Pharmacognosy, Phytochemistry, Steroids, Cardiac Glycosides, Triterpenoids

1. Pharmacognosy & phytochemistry
b.Pharma 3rd YeAr UNIT-2ND
Mr. Bulet Kumar Gupta
Assistant Professor
Sai College of Pharmacy, Mau

2. Alkaloids
•Alkaloids are the nitrogenous compounds, basic in nature and contain
one and n nitrogen atom in their heterocyclic ring.
•Alkaloids are secondary metabolites which are synthesized from from
Shikimic pathway.
•W.Meissner, gave the name alkaloids to nitrogen-containing basic
compounds, obtained from plants.
•Ladenburg stated alkaloids as, 'compounds originated from plants with
a basic nature, having one or more nitrogen atom in its ring structure'.
•The basic nature of alkaloids is due to the presence of N-atom in the
five or six membered ring structure.

3. Classification of Alkaloids
True alkaloids – It contain Nitrogen in the Heterocyclic ring and
originate from amino acids.
Example- Atropine, Nicotine, and Morphine.
Proto alkaloids - Which contain Nitrogen (but not the nitrogen
heterocyclic ring) and also originate from amino acids.
Example- Mescaline, Adrenaline and Ephedrine.
Pseudo alkaloids - Not derived from Amino acid
Example- Caffeine, Theo bromine, Theacrine and Theophylline
DRUGS:-
1) Vinca 3) Opium
2) Rauwolfia 4) Belladona

4. Chemistry of Alkaloids
A) N-Atom in the Molecule: Along with carbon, hydrogen, and oxygen,
the most essential component of alkaloids is the N-atom.
Alkaloids should have at least one or more N-atoms in a molecule.
Example- Cocaine has one nitrogen atoms in its structure.
In case of Pilocarpine N- atoms are part of heterocyclic ring.
In case of Ephedrine & Mescaline, N-atoms are present in the aliphatic
side chain.

5. B) O-Atom in the Molecule:
Along with C, H and N, some alkaloids carry O- atom.
Alkaloids of this category are basically solid alkaloids e.g., Pilocarpine.
C) Basicity (Alkalinity): Presence of N-atom in the alkaloid molecule
gives it a characteristic basic or alkaline reaction, thereby resulting in the
formation of their respective salts on reacting with many acids.

6. Stability of Alkaloids:
Generally alkaloids are not much stable as they degrade or decompose
not only when exposed to chemical reagents but also on exposure to air,
light, moisture, and heat.
Biogenesis
The alkaloids cannot be synthesised via common biosynthetic pathway
due to their different chemical structures. The alkaloids are derived from
amino acids acting as alkaloidal precursors, e.g., phenylalanine, tyrosine,
tryptophan, histidine, anthranilic acid, lysine, and ornithine.
Many amino acids are obtained from shikimic acid biosynthesised by
metabolism of carbohydrates in plants.

7. Qualitative Analysis of Alkaloids

8. Isolation & Extraction of Alkaloids by Stas-Otto Pro

10. Therapeutic uses of Alkaloids

11. Commercial application of alkaloids
The Commercial application of alkaloids are given below---
1) As Medicines
Examples- Codeine is used as a cough Supressants.
Digoxin is used in Heart failure and its improve heart functioning.
Vincristine used as an anticancer agent.
2) As an insect repellents & Pesticides
Examples- Pyrethrine is an insect repellents, it is added in mosquito
coils, Pesticides also.
3) For research & Scientific Study
4) Huntering of Animals
Examples- D-tubocurarine (Arrow poison)

12. Vinca alkaloid
Synonyms- Sadabahar, Periwinkle, Catharanthus
Biological Source- Vinca is dried whole plant of Catharanthus roseus
or Vinca roseus.
Family- Apocynaceae
Geographical Source
Vinca is native to Madagascar. It is grown as an ornamental plant in
India, South Africa, U.S.A., Europe, Australia, and Caribbean islands.

13. Macroscopic Features -
1) Colour: Leaves are green, roots are pale grey, and flowers are violet
pink- white or carmine-red coloured.
2) Odour: Characteristic.
3) Taste: Bitter.

14. Chemical Constituents
Vinca contains a large number of indole alkaloids, of which around 20
dimeric indole dihydroindole alkaloids exhibit oncolytic activity,
vincristine and vinblastine being the most significant ones. Vinblastine
contains catharanthine (an indole alkaloid part) and vindoline (a
dihydroindole alkaloid part).

15. Therapeutic Uses
1) Its leaves and stems are a source of alkaloids, which have antitumour
and anticancer properties.
2) Its leaves are used for controlling diabetes and high blood pressure.
3) Its alkaloids are sedative and tranquiliser.
4) It relieves muscle pain and depression.
5) It controls nosebleeds, bleeding gums, mouth ulcers, and sore throats.

16. 6) On internal administration, it is helpful in gastritis, enteritis, diarrhoea,
diabetes, etc.
7) It ensures brain health as the active ingredients improve blood supply
to the brain and increase the oxygen level that brain can utilise.

17. Rauwolfia alkaloid
Synonyms- Rauwolfia root, Serpentina root, Chhotachand, Sarpagandha
Biological Source- Rauwolfia is the dried roots of the plant Rauwolfia
serpentina.
Family- Apocynaceae
Geographical Source
Various species of rauwolfia are found in the tropical regions of
America, Africa, and Asia. It is commercially cultivated in America,
Thailand, Myanmar, Sri Lanka, and India. In India, it is cultivated in
Gujarat, Maharashtra, Karnataka, West Bengal, Tamil Nadu, Orissa,
Bihar, and Uttar Pradesh.

18. Macroscopic Features -
1) Colour: Root bark is greyish yellow to brown
2) Odour: Odourless.
3) Size: Diameter is around 1-3cm and length is 10-18cm.
4) Shape: Roots are sub-cylindrical in shape
5) Taste: Bitter.
Chemical Constituents-
Reserpine
Rescinnamine
Rescidine & Yohimbine
Ajmaline & Ajmalinine
Serpentine & Serpentinine

19. Therapeutic Uses
1) It is a hypotensive drug having a strong sedative property.
2) It is a mild tranquiliser used for removing low level of anxiety.
3) It is a rich source of indole alkaloids (such as reserpine, ajmaline,
ajmalicine, and serpentine), which are used in the treatment of
circulatory disorders.
4) Its roots are used in lowering blood pressure due to the presence of
reserpine which dilates the blood vessels, depresses the CNS activity
5) Deserpidine and rescinnamine are also used as hypotensive and
tranquilliser.
6) It is also used as an antianxiety, antipsychotic (neuroleptic), hypnotic
and sedative drug.

20. Belladona alkaloid
Synonyms- Deadly nightshade, Belladona Leaf, Belladona Folium.
Biological Source- Belladonna is the dried leaves and flowering tops of
the plant Atropa belladonna.
Family- Solanaceae
Geographical Source
Belladonna is native to Europe, North Africa, and Western Asia. In India,
belladonna is found in the western Himalayas from Shimla to Kashmir
and also in some neighbouring areas of Himachal Pradesh. The main
habitat of belladonna includes the forests of Sindh, Chenab valley, and
Jammu.

21. • Macroscopic Features
• 1) Colour i) Leaves: Green to brownish-green. ii) Flowers: Purple to
yellowish-brown. iii) Fruits: Green to brown.
• 2) Odour: Slight and characteristic.
• 3) Taste: Bitter and acrid.
• Chemical constituents
• Hyoscyamine (large)
• Pyridine & N-Methylpyrolline(Less)
• Scopoletine
• Calcium oxalate crystals

22. Therapeutic Uses
1) It is also used to decrease the secretion of sweat, gastric juice, and
saliva.
2) It is used in breathing abnormalities in infants.
3) It is used for reducing sweat and other secretions.
4) It is effective against tonsilitis, meningitis, scarlet fever, whooping
cough, and epilepsy.
5)Powdered preparations are used to treat asthma.
6) It can lessen headaches related to migraine
7) It is used as an analgesic in pain due to kidney stones, sore throat, etc.
8) It is useful in liver and gall bladder disorders.

23. Opium alkaloid
Synonyms- Afeem,Raw opium, Gum Opium.
Biological Source- Opium is the dried latex extracted from the unripe
capsules of the plant poppy or Papaver somniferum Linn.
Family- Papaveraceae
Geographical Source
Opium is commercially cultivated in Afghanistan, Yugoslavia, Bulgan
Pakistan, Turkey, Persia (Iran) and India. In India, it is mostly grown in
Madhy Pradesh.
Macroscopic Features
1) Colour & Shape- It is depend on the types of Opium like- Indian
opium, Persian Opium, European Opium (Dark Brown).

24. 2)Odour: Strong characteristic.
3) Taste: Bitter.
Chemical Constituents
1)Benzylisoquinoline: Narcotine (noscapine), narceine, and papaverine.
2) Phenanthrene: Morphine, codeine (methyl morphine), and thebaine.

25. Therapeutic Uses
1. It is use as a Sedative & Hypnotics.
2. It is use as an Analgesics (in severe Pain).
3. Morphine has central narcotics effects and causes Addiction.
4. It Stimulation of Chemoreceptor zone in medulla which cause
Nausea & Vomiting (side effects).
5. Its have Antitussive Properties
6. It is use as a Muscles relaxants.

26. PHENYLPROPANOIDS AND FLAVONOIDS LIGNANS
TEAAND RUTA
Phenylpropanoids
• The phenylpropanoids are naturally occuring phenolic organic
compounds with an aromatic ring and a three-carbon propene tail of
coumaric acid, and are synthesized by plants from the amino acids
phenylalanine and tyrosine via shikimic acid pathway.
Caumaric acid Cinnamic acid

27. The phenylpropanoid pathway starts from the aromatic amino acid
phenylalanine.
Phenylpropanoid compounds constitute a broad range of structural cyclic
substances.
They are formed as a result of deamination of the amino acid
phenylamine by the enzyme phenylalanine-ammonia lyase (PAL).
Classification
1) Hydroxycinnamic Acids: p-Coumaric acid, Caffeic acid, Ferulic acid
2) Phenylpropenes: Eugenol, Anethole, and Cinnamaldehyde.
3) Coumarins: Coumarins, Hydroxycoumarins, and Furanocoumarins.
4) Biphenylpropanoids Derivatives: Lignans and Flavonoids.
5) High molecular weight phenylpropanoids: Lignins & Tannins.

28. Biosources
Phenylpropanoids are obtained from a variety of plants such
as:
1) Hydroxycinnamic acids from Aloe barbadensis (Aloe vera).
2) Phenylpropane from cinnamomum verum (Cinnamom) and
Myroxylon balsamum (Balsum of tolu).
3) Caumarin from Acacia & Artemisia dracunculus
(Tarragon).
5) Biphenylpropanoid derivatives from Podophyllum
hexandrum

29. Flavonoids
Flavonoids are a diverse group of phytonutrients (plant chemicals) found
in almost all fruits and vegetables. Along with carotenoids, they are
responsible for the vivid colours in fruits and vegetables.
Flavonoids are chemically polyphenolic compounds.
They contain 15 carbon atoms. Two benzene rings joined by a linear
three carbon chain.

30. Flavonoids are defined as 'a large group of biologically active water-
soluble plant compounds (such as anthocyanins and flavones) that
include pigments ranging in colour from yellow to red to blue, and
occurring especially in fruits, vegetables.
Classification
1) Flavones 6) Flavanonols
2) Isoflavone 7) Flavanols
3) Flavanols 8) Anthocyanidins
4) Neoflavanoids 9) Chalcones
5) Flavanones

31. Source of Flavonoids

32. Therapeutic Uses of Flavonoids

33. Lignans
• The lignans are a large group of low molecular weight polyphenols
found in plants, particularly seeds, whole grains, and vegetables.
• Lignans are precursors to phytoestrogens.
• Lignans and lignin differ in their molecular weight, the former being
small and soluble in water, the latter being high polymers that are
undigestable.
• Flax seeds and sesame seeds contain high levels of lignans.
• Other foods containing lignans include cereals (rye, wheat, oat and
barley), soybeans, tofu, cruciferous vegetables, such as broccoli and
cabbage, and some fruits, particularly apricots and strawberries

36. Tea
Tea is an aromatic beverage prepared by pouring hot or boiling water
over cured or fresh leaves of Camellia sinensis,After plain water, tea is
the most widely consumed drink in the world.
Synonyms- Folia thea
Biological Source- It is leaf buds and leaves of the plant Thea sinensis.
Geographical Source- Southwestern China
and northern Myanmar.

37. • Chemical Constituents of Tea
• Caffeine (Trimethyl xanthine)
• Tannin
• Theophylline
• Theobromine (Dimethyl xanthine)
• Volatile oils
Chemical Test

39. Ruta
• It is Hardy, evergreen herb with a woody stem at the lower part.
• Its leaves are blue-green in color.
• It is commonly known for its terrible smell and bitter taste which is
used for the plants to keep insects away.
• Its fruits are 4-5 lobbed capsules which contains numerous seeds.

40. • Synonyms- Common Rue, Garden Rue, German Rue.
• Biological Source- Ruta is obtained from the fresh and dried leaves of
the plant Ruta graveolens L.
• Geographical Source- Mediterranean or Western Asia.
• Parts used: aerial parts, harvested in the flowering season.
• Chemical Constituents of Ruta
• Main active flavonoids- Rutin & Quercetin
• Acridone alkaloids
• Caumarins
• Volatiles substances
• Terpenoids

41. Therapeutic uses

42. Steroids, Cardiac Glycosides & Triterpenoids:
Steroids comprise a group of cyclic organic compounds whose basis is
characteristic arrangement of seventeen carbon atoms in a four ring
structure linked together from three 6-carbon rings followed by a 5
carbon ring and an eight carbon side chain on carbon 17.
These are classified into Five categories depending upon type of
substituent group (group-R) on C-17.
1. Sterols: where R is an aliphatic side chain. They contain usually 1 or
more hydroxyl groups attached in alicyclic linkage.
2. Sex hormones: where R bears ketonic or hydroxyl group and mostly
possess a two carbon side chain.

43. 3. Cardiac glycosides: where R is a lactone ring, the glycosides also
contain sugars linked through oxygen in other parts of the molecule.
4. Bile acids: where R is essentially a 5 carbon side chain ending with a
carboxylic acid molety.
5. Sapogenins: where R contains an oxacyclic (ethereal) ring system.
Sterols they are further subdivided into 3 categories
A) Zoosterols: such sterols that are obtained from animal kingdom only.
E.g. Cholesterol
B) Phytosterols: those which are derived from plant sources.
E.g. Stigmasterol

44. C) Mycosterols: Those which are obtained from eimer yeast or fungi.
E.g. Ergosterol
B) Phytosterols: Phytosterols are also termed as phytosterolds, occur in
plants, have similarity to cholesterol and divided into two sub categories
namely:
I) Sterols: having double bond in sterol ring structure. E.g. sitosterols
and campesterol
II) Stanols: It is saturated sterols, having no double bonds in the sterol
ring structure. E.g. sitostanol and campestanol.
More than 200 sterols and related compounds have been identified.

45. Chemical Structure of Steroids
The steroid nucleus (core structure) is called gonane
(cyclopentanoperhydrophenanthrene).
It is typically composed of seventeen carbon atoms, bonded in four fused
rings: three six-member cyclohexane rings (rings A, B and C in the first
illustration) and one five-member cyclopentane ring (the D ring).
Steroid Skeleton

46. Classification
• Steroids are chemically classified into the following:
1) Anabolic Steroids: They interact with androgen receptor, increase
muscle mass/athlete's performance and male sex hormones.
2) Glucocorticoids: They regulate metabolism and immune function,
and exhibit anti-inflammatory activity.
3) Mineralocorticoids: They maintain blood volume and renal
excretion. 4) Progestins: They are involved in the development of
female sex organs and characteristics.
5) Phytosteroids: They are plant steroids.
6) Ergosteroids: They are the steroids of fungi.

47. Uses
• Increase muscle mass.
• Athlete's performance.
• Develop Male sex hormones.
• Develop Female sex hormones.
• Regulate metabolism.
• Regulate Immune function.
• Anti-inflammatory activity.
• Use in treatment of asthma & Eczema.
• Use in treatment of Joint pain.
• Use in treatment of inflammatory bowel disease.

48. Cardiac glycosides
Cardiac glycosides are a class of organic compounds that increase the
output force of the heart and decrease its rate of contractions by
inhibiting the cellular sodium-potassium ATPase pump.
It is beneficial in medical uses as treatments for congestive heart failure
and cardiac arrhythmias.
Most commonly found as secondary metabolites in several plants such
as foxglove plants.

49. Structure of Cardiac Glycosides
• They have two parts like- Sugar part and non-sugar part.
• Sugar part is known as glycone, whereas non-sugar part is
known as aglycone or genin.
• Due to presence of aglycone part, glycosides give therapeutic
activities, while sugar portion is responsible for absorption.
• Sugar and non-sugar parts are linked with glycosidic bridge,
known as glycosidic linkage.
• This linkage is breaks by acid or enzyme hydrolysis and both
glycone and genin parts are separated.
• Glycone part is water soluble but insoluble in organic solvents
whereas aglycone parts are vice-versa.

50. There are two main types of cardiac glycosides.
1) Cardenolides.
2) Bufadienolides.
1) Cardenolides- These are derived from plant origin and
characterized by the presence of α,β-unsaturated five member
lactone ring at C-17 position of aglycone.
Ex- Digoxin, Digitoxin & Gitoxin.
2) Bufadienolides- These are derived from animal origin and
characterized by the presence of six member lactone ring with two
conjugated double bond at C-17 positions.
Ex- Squill (Scillaren).

52. Qualitative Analysis of Cardiac Glycosides

53. Cardiac glycoside uses
• Cardiac glycoside is most effective drug for the treatment of
CHF.
• Digitoxins are plant alkaloids.
• They increase myocardial contractions, which will increase
blood supply to all organs including the kidneys therefore
causing diuresis, which will decrease the edema.
• They are used to treat cardiac arrhythmia because they
decrease heart rate.
• It is used as a diuretics.
• It is use in elevating the cardiac output

54. Digitalis
Synonyms- Digitalis leaves, Foxglove leaves.
Biological Source- Digitalis consists of dried leaves of Digitalis
purpurea, family Scrophulariaceae, dried a temperature below
60°C, immediately after collecting the leaves.
Geographical Source- It is cultivated and collected in England,
other parts of Europe, United States and India.
Macroscopic Characters-
Colour- Dark greyish-green
Odour- Slight
Taste- Bitter
Size - 10 to 40 cm long and 4 to 20 cm wide

55. Chemical Constituents- Digitalis contain 0.2 to 0.45% of both
primary and secondary glycosides.
Primary glycosides- Purpurea glycosides A and B, Glucogetaloxin
Secondary glycosides- Digitoxin, Gitoxin and Getaloxin.
Primary glycosides are less stable and less significant than
secondary glycosides.
Purpurea glycosides A and B constitute the principle active
constituent of the fresh leaves.
Chemical Test For Digitalis
• Keller-Kiliani Test
• Legal Test
• Baljet Test

57. Storage Conditions- It should be store in well-closed containers,
keep on cool place and Protect from Light & Moisture.

58. Terpenes
• Terpenes is the generic name of a group of natural products,
structurally based isoprene (isopentenyl) units on (branched
five-carbon units).
• The term may also refer to oxygen derivatives of these
compounds that are known as "Terpenoids".

59. Classification of Terpenes

60. Triterpenoids are biosynthesized by mainly two pathways-
1- Mevalonate Pathways (Endoplasmic reticulum)
2- Pyruvate Pathways (In Plastids)

62. Difference b/w Terpenes and Terpenoids

64. Dioscorea
Synonyms- Yam, Chinese Yam, Rheumatism root.
Biological Source- It consists of dried tubers of the plants,
Dioscorea deltoidea, D. composita, and other species Dioscorea,
Family- Dioscoreaceae.
Geographical Source- It found in north western Himalayas, from
Kashmir and Punjab to Nepal and china upto an altitude of 1000-
3000 m.
Macroscopical Characters
• Colour- Slightly Brown.
• Odour- odourless
• Taste- Bitter

66. Liquorice
Synonyms- Mulethi, Liquorice Root.
Biological Source- It is obtained from the dried, unpeeled roots
and stolons of the plant Glycyrrhiza glabra.
Family- Leguminosae
Macroscopic characters
Odour - Faint and characteristic.
Colour - Yellowish brown
Taste- Sweet
Shape- Cylindrical
Size - 20-40cm in length and 2cm in diameter

67. Chemical Constituents
• Liquorice root contains Triterpenoids, Polyphenols, and
Polysaccharides.
• Flavonoids for the yellow root color.
• The principal glycoside, Glycyrrhizin, exists in content of 7% to
10%.
Glycyrrhizin

68. Chemical Test of Liquorice
• When Sulphuric acid (80% W/V) is added to a thick section of
the drug or powder, it instantly produced a deep Yellow colour.

69. Uses