Alkaloids (Updated) (1).pdf

Alkaloids

1. Alkaloids
BPH-122

2. Alkaloids
Alkaloidsarebasicnitrogenouscompoundswhichoccurabundantlyin
theplantkingdom.Theycontainoneormorenitrogenatoms,usuallyina
heterocyclicringandhaveamarkedphysiologicalactiononmanand
animals.
Thenitrogenatommayexistasaprimaryamine(RNH
2),asasecondary
amine(R
2NH)orasatertiaryamine(R
3NH).Thesecompoundsarebasic
butthedegreeofbasicitydependsonthestructureofthemoleculeand
thepresenceandlocationofotherfunctionalgroups.
Inadditiontocarbon,hydrogenandnitrogen,alkaloidsmayalso
containoxygen,sulfurandmorerarelyotherelementssuch
aschlorine,bromine,andphosphorus.
2

3. N-CH
3
OCOCH
CH
2
OH N
CH
3
N Nicotine
Atropine
3
Examples

4. Functionsofalkaloidsinplants
Thepossiblefunctionsofalkaloidsinplantsare
1.Theyarepoisonousagentsthatprotect
theplantsagainstinsectandherbivores.
2.Alkaloidsarereservesubstancescapable
ofsupplyingnitrogenorothernecessaryelementstothe
plants.
3.Theyareregulatorygrowthfactors.
4.Alkaloidsaretheendproductofdetoxificationreaction
representingametaboliclockingupofcompounds
otherwiseharmfultotheplant.
4

5. Properties of alkaloids
•Mostalkaloidsarewelldefinedcrystallinesubstancesand
unitewithacidstoformsalts.Intheplantstheymayexistsin
thefreestateorassalts.
•Thealkaloidsareusuallyinsolubleorsparinglysolubleinwater
buttheirsaltswithacidsarefreelysoluble.
•Thefreealkaloidsaresolubleinether,chloroformorother
non-polarsolventsinwhichthealkaloidalsaltsareinsoluble.
•This property permits a ready means for the isolation and
purification of alkaloids.
•The alkaloids usually possess a bitter taste
5

6. General properties
•Theyarecomplexchemicalcompoundsofplantorigin.
•InadditiontoCarbonandHydrogentheyallcontainNitrogenandgenerallyalso
Oxygen.
•TheNitrogenatomusuallyexistsinaheterocyclicring.
•Mostofthealkaloidsarecrystallinesolids,thoughafewareamorphous
(Exceptions:Coniine,NicotineandSparteineareliquid)
•Alkaloidsareusuallycolorlesscompounds(Exceptions:Betaineisred,Berberine
isyellow)
•Alkaloidsareeitherinsolubleorsparinglysolubleinwater,buttheirsaltswith
acidsarefreelysolubleinwater.Theyaresolubleinorganicsolvents.
•MostofthemareprecipitatedbyDragendorff’s,Mayer’s,Wagner’sand
Hager’sreagent.
•Inplants,alkaloidsusuallyexistintheformofsaltsofsimpleorganicacids,
suchasLactic,Malic,TartaricorCitricacids(Exceptions:Somealkaloidsexistas
glycosidee.g.Solanine,Tomatineetc.)
•Thealkaloidsusuallypossessabittertaste.
•Aminoacidsareusedastheprecursorforthebiosynthesisofalkaloids.
•Theyareusuallybasicinnature.

7. Pharmacological action
The alkaloids have a wide range of pharmacological action. For
example:
Analgesic and narcotic Morphine, Codeine
CNS stimulant Strychnine
Mydriatic Atropine
Myotic Pilocarpine
Hypertensive Ephedrine
Antihypertensive Reserpine
Antineoplastic / Anticancer Vinblastine, Vincristine
Emetic Emetine, Sanguinarine
Oxytocic Ergonovine
Skeletal muscle relaxant (+)-Tubocurarine
Cardiac arrhythmia Quinidine
7

8. Naming of alkaloids
•BasedontheGenus:Atropine(Atropa),lobeline(Lobelia),
ephedrine(Ephedra)
•BasedonSpecies:Cocaine(Erythroxyllumcoca),belladonnine
(Atropabelladonna)
•BasedoncommonSources:Ergotamine(Ergot)
•BasedonPharmacologicalactions:Emetine(emetic)
•BasedontheDiscoverer:Pelletierine(Pelletier)

9. Tests for alkaloids
Mostalkaloidsareprecipitatedfromneutralorslightlyacid
solutionbyvariousreagents.Theprecipitatemaybe
amorphousorcrystallineandareofvariouscolors.Suchas
Reagent Colorofppt.
Mayer’sreagent Cream
(Potassiummercuriciodidesolution)
Wagner’sreagent Reddishbrown
(SolutionofI
2inKI)
Dragendorff’sreagent Reddish brown
(Solutionofpotassiumbismuthiodide)
Hager’sreagent Yellow
(Saturatedsolutionofpicricacid)
9

10. Chemical Tests For Alkaloids
•Thequalitativechemicaltestsusedfordetectionofalkaloids
aredependonthecharacterofalkaloidstogiveprecipitate
assaltsoforganicacidsorwithcompoundofheavymetals
likeHg,Au,Pt,etc.
•TestbyDragendorffreagent(Potassium-bismuth-iodide
solution):-Alkaloidsgivereddish-brownprecipitatewiththis
reagent.
•TestbyMayerreagent(Potassium-mercuric-iodidesolution):-
Alkaloidsgivecreamcolourprecipitatewiththisreagent.

11. •TestbyWagnerreagent(iodine-potassium-iodide
solution):-AlkaloidsgiveBrowncolourprecipitate
withthisreagent.
•TestbyHagerreagent(Saturatedsolutionofpicric
acid):-Alkaloidsgiveyellowcolourprecipitatewiththis
reagent.
•TestbyTannicacid:-Alkaloidsgivesbuffcolour
precipitatewiththisacid
•TestbyPicrolonicacid:-Alkaloidsgiveyellowcolour
precipitatewiththisacid.
Chemical Tests For Alkaloids…

12. Classification
Alkaloidsmaybeclassifiedinanumberofways.
Forexample:theymaybeclassified
1.Accordingtosource,
2.Chemicalstructure,or
3.Pharmacologicalaction.
Eachsystemhasitsownadvantagesanddisadvantages.
12

13. Alkaloids can be classified in another way
Types Features Examples
True alkaloids
Containnitrogeninaheterocyclicring,
derivedfromaminoacidsandnormally
occurinplants
Colchicine, quinine,
morphine, emetine etc.
Amino / Proto
alkaloids
Relativelysimpleamineinwhichthe
aminoacidnitrogenisnotina
heterocyclicring
Mescaline and
ephedrine
Pseudoalkaloids
Notderivedfromaminoacidprecursors
andareusuallybasicinnature
Conessineandcaffeine

14. Classification
Usually they are classified on the basis of the ring structure or nucleus of the
alkaloids as follows:
1.Pyridine-piperidinegroup
2.Tropane group
3.Quinolinegroup
4.Isoquinolinegroup
5.Indole group
6.Imidazole group
7.Steriodalgroup
8.Alkaloidal amino group
9.Lupinanegroup
10.Purine group

15. 1.Pyridine -piperidinegroup
The alkaloids in this group contain pyridine or
piperidinein the molecule. The important alkaloids in
this group are nicotine, coniine, arecoline, lobelineetc.
pyridine piperidine
Example:
nicotine coniineN N
H N
H
CH
2N
N CH
3
CH
2
CH
3
15

16. 2.Tropanegroup
Tropaneis a dicycliccompound where both pyrrolidine
and piperidinering system are present.
pyrrolidinepiperidine tropane
Example:
AtropineN
H
N
H
N-CH
3 N-CH
3
OCOCH
CH
2
OH
16

17. Natural sources:
•Plants of Solanaceaefamily are the major sources of tropane
alkaloids
•Different genus of the family Solanaceaee.g. Atropa,Datura,
Hyoscyamus,Scopolia,Duboisiaetc.
•Besides Solnaceae, they are also found in many species of
Erythroxylum(Family: Erythroxylaceae)
•The principal alkaloids of therapeutic interest are
hyoscyamine, atropine, and hyoscine

18. Belladonna (Deadly nightshade)
Biologicalsource:
•Belladonnaleafconsistsofdriedleafand
floweringorfruitingtopsofAtropabelladonna
LinnoritsvarietyacuminataofSolanaceae
family.
•Belladonnarootconsistsofdriedrootsof
AtropabelladonnaLinn.
•Family:Solanaceae
•Theplantisaperennialherbthatgrowsto1m
inheight.
•“Belladonna”isfromtwoItalianwords“bella”
meaningbeautifuland“donna”meaninglady.
•Thisprobablyreferstothefactthat,juiceofthe
berryofplantwhenplacedintheeyescauses
dilationofthepupilsgivinganoutstanding
appearance.
Atropabelladonna

19. •Chemical constituents:
✓Contains predominantly hyoscyamine
✓Other components include atropine, apoatropine, asparagine, choline,
chrysatropicacid, volatile bases such as pyridine, atroscine, leucatropicacid,
phytosterols, N-methylpyrrolidine, scopoletin, calcium oxalate, 14% soluble acid
soluble ash, and 4% insloubleash
•Uses:
✓It is used as anticholinergic, narcotic, sedative, diuretic & mydriatics
✓It relieves spasm of gut or respiratory tract
✓Consumption of Belladonna reduces excessive perspiration of patients suffering
from tuberculosis
✓It is also used to treat peptic ulcer disease, histaminic reaction, and motion
sickness.N CH
3
OCOCH CH
2OH
Hyoscyamine

20. Stramonium(Thorn apple/Jimson
weed/Jamestown weed / Devil’s apple)
Biological source
•Itconsistsofdriedleafandflowering
orfruitingtops(withbranches)of
DaturastramoniumLinnoritsvariety
TatulatorreyofSolanaceaefamily.
•Theplantisanannualherbthat
attainsheightofabout2m.
•Location:WidelyfoundinEurope,
Asia,andAmerica.Cultivatedin
Germany,France,Hungary,andS.
America
Daturastramonium

21. •Chemical constituents:
✓Contains hyoscyamineand hyoscine
✓Other alkaloids include tiglodine, metelodine, 3,6 dihydroxytropane,
norhyoscyamine, noratropine, hygroline, norhyoscine, littorine,
acetoxytropane, valtropine, tropine, pseudotropine, cuscohygrine
•Uses:
✓It is used as a narcotic, anticholinergic, mydriatic, anthelmentic,
anticancer, smooth muscle relaxant&sedative antispasmodic
✓Mainly used to relieve the spasmof the bronchioles in asthma
✓Also used for the treatment of Parkinsonism
✓Fruit juice is used to cure dandruff and falling hairN CH
3
OCOCH CH
2OH
Hyoscyamine

22. Hyoscyamus(henbane) / Insane root / Hog’s bean /
Poison tobacco / Black henbane / Folia hyoscyamus/
Khurasani-ajvayan
Biologicalsource
Hyoscyamusorhenbaneisthedried
leafwithorwithoutthefloweringor
fruitingtopofHyoscyamusnigerLinn
ofSolanaceaefamily.
Constituents
Thedrugcontainsabout0.05–0.15%
alkaloids(nolessthan0.04%).
Alkaloidsinclude
•Hyoscyamine
•Scopolamine
Hyoscyamusniger

23. •Chemical constituents:
✓Contains hyoscyamineand hysocine
✓Also contains hyoscipicrine, choline, metelodine, tiglodine, acetoxytropane
Hyoscyamine
•Uses:
✓It is used as a narcotic, mydriatic, antiseptic, purgative (Laxative), smooth
muscle relaxant, sedative antispasmodic (relieve spasm of involuntary
muscle)&CNS stimulant
✓Used to treat asthma and whooping coughN CH
3
OCOCH CH
2OH N CH
3
OCOCH CH
2OH
O
Hyoscine

24. 3.Quinolinegroup
Alkaloids containing the quinolinering as the principal nucleus are
quinine, quinidine, cinchonineand cinchonidine.
Quinoline
quinine
Natural sources:
Different species of the family Rubiaceaesuch as Cinchona
succirubra, Cinchona calisaya, Cinchona ledgereiana, C.
officinalis, Remijapedun-culata, R. purdieanaetcN N
CH
3
O
N
OH
24

25. Cinchona / Cinchona Bark / Peruvian bark
•Synonyms: Peruvian bark,
Cinchona, Calisaya bark, Jesuit’s
bark etc
•Source: Dried bark of stem or the
root of Cinchona succirubra,
Cinchona calisaya, Cinchona
ledgereianaor C. officinalis
•Family: Rubiaceae
•Geographical source: South
America. Cultivated in Indonesia,
Java, Zaire, India, Guatemala, and
Bolivia.

26. •Chemical Constituents:
✓It contains predominantly quinine (70%), quinidine, and cinchonine
✓Other constituents include quinovin, red coloring oxidase, calcium
oxalate, and starchN
N
HO
R
2
R
1
Quinine (R1 = OCH
3, R2 =α-H)
Quinidine(R1 = OCH
3, R2 = β-
H
Cinchonidine(R1= H, R2 = α-
H)
Cinchonine(R1= H, R2 = β-H)

27. •Uses:
✓It has antimalerial, antipyretic, and analgesic properties
✓Quinidine is used as prophylactic(intended to prevent
disease) for treatment of cardiac arrhythmias
✓Bark and other preparations are used in treating intermittent
fever
✓Act as antiseptic
•Side effects
✓Large doses of quinine cause loss of hearing, impaired sight,
weakening of heart & restlessness
✓Cause CNS disturbance, spasm, convulsion, abdominal pains,
paralysis of limbs, albuminuria etc.

28. 4.Isoquinolinegroup
The isoquinolinering occurs in a number of alkaloids in
widely separated plant families. For example:
papaverine, morphine, emetine etc.
Isoquinoline
papaverineN N
CH
3
O
CH
3
O
OCH
3
OCH
3
28
•Natural sources:
✓Ipecac, Opium, Berberis, Curare, and Sanguinaria

29. Ipecac
•Synonyms: Ipicacuanha, Brazilian
or Johor Ipeac, Hippo, Ipicacuanha
root
•Source: Dried root or rhizome of
Cephaelisipicacuanhaor C.
acuminata
•Family: Rubiaceae
•Geographical source: Indigenous to
Brazil, and also found in Colombia,
Nicargua, Malaya, Burma, Panama,
and India

30. •Chemical Constituents:
✓It contains predominantly emetine (30-75%)
✓Other alkaloids include cephaeline, psychotrinemethyl ether, protoemetine,
and emetamine
✓Other compounds include ipecacuanhin, ipicoside, traces of ipecamineand
hydroipecamine, malicacid, citric acid, saponins, starch, calcium oxalate and
resin
Emetin(R = CH
3)
Cephaeline(R = H)N
CH
2
NH
H
3CO
H
3CO
CH
3
HH
H
OCH
3
OR
•Uses:
✓It is emetic and used as an expectorant
✓It is used in the treatment of amoebic dysentery

31. Curare / (South American Arrow Poison)
•Synonyms: Ourari, Urari, Woorari,
S. American arrow poison, Wourara
•Source: Dried extract from the bark
and stems of Strychonscastelnaei,
S. toxifera, S. crevauxii, S.
jobertiana& C. microphylla
•Family: Loganiaceaeand
Menispermaceae
•Geographical source: It is generally
found in Southern America

32. •Chemical Constituents:
✓It contains several alkaloids and quaternary compounds
✓Most important compound is d-tubocurarinewhich is quaternary
compound
✓C. microphyllapossesses one quaternary base (+)-bebeerine while (-)-
bebeerine has been isolated from C. tomentosum
✓MenispermaceousCurarehas (+)-tubocurarine, (+)-
isochondrodendrine, isochondrodendrinemethyl ether, curineand (+)-
chondrocurine
✓Loganiaceous curare contains 12 crystalline quaternary alkaloids,
toxiferinesI-XII
BebeerineNCH
3
O
OH
O
H
3CN
OCH
3
H
3CO OH

33. •Uses:
✓Curare is used as source of alkaloids
✓Tubocurarinechloride has muscular relaxation effect in surgery and is
used to control convulsions of strychnine poisoning and of tetanus

34. Opium
•Synonyms: Crude Opium, Raw
Opium, Gum Opium, Afim
•Source: It is obtained by
incision from the unripe
capsules of Papaversomniferum
•Family: Papaveraceae
•Geographical source: Turkey,
Russia, Yugoslavia, Tasmania,
India, pakistan, Iran, Afganistan,
China, Myanmer, Thiland, Laos
and India

35. •Chemical Constituents:
✓Opium contains about 25 alkaloids, predominantly morphine (10-16%)
✓The alkaloids are combined with meconicacid
✓Different alkaloids are:
▪Morphine type: Morphine, codeine, neopine, pseudo-or oxymorphine,
thebaineand porphyroxine
▪Phthalideisoquinolinetype: Hydrocotarnine, narcotoline, L-narcotine,
noscapine, oxynarcotine, and narceine
▪Benzyl isoquinolinetype: Papaverine, xanthaline, D-L-laudanine,
laudanidine, codamine, and laudanosine
▪Cryptopinetype: Protopine, cryptopine
▪Unknown types: Aporeine, rhodeadine, meconidine, papaveramine
and lanthopine
✓The drug also contains sugars, sulphates, albuminouscompounds,
coloring matter, anisaldehyde, vanillin, vanillicacid, p-hydroxystyrene,
fumaricacid, lactic acid, benzyl alcohol, phthalicacid, hemipinicacid,
meconinand some odorous compounds

36. O
R
1O
R
2O
NCH
3 N
H
3CO
H
3CO
H
3CO
H
3CO O
OH
O
HOOC COOH O
O
OH
NCH
3
O CO
OCH
3
OCH
3 O
O
OCH
3
N
CO
COOH
OCH
3
OCH
3
H
3CO
CH
3
CH
3 O
H
3CO
H
3CO
NCH
3 Morphine (R1 = R2 = H)
Codeine (R1 = CH
3R2 = H)
Meconicacid
Narcotine
Thebaine Narceine
Papaverine

37. •Uses:
✓Opium and morphine have narcotic, analgesic, and sedative action
which are commonly used to reduce pain, diarrhea, dysentery and
cough
✓Poppy capsules are astringent, somniferous, sedative, and narcotic
✓Opium is first stimulant, then narcotic, anodyne, antispasmodic,
hypnotic, intoxicant, cerebral depressant, astringent and myotic
✓As astringent opium checks haemorrhages, lessens bodily secretions
and restrains tissue changes
✓Codeine is mild sedative and employed in cough mixtures
✓Nosocapineis non-narcotic and also has cough suppressant action
acting as a central antitussive drug
✓Papaverinehas smooth muscle relaxant action and used to cure
muscular spasms
✓Opium, morphine, and diacetylmorphine (heroin), cause drug
addiction

38. 5.Indolealkaloids
•These drugs contain indolenucleus in their structure
•The majorsources of indolealkaloids are Ergot, Nuxvomica, Physostigma,
VincaetcN
H
Indole

39. Rauwolfia
•Synonyms: Sarpagandha,
Chandrika, Chootachand,
Indiansnakeroot
•Source:Itisthedriedrootsof
Rauwolfiaserpentina.
•Family:Apocyanaceae
•Geographicalsource:Nativeto
India.AlsofoundinThailand,
Philippines, Indonesia,
Pakistan,Malaysia,and
Bangladesh

40. •Chemical Constituents:
✓It contains about 0.7-2.4% of total alkaloidalbases from which more
than 80 alkaloids have been isolated
✓The prominent alkaloids include reserpine, rescinnamine, γ-resepine,
rescidine, raunescineand deserpidine
✓The other alkaloidalcompounds include ajmalinine, ajmaline,
ajmalicine, serpentine, serpentinine, tetrahydroreserpine, raubasine,
reserpinine, isoajamaline, rauwolfinineand alstonine
✓Other substances include phytosterols, fatty acids, unsaturated
alcohols and sugar
Reserpine
Ajmaline Serpentine

41. •Uses:
✓It is used as hypnotic, sedative, and antihypertensive
✓It reduces blood pressure, and cures pain
✓It is employed in labors to increase uterine contractions and in certain
neuropsychiatric disorders

42. Ergot
•Synonyms: Ergot, Rye ergot, Scale
cornutum, Ergota, Ergot of rye
•Source: Dried sclerotiumof a
fungus, Clavicepspurpurea,
developing in the ovary of rye
plant,Secalecereale.
•Family: Clavicipitaceae
•Geographical source:
Czechoslovkia, Hungary,
Switzerland, Germany, France,
Yugoslovia, Spain, Russia and India

43. •Chemical Constituents:
✓A large number of alkaloids have been isolated of which important
alkaloids are ergonovineand ergotamine
✓Ergot alkaloids are classified as three groups:
1.Ergometrinegroup (Water soluble): Ergometrine, ergometrinine
2.Ergotamine group (Water insoluble): Ergotamine, ergotaminine, ergosine
and ergosinine
3.Ergotoxinegroup ( water insoluble): Ergocristine, ergocristinine,
ergocryptine, ergocryptinine, ergocornine, and ergocorninine
✓Other chemicals include histamine, tyramine, putrescine, cadaverine,
agmatine, amino acids, acetylcholine, coloring matters, ergosterol,
fungisterols, elymoclavine, sclereythrin, erggonovine, ergothioneine,
clavicepsin, betaine, clavine, fat, mannitol, lactic acid and succinicacid
Ergometrine

44. •Uses:
✓Ergot is oxytocic & vasoconstrictor
✓Ergot is used to assist delivery and to reduce postpartum hemorrhage
✓Also used to treat migraine

45. Nuxvomica
•Synonyms: Nuxvomicaseeds,
Kuchla, Quaker buttons,
Bachelor’s buttons, Posionnut
•Source: It is the ripe, dried seed
of Strychonsnux-vomica
•Family: Loganiaceae
•Geographical source: Native to
East India and forest of Srilanka,
Malabar coast, and N. Australia.

46. •Chemical Constituents:
✓Important alkaloids are strychnine and brucine
✓Other alkaloids include α-colubrine, β-colubrine, icajine, 3-
methoxyicajine, protostrychnine, vomicine, novacine, N-oxystrychnine,
pseudostrychnine, and isostrychnine
✓Other compounds include chlorgenicacid, loganin, secologanin, fixed
oil (3%), and proteins
BrucineStrychnine

47. •Uses:
✓Strychnine is used as circulatory stimulant and bitter tonic
✓It increase the tone of intestine
✓Strychnine improves the appetite and digestion
✓It is a powerful poison at large doses, producing tetanicconvulsion and
death

48. 6.Imidazolealkaloids
•These drugs contain imidazole nucleus in their structure
•The majorsources of imidazolealkaloids are Pilocarbusjaborandi, P.
pinnatifolius, P. microphyllusand P. racemous
Imidazole

49. •Source: Pilocarpusjaborandi or P. microphyllus(Fam: Rutaceae)
•Properties:
✓Principle alkaloids are Pilocarpineand isopilocarpine
✓Other alkaloids are Pilocarpidine, Pilosineetc.
•Uses:
•Has parasympathomimeticactivity
•It is used in the treatment of glaucoma
PilocarpusN
N O O
CH
2CH
3
CH
3
Pilocarpine

50. 7.Purine alkaloids
•These drugs contain purine base in their structure
Pharmaceutically importantbases of this group are methylated
derivatives of 2,6-dioxypurine (Xanthine)
▪Caffaineor 1,3,7-trimethyl xanthine
▪Theophylline or 1,3-dimethyl xanthine
▪Theobromineor 3,7-dimethyl xanthine

51. Coffea
Biologicalsource:
Itisthedried,ripeseedsofCoffeaArabicaorC.liberica
Family:Rubiaceae
Geographicalsource:
ItisindigenoustoEthiopiaandotherpartsofEasternAfricaandiswidelycultivatedin
tropicalcountrieslikeIndonesiaandSriLankaandcentralandSouthAmerica.
Constituents:
Itcontains-
Caffeine(1-2%)
Trigonelline(0.25%)
Tannin(3-5%)
Sugar(15%)
Fattyoil(10-13%)
Protein(10-13%)
Use:
▪CaffeineisthemainprinciplewhichisCNSstimulant
▪Itreducesphysicalfatigueandrestoresalertnesswhendrowsinessoccurs
▪Itproducesincreasedwakefulness,fasterandclearerflowofthought,
increasedfocus,andbettergeneralbodycoordination
▪Itisadiuretic
Caffaine

52. Tea/Thea
Biologicalsource:
TeaisthepreparedleavesorleafbudsofCameliasinensis
Family:Theaceae
Geographicalsource:
ItisindigenoustoEasternAsia.ItisextensivelycultivatedinBangladesh,China,
Japan,IndiaandIndonesia.
Constituents:
Teacontains-
Caffeine(1-4%)
Adenine
Theobromine
Theophylline
Xanthine
gallotannicacid
volatileoiletc.
Use:
Asbeverage
Stimulant&Diuretic
Theophylline

53. 8.Steroidal group
Thesteroidalalkaloidsarecharacterized bythe
cyclopentanoperhydrophenanthrenenucleus.Theimportantalkaloids
areprotoveratrineAandB,Aconitine,conessineetc.
Example:
Cyclopenteno-perhydro-phenanthrene
Conessine N
N
CH
3
CH
3
CH
3
CH
3
53

54. Veratrumviride(green hellebore)
Biologicalsource
ItisdriedrhizomeandrootsofVeratrumviride
Family:Liliaceae
•Itisaperennialherbattaining0.7to2mheight.
Constituents
Itcontainsalargenumberofalkaloidsasfollows-
▪Estersofalkamines(steroidalbases):Germidine,germitrine,cevadine,
protoveratrineetc.
▪Glucosidesofalkamines:Pseudojervine,veratrosine.
▪Thealkamines:Jervine,rubijervine,germineetc.
Amongthemgermidineandgermitrinearemostimportanttherapeutically.
Use
▪Itpossesseshypotensive,cardiacdepressantandsedativeproperties.
▪Itisusedinthetreatmentofhypertension.
▪Asinsecticide.

55. Veratrumalbum
(white hellebore)
Biologicalsource
•ItisdriedrhizomesofVeratrumalbum.Itisalsoaperennialherb
buttheexternalcolorislightercomparetoV.viride.
Family:Liliaceae
Constituents
•SimilartoV.viride.TwoesteralkaloidsprotoveratrineAand
Baremostactive.
Use
•Ithashypotensiveproperties
•Asinsecticides

56. Aconite napellus
Biologicalsource
•ItisdriedtuberousrootsofAconitumnapellus.Theplantis
perennialherb.
Family:Renunculaceae
Constituents
•Itcontainsaconitine,aconineandaconiticacidetc.
Use
•Hascardiaceffectbut
•Principallyusedaslocalanalgesicinliniments

57. 9.Lupinanegroup
Thealkaloidsinthisgroupcontainadicycliclupinane
ring.Forexample,Sparteine,lupinineetc.
Lupinane
Example:
LupinineN N
CH
2
OH
57

58. Lupinusluteous
Biologicalsource
•LupinusisobtainedfromLupinusluteus.
•Theplantisanannualherbandcultivatedas
ornamentalplant.
Family:Fabaceae
Constituents
•ImportantconstituentsisLupinine.
Use
•Notmedicinallyimportant.

59. Cytisusscoparius
BotanicalSource
ItisthedriedtopsofCytisus
scoparius.
Family:Leguminosae
Constituents
•ItsmainconstituentsareLupinane
alkaloidsincludingSparteineand
flavonoids.
Use
•Itisanoxytocicandisusedinthe
treatmentofuterineinertia.

60. 10.Alkaloidalamine group
Thealkaloidsinthisgroupdonotcontainheterocyclicnitrogen
atoms.Forexample,Colchicine.Somearesimplederivativeof
phenylalaninelikeephedrine,mescalineetc.
Example:
Colchicine
Phenylethylamine EphedrineOOMe
MeO
MeO
NH
OMe
COCH
3 NHCH
3
OH NH
2
60

61. Ephedrasinica(Ma huang)
Biologicalsource
•ItistheentireplantortheovergroundportionofEphedrasinica.
•Theplantisalow,dioecious(maleandfemalereproductiveorgansondifferent
plants)practicallyleaflessshrubthatattain60-90cm.height.
Family:Gnetaceae
Constituents
•Theimportantconstituentisephedrine.Itmayalsocontainpseudoephedrine
andsomeotherrelatedcompounds.
Use
•Ephedrineisapotentsympathomimetic(excitesthesympatheticnervous
system).
•Itraisesbloodpressureandcausesmydriasisandactasbronchodilator.

62. Colchicum autumnale
Biologicalsource
•Itisdried,ripeseed(orcorn)ofColchicumautumnale.
•Twotosixflowerswithlongperianth(outerpartofaflower)tubedevelop
fromtheundergroundplant.Thearabshadrecommendedtheuseof
colchicuminthetreatmentofgout.
Family:Liliaceae
Constituents
•Itcontainscolchicine,colchicinelikealkaloids,resin,fixedoilandreducing
sugars.Theseedcontainsupto0.8%colchicine(corncontains0.6%
colchicine).
Use
•Itisusedinthetreatmentofgout.

63. Detectionofpurinealkaloids:
Purinealkaloidsdonotrespondtothenormaltestsofalkaloids.These
alkaloidsaredetectedusingMurexidetest.
IntheMurexidetestthesampleofalkaloidistakeninabeakerandsmall
amountofpotassiumchlorate(KClO
3
)andadropofconc.HClwere
added.Thenthecontentofthebeakerwasevaporatedtodryness.The
beakerwasthenexposedtoNH
3
vapor.Apurple/pinkcolorindicatesthe
presenceofpurinealkaloids.

64. Extraction of alkaloids

65. Extraction of alkaloids
Process I
65

66. Description
•Thepowderedmaterialismoistenedwithaqueousalkali[water
andmixedwithlimewhichcombineswithacids,tanninsandother
phenolicsubstancesandsetsfreethealkaloids(iftheyexistinthe
plantassalts)].
•Thealkaloidsaresetfreewithotherplantconstituents.
•ExtractionisthencarriedoutwithorganicsolventssuchasBenzene
orchloroform(eitherorpetroleumspirit).
•Theconcentratedorganicliquidwhichcontainsalkaloidsandother
plantconstituentsisthenextractedwithdiluteacid(aqueousacid)
andallowedtoseparate.
•Alkaloidsaltsarenowintheaqueousliquid,whilemanyimpurities
remainbehindintheorganicliquid.
•Aqueousalkaliisaddedtotheaqueouslayergivingprecipitationof
freealkaloids.

67. Process II
67

68. Description
•Thepowderedmaterialisextractedwithwaterofaqueous
alcoholcontainingdiluteacid.
•Wegetalkaloidalsaltsandotherplantconstituents.
•Pigmentsandotherunwantedmaterialsareremovedby
shakingwithchloroformorotherorganicsolvents.
•Thenwegetaqueouslayercontainingalkaloidalsalts.
•Thefreealkaloidsarethenprecipitatedbytheadditionof
aqueousalkali(excesssodiumbicarbonateorammonia)and
separatedbyfiltrationorbyextractionwithorganicsolvents.

69. Biosynthesis of Tropanealkaloids
•Tropaneisformedbythecondensationofpyrrolidinecompoundwith
3acetatederivedcarbonatoms.
•Thepyrrolidineringisformedfromaminoacidornithine.
•Theremaining3carbonatomsarederivedfromacetateand
methylationresultsinthecompletionofthetropinenucleus.
•The3-hydroxyderivativeoftropaneiscalledtropine.
•Ontheotherhandfromphenylalaninetropicacidisformedvia
rearrangementandotherreactions.
•Esterificationoftropineandtropicacidresultsintheformationof
HyoscyamineandthusotherTropanealkaloidsaresynthesized.

71. Biosynthesis of TropaneAlkaloid

73. Biosynthesis of Cocaine

74. Biosynthesis of QuinolineAlkaloids
•TheprecursorofquinineandotherQuinolinealkaloidsis
Tryptophan.
•Itsbiosynthesisinplantisnotfullyunderstoodbutin
microorganismsitisobtainedviashikimicacidpathway.
•
•Inthispathway,shikimicacidthroughaseriesphosphorylation
reactionyieldschorismicacid.
•Chorismicacidisanimportantbranchpointwhereonebranch
leadstoprephenicacidandthentoaromaticaminoacidslike
tyrosine,phenylalaninewheretheotherbranchleadtoanthralinic
acidandthentoTryptophan.
•Tryptophanandcorynanthelikemonoterpeneformcorynantheine
whichyieldquinine.

75. Biosynthesis of Tryptophan in Microorganism

77. Biosynthesis of IsoquinolineAlkaloids
•FromphenylalanineoftyrosinePhenylethylaminederivatives
andphenylacetaldehydederivativesareobtainedwhichare
condensedtogiveIsoquinolinealkaloids.
•Morphine(andcodeine,thebaine)isalsoformedfrom
tyrosine(2molecules)andinthebiosyntheticpathway
Norlaudanosolineisakeyintermediate.

79. Biosynthesis of IndoleAlkaloids
•Theprecursorofindolealkaloidsistryptophanand
monoterpenoidskeleton.
•Alkaloidslikereserpine,serpentinearesynthesizedfrom
tryptamineandcorynanthemonoterpenoidprecursor.
•Theergotalkaloidsaresynthesizedbyalkylationof
TryptophanbyDMAPP(Dimethylallylpyrophosphate)as
illustratedbelow: