UNIT IV

PLANT BITTERS & SWEETENERS

CHIRATIN
Chiratin is a white crystalline neutral and tasteless.

It is steroidal glycoside (positive test for Libbermann

Burchard)

Melting point 266-2680C

ROTENONE
Rotenone is an odourless, colorless crystalline isoflavone.

It is used in powder form to treat scabies and head lice on humans

and parsitic mites

It has been used as an organic pesticide dust for gardens.

MOA : it acts by interfering with electron transport chain in

mitochondria

It inhibits the transfer of electron from iron-sulfur centres in complex I

to ubiquinone. This interferes with NADPH during the creation of
usable cellular energy (ATP). Complex I is unable to pass off its
electron to CoQ, creating a backup of electrons within the
mitochondrial matrix .

Cellular oxygen is reduced to the radical, creating a reactive oxygen

 NARINGIN
It is a flavanone-7-O glycoside between the lavanone naringenin and the
disaccharide neohesperidose

It is occur naturally in citrus fruit especially in grapefruit where naringin is

responsible for fruits bitter taste

In commercial grapefruit juice production , the enzyme naringinase can be

used to remove the bitterness created by naringin.

In humans the naringin is metabolised to the flavanone naringenin

When naringin is treated with potassium hydroxide or another strong base,

naringin get hydrogeneted and produce naringin dihydrochalcone, a compound
roughly 300-1800 times sweeter than sugar.
Biological activity:

It inhibits drug metabolising cytochrome P450 enzymes including CYP3A4 &

CYP1A2, which may result in drug drug interction
It affects intestinal absorption of certain drugs(either increase or decrease)
Other pharmcological effects
1. An inhibitor of endothelial growth factor release, which causes angiogenesis.
2. Reduces diabetes –induced neuropathy in rats.
3. Showed protective effects against cognitive dysfunction & oxidative damage
 LIMONIN
It is a cyclic terpene, colourless
The more common d-isomer posses strong smell of oranges
It’s a chiral molecule , biological sources produce one enantiomer.
Mainly present in citrus fruit contains d-limonene
D-limonene is obtained commercially from citrous fruits through two primary methods:
1. Centriffugal separation
2. Steam distillation
Racimic limonene is known as dipentene.

Chemistry
It is a stable terpene & can be distilled without decomposition
At elevated temparature it cracks to form isoprene
It oixidize in moist air to produce carveol, carvone and limonene oxide.
With sulphur it undergoes dehydrogenetion & produce p-cymene

Biosynthesis
Limonene is formed from geranyl pyrophosphate by cyclization of aneryl carbocation
Biological properties
Act as dietary chemotherapeutic agents
In the treatment of gliomas

Uses

In cosmetic products (as hand cleanser to give a lemon orange fragrance)

As flavouring agent
As a fragrance in perfumery (after shave lotions, bath products)
As botanical insecticide
Relieve gstroesophageal reflux & in heart burn.
As a solvent for filament(as it is combustible) fused 3D printing
Also consider as biofuel
 SWEETNEWRS
• Sweetening agents are the substances which are added to a
drug
formulation to mask its bitter taste.
• Sugar is the most widely used natural sweetening agents.
• It imparts viscosity to drug and also even act as preservative
for liquid
dosage form.
• Sugar having lot of disadvantages like dental caries, high blood
sugar, calories etc.
• Among this there are various substitute available over sugar.
• There are 2 types of substitute which are used as sweeteners,
1) Natural sweeteners
 CLASSIFICATION OF SWEETNERES
• The sweeteners are classified on their
nutritive
values
A. Nutritive Sweeteners
B. Non Nutritive sweeteners
 NUTRITIVE SWEETNERES
• Alternative nutritive sweeteners are sugar alcohol
such as
Sorbitol, Mannitol, Lacitol etc.
• It having properties like less sweet and less calories
• FRUCTOSE- 4Kcal/gm the same as sucrose and it
doesn't cause fluctuation in blood sugar, thus better
choice for diabetic patients.
• 1.5 times sweeter than sugar and cost effective for
food
industry.
 NON NUTRITIVE SWEETNERES
• Examples include Aspartame, Saccahrin,
Clycamate, Alitame etc.
• More sweeter and thus only small quantity is
required
for sweetening food preparation.
• It is the artificial sweeteners.
 SWEETNERS FROM NATURAL ORIGIN
• Thaumatin (Thaumatococcus danielli)
• Stevioside and Rebaudioside (Stevia
rebaudiana)
• Neohesperidin (Citrus aurantium)

OTHERS
• Glycyrrhizin
• Monellins
• Sucralose
 THAUMATIN
Synonym: Talin

Thaumatin is the common name for a mixture of potently sweet proteins that
can be extracted from the West African plant Thaumatococcus daniellii
(Bennett), known locally as the katemfe berry.
Family : Marantaceae
Characteristics:
Highly soluble in water
3500x >> Sucrose
It’s sweetness show a delayed onset and long persistant
liquorice like taste.
It’s a mixture of proteins. A total of 5 isomers are found
Thaumatin I
Thaumatin II
Thaumatin III
Thaumatin a
Thaumatin b
Each with almost identical molecular weight of 22,000 Daltons. Thaumatins I
and II have very similar amino acid sequences, differing only in five residues
The protein is stabilized by eight disulphide bridges, thus conferring a greater
stability to heat and pH denaturation to the molecule than might be expected
for a protein.
Thaumatin was used as a tool in early studies that sought to understand the
structure of the mammalian receptor for sweetness
The temporal taste profile of Thaumatin is characterised by a delay in perceiving
sweetness.
 Physical and chemical properties
Thaumatin is stabilized by the eight disulphide bridges that result in a cross- linked network of amino
acid chains. This confers a measure of stability to heat and extremes of pH.
These disulphide bridges are also responsible for holding the protein chain in the correct conformation
to elicit sweetness, as has been confirmed by demonstrating that cleavage of a single disulphide
bridge results in loss of sweetness.
It is highly water soluble, stable to heating and stable under acidic conditions
Cream coloured powder, POSITIVE TO NINHYDRINE TEST ( purple color)

Applications
The main commercial applications for Thaumatin its claimed flavor modifying and enhancing
functionalities.
Thaumatin has found application in liquid medicines.
The oral care products and in the nutraceutical/fortified foods industries.
Increasing concentrations of Thaumatin appear to have increasing effects on the bitterness
associated with vitamin B complex preparations, caffeine and soybean peptides.
Suitable for diabetic patients
 Safety

Thaumatin was studied for its sub-acute toxicity in rats and dogs and
its ability to produce anaphylactic antibodies following oral
administration to rats and normal human subjects.
Also, it was shown to be non-teratogenic when administered orally to
rats at 0, 200, 600 and 2000 mg/kg body weight/day from day 6 to 15
of gestation and was without effect on the incidence of dominant
lethal mutations when administered on five consecutive days to
male mice at 200 and 2000 mg/kg per day.
 STEVIOSIDE AND REBAUDIOSIDE
• Biological Source: It is extracted from a South American plant
Stevia rebaudiana Berrtoni
• Family: Compositae
• Characteristics:
1. The dried leaves of the plant, the water extract of the leaves
and the purified ingredients of extract are used as
sweetening agents.
2. It’s tainted with a bitter and undesirable after taste.
3. No side effects.
4. Both are diterpene Glycosides.
It is origin of Paraguay and Brazil. Stevia is cultivated primarily in
USA, Canada, Korea, Japan, Taiwan, china, and United Kingdom.
In September 1995 the USA FDA allowed Stevia and it is extracted
to be imported as a food supplement but not as a sweetener.
Major food companies like coca cola and beatrice foods used
Stevia extracts to sweeten the foods for sale in Japan, Brazil and
other countries.
The plant grows up to range 65-180 centimeters when cultivated or
growing naturally in fertile soil. It is a short day plant and flowering
from January to March in the southern hemisphere. The suitable
natural climate is semi humid subtropical with temperature
extremes from 21 to 43°C.
The steviol glycoside sweeteners share a common aglycone, steviol.
Linked to steviol are carbohydrate moieties and it is the number
The biosynthesis of the glucosides Sweetness potencies of steviol
occurs only in green tissues. Steviol
glycosides
Compound Relative sweetnessa
produced in the plastids & in the
endoplasmic reticulum catalyzed by UDP-
Stevioside 300
glucosyltransferases. Rebaudioside , is a
particular form of stevoside. The Rebaudioside A 250-450
glycosides are then stored in vacuoles.
Rebaudioside B 300-350

Rebaudioside C 50-120

Rebaudioside D 250-450

Rebaudioside E 150-300

Dulcoside A 50-120

Steviolbioside 100-125
 Physiological properties
 rebaudiana A leaves contain diterpene glycosides (stevioside and the rebaudiosides) 300
times sweeter than sucrose with superior solubility in water and a positive taste profile that
are safely metabolized by the body without any side effect.
 Rebaudioside A in the digestive tract is first metabolized by microbes in the colon to
stevioside which is further converted into glucose molecule and steviol. The released
glucose molecule is used by the bacteria in the colon and is not absorbed into the blood
stream.
 Steviol glycosides are not readily absorbed from the upper small intestine of the rat or
human following oral administration. As human digestive enzymes do not hydrolyse β-
glycosidic linkages, digestion in the small intestine is limited. Microbial fermentation occurs
in the large intestine of both rat and human, releasing the aglycone steviol. Steviol is then
absorbed conjugated with glucuronic acid and excreted as steviol glucuronid.
 Study also showed that the majority of steviol glycosides are absorbed and glucuronidated in
the liver. The newly bonded glucuronidate is released in the blood and filtered by the kidneys
into the urine. Small amounts of glucuronide that remain in the colon are excreted through
fecal matter.
Applications
,
 In Korea, stevioside is an accepted sweetener in baked products, table-top sweeteners,
beverages and seasonings.
 steviol glycoside sweeteners have acceptance across the range of food and beverage
applications normally associated with the use of high-potency sweeteners.
 The US Food and Drug Administration (FDA) announced in December 2008 that it had no
objection to the use of rebiana in food and beverages in the United States.
 NEOHESPERIDIN DIHIDROCHALCONE
(NHDC)
• Biological source: It is a flavonoid compound present in the bitter
orange Citrus aurantium Var amara
• Family : Rutaceae
• Characteristics:

1. It is characterized by pronounced Menthol like taste which limits its

use.
2. It act synergistically with other sweetners.
3. It has flavor enhancing system.
Neohesperidin dihydrochlcone, a compound roughly 1500-1800 sweeter than
sugar at threshold concentration. In pure form it is a white substance.

Strength around and above 20ppm it can produce side effects such as nausea
and migrain.

In food it is used as flavour enhancer in concentrations of around 4-5 parts per

million (ppm)

It is well known for synergistic effects when used in conjugation with other
artificial sweeteners.

As a flavour enhancer, NHDC is used in a wide range of products and is indicated

by the E number E 959

It reduces the bitterness of pharmaacological drugs in tablet form.

 END OF UNIT IV

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