BP504 T.

PHARMACOGNOSY AND
PHYTOCHEMISTRY II (Theory)
UNIT-II
General introduction, composition, chemistry &
chemical classes, biosources, therapeutic uses and
commercial applications of following secondary
metabolites:
Glycosides: Senna (Anthracene Glycoside)
Bitter Almond (Cyanogentic Glycoside)

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 Alexandrian Senna
• Folia sennae Alexandrina, Cassia senna, Egyptian
senna.
• B S : Dried leaflets of Cassia acutifolia family
Leguminosae.
• G S Middle, upper Nile territories, tropical Africa
specially Sudan.
• Collection and Preparation: obtained mainly from
wild sources in Kordofon region of white Nile
Province, & in Khartoum area.
• Collection of leaflets along with branches done when
plants bear unripe fruits, & dried under sunlight.
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 Collection and Preparation
• Leaves-cleaned, graded into entire leaves, entire, broken
leaves, siftings and pods.
• Process of separation carried out by sifting- 1st large stalks
& pods separated, pods are manually plucked out.
• Material that passes through sieves contains entire leaves,
broken leaves, heavier stalks & sand.
• Then mechanically tossed- entire, & broken leaves are
cleared out from other part.
• Once again sifted, to separate mixed leaves, small
fragments & very small leaflets.
• Entire leaves hand picked from mixed leaves, packed in
mats or bales without pressing.
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 Macroscopic & Microscopic Characters
• Macro: Alexandrian senna resembles Tinnevelley senna except
following characters.
• Alexandrian senna - 2-4 cm L, 7-12 mm wide, ovate-lanceolate
shape. Margin entire, curled, base is asymmetrical, more
pubescent, has thin brittle texture. pale greyish-green color
• Micro: Both Alexandrian senna & Tinnevelley senna very
identical in microscopy.
• Various leaf constants : stomatal index, palisade ratio & vein-
islet number.
• Alexandrian senna,
• 1) Stomatal index: 11.4 to 12.2 to 13.3 (For both surfaces)
• 2) Palisade ratio: 4.5 - 9.5 - 19 (upper surface) 3.5 - 7.0 - 14.5
(lower surface)
• 3) Vein-islet number: 25 - 29.5
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 Chemical Constituents
• All the chemical constituents of Alexandrian
senna are same as that of Tinnevelley senna.
• The percentage of sennosides in leaves & pods
is more (3 - 3.6%) as compared to Indian senna.
• Adulterants and Substitutes: found to be
adulterated with Dog senna, Palthe senna,
Bombay, Mecca or Arabian senna.

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 Indian Senna
• Senna leaf, Sennae folium, Senai-ki-patti, Tinnevelley
senna, Cassia senna.
• B S: consists of dried leaflets of Cassia angustifolia or
Cassia senna family Leguminosae. contains not less
than 1.0% w/w of sennosides A and B calculated on dried
basis.
• G S: in Tinnevelley, Madurai and Ramanathapuram
districts of Tamil Nadu. Cudappa district of Andhra
Pradesh, some extent collected from Kutch in Gujarat
and Rajasthan.
• History: known to physicians from olden days , was
included in Unani medicine.

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 Indian Senna
• About 26 species of genus Cassia reported to contain
anthracene derivatives either in free form or glycosides.
• Among all Cassia angustifolia (Indian Senna), Cassia
acutifolia (Alexandrian senna) official in
pharmacopoeias, because of cathartic activity, also
because available in large quantities.
• Other species with known cathartic activity are C. alata,
C. fistula, C. obovata, C. podocarpa, C. sieberiana, C.
sofora, C. dentata, C. javanica etc.

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 Cultivation, Collection and Preparation
• India 25000 hectares of land under cultivation
• Producing 22500 tons of leaves, 7500 tons of fruits/ annum
• Exported by ships from Tuticorin port
• Small shrub 1.5 m, compound paripinnate leaves, each leaf has 3 -
5 - 7 pairs of leaflets.
• Red loamy or coarse gravel soil , but grows on alluvial loamy soil
• Before sowing, land is ploughed twice, harrowed & levelled.
• First sowing- February-March, 2nd sowing in October – November
• Sowing - done by broadcasting method.
• Earlier germination, seed surface is abraded or triturated with sand
• About 15 - 25 kg of seeds required/hectare of land & sown thinly.
• Plants- grown as a semi-irrigated or light-irrigated crop.
• Heavy irrigation, water logging, etc. are avoided.
• Plant cannot survive at very low temperatures.
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 Cultivation, Collection and Preparation
• Plants allowed - grow-5 months till growth of flower stalks
• Cutting given to flower stalks- further branching
• Leguminous plant, but nitrogenous fertilizers is beneficial
because of lack of root nodules.
• After 2 - 3 months of sowing, harvesting of leaves-3 stages.
• 1st plucking-when leaflets thick, full-grown, greenish color
• After 1 month, 2nd plucking- done, last plucking after 4 – 6 W
• Plants are uprooted after 3rd plucking of leaves.
• Content of sennosides in leaves-maximum- when fully grown,
goes on decreasing along with maturation of pods.
• Senna crop taken after rice crop on the same land in same
season gives best yields, senna grown on dry land without
proper irrigation gives poor results.
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Cultivation, Collection and Preparation
• After collection, leaflets- dried under shade or indoor by
spreading them in thin layers.
• Drying takes place within 7 - 10 days, leaves show yellowish
green color.
• Leaves are tossed to separate pods, then packed into bales
under hydraulic pressure.
• Pressing the leaves under hydraulic press produces
transverse line on leaves, absent in Alexendrian senna
leaves.
• During storage, protected from light.
• Generally does not lose potency atleast upto 5 years.
• 1,200 kg of leaves & pods are obtained in 1 hectare of
irrigated land & 700 kg of drug from rain fed land.
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 Macroscopic Characters
• Color-Yellowish-green Odor-Slight, Taste -
Mucilaginous, bitter, characteristic, Size-7to8
mm in width, 25-60 mm in length
• Shape - Leaves are lanceolate, entire, apex is
acute with spine at the top.
• Bases of the leaflets are asymmetrical with
transverse lines, more prominent on lower
surface, while the trichomes are present on
both the surfaces.

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 Microscopic Characters
• Isobilateral leaf,
• Epidermis-unicellular, conical, thick-walled warty
trichomes, are slightly curved at bases, present on both
surfaces.
• Rubiaceous or paracytic stomata present on epidermal
surfaces.
• Palisade tissue present on both the sides, rectangular cells,
enclose cluster-crystals of calcium oxalate.
• Spongy mesophyll & conducting tissues
• Patch of sclerenchyma towards upper epidermis & above
xylem (also known as pericyclic fibres) present.
• Presence of cluster sheath & collenchyma are characteristics
of the senna leaves.
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 Chemical Constituents
• Two anthraquinone glycosides- sennoside A & sennoside B
(not less than 2.5%) accounts for purgative property.
• Tutin (1913) isolated rhein & aloe-emodin
• Stoll, his colleagues 1941 reported isolation of crystalline
sennosides A & B.
• Sennosides A and B - stereoisomers .
• They are dimeric glycosides with rhein dianthrone as aglycone.
• Sennoside B the aglycone is in meso form, & in sennoside A, -
dextrorotatory.
• They also differ in linkage of glucose to the aglycone fraction.
• Purgative activity of sennosides A and B accounts upto 40 –
60% activity of crude drug.

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 Chemical Constituents
• Sugar part of these glycosides- transporting function for the
aglycone upto large intestine & protective action so that
oxidation of aglycone to less active anthraquinone is
prevented.
• Also contains other anthraquinone glycosides in small
amounts, sennosides C & D, rhein 8-glucoside, rhein 8-
diglucoside, aloe-emodin, 8-glucoside, aloe-emodin,
anthrone diglucoside, rhein, kaempferol, aloe-emodin &
isorhamnetin.
• Also contains phytosterol, mucilage, resin, myricyl alcohol,
salicylic acid, chrysophanic acid & calcium oxalate.
• Senna contains 2 naphalene glycosides called Tinnevelley
glycoside & 6 - hydroxy musizin glycoside.
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Structures

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 Chemical Test
• Borntrager's test: For presence of
anthraquinone in senna leaves.
• Drug + dil. H2SO4 + Boil, filter. To filtrate +
benzene/ether / CHCl3 + shake well.
• The organic layer is separated +NH 3 is added
slowly.
• The ammonical layer shows pink to red color
due to presence of anthraquinone glycosides.

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 USES
• As purgative in perpetual constipation.
• Anthraquinone glycosides of senna – absorbed 1st in
intestinal tract, then aglycone part is separated, excreted in
colon.
• These excreted anthraquinone irritate, stimulate the colon
hence movements are increased due to local action.
• The increase in peristalsis also causes reduction in the
water absorption resulting in soft & bulky faeces.
• Griping effect caused by senna is due to resin or emodin
content.
• To counteract the gripping effect, given with carminatives.
• Drug by parenteral mode is secreted in colon & causes
therapeutic action.
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 Adulterants & Substitutes
• Tinnevelley senna : adulterated with Dog senna (C.
obovata), Palthe senna (C. auriculata) & Mumbai, Mecca
& Arabian senna mild variety of C. angustifolia from
Arabia.
• Dog senna-leaves obovate shape,with tapering apex.
Show papillose cells in lower epidermis.
• Contain about 1% of anthraquinone glycosides.
• Palthe senna Characterized by absence of anthraquinone
glycosides.
• Leaflets show long hair & when leaves are boiled with
chloral hydrate solution, shows crimson color.
• Leaflets of Bombay, Mecca, Arabian senna - brownish-
green color & more elongated, narrower in shape. 18
 Senna Pods
• Synonyms : Senna legumes, Sennae fructus,
Senna fruit.
• B S: Dried nearly ripe fruits of Cassia acutifolia
(Alexandrian senna pods), C. angustifolia
(Indian senna pods), family-Leguminosae,
should contain not less than 1.0 % of sennoside
A & B on dried basis.

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 Cultivation, Collection and Preparation for Market
• Pods-collected from same plants as for leaves
• Cultivation procedure- same
• During harvesting both pods & leaves-collected,
dried.
• During sifting, pods separated, manually segregated
into different qualities.
• Superior quality- entire pods without any foreign
organic matter,
• Lower qualities- admixed- broken pods & leaves,
pieces of stems & foreign organic matter. T
• Inferior qualities - used for preparation of galenicals.
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 Macroscopical Characters
• Color - Pale green to greenish-brown. Odor -
None Taste - Slight Size - 4 to 5 cm long, 2 to
2.5 cm in width Shape - The pods are flat, thin
and broadly oblong.
• Apex- round with slightly projecting point
formed by base of the style.
• Extra Features: Seeds of about 6 in number &
obovate in shape are with bluntly pointed
projection at hilum end.
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 Chemical Constituents
• Senna fruits: Contains about 2.5-4.5% sennosides A &
B (Not less than 2.2%)
• Indian senna pods are inferior in glycoside content
(1.5 – 3%).
• The drug responds to Borntrager's test.
• Pods are superior to leaves, as they contain more
percentage of glycosides.
• The glycosides are present in pericarp of pods.
• Seeds contain little qty of sennosides.
• Pods also contain sennoside A1 containing (–)
sennidin 8, 8' diglucoside.
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 Uses
• Purgative due to anthraquinone derivatives.
• Pods do not contain mucilage,easy to handle
for the commercial extraction of
anthraquinone glycosides.
• Sennosides are extracted as their calcium salts.
The pods are preferred to leaves, as they have
less gripping action.

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 CYANOGENETIC GLYCOSIDES
• Also called as cyanophore glycosides- hydrocyanic acid in
aglycone moiety.
• One of the prominent cyanogenetic glycosides-plants is
amygdalin, isolated in 1830.
• Mainly they contain derivatives of mandelonitrile- nitrile
of mandelic acid, which on hydrolysis yields HCN acid &
benzaldehyde.
• Hence, also considered as aldehyde glycosides
• 110 families- plant kingdom- cyanogenetic glycosides.
• Rosaceae- prominent family
• Cyanogenetic glycoside – containing- no specific category
of pharmacological activity- but used for pharmaceutical
purposes.
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 CYANOGENETIC GLYCOSIDES
• Many used- flavouring agents
• Ex: amygdalin- bitter almonds, prunasin-wild
cherry bark, linamarin -linseed, manihotoxin-
Manihot utilissima, sambunigrin- Sambucus
nigra, etc.
• Identification of cyanogenetic glycosides:
Based on liberation of HCN acid on
hydrolysis which changes sodium picrate into
sodium purpurate, evident from color change
from yellow to brick-red.
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 Bitter Almond
• Amygdala amara
• B S: Dried ripe seeds of plants, Prunus
amygdalus var amara, family Rosaceae.
• G S: native of Iran, Asia minor. cultivated in
Sicily, Italy, Spain, Portugal, South France,
Morocco.
• The bitter almond trees cannot be easily
distinguished botanically, from sweet almond
trees (Prunus communis).

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 Bitter Almond
• Macroscopy: Color-Brown Odor - Odorless
Taste-Bitter Size-About 20 mm in L, 125 mm
in W,10 mm in thickness. Shape - Flattened,
oblong, ovoid in shape with markings on testa.

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 Chemical Constituents
• Contain about 40 to 50% of bland fixed oil, 20 % of
proteins, an enzyme emulsin, colorless crystalline bitter
glycoside amygdalin (1 to 3%)
• Also contain 0.5% of volatile oil.
• Amygdalin on hydrolysis due to emulsion in presence of
water decomposes into benzaldehyde & HCN acid.
• HCN acid- very poisonous, makes drug unsuitable for
internal consumption.
• Sweet almonds- do not contain amygdalin (bitter glycoside)
so not bitter in taste. Due to absence of amygdalin, they do
not produce volatile oil on hydrolysis.
• Bitter almond oil contains 80% of benzaldehyde & about 2
to 6% of HCN acid.
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 USES
• Used as sedative due to hydrocyanic acid
content.
• Oil is used in demulcent skin lotion.
• Also used in the preparation of amygdalin,
bitter almond water, in perfumery and in the
form of liquors.
• Bitter almond oil should not be used for
flavoring of foods.

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 Reference
• Pharmacognosy, C.K. Kokate, A.P. Purohit,
S.B. Gokhale, 54th Ed. 2017, Nirali
Publication, New Delhi

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