SURNAME: MELANE

NAME: ZINTLE
STUDENT NUMBER: 3858078
MODULE NAME: CHM 321
LECTURE: T MABUSELA
DATE: 30 APRIL 2020
ABSTRACT
A compound consists of two or more elements that are chemically bonded in a fixed
compound.  Prenylated flavonoids are a unique class of naturally occurring flavonoids that
exist especially for the plant's self-defensive strategy. This special class of flavonoids
increases the bioactivities of their backbone flavonoids with non-prenylation; therefore,
prenylated flavonoids have more potential to be developed and utilized. Prenylated
flavonoids are a sub class of flavonoids which combine flavonoids skeleton with a lipophilic
prenyl side chain.
The prenyl-moiety makes the backbone more lipophilic which leads to its high affinity with
cell membrane. The prenylation brings the flavonoids with enhancement of antibacterial,
anti-inflammatory, antioxidant, cytotoxicity, larvicidal as well as estrogenic activities.
However, it is reported that the prenyl-moiety decreases the bioavailability and plasma
absorption of prenylated flavonoids.

INTRODUCTION
The prenylated flavonoid are a sub class of flavonoid, which combine a flavonoid skeleton
with lipophilic prenyl side chain. Flavonoids are quite abundant in nature while prenylated
flavonoids are less common. Prenylated flavonoids have been identified in the 37 of plant
genera. Prenylation usually render flavonoids with improved bioactivities. The mechamism
of action is prenylation increases the lipophilicity of flavonoids which results in higher
affinity to biological membranes and a better interaction with target proteins.

Depending on the length of prenyl side-chain and flavonoid skeletons, prenylated flavonoid
have diverse structures. Flavonoids including chalcones, flavones, flavanones and flavonols
have been found to be prenylated in plant secondary metabolites. In planta prenylated
flavonoids are considered as phyto-alexins which play a key role in physiological processes
when defending against pathogenic microorganisms. As a class of bioactive compounds,
prenylated flavonoids posses a wide range of bioactivities such as estrogenic activity,
antioxidant activity , immunomodulatory activity and anticancer activity, However the
natural abundance of prenylated flavonoids is pretty low, which limits the application of
these bioactive compounds in pharmaceuticals.

In vitro synthesis is a good way to solve this problem , and chemical synthesis is the first
thought coming to a researchers mind. However In most cases chemical synthesis is quite
complicated, has low efficiency and is time -consuming for synthesis of specific prenylated
flavonoids. Harsh synthesis conditions and occurrence of many byproducts make chemical
synthesis difficult to be applied in large scale production. The development of cost-effective
biotransformation techniques in recent years, which uses flavonoids prenyltransferase as a
catalyst agent, makes specific synthesis of prenylated flavonoids possible. The key is to find
an efficient and stable flavonoid prenyltransferase.
NATURAL OCCURRENCE AND STRUCTURAL VARIATION
From the natural preny flavonoids with antioxidants activity most of them are from
Moraceae and Fabaceace families with a limited number of derivatives from Apiaceae,
Asteraceae, cannabaceae, and euphorbiaceae. The most common substitution among the
flavonoid family with antioxidant properties is represented by the 3,3-dimethylally, geranyl,
lavanduyl and famesyl flavones, Flavanones, isoflavones, xanthone-type and other complex
mollecules. As referred before, C-prenylated compounds are more abundant than O-
prenylated ones being most of the O-prenylated flavonoids obtained by synthesis.

Figure 1: shows different types of flavonoid skeleton.

Flavone derivatives are the naturally occurring derivatives were obtained mainly from
Moraceae family, belonging to the Artocarpus and , Dorstenia and cudrania species. All the
natural prenylatedflavones with with antioxidant activity are C-subtituted ,being most of
them mono and di-prenylated.
Flavanones are extremely disseminated in around 42 larger plant families , especially in
compositae,Leguminosae , and rutaceae. Depending on the type of plants , flavanones can
be discovered in all parts of plants above and below the ground, from the vegetative part to
generate organisms : branches ,bark , stem, leaves, flowers, fruits, seeds, rhizomes,
peels,etc. the heterocycle of flavonones also containing a ketone group but there is no
unsaturated carbon-carbon bond. Flavanones lack the double bond between carbon 2 and 3
in the C ring of the Flavonoidskeleton, which is present in flavones and flavonols.
The chemical nature of flavonoids varies according to the hydroxylation pattern, conjugation
between the aromatic rings ,glycosidic moieties, methoxy groups and other substituents.
Flavonoids contain conjugated double bonds and groups(hydroxyl or other substituents)
that can donate electrons through resonance to stabilize free radicals, which originate in the
electronic spectra of flavonoids.

properties of the prenylated flavonoids

Flavonoids have many health benefits and are easy to include in your diet, they have power
antioxidant properties and can help manage symptoms of inflammation. Many plant
products contain dietary flavonoids. Flavanols these are type of flavonoids and are known
for their antioxidant properties. They help manage symptoms of cardiovascular disease.
Flavanols are found in these type of food e.g. onions, kale, grapes and red wine, tea,
peaches, berries, broccoli , scallions etc.
Flavan-3-ols food that have this type of flavonoid are rich in nutrients and they include
white tea, green tea, apples, strawberries, cocoa and chocolate products , black tea , oolong
tea.Flavones are the pigments in blue and white flowering plants. They also work as a
natural pesticide , protecting leaves from harmful insects. Flavones sometimes may help
with the inflammation in the body and can be find in certain foods example parsley, red
peppers, celery, chamomile and peppermint.
Flavanones are known for their anti-inflammatory properties, they may also help you
manage your weight and cholesterol. flavanones are found in these food lemons, limes,
oranges and grapefruit. Isoflavones they help in keeping hormones balanced in your body.
Isoflavonoids are mainly in soy, soy products , and some other legumes such as fava beans.
Anthocyanins are naturally produced pigments that give their red, purple, and blue colour.
They are predominantly found in the outer skin of berries and berry products like red and
purple graped, red wine, cranberries, blueberries, strawberries and blackberries.
Flavonoids help regulate cellular activity and fight off free radicals that cause oxidative
stress on your body. They help your body function more efficiently while protecting it
against everyday toxins and stressors. Flavonoids are powerful antioxidants agents,
Antioxidants help your body fight off potentially harmful molecules that can be introduced
to the body. The body produces antioxidants naturally, but they are also found in the dark
chocolate, legumes, and many fruits and vegetables. Inflammation is one of your bodys
immune responses, allergens, germs, toxins and other irritants can trigger inflammation that
results in uncomfortable symptoms. Flavonoids may help your body dismiss that
inflammatory reaction so that those symptoms are reduced.
HEALTH BENEFITS OF PRYNYLATED FLAVONOIDS AND MEDICINAL PROPERTIES
Different flavonoids can be used to help the body in different ways. For one including foods
with flavonoids in your diet may be an effective way to help manage high blood pressure .
five subtypes of flavonoids have a demonstrable effect on lowering high blood pressure,
according to a review that was published in 2015. The flavonoids found in tea, coffee, and
soy may help lower your risk of having heart attack or stroke, people that consume higher
levels of flavonoids as part of their diet have lower risk of experiencing cardiovascular
events. A diet high in flavonoids may also decrease your risk of type 2 diabetes. A high
intake of dietary flavonoids correlates with a lower risk of type 2 diabetes. However more
research is needed to prove the efficacy of flavonoids as blood sugar regulators. The anti-
inflammatory and antioxidant effects of flavonoids have also encouraged researchers to
study their potential as anticancer drugs. It has been shown that certain flavonoids may help
stop cancer cells from multiplying, including foods with flavonoids and keeping a healthy
diet may decrease your risk of getting certain cancers.
Flavonoid modified drugs have much better effect on lung cancer cell line. Allium flavum and
allium carinantum are wild, edible onions rich in flavonoid, rutin, etc. these besided having
known antioxidant potential are effective anti-cancer agents. Dietary flavonoids shows a
favourable relationship between their consumption and reduction of cardiovascular
diseases. It has been shown that those who consume a large number of flavonoids have
18% lower mortality risk of cardiovascular diseases. Flavvonoids have cardioprotective and
neutroprotective actions and chemoprotective abilities. Tea is a rich source of flavonoids
and its intake reduces the risk of cardiovascular diseases. High consumption of these
flavonoids decrease arterial stiffness which reduces the risk of cardiovascular diseases.
Morin hydrate showed high biological activity such as anti-inflammatory , anti-cancer, and
protection against cardiovascular diiseases. Brazil nuts are rich in flavonoids which help
prevent heart disease and cancer . chrysin is a flavone and has beneficial effects on epilepsy
and depression and also suppresses neuro-inflammation and has neuro-protective effects.
The effects of flavonoids on nervous system they prevent age related neurodegenerative
diseases and in particular, dementia , parkinsons and Alzheimer disease.
The ROS and nitrogen species have roles In many neurodegenerative disorders such as
parkinsons disease.Foods which have abundant amounts of flavonoids lower the hazard
neurodegenerative and also counteract age related cognitive disorders. It is beneficial in
two ways first it regulates neuronal signal cascade caused by cell apoptosis and secondly
shows beneficial effects on the peripheral and central nervous system. Excessive drinking of
alcohol causes various health disorders and negatively affects the brain. The
acetylpectolinarin(ACP) flavonoid obtained from linaria vulgaris mill has been reported to
treat hangover by increasing the spontaneous network function of the cultured
hippocampal neurons when treated with low concentration of ethanol.
Hyperalgesia is an enhanced pain sensation due to peripheral nerve damage and is
associated with diabetic patients. Quercetin and sodium when used together can act as
antinociceptives decreasing diabetes complications. Cisplatin induced hyperalgesia can also
be reduced by 6-methoxyflavone. Flavonoid can be used to prevent stroke chalcones which
are precursor compounds of flavonoids and iso-flavonoids. They are present in various
plants and vegetables with a wide range of biological activities. Chalcone is an aromatic
ketone and an enone with an ability to activate nuclear factor erythroid 2-related factor
pathway.
The increase and spread of multi-drug resistance in pathogenic bacteria resulted into a
number of antibiotics that have become ineffective for the treatment of a number of
bacterial infections. Flavonoids have the ability to enhance the protective immune systems
of humans. Several flavonoids act both as bacteriostatic and bactericidal agents by
damaging the cytoplasmic membrane, and inhibiting energy metabolism and nucleic acid
synthesis of microorganisms . bridelia is a plant of genus of Phyllanthaceae family, which is
used as a pain-relieving medicine in Asia and South Africa. Its extract contains flavonoids like
quercetin, gallocatechin, epigallocatechin, myricetin-3-glycosides, and isoflavone. These
flavonoids are responsible for its antimalarial, antibacterial, anti-inflammatory activities.
Anthocyanidin plays an important role against tuberculosis and drug-
resistant Mycobacterium tuberculosis strains.
It is found that cranberry flavonoids decrease the blood glucose levels and increase insulin
sensitivity in animals. Anthocyanins control obesity and consequently can also help in the
prevention of type 2 diabetes. Chrysin is natural flavone having many health benefits such
as antidiabetic, antiallergic, anticancer, and antitumor effects. Many flavonoids are anti-
diabetic by increasing secretion of insulin, improvement of hyperglycemia, reduce resistance
to insulin and increase uptake of glucose by skeletal muscles in murine model. Flavonol rich
chocolate enhances insulin sensitivity and reduce insulin resistance in healthy
subjects. Allium cepa L. (onion) flesh and skin are rich in quercetin derivatives and display
protein tyrosine phosphatase 1B (PTP1B) inhibitory activity, decreases its expression, and
increases glucose uptake making it a potential antioxidant and antidiabetic.
Figure 2:C-prenylated flavonoids with potential cytotoxic activity against solid tumour
BIBLIOGRAPHY
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