Substances affecting motoric activity of GIT
(Prokinetics)
1. Carminatives
2. Laxatives
3. Antidiarrhoics
4. Spasmolytics
CARMINATIVES
DEFLATULENTS
 Preparations removing problems
after ingestion of easily fermented
food.
 Affecting gut peristaltic and
intestinal microflora
 Useable also cholagogic and
antispasmodic effect of some
essential oils
Matricariae flos – Camomila flowers ČL 2005
Matricaria (Chamomilla) recutita - German chamomile, wild
camomile (Asteraceae)
 Annual herb widely spread and cultivated
 Drug: dried flower heads, hollow receptacle
- characteristic pleasant aromatic odour
- contains et least 4 ml of essential oil / 1 kg
of drug
 Content compounds:
- essential oil - azulenes (blue pigmentation)
- bisaboloids
- ethers
- flavonoids
 Usage:
- carminative, spasmolytic
- antiphlogistic
- antiagregant
Matricariae flos – content compounds
O
O
O
O
OH
O
OH
- H2O
- CH3COOH
- CO2
Matricine
Chamazulencarboxylic acid
Chamazulene
1,4-dimethyl-7-ethylazulene
1
4
7
(4-20 %, antiphlogistic)
Matricariae flos – content compounds
O
O
H
cis-enoletherpolyine
en-in-dicycloether
(spasmolytic, antiphlogistic)
OH
OH
O
Lbisabolol Lbisabololoxid A Lbisabololoxid B
(10-25 %, antiphlogistic) (10-25 %, spasmolytic)
Matricariae flos – content compounds
O
OH
OH
OH
OH
O
MeO
OGlc O
OH
OH
O
MeO
MeO
OMe
OMe
Patulitrin Lipophilic chammomila flavone
(antiagregation effect)
Matricariae flos – content compounds
O
O
CH2
CH3 CH3
CH3
O
methylene--butyrolacton
Anthecotulid
alergic
Chamomillae romanae flos – Roman chamomile flower
ČL 2005
Chamaemelum nobile - Roman chamomile (Asteraceae)
 Perennial plant, for pharmaceutical
purposes cultivated
 Drug: flowerheads of fullflower
variety (A. nobilis var. flore pleno)
 Full receptacle
 Content compounds:
- essential oil (esters of angelic and
isobutyric acids with isoamylalcohol,
chamazulene)
- flavone glycosides, coumarins
 Usage:
- see Matricariae flos (without
spasmolytic activity)
Chamomillae romanae flos – content compounds
Chamazulene
1,4-dimethyl-7-ethylazulene
1
4
7
O
OH
OH
OH
OH
O
MeO
OGlc
Patulitrin
H
CH3
COO-CH2-CH2-CH(CH3)CH3
CH3
CH3
H
COO-CH2-CH2-CH(CH3)CH3
CH3
Tigline-2-methylbutanoate
Anglic-2-methylbutanoate
Z
E
CH3
CH3 O
O
CH2
OH
O CO
CH3
H
CH3
Nobiline (bitter substance)
Menthae piperitae folium – Peppermint leaves ČL 2005
Mentha piperita, peppermint (Lamiaceae)
 Perennial herb cultivated in mild
climate. No wild spreading. It is a
hybrid.
 Harvest in flowering period, drug
should not contain young leaves (they
decrease quality)
 Drug: up to 30 0C dried leaves, at
least 9-12 ml of essential oil /1 kg of
drug. Characteristic odor and taste
Content compounds: essential oil
(menthol and its esters, menthone,
pinene, piperitone, phellandrene,
jasmone, menthofurane), rosmarinic
acid, tannins, bitter substances
Usage: carminative, cholagogue
Menthae piperitae etheroleum – Peppermint essential oil
ČL 2005
Mentha piperita - peppermint (Lamiaceae)
 Essential oil obtained from fresh flowering plant by water steam
distillation
 Yellowish liquid of characteristic odor and cooling taste
 Content compounds:
- menthol (over 50 %) and its esters with acetic and valeric acid
- ketones menthone and piperitone
- carbohydrates pinene, phellandrene, limonene
- compounds with oxygen in structure (jasmone, menthofurane,
acetaldehyde, isovarelaldehyde
 Usage:
- carminative, spasmolytic, cholagogue
- corigent of taste and odor
- cosmetics, food industry
Menthae piperitae etheroleum – content compounds
O-PP O
O O
O OH
O
OCOCH3
Geranyldiphosphate Piperitone
Piperitenone Pulegone
Menthone Menthol
Menthofurane Menthylacetate
Menthae piperitae etheroleum – content compounds
O
Jasmone
CH3
OH
H
H
H
CH3
CH3
1
2
5 a enantiomer
Mixture of the same portion of (1RS,2SR,5RS)-2-isopropyl-5-methylcyclohexanols
Menthae crispae herba – spearmint haulm
Mentha spicata Huds. var. crispa, spearmint
 Toothpastes
 Gewing gum „Spearmint“
O OCOCH3
CH2
OCOCH3
Carvon Dihydrocarveol-
acetate
Dihydrocuminalcohol
acetate
Carvi fructus – Caraway fruit ČL 2005
Carum carvi - caraway (Apiaceae)
 Biennial or perennial herb, cultivated in
Europe, Asia, USA
 Drug: whole dried matured diachene.
Contains at least 30 ml of essential oil / 1
kg of drug
Content compounds:
- essential oil (D-carvone – 50 to 80 %,
D-limonene,
dihydrocarvone, carveol)
- fatty oil up to 20 %, coumarins, tannins
Usage:
- carminative (spasmolytic), lactagogue
- antibacterial effect
- spice, liquors manufacturing
Carvi fructus – content compounds
O-PP
- H+ ox.
OH
OH
O
O
ox.
Geranyldiphosphate
+
Limonene Carveol
Dihydrocarveol
Carvone
Dihydrocarvone
15-30 % 50-80 %
Coriandri fructus – Coriander fruit ČL 2005
Coriandrum sativum - coriander, cilantro (Apiaceae)
 Annual herb, cultivated in Europe, India and north
Africa. Main producers: Russia, Holland
 Drug: dried, rounded diachenes; contains at least
3 ml of essential oil / 1 kg
Content compounds:
- essential oil (linalool - 60 to 70 %, pinenes,
geraniol, terpenoid carbohydrates with prevalence
of terpinenes
- fatty oil
Usage:
- carminative, spice, liquors manufacturing
- heavy metals detoxication
- antibacterial, antioxidant
- metabolism of cholesterol
H
CH2
OH
OH
CH2OH
OH
COH
Linalool Geraniol
60-70 %
Citronelol Borneol
Tridecene-(2)-al-(1)
Coriandri fructus – content compounds
 Bright yellow powder obtained from cut garlic cloves by lyophilization or
drying bellow 65 0C and grinding
 Contains at least 0,45 % of allicine
Content compounds:
- Stinking essential oil, formed from alliine, after grinding of garlic and
water steam distillation, alliine is further decomposed
- Vitamins A, B1, B2, C, amid of nicotinic acid, choline, iodine
Usage:
- Carminative with disinfection, spasmolytic and choleretic effect
- Antibacterial effect against G+ and G- pathogens of GIT,
antimycotikum (allicin), anthelmintic
- Ajoene – antithrombotic factor (inhibition of fibrinogen receptors at
blood platelets
- Folk medicine: hypertension, arteriosclerosis
Allii sativi bulbus pulveratum – Powdered garlic bulbs
ČL 2005
Allium sativum - garlic (Liliaceae)
CH2
CH
CH2
S O
CH2
CH NH2
COOH
CH2
CH
CH2
S OH
- H2
O
CH2
CH
CH2
SO
CH2
CH
CH2
S
CH2
CH
CH2
S
CH2
CH
CH2
S
CH2
C-NH2
COOH
CH3
C=O
COOH
NH3
CH3
CH2
CSH
2
Alliine
alliinase
2
Allylsulfonic
acid
Allicine Diallyldisulfide
Aminoacrylic
acid
2
Pyruvate
+ 2
+ H2O
Propionylthioaldehyde
Allii sativi bulbus pulveratum – content compounds
LAXATIVES
(purgatives, diarrhoics, cathartics)
Administered during:
- acute functional ostipation
- Chronic obstipation refractive
to changes of life style
In special indications:
- Emptying before X-ray
diagnostics
- Before surgery
- After some anthelmintics
During some intoxications
Division according to the
mechanism of effect:
- Swelling up, increasing the gut
content volume
(polysaccharides)
- Salinic, diluting the gut
content (Sal purgans)
- Lubricants and emulsifiers
(Paraffinum liquidum)
- Directly irritating intestinal
wall, stimulating peristaltics
(derived from
anthraquinone, Resina
podophylli, some plant oils)
Agar - Agar ČL 2005
Species Gelidium, Gracilaria, Euchema, Petrocladia
(Rhodophyceae)
 Algeae from the class of Rhodophyceae (Japan, USA, New Zealand, South
Africa)
 Harvested algeae are bleached and the mucilage is gathered by soaking in hot
water.
 Solydified gel is dried by lyphilisation, salts are removed, and it is formed and
further dried.
 Drug: bright yellow, translucent, fragile compressed strips or powder
Contain compounds: mixture of polysaccharides
- agarose (70 %) and agaropectin (30 %)
- residues of mineral compounds and iodine
Usage:
- mild laxant (pediatrics)
- component of hydrophilic ointment bases, tablets disintegrator, emulsion
stabilizer
- food industry, industry, microbiology
Agar – content compounds
O
H
OH
O
CH2OH
H
OH
OH
OH O
OH
CH2
O
O
H
OH
O
CH2-O-SO3H
H
OH
OH
OH O
OH
CH2
O
1
3
6
D-galaktosa
3,6-anhydro-
-L-galaktosa
A G A R O S A
1
3
6
D-galaktosa
3,6-anhydro-
-L-galaktosa
A G A R O P E K T I N
Tragacantha – Tragant ČL 2005
Astragalus gummifer, goat´s horn (Fabaceae)
 Thorny shrubs from western Asia
 Cellular mucilage, it is produced in cells of cortex
medulla and medullar rays, it is flowing out
spontaneously after wounding
 Drug: bright flat pieces of corneous consistence or
white powder
Content compounds: mixture of polysaccharides and starch
- basorine (60 %) swelling in water, not soluble
- tragacanthine (40 %), water soluble
Usage:
- mild swelling laxant
- base of hydrophilic ointment bases, technology of
tablets
- cementing agent in stomatology
- food nutrition
- prevents formation of emulsions
Tragacantha – content compounds
 Tragacanthine is composed of tragacanthic acid and arabino-galactose
Tragacanthic acid:
- linear chain of D-galacturonic acid esters
- side chains: xylose, fucose, galactose
 Basorine is composed of: glucuronic acid, galacturonic acid, arabinose,
xylose, galactose
Lini semen – flax seed ČL 2005
Linum usitatissimum, flax (Linaceae)
 Annual herb, cultivated in for example
Argentina, India, Marocco, USA, Czech
republic
 Drug: dried flat, dark red-brown smooth
shiny seed. Inside endosperm with two big
oily cotyledons
Content compounds:
- mucilage (6 %) in epidermal cells of testa
- oil (až 40 %)
- proteins (20 %), cyanogenic glycoside
linamarine
Usage:
- laxative (together with mucilage also oil)
- externally emolient, antiphlogistic
Lini semen – content compounds
 Mucilage (mixture of neutral and two acidic fractions). Hydrolysis
produces:
- galacturonic and mannuronic acids (cca 30 %)
- galactose (8-12 %)
- arabinose, rhamnose and xylose
 Oil (triglycerides of linolic, linolenic and oleic acid)
 Cyanogennic glycoside linamarin
CH3
O-Glc
CH3 CN
Psyllii semen – psyllium seed ČL 2005
Psyllium afra (Plantago psyllium), Plantago ovata
(Plantaginaceae)
 Annual herb cultivated in France and Mediterranean. Fruit is capsulle (boll)
 Drug: Brown, smooth, shiny, eliptic seeds, 2-3 mm long
Content compounds:
- mucilage localized in epidermal part (10-12 %)
- proteins, fatty oil, phytosterols
- iridoid glycoside aucubine
Usage:
- mild laxative (tea spoon = 6,3 g of drug is lasting to swell in water, it is
consumed with larger portion of liquids). Effect after 12 - 24 hours
-apretation agent in paper industry
Aloe barbadensis ČL 2005, Aloe capensis ČL 2005 - Aloe
Aloe ferox - cape aloe; Aloe vera - Chinese Aloe, Indian
Aloe, True Aloe, Barbados Aloe, Burn Aloe; Aloe
arborescens (Liliaceae)
 Succulent plants of tropic and subtropic Africa,
cultivated for example in South Africa
 Drug: Concentrated and solidified juice obtained
from leaves
- Aloe lucida (concentrated by boiling)
- Aloe hepatica (evaporated slowly)
Contain compounds:
- aloine = C-glucoside of aloeemodinanthrone
- aloinosides = O-glycosides of aloine
- resins and mucilage
Usage:
- laxative,
- in small dosage stomachic, choleretic
- contraindication: pregnancy, breast-feed,
menstruation, hemeroids
Aloe – content compounds
O
OH OH
CH2
-OR
CH2
OH
O
O
OH
CH3
CH2
OH
OOMe
OH
1
36
8 1
36
8
Aloin (barbaloin, kapaloin) R = H
Aloinosid B R = L--rhamnosa
Homonataloin
1,7-dihydroxy-3-methyl-8-methoxy-
anthron-10-C-D-glukosid
10
Sennae folium – Senna leaves ČL 2005
Cassia angustifolia, C. acutifolia – senna (Fabaceae)
 Cca 1 m tall shrub, frutits are pods
 C. angustifolia – 5-8 paired leaves, cultivated in
India (Tinevelly)
 C. acutifolia – 4-5 paired leaves, cultivated in Nile
area (Alexandrinae)
 Drug: dried leaves, grey-, yellow-, brown-green
fragile leaves
Content compounds (at least 2,5 % of
hydroxyanthracene derivatives, expressed as
sennoside B)
- sennosides A and B (dirrheindianthron-8,8’-di-glc)
and their fission products
- flavonoids, mucilage, essential oil
- resins (sennanigrins)
Usage:
- laxative during acute and chronic constipations
- after removal of resins – Folia sennae praeparata)
Sennae folium – content compounds
O OH
H
C OOH
OGlc O OH
H
C OOH
OH
OH OHO
C OOH
O OH
CO OH
OH
O OH
C OOH
OH
O OH
H
C OOH
OGlc O OH
H
COOH
OH
O OH
H
C OOH
OGlc
O OH
H
CH2 OH
OGlc
O
O
O OHGlc
COOH
O
O
O OH
CH2 OH
Glc
H +
Sennosid A
Sennosid B
Sennidin A
Sennidin B
oxid.
2 m ol. Rheinanthron
Dirhein
Sennosid C
Sennosid D
red.
Rhein-8--D-glukosid
Aloeemodin-8--D-glukosid
8 '
8 '
1
1
1 '
1 '
3
3
3 '
3 '
8
8
Sennae acutifoliae, angustifoliae fructus – senna
fruit ČL 2005
Cassia acutifolia – senna (Caesalpiniaceae)
 Flat kidney-shaped pods, green-brown with stains at
place of seeds, 40-50 mm long, 20 mm wide
 Pods contain 5-8 seeds
Contain compounds (localized in pericarp):
- hydroxyanthracene glycosides (as sennoside)
- S. acutifoliae fructus 3,4 %
- S. angustifoliae fructus 2,2 %
- primary glycosides from rheindianthroneaglycon and
upto 10 molecules of sugar
- mucilage and tannins
Usage:
- mild laxative, effect milder than effect of Sennae
folium
- extract is recommended to prepare via cold
Frangulae cortex – Alder Buckthorn bark ČL
2005
Rhamnus frangula - Alder Buckthorn (Rhamnaceae)
 Shrub widely distributed in Europe, close to
watercourses, margins of humid woods
 Drug: dried bark or its pieces from trunk and
branches. Rolled fragments 0,5-2 mm thick. On the
outer layer prolongated lenticells.
 Before use one yaer of storage or one hour of heating
at 100 0C, otherwise risk of colics and vomiting
Content compounds:
- at least 7 % of glucofrangulins A and B (isomers)
A = emodin-6--L-rhamnoside-8--D-glucoside
- tannins, bitter substances, saponins
Usage: laxative
- contraindication: pregnancy, breast-feeding, ileus;
during chronic use risk of hypokalemia –
enformcement of cardioglycoside effect
Frangulae cortex – content compounds
O H
C H 3
H H
C H 3
O HO
O
O
O O
O
O O H
C H3O
O
O H O H
C H3O
O
R ha
O H O H
C H 3
O
O
r ha
O
O O H
C H 3O
O
O
r ha
O H O H
C H 3OH
O
O
D ia n th ro n g lu ko f ra n gu lin u A a B
G lu ko fra n g u lin a n th ro n A a B
F ra n g u lin a n th ro n A a B
F ra ng u lin A a B
G lu ko fr an g u lin A (6 - L - rh a)
G lu ko fr an g u lin B (6 - L  rh a )
r h am n o d ia sta s a
F ra n g u lae m o d in
+ R h a
+ glc
  D -g lc
  L -rh a
  D -g lc
 D -glc
 D -g lc
  L -rh a
  L -rh a
Rhamni purshianae cortex – Cascara bark ČL
2005
Rhamnus purshianus - Cascara buckthorn
(Rhamnaceae)
 Tree native and cultivated in North America
Drug: dried bark and its fragments from young trunk and
thin branches. Mild rolled or flat fragments 1-5 mm
thick. On the outer side transversally prolongated
lenticells, sometimes grey becouse of lichens.
 Before consumption to store one year or heat 1 h at
100 0C, otherwise risk of vomiting and colics
Content compounds:
- at least 8 % of anthraglycosides, from that at least
60 % of cascarosides
- tannins, bitter substances, derivatives of
benzoylphloroglucinol
Usage: in America and western Europe the mostly used
laxative
- contraindication: pregnancy, breast-feeding, ileus;
during chronic use risk of hypokalemia –
enformcement of cardioglycoside effect
- melanosis coli
Rhamni purshianae cortex – content compounds
O OH
CH2OH
O
H
O OH
CH3
H
O
O
O
OH OH
CH3OH
O
OH OH
H O
CH3OH
glc
-D-glc
-D-glc
10
10
Cascarosid A, B
-D-glc
Cascarosid C, D
8-O-glukosidy aloinu 8-O-glykosidy chrysaloinu
C10-isomery
Frangulaemodin Frangulaemodin-
oxanthron-9-glukosid
Rhei radix – rhubarb root ČL 2005
Rheum palmatum, R. officinale - rhubarb (Polygonaceae)
 Huge perennial herb native in mountains (3000 – 4000 m)
of west China and east Tibet, today widely cultivated.
Rhizomes of 4-6 yaers old plants are peeled, cut and dried
 Drug: dried whole or cut roots and rhizomes without outer
layer of bark. Contains at least 2,2 % of
hydroxyanthracene derivatives expressed as rhein
Content compounds:
- rheoanthraglycosides (in oxidated and reduced form,
free or as glycosides. Dianthrones rheidin and
senidin, free anthraquinones)
- rheotanoglycosides (initiator of astringent effect:
glucogallin, catechine, epicatechingallate)
- starch, pectin, traces of essential oil, oxalate
Usage:
- laxative in dose of 1,0-3,0 g pro dosi
in dose 0,05-0,2 g pro dosi obstipant
- cholagogue, stomachic
Rhei radix – content compounds
O OH
H
OH
CH2
OH
O OH
H
COOH
OH
O OH
H
CH3
OH
OH
O O H
H
COOH
OH
O
O
OH OH
CH2
OH
O
O
OH OH
CH3
O
O
O H O H
COOH
O
O
OH OH
OH CH3
O
O
OH O H
CH3
M eO
Sennidin CRheidin A
red. oxid.
Chrysofanol Aloeemodin Rhein
Frangulaemodin Fyscion
Radix rhei rapontici
Rheum rhaponticum (Polygonaceae)
 Perennial herb giving roots sometimes used to replace Rheum
palmatum
 Can to be used, contains rhaponticin (estrogenic effect – controls
development and functions of genital tract, secondary sexual signs and
psychosexual functions of women. At man produces feminism and
impotence)
OH
MeO
OR
OH
Rhaponticin R = -D-glc
Rhapontigenin R = H
Podophyllinum, Resina podophylli - Podophyllin
Podophyllum peltatum - mayapple (Berberidaceae)
 Perennial plant native to humid woods of eastern part of North
America. Today widely cultivated. Up to 1 m long creeping rhizome.
 Drug: via ethanol extraction obtained resinous extract from rhizome
harvested after dying of aerial part. Extract could be after evaporated
and powdered to bright brown powder.
Content compounds:
- Lignans (20 % of podophyllotoxin, 13 % -peltatin, 7 % -peltatin,
4’-desmethylpodophyllotoxin)
- Quercetin (5 %), starch
Usage:
- laxative
- source of lignans with trans arranged lactone ring - cytostatics
Podophyllinum – contain compounds
O
O
O
O
MeO OMe
R2R3
O R1
Podophyllotoxin CH3 OH H
-Peltatin H H OH
-Peltatin H OH OH
R1 R2 R3
Jalapae resina – Jalapa resin
Exogonium purga (Convolvulaceae)
 Perennial plant native in Mexico, cultivated in Mexico, India
Jamaica
 Drug: resine obtained via ethanol extraction, evaporation,
powdering.
Content compounds:
- Glucoresins, obtained from glycosides, thier sugar part is
oligosaccharide, aglycon hydroxyderivatives of fatty acids
(for example jalapinolic, exogonic acids...). Carboxyl groups
form esters with OH groups of sugars forming macrocycles.
- Phytosterols, coumarins
Usage:
Laxativum drasticum. Not used in Europe.
Jalapae resina – content compounds
O
O
CH3 CH2
COOH
Exogonová kyselina
ANTIDIARHOICS
 Drugs with tannins content, which show astringent effect (formate
unsoluble substances with proteins, lower intestinal secretion)
 Tannins – heterogenous group of natural compounds. They are
amorphous, high-molecular substances; formate colloid water
solutions with astringent taste.
1. Hydrolyzable tannins
- gallotanins
- ellagitanins
2. Condenzed tannins
- building blocks are catechines and flavonoids, often esterified by
gallic acid derivatives (depsides)
Drugs used as antidiarrhoics
 Tanninum – Tannin ČL 2005
Quercus infectoria - gall oak (Fagaceae)
Mixture of esters of glucose with gallic and 3-galloyl-gallic acids
 Ratanhiae radix – rhatany root ČL 2005
Krameria triandra – rhatany (Krameriaceae)
Catechine tannins
 Tormentillae rhizoma – potentilla rhizome ČL2005
Potentilla erecta (P. tormentilla), potentilla (Rosaceae)
Catechine tannins
Tormentillae tinctura (ČL 2005)
Drogy používané jako antidiarhoika
 Agrimoniae herba – agrimony herb ČL 2005
Agrimonia eupatoria, agrimony (Rosaceae)
Catechine tannins mixture
 Hamamelidis folium – witch hazel leaves ČL 2005
Hamamelis virginiana, witch hazel (Hamamelidaceae)
Hydrolyzable tannins of elagotanine type (hamamelitannin)
 Quercus cortex – oak bark ČL 2005
Quercus robur; Q. petraea - oak (Fagaceae)
Catechine tannins, used mostly as external preparations
SPASMOLYTICS OF GIT
 Atropini sulfas monohydricus – Atropin sulphate ČL 2005
 Scopolaminii hydrobromidum trihydricum – Scopolamin
hydrobromide trihydrate ČL 2005
 Papaverini hydrochloridum – Papaverine hydrochlorid ČL 2005
 Khelline
SUBSTANCES AFFECTING VOMITING
 Emetics
- Emetini dihydrochloridum pentahydricum – Emetine dihydrochloride
pentahydrate ČL 2005
- Apomorphini hydrochloridum hemihydricum – Apomorphine
hydrochloride hemihydrate
 Antiemetics
- Scopolamini hydrobromidum trihydricum – Scopolamine
hydrobromide trihydrate (ČL 2005)
- Zingiberis rhizoma – Ginger rhizome ČL 2005