Coumarin and It's Derivates

6/14/2017
Coumarin and it’s

Derivates
naturachem67@gmail.com
1
6/14/2017
• Coumarins are a group of polyphenolic compounds which isolated for the

first time from plant product Tonka bean (Dipteryx odorata Willd, Fabaceae),
coumarou in 1820.
(Bruneton J (1999) Pharmacognosy, Phytochemistry, Medicinal Plants Second Edition, Hampshire UK, Intercept, pp. 263-277.)
• The word tonka for tonka beans is taken from the Galibi (Carib) tongue spoken by
natives of French Guiana (one source for the plant); it also appears in Old Tupi,
another language of the same region, as the name of the tree. The old genus
name, Coumarouna, was formed from another Tupi name for tree, kumarú. The
French word for the tonka bean, coumarou, is from this name.
• Coumarin, named for coumarou was first isolated from Tonka beans and sweet clover
in 1820 by A. Vogel of Munich, who initially mistook it for benzoic acid.[1][2]
• Also in 1820, Nicholas Jean Baptiste Gaston Guibourt (1790–1867) of France
independently isolated coumarin, but he realized that it was not benzoic acid.[3]
• In a subsequent essay he presented to the pharmacy section of the Académie Royale
de Médecine, Guibourt named the new substance "coumarine".[4][5]
• In 1835, the French pharmacist A. Guillemette proved that Vogel and Guibourt had
isolated the same substance.[6]
• Coumarin was first synthesized in 1868 by the English chemist William Henry
Perkin.
2
6/14/2017
• [1] Vogel, A. (1820). "Darstellung von Benzoesäure aus der Tonka-Bohne und aus den Meliloten- oder
Steinklee-Blumen" [Preparation of benzoic acid from tonka beans and from the flowers of melilot or sweet
clover]. Annalen der Physik (in German). 64 (2): 161–166. doi:10.1002/andp.18200640205.
• [2] Vogel, A. (1820). "De l'existence de l'acide benzoïque dans la fève de tonka et dans les fleurs de
mélilot" [On the existence of benzoic acid in the tonka bean and in the flowers of melilot]. Journal de
Pharmacie (in French). 6: 305–309.
• [3] Guibourt, N. J. B. G. (1820). Histoire Abrégée des Drogues Simples [Abridged History of Simple Drugs]
(in French). 2. Paris: L. Colas. pp. 160–161.
• [4] "Societe du Pharmacie de Paris". Journal de Chimie Médicale, de Pharmacie et de Toxicologie. 1: 303.
1825. … plus récemment, dans un essai de nomenclature chimique, lu à la section de Pharmacie de
l'Académie royale de Médecine, il l'a désignée sous le nom de coumarine, tiré du nom du
végétal coumarouna odorata … [… more recently, in an essay on chemical nomenclature, [which was] read
to the pharmacy section of the Royal Academy of Medicine, he [Guibourt] designated it by the name
"coumarine", derived from the name of the vegetable Coumarouna odorata …]
• [5] Guibourt, N. J. B. G. (1869). Histoire Naturelle des Drogues Simples (6th ed.). Paris: J. B. Baillière et fils.
p. 377. … la matière cristalline de la fève tonka (matière que j'ai nommée coumarine) … [… the crystaline
matter of the tonka bean (matter that I named coumarine …]
• [6] Guillemette, A. (1835). "Recherches sur la matière cristalline du mélilot" [Research into the crystalline
material of melilot]. Journal de Pharmacie. 21: 172–178.
• Coumarins belong to a group compounds known as the benzopyrones, all of

which consist of a benzene ring joined to a pyrone. Coumarin and the other
members of the coumarin family are benzo-α-pyrones
COUMARIN / BENZO-α-PYRONES
3
6/14/2017
• Coumarin covers a very wide range of compounds throughout the plant

kingdom and are found rich in fruits, roots, stems and leaves.
• They are rich in cassia leaf oil, lavender oil and cinnamon bark oil. Richest
sources are found in Rutaceae and Umbelliferone.
• Coumarins are also found in selective microorganisms. Members of
coumarins isolated from microbial sources are novobiocin from Streptomycin
and aflatoxin from Aspergillus species.
Biosynthesis of Coumarin and it’s Derivates
4
6/14/2017
Like other phenylpropanoids, coumarins arise from the metabolism of

phenylalanine via a cinnamic acid, p-coumaric acid (Shikimic Pathway)
Coumarin Sub-types
• There are 7 main coumarin sub-types:
• the simple Coumarins,
• Furanocoumarins,
• Pyranocoumarins
• Benzocoumarins
• Furanobenzocoumarins
• Isocoumarins, and
• Pyrone-substituted coumarins.
5
6/14/2017
COUMARINS
• The simple coumarins (e.g. coumarin,7-hydroxycoumarin and 6,7-
dihydroxycoumarin), are the hydroxylated, alkoxylated and alkylated
derivatives of the parent compound, coumarin, along with their glycosides
Simple Coumarins
Coumarin Dihydrocoumarin
Umbelliferone Aesculetin Scopoletin

(7-hydroxy (6,7 – dihydroxy (6-methoxy-7-hydroxy-
coumarin) coumarin) coumarin)
6
6/14/2017
FURANOCOUMARINS
• Furanocoumarins consist of a five-membered furan ring attached to the
coumarin nucleus, divided into linear or angular types with substitution at
one or both of the remaining benzoid positions
7
6/14/2017
8
6/14/2017
PYRANOCOUMARINS
• Pyranocoumarins members are analogous to the furanocoumarins, but
contain a six-membered ring.
2’,2’ – dimethylxanthyletin (2’,2’ – dimethylpyran-5’,6’ : 6,7-coumarin)
Seseline type
Visnadin
9
6/14/2017
BENZOCOUMARINS
• Benzocoumarins contain a benzene ring condensated to coumarin at 3,4-
carbon atoms.
Ellagic acid 3,4 - benzocoumarin

10
6/14/2017
FURANOBENZOCOUMARINS
• Furanobenzocoumarins contain benzofuran condensated to coumarin at
3,4-carbon atoms
naturachem67@gmail.com Coumoestrol
ISOCOUMARINS
• Isocoumarin is a isomer of coumarin
11
6/14/2017
PYRONE-SUBSTITUTED COUMARINS
• Coumarins substituted in the pyrone ring include 4-hydroxycoumarin

(Keating et al, 1997). The synthetic compound, warfarin, belongs to this
coumarin subtype.
12
6/14/2017
13
6/14/2017
14
6/14/2017
Physical and chemical properties of

Coumarins
• They occur as colourless crystals. Coumarins have a characteristic fragrant
odour and bitter, aromatic and burning taste.
• They are soluble in ethanol, methanol, chloroform, fatty oil, alkaline water
solution.
• In ammoniacal solution these compounds have a blue, blue-green or violet
fluorescence. The fluorescence is marked if examined in filtered
Ultraviolet light and is used for the chlomatographic visualization of the
compounds.
• Studies have proven that coumarins act as competitive inhibitors of vitamin K.

Other intricate compounds are based on the coumarin nucleus which comprises of
the anticoagulants like warfarin, aflatoxins and the psoralens.
(Hoult JR1, Payá M (1996) Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen
Pharmacol 27:713-722.)
• Studies have also shown that they function as blood diluting agent and also exhibits
anti-fungicidal property. Researches have also proved the selective cytotoxicity of
coumarins for tumor cells and also the effect of coumarins in the regulation of
immune response, cell growth and differentiation.
(Vianna DR, Hamerski L, Figueiró F, Bernardi A, Visentin LC, et al. (2012) Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-
oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species. Eur J Med Chem 57: 268-274.)
• Nowadays, coumarins are also used as additives in food and cosmetic industry, as
laser dyes, agrochemical industries and also as optical brightening agents. Studies
have proven that it possesses anti-aging, and cardioprotective function.
15
6/14/2017
Coumarins and it’s Therapeutic role
16

Coumarin and It's Derivates

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Coumarin and It's Derivates

Uploaded by

Copyright:

Available Formats

6/14/2017

Coumarin and it’s

• Coumarins are a group of polyphenolic compounds which isolated for the

• Coumarins belong to a group compounds known as the benzopyrones, all of

• Coumarin covers a very wide range of compounds throughout the plant

Biosynthesis of Coumarin and it’s Derivates

Like other phenylpropanoids, coumarins arise from the metabolism of

Umbelliferone Aesculetin Scopoletin

2’,2’ – dimethylxanthyletin (2’,2’ – dimethylpyran-5’,6’ : 6,7-coumarin)

Ellagic acid 3,4 - benzocoumarin

• Coumarins substituted in the pyrone ring include 4-hydroxycoumarin

Physical and chemical properties of

• Studies have proven that coumarins act as competitive inhibitors of vitamin K.

Coumarins and it’s Therapeutic role

You might also like