Occurrence, isolation and characteristic features (Chemical nature, uses in pharmacy, medicinal and health benefits) of Rutin

2. Contents
 Introduction
 Occurrence
 Extraction & Isolation
 Chemistry
 Properties
 Development of Rutin as Phytopharmaceuticals
 Functional properties & Mechanism of Action
 Medicinal and Health Benefits

3. Introduction
 Discovered in 1842 and it has been used in medicine to treat
vascular disorders related to capillary permeability and fragility.
 The concentrations of rutin reported in grapes and buckwheat are
the highest among the other plant species.
 Among the flavonoids, rutin belongs to the flavonols and it is the
glycoside form of quercetin.
 Rutin has significant antioxidant, chelating, and antimicrobial
properties, and therefore many beneficial health effects.

4. Introduction
 Therefore, can be incorporated into functional foods or used in
nutraceuticals and medicinal products.
 Antioxidant and anti-inflammatory effects of rutin have been
extensively studied in neurodegenerative disorders and brain
pathologies in which rutin has demonstrated a potential
neuroprotective role.

5. Introduction
 Rutin is also called vitamin P, which originally described the group
of flavonoids.
 P stands for “permeability” (penetrability), because flavonoids are able
to contribute to reducing the permeability of blood vessels.
 There is not enough scientific data to provide a recommended dose of
rutin. The appropriate dose for you may depend on factors including
age, gender, and medical history.
 The usual recommendation is 250 mg two times a day. Adults using
rutin to treat osteoarthritis may be advised to take 250 mg three times
per day, or every 12 hours.

6. Occurrence
 It was first reported in Ruta graveolens L. (Common Rue)
(Family - Rutaceae) which gave its name to this compound.
 Rutin has been found in the extracts obtained from the skin
of different grape (Vitis vinifera L.) (Family - Vitaceae)
varieties .
 Buckwheat (Fagopyrum esculentum) (Family - Polygonaceae)
is one of the most important commercial sources of rutin.
 However, rutin is not found in cereals and pseudocereals.
Vitis vinifera L. (common grape vine)
Buckwheat

7. Occurrence
 It is present in parts of capers, onions, green asparagus, and sea
buckthorn, among others.
 The content in leaves of St. John’s wort and capers is high and
ranges from 2.4 mg/100 g to 2.7 mg/100g, respectively.
 Some environmental factors such as ultraviolet (UV) radiation may
have also an impact on rutin content

9. Extraction & Isolation
 There are different extraction methods for plant-based rutin, using
different techniques such as ultrasound, microwave,
mechanochemical, infrared, and pressure-assisted methods.
 There is also a high variability in the efficiency of rutin extraction due to
different factors such as the raw material, extraction temperature,
process duration, and solvent-to-sample ratio .
 Phytochemical studies revealed the presence of flavonoidal structure, by
using chromatographic and spectroscopic techniques, 2-(3,4-

10. Identification
 Phytochemical studies can reveal the presence of flavonoidal structure,
by using chromatographic and spectroscopic techniques, 2-(3,4-
dihydroxyphenyl)- 5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1-6)-β-D-
glucopyranosyloxy]-4H-chromen-4-one i.e., rutin is identified.

11. Use Soxhlet apparatus
for extraction with
250ml of 80% ethanol
Filter the extract and
concentrate by
evaporation under
vacuum to about 10
ml
Mix with 25ml
distilled water
Extract with petroleum
ether (50ml X 3) and
then again with
chloroform (50ml X 3) .
After extraction ,
collect the aqueous
layer and leave it to
stand in a cold place
for 72 hours
A yellow precipitate
will separate out
Filter the precipitate
and wash with mixture
of chloroform : ethyl
acetate : ethanol
(50:25:25)
Dissolve the
undissolved part in
hot methanol and
filter
Evaporate the filtrate
to dryness to give
yellow powder
RUTIN

12. Chemistry
 IUPAC Name- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-
O-( 6-deoxy-α-L-mannopyranosyl )-β-D-glucopyranoside
 Molecular Formula- C27H30O16
 Molecular Weight- 610.5 Daltons

13. Chemistry
 Chemical name - quercetin-3-O-rutinoside
 It is a flavonol glycoside that is also known as
vitamin P.
 The phenolic part of the molecule is linked to
sugar (this is the hydrophilic part of the
molecule), increasing the solubility of the
molecule in water.

14. Chemistry
 This characteristic is associated with the
presence in their structures of hydroxyl
groups bound to aromatic rings.
 Rutin also exhibits metal chelating properties,
inhibiting metal-ion-induced peroxidations.
 Quantitative analysis of rutin can be made by
chromatographic methods, mainly high-
performance, thin-layer chromatography and
high-performance liquid chromatography.

15. Physical & Chemical Properties
 Morphology - yellow crystalline powder.
 Melting Point- 125 °C
 Solubility - 0.125 mg/mL in pyridine
 Soluble in alkali but only slightly soluble in water.
 Rutin is Dextrorotatory in neutral and acidic solvent and
levorotatory in alkaline solvents.
 Rutin on hydrolysis yields quercetin, rhamnose and glucose.

16. Development of Rutin as Phytopharmaceuticals
 The low water solubility of rutin (0.125 g/L) represents a limitation to
its incorporation into food supplements or phytopharmaceuticals.
 The stability of rutin to processing conditions, and its possible
interactions with other food components, is also important.
 Rutin has in vitro antioxidant properties.
 Rutin to the development of phytopharmaceuticals has a
disadvantage associated with its low solubility in water, affecting its
bioavailability and absorption.

17. Development of Rutin as Phytopharmaceuticals
 Therefore, nowadays, different techniques have been investigated that
allow the development of phytopharmaceuticals with rutin and at the
same time improve their delivery in the intestinal tract and therapeutic
efficacy, such as the encapsulation of rutin by nanostructured lipid
carriers designed with phosphatidylcholine to form phytosomes that
overcome the low water solubility of rutin.

18. Functional Properties & Mechanism of Action
 Health benefits of rutin can be influenced by its quantity and its
bioavailability for absorption
 Normally, the daily intake of rutin varies between 1.5 and 70 mg/kg
depending on the nutritional habit of an individual
 Rutin is hardly absorbed by intestinal membranes
 Rutin is extensively metabolized at the large intestine where it delivers
quercetin, suggesting that quercetin or rutin metabolites in the colon are
the responsible for quercetin-mediated pharmacological effects.

19. Benefits & Uses
 Rutin is a dietary flavonoid which has many
therapeutic properties, mainly attributed to its
potent antioxidant and anti-inflammatory
activities
 Prevent neurodegenerative disorders,
cardiovascular diseases, and skin cancer

20. Benefits & Uses

21. Neuroprotective Effect of Rutin
 Neuroprotective effect of this flavonoid is one of the most studied
because of the increasing prevalence of neurological disorders and
brain pathologies in the world’s population.
 The brain is very susceptible to oxidative damage and its low levels
of antioxidant protection convert flavonoids, such as rutin, into
potential pharmacological agents due to their antioxidant properties.
 Moreover, inflammation and glial cell activation have been related
with the onset of several neurodegenerative disorders and rutin has
also important anti-inflammatory effects.

22. Neuroprotective Effect of Rutin
 The neuroprotective potential of rutin in terms of its previously mentioned
properties has been evaluated using different animal models and cell
types.
 In several Alzheimer’s disease models, it has been demonstrated that rutin
can prevent cognitive impairment by reducing neuroinflammation and
also inhibiting β-amyloid and cytotoxicity by attenuation of oxidative
stress reduction of TNF-α and IL-1β production in microglia, and by
inhibition of β-secretase enzyme activity.

23. Role of Rutin Mechanism of action Main findings in studies
Antimicrobial
effects
• Inhibits DNA gyrase
• Prevents cytoplasmic
membrane function
• Inhibits energy
metabolism
• In combination of rutin with
morin, quercetin, kaempherol,
myricetin and fisetin against S.
enteritidis, the antibacterial
action gets enhance,
significantly
Anti-arthritic
activity
• Inhibits nitric oxide
production from
macrophages and T-
cells proliferation
• The dual effects of rutin (e.g.,
anti-arthritic and anti-
candidal) is useful as an all-in-
one treatment for septic
arthritis.

24. Role of
Rutin
Mechanism of
Action
Main findings in studies
Antioxidant
activity
• Neutralizes free
radicals
• Chelates transition
metals
• The antioxidant capacity of rutin is
depended on its concentration.
• The inhibitory effect of rutin on the
lipid peroxidation increases with an
increase in its concentration.
Anticancer
activity
• Inhibits cell
proliferation
• Removes reactive
oxygen species
• The tumor size and number of
papillomas significantly decreases
by rutin treatment.
• Level of lipid peroxidase reduces
significantly by rutin treatment

25. Role of
Rutin
Mechanism of action Main findings in studies
Anti-
inflammatory
activity
• Inhibits eicosanoid
biosynthesis, COX,
lipoxygenase and PLA2
activities
• The significant dose
dependent inhibitory effect
of rutin is there
Anti-diabetic
activity
• Enhances the release
of insulin from islets of
langerhans, decreases
in the expression of
resistin, increases in
the expression of PPAR
gene
• Decrease in the fasting
plasma glucose, as well as
increase in insulin levels in
diabetic group after a period
of 45 days' oral
administration of rutin is
there

26. Role of Rutin Mechanism of action Main findings in studies
Anti-allergic
activity
• Inhibits mast cell
activation through
the inhibition of Ca2+
influx, histamine,
leukotrienes and
prostaglandins
release
• By rutin treatment, a
significant increase in mast
cells occurs.
• The reduction of ROS levels in
antigen ± IgE activated mast
cells occurs.
• Histamine released from mast
cells is also inhibited by rutin

27. References
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https://doi.org/10.5958/0974-360X.2020.00447.3
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of Quercetin: A Bioactive Flavonoid. Pharmacognosy Reviews, 10(20), 84.
https://doi.org/10.4103/0973-7847.194044
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Nutritional Supplements, 111–117. https://doi.org/10.1016/B978-0-12-812491-8.00015-1
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