Biosynthesis, Isolation, Characterization, Purification, Structure Identification & Uses of Coumarins :- Umbelliferone Terpenoids :- Cucurbitacin

2. COUMARINS
• W. H. Perkin, the discoverer of the
aniline dyes, first synthesized coumarin in
1868 by the reaction of salicylic aldehyde
and acetic acid anhydride in the presence
of a base.
• It was used in the pharmaceutical
industry as a precursor in the synthesis of
a number of synthetic anticoagulant.

3. CONTD.
• Coumarin is present either in free state or in
glycosidal form, the former being most common.
• Coumarin and others forms like Umbelliferone,
Scopoletin, Scopolin, Aesculetin, Aesculin, etc.
are derivatives of Benzo-α- pyrone.
• Odour - Aromatic smell
• Coumarin is classify in various class such as
simple coumarin, furocoumarin etc.
• It is naturally occur in different family such as
Umbelliferae, Rutaceae, Leguminosae etc.

4. UMBELLIFERONE
• Source: Umbelliferone occurs in many
familiar plants from the Apiaceae
(Umbelliferae) family such as carrot,
coriander.
• Umbelliferone, also known as 7
hydroxycoumarin, hydrangine,
skimmetine, and beta-Umbelliferone, is a
natural product of the coumarin family.
• It is benzopyrone in nature.

5. DIFFERENT SOURCES OF UMBELLIFERONE
NAME BIOLOGICAL
SOURCE
ACTIVE
CONSTITUENTS
USES
Ammi Ammi majus,
Umbelliferae
Xanthotoxin Treatment of
vertigo
Visnaga Ammi
visnaga,
Umbelliferae
Khellin,
visnagin
Coronary
vasodilator.
Carrot Daucus
carota L.,
Umbelliferae
Carotenes,
Vitamin A &
C.
Antioxidant,
Anticancer.
Coriander Coriandrum
sativum,
Umbelliferae
Coriandrol,
Geraniol,
Pinene.
Carminative,
Aromatic,
Stimulant.

6. CHARACTERISATION
• Colour- Yellowish white crystals.
• Taste- Bitter.
• Melting point - 224 − 2270 𝐶
• Solubility- slightly soluble in hot water, but have good
solubility in ethanol.
• Molecular formula - 𝐶9 𝐻6 𝑂3
• Molecular weight- 130g/mol

7. • From Malic acid.
BIOSYNTHESIS

8. ISOLATION
Acacia nilotica

9. CONTD.

10. PURIFICATION
• It can be done by
– HPTLC
– HPLC
– Flash chromatography
– Column chromatography
– Paper chromatography
STRUCTURE IDENTIFICATION
• By using following method:-
– UV spectroscopy
– IR spectroscopy
– Mass spectroscopy
– NMR spectroscopy
PURIFICATION & STRUCTURE
IDENTIFICATION

11. USES
• Sunscreen agent.
• Anti bacterial.
• Antifungal activity.
• Used in diabetes.
• Anti cancer.
MARKETED
PREPERATION

12. TERPENOIDS
• Terpenoids are hydrocarbons of plant origin of the
general formula 𝐶5 𝐻8 𝑛 as well as their oxygenated,
hydrogenated and dehydrogenated derivatives.
• The word terpene is derived from turpentine.
• Terpenoids are regarded as derivatives of polymers of
isoprene.

13. CONTD.
• Terpenes hydrocarbons are classified as
under:
– Isoprene/ Hemiterpene : 𝑪 𝟓 𝑯 𝟖
– Monoterpenes : 𝑪 𝟏𝟎 𝑯 𝟏𝟔
– Sesquiterpenes : 𝑪 𝟏𝟓 𝑯 𝟐𝟒
– Diterpenes : 𝑪 𝟐𝟎 𝑯 𝟑𝟐
– Triterpenes : 𝑪 𝟑𝟎 𝑯 𝟒𝟖
– Tetraterpenes : 𝑪 𝟒𝟎 𝑯 𝟔𝟒
– Polyterpenes : 𝑪 𝟓 𝑯 𝟖 𝒏

14. CUCURBITACINS
• Cucurbitacin is a bitter-
tasting principle that can
be isolated from
members of the family
Cucurbitaceae.

15. DIFFERENT SOURCES OF CUCURBITACINS
NAME BIOLOGICAL
SOURCE
ACTIVE
CONSTITUENTS
USES
CUCUMBER Cucumis
sativus,
Cucurbitaceae
Linoleic acid,
Palmitic acid,
Stearic acid.
Anti bacterial,
Cosmetic
products.
PUMPKIN Cucurbita
maxima(L),
Cucurbitaceae
Cucurbitin,
Unsaturated
fatty acids.
Antioxidant,
Anti diabetic.
WATERMELON Citrullus
lanatus,
Cucurbitaceae
Carotenoids,
Citrulline
Anti
inflammatory,
Improve
digestion

16. BIOSYNTHESIS

17. ISOLATION
Separation & Collection of cucurbitacin
Separated liquid is then extracted with moderately polar solvent like water
Extracted with non polar solvent like chloroform
Liquid containing Cucurbitacin
Pressing
Plant material containing Cucurbitacin
to remove
the waxes,
pigments,
fatty acid
terpenes

18. PURIFICATION
• It can be done by using
– Flash chromatography
– Column chromatography
– Paper chromatography
STRUCTURE IDENTIFICATION
• By using following method:-
– UV spectroscopy
– IR spectroscopy
– Mass spectroscopy
– NMR spectroscopy
PURIFICATION & STRUCTURE
IDENTIFICATION

19. CHARACTERISATION
• Colour- Yellow
• Taste- Bitter
• Molecular Formula- 𝐶32 𝐻44 𝑂8
• Molecular weight- 556.696 g/mol

20. USES
• Anti inflammatory.
• Anti tumour
• Anti-diabetic
• Anti atherosclerotic
• Anti oxidant activity
MARKETED
PREPERATION

21. REFERENCE
• PHARMACOGNOSY-50TH-S-B-Gokhale-P-Purohit-Dr-C-K-Kokate
• https://www.researchgate.net/publication/282672605_Coumarins_-
_An_Important_Class_of_Phytochemicals
• https://www.researchgate.net/publication/236182723_Review_on_Natural_Coumarin_Lea
d_Compounds_for_Their_Pharmacological_Activity
• https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4441156/
– Cucurbitacins – An insight into medicinal leads from nature author Ujjwal Kaushik,
Vidhu Aeri, and Showkat R. Mir
• https://www.researchgate.net/figure/The-structure-of-cucurbitacins-A-The-skeleton-of-
cucurbitacin-A-B-and-D-B-The_fig2_317256161
• https://www.slideshare.net/AswathyJ4/terpenoid-81839641
• https://en.wikipedia.org/wiki/Umbelliferone
• https://en.wikipedia.org/wiki/Cucurbitacin