has potent cholesterol-lowering properties. During
digestion, calcium pectate binds to bile acids. This interaction
induces the loss of small amounts of the acids, which are made
from cholesterol. The body then removes cholesterol from the
blood to make more bile for digestion. Calcium is an essential
mineral nutrient for all living organisms including bacteria,
animals, and plants. Combined with pectin, the “glue” that
holds plant cells together, calcium forms a pectate salt that helps
keep the cell walls sturdy and rigid. Calcium pectate is found in
all of the fruits and vegetables we eat. From apples and carrots
to cabbages and onions, this essential phytochemical is respon-
sible for the characteristic crunch that helps make vegetables so
delicious.
Capsaicin - This chilli pepper-derived spice packs the wallop in
your veg-kolhapuri, it is also a digestive aid, a topical painkiller,
and a potential cancer-fighting compound.
If you like it hot, capsaicin is your ticket to a mouth-blasting,
sweat-breaking spicy cuisine. Of the six capsaicinoid com-
pounds produced by chili peppers, all of which contribute to
the spiciness of the pepper, capsaicin adds the most wallop.
And while capsaicin is popular for its mouth burning, eye
watering, and breath-taking effects, scientists are learning that
this phytochemical offers more than just culinary delights. It’s
actually good for you.
Chillies (genus Capsicum), the only plants that contain capsai-
cin, are natives of South America, but have achieved worldwide
distribution and popularity since the Spanish introduced them
to Europe over 500 years ago.
Capsaicin has been found to possess several beneficial health
qualities. It has antibacterial properties, which may help people
with conditions such as stomach ulcers, rather than injuring
them further as doctors have traditionally thought. It acts as a
general digestive aid, increasing secretions of saliva and gastric
juices, and promoting intestinal activity. In studies with
animals, cancer researchers have found that capsaicin keeps
27
 certain carcinogens from binding to DNA, giving it merit as a
FOOD BIOCHEMISTRY
potential anti-cancer drug.
Currently, the best-known medical use for capsaicin is as a
topical painkiller, fighting fire with fire as it were. The very
quality that causes the burning sensation also causes nerve
endings to release mediators, chemical substances that inform
the brain about pain or inflammation. When applied directly to
an area that is causing pain, capsaicin empties the stores of
inflammatory mediators from the nerve endings, so they can no
longer transmit pain signals to the brain. Pepper creams with
capsaicin have been developed and are being used as painkillers
for conditions such as herpes (shingles), arthritis, and neuralgia.
Capsaicin is also used for defence in pepper sprays, such as
Mace, but there are questions about its safety in that application.
There have been reported cases of victims developing respira-
tory problems after being sprayed. In some instances, deaths
have even occurred from respiratory arrest.
Cathecin Hydrate - Cancer-fighting properties have been
attributed to tea. For 3,000 years, before it became a social and
recreational beverage, tea was used as a medicine and wisely so it
would seem. The tea plant, Camellia sinensis, is proving to be a
powerhouse with an array of cancer-fighting phytochemicals
(non-nutrient plant chemicals). The most promising of these is
catechin, a tannin derivative that gives tea its astringency and is
common to many plants such as grapes, berries, and ferns.
Catechin compounds are found in the leaves of both green and
black teas, but green teas have much higher levels of catechin
than do black teas. Black and green teas differ only in how they
are processed. Black tea leaves go through a fermentation
process that gives the tea its characteristic dark colour and tart
flavour.
Catechins defeat cancer in at least one of three ways. First, they
can prevent the formation of carcinogens, second, they turn up
the body’s natural detoxification defenses, and finally, they
suppress cancer promotion.
In the laboratory, animal studies have shown that catechins have
other promising qualities: acting as an antibacterial and antiviral
agent, regulating cholesterol and blood pressure, and reducing
blood clotting tendencies that may cause heart attacks or strokes.
Epidemiological studies (how diseases are distributed in
populations) aren’t yet conclusive, but suggest that those
populations that drink more green tea live longer than those
that don’t.
Coumarin – It is a blood thinning agent that acts as a rat
poison, but warfarin (a coumarin derivative) is the most
commonly used oral anticoagulant medication. Coumarin is the
parent organic compound of a class of naturally occurring
phytochemicals found in many plant species. It is best known
for its fragrance, described as a vanilla-like odour or the aroma
of freshly mowed hay. Identified in the 1820s, coumarin has
been synthesized in the laboratory since 1868 and used to make
perfumes and flavourings. It is also used to prepare anticoagu-
lants and rodent poison.
Coumarin is found in a variety of plants such as Tonka bean,
lavender, sweet clover grass, and licorice, but also occurs in food
plants such as strawberries, apricots, cherries, and cinnamon. It
© Copy Right: Rai University
28
is thought to work by serving as a pesticide for the plants that
produce it.
Chemically, coumarin can occur either free or combined with the
sugar glucose to produce a coumarin glycoside. Medically,
coumarin glycosides have been shown to have blood-thinning,
anti-fungicidal, and anti-tumor activities. Dicumarol, a coumarin
glycoside better known as warfarin, is the most commonly used
oral anticoagulant medication.
Ellagic acid - A natural pesticide in many fruit plants, such as
strawberries and raspberries, this phytochemical fights cancer in
humans. Ellagic acid is a naturally-occurring phytochemical
pesticide found in a variety plant species. This biochemical
serves a number of possible functions in these plants, regulat-
ing plant growth and seed germination, and protecting them
from microbial infections. Ellagic acid may also protect plants
from cancer-inducing chemicals, heavy metal poisoning, and
predation by insects and insect larvae. Since the early 1990s,
researchers have been discovering that ellagic acid offers health
benefits to humans as well.
Early evidence shows that ellagic acid acts as a scavenger to
“bind” or chemically engage cancer-causing chemicals, making
them inactive. In addition, this fused bi-nuclear coumarin
derivative prevents the binding of carcinogens to DNA and
reduces the incidence of cancer in cultured human cells exposed
to carcinogens.
Ellagic acid is widely found in plants such as raspberries,
strawberries, blackberries, cranberries, walnuts, and pecans, but
the greatest amounts have been observed in raspberries. While
the leaves of these plants contain the highest concentrations of
ellagic acid, the compound is also found in their fruits and nuts.
Although ellagic acid is the bioactive agent that offers protec-
tion, the phytochemical is generally ingested in the form of
another biochemical called ellagitannin. Plants produce ellagic
acid and glucose that combine to form ellagitannins, which are
water-soluble compounds that are easier for animals to absorb
in their diets. Consequently, small amounts of ellagitannins
derived from natural sources may be more effective in the
human diet than large doses of purified ellagic acid.
Heliotropin - This vanilla-like safrole derivative is not a
nutritional phytochemical, but is being studied for its relaxing
properties in aromatherapy.
Also known as piperonal or the oil of sassafras, heliotropin is
an extract of sassafras that has been used for decades in the
manufacture of perfumes and soaps. Heliotropin is a derivative
of safrole, a naturally-occurring aromatic biochemical obtained
from botanical sources such as Cinamomum petrophilum and
Sassafras albidum.
Although safroles are known to display antibacterial and
antiviral activity, their use in foods has been banned because
they are carcinogenic and hepatoxic (toxic to the liver). As such,
safrole derivatives are not considered nutritional
phytochemicals, but some of them are being exalted for their
aromatherapeutic properties.
Research at Memorial Sloan-Kettering Cancer Center found a 63
percent decrease in patient anxiety during magnetic resonance
imaging scans when the air was scented with the vanilla-like
2D.501
aroma of heliotropin. Purified heliotropin crystals have been
sold in stores alongside aromatic oils, but the distribution of
this compound is becoming increasingly controlled because it is
frequently being used to manufacture designer drugs, such as
Ecstasy and methylenedioxyamphetamine (MDA).
Indole - Found throughout nature, this aromatic nitrogen
heterocycle assumes the form of a potent cancer fighter in the
vegetables everybody loves to hate: broccoli, brussel sprouts,
cabbage.
The indole nucleus, known to chemists as benzopyrrole, is the
parent member of a broad spectrum of nitrogen heterocyclic
biochemicals commonly found in nature. Indole derivatives
occur in flower oils such as jasmine and orange blossom, and in
less pleasant substances such as coal tar and faecal matter.
Indoles also exist as melanin-related organics and indigoid
pigments.
One prominent indole configuration, indole-3-carbinol, has
achieved notoriety as a therapeutic phytochemical. This recogni-
tion is not only because of the anticancer activity of
indole-3-carbinol, but because the vegetables in which it occurs
belong to the much maligned Brassica genus of cruciferous
vegetables; the ever unpopular broccoli, brussel sprouts,
cabbage, cauliflower, and kale. It would seem that indole-3-
carbinol is partially responsible for the strong flavour that
makes these vegetables so unpopular . . . and so healthy.
Indole-3-carbinol is a highly effective anticancer agent, blocking
carcinogenic substances before they reach their cellular targets
and eliminating DNA damage in cell nuclei. It may also turn
out to be an important chemical tool in fighting breast cancer
because it inhibits estrogen-induced growth of cancer cells and
converts the more dangerous forms of estrogen to safer forms.
Lutein is one of 600 naturally occurring fat-soluble antioxidant
carotenoid biochemicals that are found in green leafy vegetables
such as spinach, kale, collared greens, romaine lettuce, leeks and
peas. Lutein acts to filter and shield harmful blue light from the
eye and protect against age-related macular degeneration, the
leading cause of blindness in people over 65.
Lutein is one of 600 naturally occurring fat-soluble antioxidant
carotenoid biochemicals that are found in green leafy vegetables
such as spinach, kale, collard greens, romaine lettuce, leeks and
peas. The central area of the retina in humans and primates is
called the macula and contains lutein as the primary carotenoid.
Lutein acts to filter and shield harmful blue light from the eye
and protect against age-related macular degeneration, the leading
cause of blindness in people over 65. One study indicated that
adults with the highest dietary intake of lutein had a 57 percent
decreased risk of macular degeneration compared to those with
the lowest intake.
Ounce for ounce, spinach contains more than 60 times as much
lutein as yellow corn.
Lutein and related carotenoids are now believed to protect
against development of cataracts, and may have other health
benefits as well.
Lycopene - Animals are completely dependent upon plants for
this reddish phytochemical natural pigment. Deposited in a
© Copy Right: Rai University
2D.501
number of body tissues, lycopene protects against heart disease,
FOOD BIOCHEMISTRY
certain cancers, and a multitude of other disorders.
It’s the red in your tomato and the pink in your grapefruit, but
in your body, it’s a proven anti-oxidant that may lower the risk
of certain diseases including cancer and heart disease.
Lycopene is one of approximately 600 known carotenoids;
chemicals that are responsible for the red, orange, and yellow
colour in fruits and vegetables. It is found in foods like
tomatoes, watermelon, grapefruit, guava, rosehip, and red
chilies.
Carotenoids also play a major role in the biological colouration
of animals. They are known to be essential for plant growth
and photosynthesis, and are vital, researchers are discovering, for
good health in animals.
Only green plants and some microorganisms (bacteria, fungi,
and lower algae) can manufacture carotenoids. Animals,
including people, store these vital chemicals in their bodies, but
are dependent on plants as a source.
In the body, lycopene is deposited in the liver, lungs, prostate
gland, colon and skin. Its concentration in body tissues tends to
be higher than all other carotenoids. Some organs, such as the
testes and adrenal glands, store higher levels of lycopene than
do other organs or tissues.
Dietary consumption of lycopene (mostly from tomato
products) has been associated with a lowered risk of prostate
cancer. Men with higher levels of lycopene in their blood had
statistically significant lower rates of cancer than did men with
lower blood levels of lycopene. Studies have also shown that
men who eat more lycopene-rich foods have less heart disease.
Ongoing research suggests that lycopene can reduce the risk of
macular degenerative disease, serum lipid oxidation and cancers
of the lung, bladder, cervix and skin.
In the future, plants may not be the only source of carotenoids
such as lycopene. The commercial production of natural
carotenoids through microbial biotechnology is already
established and expanding, mainly through the exploitation of
microalgae that can synthesize large amounts of carotenoids.
Paracoumaric acid - A phenolic compound based on the
coumarin heterocyclic nucleus, para-coumaric acid inhibits the
development of stomach cancer by stopping the formation of
nasty nitrosamines.
Para-coumaric acid is a phenolic coumarin derivative that
inhibits the development of stomach cancer and is found in
various plants such as tomatoes, green peppers, carrots,
strawberries, and pineapples, as well as herbal plants like basil,
and turmeric. Activated during digestion, para-coumaric acid
interferes with the development of cancer-causing nitrosamines
in the stomach.
Nitrosamines, a group of organic compounds containing the
reactive nitro (N=O) moiety, were discovered more than 100
years ago, but it wasn’t until the 1950s that they were found to
be highly carcinogenic in laboratory animals. Food products,
such as cured meats, pickled foods, and dried salted fish, are
associated with the development of nitrosamines. It is believed
that the process starts in the stomach when nitrate salts are
29
 reduced to form nitrites. The resulting nitrites combine with
FOOD BIOCHEMISTRY
secondary amines, derived from bacterial action on meat
proteins, to produce small amounts of carcinogenic nitro-
samines.
Para-coumaric acid inhibits this process by binding to nitric acid
derivatives, preventing them from combining with biochemical
amines to form dangerous nitrosamines. Researchers have
determined that 90 percent of all nitrosamine compounds
tested in experimental animals have been shown to cause cancer.
To date it has not been established which nitrosamine deriva-
tives or what doses, if any, are safe for human consumption.
Saponin - The plant biochemicals that produce suds in root
beer are also effective antimicrobial, cholesterol-lowering, and
anticancer phytochemicals. Some saponins, such as digitalis, are
also used as heart medications.
Saponins are natural surfactants, or detergents, found in many
plants, but they are most abundant in the desert plants Yucca
and Quillaja. Extracts from these plants are commonly used as
foaming agents for beverages such as root beer.
Legumes, such peas and soybeans, also contain small quantities
of saponins, which are proving their worthiness as
phytochemicals. In the diet, phytochemical saponins have a
wide spectrum of activity as antifungal and antibacterial agents,
lowering of blood cholesterol, and inhibition of cancer cell
growth. Recent studies have suggested that the low serum
cholesterol levels of Masai tribes in East Africa (who consume a
diet very high in animal products, cholesterol, and saturated fat)
are probably due to the consumption of saponin-rich herbs.
Saponins act by binding with bile acids and cholesterol, so it is
thought that these chemicals “clean” or purge these fatty
compounds from the body, lowering the blood cholesterol
levels.
Some saponins affect the heart and have been used for over 100
years to treat heart conditions. Digitalis is one such saponin and
is derived from the common garden plant, Foxglove. Digitalis
strengthens contractions of the heart muscle and makes it work
more efficiently in people with heart disease. Digitalis-type
saponins can be toxic in high doses and have been used as
arrow and spear poisons by African and South American
natives.
Sulforaphane – It is a naturally occurring sulfur containing
isothiocyanate derivative that helps to mobilize the human
body’s natural cancer-fighting resources and reduces the risk of
developing cancer.
Sulforaphane is a naturally occurring sulfur-containing
isothiocyanate derivative that helps to mobilize the human
body’s natural cancer-fighting resources and reduces the risk of
developing cancer. Within hours of being ingested,
sulforaphane enters the bloodstream where it circulates widely
to trigger the immune system response to carcinogens. The
phytochemical acts by inducing a series of proteins termed
phase 2 detoxification enzymes, which act as scavengers for
cancer-causing molecules before they can damage DNA and
promote cancer.
Broccoli, one of the least popular vegetables, contains relatively
high concentrations of sulforaphane and appears especially
© Copy Right: Rai University
30
beneficial in detoxifying enzymes in the body. The lackluster
appeal of broccoli is probably due to the fact that one-quarter
of the human population contains “supertaster” genes, which
act on the tongue to detect bitterness in this and other similar
Brassica vegetables.
In the past several years, scientists have discovered a new and
highly concentrated source of sulforaphane. A team of
researchers fed three-day old broccoli sprout extracts to groups
of rats previously exposed to dimethylbenzanthracene, a
powerful carcinogen. Rats that received the extracts developed
fewer tumors, and those tumors that did grow on treated rats
had smaller sizes and extended development times. Subsequent
studies have determined that broccoli sprouts contain 20 to 50
times the amount of chemoprotective phytochemicals found in
mature broccoli heads.
The lesson here: eat your vegetables. Regardless of how bitter
they might taste, vegetables will lower your risk of developing
many common cancers, such as malignancies of the breast,
stomach, lung, and prostate gland.
Zeaxanthin - Ounce for ounce, spinach contains more than
twice as much zeaxanthin and more than 60 times as much
lutein as yellow corn.
Zeaxanthin is a yellow-coloured lipid-soluble xanthophyll,
which is also an oxidized hydroxy derivative of beta-carotene.
This biochemical, a strong antioxidant and one of two yellow
carotenoids found in the retina, is abundant in spinach, collard
greens, and corn. It is widely believed that zeaxanthin acts to
filter and shield harmful blue light from the eye and protect
against age-related macular degeneration, the leading cause of
blindness in people over 65.
Popeye, the popular cartoon character known for his timely
consumption of spinach, was correct in his assumption that
this unpopular vegetable is healthy eating. So was mom. Ounce
for ounce, spinach contains more than twice as much zeaxan-
thin and more than 60 times as much lutein as yellow corn.
These carotenoids are now believed to protect against develop-
ment of cataracts, and may have other health benefits as well.
Questions
1. Write a note on Allyl Sulfur Compounds and their role as
nutriceuticals
2. How would chilli peppers be beneficial for health?
3. What role do Saponins play in promotion of good health?
4. Explain why in certain situations the consumption of
vegetables from the brassica family could be detrimental?
5. Write notes on Coumarin and warfarin.
6. How is a natural pesticide in some fruits beneficial to us?
References
1. Halsted, C. H. (2003) Dietary supplements and functional
foods: 2 sides of a coin?Am J Clin Nutr;77(suppl):1001S–
7S.
2. http://micro.magnet.fsu.edu/index.html.
3. Ferguson LR. Role of plant polyphenols in genomic
stability Mutat Res. 2001 Apr 18;475(1-2):89-111.
2D.501