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Anthracene (Anthraquinone)
Anthracene (Anthraquinone)
Glycosides
Glycosides
 Anthracene glycosides are oxygenated derivatives of pharmacological
Anthracene glycosides are oxygenated derivatives of pharmacological
importance that are used as laxatives or cathartics, anti-inflammatory,
importance that are used as laxatives or cathartics, anti-inflammatory,
antibacterial, antifungal and also as natural dyes.
antibacterial, antifungal and also as natural dyes.
 based on anthracene molecule
1
4
9
10
8
5
Anthraquinone
Reduction
Oxidation
Oxanthrone
Anthrone
O
O
O
OH
H
O
H
H
Oxidation
Anthranol
OH
tautomerization
Reduction
2
2
Anthranols and Anthrones
Anthranols and Anthrones
 Reduced anthraquinone derivatives.
Reduced anthraquinone derivatives.
 Occur either freely (aglycones) or as glycosides.
Occur either freely (aglycones) or as glycosides.
 Isome.
Isomers.
 Anthrone:
Anthrone: Parent structure (pale yellow, non-
Parent structure (pale yellow, non-
soluble in alkali, non-fluorescent)
soluble in alkali, non-fluorescent)
 Anthronol:
Anthronol: brown-yellow, soluble in alkali,
brown-yellow, soluble in alkali,
strongly fluorescent
strongly fluorescent
 Anthronol derivatives
Anthronol derivatives (e.g. in Aloe – have similar
(e.g. in Aloe – have similar
properties – fluorescence used for identification)
properties – fluorescence used for identification)
3
3
Oxanthrones
Oxanthrones
 Found in
Found in Cascara
Cascara bark
bark
 Intermediate products (between
Intermediate products (between
anthraquinones and anthranols)
anthraquinones and anthranols)
 When oxidised oxanthrones it form
When oxidised oxanthrones it form
anthraquinones
anthraquinones
 Oxanthrones are detected by
Oxanthrones are detected by Modified
Modified
Borntrager’s Test
Borntrager’s Test
(oxanthrones oxidised using hydrogen
(oxanthrones oxidised using hydrogen
peroxide)
peroxide)
oxanthrone
Dianthrones
Dianthrones
 Derived from 2 anthrone
Derived from 2 anthrone
molecules
molecules
 2 molecules may/not be
2 molecules may/not be
identical
identical
 Dianthrones are form easily
Dianthrones are form easily
due to mild oxidation of
due to mild oxidation of
anthrones
anthrones
 It form important
It form important
aglycones
aglycones
Cassia
Cassia
Rheum
Rheum
4
4
The activity decreases as oxidation level increase.
The activity decreases as oxidation level increase.
 Forms of Anthracene derivatives in Plants:
Forms of Anthracene derivatives in Plants:
 Aglycones:
Aglycones:
OH OH
CH3
HO
O
O
OH OH
CH2OH
O
O
OH OH
CH3
O
O
OH OH
COOH
O
O
Rhein
Chrysophanol
Emodin Aloe-emodin
 Dimeric Anthracene derivatives:
Dimeric Anthracene derivatives:
 They are derived from two anthracene unites connected by covalent
They are derived from two anthracene unites connected by covalent
C-C bond through C-10.
C-C bond through C-10.
 Homo-Dianthrones:
Homo-Dianthrones:
The two anthrone moieties are similar. e.g. Sennidins A&B and their
The two anthrone moieties are similar. e.g. Sennidins A&B and their
corresponding glycosides Sennosides A&B. They are all formed of
corresponding glycosides Sennosides A&B. They are all formed of
two Rhein monomers. The A group are (l)-form while the B group are
two Rhein monomers. The A group are (l)-form while the B group are
meso compounds with zero optical rotation.
meso compounds with zero optical rotation.
OR OH
COOH
O
OR
OH
HOOC
O
H
H
R= H Sennidin A
R= Glc Sennoside A
R= H Sennidin B
R= Glc Sennoside B
=
=
=
=
 Hetero-Dianthrones:
Hetero-Dianthrones:
The two anthrone moieties are different. e.g. Sennidins C&D and their
The two anthrone moieties are different. e.g. Sennidins C&D and their
corresponding glycosides Sennosides C&D. They are all formed of
corresponding glycosides Sennosides C&D. They are all formed of
one Rhein and one Aloe-emodin monomers. The C group are (l)-form
one Rhein and one Aloe-emodin monomers. The C group are (l)-form
while the D group are meso compounds with zero optical rotation.
while the D group are meso compounds with zero optical rotation.
OR OH
CH2OH
O
OR
OH
HOOC
O
H
H
R= H Sennidin C
R= Glc Sennoside C
R= H Sennidin D
R= Glc Sennoside D
=
=
=
=
 Glycosides:
Glycosides:
 O-glycosides:
O-glycosides:
e.g. Cascarosides A & B. They are both O- and C-glycosides. Each
e.g. Cascarosides A & B. They are both O- and C-glycosides. Each
one contain two sugar unites.
one contain two sugar unites.
 C-glycosides:
C-glycosides:
e.g. Barbaloin it is formed from the removal of one sugar from
e.g. Barbaloin it is formed from the removal of one sugar from
Cascarosides.
Cascarosides.
O OH
CH2OH
O
R
R1
Glc
R= Glc, R1= H Cascaroside A
R= H, R1= Glc Cascaroside B
OH OH
CH2OH
O
Glc
H
Structure-Activity Relationship:
Structure-Activity Relationship:
 Glycosylation is essential for activity.
Glycosylation is essential for activity.
 Hydroxylation at C-1 and C-8 is essential for activity.
Hydroxylation at C-1 and C-8 is essential for activity.
 Oxidation level at C-9 and C-10 is important:
Oxidation level at C-9 and C-10 is important:
 lowest
Highest level of oxidation (anthraquinones) have the lowest
activity.
activity.
 Oxanthrones are less active than anthrones.
Oxanthrones are less active than anthrones.
 Complete reduction of C-9 and C-10 eliminates the activity.
Complete reduction of C-9 and C-10 eliminates the activity.
 Substitution at C-3 have great impact on activity:
Substitution at C-3 have great impact on activity:
CH
CH2
2 OH > CH
OH > CH3
3 > COOH
> COOH
10
10
Introduction to Anthraquinones
Introduction to Anthraquinones
 Historically: Rhubarb, Senna, Aloes and
Historically: Rhubarb, Senna, Aloes and
Cascara were all used as purgative drugs.
Cascara were all used as purgative drugs.
 Monocotyledons:
Monocotyledons: Only Liliaceae.
Only Liliaceae.
Most commonly C-glycoside: barbaloin.
Most commonly C-glycoside: barbaloin.
 Dicotyledons:
Dicotyledons: Rubiaceae, Leguminosae,
Rubiaceae, Leguminosae,
Polygonaceae, Rhamnaceae, Ericaceae,
Polygonaceae, Rhamnaceae, Ericaceae,
Euphorbiaceae, Lythraceae, Saxifragaceae,
Euphorbiaceae, Lythraceae, Saxifragaceae,
Scrophulariaceae and Verbenacacea. Also in
Scrophulariaceae and Verbenacacea. Also in
certain fungi and lichen.
certain fungi and lichen.
11
11
Reduced derivatives
Reduced derivatives of anthraquinones
of anthraquinones
Oxanthrones, anthranols and anthrones
Oxanthrones, anthranols and anthrones
Compounds formed by the union of 2
Compounds formed by the union of 2
anthrone molecules
anthrone molecules
Dianthrones
Dianthrones
Aglycones:
Aglycones:
Chrysophanol/Chrysophanic acid
Chrysophanol/Chrysophanic acid 
 Rhubarb and
Rhubarb and
Senna.
Senna.
Rhein
Rhein 
 Rhubarb and Senna
Rhubarb and Senna
Aloe-emodin
Aloe-emodin 
 Rhubarb and Senna
Rhubarb and Senna
Emodin
Emodin 
 Rhubarb and Cascara
Rhubarb and Cascara
Senna - Leguminosae
Senna - Leguminosae
 1)
1) Consists of the dried
Consists of the dried
leaflets of
leaflets of Cassia
Cassia acutifolia
acutifolia
(Alexandrian senna)
(Alexandrian senna)
 2) ripe fruit (senna pod) of
2) ripe fruit (senna pod) of
Cassia acutifolia
Cassia acutifolia
 3) dried leaflets of
3) dried leaflets of Cassia
Cassia
angustifolia
angustifolia (Tinnevelly
(Tinnevelly
senna –indian senna).
senna –indian senna).
 Use:
Use: Laxative & purgative
Laxative & purgative
12
12
Alexandrian senna
Alexandrian senna
 Syn.
Syn.: Folia senna, Cassia senna,
: Folia senna, Cassia senna,
Egyptian senna, Nubian senna
Egyptian senna, Nubian senna
 B.S.:
B.S.: dried leaflets of
dried leaflets of Cassia acutifolia
Cassia acutifolia
Delile.
Delile.
 Family
Family: Leguminosae
: Leguminosae
 G.s.: Indigenous to Africa (tropical
G.s.: Indigenous to Africa (tropical
regions), Sudan, middle and nile
regions), Sudan, middle and nile
territories
territories
 Used since 9
Used since 9th
th
and 10
and 10th
th
century
century
 Itroduced into medicine by Arab
Itroduced into medicine by Arab
physicians (used both the leaves and
physicians (used both the leaves and
pods)
pods)
 Exported by Alexandria – name of the
Exported by Alexandria – name of the
Sudanese drug.
Sudanese drug.
13
13
Morphology
Morphology
 Color:
Color: pale grayish green
pale grayish green
 Odour:
Odour: Slight & characteristic
Slight & characteristic
 Taste:
Taste: Slight bitter & mucilagenous
Slight bitter & mucilagenous
 Shape:
Shape: Ovate lanceolate, entire margin, uneven base, acute
Ovate lanceolate, entire margin, uneven base, acute
apex, lamina pubesent.
apex, lamina pubesent.
 Size:
Size: 20mm-40mm long & 7mm-12mm wide.
20mm-40mm long & 7mm-12mm wide.
Cultivation & collection
Cultivation & collection
 It is small shrub up to 2 mt. height.
It is small shrub up to 2 mt. height.
 Obtained from cultivated & wild zone.
Obtained from cultivated & wild zone.
 Collected in
Collected in September
September
 Whole branches bearing leaves are dried in the
Whole branches bearing leaves are dried in the
sun.
sun.
 Pods and large stalks are separated with
Pods and large stalks are separated with
sieves.
sieves.
 Leaves are graded (whole leaves and half-leave
Leaves are graded (whole leaves and half-leave
mix, siftings).
mix, siftings).
 Whole leaves – sold to public
Whole leaves – sold to public
 Rest – used for galenicals (herbal remidies).
Rest – used for galenicals (herbal remidies).
15
15
16
16
Senna – chemical Constituents
Senna – chemical Constituents
 Senna consist four types of glycosides
Senna consist four types of glycosides:
:
Sennoside A
Sennoside A
Sennoside B
Sennoside B
Sennoside C
Sennoside C
Sennoside D
Sennoside D
In their active costituents are sennoside A, sennosides B
In their active costituents are sennoside A, sennosides B
 Upon hydrolysis of sennosides it gives two molecules
Upon hydrolysis of sennosides it gives two molecules
glucose+aglycones: Sennidin A and Sennidin B.
glucose+aglycones: Sennidin A and Sennidin B. Rhein
Rhein
8-glucosides, Rhein 8-diglucosides
8-glucosides, Rhein 8-diglucosides
 Aloe-emodin
Aloe-emodin
 Crysophenic acid, myricyl alcohol, resin
Crysophenic acid, myricyl alcohol, resin
 Tinnevellin glycoside(indian senna), 6-hydroxy mucizin
Tinnevellin glycoside(indian senna), 6-hydroxy mucizin
glucoside
glucoside
Chemical constituents:
Chemical constituents:
(i) 1 and 1,8 ‘O’ glucosides
(i) 1 and 1,8 ‘O’ glucosides
= 1
= 1st
st
series glycosides
series glycosides
aglycones: rhein, aloe emodin
aglycones: rhein, aloe emodin
(ii) dimeric dianthrones
(ii) dimeric dianthrones
= 2
= 2nd
nd
series
series
reduced products
reduced products
dimer can be split into two parts with FeCl3
hydrolysis and monomer aglycones assayed for
Indian Senna
Indian Senna
 Syn.
Syn.: Cassia leaf, Sonmukhi, senai-ki-patti, bhumiari
: Cassia leaf, Sonmukhi, senai-ki-patti, bhumiari
 B.S.:
B.S.: dried leaflets of Cassia angustifolia Vahl.
 Family
Family: Leguminosae
: Leguminosae
 G.S.:
G.S.: South India, Tinneveley & Ramanathpurum district,
South India, Tinneveley & Ramanathpurum district,
Pakistan
Pakistan
 Morphology:
Morphology:
Color: yellowish green
Odour: Slight & characteristic
Taste: Bitter & mucilagenous
Shape: lanceolate to ovate lanceolate,
entire margin, uneven base, acute apex,
lamina pubesent.
Size: 2.5 cm-6 cm long & 5mm-8mm wide.
Cultivation & collection
Cultivation & collection
 It is small shrub up to 1-1.5 mt. height. Twice a year & after
It is small shrub up to 1-1.5 mt. height. Twice a year & after
paddy crops.
paddy crops.
 Soil required is sandy loamy, coarse gravelly, loamy soil
Soil required is sandy loamy, coarse gravelly, loamy soil
which well ploughed, leveled & semi-irrigated.
which well ploughed, leveled & semi-irrigated.
 Seeds sawn in
Seeds sawn in October & February
October & February. Within
. Within 2-3 months
2-3 months plant
plant
are ready for
are ready for collection
collection.
.
 Leaflets are collected by hand before flowring. Dried in shade
Leaflets are collected by hand before flowring. Dried in shade
to maintain natural green color.
to maintain natural green color.
 1
1st
st
stage: leaflet are greenish in color & thick
stage: leaflet are greenish in color & thick
 2
2nd
nd
stage: harvesting is done after 30 days of 1
stage: harvesting is done after 30 days of 1st
st
stage
stage
 3
3rd
rd
stage: plant are uprooted
stage: plant are uprooted
 Packing:
Packing: in bales with pressure that cause oblique impressions
in bales with pressure that cause oblique impressions
in leaves. it remain less brittle and in good condition.
in leaves. it remain less brittle and in good condition.
 Fresh:
Fresh: anthron, dried at 20-50◦ - dianthron, above 50◦ -
anthron, dried at 20-50◦ - dianthron, above 50◦ -
anthraquinone
anthraquinone
19
19
20
20
Comparison of
Comparison of
Alexandrian and Tinnevelly Senna
Alexandrian and Tinnevelly Senna
 Macroscopical
Macroscopical
 larger than 4 cm in
larger than 4 cm in
length
length
 Grey-green
Grey-green
 Asymmetric at base
Asymmetric at base
 Broken and curled at
Broken and curled at
edges
edges
 Few press markings
Few press markings
 Macroscopical
Macroscopical
 exceeds 5cm in length
exceeds 5cm in length
 Yellow-green
Yellow-green
 Less asymmetric at
Less asymmetric at
base
base
 broken and normally
broken and normally
flat
flat
 Often shows
Often shows
impressions (mid vein)
impressions (mid vein)
21
21
Comparison between
Comparison between
Alexandrian and Tinnevelly Senna
Alexandrian and Tinnevelly Senna
 Microscopical
Microscopical
 Hairs – numerous
Hairs – numerous
(approximately three
(approximately three
epidermal cells apart)
epidermal cells apart)
 Most stomata have
Most stomata have
two subsidiary cells
two subsidiary cells
 Microscopical
Microscopical
 Hairs less numerous
Hairs less numerous
(approximately six
(approximately six
epidermal cells apart)
epidermal cells apart)
 Stomata have 2-3
Stomata have 2-3
subsidiary cells with
subsidiary cells with
the respective ratio 7:3
the respective ratio 7:3
22
22
Comparison between
Comparison between
Alexandrian and Tinnevelly Senna
Alexandrian and Tinnevelly Senna
 Chemical Tests
Chemical Tests
 Ether extract of
Ether extract of
hydrolysed acid
hydrolysed acid
solution of herb with
solution of herb with
methanolic
methanolic
magnesioum acetate
magnesioum acetate
solution gives
solution gives
 Pink colour in
Pink colour in
daylight
daylight
 Pale green-orange
Pale green-orange
colour in filtered UV
colour in filtered UV
light
light
TLC
TLC
 Hydroxymusizin
Hydroxymusizin
 Chemical Tests
Chemical Tests
Same Test
Same Test
Orange colour in
Orange colour in
daylight
daylight
Yellow-green colour
Yellow-green colour
in filtered UV light
in filtered UV light
TLC
TLC
 Tinnevellin glycoside
Tinnevellin glycoside
23
23
Senna – Allied Drugs &
Senna – Allied Drugs & Substitutes
Substitutes
1.
1. Bombay, Mecca and Arabian Sennas (found in
Bombay, Mecca and Arabian Sennas (found in Cassia
Cassia
angustifolia
angustifolia from Arabia).
from Arabia).
2.
2. Palthe senna(
Palthe senna( Cassia Auriculata)
Cassia Auriculata)
3.
3. Dog senna –
Dog senna – Cassia obovata
Cassia obovata
4.
4. Cassia podocarpa
Cassia podocarpa
5.
5. Argel leaves – Solenostemma argel
Argel leaves – Solenostemma argel
6.
6. Coriario myrtifolia
Coriario myrtifolia
24
24
Senna Fruit
Senna Fruit
 Definition:
Definition: Senna
Senna
pods
pods are the dried,
are the dried,
ripe fruits of
ripe fruits of Cassia
Cassia
senna
senna and
and Cassia
Cassia
angustifolia
angustifolia, which
, which
are commercially
are commercially
known as Alexandrian
known as Alexandrian
and Tinnevelly senna
and Tinnevelly senna
pods respectively.
pods respectively.
Both have separate
Both have separate
monographs
monographs
25
25
Senna Fruit - Collection
Senna Fruit - Collection
 Pods are collected with
Pods are collected with
the leaves and dried in
the leaves and dried in
a similar fashion.
a similar fashion.
 After separation of the
After separation of the
leaves, the pods are
leaves, the pods are
hand-picked into
hand-picked into
various qualities, the
various qualities, the
finer being sold
finer being sold
(commercially), while
(commercially), while
the finer pieces are
the finer pieces are
used to make
used to make
galenicals.
galenicals.
26
26
Senna Fruit - Constituents
Senna Fruit - Constituents
 Active constituents
Active constituents
are found in the
are found in the
pericarp.
pericarp.
 Similar to those
Similar to those
actives of the leaves
actives of the leaves
 Sennoside A
Sennoside A
 Sennidin
Sennidin
27
27
Senna – Additional uses
Senna – Additional uses
 Medicinal Actions
Medicinal Actions
 Vermifuge, diuretic,
Vermifuge, diuretic,
febrifuge
febrifuge
 Other uses:
Other uses: laxative
laxative
candy (bitter taste).
candy (bitter taste).
 Also used to treat
Also used to treat
flatulence, gout, fever.
flatulence, gout, fever.
 Topically:
Topically: poultice
poultice
prepared with vinegar to
prepared with vinegar to
treat pimples.
treat pimples.
 NOTE: Senna may
NOTE: Senna may
cause urine to become
cause urine to become
reddish – no clinical
reddish – no clinical
significance
significance.
.
Contra-indications
Contra-indications
 Gout, colitis, GI
Gout, colitis, GI
inflammation.
inflammation.
 Should not be used with
Should not be used with cardiac
cardiac
glycosides.
glycosides.
 Seeds/pods
Seeds/pods give gentler action
give gentler action
than leaves: more appropriate for
than leaves: more appropriate for
the young, elderly and those
the young, elderly and those
prone to stomach cramps.
prone to stomach cramps.
 NB:
NB: Over-use causes
Over-use causes
dependency.
dependency.
 Overdose: nausea, bloody
Overdose: nausea, bloody
diarrhoea, vomiting and nephritis.
diarrhoea, vomiting and nephritis.
 Long-term use: dehydration &
Long-term use: dehydration &
electrolyte depletion, worsening
electrolyte depletion, worsening
constipation and weakening
constipation and weakening
intestinal muscles.
intestinal muscles.
28
28
Some Drugs containing Anthracene derivatives:
Some Drugs containing Anthracene derivatives:
Senna
Senna:
:
 Leaves and pods contain Sennosides A-D.
Leaves and pods contain Sennosides A-D.
 The C-C bond protect the anthrone from oxidation.
The C-C bond protect the anthrone from oxidation.
Chemical test:
Chemical test:
Borntrager’s and Modified Borntrager’s test:
Borntrager’s and Modified Borntrager’s test:
 For Aglycones:
For Aglycones:
 Extract plant material with organic solvent.
Extract plant material with organic solvent.
 Shake with NH
Shake with NH4
4 OH OR KOH.
OH OR KOH.
 For O-Glycosides:
For O-Glycosides:
 Boil plant material with dil. HCl for 10 min, filter and shake with
Boil plant material with dil. HCl for 10 min, filter and shake with
organic solvent (Ether or Benzene).
organic solvent (Ether or Benzene).
 Separate the organic solvent.
Separate the organic solvent.
 Shake with NH
Shake with NH4
4 OH OR KOH.
OH OR KOH.
 For C-Glycosides:
For C-Glycosides:
 Boil plant material with dil. HCl/FeCl
Boil plant material with dil. HCl/FeCl3
3 , filter and shake with
, filter and shake with
organic solvent (Ether or Benzene).
organic solvent (Ether or Benzene).
 Separate the organic solvent.
Separate the organic solvent.
 Shake with NH
Shake with NH4
4 OH OR KOH.
OH OR KOH.
 Positive result indicated by
Positive result indicated by Rose Red colour
Rose Red colour in
in
the aqueous alkaline layer.
the aqueous alkaline layer.
Cascara
Cascara
 Syn: Sacred bark, cortex rhamni, Californian buckthron, cascara
Syn: Sacred bark, cortex rhamni, Californian buckthron, cascara
sagrada
sagrada
 B.S.;
B.S.; Rhamnus pershiana
Rhamnus pershiana
 Family:
Family: Rhamnaceae
Rhamnaceae
 G.S.: N.Colifornia, columbia, canada, Kenya
G.S.: N.Colifornia, columbia, canada, Kenya
 Morphology:
Morphology:
 Color: outer surface: dark purple to brown (lichens & moss)
Color: outer surface: dark purple to brown (lichens & moss)
 Inner surface: yellow to reddish brown
Inner surface: yellow to reddish brown
 Odour: cherecterictic
Odour: cherecterictic
 Taste: bitter
Taste: bitter
 Shape: Single squill, curved or channel
Shape: Single squill, curved or channel
 Size: 5-20 cm long, 2-3 cm wide, 1.2-4 mm thick
Size: 5-20 cm long, 2-3 cm wide, 1.2-4 mm thick
 C&C: Cascaroside A,B,C,D
C&C: Cascaroside A,B,C,D
 Use: bark extract
Use: bark extract
 collected, dried and stored for 12 months (↓ anthraquinone
collected, dried and stored for 12 months (↓ anthraquinone
content -> less toxic)
content -> less toxic)
 more violent purgative
more violent purgative
 griping action
griping action
 harder to eliminate
harder to eliminate
 Use
Use: night before to clear bowels for x-rays.
: night before to clear bowels for x-rays.
 Larg dose use as cathartic.
Larg dose use as cathartic.
Chemical constituents:
Chemical constituents:
(i) 4 primary glycosides
(i) 4 primary glycosides
 O- and C- linkages
O- and C- linkages
(ii) C-glycosides - two aloins
(ii) C-glycosides - two aloins
 barbaloin – derived from aloe-emodin
barbaloin – derived from aloe-emodin
 chrysaloin – derived from chrysophanol
chrysaloin – derived from chrysophanol
(iii) a number of O-glycosides
(iii) a number of O-glycosides
 derived from emodin oxanthrone, aloe-emodin, chrysophanol
derived from emodin oxanthrone, aloe-emodin, chrysophanol
(iv) various dianthrones
(iv) various dianthrones
 incl. emodin, aloe-emodin, chrysophanol, herterodianthrones palmidin A
incl. emodin, aloe-emodin, chrysophanol, herterodianthrones palmidin A
B C
B C
(v) aloe-emodin, chrysophanol, emodin in free state
(v) aloe-emodin, chrysophanol, emodin in free state
To get aglycones FeCl3
To get aloins oxidise with acid
Rhubarb
Rhubarb
 Syn.: Rheum, Radix rhei, da huang
Syn.: Rheum, Radix rhei, da huang
 B.S.: Peeled & dried rhizomes , root of
B.S.: Peeled & dried rhizomes , root of Rheum officinale
Rheum officinale
Bail.,
Bail., R.palmetum L
R.palmetum L.,
., R.rhaponticum
R.rhaponticum Willd (chinese)
Willd (chinese)
R.emodi
R.emodi Wall.,
Wall., R. webbianum
R. webbianum Royale (Indian)
Royale (Indian)
 Family: Polygonaceae
Family: Polygonaceae
 G.S.: Tibet to south east china, germany, south europe,
G.S.: Tibet to south east china, germany, south europe,
kashmir, kullu, Sikkim, UP, panjab, nepal
kashmir, kullu, Sikkim, UP, panjab, nepal
Morphology
Morphology
 Color:
Color: fresh surface after cut pink to dull grey in day
fresh surface after cut pink to dull grey in day
light & reddish brown U
light & reddish brown UV
V
 Odour:
Odour: Characteristics
Characteristics
 Taste:
Taste: Bitter, gritty, astringent
Bitter, gritty, astringent
 Size:
Size: 8-10 cm in length, 3-4 cm thick
8-10 cm in length, 3-4 cm thick
 C.C.
C.C.:
: rhein, glucorhein, emodin, aloe emodin and
rhein, glucorhein, emodin, aloe emodin and
chrysophenol
chrysophenol
 Palmidin A, B, C
Palmidin A, B, C
 Rheinoside A,B,C,D
Rheinoside A,B,C,D
USE
USE
 Bitter, stomachic, laxative, purgative, diarrhoea,
Bitter, stomachic, laxative, purgative, diarrhoea,
eczema, psoriasis
eczema, psoriasis
 ADULTRANTS
ADULTRANTS
 Rheum rhaponticum,
Rheum rhaponticum,
 R. undulatum
R. undulatum
 R.copactum
R.copactum
 Japanese rhubarb
Japanese rhubarb
ALOE
ALOE
 Syn.: Kumari, musabar, korphad, Gheekunwar, Ghrit
Syn.: Kumari, musabar, korphad, Gheekunwar, Ghrit
kumara
kumara
 B.S.: dried juce of leaves of
B.S.: dried juce of leaves of Aloe barbadensis
Aloe barbadensis Miller(
Miller(
Curacao Aloe),
Curacao Aloe), Aloe perryi
Aloe perryi Baker (Socotrine aloe),
Baker (Socotrine aloe),
Aloe ferox
Aloe ferox Miller.,
Miller., Aloe spicata
Aloe spicata Baker (Cape Aloe)
Baker (Cape Aloe)
 Family: Liliaceae
Family: Liliaceae
 G.S.: Estern & southern Africa, west Indies, India,
G.S.: Estern & southern Africa, west Indies, India,
western region.
western region.
Aloe perryi, barbadensis, ferox
Aloe perryi, barbadensis, ferox
Cultivation
Cultivation
 Sandy, lomy, well drained soil.
Sandy, lomy, well drained soil.
 Acidic, Basic, Neutral.
Acidic, Basic, Neutral.
 Grow in dry climate condition. It is xerophytic plant.
Grow in dry climate condition. It is xerophytic plant.
 Propagated by seed, sawn in spring, germinate in 1-6
Propagated by seed, sawn in spring, germinate in 1-6
mnths at 16 degree C. then transferred in pot.
mnths at 16 degree C. then transferred in pot.
 Offsets & suckers are available in spring.
Offsets & suckers are available in spring.
 Suckers planted in raw 50 cm in rainy season.
Suckers planted in raw 50 cm in rainy season.
 2
2nd
nd
year harvesting is started upto next 12 year.
year harvesting is started upto next 12 year.
 After that plant are uprooted.
After that plant are uprooted.
 Aloitic juice collected after cutting leaves.
Aloitic juice collected after cutting leaves.
Aloe - Liliaceae
Aloe - Liliaceae
 Definition:
Definition: Aloes are the
Aloes are the
solid residue obtained by
solid residue obtained by
evaporating the liquid which
evaporating the liquid which
drains from the transversely
drains from the transversely
cut leaves of various
cut leaves of various Aloe
Aloe
species.
species.
 The juice is usually
The juice is usually
concentrated by boiling and
concentrated by boiling and
solidifies on cooling.
solidifies on cooling.
 Official varieties are the
Official varieties are the
Cape Aloes from SA and
Cape Aloes from SA and
Kenya (
Kenya (Aloe ferox
Aloe ferox), and the
), and the
Curacao Aloes from West
Curacao Aloes from West
Indies (
Indies (Aloe barbadensis
Aloe barbadensis).
).
40
40
41
41
Preparation of Cape Aloes
Preparation of Cape Aloes
 Cape Aloes are prepared from the wild plants
Cape Aloes are prepared from the wild plants of Aloe
of Aloe
ferox
ferox.
.
 Leaves are cut transversely near the base.
Leaves are cut transversely near the base.
 Two hundred leaves arranged around a shallow hole in
Two hundred leaves arranged around a shallow hole in
the ground (lined with canvas or goatskin).
the ground (lined with canvas or goatskin).
 Cut ends overlap & drain into the canvas.
Cut ends overlap & drain into the canvas.
After 6hrs all the juice is collected.
After 6hrs all the juice is collected.
 Transferred to a drum.
Transferred to a drum.
 Boiled for 4hrs on an open fire.
Boiled for 4hrs on an open fire.
 Poured into tins while hot
Poured into tins while hot 
 solidifies.
solidifies.
Preparation of Cape Aloes
Preparation of Cape Aloes
42
42
Cape Aloes - Characteristics
Cape Aloes - Characteristics
 Dark brown or Green-
Dark brown or Green-
brown
brown
 Glassy masses
Glassy masses
 Thin fragments have
Thin fragments have
a deep olive colour
a deep olive colour
Semi-transparent.
Semi-transparent.
43
43
Cape Aloes - Characteristics
Cape Aloes - Characteristics
 Powder: green-yellow
Powder: green-yellow
 When rubbed two pieces
When rubbed two pieces
of drug together – powder is
of drug together – powder is
found on the surfaces.
found on the surfaces.
 Characteristic sour odour
Characteristic sour odour
(rhubarb/apple-tart odour).
(rhubarb/apple-tart odour).
 Taste: nauseous and bitter.
Taste: nauseous and bitter.
 Microscopy: powder in
Microscopy: powder in
lactophenol – amorphous.
lactophenol – amorphous.
44
44
Characteristics of Curacao Aloes
Characteristics of Curacao Aloes
 Colour: yellow-brown – chocolate brown.
Colour: yellow-brown – chocolate brown.
 Cut at base, V shaped container of wood 1-2 m long with
Cut at base, V shaped container of wood 1-2 m long with
cut surface towards container.
cut surface towards container.
 Poor qualities (overheated) black colour.
Poor qualities (overheated) black colour.
 Opaque
Opaque
 Breaks with a waxy facture
Breaks with a waxy facture
 Semi-transparent
Semi-transparent
 More opaque on keeping.
More opaque on keeping.
 Nauseous and bitter taste.
Nauseous and bitter taste.
 Thick hot juice taken completely in copper(metal) pan till it
Thick hot juice taken completely in copper(metal) pan till it
become thick (hard)
become thick (hard)
45
45
Socotrine aloe
Socotrine aloe
 Juice collected on goat skin and allow to dry for long
Juice collected on goat skin and allow to dry for long
time without heating or boliling.
time without heating or boliling.
 It forms viscous pasty mass which is filled in
It forms viscous pasty mass which is filled in
container of wood.
container of wood.
 Zinzibar aloe
Zinzibar aloe
 Same as above
Same as above
 Also called monkey skin aloe.
Also called monkey skin aloe.
Aloes - Constituents
Aloes - Constituents
 C-glycosides
C-glycosides
 Resins
Resins
 Glycosides
Glycosides
 Aloin
Aloin
 Barbaloin
Barbaloin
 Isobarbaloin
Isobarbaloin
 Aloe-emodin
Aloe-emodin
Cape Aloes:
Cape Aloes: Also Contain
Also Contain
Aloinoside A
Aloinoside A &
& Aloinoside B
Aloinoside B
(O-glycosides of
(O-glycosides of
barbaloin)
barbaloin)
47
47
48
48
Aloe
Aloe - Constituents
- Constituents
Aloe Constituents & Chemical
Aloe Constituents & Chemical
Tests:
Tests:
 Unlike C-glycosides, O-glycosides
Unlike C-glycosides, O-glycosides
of
of Aloe
Aloe are not hydrolysed by
are not hydrolysed by
heating with dilute acids or alkali.
heating with dilute acids or alkali.
 Can be decomposed with ferric
Can be decomposed with ferric
chloride & dilute HCl -
chloride & dilute HCl - NB
NB:
: Modified
Modified
Borntrager’s Test
Borntrager’s Test – oxidative
– oxidative
hydrolysis. Anthraquinones give a
hydrolysis. Anthraquinones give a
red
red colour when shaken with dilute
colour when shaken with dilute
ammonia.
ammonia.
 NB:
NB: All Aloes give a strong
All Aloes give a strong green
green
fluorescence
fluorescence with borax
with borax
(characteristic of anthranols) -
(characteristic of anthranols) -
General test for aloes.
General test for aloes.
49
49
Aloe
Aloe - Uses
- Uses
 Purgative, abortification,
Purgative, abortification,
emolient, stomachic,
emolient, stomachic,
stimulant & tonic.
stimulant & tonic.
 Used in solar, tharmal,
Used in solar, tharmal,
radiation burns, in skin
radiation burns, in skin
irritation
irritation
 Cosmetic
Cosmetic
50
50
Aloe – Additional uses
Aloe – Additional uses
 Medicinal Uses:
Medicinal Uses:
 Anti-bacterial, anti-fungal,
Anti-bacterial, anti-fungal,
chologoge, emmenogogue,
chologoge, emmenogogue,
anti-inflammatory (juice),
anti-inflammatory (juice),
anti-inflammatory ,
anti-inflammatory ,
demulcent, vulnerary,
demulcent, vulnerary,
immune-stimulating (gel).
immune-stimulating (gel).
Radiation burns
Radiation burns (internal and
(internal and
external use)
external use)
 Contra-indications
Contra-indications
Pregnancy & lactation
Pregnancy & lactation
(internal uses)
(internal uses)
 Etymology
Etymology
 Name derives from Arabic
Name derives from Arabic
alu,
alu, meaning shiny or bitter
meaning shiny or bitter
in reference to the gel.
in reference to the gel.
 Other uses
Other uses
 Khoi-San hunters rub gel
Khoi-San hunters rub gel
on their bodies to reduce
on their bodies to reduce
sweating and mask their
sweating and mask their
scent.
scent.
 Used to break nail-biting
Used to break nail-biting
habit.
habit.
51
51
Aloe vera Products
Aloe vera Products
 These are derived from
These are derived from
the mucilage gel –
the mucilage gel –
parenchyma cells
parenchyma cells
 Should not be confused
Should not be confused
with aloes (juice of
with aloes (juice of
pericycle – juice used for
pericycle – juice used for
laxative effect).
laxative effect).
 Cosmetic industry
Cosmetic industry
(usefulness often
(usefulness often
exaggerated) - Used as
exaggerated) - Used as
suntan lotions, tonics and
suntan lotions, tonics and
food additives.
food additives.
 Mucilage =
Mucilage =
polysaccharide of
polysaccharide of
glucomannans and pectin
glucomannans and pectin
52
52

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Anthra quinone glycosides part 1

  • 1. Anthracene (Anthraquinone) Anthracene (Anthraquinone) Glycosides Glycosides  Anthracene glycosides are oxygenated derivatives of pharmacological Anthracene glycosides are oxygenated derivatives of pharmacological importance that are used as laxatives or cathartics, anti-inflammatory, importance that are used as laxatives or cathartics, anti-inflammatory, antibacterial, antifungal and also as natural dyes. antibacterial, antifungal and also as natural dyes.  based on anthracene molecule 1 4 9 10 8 5 Anthraquinone Reduction Oxidation Oxanthrone Anthrone O O O OH H O H H Oxidation Anthranol OH tautomerization Reduction
  • 2. 2 2 Anthranols and Anthrones Anthranols and Anthrones  Reduced anthraquinone derivatives. Reduced anthraquinone derivatives.  Occur either freely (aglycones) or as glycosides. Occur either freely (aglycones) or as glycosides.  Isome. Isomers.  Anthrone: Anthrone: Parent structure (pale yellow, non- Parent structure (pale yellow, non- soluble in alkali, non-fluorescent) soluble in alkali, non-fluorescent)  Anthronol: Anthronol: brown-yellow, soluble in alkali, brown-yellow, soluble in alkali, strongly fluorescent strongly fluorescent  Anthronol derivatives Anthronol derivatives (e.g. in Aloe – have similar (e.g. in Aloe – have similar properties – fluorescence used for identification) properties – fluorescence used for identification)
  • 3. 3 3 Oxanthrones Oxanthrones  Found in Found in Cascara Cascara bark bark  Intermediate products (between Intermediate products (between anthraquinones and anthranols) anthraquinones and anthranols)  When oxidised oxanthrones it form When oxidised oxanthrones it form anthraquinones anthraquinones  Oxanthrones are detected by Oxanthrones are detected by Modified Modified Borntrager’s Test Borntrager’s Test (oxanthrones oxidised using hydrogen (oxanthrones oxidised using hydrogen peroxide) peroxide) oxanthrone
  • 4. Dianthrones Dianthrones  Derived from 2 anthrone Derived from 2 anthrone molecules molecules  2 molecules may/not be 2 molecules may/not be identical identical  Dianthrones are form easily Dianthrones are form easily due to mild oxidation of due to mild oxidation of anthrones anthrones  It form important It form important aglycones aglycones Cassia Cassia Rheum Rheum 4 4
  • 5. The activity decreases as oxidation level increase. The activity decreases as oxidation level increase.  Forms of Anthracene derivatives in Plants: Forms of Anthracene derivatives in Plants:  Aglycones: Aglycones: OH OH CH3 HO O O OH OH CH2OH O O OH OH CH3 O O OH OH COOH O O Rhein Chrysophanol Emodin Aloe-emodin
  • 6.  Dimeric Anthracene derivatives: Dimeric Anthracene derivatives:  They are derived from two anthracene unites connected by covalent They are derived from two anthracene unites connected by covalent C-C bond through C-10. C-C bond through C-10.  Homo-Dianthrones: Homo-Dianthrones: The two anthrone moieties are similar. e.g. Sennidins A&B and their The two anthrone moieties are similar. e.g. Sennidins A&B and their corresponding glycosides Sennosides A&B. They are all formed of corresponding glycosides Sennosides A&B. They are all formed of two Rhein monomers. The A group are (l)-form while the B group are two Rhein monomers. The A group are (l)-form while the B group are meso compounds with zero optical rotation. meso compounds with zero optical rotation. OR OH COOH O OR OH HOOC O H H R= H Sennidin A R= Glc Sennoside A R= H Sennidin B R= Glc Sennoside B = = = =
  • 7.  Hetero-Dianthrones: Hetero-Dianthrones: The two anthrone moieties are different. e.g. Sennidins C&D and their The two anthrone moieties are different. e.g. Sennidins C&D and their corresponding glycosides Sennosides C&D. They are all formed of corresponding glycosides Sennosides C&D. They are all formed of one Rhein and one Aloe-emodin monomers. The C group are (l)-form one Rhein and one Aloe-emodin monomers. The C group are (l)-form while the D group are meso compounds with zero optical rotation. while the D group are meso compounds with zero optical rotation. OR OH CH2OH O OR OH HOOC O H H R= H Sennidin C R= Glc Sennoside C R= H Sennidin D R= Glc Sennoside D = = = =
  • 8.  Glycosides: Glycosides:  O-glycosides: O-glycosides: e.g. Cascarosides A & B. They are both O- and C-glycosides. Each e.g. Cascarosides A & B. They are both O- and C-glycosides. Each one contain two sugar unites. one contain two sugar unites.  C-glycosides: C-glycosides: e.g. Barbaloin it is formed from the removal of one sugar from e.g. Barbaloin it is formed from the removal of one sugar from Cascarosides. Cascarosides. O OH CH2OH O R R1 Glc R= Glc, R1= H Cascaroside A R= H, R1= Glc Cascaroside B OH OH CH2OH O Glc H
  • 9. Structure-Activity Relationship: Structure-Activity Relationship:  Glycosylation is essential for activity. Glycosylation is essential for activity.  Hydroxylation at C-1 and C-8 is essential for activity. Hydroxylation at C-1 and C-8 is essential for activity.  Oxidation level at C-9 and C-10 is important: Oxidation level at C-9 and C-10 is important:  lowest Highest level of oxidation (anthraquinones) have the lowest activity. activity.  Oxanthrones are less active than anthrones. Oxanthrones are less active than anthrones.  Complete reduction of C-9 and C-10 eliminates the activity. Complete reduction of C-9 and C-10 eliminates the activity.  Substitution at C-3 have great impact on activity: Substitution at C-3 have great impact on activity: CH CH2 2 OH > CH OH > CH3 3 > COOH > COOH
  • 10. 10 10 Introduction to Anthraquinones Introduction to Anthraquinones  Historically: Rhubarb, Senna, Aloes and Historically: Rhubarb, Senna, Aloes and Cascara were all used as purgative drugs. Cascara were all used as purgative drugs.  Monocotyledons: Monocotyledons: Only Liliaceae. Only Liliaceae. Most commonly C-glycoside: barbaloin. Most commonly C-glycoside: barbaloin.  Dicotyledons: Dicotyledons: Rubiaceae, Leguminosae, Rubiaceae, Leguminosae, Polygonaceae, Rhamnaceae, Ericaceae, Polygonaceae, Rhamnaceae, Ericaceae, Euphorbiaceae, Lythraceae, Saxifragaceae, Euphorbiaceae, Lythraceae, Saxifragaceae, Scrophulariaceae and Verbenacacea. Also in Scrophulariaceae and Verbenacacea. Also in certain fungi and lichen. certain fungi and lichen.
  • 11. 11 11 Reduced derivatives Reduced derivatives of anthraquinones of anthraquinones Oxanthrones, anthranols and anthrones Oxanthrones, anthranols and anthrones Compounds formed by the union of 2 Compounds formed by the union of 2 anthrone molecules anthrone molecules Dianthrones Dianthrones Aglycones: Aglycones: Chrysophanol/Chrysophanic acid Chrysophanol/Chrysophanic acid   Rhubarb and Rhubarb and Senna. Senna. Rhein Rhein   Rhubarb and Senna Rhubarb and Senna Aloe-emodin Aloe-emodin   Rhubarb and Senna Rhubarb and Senna Emodin Emodin   Rhubarb and Cascara Rhubarb and Cascara
  • 12. Senna - Leguminosae Senna - Leguminosae  1) 1) Consists of the dried Consists of the dried leaflets of leaflets of Cassia Cassia acutifolia acutifolia (Alexandrian senna) (Alexandrian senna)  2) ripe fruit (senna pod) of 2) ripe fruit (senna pod) of Cassia acutifolia Cassia acutifolia  3) dried leaflets of 3) dried leaflets of Cassia Cassia angustifolia angustifolia (Tinnevelly (Tinnevelly senna –indian senna). senna –indian senna).  Use: Use: Laxative & purgative Laxative & purgative 12 12
  • 13. Alexandrian senna Alexandrian senna  Syn. Syn.: Folia senna, Cassia senna, : Folia senna, Cassia senna, Egyptian senna, Nubian senna Egyptian senna, Nubian senna  B.S.: B.S.: dried leaflets of dried leaflets of Cassia acutifolia Cassia acutifolia Delile. Delile.  Family Family: Leguminosae : Leguminosae  G.s.: Indigenous to Africa (tropical G.s.: Indigenous to Africa (tropical regions), Sudan, middle and nile regions), Sudan, middle and nile territories territories  Used since 9 Used since 9th th and 10 and 10th th century century  Itroduced into medicine by Arab Itroduced into medicine by Arab physicians (used both the leaves and physicians (used both the leaves and pods) pods)  Exported by Alexandria – name of the Exported by Alexandria – name of the Sudanese drug. Sudanese drug. 13 13
  • 14. Morphology Morphology  Color: Color: pale grayish green pale grayish green  Odour: Odour: Slight & characteristic Slight & characteristic  Taste: Taste: Slight bitter & mucilagenous Slight bitter & mucilagenous  Shape: Shape: Ovate lanceolate, entire margin, uneven base, acute Ovate lanceolate, entire margin, uneven base, acute apex, lamina pubesent. apex, lamina pubesent.  Size: Size: 20mm-40mm long & 7mm-12mm wide. 20mm-40mm long & 7mm-12mm wide.
  • 15. Cultivation & collection Cultivation & collection  It is small shrub up to 2 mt. height. It is small shrub up to 2 mt. height.  Obtained from cultivated & wild zone. Obtained from cultivated & wild zone.  Collected in Collected in September September  Whole branches bearing leaves are dried in the Whole branches bearing leaves are dried in the sun. sun.  Pods and large stalks are separated with Pods and large stalks are separated with sieves. sieves.  Leaves are graded (whole leaves and half-leave Leaves are graded (whole leaves and half-leave mix, siftings). mix, siftings).  Whole leaves – sold to public Whole leaves – sold to public  Rest – used for galenicals (herbal remidies). Rest – used for galenicals (herbal remidies). 15 15
  • 16. 16 16 Senna – chemical Constituents Senna – chemical Constituents  Senna consist four types of glycosides Senna consist four types of glycosides: : Sennoside A Sennoside A Sennoside B Sennoside B Sennoside C Sennoside C Sennoside D Sennoside D In their active costituents are sennoside A, sennosides B In their active costituents are sennoside A, sennosides B  Upon hydrolysis of sennosides it gives two molecules Upon hydrolysis of sennosides it gives two molecules glucose+aglycones: Sennidin A and Sennidin B. glucose+aglycones: Sennidin A and Sennidin B. Rhein Rhein 8-glucosides, Rhein 8-diglucosides 8-glucosides, Rhein 8-diglucosides  Aloe-emodin Aloe-emodin  Crysophenic acid, myricyl alcohol, resin Crysophenic acid, myricyl alcohol, resin  Tinnevellin glycoside(indian senna), 6-hydroxy mucizin Tinnevellin glycoside(indian senna), 6-hydroxy mucizin glucoside glucoside
  • 17. Chemical constituents: Chemical constituents: (i) 1 and 1,8 ‘O’ glucosides (i) 1 and 1,8 ‘O’ glucosides = 1 = 1st st series glycosides series glycosides aglycones: rhein, aloe emodin aglycones: rhein, aloe emodin (ii) dimeric dianthrones (ii) dimeric dianthrones = 2 = 2nd nd series series reduced products reduced products dimer can be split into two parts with FeCl3 hydrolysis and monomer aglycones assayed for
  • 18. Indian Senna Indian Senna  Syn. Syn.: Cassia leaf, Sonmukhi, senai-ki-patti, bhumiari : Cassia leaf, Sonmukhi, senai-ki-patti, bhumiari  B.S.: B.S.: dried leaflets of Cassia angustifolia Vahl.  Family Family: Leguminosae : Leguminosae  G.S.: G.S.: South India, Tinneveley & Ramanathpurum district, South India, Tinneveley & Ramanathpurum district, Pakistan Pakistan  Morphology: Morphology: Color: yellowish green Odour: Slight & characteristic Taste: Bitter & mucilagenous Shape: lanceolate to ovate lanceolate, entire margin, uneven base, acute apex, lamina pubesent. Size: 2.5 cm-6 cm long & 5mm-8mm wide.
  • 19. Cultivation & collection Cultivation & collection  It is small shrub up to 1-1.5 mt. height. Twice a year & after It is small shrub up to 1-1.5 mt. height. Twice a year & after paddy crops. paddy crops.  Soil required is sandy loamy, coarse gravelly, loamy soil Soil required is sandy loamy, coarse gravelly, loamy soil which well ploughed, leveled & semi-irrigated. which well ploughed, leveled & semi-irrigated.  Seeds sawn in Seeds sawn in October & February October & February. Within . Within 2-3 months 2-3 months plant plant are ready for are ready for collection collection. .  Leaflets are collected by hand before flowring. Dried in shade Leaflets are collected by hand before flowring. Dried in shade to maintain natural green color. to maintain natural green color.  1 1st st stage: leaflet are greenish in color & thick stage: leaflet are greenish in color & thick  2 2nd nd stage: harvesting is done after 30 days of 1 stage: harvesting is done after 30 days of 1st st stage stage  3 3rd rd stage: plant are uprooted stage: plant are uprooted  Packing: Packing: in bales with pressure that cause oblique impressions in bales with pressure that cause oblique impressions in leaves. it remain less brittle and in good condition. in leaves. it remain less brittle and in good condition.  Fresh: Fresh: anthron, dried at 20-50◦ - dianthron, above 50◦ - anthron, dried at 20-50◦ - dianthron, above 50◦ - anthraquinone anthraquinone 19 19
  • 20. 20 20
  • 21. Comparison of Comparison of Alexandrian and Tinnevelly Senna Alexandrian and Tinnevelly Senna  Macroscopical Macroscopical  larger than 4 cm in larger than 4 cm in length length  Grey-green Grey-green  Asymmetric at base Asymmetric at base  Broken and curled at Broken and curled at edges edges  Few press markings Few press markings  Macroscopical Macroscopical  exceeds 5cm in length exceeds 5cm in length  Yellow-green Yellow-green  Less asymmetric at Less asymmetric at base base  broken and normally broken and normally flat flat  Often shows Often shows impressions (mid vein) impressions (mid vein) 21 21
  • 22. Comparison between Comparison between Alexandrian and Tinnevelly Senna Alexandrian and Tinnevelly Senna  Microscopical Microscopical  Hairs – numerous Hairs – numerous (approximately three (approximately three epidermal cells apart) epidermal cells apart)  Most stomata have Most stomata have two subsidiary cells two subsidiary cells  Microscopical Microscopical  Hairs less numerous Hairs less numerous (approximately six (approximately six epidermal cells apart) epidermal cells apart)  Stomata have 2-3 Stomata have 2-3 subsidiary cells with subsidiary cells with the respective ratio 7:3 the respective ratio 7:3 22 22
  • 23. Comparison between Comparison between Alexandrian and Tinnevelly Senna Alexandrian and Tinnevelly Senna  Chemical Tests Chemical Tests  Ether extract of Ether extract of hydrolysed acid hydrolysed acid solution of herb with solution of herb with methanolic methanolic magnesioum acetate magnesioum acetate solution gives solution gives  Pink colour in Pink colour in daylight daylight  Pale green-orange Pale green-orange colour in filtered UV colour in filtered UV light light TLC TLC  Hydroxymusizin Hydroxymusizin  Chemical Tests Chemical Tests Same Test Same Test Orange colour in Orange colour in daylight daylight Yellow-green colour Yellow-green colour in filtered UV light in filtered UV light TLC TLC  Tinnevellin glycoside Tinnevellin glycoside 23 23
  • 24. Senna – Allied Drugs & Senna – Allied Drugs & Substitutes Substitutes 1. 1. Bombay, Mecca and Arabian Sennas (found in Bombay, Mecca and Arabian Sennas (found in Cassia Cassia angustifolia angustifolia from Arabia). from Arabia). 2. 2. Palthe senna( Palthe senna( Cassia Auriculata) Cassia Auriculata) 3. 3. Dog senna – Dog senna – Cassia obovata Cassia obovata 4. 4. Cassia podocarpa Cassia podocarpa 5. 5. Argel leaves – Solenostemma argel Argel leaves – Solenostemma argel 6. 6. Coriario myrtifolia Coriario myrtifolia 24 24
  • 25. Senna Fruit Senna Fruit  Definition: Definition: Senna Senna pods pods are the dried, are the dried, ripe fruits of ripe fruits of Cassia Cassia senna senna and and Cassia Cassia angustifolia angustifolia, which , which are commercially are commercially known as Alexandrian known as Alexandrian and Tinnevelly senna and Tinnevelly senna pods respectively. pods respectively. Both have separate Both have separate monographs monographs 25 25
  • 26. Senna Fruit - Collection Senna Fruit - Collection  Pods are collected with Pods are collected with the leaves and dried in the leaves and dried in a similar fashion. a similar fashion.  After separation of the After separation of the leaves, the pods are leaves, the pods are hand-picked into hand-picked into various qualities, the various qualities, the finer being sold finer being sold (commercially), while (commercially), while the finer pieces are the finer pieces are used to make used to make galenicals. galenicals. 26 26
  • 27. Senna Fruit - Constituents Senna Fruit - Constituents  Active constituents Active constituents are found in the are found in the pericarp. pericarp.  Similar to those Similar to those actives of the leaves actives of the leaves  Sennoside A Sennoside A  Sennidin Sennidin 27 27
  • 28. Senna – Additional uses Senna – Additional uses  Medicinal Actions Medicinal Actions  Vermifuge, diuretic, Vermifuge, diuretic, febrifuge febrifuge  Other uses: Other uses: laxative laxative candy (bitter taste). candy (bitter taste).  Also used to treat Also used to treat flatulence, gout, fever. flatulence, gout, fever.  Topically: Topically: poultice poultice prepared with vinegar to prepared with vinegar to treat pimples. treat pimples.  NOTE: Senna may NOTE: Senna may cause urine to become cause urine to become reddish – no clinical reddish – no clinical significance significance. . Contra-indications Contra-indications  Gout, colitis, GI Gout, colitis, GI inflammation. inflammation.  Should not be used with Should not be used with cardiac cardiac glycosides. glycosides.  Seeds/pods Seeds/pods give gentler action give gentler action than leaves: more appropriate for than leaves: more appropriate for the young, elderly and those the young, elderly and those prone to stomach cramps. prone to stomach cramps.  NB: NB: Over-use causes Over-use causes dependency. dependency.  Overdose: nausea, bloody Overdose: nausea, bloody diarrhoea, vomiting and nephritis. diarrhoea, vomiting and nephritis.  Long-term use: dehydration & Long-term use: dehydration & electrolyte depletion, worsening electrolyte depletion, worsening constipation and weakening constipation and weakening intestinal muscles. intestinal muscles. 28 28
  • 29. Some Drugs containing Anthracene derivatives: Some Drugs containing Anthracene derivatives: Senna Senna: :  Leaves and pods contain Sennosides A-D. Leaves and pods contain Sennosides A-D.  The C-C bond protect the anthrone from oxidation. The C-C bond protect the anthrone from oxidation.
  • 30. Chemical test: Chemical test: Borntrager’s and Modified Borntrager’s test: Borntrager’s and Modified Borntrager’s test:  For Aglycones: For Aglycones:  Extract plant material with organic solvent. Extract plant material with organic solvent.  Shake with NH Shake with NH4 4 OH OR KOH. OH OR KOH.  For O-Glycosides: For O-Glycosides:  Boil plant material with dil. HCl for 10 min, filter and shake with Boil plant material with dil. HCl for 10 min, filter and shake with organic solvent (Ether or Benzene). organic solvent (Ether or Benzene).  Separate the organic solvent. Separate the organic solvent.  Shake with NH Shake with NH4 4 OH OR KOH. OH OR KOH.  For C-Glycosides: For C-Glycosides:  Boil plant material with dil. HCl/FeCl Boil plant material with dil. HCl/FeCl3 3 , filter and shake with , filter and shake with organic solvent (Ether or Benzene). organic solvent (Ether or Benzene).  Separate the organic solvent. Separate the organic solvent.  Shake with NH Shake with NH4 4 OH OR KOH. OH OR KOH.  Positive result indicated by Positive result indicated by Rose Red colour Rose Red colour in in the aqueous alkaline layer. the aqueous alkaline layer.
  • 31. Cascara Cascara  Syn: Sacred bark, cortex rhamni, Californian buckthron, cascara Syn: Sacred bark, cortex rhamni, Californian buckthron, cascara sagrada sagrada  B.S.; B.S.; Rhamnus pershiana Rhamnus pershiana  Family: Family: Rhamnaceae Rhamnaceae  G.S.: N.Colifornia, columbia, canada, Kenya G.S.: N.Colifornia, columbia, canada, Kenya  Morphology: Morphology:  Color: outer surface: dark purple to brown (lichens & moss) Color: outer surface: dark purple to brown (lichens & moss)  Inner surface: yellow to reddish brown Inner surface: yellow to reddish brown  Odour: cherecterictic Odour: cherecterictic  Taste: bitter Taste: bitter  Shape: Single squill, curved or channel Shape: Single squill, curved or channel  Size: 5-20 cm long, 2-3 cm wide, 1.2-4 mm thick Size: 5-20 cm long, 2-3 cm wide, 1.2-4 mm thick
  • 32.  C&C: Cascaroside A,B,C,D C&C: Cascaroside A,B,C,D  Use: bark extract Use: bark extract  collected, dried and stored for 12 months (↓ anthraquinone collected, dried and stored for 12 months (↓ anthraquinone content -> less toxic) content -> less toxic)  more violent purgative more violent purgative  griping action griping action  harder to eliminate harder to eliminate  Use Use: night before to clear bowels for x-rays. : night before to clear bowels for x-rays.  Larg dose use as cathartic. Larg dose use as cathartic.
  • 33. Chemical constituents: Chemical constituents: (i) 4 primary glycosides (i) 4 primary glycosides  O- and C- linkages O- and C- linkages (ii) C-glycosides - two aloins (ii) C-glycosides - two aloins  barbaloin – derived from aloe-emodin barbaloin – derived from aloe-emodin  chrysaloin – derived from chrysophanol chrysaloin – derived from chrysophanol (iii) a number of O-glycosides (iii) a number of O-glycosides  derived from emodin oxanthrone, aloe-emodin, chrysophanol derived from emodin oxanthrone, aloe-emodin, chrysophanol (iv) various dianthrones (iv) various dianthrones  incl. emodin, aloe-emodin, chrysophanol, herterodianthrones palmidin A incl. emodin, aloe-emodin, chrysophanol, herterodianthrones palmidin A B C B C (v) aloe-emodin, chrysophanol, emodin in free state (v) aloe-emodin, chrysophanol, emodin in free state To get aglycones FeCl3 To get aloins oxidise with acid
  • 34. Rhubarb Rhubarb  Syn.: Rheum, Radix rhei, da huang Syn.: Rheum, Radix rhei, da huang  B.S.: Peeled & dried rhizomes , root of B.S.: Peeled & dried rhizomes , root of Rheum officinale Rheum officinale Bail., Bail., R.palmetum L R.palmetum L., ., R.rhaponticum R.rhaponticum Willd (chinese) Willd (chinese) R.emodi R.emodi Wall., Wall., R. webbianum R. webbianum Royale (Indian) Royale (Indian)  Family: Polygonaceae Family: Polygonaceae  G.S.: Tibet to south east china, germany, south europe, G.S.: Tibet to south east china, germany, south europe, kashmir, kullu, Sikkim, UP, panjab, nepal kashmir, kullu, Sikkim, UP, panjab, nepal
  • 35. Morphology Morphology  Color: Color: fresh surface after cut pink to dull grey in day fresh surface after cut pink to dull grey in day light & reddish brown U light & reddish brown UV V  Odour: Odour: Characteristics Characteristics  Taste: Taste: Bitter, gritty, astringent Bitter, gritty, astringent  Size: Size: 8-10 cm in length, 3-4 cm thick 8-10 cm in length, 3-4 cm thick  C.C. C.C.: : rhein, glucorhein, emodin, aloe emodin and rhein, glucorhein, emodin, aloe emodin and chrysophenol chrysophenol  Palmidin A, B, C Palmidin A, B, C  Rheinoside A,B,C,D Rheinoside A,B,C,D
  • 36. USE USE  Bitter, stomachic, laxative, purgative, diarrhoea, Bitter, stomachic, laxative, purgative, diarrhoea, eczema, psoriasis eczema, psoriasis  ADULTRANTS ADULTRANTS  Rheum rhaponticum, Rheum rhaponticum,  R. undulatum R. undulatum  R.copactum R.copactum  Japanese rhubarb Japanese rhubarb
  • 37. ALOE ALOE  Syn.: Kumari, musabar, korphad, Gheekunwar, Ghrit Syn.: Kumari, musabar, korphad, Gheekunwar, Ghrit kumara kumara  B.S.: dried juce of leaves of B.S.: dried juce of leaves of Aloe barbadensis Aloe barbadensis Miller( Miller( Curacao Aloe), Curacao Aloe), Aloe perryi Aloe perryi Baker (Socotrine aloe), Baker (Socotrine aloe), Aloe ferox Aloe ferox Miller., Miller., Aloe spicata Aloe spicata Baker (Cape Aloe) Baker (Cape Aloe)  Family: Liliaceae Family: Liliaceae  G.S.: Estern & southern Africa, west Indies, India, G.S.: Estern & southern Africa, west Indies, India, western region. western region.
  • 38. Aloe perryi, barbadensis, ferox Aloe perryi, barbadensis, ferox
  • 39. Cultivation Cultivation  Sandy, lomy, well drained soil. Sandy, lomy, well drained soil.  Acidic, Basic, Neutral. Acidic, Basic, Neutral.  Grow in dry climate condition. It is xerophytic plant. Grow in dry climate condition. It is xerophytic plant.  Propagated by seed, sawn in spring, germinate in 1-6 Propagated by seed, sawn in spring, germinate in 1-6 mnths at 16 degree C. then transferred in pot. mnths at 16 degree C. then transferred in pot.  Offsets & suckers are available in spring. Offsets & suckers are available in spring.  Suckers planted in raw 50 cm in rainy season. Suckers planted in raw 50 cm in rainy season.  2 2nd nd year harvesting is started upto next 12 year. year harvesting is started upto next 12 year.  After that plant are uprooted. After that plant are uprooted.  Aloitic juice collected after cutting leaves. Aloitic juice collected after cutting leaves.
  • 40. Aloe - Liliaceae Aloe - Liliaceae  Definition: Definition: Aloes are the Aloes are the solid residue obtained by solid residue obtained by evaporating the liquid which evaporating the liquid which drains from the transversely drains from the transversely cut leaves of various cut leaves of various Aloe Aloe species. species.  The juice is usually The juice is usually concentrated by boiling and concentrated by boiling and solidifies on cooling. solidifies on cooling.  Official varieties are the Official varieties are the Cape Aloes from SA and Cape Aloes from SA and Kenya ( Kenya (Aloe ferox Aloe ferox), and the ), and the Curacao Aloes from West Curacao Aloes from West Indies ( Indies (Aloe barbadensis Aloe barbadensis). ). 40 40
  • 41. 41 41 Preparation of Cape Aloes Preparation of Cape Aloes  Cape Aloes are prepared from the wild plants Cape Aloes are prepared from the wild plants of Aloe of Aloe ferox ferox. .  Leaves are cut transversely near the base. Leaves are cut transversely near the base.  Two hundred leaves arranged around a shallow hole in Two hundred leaves arranged around a shallow hole in the ground (lined with canvas or goatskin). the ground (lined with canvas or goatskin).  Cut ends overlap & drain into the canvas. Cut ends overlap & drain into the canvas. After 6hrs all the juice is collected. After 6hrs all the juice is collected.  Transferred to a drum. Transferred to a drum.  Boiled for 4hrs on an open fire. Boiled for 4hrs on an open fire.  Poured into tins while hot Poured into tins while hot   solidifies. solidifies.
  • 42. Preparation of Cape Aloes Preparation of Cape Aloes 42 42
  • 43. Cape Aloes - Characteristics Cape Aloes - Characteristics  Dark brown or Green- Dark brown or Green- brown brown  Glassy masses Glassy masses  Thin fragments have Thin fragments have a deep olive colour a deep olive colour Semi-transparent. Semi-transparent. 43 43
  • 44. Cape Aloes - Characteristics Cape Aloes - Characteristics  Powder: green-yellow Powder: green-yellow  When rubbed two pieces When rubbed two pieces of drug together – powder is of drug together – powder is found on the surfaces. found on the surfaces.  Characteristic sour odour Characteristic sour odour (rhubarb/apple-tart odour). (rhubarb/apple-tart odour).  Taste: nauseous and bitter. Taste: nauseous and bitter.  Microscopy: powder in Microscopy: powder in lactophenol – amorphous. lactophenol – amorphous. 44 44
  • 45. Characteristics of Curacao Aloes Characteristics of Curacao Aloes  Colour: yellow-brown – chocolate brown. Colour: yellow-brown – chocolate brown.  Cut at base, V shaped container of wood 1-2 m long with Cut at base, V shaped container of wood 1-2 m long with cut surface towards container. cut surface towards container.  Poor qualities (overheated) black colour. Poor qualities (overheated) black colour.  Opaque Opaque  Breaks with a waxy facture Breaks with a waxy facture  Semi-transparent Semi-transparent  More opaque on keeping. More opaque on keeping.  Nauseous and bitter taste. Nauseous and bitter taste.  Thick hot juice taken completely in copper(metal) pan till it Thick hot juice taken completely in copper(metal) pan till it become thick (hard) become thick (hard) 45 45
  • 46. Socotrine aloe Socotrine aloe  Juice collected on goat skin and allow to dry for long Juice collected on goat skin and allow to dry for long time without heating or boliling. time without heating or boliling.  It forms viscous pasty mass which is filled in It forms viscous pasty mass which is filled in container of wood. container of wood.  Zinzibar aloe Zinzibar aloe  Same as above Same as above  Also called monkey skin aloe. Also called monkey skin aloe.
  • 47. Aloes - Constituents Aloes - Constituents  C-glycosides C-glycosides  Resins Resins  Glycosides Glycosides  Aloin Aloin  Barbaloin Barbaloin  Isobarbaloin Isobarbaloin  Aloe-emodin Aloe-emodin Cape Aloes: Cape Aloes: Also Contain Also Contain Aloinoside A Aloinoside A & & Aloinoside B Aloinoside B (O-glycosides of (O-glycosides of barbaloin) barbaloin) 47 47
  • 49. Aloe Constituents & Chemical Aloe Constituents & Chemical Tests: Tests:  Unlike C-glycosides, O-glycosides Unlike C-glycosides, O-glycosides of of Aloe Aloe are not hydrolysed by are not hydrolysed by heating with dilute acids or alkali. heating with dilute acids or alkali.  Can be decomposed with ferric Can be decomposed with ferric chloride & dilute HCl - chloride & dilute HCl - NB NB: : Modified Modified Borntrager’s Test Borntrager’s Test – oxidative – oxidative hydrolysis. Anthraquinones give a hydrolysis. Anthraquinones give a red red colour when shaken with dilute colour when shaken with dilute ammonia. ammonia.  NB: NB: All Aloes give a strong All Aloes give a strong green green fluorescence fluorescence with borax with borax (characteristic of anthranols) - (characteristic of anthranols) - General test for aloes. General test for aloes. 49 49
  • 50. Aloe Aloe - Uses - Uses  Purgative, abortification, Purgative, abortification, emolient, stomachic, emolient, stomachic, stimulant & tonic. stimulant & tonic.  Used in solar, tharmal, Used in solar, tharmal, radiation burns, in skin radiation burns, in skin irritation irritation  Cosmetic Cosmetic 50 50
  • 51. Aloe – Additional uses Aloe – Additional uses  Medicinal Uses: Medicinal Uses:  Anti-bacterial, anti-fungal, Anti-bacterial, anti-fungal, chologoge, emmenogogue, chologoge, emmenogogue, anti-inflammatory (juice), anti-inflammatory (juice), anti-inflammatory , anti-inflammatory , demulcent, vulnerary, demulcent, vulnerary, immune-stimulating (gel). immune-stimulating (gel). Radiation burns Radiation burns (internal and (internal and external use) external use)  Contra-indications Contra-indications Pregnancy & lactation Pregnancy & lactation (internal uses) (internal uses)  Etymology Etymology  Name derives from Arabic Name derives from Arabic alu, alu, meaning shiny or bitter meaning shiny or bitter in reference to the gel. in reference to the gel.  Other uses Other uses  Khoi-San hunters rub gel Khoi-San hunters rub gel on their bodies to reduce on their bodies to reduce sweating and mask their sweating and mask their scent. scent.  Used to break nail-biting Used to break nail-biting habit. habit. 51 51
  • 52. Aloe vera Products Aloe vera Products  These are derived from These are derived from the mucilage gel – the mucilage gel – parenchyma cells parenchyma cells  Should not be confused Should not be confused with aloes (juice of with aloes (juice of pericycle – juice used for pericycle – juice used for laxative effect). laxative effect).  Cosmetic industry Cosmetic industry (usefulness often (usefulness often exaggerated) - Used as exaggerated) - Used as suntan lotions, tonics and suntan lotions, tonics and food additives. food additives.  Mucilage = Mucilage = polysaccharide of polysaccharide of glucomannans and pectin glucomannans and pectin 52 52