for sem 5 students GTU

1. Secondary metabolites and
its detail information
Pooja H. Khanpara
Asst. professor
Pharmacognosy
Aksharpreet College of Pharmacy, Lakhabaval,
Jamnagar

2. Alkaloids

3. Definition
The term “alkaloid” (alkali-like) is commonly used to
designate basic heterocyclic nitrogenous compounds of
plant origin that are physiologically active. Derived from
amino acids.

9. 1. Stass otto method
Powdered plant material
Defatted with non-polar solvent
Defatted plant material
Moist with water and treated with NH3, Dil. Lime solution (Free Alkaloid)
Extracted with organic solvent like chloroform, ether
Extract, Concentrate it
Dissolved in Dil. Acid (Alkaloidal salt)
Aqueous phase Organic phase impurities
Basified with ammonia or sodium
Bi-carbonate or Dil. KOH
Aqueous phase Organic phase(Free Alkaloid)
Evaporate to dryness
Crude Alkaloids

12. 2. Manske’s method
Powdered Crude material
Defatted with non-polar solvent
Defatted Crude material
Extract with methanol
Methanol Extract
Concentrate
Dissolve in water and Acidified it upto pH 2 (Alkaloidal salt)
Steam Distillation to remove traces of methanol
Stand for several days in refrigerator
OR boiled with paraffin
Filter
Filtrate
Shake with organic solvent like chloroform or ether
Aqueous phase (Alkaloidal salt) Organic phase
Basified with ammonia or sodium
Bi-carbonate or Dil. KOH
Aqueous phase Organic phase
Evaporate to dryness
Crude Alkaloids

14. 4. Kippenberger’s Process
Powdered and sieved plant substance is first and foremost
digested with solution of tannin (100 g) in glycerol (500 g) at a
constant temperature of 40°C for a duration of 48 hours.
The resulting mixture is further heated to 50°C so as to help in
the complete coagnlation of proteinous substances, cooled to
ambient temperature and finally filtered.
The resulting filtrate is thoroughly shaken with petroleum ether
to get rid of faulty materials (oils, fats and waxes), and the last
traces of petroleum ether is removed from the extract by
heating either on a water-bath (electric) or exposure to Infra-
Red Lamp.
The fat-free crude plant extract is subsequently acidified and
shaken with chloroform.
Chloroform extract contain alkaloids.

16. Fractional crystallization
Ephedrine & Pseudoephedrine Oxalates
Crystallization from water
Ephedrine Oxalate
Crystals
Pseudoephedrine Oxalate
Solution
Atropine & Hyoscyamineine Oxalates
Crystallization from
Acetone/Ether
Atropine Oxalate
Crystals
Hyoscyamine Oxalate
Solution

25. A) True alkaloids
Sr. no. Type Structure Examples
1. Pyrrole and
pyrrolidine
N
H
N
H
e.g. Hygrine, coca species
2. Pyiridine and
piperidine
N N
H
e.g. Arecoline, anabasine, lobeline,
conine, trigonelline
3. Pyrrolizdine
N
e.g. Echimidine, senecionine,
seneciphylline
4. Tropane
N
e.g. Atropine, hyoscine, hyoscyamine,
cocaine, pseudopelletirine
5. Quinoline
N
e.g. Quinine, quinidine, cinchonine,
cupreine, camptothecine
6. Isoquinoline
N
e.g.Morphine, codeine, emetine,
cephaline, narcotine, narceine, d-
tubocurarine

26. 7 Indole
N
H
e.g. Erotamine, ergotametriene,
reserpine, vincristine, vinblastine,
strychnine, brucine
8 Imidazole N
N
H
e.g. Pilocrpine, isopilocarpine, pilosine
9 Norlupinane
N
e.g. Cystisine, laburinine
10 Piporphine
(reduced
isoquinoline
napthalene)
N
e.g. Boldine

28. B) PROTOALKALOID
1. Alkyalamine
HO
NH
Ephedrine, Pseudoephedrine
C) Pseudoalkaloid
1. Purine
N
NN
HN
e.g. Caffeine, thophylline, theobromine
2. Steroidal e.g. Solanidine, conessine,
protoveratrine
3. Diterpene C20H32 e.g. Aconitine, aconine, hypoaconine

32. G.S.: central & south europe, england, germany, america, india(kulu, kashmir, simla)
Atropa acuminata (indian)

33. Cultivation & collection:
Seed sawn in nursary, then seedling transplanted in deep well
drained, moist, calcareous soil & loamy soil in April.
Weeding & fertilizing are needed.
Leaves Collected in dry summer weather next 4 ft. hight, flowring
15th june to 15th july.
From 2nd cut plants harvesting are done in August & september and
sometime in october.
Root are dug out at 4th year
Drug dried at 40 – 60 °C in dark sheds.

35. Commercial uses
The alkaloids are compounded with phenobarbital or kaolin &
pectin for use in various functional gastrointestinal disorders.
Belladonna tincture
Decoction
Powders
Alkloidal salt

36. Isoquinoline Alkaloid
Afim, Afin
G.S.: turkey, Yugoslavia(macedonia), india, pakistan, Iran, china, thiland, pakistan

38. morphology
Paramet
er
Indian
Opium
Persian Opium N. Turkish or
Europian
Maupaleted
Turkish
Menuplated
Europen
Odour Strong
chs.
Strong chs. Strong chs. Strong chs. Strong chs.
Taste bitter bitter bitter bitter bitter
Color Dark
brown
Dark brown Dark brown
Or brown
Chocolate
brown or
dark brown
Dark brown
Shape Cubical
piece
Brick Conical or
round
flattened
Oval
flattened
Elongated
masses with
flattend rounded
end
weight 900 gm 450 gm 250-1000 gm 2000 gm 150-500 gm
nature Brittle &
plastic
Hygroscopic,
granular or
smooth
fracture
Hard & brittle
covered with
poppy leaves
Plastic or
brittle ,
covered
with poppy
hard, plastic,
brittle covered
with poppy
leaves

50. Commercial uses
In Mfg. of Morphine, codeine, narcotine, papaverine.
Morphine then semisynthesized and form heroin/dimorphine, ehich
has more narcotic analgesic property than morphine.
Poppy seeds – drying oil – used in mfg. of paint, varnishes, soaps,
food and salad dressing.
Oil cake is good for cattle.
Seeds used for preparation of emulsion.
Poppy stems used for straw.

55. Commercial uses:
Wood – carving & turning hobbyists.

60. C & C: Tyloindicine – A,B,C,D,E,F
Chemical Test: Mayer’s, Dragendroff’s, Hager’s, Wagner’s tests
Use: Hepatoprotective, Anti-allergic, Diuretic, Anticancer, Anti-
asthamatic, cardiac activity, Imunomodulatory activity
Commercial use:
As an ornamental
To extract vincristin, vinblastin, reserpine
In cancer therapy.

61. Phenyl Propanoids and Flavonoids

62. Introduction of Phenyl Propenoids
Its containing organic compounds with six-carbon, aromatic
phenyl group & 3 carbon propene ring.

63. Functions
For polymers
Provide protection from UV light.
Protect plant from herbivores & pathogens
Classification
1) simple: Cinnamyl alcohol, acids, amides, aldehyde,
phenylpropane.
2) complex: phenylethans, lignans, xantholignans, alkaloidlignan

64. Introduction of Flavonoids
Also called Bioflavonoid
It consist 2 phenyl ring (A & B), 1 heterocyclic ring. (C6-C3-C6)
Function: As best pollinator, flower coloration(red/yellow
pigmentation)
Nitrogen fixation,UV filtration, Chemical messengers.

65. Classification of flavonoid
Flavones
Flavonols
Flavanone
Flavanonols
Isoflavones
Flavanols
Anthocynidine
Chalcones

66. Lignans
Non flavonoids compound
Derived from Phenylalanine by Shikkimic acid pathway.
It is linked with glycosylate derivatives. E.g. Flaxseed
(secoisolariciresinol)
Basic structure consists of 2 phenylpropane units
Functions:
protection against herbivores & microorganisms.
Antioxidant & antiinflammatory action
Classified as Furans, Furofurans, dibenzylbutane,
dibenzylbutyrolactone, aryl tetralins, aryl napthalens.,etc…..

70. RUTA
Syn: Rue, Garden rue, Sadab, German Rue
B.S.: it consists of fresh & dried leaves of Ruta graveolance L.
Family: Rutaceae
G.S.: Native Balkan Peninsula, now worldwide gardens.
C.C.: Rutin & quercetin ( Flavonoid Glycosides)
gravioline (Alkaloid)
Uses : Headache, arthritis, cramps, spasms, cold, fever, aphrodisiac
As bitters, aromatic stimullant, suppression of menses.
In Food beverages

71. 71