kuliah farmakognosi alkaloids 2
TRANSCRIPT
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Chemical properties The substitution on the nitrogen atom
The state of the alkaloid
R
NH2
R
HN
R2 R
N
R3
R2
R
N
R4
R2
R3+
Cl-1ry 2ry 3ryquaternary
R
NH2
R
N
R3
R2
R
NH3
Cl-
+O
Free base
Salt formN-oxide
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Classification Non-heterocyclic or atypical alkaloids or biological
amines
Heterocyclic or typical alkaloids: divided into groups according to their ring structure
H3CO
H3CO
OCH3
CH2 CH2
NH2
Mescaline
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N
H
N
H
N
N
pyrrole pyrrolidine pyrrolizidine pyridine
HN
NMe
N
N
piperidine tropane quinoline isoquinoline
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NH N
H
N
NH
NMeindoleindolizidine imidazole
aporphine
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N
N
H3CO
HO
H H
N
N
H3CO
HO
H H
89
Quinine Quinidine
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NMe
OH CH2OH
(-) hyoscyamine
N
OH CH2OH
(-) hyoscine (scopolamine)
Me
O
NMe
OH
tropine O
O
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EFEK FARMAKOLOGI ALKALOID
1. Analgetik dan narkotik : morfin 2. Alkaloid jantung : alkaloid kinidin dan
spartein (Erytropleum guineense) 3. alkaloid yg mempengaruhi peredaran
darah dan pernafasan : Veratrum, Rauwolfia (hipotensi), lobelia (lobelin murni obat asma)
4. kemoterapetik dan antiparasit (kina, areca dan granatum (anticacing),
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5. stimulan uterus : secale alkaloid (Hydrastis), alkaloid benzilisokinolin (berberis)
6. anastetik lokal (cocain) 7. midriatika : belladona dan alkaloid coca.
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AlkaloidTropan Ester alkaloid : asam organik + amino alcohol (Basa). The parent base is the “Tropane” base.
Alkaloid Tropane dikelompokan mjd:
1- Solanaceous Tropane Alkaloids.
2- Erythroxylon (Coca) Alkaloids.
HN
12
34
56
7NH
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1- Solanaceous Tropane Alkaloids
Terdapat:Atropa, Datura, Hyoscyamus, Duboisia spp.
Alkaloid utama:1- Atropine.
2- Hyoscyamine.
3. Hyoscine (Scopolamine).
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Atropine & Hypscyamine Hyoscyamine is the major natural alkaloid with
negative optical rotation (l- form). During extraction hyoscyamine racemizes to the
optically inactive dl Atropine. Both alkaloids composed of tropine base and tropic
acid.
NCH3 O
OHO
N
O
Me
O
H CH2OHN
O
O
CH2OHMe
Atropine(-)-Hyoscyamine
Tropine base
Tropic Acid
*
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Hyoscine (Scopolamine) Hyoscine is an ester of l-tropic acid with scopoline
base. Hyoscine is a syrupy liquid.
NCH3 O
OHO
O
Scopoline base
Tropic Acid
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Khasiat dan aksi farmakologi:The three Alkaloids are anticholinergic agents: Decrease saliva and GIT secretions so used preoperative. Decrease motility of smooth muscles so used as
antispasmodics. Stimulate respiratory system. A mydriatic (causes dilatation of the eye pupil).
An antidote to organophosphorus insecticides. Hyoscine has more central effect so it is sedative and hypnotic. Hyoscine is mainly used as antiemetic.
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2- Erythroxylon (Coca) Alkaloids
Occurrence:Coca leaves contain about 2% total alkaloids.
Main Alkaloids are:1- Cocaine.
2- Cinnamylcocaine.
3. a- truxilline.
The base for Coca Alakloid is called “Ecogonine”
NH3C OH
C
O
OH
Ecogonine
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It is the major Alkaloid in Coca leaves. Cocaine is diester Alkaloid. Heating at 160 0C in conc. HCl leads to hydrolyses of
cacaine to MeOH, Benzoic acid and Ecogonine base.
NCH3 O
O
COOMe
Benzoic acid
Ecgonine base
Cocaine
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Production of Cocaine commercially: The total Alkaloids are hydrolysed to obtain the free base. The base is then Methylated with HCl in MeOH. The Methylated base is then esterified with Benzoly
chloride.
Cinnamylcocaine
NCH3 O
O
COOMe
Cinnamic acid
Ecgonine base
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Uses:Cocaine was used as local anesthetic.
Cocaine has a CNS stimulant activity so is one of the widely abused drugs.
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Catharanthus :Vinca
Catharanthus roseus
Family : Apocynaceae
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Perennial or annual herbaceous plant 40-60cm .
The leaves have acute base , rounded apex and have entire margin .
The flowers are rose or violet or white or white with red eyes .
The fruits have slight odour with bitter taste .
The leaves have very strong and unpleasant odour and taste.
origin : Australia, Madagascar also cultivated in Tropical Africa .
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Biochemical constituents
Alkaloid indole group :1. Vincristine 2. Vinblastine3. Vindoline (inert)4. Catharanthine (inert)500kg of Catharanthus plant used to
isolate 1g vincristine Main slide
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Therapeutic uses Anti-neoplastic activity
(anti tumer)Used for treatment of
leukemia in children.
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Medications
1. Vincristine ®-Vials- Abic 2. Oncovin® - Vincristine – Vials-Lily 3. Velbe ® -Vinblastine – Vials-Lily
(Hodgkin´s disease )4. Blastovine® -Vinblastine-Teva –
Vials.All of these drugs present as
sulphate salts.
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