Glycosides

Topic Slide no.
Introduction 3
Classification 7
Distribution 10
Anthracene glycosides 11
Aloes 14
Senna 27
Rhubarb 35
Rubia 43
St. John’s wort 49
Isothiocyanate glycosides 57
Brassica 58
Cabbage 69
Cyanogenic glycosides 77
Bitter almond 79
Biosynthesis of Amygdalin 88
Wild cherry Bark 91

Introduction
 Glycosides are the molecules in which a sugar part is bound to some other non-
sugar part.
 Glycosides play numerous important roles in living organisms.
 Plants store important chemicals in the form of inactive glycosides; if these
chemicals are needed, the glycosides are brought in contact with water and an
enzyme and the sugar part is broken off, making the chemical available for use.
 Many such plant glycosides are used as medications.
 Formally, a glycoside is any molecule in which a sugar group is bonded through its
anomeric carbon to another group via a glycosidic bond.
 The anomeric carbon is the carbon derived from the carbonyl carbon compound (the
ketone or aldehyde functional group) of the open-chain form of the carbohydrate
molecule.

 The sugar group is known as the Glycone and the non-sugar group as the
Aglycone or Genin part of the glycoside.
 The glycone can consist of :
◦ Single sugar group (Monosaccharide) or
◦ Several sugar groups (Oligosaccharide)
Sugars found in glycosides may be
• Monosaccharides
–Glucose
– Rhamnose
– Fructose
• Deoxysugars (more rare)
– Cymarose (found in the cardiac glycosides)

Terms used to describe glycosides
 A Glycoside is a
 Glucoside –Has glucose as the sugar component
 Pentoside –Has a sugar such as arabinose
 Rhamnosides – Contains rhamnose
 Rhanmoglucosides – Contains both rhamnose and glucose

Glycosidic Bond
 A glycosidic bond is a certain type
of a functional group that joins
alcoholic group of a Carbohydrate
molecule to an aglycone molecule.
 A substance containing a
glycosidic bond is a Glycoside

Classification of glycosides
 Glycosides can be classified by :
 The nature of Glycone
 Number of sugars
 Nature of the glycoside
 Botanical source
 Therapeutic use
 The type of Glycosidic Bond
 The Glycosidal Linkage and
 Chemical nature of Aglycone.

On the basis of glycosidic linkage
 O-glycosides: Sugar molecule is combined with phenol or –OH group of aglycon, for
example, Amygd-aline, Indesine, Arbutin, Salicin, cardiac glycosides, anthraxquinone
glycosides like sennosides etc
 N-glycosides: Sugar molecule is combined with N of the –NH (amino group) of
aglycon, for example, nucleosides
 S-glycosides: Sugar molecule is combined with the S or SH (thiol group) of aglycon,
for example, Sinigrin
 C-glycosides: Sugar molecule is directly attached with C—atom of aglycon, for
example, Anthraquinone glycosides like Aloin, Barbaloin, Cascaroside and Flavan
glycosides, etc.

On the basis of Aglycone
Sr.No. Class Example
1. Anthraquinone glycosides Senna, Aloe, Rhubarb,etc
2. Sterol or Cardiac glycosides Digitalis, Thevetia, Squill,etc
3. Saponin glycosides Dioscorea, Liquorice, Ginseng, etc
4. Cyanogenetic & Cyanophoric glyosides Bitter almond , wild bark cherry ,etc
5. Thiocynate & Isothiocynate glycosides Black mustard
6. Flavone glycoside Ginkgo
7. Aldehyde glycosides Vanilla
8. Phenol glycosides Bearberry
9. Steroidal glycosides Solanum
10. Bitter & Miscellaneous glycosides Gentian, Picrrohiza, etc

Distribution of glycosides
Glycosides are the class of compounds abundant in nature. Some plant families containing
important glycosides are listed bellow :
1. Scrophulareaceae (Digitalis purpurea and Digitalis lanata, Picrorhiza kurroa).
2. Apocyanaceae (Nerium oliander and Thevetia peruviana).
3. Liliacea (Urgenea indica and U. maritima, Aloe vera)
4. Leguminocae (Cassia acutefolia and C. angustefolia, Gly-cyrrhiza glabra, Psoralea corylifolia)
5. Dioscoreaceae (Dioscorea floribunda)
6. Rosaceae (Prunus amygdalus, Carategus oxycantha)
7. Cruciferae (Brassica sp.)
8. Gentianaceae (Gentian and Chirata)
9. Acanthaceae (Kalmegh)
10. Simarubaceae (Quassia)
11. Umbelliferae (Ammi majus, Ammi visnaga)
12. Rutaceae: Citrus sp. (Ruta graveolens)
13. Polygonaceae (Fagopyrum sp.)
14. Myrtaceae (Eucalyptus sp.)

Anthracene Glycosides
 Anthracene glycosides are chiefly found in dicot plants but to some extent it is also
found in monocot and lower plants.
 It consists of glycosides formed from aglycone moi-eties like anthraquinones,
anthranols, anthrones or dimers of anthrones or their derivatives.
 Anthrones are insoluble in alkali and do not show strong fluorescence with them, while
anthronols which are soluble in alkali show strong fluorescence.
 The reduced anthraquinones are biologically more active.
 Anthroquinones that are present in fresh drugs are in reduced form, which on long
storage get oxidized and hydrolysed, Glycosides of reduced derivatives are more active
than oxidized aglycones. This is due to the fact that sugars take the glycosides to the
site of action and thus are more active.

 Anthraquinone is an aromatic organic compound and a derivative of anthracene
 It has the appearance of yellow or light grey to grey-green solid crystalline powder.
 Its chemical formula is C14H 8O2. It melts at 286Â°C, boils at 379.8Â°C.
 It is insoluble in water or alcohol, but dissolves in nitrobenzene and aniline. It is
chemically fairly stable under normal conditions.
 Anthraquinone naturally occurs in some plants (e.g. aloe, senna, rhubarb and cascara),
fungi, lichens and insects, where it serves as a basic skeleton for their pigments.
 Natural anthroquinone derivatives tend to have laxative effects
 The common aglycones are aloe-emodin, emodin, rhein, chrysophanol and physcion
which may exist as anthraquinones, anthranols or anthrones.
 The sugars presents are usually arabinose,rhamnose and glucose.
 In the drug originally glycosides of reduced derivatives or their dimers are present.
 During drying and storage by hydrolysis and oxidation free anthraquinones are produced.

 Occurrence - The plant is native to
North Africa, Southern Europe, and the
Canary Islands. Today, aloe vera is
grown in tropical climates worldwide.
 Aloe vera (Linnaeus) is present
in India and distributed in the extreme
dry parts of Rajasthan and Gujarat
state. In other states of India, it is
grown as a medicinal plant.
Aloe vera
Family - Asphodelaceae (Liliaceae)
Aloes

Chemical composition
Summary of the chemical composition of A. vera leaf pulp and
exudate
Class compounds Property/activity
Amino acids Provides 20 of the 22 required
amino acids and 7 of the 8
essential ones.
Basic building blocks of
proteins in the body and
muscle tissues.
Anthroquinones Provides aloe emodin, aloetic
acid, alovin, Anthracine.
Analgesic, antibacterial
Enzymes Anthranol, barbaloin,
chrysophanic acid, smodin,
ethereal oil, ester of cinnamonic
acid, isobarbaloin, resistannol
Antifungal & antiviral activity
but toxic at high
concentrations.

class compounds Property/uses
Hormones Auxins and gibberellins Wound healing and
antiinflammatory.
Minerals Calcium, chromium, copper,
iron, manganese, potassium,
sodium and zinc.
Essential for good health
Salicyclic acid Aspirin like compounds Analgesic
Saponins Glycosides Cleansing and antiseptic
properties
Sugars Monosaccharides: Glucose and
Fructose Polysaccharides:
Glucomannans/polymann ose
Anti-viral, immune modulating
activity of acemannan
Vitamins A, B, C, E, choline, B12, folic
acid
Antioxidant (A,C,E), neutralises
free radicals.

Chemical constituents in Aloe vera
 The two-main class active constituent of the Aloe vera plant extract
are chromone and anthraquinone and its glycoside derivatives,
alongside others such as phenylpyrone derivatives, flavonoids,
phenylpropanoids, coumarins, phytosterols, naphthalene analogs,
lipids, and vitamins.
 Anthracene glycosides(11 to 40%)
 Barbaloin or Aloin, a C glycoside (not easily hydrolysable with dil.
Acids and linkage between the sugar and the aglycone is through C-C).
 Aloinosides A and B (only in Cape aloes).
 Resins (resinotannol +cinnamic acid or coumaric acid).
 Also contains Aloetic acid, homonataloin etc

Aloe Emodin
Schematic representation of A. vera leaf pulp structure and
its components

Cultivation and collection
 It is an evergreen perennial growing to 0.8 m by 1 m at a slow rate. The plant prefers
light (sandy) and medium (loamy) soils, requires well-drained soil and can grow in
nutritionally poor soil.
 The plant prefers acid, neutral and basic (alkaline) soils. It cannot grow in the shade. It
requires dry or moist soil and can tolerate drought.
 They are xerophytic plant. It can be propagated by seeds. Seeds are sown in the spring
in a warm green house. The seed usually germinates in 1–6 months at 16°C.
 The seedlings are transferred to the pots containing well-drained soil. They are allowed
to grow in sunny part for at least their first two winters.
 The offsets will be available, usually in spring. The plants produce offsets quite freely
and they can be divided at any time of the year as long as it is warm enough to
encourage fresh root growth to allow reestablishment of the plants. Young offsets are
planted in the soil after the rainy season in rows situated at a distance of 60 cm.

 In the second year leaves are collected by the natives by protecting their hands because
of the spiny nature of leaves. The leaves are cut near the base, kept inside of kerosene
tins and taken them to a central place for the preparation of aloe. Juice of aloe is present
in parenchymatous cells of pericycle that are mucilage cells. In a single incision
mucilage cells exert pressure on pericycle cells and the entire juice from the leaves is
drained out

Preparation of Aloes
 Curacao or barbados aloe :- In West Indies the cut leaves are arranged with their cut surface on
the inner side, on the sides of V shaped vessel of about 1–2 m long and the flowing juice is
collected in a tin vessel that is placed below the V-shaped vessel This juice thus collected is
concentrated either by spontaneous evaporation, or more generally by boiling until it becomes of
the consistency of thick honey. These conditions favours the crystallization of barbaloin and this
aloe contains crystals of barbaloin because of the presence of which it becomes opaque and so
also known as hepatic or livery aloe. On cooling, it is then poured into gourds, boxes, or other
convenient receptacles and solidifies.
 Socotrine aloe :- When it is prepared, it is commonly poured into goat skins, and spontaneous
evaporation is allowed for about a month when it becomes viscous pasty mass which are then
packed into cases. In European countries it is dried in wooden pans with hot air till moisture is
about 10%.

Preparation
 Zanzibar aloe :- This aloe is prepared similar to Socotrine aloe. It is packed in skins, of
carnivorous animals. This aloe is also known as monkey skin aloe.
 Cape aloe :- The leaves of the plants from which Cape aloe is obtained are cut off near
the stem and arranged around a hole in the ground, in which a sheep skin is spread, with
smooth side upwards. When a sufficient quantity of juice has drained from the leaves it
is concentrated by heat in iron cauldrons and subsequently poured into boxes or skins in
which it solidifies on cooling. Large quantities of the drug are .exported from Cape
Town and Mossel Bay.

Chemical Tests
Boil 1 gm of drug with 100 ml water, allow it to cool; add 1 gm kieselguhr, stir it well and filter
through filter paper.
 1. Borax Test: Take 10 ml of aloe solution and to it add 0.5 gm of borax and heat; a green
coloured fluorescence is produced indicating the presence of aloe-emodin anthranol.
 2. Modified Anthraquinone Test: To 0.1 gm of drug, 5 ml of 5% solution of ferric chloride is
added followed by the addition of 5 ml dilute hydrochloric acid. The mixture is heated on water
bath for 5–6 min and cooled. An organic solvent (benzene or chloroform) is added and shaken.
Separate the organic solvent layer and add an equal volume of dilute ammonia. The ammoniacal
layer produces pinkish red colour.
 3. Bromine Test: To 5 ml of aloe solution, add equal volume of bromine solution; bulky yellow
precipitate is formed due to the presence of tetrabromaloin
 4. Nitrous Acid Test: To 5 ml of aloe solution, add little of sodium nitrite and few drops of dilute
acetic acid; it produces Pink or purplish colour. Zanzibar and Socotrine aloes give negative test.

Chemical tests
 5. Nitric Acid Test: 2 ml of concentrated nitric acid is added to 5 ml of aloe solution;
Curacao aloe gives deep reddish-brown colour, Socotrine aloe gives pale yellowish-
brown colour, Zanzibar aloe gives yellowish-brown colour and Cape aloe first produces
brown colour which on standing changes to green.
 6. Cupraloin Test: 1 ml of the aloe solution is diluted to 5 ml with water and to it 1
drop of copper sulphate solution is added. Bright yellow colour is produced which on
addition of 10 drops of saturated solution of sodium chloride changes to purple and the
colour persist if 15–20 drops of 90% alcohol is added. This test is positive for Curocao
aloe, faint for Cape aloe and negative for Zanzibar and Socotrine aloes .

Uses :-
 The drug Aloes is one of the safest and stimulating purga-tives, in higher doses
may act as abortifacient. Its action is exerted mainly on the large intestine; also
it is useful as a vermifuge.
 The plant is emmenagogue, emollient, stimu-lant, stomachic, tonic and
vulnerary.
 Extracts of the plant have antibacterial activity. The clear gel of the leaf makes
an excellent treatment for wounds, burns and other skin disorders, placing a
protective coat over the affected area, speeding up the rate of healing and
reducing the risk of infection.
 To obtain this gel, the leaves can be cut in half along their length and the inner
pulp rubbed over the affected area of skin. This has an immediate soothing
effect on all sorts of burns and other skin problems

Substituents and Adulterants
 A. candelsbmm (Natal aloes) is dull greenish black to dull brown
in colour, opaque. When scraped it gives a pale greyish green or a
yellow powder. It can be distinguished as it gives negative test to
borax test and produces a deep blue colour. Jafferabad aloes and
the Mocha aloes are the other two type of aloe which is used as
adulterant

Senna
Synonyms
Alexandrian senna, Tinnevelly senna, Folia senna.

 Biological source :- Senna leaf consists of the dried leaflets
of Cassia acutifolia Delile (C. senna L.) known as Alexandrian
senna and of C. angustifolia Vahl., which is commercially known as
Tin-nevelly senna. It belong family Leguminosae .
 Geographical source :- Alexandrian senna is indigenous to South
Africa. It widely grows and sometimes is cultivated in Egypt and in the
middle upper territories of Nile river. It is also cultivated in Kordofan
and Sennar regions of Sudan. Indian or Tinnevelly senna is indigenous
to southern Arabia and cultivated largely in Tinnevelly and
Ramnathpuram districts of Tamilnadu. It also grows in Somaliland,
Sindh and Punjab region.

Chemical constituents
 Senna contains sennosides A and B (2.5%) based on the
aglycones sennidin A and B, sennosides C and D which are
glycosides of heterodianthrones of aloe-emodin and rhein are
present.
 Others include palmidin A, rhein anthrone and aloe-emodin
glycosides. Senna also contains free chryso phanol, emodin and
their glycosides and free aloe-emodin, rhein, their
monoanthrones, dianthrones and their glycosides.
 Mucilage is present in the epidermis of the leaf and gives red
colour with ruthenium red.

Cultivation & Collection
 Senna plant is a small shrub of 1–1.5 m height with paripinnate compound leaves. Tinnevelly senna is
mostly cultivated in well-ploughed, levelled, rich clayed semiirrigated land sometimes after paddy crop in
South India. Propagation is done by seeds which are rubbed with coarse sand and sown thinly by
broadcasting or in rows 30 cm apart, first during February–March and second after rain in July. Seeds
germinate on the third day.
 The crop becomes ready for harvesting after about 2 months but first plucking of leaflets is done after 3
months of sowing when the leaves appears mature, thick and bluish in colour.
 Second plucking is fol-lowed after a month and subsequent pluckings after 4–6 weeks. The plant can
survive for two to three years, but it is grown as an annual.
 After third plucking the plants are uprooted. Plant shows great tolerance for salinity. It some-times shows
die-back symptoms in which the branches or shoots die from the tip inward, which is caused by parasites or
environmental conditions.
 Leaflets of Tinnevelly senna are collected by careful plucking from luxuriantly grown plants and
compressed into bales

Collection & cultivation
 Alexandrian senna is obtained almost entirely from the wild and
sometimes from the cultivated plants.
 At the stage of fully formed fruits, branches are cut off and
rapidly dried in the sun. Pods and large stalks are first separated
by using sieves. Leaves separated from stalks are graded into
whole leaves, whole and half leaves and shiftings.
 Whole leaves and shiftings are generally used for making
galenical preparations. The leaves are packed loosely in bales for
marketing.

Chemical tests
 Borntrager test for anthraquinones: The leaves are
boiled with dilute sulphuric acid and filtered. To the filtrate
organic solvent like benzene, ether or chloroform is added and
shaken. The organic layer is separated, and to it add ammonia
solution. The ammoniacal layer produces pink to red colour
indicating the presence of anthraquinone glycoside

Uses :-
 Senna leaves are used as laxative.
 It causes irritation of large intestine and have some griping effect. Thus they are
prescribed along with carminatives.
 Senna is stimulant cathartic and exerts its action by increasing the tone of the smooth
muscles in large intestine
 It is used to treat constipation and also to clear the bowel before diagnostic
tests such as colonoscopy.
 Senna improves skin afflictions such as pimples, acne and beneficial for
weight management. The senna leaves are best for medication.

 Synonyms :- East Indian Rhubarb, China Rhubarb, Turkey Rhubarb
 Biological source :- Rhubarb consists of the peeled dried rhizomes and roots of Rheum
palmatum Linn., belonging to family Polygonaceae
 Geographical source :- It is mainly found in E. Asia, N.W. China in Yunnan, W.
Sichuan, E. Xizang and Gansu, Thibet and India.

 Rhubarb contains free anthraquinones, their glycosides, reduced derivatives, anthrones,
or dianthrone and heterodi-anthrones.
 The anthraquinones of rhubarb are chrysophanol, aloe-emodin, emodin, physcion and
rhein.
 Anthrones or dianthrones are of chrysophanol, emodin and aloe-emo-din.
 Heterodianthrones contain two different molecules of anthrones .
 It also contains tannoid constituents, starch and calcium oxalate. There are also several
resinous matters, one of which, Phaoretin, is purgative, and mineral compounds are also
present.
 The astringency of Rhubarb is due to a peculiar tannic acid (Rheo-tannic), which is soluble
in water and alcohol

 The plant is perennial growing to 3 m by 2 m. The plant prefers medium (loamy) and
heavy (clay) soils, requires well-drained soil and can grow in heavy clay soil. The
plant prefers acid, neutral and basic soils.
 Drug is collected from wild plants but is also cultivated to some extent. The plant grows
at an altitude of 2,500–4,000 m. It can grow in semishade or no shade.
 It requires moist soil. Plants can be grown in quite coarse grass, which can be cut
annually in the autumn. Seeds are sown in autumn in a shaded cold frame. The seed can
also be sown in spring in a cold frame. When large enough to handle, seedlings are
pricked out and transferred into individual pots and allowed to grow them on in the
green house or cold frame for their first winter, then they are transplanted out in the
spring.

 The rootstocks are divided in early spring with a sharp knife, making sure that there is at
least one growth bud on each division and the required amount of drugs is collected and the
remaining are planted.
 Rhizomes are large and roots are thick branched, Drug is collected in autumn in September
or October from 6 to 15 years old plants. Rhizomes are dug out, crown and lateral roots are
removed and the outer bark is separated by peeling. The rhizomes that are small in size are
kept as such or cut into transverse slices and so they are round.
 Large rhizomes are made flats by making cut into longitudinal slices. These slices are dried
by boring holes in the flat pieces and passing thread through the holes and hanging between
shades of trees. In absence of the required climatic conditions the drugs are dried artificially
heated stones, which are previously heated by woodfire. Drug dried in this way is called
high dried. The drugs that are dried in above said manner exerts an unpleasant odour and
darker in colour and is considered inferior. The remaining bark is peeled off and graded
according to size, shape and quality

Chemical tests
1. Rhubarb powder when treated with ammonia pink colour is produced.
2. With a solution of 5% potassium hydroxide it gives blood red colour.

Uses
 The root is anticholesterolemic, antiseptic, antispasmodic, antitumor, aperient,
astringent, cholagogue, demulcent, diuretic, laxative, purgative, stomachic and tonic.
 The roots contain anthraquinones, which have a purgative effect, and also tannins and
bitters, which have an opposite astringent effect.
 When taken in small doses, it acts as an astringent tonic to the digestive system, whilst
larger doses act as a mild laxative.
 The root is taken internally in the treatment of chronic constipation, diarrhoea, liver and
gall bladder complaints, haemorrhoids, menstrual problems and skin eruptions due to an
accumulation of toxins.
 This remedy is not prescribed for pregnant or lactating women, or for patients with
intestinal obstruction. Externally, the root is used in the treatment of burns.

 Rubia cordifolia, often known as common madder or Indian madder, is a species of
flowering plant in the coffee family, Rubiaceae. It has been cultivated for a red
pigment derived from roots.
 Species: R. cordifolia
 Family: Rubiaceae
 Order: Gentianales
 Geographical source :- Rubia cordifolia has an extremely large area of distribution,
ranging from Africa to tropical Asia, China, Japan and Australia. In Africa it is
found from Sudan and Ethiopia to South Africa.
 Indian distribution :-
 State - Kerala, District/s: Palakkad, Kozhikkode, Kollam, Idukki, Malappuram,
Kannur, Wayanad

 Quinones
The plant contains quinines, mainly anthraquinone glycosides and include 1-hydroxy 2-
methoxy anthraquinone, 1, 4- dihydroxy-2- methyl-5-methoxy anthraquinone, 1,3-
dimethoxy 2- carboxy anthraquinone and rubiadin)
 Iridoids
6-methoxygeniposidic acid is found along with manjistin, garancin and alizarin
 Oleananes triterpinoid
Rubiprasin A, B, and C along with arborane triterpinoids, like rubiarbonol A, B, C, D, E and
F have been isolated
 Bicyclic hexapeptides
The compounds having antitumour activity have been isolated and identified chemically.

 Anthraquinones
The coloring matter present in the roots of R. cordifolia is a mixture of purpurin (trihydroxy
anthraquinone) and manjistin (xanthopurpurin-2-carboxylic acid). The roots contain small
amounts of xanthopurpurin or purpuroxanthin and pseudopurpurin (purpurin-3-carboxylic
acid)
 The plant also contains dihydromollugin, mollugin, rubilactone.
 Purpurin, belonging to the lipocalin family of proteins, is a fast dye for cotton printing
and forms complexes with various metal ions. It is a glycosaminoglycan binding protein
as well as a retinol binding protein.

Alizarin, or 1, 2-dihydroxyanthraquinone or
mordant red, is the red dye originally derived from
the root of the madder plant. In 1869, it became the
first natural pigment to be duplicated synthetically.
The word alizarin is derived from the Arabic word
al-usara, which means juice.
Purpurin (1, 2, 4-trihydroxyanthracene-9, 10-Dione

Traditional uses in different systems of herbal
medicine
 Unani system of medicine
R. cordifolia has been prescribed for paralysis, dropsy, jaundice, amenorrhoea, urinary
tract obstructions, skin disorders of many varieties, menstrual disorders (excessive or
painful bleeding), renal stone, urinary disorders and blood detoxification
 Chinese system of medicine:
Roots help menstrual flow, promote blood circulation, promote urination,stop coughing
blood or vomiting blood, nose bleeding. The plant is also useful in treatment of missing
menses due to blood stasis, cold damp heat bi (pain and inflammation caused by bleeding
and blood circulation stasis), injuries from impacts and in jaundice and edema
 Ethnoveterinary usage
R. cordifolia is used in the treatment of liver fluke, dysentery, maggots, wounds and
intestinal worms in animals.

St. John’s Wort
Hypericum perforatum

 Hypericum perforatum
 Other names for it include Tipton's weed, rosin rose, goatweed, chase-devil,
or Klamath weed.
 St. John's wort (Hypericum perforatum) is a flowering shrub native to Europe.
It gets its name from the fact that it often blooms on the birthday of the
biblical John the Baptist.
 Through colonization it is now also found in USA and parts of Canada and
Australia and was initially thought to be a weed.

 Chemical investigations into the constituents of H. perforatum have detected seven
groups of medicinally active compounds.
 The most common classes include naphthodianthrones, phloroglucinols, and flavonoids
(such as phenylpropanes, flavonol glycosides, and biflavones), as well as essential oils.
 Two major active constituents have been identified: hypericin (a naphtodianthrone) and
hyperforin (a phloroglucinol). However, roughly 20% of extractable compounds are
considered biologically active
Chemical structures of (a) hypericin, and (b) hyperforin.

 NAPHTHODIANTHRONES :- The class of compounds isolated
from H. perforatum that is the most researched is the naphthodianthrones,
which have been standardized in concentrations ranging from 0.1% to 0.3%.
 The most common naphthodianthrones include hypericin, pseudohypericin,
isophypericin, and protohypericin .
 Of these, hypericin—an anthraquinone-derived pigment that is responsible for
the red color of SJW oils—is the best known. Hypericin is found in the
flowers, particularly in the black dots that are located along the petals.
 FLAVONOIDS :- Flavonoids found in SJW range from 7% in stems to 12% in
flowers and leaves . Flavonoids include flavonols (kaempferol, quercetin),
flavones (luteolin), glycosides (hyperside, isoquercitrin, and rutin), biflavones
(biapi-genin), amentoflavone, myricetin, hyperin, oligomeric
proanthocyanadins, and miquelianin, all of which are biogenetically related .
Rutin concentration is reported at 1.6% .

 LIPOPHILIC COMPOUNDS :-
Extracts of SJW contain several classes of lipophilic compounds with demonstrated therapeutic
value, including phloroglucinol derivatives and oils. Hyperforin, isolated in concentrations of 2-
4.5% , is a prenylated phloroglucinol expanded into a bicyclo nonaendionol (2,1), substituted
with several lipophilic isoprene chains . Hyperforin is unstable in the presence of both light and
oxygen . Despite numerous attempts by various researchers, total synthesis of hyperforin has not
been accomplished to date . Other phloroglucinols include adhyperforin (0.2%-1.9%),
furohyperforin, and other hyperforin analogs. Essential oils are found in concentrations ranging
from 0.05% to 0.9% . They consist mainly of mono- and sesquiterpenes, specifically 2-methyl-
octane, n-nonane, α- and β-pinene, α-terpineol, geranil, and trace amounts of myrecene,
limonene, and caryophyllene, among others.
ADDITIONAL COMPOUNDS
Other compounds of various classes have been identified in H. perforatum. These include tannins
(ranging from 3% to 16%), xanthones (1.28 mg/100 g), phenolic compounds (caffeic acid,
chlorogenic acid, and p-coumaric acid), and hyperfolin. Additional compounds include, to a
lesser extent, acids (nicotinic, myristic, palmitic, and stearic), carotenoids, choline, pectin,
hydrocarbons, and long-chain alcohols . Several amino acids that have been isolated from the
herb include cysteine, glutamine, leucine, lysine, and GABA (γ-aminobutyric acid )

Uses :-
 Likely Effective for
• Depression. Taking St. John's wort extracts by mouth improves depressive mood and
decreases nervousness and tiredness related to depression. Certain St. John's wort
products might work as well as some prescription drugs. But not all St. John's wort
products available on the market will be the same quality as those used in these studies.
So they may not work as well. Also, St. John's wort might not be as effective for more
severe cases of depression.
 Possibly Effective for
• Symptoms of menopause. Most research shows that taking St. John's wort by mouth can
help reduce hot flashes and other symptoms of menopause. Some evidence shows that
specific combinations of St. John's wort plus black cohosh are also beneficial. But not all
St. John's wort combination products seem work.
• Emotional distressed caused by extreme focus on a physical symptom (somatic symptom
disorder). Treatment with a specific St. John's wort product (LI 160, Lichtwer Pharma)
daily for 6 weeks seems to reduce symptoms of this condition.

Isothiocyanate
Isothiocyanate is the chemical group –N=C=S, formed by substituting the oxygen
in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are
produced by enzymatic conversion of metabolites called glucosinolates.
Isothiocyanates are abundant in cruciferous vegetables such as broccoli,
watercress, Brussels sprouts, cabbage, Japanese radish and cauliflower,
and they significantly contribute to the cancer chemopreventive activity of these
vegetables.

Brassica
The classical view of yellow Brassica-napus fields and a closer view-of-oilseed-rape

Introduction
 Brassica is a genus of plants in the mustard family (Brassicaceae)
 The members of the genus may be collectively known either as cabbages
mustards
 Crops from this genus are sometimes called cole crops from the Latin caulis (=
stem or cabbage)
 This genus contains more important agricultural and horticultural crops
 It also includes a number of weeds wild taxa escapees from cultivation
 It includes over 30 wild species and hybrids numerous additional cultivars and
hybrids of cultivated origin
 Most: annuals or biennials Some: small shrubs

The genus Brassicais classified as:
Kingdom Planta
Division Tracheophyta
Subdivision Spermatophyta
Class Angiospermae
Subclass Dicotyledonae
Order Papaverales
Family Cruciferae or Brassicaceae
Genus Brassica

Brassica
Brassica plant as host showing leaf feeding, oviposition and trophic interactions by larvae and adults
of Pieris brassicae and Delia radicum and their parasitoids

Brassica rapa
Brassica rapa is a diverse wild plant species known with several common names: wild turnip, field
mustard, turnip mustard, wild mustard, wild kale or bird rape. It has bright yellow flowers which
attract bees.

The relationships of some of the more common brassicas

 Where do brassicas originate?
North Eastern Mediterranean
Brassica oleracea and Brassica rapa originated around 3 million years ago in the North
Eastern Mediterranean, from where ancestors of Brassica oleracea spread through
Europe and Brassica rapa to Asia.
 What plants are considered brassicas?
Brassica species and varieties commonly used for food include broccoli,
cauliflower, cabbage, choy sum, rutabaga, turnip and some seeds used in the production
of canola oil and the condiment mustard.
 Where is Brassica rapa native?
Eurasia
It is native to Eurasia. Typical habitats include cropland, weedy fields, roadsides,
gravelly areas along railroads, and waste areas. This plant is usually found in areas with a
history of disturbance where there is scant ground vegetation.
 What foods are brassicas?
A member of the family of vegetables that includes broccoli, Brussels sprouts,
cabbage, cauliflower, collard greens, kale, and turnips. These vegetables contain
substances that may protect against cancer. Also called cruciferous vegetable.

Geographical distribution
Geographic distribution of collection sites
of Indian mustard (B. juncea)
Worldwide distribution of the Brassicaceae

Brassica Phytochemical content
 The major phytochemical compounds quantitatively estimated in various species
of Brassicainclude phenolics, flavonoids, ascorbic acid (Vit. C) glucosinolates,
carotenoids, and tocopherols.
 The aqueous and organic extracts of the various parts of Brassicaplants have been
found to contain the considerable amounts of phenolics, flavonoids, carotenoids,
ascorbic acid, and tocopherols which advocate the suitability of Brassicaplants for
pharmaceutical applications.
 Among Brassicaspecies, B. oleraceavar. Capitata,B. oleraceavar. Italica, and B.
juncea, B. rapaare high in phenolics, flavonoids and carotenoids.
 (total phenolic content: TPC, total flavonoid content: TFC, ascorbic acid content: AAC,
total glucosinolate content: TGC, total carotenoid content: TCC, and total tocopherol
content: TTC)

Species/subspecies Parts used Extracting solvent TPC (GAE) TFC AAC
B. oleracea
Capitata F. Alba
Leaves
Ethanol,
methanol, acetone
14.78–18.7 mg/g
extract
4.12–8.80 mg QE/g
extract
70% methanol,
phosphoric acid
20–29 mg/100 g fw 18–35 mg/100 g fw
Terminal leaf buds Water 43.87 mg/g
B. oleracea
Capitata F. Rubra
Leaves 70% methanol
134–171 mg/100 g
fw
B. oleracea
Capitata L.
Leaves 80% methanol 3.64 μM/g dw
Leaves
Varying polarity
solvents
34–520 mg/100 g
dw
3.20–8.30 g/100 g extract
Varying polarity
solvents
402–556 mg/100 g
fw
Flower buds
80% methanol,
phosphoric acid
4.14 mM/g dw 62–72 mg/100 g fw
leaf buds Water 53.85 mg/g

Species/subsp
ecies
Parts used
Extracting
solvent
TPC (GAE) TFC AAC
B. oleracea
Italica
Floret
Ethanol,
methanol,
acetone
17.9–
23.6 mg/g
extract
12.5–
17.5 mg CE/10
0 g
Water
48.76 μg/ml
extract
69.64 μg/ml
extract
25.0–
29.48 μg/ml
extract
Florets,
Leaves
Methanol,
phosphoric
acid
533.6–
740 mg/100 g
317–
816 mg CE/100
g
298.6–
474.7 mg/100
g
Florets Methanol
43–75 mg/kg
dw
2.1–4.0 mg/kg
dw
Inflore-scence Water 1.816 mg/g fw
B. oleracea
Gemmifera
Sprouts
Ethanol,
methanol,
acetone
18.12–
20.4 mg/g
extract
12.1–
15.4 mg CE/10
0 g
70% methanol,
phosphoric
acid
133–
140 mg/100 g
fw
129–
127 mg/100 g
fw

Cabbage
Brassica oleracea
Botanical name Brassica oleracea
Family Brassicacae
Cultivar group Capitata
origin Eastern Mediterranean and Asia minor
region (prior to 1000 B.C.)
Cultivar group members White cabbage (capitata var. alba L.)
Red cabbage (capitata f. rubra) Savoy
cabbage (capitata var. sabauda L.)

Brassica
Plant morphological diversity of Brassica wild species

Major organic compounds detected in the cabbage leaves
Sr.No. Name of compound Composition (%)
1. Phenanthrene 9.44
2. Anthracene 6.39
3. Oxalic acid 3.22
4. Napthalene 5.82
5. b- Pinene 2.10
6. 2- Octen- 3 – ol 8.22
7. 3-Octanol 1.92
8. 3,4-Dihydroxymendelic acid 1.65

Health Benefits of Cabbage
 1. Lowers the Signs of Ageing
Cabbage and other cruciferous vegetables contain a high amount of
Vitamin C and E, which help in the production of collagen, the compound which
keeps the skin elastic and wrinkle-free. Vitamin A along with Vitamin D protects the
skin and gives you a youthful skin.
 2. Helps Fight Free Radicals
Cabbage is rich in antioxidants. Antioxidants help fight oxidative damage
caused by free radicals and prevent a whole range of ailments.
 3. Speeds Up the Recovery Process
Cabbage leaves are used as a poultice. Using these leaves can ease skin
eruptions caused by acne, psoriasis, eczema, ulcers, wounds, insect bites and
rashes. Grated leaves or blended leaves can be applied directly over the affected
area with some dressing for faster healing.

 4. Improves Complexion
Cabbage can also cure acne and other skin conditions. Some steamed
cabbage leaves compressed in a cotton cloth can be placed on the affected area
overnight for best results. The high levels of potassium and Vitamin A also
improve complexion.
 5. May Provide Relief From Allergies
Cabbages and other cruciferous vegetables of its kind contain anti-
inflammatory properties. They are rich in sulforaphane and glutamine which are
powerful anti-inflammatory agents. Regular consumption can ease health
conditions worsened by inflammation such as allergies, irritation, fever, joint pain
and skin disorders.
 6. May Prevent Cancer
The Brassica vegetables such as cabbage contain a significant amount of
glucosinolates that have strong anti-cancer properties. These compounds
scavenge free radicals which are bad for health and contribute to cancers of
different kinds. Red cabbages are particularly loaded with compounds such as
sinigrin, lupeol and sulforaphane with anti-cancer properties.

 7. Good for the Digestive Tract
Cabbage is high in fibre, which makes it healthy for the digestive tract. Eating
cabbage can provide relief from constipation. This is very effective in treating
constipation and related gastrointestinal disorders.
 8. Promotes Weight Loss
As cabbage is loaded with essential nutrients and contains almost no calories or
fats, hence it is perfect for people who are on a weight loss diet. If you don’t like to eat
cabbage in the form of vegetable, you can drink cabbage juice.
 9. Protects the Eye
Vitamin A which is an essential nutrient for our eyes is present in cabbage and
helps maintain good vision. The beta-carotene, an antioxidant present in cabbage is
also helpful in preventing macular degeneration and delay the onset of cataracts.
 10. Improves the Health of Hair
Cabbage being rich in many of the essential nutrients helps maintain healthy hair
and prevents hair fall. It also prevents dry hair and protects the hair strands from
physical damage. Vitamin C which is found in cabbage is essential for the production of
the protein keratin which primarily makes up the hair and nails in the body.

 11. Improves the Health of the Heart
Red cabbages are rich in compounds called anthocyanins which give them their
characteristic purple colour. Studies have shown a link between diet consisting of foods rich in
these compounds and lowering of heart disease. Along with this, cabbages are also good sources
of potassium and calcium essential for healthy functioning of the heart.
 12. Good for Diabetic Patients
The potassium present in cabbage is not only good for lowering blood pressure but helps
maintain blood sugar levels. It also improves mental well being by reducing stress and anxiety
 13. Boosts Immunity
Being loaded with Vitamin C and antioxidants, cabbage helps boost immunity. It supports the
immune system and fights off various diseases.
14. Helps Treat Peptic Ulcer
The presence of anti-inflammation compounds such as glucosinolates helps reduce peptic
ulcers in the stomach. Cabbage juice is a remedy for ulcers. It eases the inflammation in the
stomach lining and speeds up the recovery process.

Cyanogenic Glycosides
 Cyanogenic glycosides are chemical compounds contained in foods that
release hydrogen cyanide when chewed or digested. The act of chewing
or digestion leads to hydrolysis of the substances, causing cyanide to be
released
 Important staple foods for some parts of the world (such as cassava and
sorghum) contain cyanogenic glycosides. Other edible plants containing
cyanogenic glycosides include bamboo shoot, flaxseeds, and seeds of stone
fruits such as apricot and peach, seeds of peas and beans such as lima
beans, and shell of soya beans.
 Most cyanogenic glycosides are biosynthetically derived from the amino
acids : valine, leucine, isoleucin, tyrosine or phenylalanine.

Amygdalin Linamarin Dhurrin
Lotaustralin Taxiphyllin Prunasin
Common Cyanogenic glycoside structures

Bitter almond Synonym: Amygdala amara.
Scientiﬁc name : Prunus amygdalus var.amara
Family : Rosaceae

 Biological Source Bitter almond comprises of the dried ripe kernels of Prunus
amygdalus Batsch. Var amara (DC) Focke; Prunus communis Arcang., P. amygdalus Bail;
and Amygdalus communis Linn., belonging to family Rosaceae.
 Geographical Source Bitter almond trees are mostly native of Persia and Asia Minor.
They are also cultivated in the cooler parts of Panjab and Kashmir, Italy, Sicily, Portugal,
Spain, Southern France and Morocco.

 Fats: oleic acid , palmitic acid, linolic fatty acid
 Glycoside: Cyanogenic glycoside 2.5-4% (Amygdalin)
 Vitamins: vit E, vitB complex (riboflavin etc),
 minerals, flavanols, etc.

Chemistry
 The main chemical components of bitter almond oil are benzaldehyde and
hydrocyanic (prussic acid).
 Benzaldehyde does not occur as such in the plant, but is formed, together with
hydrogen cyanide, by the hydrolytic cleavage of the glycoside amygdalin.

Chemical Tests
 The general tests of the cyanogenetic glycosides by means of microchemical reactions in
naturally occurring crude drugs are based on their hydrolysis to yield hydrocyanic acid. In
fact, there are four speciifc and characteristic reactions to detect the presence of liberated
HCN, namely:
 1. Ferriferrocyanide Test:
Macerate 1 g of the powdered drug with 5 ml of alcoholic KOH (5% w/v) for five
minutes. Transfer it to an aqueous solution containing FeSO4 (2.5 %w/v) and FeCl3 (1% w/v),
and maintain at 60-70°C for 10 minutes. Now, transfer the contents to HCl (20%) when the
appearance of a distinct prussian blue colour confirms the presence of HCN.
 2. Precipitation of Hg from HgNO3:
The reduction of aqueous mercurous nitrate solution (3% w/v) to metallic Hg by HCN
being observed by an instant formation of black metallic Hg in the cells.

 3. Grignard Reaction Test:
First of all, dip a strip of white filter paper into a solution of picric acid (1 % w/v in
water) drain and then dip into a solution of sodium carbonate (10% w/v in water) and drain.
Now, place the crushed and moistened drug material in a small Erlenmeyer flask, and
subsequently suspend the strip of the prepared sodium picrate paper above the material and
stopper the flask with an air tight cork. Maintain the flask in a warm place for 1 hour when
the liberated HCN would turn the sodium picrate paper from its original yellow colour to
brick red colour due to the formation of sodium isopurpurate (Grignard’s Reaction).
 4. Cuprocyanate Test:
First of all, saturate pieces of filter paper in a freshly prepared solution of guaic
resin dissolved in absolute ethanol and allow them to dry completely in air. Now, carefully
moisten a piece of the above paper with a very dilute solution of CuSO4 and place it into
contact with a freshly exposed surface of the drug. In case, HCN is generated, it will give rise
to a distinct stain on the paper.

Pharmacological effects
 Anticancer properties :
Amygdalin, one of the most important compounds of bitter almond, has
been known to be a unique substance to treat cancer for over 100 years. It is
thought to be the cause of anticancer properties that can contribute to treating
different cancers.
 Antimicrobial properties:
Different extracts of bitter almond can exert different antimicrobial
effects. Of these extracts, methanolic extract was found to exert more optimal
effects on Bacillus subtilis and Staphylococcus aureus.

Uses
1. Bitter almonds are employed as sedative due to HCN content.
2. The fixed oil of bitter almond finds its use as demulscent in skin-lotion.
3. It is also employed in the preparation of amygdalin and bitter almond water.
Traditional uses of bitter almond:
Bitter almond is highly valuable in traditional and modern medicine .
In Iranian traditional medicine,bitter almond essential oil is used to treat burns and
wounds and to protect stomach, bitter almond ointment or essential oil is used to
treat acne, joint pain, hair loss.

Biosynthesis of Amygdalin
 Defense mechanism: ability to produce toxic amounts of HCN, which is
extremely toxic to most of the organism as it inhibits cytochrome oxidase and
other respiratory enzymes.
 Shikimic acid pathway.. Amino acid phenyl alanine.
 Amygdalin serves as a phagostimulant for malacosoma americana.
(A natural plant substance that induces feeding by an insect.)
 Young fruits only contain prunasin, but after development, the cotyledons
contains amygdalin.

Illustrated steps for biosynthesis of
Amygdalin.

The metabolic pathways for synthesis and catabolism of the cyanogenic glucosides prunasin and amygdalin in
almonds. Biosynthetic enzymes (black lines) are: CYP79 and CYP71, Cyt P450 monooxygenases; GT1, UDPG-
mandelonitrile glucosyltransferase; and GT2, UDPG-prunasin glucosyltransferase. Catabolic enzymes (dashed
lines) are: AH, Amygdalin hydrolase; PH, prunasin hydrolase; MDL1, mandelonitrile lyase; and ADGH*,
amygdalin diglucosidase (putative).

Introduction
➢ Synonyms : Virginian Prune, Black Cherry, Virginian Bark, Cortex Pruni.
➢ Biological Source It is the dried bark of Prunus serotina , Ehrk, and Prunus
macrophylla Sieb et Zucc, belonging to family Rosaceae.
➢ Geographical Source Wild Cherry bark is found to be indigenous to the
Eastern States of USA and certain parts of Canada. North America
generally.

 This tree grows from 50 to 80 feet high, and 2–4 feet in diameter. The bark is collected
in autumn from young branches and stem. In some cases cork and cortex are removed
after collection, by peeling. If the bark is peeled it is called rossed bark and if not
peeled, it is unrossed barks. It is carefully dried and preserved in airtight containers.

 1- The cyanogenic glycoside Prunasin and Prunase enzyme in bark.
 Prunasin is hydrolysed in presence of water by prunase enzyme present in the
drug into benzaldehyde, glucose and hydrocyanic acid.
 2- Organic acids; benzoic acid, trimethyl-gallic acid and p-coumaric acid.
 3- Tannins and traces of volatile oils.

Chemical test
 Test for hydrocyanic acid (Guignard's test):
One gram of small pieces of the bark are put into a test tube + 1.0 ml of water and
the tube is closed with a cork holding a strip of moistened sodium picrate paper
(Guignard paper) between it and the tube the HCN evolved over a period of 30
minutes change to the yellow color of the picrate paper to BRICK RED colour.

Uses
➢ Astringent tonic, pectoral, sedative and expectorant.
➢ It has been used in the treatment of bronchitis of various types.
➢ It is valuable in catarrah, whooping cough, and dyspepsia..
➢ Antitussive; in cough preparations, for chronic, dry and whooping coughs,
bronchitis, increases perspiration rate and mild sedative.
➢ Nervous dyspepsia, poor digestion, gastritis and diarrhea.
➢ Antibacterial and antiviral.

References
 https://www.ncbi.nlm.nih.gov/books/NBK92750/
 https://www.webmd.com/vitamins/ai/ingredientmono-329/st-johns-wort
 https://in.iherb.com
 https://www.researchgate.net/figure/2-Plant-morphological-diversity-of-
Brassica-wild-species_fig2_225208492
 https://www.nordgen.org/en/plant-portraits/brassica-rapa/
 https://www.researchgate.net/figure/The-classical-view-of-yellow-Brassica-
napus-fields-and-a-closer-view-of-oilseed-rape_fig4_41700461
 https://www.sciencedirect.com/topics/pharmacology-toxicology-and-
pharmaceutical-science/brassica

References
 https://www.intechopen.com/chapters/61233
 https://www.researchgate.net/figure/Geographic-distribution-of-collection-
sites-of-Indian-mustard-B-juncea-germplasm_fig1_304104644
 https://www.researchgate.net/figure/Worldwide-distribution-of-the-
Brassicaceae_fig1_226858290
 https://www.slideshare.net/RioneDrevale/brassica-print?from_action=save
 https://scialert.net/fulltext/?doi=ajbkr.2011.68.76
 https://parenting.firstcry.com/articles/magazine-20-benefits-of-cabbage-
you-may-not-be-aware-of/

References
 https://www.slideshare.net/DrDuryabJamil/bitter-almonds-by-dr-duryab-
jamil
 http://www.epharmacognosy.com/2012/04/bitter-almond.html
 https://www.slideshare.net/MarwaFayed1/all-bark
 http://www.pharmacy180.com/article/wild-cherry-bark-194/
 https://www.researchgate.net/figure/Illustrated-steps-for-biosynthesis-of-
Amygdalin_fig2_338069726
 https://www.slideshare.net/priyankagoswami/anthraquinonenapthaquionecy
anogenetic-glycoside
 http://www.pharmacy180.com/article/chemical-tests-of-glycosides-166/

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