ALCH 20

Cis-Trans isomerism cooking tomatoes

and healthy hearts

Name

: Nursyaqira Binti Ramle (1411170632)

Nur Shahirah binti Mat Akhir (1411170626)

Class

: Coventry

Lecturers
Name : Miss Rawaida Aqilah Binti Abdul Rahim
6

Content

Content

Page

Acknowledgment

(i)

Introduction

(ii)

Cis-Trans isomerism cooking tomatoes

and healthy hearts

1-5

Conclusion

Reference

Acknowledgement

In performing our assignment, we had to take the help and guideline of some respected
persons, who deserve our greatest gratitude. The completion of this assignment gives us much
pleasure. We would like to show our gratitude to Miss Rawaida for giving us a good guideline
for assignment throughout numerous consultations. We would also like to expand our deepest
gratitude to all those who have directly and indirectly guided us in writing this assignment.

Many people, especially our classmates and team member itself, have made valuable
comment suggestions on this proposal which gave us an inspiration to improve our assignment.
We thank all the people for their help directly and indirectly to complete our assignment.

Introduction
This present study aims to evaluate the beneficial effect of tomatoes, a rich source of
lycopene, which is a relatively new carotenoid known to play an important role in human health
and disease.
There is a history behind this tomatoes.Tomatoes are one of the most popular fruits.
Although found in the vegetable section of your supermarket in botanical terms tomatoes are in
fact

fruit

grown

from

vine.

The Aztecs and Incas first cultivated tomatoes in 700AD; they were then introduced to
Europe by the Mexicans in around 1556. It actually took some time for the Spanish to accept the
tomato for fear that it was poisonous like other members of the nightshade family. Later down
the line, however, some tomato advocates claimed the fruit to have aphrodisiac powers that is
why the French called them Pommes damour meaning love apples. Tomatoes are now eaten
freely throughout the world, and are believed to have numerous health benefits.

There are around 7500 different varieties of tomato, all grown for different purposes,
some more resilient to pests, others more flavourful. While to the common supermarket shopper
red tomatoes and the odd green unripe tomato are all that is available, there is also a rainbow of
colours grown by some cultivars, ranging from yellow, orange, pink, black, ivory, white, and
purple as well as different shapes and sizes; cherry, plum, pear and beefsteak.
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HSW : Cis-Trans isomerism cooking tomatoes and healthy hearts

In organic chemistry, cis/trans isomerism (also known as geometric isomerism) is a form

of stereoisomerism describing the relative orientation of functional groups within a molecule.
Cis and trans isomers occur both in organic molecules and in inorganic coordination complexes.
The terms cis and trans are from Latin, in which cis means "on this side" and trans means
"on the other side" or "across". The term "geometric isomerism" is considered an obsolete
synonym of "cis/trans isomerism" by IUPAC.
Example :

Biological system are often very sensitive to different geometric isomer. Based on
research, show that the antioxidant lycopene is very effective to prevent a variety of problem
such as heart disease, atherosclerosis and cancer on prostate, breast, lung, bladder, ovaries, colon
and pancreas. Lycopene is also used for treating Human Papilloma Virus (HPV) infection, which
is
10 a major caused of uterine cancer. Some people also used lycopene for cataracts and asthma.
Lycopene works as a powerful antioxidant that may help protect cells from damaged. This is
why, there is a lot of research interest in lycopenes role in preventing cancer.

Lycopene naturally gives fruits and vegetables a red colour because the presence of
pigment called carotenoids. Lycopene is found in watermelons, pink grape fruit, apricots and
pink guavas. It is particularly high amounts in tomatoes and tomato product. In North America,
85% of dietary lycopene comes from tomato products such as tomato juice or paste. Processing
raw tomatoes using heat (in making of tomato juice, tomato paste, and ketchup) actually changes
the lycopene in the raw product into a form that is easier for the body to used.
Scientists have found that cooked tomatoes seemed to be more biologically active that the
raw tomatoes even-though they have the similar lycopene levels. Trans-lycopene, a straight chain
molecule is the dominant isomer found in most red tomatoes, but biologically active form found
in the human body is cis-lycopene (bent molecule).

Scientist are not sure whether the body converts one isomer into another using an enzyme of
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whether
cis-isomer is absorbed into the body more easily. Nevertheless, they discovered that

cooking tomatoes can alter the ratio of trans:cis isomers in the fruit from 19:11 to 11:19. If the
cis-isomers in the fruit is more, the more readily the lycopene is absorbed and more benefit to

the body. Therefore, we should cook our tomatoes thoroughly before we eat them for maximum
benefit.
Researchers from Cornell University , USA, said that cooking the tomatoes
increase the level of phytochemicals they contain, although it also reduces the amount of vitamin
C found in the vegetables. Writing in the latest issue of the Journal of Agriculture and Food
Chemistry Rui Hai Liu, Cornell assistant professor of food science, said this research
demonstrates that heat processing actually enhance the nutritional value of tomatoes by
increasing the lycopene contain that can be absorbed by the body as well as the total antioxidant
activity. While the antioxidant activity in tomatoes is enhance during the cooking process,
vitamin C loss occurs when the foods ascorbic acid is oxidised to dehydroascorbic acid and the
other form of nutritionally inactive components. Lycopene is the most efficient single oxygen
quencher and devours more than 10 times more oxygenated free radical than Vitamin E, Cornell
researchers said. Therefore, cis-lycopene in cooked tomatoes is better than trans-lycopene in the
raw one.
On the other hand, studies show that, tangerine tomatoes is better than common red
tomatoes. Tangerine tomatoes, named for their attractive orange colour, are plump, juicy and
slightly sweeter than ordinary red tomatoes. The difference lies in the form of lycopene that the
two tomato types provide. The trans-lycopene form makes up most of the lycopene in common
red tomatoes. In contrast, most of the lycopene in tangerine tomatoes is tetra-cis-lycopene. For
the California study, 21 healthy men and women volunteers were asked not to eat any fresh
tomatoes,
tomato products or other food rich in lycopene other than that provided by other
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researchers that instruct when into effect at the start of a 1 week washout period and stay in
effect throghout the rest of the study period. In the week after the washout, volunteers ate their

usual breakfast, dinner and snack (minus lycopene rich food), but came to the ARS Western
Human Nutrition Research Centre in Davis to have a special lunch which is tangerine tomato
sauce.
Blood was analysed weekly for lycopene level with a standard labaratory instrument known
as a high perfomance liquid chromatograph. The analysis indicate that lycopene levels increase
relative to does measures just before each one week of special lunch. Total lycopene level
increase more after the tangerine tomato treatment than the red tomato treatment. Thus, tangerine
tomatoes contain tetra-cis-lycopene rich may be able to improve our health.
Another case study from Ohio State University, USA state that Lycopene, the predominant
carotenoid in tomatoes and tomato products responsible for the red colour, has attracted
considerable attention as epidemiological evidence continues to suggest that it may provide
protection against a number of cancers and other degenerative diseases. The observation that
serum and tissue lycopene consists of between 50% and 90% cis-lycopene isomers, whereas
tomatoes and tomato-based products contain mainly all-trans-lycopene, has led to the hypothesis
that cis-isomers of lycopene are produced during food processing, cooking, or digestion or are
more bioavailable. Improved absorption of lycopene cis-isomers is hypothesised to result from
greater solubility in mixed micelles and a lower tendency to aggregate, a hypothesis supported
by rodent studies.
Although most commercially processed tomato products such as juice, paste, soup and
ketchup contain a relatively low percentage of cis-isomers (10 %), aggressive food processing or
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cooking has been shown to increase cis-isomer content. The greatest increase in cis-isomer
formation was observed when tomato products were heated in the presence of oil. Thus, research

conducted so far suggests that lycopene cis-isomer formation is usually not observed at the mild
temperatures commonly employed in most commercial food processing but is enhanced by the
presence of oil at medium or higher processing and cooking temperatures.
The presence of elevated levels of lycopene cis-isomers in human biological samples
compared with fresh tomatoes may also have biological significance, but this remains
speculative. Cis-isomers may show unique tissue biodistribution patterns or perhaps distribute
differently within cellular compartments to influence cell functions and responses to
physiological or toxic stimuli in the external or intracellular environment. Thus, it is
hypothesised that modification of the cis- and trans-lycopene-isomer pattern of foods may allow
investigators to achieve targeted changes in absorption and distribution of specific carotenoid
isomers in order to influence biological effects and health outcomes.
The objective of the present study was to develop two similar tomato sauces with
high and low cis-lycopene-isomer content by different processing techniques. Therefore, cislycopene has more benefit than trans lycopene.

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Conclusion

The facts about tomatoes definitely point them out to be a powerhouse of nutrients to be
enjoyed as often as possible. Tomatoes contain masses of vitamin C and are a rich source of
vitamins A and B, as well as potassium, iron, phosphorus and fibre. Of course not forgetting the
commonly known huge amount of lycopene that tomatoes contain which has been associated
with

reduced

risk

of

some

cancers.

Lycopene is an antioxidant found in the cell walls of the tomato and is what makes them
red, it is part of the carotenoid family which are natural compounds that create the colours of
fruits and vegetables. Lycopene has been making headlines of late because of its anticarcinogenic properties, the research all indicate that lycopene in tomatoes increases when
tomatoes are cooked, this is because when a tomato is cooked the cell wall ruptures and releases
more

lycopene.

A.

To sum it up, yes tomatoes do contain more lycopene when cooked however other
valuable nutrients which are equally as valuable are lost during the heating process, like most
raw foods the lycopene contained in the raw tomato is probably a sufficient amount thus twice as
much lycopene and none or less vitamin C, B1 and B6 is probably not a good trade off.
Additionally the lycopene content can be increased simply by blending tomatoes, therefore no
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need for heating or nutrient loss.

Reference

http://www.ncbi.nlm.nih.gov/pubmed/17453080
http://www.cancer.org/treatment/treatmentsandsideeffects/complementaryandalternativem
edicine/dietandnutrition/lycopene
http://www.therawgreek.com/tomato-a-go-go