Medicinal plants and medical plant material that contain coumarines and chromones.

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Medicinal plants and medical plant material that
contain coumarines and chromones.
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Overview
1. Coumarines definition. 2. Classification and
structure of coumarines 3. Determination of
coumarines 4. MP and MPM containing coumarines 5.
Chromone definition 6. Classification and
structure of chromones 7. Determination of
chromones 8. MP and MPM containing chromones
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Coumarins - are natural biological active
substances, at the base of which there lies
system of benzo-a-pyrone (the lactone of
O-hydroxycinnamic acid) and possessing
antispasmodic, anticoagulant, coronary
vasodilatory and other effects.
cis-orto-hydroxycinnamic acid (o-coumaric acid)
benzo-a-pyrone (coumarin)
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Classification and Structure of Coumarins

1. Simple coumarins and glycosides
2. Furanocoumarins
3. Pyranocoumarins
4. Benzocoumarins
5. Furanocoumarins
6. Isocoumarin
7. Complex coumarins

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Simple coumarins
Dihydrocoumarin
Coumarin
Aesculetin (6,7 dihydroxy coumarin)
Umbelliferone (7-hydroxy coumarin)
Scopoletin (6-methoxy-7-hydroxy-coumarin)
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Furanocoumarins ? consists of a 5-membered furan
ring attached to the coumarin nucleus,
Psoralen (furo-2,3 7, 6-coumarin)
Angelicin (isopsoralen) (furo-2,3 7,8
coumarin)
Bergapten
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Pyranocoumarins
2,2 dimethylxanthyletin (2,2
dimethylpyran-5,6 6,7-coumarin)
Seseline type
Visnadin
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Benzocoumarins ? contain a benzene ring
condensated to coumarin at 3,4arbon atoms.
Ellagic acid
3,4 - benzocoumarin
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Furanobenzocoumarins ? contain benzofuran
condensated to coumarin at 3,4-carbon atoms
Coumoestrol
Isocoumarin is a isomer of coumarin
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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.
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Qualitative tests on Coumarins

• Lacton test
• Coumarins are slowly hydrolysed by dilute alkali
  form yellow solution of o-coumaric acid salts.
  Coumarins regenerate after acidification or
  saturation by CO2.

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2. Azocoupling test The reaction with
diazotization sulfanilic acid in an alkaline
enviroment. Red colour develops.
3. Chromatographic methods
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Quantitative Determination of Coumarins

1. Spectrophotometric
2. HPLC
3. Gravimetric
4. Titration
5. Fluorometric
6. Polarographic

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Coumarin itself has been found in about 150
species belonging to over 30 diff'erent families.
Although it is probably present in the undamaged
plants as trans-O-glucosyloxycinnamic acid.
Enzyme activity in the damaged tissue leads to a
loss of glucose and a trans?cis isomerization
foliowed by ring closure. Coumarin gives a
characteristic odour of new-mown hay and occurs
in many Leguminosae (Fabaceae) such as melilot
and tonco beans. It is also recorded in woodruff.
Asperula odorata (Rubiaceae).
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Medical application of Coumarins Coumarins are
characterized with photosynthetizing (Fructus
Psoraleae, Fructus Ammi majoris, Folia Ficusi
carici), spasmolytic (Fructus Pastinacae),
P-vitaminic (Semina Hippocastani) action. As
individual substance coumarins possess
anticoagulant (dicoumarol), antimicrobic
(umbelliferone), estrogenic (coumestrols of
Trifolium spp, Fabaceae), antitumour (ostol)
action.
Some coumarin derivatives still find application
for their anticoagulant properties. Bishydroxycou
marin or dicumarol is a drug related to coumarin.
Dicumarol is an anticoagulant. It was obtained
originally from improperly cured leaves and
flowering tops of Melilotus officinalis (Linne)
Pall. (Fam. Fabaceae), but it is now prepared
synthetically. Sweet clover extract is used for
the symptomatic treatment of venous and lymphatic
vessel insufficiency.
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The antispasmodic activity of the barks of
Viburnum prunifolium Linne (blackhaw) and V.
opulus Linne (true cramp bark) (Fam.
Caprifoliaceae) has been attributed to scopoletin
(6-methoxy-7-hydroxycoumarin) and other
coumarins. Some furanocoumarins are
photosensitizers, therefore they are indicated
for the therapy of psoriasis and vitiligo.
Psoralens are photosensitizing furocoumarins that
occur in a number of plant families, including
the Apiaceae and Rutaceae, where they are a
common cause of phototoxicity. Methoxsalen,
8-methoxypsoralen, or xanthotoxin, a constituent
of the cremocarps of Ammi majus Linne (Fam.
Apiaceae), is used to facilitate repigmentation
in idiopathic vitiligo (leukoderma) and for
symptomatic control of severe, disabling
psoriasis. Visnadin, a pyranocoumarin isolated
from khella, has been extracted and marketed for
its coronary vasodilator effect
   
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Khellin is a furochromone found in the fruit of
Ammi visnaga Lam. (Fam. Apiaceae). The plant
grows in Mediterranean countries and has been
used for urethral spasm and renal colic. Khellin
is a potent coronary vasodilator and
bronchodilator in the treatment of coronary
insufficiency, angina pectoris, and bronchial
asthma.

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MP and MPM containing coumarins
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Melilot herb - Meliloti herba, EuPh Melilot
Melilotus officinalis Fabaceae Syn Kings
Clover, Yellow Sweet Clover, Hay Flowers, Wild
Laburnum According to the EP, the content
minimum 0,3 of coumarin. Constituents free
coumarins (0,4-0,9 ), furthermore
3,4-dihydrocoumarin, melilotol, melilotin
hydroxycoumarins, including among others
umbelliferone, scopoletin, herniarin, fraxidin
flavonoids kampferol- and quercetin glycosides
triterpene saponins, volatile oils. Useses. The
drug is used internally for problems arising from
chronic venous isufficiency, such as pain and
heaviness in legs, night cramps in legs, itching
and swelling for the supportive treatment of
trombophlebitis, postthrombotic syndromes,
haemoroids. The composition medicine cardiophit
(cardioprotective remedy)
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Parsnip fruit Pastinacae sativae
fructus Parsnip Pastinaca sativa Apiaceae
Constituents furocoumarins are in particular
angelicin, bergaptene, xanthotoxin, imperatorin,
psoralen volatile oilis chief components of cis-
and trans- ß-ocimene, trans-ß-farnesene
flavonoids, including rutin Uses. The fruits
are used in kidney and gastrointestinal
complaints and for digestion problems. Produced
photosensitizing medicines psoralenum, beroxan
(the mix of bergaptene and xantoxin). Smasmolitic
drug that effects on effect on coronary vessels
and prevents stenocardia - pastynacyn
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Greater ammi fruits Ammi majus
fructus Greater ammi Ammi majus Apiaceae Syn.
Bishopsweed, Bullwort, Ladys lace Constituents
furocoumarins are derivatives from psoralene
xanthotoxin, imperatorin, bergapten protein,
fixed oil Uses Medicines is used in
photochemotherapy to treat a number of skin
disorders, including mycosis fungoides, psoriasis
and vitiligo. Amifurine, Anmarinum gel
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Figs leaf Ficusi caricae folia Figs fruit
ficusi caricae fructus, BP Figs Ficus
carica Moraceae
Constituents leaves furanocoumarins, including
psoralen, bergaptene volotile oil flavonoids,
incl. rutin, Fructus fruit acids citric acid,
malic acid monosaccharides and oligosaccharides
(approximatly 50 ), to some extent transformed
into inverted sugar. Uses. Medicines from
leaves are used in photochemotherapy to treat a
number of skin disorders, including mycosis
fungoides, psoriasis and vitiligo Psoberan.
Fig fruit preparation are used as a laxative
Regulax, Cafiol
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Angelica radix Angelicae radices, EP,
BP Angelica Angelica archangelica
L. Apiaceae Syn. European angelica, Angels
wort Content minimum 2.0 ml/kg of essential
oil (dried drug). Constituents. Volatile oil
chief components are a- and ß-phellandrenes,
a-pinenes, macrociclic lactone furanocoumarins,
inc. bergaptene, xanthotoxin, scopoletin,
umbelliferone, archangelicin caffeic,
chlorogenic acids flavonoids tannins
archangelicin
Uses. Medicines are used as antispasmodic,
cholagogic and stimulatory for secretion of
gastric juice, at dyspeptic complants, loss of
appetite. ( Doppelherz Energietonikum)
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Wild carrot fruits - Dauci carotae fructus,
BH (1996) Wild carrot Daucus carota
L. Apiaceae Syn. Birds neat, Birds
nest Constituents. Coumarin umbelliferone,
esculetin, scopoletin furanocoumarin
8-methoxypsoralen a 5-methoxypsoralen flavones
(apigenin, chrysin, luteolin), flavonols (e.g.
kaemferol, quercetin) and verious glycosides,
carotinoids, valotile oil (very little) mono and
oligosaccharides glucose, saccharose. Uses.
Wild carrot is stated to possess diuretic,
spasmolitic and carminative properties. Traditiona
lly, it has been used for urinary calculus,
lithuria, cystits, gout, and specifically for
urinary gravel or calculus. Urolesanum
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Chromone
Chromone are natural biological active
substances the general formula is C6-C3, at the
base of 9,10-benzo-?-pyrone.
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Classification

1. Simple cromones
2. Benzochromones
3. Furanochromones and their glycosides
4. Pyranochromones
5. Hydroxypyranochromones

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1. Simple chromones
3-Methylchromone 5,7-Dihydrochromone Aloesin
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2. Benzochromone
6,7-benzochromones 7,8-benzochromones
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3. Furanochromones
Khellin Visnagin
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4. Pyranochromones
Gammaudol Pterochromanol
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5. Hydroxypyranochromones
Pteroglycol Pteroxilin
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Qualitative tests on Chromones

1. Specific odour.
2. Form with alkali solution o-hydroxy-ß-diketones
   without regeneration of ?-pyrone ring (unlike
   coumarine).
3. Fluorescence in UV-light (blue, yellow, greenish
   yellow, brown)
4. Dont give Azocoupling test, 2 solution of
   aluminium chloride, with magnesium and
   concentrated hydrochloric acid (unlike
   flavonoids).
5. Form coloured compounds with concentrated acid
   (citric colour), and concentrated alkali (purpe
   colour).

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Pharmacological action

1. Spasmolytic.
2. Antibacterial.
3. Anticoagulant.
4. Analgetic.
5. Antiallergic.

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MP and MPM containing Chromones
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Bishops Weed fruit Visnagae daucoides fructus
(Ammi visnagae fructus) Bishops Weed Visnaga
daucoides Gaerth., Ammi visnaga
(L.) Apiaceae Syn. Khella, Toothpickweed. Consti
tuents. Furochromones are particularly khellin,
visnagin, khellol and khellol glicoside
pyranocoumarins visnadin and samidin
furanochromones flavonoids quercetin and
isohamnetin and their 3-sulfates volotile oil
fatty acids. Uses. The drug intensifies coronary
and myocardial circulation acting as a mild
positive ionotrope. It has antispasmodic effect
on smooth muscles Avisan, Celin.
Marelin, Phitolit
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Dill fruit Anethi graveolentis fructus Dill
Anethum graveolens Apiaceae Syn.
Dilly Constituents. Furanochromones are
visnagin, khellin furanocoumarins, inc.
bergaptene hydroxycoumarins umbelliferone
volotile oil (2,5-4,0 ) chief constituents are
carvone (approx. 50 ), dill apiole, ()
limonene fatty oil phtalides. Uses. The fruit
of the Dill plant an antispasmodic effect on the
smooth muscles of the gastrointestinal tract, and
a bacteriostatic effect. Anetin
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Thanx for the attention