content
Flavonoids (importance, Physiological role and Therapeutic uses).
Flavonoids biosynthesis, General Properties and Tests for identity.
Flavone Glycosides (Diosmin and Apiin)
Flavonol Glycosides (rutin and Quercetrin)
Flavanone Glycosides (Hesperidin)
Silymarin (flavonolignans)
Isoflavonoids (Genistein)
Coumarin Glycosides
Unit II Introduction to secondary metabolite
Steroids, Cardiac Glycosides & Triterpenoids:
Liquorice, Dioscorea, Digitalis
For video lecture suscribe youtube channel snehal chakorkar.
Primary metabolites:
General introduction, detailed study with respect to chemistry, sources,
preparation, evaluation, preservation, storage, therapeutic used and
commercial utility as Pharmaceutical Aids and/or Medicines for the
following Primary metabolites:
(c) Carbohydrates: Acacia,
Unit II Introduction to secondary metabolite
Steroids, Cardiac Glycosides & Triterpenoids:
Liquorice, Dioscorea, Digitalis
For video lecture suscribe youtube channel snehal chakorkar.
Primary metabolites:
General introduction, detailed study with respect to chemistry, sources,
preparation, evaluation, preservation, storage, therapeutic used and
commercial utility as Pharmaceutical Aids and/or Medicines for the
following Primary metabolites:
(c) Carbohydrates: Acacia,
Unit II Introduction to secondary metabolite
Volatile oils
Mentha, Clove, Cinnamon, Fennel, Coriander.
For video lecture suscribe yutube channel snehal chakorkar
Black and green tea, its preparation, tea cultivation, preparation of black tea and green tea, chemical constituents (caffeine, catechin, tannins) and uses
Definition
Glycosides are non-reducing organic compounds that on hydrolysis with acids or enzymes yield:
1- A sugar part (or glycone, formed of one or more sugar units).
2- A non-sugar part (or aglycone, also called genin).
GPAT
Niper &
other pharma competative exams...
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Describes in detail the complete biological source and synonyms of the plant Cinnamon. Gives important macroscopic characters and microscopic characters as seen in transverse and the lateral sections. Also gives important chemical constituents of the plant, its uses, difference between two species of Cinnamon: Cassia cinnamon and Ceylon cinnamon and some marketed pharmaceutical preparations of Ceylon cinnamon.
When
food containing, lignan precursors are
consumed they are converted to the enterolignans,
enterodiol and enterolactone by bacteria that
normally colonize the human intestine
Enterodiol
and enterolactone have weak estrogenic
activity but may also exert biological effects through
nonestrogenic mechanisms
Because
enterodiol and enterolactone can mimic
some of the effects of estrogens, their plant derived
lignan precursors are classified as phytoestrogens
Lignan
precursors that have been identified in the
human diet include pinoresinol, lariciresinol,
secoisolariciresinol, matairesinol and others
Unit II Introduction to secondary metabolite
Volatile oils
Mentha, Clove, Cinnamon, Fennel, Coriander.
For video lecture suscribe yutube channel snehal chakorkar
Black and green tea, its preparation, tea cultivation, preparation of black tea and green tea, chemical constituents (caffeine, catechin, tannins) and uses
Definition
Glycosides are non-reducing organic compounds that on hydrolysis with acids or enzymes yield:
1- A sugar part (or glycone, formed of one or more sugar units).
2- A non-sugar part (or aglycone, also called genin).
GPAT
Niper &
other pharma competative exams...
For more posts, follow us on .... be
@pharmahelpers
@pharmahelpers
@pharmahelpers
Also follow us on...
Facebook @ Pharma Helpers
Whatsapp @ 8421773854 OR https://chat.whatsapp.com/FFVRcxiiqC91PvnEvmK2F1
Instagram @ https://www.instagram.com/p/COM-VYqJ3Xo/?igshid=1ac01ibq2sa2k
Describes in detail the complete biological source and synonyms of the plant Cinnamon. Gives important macroscopic characters and microscopic characters as seen in transverse and the lateral sections. Also gives important chemical constituents of the plant, its uses, difference between two species of Cinnamon: Cassia cinnamon and Ceylon cinnamon and some marketed pharmaceutical preparations of Ceylon cinnamon.
When
food containing, lignan precursors are
consumed they are converted to the enterolignans,
enterodiol and enterolactone by bacteria that
normally colonize the human intestine
Enterodiol
and enterolactone have weak estrogenic
activity but may also exert biological effects through
nonestrogenic mechanisms
Because
enterodiol and enterolactone can mimic
some of the effects of estrogens, their plant derived
lignan precursors are classified as phytoestrogens
Lignan
precursors that have been identified in the
human diet include pinoresinol, lariciresinol,
secoisolariciresinol, matairesinol and others
Structural elucidation and isolation of glycoside, purine and flavanoidsSana Raza
Unit three of chemistry of natural products, consist of the method of extraction, isolation and structure elucidation of Glycoside(digoxin), Flavanoids( quercetin), Lignans( Podophyllotoxin), Purines (caffeine)
Cellulose
■ Cellulose is a linear polymer, made of (1-4) linked D-glucose (-glucan).
■ Cellulose is the chief polysaccharide of plant cell walls.
■ It constitutes 50% in wood, 50% in paper and 90% cotton hairs.
■ Complete acid hydrolysis of cellulose with hydrochloric acid gives -D-glucose
Flavonoids classification, isolation and identificationMona Ismail
Flavonoids are groups of polyphenolic compounds which are found in fruits, flowers, seeds & vegetable.
(named from the Latin word flavus meaning yellow, their colour in nature)
This ppt contains a suitable contents. This notes is effective for B.Pharm & D.Pharm students. In this notes we all the related topic of secondary metabolites. In this notes we all sub topics of secondary metabolites such as Alkaloids, Glycosides, Terpenoids, Taninns, Resins, Flavonoids, etc.
a molecule in which a sugar is bound to another functional group via a glycosidic bond.
anthraquinone, coumarin, cyanogens (cyanohydrin), flavonoids, glucosinolates (or thioglycosides), phenols, steroidal, terpenoids, and saponins.
Digoxin (Lanoxicaps, Lanoxin, Digibind)
Digitoxin (Crystodigin)
Cardiac glycosides are medicines for treating heart failure and certain irregular heartbeats. They are one of several classes of drugs used to treat the heart and related conditions.
A Glycoside is any molecule in which sugar group is bonded through its anomeric carbon to another grp via Glycosidic bond.
A glycosidic bond is a type of chemical bond that joins sugar molecule to another molecule.
The sugar grp is known as glycone and non-sugar grp as aglycone or genin.
The glycone and aglycone portions can be chemically separated by hydrolysis in presence of acid.
The glucose can consist of a single grp or several sugar groups.
General Methods for Isolation of Terpene Hydrocarbons
1. Fractional Distillation:
• This usually takes place under vacuum or in an atmosphere of inert gas,?? as many hydrocarbons are sensitive to heat in atmospheric oxygen (product name? ? ?).
• This can carried out by gradual increase of the distillation temperature by (1-5oC) or (5-10 oC) according to the boiling point of components.
2. Preparation of the Corresponding Crystalline Additive Products “Adducts”:
Characteristic addition products are formed by N2O3 (Dinitrogen trioxide), N2O4, NOCl (Nitrosyl chloride) and NOBr to yield nitrosites, nitrosates, nitrosochlorides, and nitrosobromides, respectively.
content
Anthracene glycosides
mechanism of Action
Chemistry
Tests for Identification of anthracene glycosides
I- Anthraquinones (alizarin, aloe-emodin and rhein)
Metabolism of Diacerein (1-8 Diacetyl Rhein)
II- Anthranols and anthrones (Chrysarobin and Barbaloin)
III- Dianthrones (Sennosides A-D and Hypericin)
content
The evaluation of drugs
Evaluation methods of the crude drugs
Chemistry of Crude Drugs
Primary Metabolites (starch, protein and fixed oil)
secondary Metabolites (glycosides, alkaloids and volatile oil)
The living plant cell
What is the main differences between plant cell and animal cell??
Cell wall: Formed of cellulose.
Chloroplast: Responsible for photosynthesis.
Vacuole: much larger in plant cells, store any nutrients and waste products .
content
Deterioration of Herbal Drugs
Primary Factors (Light, Moisture/ Humidity, Temperature and Air Oxidation)
Secondary Factors
Control Measures for Deterioration
Adulteration of Crude Drugs
Detection of Adulterants
content
Cultivation and preparation of crude drugs
1- Cultivation
2- Collection
3- Preservation of plant material (Drying, stabilization and fermentation)
4- Packing
5- Storage
6- Grinding of crude drugs
7- crude drug extraction
content
Important definitions
Crude drug description
Pharmacist should have a good knowledge of natural drugs (why)
Nomenclature of drugs (Origin of the crude drug)
Classification of drugs for study
Definitions “volatile oils”, “Ethereal oils” or Essential oils”
Volatile oils: Complex liquid mixtures of odoriferous compounds of varying chemical composition, which easily evaporate when exposed to air at room temperature, and which are used for either their specific therapeutic activity or their aroma.
Aromatherapy is a branch of complementary medicine, which depends on the use of aromatic plants, their extracts, mainly their essential oils to promote health, beauty and vitality.
بعض العلاقات... مثل القرابة والصداقة...
تشتمل على معاني جميلة... و روابط انسانيه مهمة...
ولكن البعض يتغيرون ... تغيرهم الاحداث ...
فالاحداث هي امتحانات لقوة طرفي اي معادلة تربط اي اثنين...
أستاذ جامعي يقع قتيلا في مؤتمر تقيمه كلية الحقوق... أثناء نقاش مع زميل له ...
على الرغم من ان القتيل كان شخص وفيا ومعطاء لكل المحيطين به...
لكن هذا لم يمنع يد خائنة وخسيسة من ان تقتله...
وتجعل من الخيانة والغدر مقابلا للوفاء... كما كانت من قبل جزاء لسنمار.
عندما يتلوث الدم.... ليس بالجراثيم وانما بآثام القلب وشروره ليضخ دما ملوثا بالحقد والكراهيه لينقله الى اقدام تسوقك الى جريمه والى يدا لتجعل من السلاح الذي تمسكه ادآة سوداء ورسالة من قلب مريض رسالة بالموت
عندما يتحول نجاحك الى مرض وعقده نفسيه كبيره لشخص لا يستطيع ان يلاحقه .....
عندما لا تفلح مؤمرات ذلك الشخص في افشالك.....
عندما يقرر انك من يقف في طريقه وانه يتوجب عليه ازاحتك من طريقه بأي وسيله وان كانت القتل..
عندها فقط بدأت المذبحه...
هاجس جال بخاطر رجل الاعمال الناجح حسن المصري بأن اذى ما سيلحق بابنه الوحيد خالد وان كارثة ما ستحدث لشركته...
وبدون مقدمات تحول الهاجس لسلسله من الجرائم البشعه والغامضه التي راح ضحيتها هو وكل الموجوديين بقصره ...
وفي لحظاته الاخيره ... وبدون ادنى تفكير حاول ان يحمي اغلى الناس في حياته ...ابنه ....من تلك اليد الاثمه...
لتكن تلك المكالمه ذات الكلمات القليله .... يبلغ فيها خالد ابنه برساله...
رساله من قلب محب.... رساله مضمونها
ان الاب هو الملاذ الاخير
حصن يحمي ابنائه الى النهايه
ان الاب هو.....
الطابية الاخيره
Phenolic compounds
Precipitate animal proteins in hides and converting them into leather. “Tanning Industry”
Present in plants, ex. grapes, cranberry, hamamelis and tea leaves.
Opium is the air-dried milky exudate, or latex, obtained by incising the unripe capsules of the opium poppy Papaver somniferum (Papaveraceae).
the ripe capsule can contain up to 0.5% total alkaloids
Opium represents a much concentrated form and up to 25% of its mass is composed of alkaloids ( more than 40 alkaloids).
Structural features of Cinchona alkaloids
1- The basic skeleton of Cinchona alkaloids is Ruban-9-Ol.
2- Ruban nucleus is a combined skeleton formed from a quinoline ring attached to a quinuclidine ring (a bicyclic ring contain N) through methylene group.
Unit 8 - Information and Communication Technology (Paper I).pdfThiyagu K
This slides describes the basic concepts of ICT, basics of Email, Emerging Technology and Digital Initiatives in Education. This presentations aligns with the UGC Paper I syllabus.
June 3, 2024 Anti-Semitism Letter Sent to MIT President Kornbluth and MIT Cor...Levi Shapiro
Letter from the Congress of the United States regarding Anti-Semitism sent June 3rd to MIT President Sally Kornbluth, MIT Corp Chair, Mark Gorenberg
Dear Dr. Kornbluth and Mr. Gorenberg,
The US House of Representatives is deeply concerned by ongoing and pervasive acts of antisemitic
harassment and intimidation at the Massachusetts Institute of Technology (MIT). Failing to act decisively to ensure a safe learning environment for all students would be a grave dereliction of your responsibilities as President of MIT and Chair of the MIT Corporation.
This Congress will not stand idly by and allow an environment hostile to Jewish students to persist. The House believes that your institution is in violation of Title VI of the Civil Rights Act, and the inability or
unwillingness to rectify this violation through action requires accountability.
Postsecondary education is a unique opportunity for students to learn and have their ideas and beliefs challenged. However, universities receiving hundreds of millions of federal funds annually have denied
students that opportunity and have been hijacked to become venues for the promotion of terrorism, antisemitic harassment and intimidation, unlawful encampments, and in some cases, assaults and riots.
The House of Representatives will not countenance the use of federal funds to indoctrinate students into hateful, antisemitic, anti-American supporters of terrorism. Investigations into campus antisemitism by the Committee on Education and the Workforce and the Committee on Ways and Means have been expanded into a Congress-wide probe across all relevant jurisdictions to address this national crisis. The undersigned Committees will conduct oversight into the use of federal funds at MIT and its learning environment under authorities granted to each Committee.
• The Committee on Education and the Workforce has been investigating your institution since December 7, 2023. The Committee has broad jurisdiction over postsecondary education, including its compliance with Title VI of the Civil Rights Act, campus safety concerns over disruptions to the learning environment, and the awarding of federal student aid under the Higher Education Act.
• The Committee on Oversight and Accountability is investigating the sources of funding and other support flowing to groups espousing pro-Hamas propaganda and engaged in antisemitic harassment and intimidation of students. The Committee on Oversight and Accountability is the principal oversight committee of the US House of Representatives and has broad authority to investigate “any matter” at “any time” under House Rule X.
• The Committee on Ways and Means has been investigating several universities since November 15, 2023, when the Committee held a hearing entitled From Ivory Towers to Dark Corners: Investigating the Nexus Between Antisemitism, Tax-Exempt Universities, and Terror Financing. The Committee followed the hearing with letters to those institutions on January 10, 202
Acetabularia Information For Class 9 .docxvaibhavrinwa19
Acetabularia acetabulum is a single-celled green alga that in its vegetative state is morphologically differentiated into a basal rhizoid and an axially elongated stalk, which bears whorls of branching hairs. The single diploid nucleus resides in the rhizoid.
The French Revolution, which began in 1789, was a period of radical social and political upheaval in France. It marked the decline of absolute monarchies, the rise of secular and democratic republics, and the eventual rise of Napoleon Bonaparte. This revolutionary period is crucial in understanding the transition from feudalism to modernity in Europe.
For more information, visit-www.vavaclasses.com
Synthetic Fiber Construction in lab .pptxPavel ( NSTU)
Synthetic fiber production is a fascinating and complex field that blends chemistry, engineering, and environmental science. By understanding these aspects, students can gain a comprehensive view of synthetic fiber production, its impact on society and the environment, and the potential for future innovations. Synthetic fibers play a crucial role in modern society, impacting various aspects of daily life, industry, and the environment. ynthetic fibers are integral to modern life, offering a range of benefits from cost-effectiveness and versatility to innovative applications and performance characteristics. While they pose environmental challenges, ongoing research and development aim to create more sustainable and eco-friendly alternatives. Understanding the importance of synthetic fibers helps in appreciating their role in the economy, industry, and daily life, while also emphasizing the need for sustainable practices and innovation.
Biological screening of herbal drugs: Introduction and Need for
Phyto-Pharmacological Screening, New Strategies for evaluating
Natural Products, In vitro evaluation techniques for Antioxidants, Antimicrobial and Anticancer drugs. In vivo evaluation techniques
for Anti-inflammatory, Antiulcer, Anticancer, Wound healing, Antidiabetic, Hepatoprotective, Cardio protective, Diuretics and
Antifertility, Toxicity studies as per OECD guidelines
2. content
Flavonoids (importance, Physiological role and Therapeutic uses).
Flavonoids biosynthesis, General Properties and Tests for identity.
Flavone Glycosides (Diosmin and Apiin)
Flavonol Glycosides (rutin and Quercetrin)
Flavanone Glycosides (Hesperidin)
Silymarin (flavonolignans)
Isoflavonoids (Genistein)
Coumarin Glycosides
3. Glycosides Dr. Mostafa Hegazy
Flavonoids
They are one of the most diverse and
widespread group of phenolic natural products.
They are amongst the dye stuffs and water-
soluble pigments of plant origin.
1- They are often yellow pigments.
2- Red and blue pigments e.g. anthocyanin
derivatives.
They are one of the most important
constituents of the human diet (Nutraceutical).
They are found in fruits, vegetables, nuts, seeds,
stems, flowers and common drinks e.g. tea.
4. Nutraceutical is a comprehensive
term which includes substances that
are considered as foods, parts of
foods or dietary supplements that
may claim to provide medical or
health benefits – this includes the
treatment of or prevention of disease.
Flavonoids bind to a range of cellular
receptor sites and show a wide range
of biological activities.
5. Physiological role for the plant
1- They are the pigments of flowers and
attract pollinating birds and insects.
2- They play a role in plant growth control
by inhibiting and activating enzymes.
Therapeutic activities and uses
Most flavonoid-containing plants are used as
antioxidant, antibacterial, and anti-
inflammatory. Several members of the
group are known to possess antiviral,
anticancer spasmolytic, estrogenic,
cardiotonic and hepatoprotective
activities.
6. Mechanisms of antioxidant
activity
1- Complexing of heavy metal ions.
2- Electron transferring in enzyme
systems, e.g. oxido-reductases.
3- Free radical scavenging.
7. Therapeutic use Constituents Natural source
Cardiotonic Procyanidins Crateagus spp
Antioxidant Catechins Thea sinensis (green tea
leaves)
Antiviral Flavonoids Licorice
Anticancer Isoflavonoids (Daidzin and
Genistin)
Soya bean
Reduction of capillary fragility Flavonols e.g.Rutin
Flavones e.g. Diosmin
Ruta spp
Buchu leaves
Diuretic Flavonoids Buchu leaves
Broom tops
Calcium antagonist Quinochalcones e.g.
Tinctormine
Saflower
Antihepatotoxic Flavanonols e.g. Astilbin
Flavolignans e.g.Silybin
Smilax spp
Silybium marianum
Therapeutic uses of flavonoids and related compounds
8. Glycosides Dr. Mostafa Hegazy
Flavonoids biosynthesis
They can be looked at as a C-15 skeleton
(1,3-diphenylpropane) formed of two
benzene rings linked together by a pyran ring
as bridge i.e. C6- C3-C6. One of the benzene
rings is derived from the shikemic acid
pathway (ring B) while the other (ring A) is
derived from the acetate and is formed by
ring closure of a polyketide.
9. Glycosides Dr. Mostafa Hegazy
Classification:
Based on the structure and the oxidation
level of the central pyran ring, they can be
classified into:
Flavones; Isoflavones; Flavonols;
Flavanones; Flavanols; Chalcones; Aurones,
and Anthocyanins (flavylium salts).
10. Glycosides Dr. Mostafa Hegazy
General Properties:
1- Flavonoid glycosides are generally soluble in water and alcohol but insoluble
in chloroform and ether. The aglycones are slightly soluble in water (especially
hydroxylated ones), but soluble in ether.
2- Flavonoids are usually soluble in alcohol with a yellow color which can be
intensified by addition of alkalis. They can be precipitated from their alcoholic
solution by addition of lead salts.
3- Flavonoids are phenolic and hence change in color when treated with base or
ammonia, thus they are easily detected on chromatograms or in solution.
4- Flavonoids contain conjugated aromatic systems and thus show intense
absorption bands in UV and visible regions of the spectrum.
11. Glycosides Dr. Mostafa Hegazy
Isolation:
Two general procedures used for the extraction and isolation of flavonoids:
I- The powdered plant is first defatted, then extracted with alcohol, the alcohol is
evaporated and the remaining aqueous solution is extracted with ether (to take
the aglycones if any), then with ethyl acetate (to take glycosides). The individual
aglycones or glycosides are separated by chromatographic methods.
II- The powdered plant material is defatted, and then extracted with alcohol as
before, the alcoholic extract is freed from the solvent and the obtained residue was
dissolved in water. Lead acetate is added to precipitate the flavonoid. The
obtained precipitate was collected by filtration and then suspended in water and
H2S gas is passed through to precipitate, to liberate the flavonoids which then
can be separated by chromatography.
12. Glycosides Dr. Mostafa Hegazy
Tests for identity:
The flavonoids can be characterized by some color tests, which may also
differentiate between some members of the flavonoids:
1-Alkaline reagents such as KOH, NaOH or NH4OH give yellow color when
added to an aqueous solution of flavonoids.
2-Aluminum chloride flavonoids produce a yellow or green complex with ALCl3.
3- Lead acetate flavonoids with ortho dihydroxy group give a precipitate with
lead acetate.
4- Conc. sulfuric acid produce intense yellow color with flavones and flavonols
may be due to formation of flavylium salts. A deep red to crimson color is
produced with chalcones and aurones may be due to isomerization.
13. Glycosides Dr. Mostafa Hegazy
5- Boric acid flavonoids which contain free OH group at C-5 react with
boric acid in the presence of organic or mineral acids giving bright yellow
complex with green fluorescence.
6- Mg/HCl reduction This is one of the most useful qualitative and
quantitative tests for study of flavonoids. This test differentiates between
the aglycones and glycosides:
Extract + Mg+ + HCl ------ red to violet + isoamyl alcohol ------- if the
colour is removed from the aqueous ------ it is aglycone. ---- if the red
colour is remained in the aqueous ----- it is glycoside.
14. Glycosides Dr. Mostafa Hegazy
Flavone Glycosides
Diosmin:
Diosmin presents in Buchu leaves (Barosma betulina f.
Rutaceae). Diosmin is 5,7,3'-trihydroxy,4‘ methoxyflavone-
7-rhamnoglucoside.
Properties: Diosmin occurs in pale yellow needles or
powder. It is sparingly soluble in pyridine and DMSO. It
dissolves in aqueous KOH solution and in H2SO4
producing a slight fluorescence.
15. Glycosides Dr. Mostafa Hegazy
Uses:
The diuretic action of Buchu leaves is due to
diosmin and also to the volatile oil dioshpenol.
Diosmin has found also wide application in the
Egyptian pharmaceutical market and used for the
treatment of venous disorders
16. Glycosides Dr. Mostafa Hegazy
Apiin:
It is a flavone glycoside present in the fruits and leaves of celery (Apium
graveolens fam. Umbelliferae) and in parsley. It is 5,7,4'-trihydroxy-7-
glucoapioside.
Properties:
Apiin is a colorless flavonoid which dissolves in hot water and hot alcohol but
sparingly soluble in cold water or alcohol. It can not be hydrolyzed by emulsin
or yeast, but upon acid hydrolysis ----- aglycone apigenin + apiose + glucose.
Apiin develops a reddish brown color with FeCl3 and yellow precipitate with
basic lead acetate.
17. Glycosides Dr. Mostafa Hegazy
Flavonol Glycosides
Rutin: It was isolated from Ruta graveolens. The
commercial supply is made from tobacco residues,
sophora and eucalyptus. Rutin is 5,7,3', 4'-
tetrahydroxyflavonol-3-rhamnoglucoside.
Uses and Pharmaceutical Products:
Rutin is used mainly in cases of increased capillary
fragility. Common pharmaceutical products containing
rutin as the major medicine include: Rutin C® Ruta C
60® , Rutin with Vit. C.
18. Glycosides Dr. Mostafa Hegazy
Properties:
Rutin occurs as yellow crystals.
It is slightly soluble in boiling water and alcohol,
insoluble in chloroform, ether and ethyl acetate.
It is also soluble in pyridine and alkalis solutions.
It gives a yellow color when treated with AlCl3.
Rutin reduces ammoniacal silver nitrate but not Fehling's solution.
19. Glycosides Dr. Mostafa Hegazy
Hydrolysis
Acid hydrolysis of rutin ------- glucose +
rhamnose + aglycone called quercetin.
Careful hydrolysis may split one glucose unit
leaving a secondary glycoside called quercetrin.
On the other hand enzymatic hydrolysis splits
the intact disaccharide rutinose (rhamnose +
glucose) and the aglycone quercetin.
20. Glycosides Dr. Mostafa Hegazy
Quercetrin
It is quercetin-3-rhamnoside. This flavonol glycoside is
found in the bark of Quercus tinctoria and Q. trifida.
It was also isolated from many other plant sources.
Properties: Quercetrin is a pale yellow flavonol
glycoside, which is sparingly soluble in water but
shows better solubility, in alcohol. It reduces
ammoniacal silver nitrate but not Feliling 's solution.
On hydrolysis quercitrin ------ rhamnose + quercetin.
21. Glycosides Dr. Mostafa Hegazy
Flavanone Glycosides
Flavanone glycosides are distributed in
some plant families including: Rutaceae,
Rosaceae and Compositae. The
dihydropyrone ring imparts some
unstability to the flavanone and may be
converted to the corresponding chalcons
in alkaline solutions.
22. Glycosides Dr. Mostafa Hegazy
Hesperidin: It is 5,7,3'-trihydroxy-4'-methoxy
flavanone-7-rhamnoglucosidc or it is the 7-
Orutinoside of the aglycone hesperitin, It is
found in rinds of many Citrus fruits. The
substance which was formerly known as
Citrin, was found to be a mixture of
rhamnoglucoside of eriodictyl
(tetrahydroxyflavone ) and methyl eriodictyl
(hesperetin).
23. Glycosides Dr. Mostafa Hegazy
Properties:
White to Faint Yellow color, sparingly soluble in
cold water and alcohol, more readily soluble in
hot water. It is insoluble in ether, benzene and
chloroform Hesperidin can be converted into
hesperidin chalcone by the action of alkali;
hesperidin can be regenerated in acid solution.
24. Glycosides Dr. Mostafa Hegazy
Uses:
Hesperidin increases capillary resistance that
decreases greatly with vitamin C deficiencies.
Hesperidin is necessary for absorption and
retention of vitamin C. So, it is usually used in
combination with vitamin C to reduce capillary
fragility. Hesperidin is
also reported to be of value in the treatment of
influenza (with ascorbic acid).
25. Glycosides Dr. Mostafa Hegazy
Silymarin ( class. as Flavanols or flavonolignans)
Silymarin was isolated from the fruits of the milk
thistle Silybum marianum L. family Compositae,
Silymarin consists mainly of a mixture of
flavonolignans e.g. silybin (the main) , silydianin
and silychristin (Silicristin). Silymarin is produced
through the oxidative combination of taxifolin with
coniferyl alcohol.
26. Glycosides Dr. Mostafa Hegazy
Uses:
generally used in liver dysfunction as it increase the bile
solubility, increase the activity of the antioxidant
enzymes and reduce the fat deposits in liver.
It is used in combination with penicillin in the treatment
of poisoning with the death cap (fungus Amanita
phalloides).
Pharmacological experiments have shown that silymarin
has a protective effect for the liver against the effects of
amatoxins produced by a group of highly toxic fungi of
the genus Amanita.
27. Glycosides Dr. Mostafa Hegazy
Isoflavonoids
Isoflavonoids have been found in many plant
families e.g. Leguminosae and Rosaceae.
The relationship of the structure of isoflavonoids
and diethylstilbosterol is quite evident. This
would explain the estrogenic activity of some
drags bearing isoflavonoids.
Genistein:
Genistein is the aglycone of genistin (7-D-
glucoside) which is obtained from Andira inermis
family Leguminosae. It occurs also in some
Prunus species (fam. Rosaceae).
28. Glycosides Dr. Mostafa Hegazy
Anthocyanins are very numerous and very widely
distributed in the plant kingdom. They are
responsible of the different colors of plant organs.
They occur in the cell sap of flowers, fruits and other
organs, and impart their attractive colors. The color
depends on the pH of the cell sap. Anthocyanidins,
which are the aglycones of anthocyanins, are all
derived from 2-phenyl benzopyrylium or flavylium
cation structure.
29. Glycosides Dr. Mostafa Hegazy
Coumarin Glycosides
This group of glycosides includes coumarin itself,
which has a basic structure of benzo-a-pyrone or
lactone of O-hydroxy cinnamic acid. It may have
additional functional groups (OH, OCH3 or CH3),
attached to the benzene ring. Coumarin and its
derivatives are distributed in several plant families
including: Umbelliferae, Leguminosae (Fabaceae),
Rutaceae, Solanaceae and Asteraceae.
30. Glycosides Dr. Mostafa Hegazy
Uses:
Coumarins and hydroxy coumarins are closely
related to cinnamic and hydroxycinnamic acids, so
it has a flavoring and taste improving properties in
pharmacy as in tobaccos, and food industry.
It is now not used for this purpose as it has been
found to have liver-damaging and carcinogenic
properties. Also it has insecticidal effects.
31. Glycosides Dr. Mostafa Hegazy
Umbelliferone:
Umbelliferone, (7-hydroxy-coumarin), is found in
many plants.
It can be obtained by distillation of the resins of
Umbelliferae (Apiaceae).
It is freely soluble in alcohol, chloroform and
alkalis.
Umbelliferone glucoside occurs in the bark and
wood of Skimmia japonica family Rutaceae.
32. Glycosides Dr. Mostafa Hegazy
Aesculin (6-b-D-glucosyloxy-7-hydroxy coumarin)
It is isolated from the bark and leaves of the horse-
chestnut, Aescullus hippocastanum family
Hippocatanaceae.
Uses:
1-Coumarin derivatives e.g. umbelliferone and aesculin are
employed for protection from sun-light, as they absorb
short-UV radiation (280-310 nm) which is harmful to skin,
and transmit the long-UV radiation (315-400 nm), which
give the brown suntan. So, coumarins are used in suntan
preparations.
2-Umbelliferone is used in brain intercellular pH
measurements and in fluorescent immunoassays.
33. Glycosides Dr. Mostafa Hegazy
Vanilloside (glucovanillin)
occurrence: vanilla pods.
Vanilla is the fully-grown but unripe fruit of Vanilla planfolia
fam. Orchidaceae, which has been subjected to a
fermentation process. Green vanilla contains vanilloside
and vanilloloside (vanillyl alcohol glucoside).
1- Glucovanillin is an odorless glucoside. During curing
(fermentation) these glycosides subjected to an oxidizing
and a hydrolyzing enzymes (which present in the plant
tissues) and vanillin with its characteristic odour is set free.
2- Glucovanillin is an aldehydic and a phenolic glucoside.
34. Glycosides Dr. Mostafa Hegazy
Uses:
for the production of vanillin that is used in
confectionery and in perfume; it has been
replaced by vanillin obtained by
biotransformation or chemical synthesis.
35. Glycosides Dr. Mostafa Hegazy
Cyanogenetic, cyanogenic or cyanophore
glycosides
produce the toxic gas HCN (prussic acid or hydrogen
cyanide) as a result of enzymatic hydrolysis.
Amygdalin
found in bitter almond (Prunus amygdalus var.amara
family Rosaceae) , in the kernel of apricot, cherries,
peaches and plums.
36. Glycosides Dr. Mostafa Hegazy
Isolation:
The fixed oil is expresses from the bitter almond seeds, and
then cake is extracted with alcohol (95%). The alcoholic
extract is concentrated and a large volume of ether is
added, where Amygdaline is insoluble in ether, so it will
crystallize out.
Uses:
Bitter almond and bitter almond oil are used as spices, but
this use is not entirely safe because of the hydrogen cyanide
content.
37. Glycosides Dr. Mostafa Hegazy
Hydrolysis:
1- by acid hydrolysis to give two
molecules of glucose and
mandelonitrile.
2- Almond seeds contain emulsin
which is a mixture of enzymes, of
which amygdalase which hydrolyze
amygdalin into prunasin, which in turn
hydrolyzed by prunase into
mandelonitrile, which hydrolyzed by
hydroxynitrile lyase
(hydroxynitrilase) into benzaldehyde.
38. Glycosides Dr. Mostafa Hegazy
Prunasin: a cyanogenetic
glycoside obtained from
1- Wild cherry bark (Prunus
serotina, family Rosaceae).
2- By the partial hydrolysis of
amygdalin.
39. Glycosides Dr. Mostafa Hegazy
Linamarin
A cyanogenetic glycoside of the aliphatic type. It occurs
in linseed (Linum usitatissimum, family Linaceae).
Hydrolysis: On hydrolysis linamarin produces glucose
and acetone cyanhydrine. Further degradation gives
acetone and hydrocyanic acid.
Purification of linseed oil from HCN:
1- By boiling the fixed oil and 2- passing super-heated
steam through the oil to remove any traces of HCN.
40. Glycosides Dr. Mostafa Hegazy
Detection of Cyanogentic glycosides:
crushed pieces in a tube + H2O cover with
sodium picrate paper, put in water bath for 1h.
the yellow color of the sodium picrate paper color
will change into brick red color due to liberation
of HCN and reduction of sodium picrate to sodium
picramate.
41. Glycosides Dr. Mostafa Hegazy
Thio-Glycosides (glucosinolates, sulfur containing glycosides or
S-glycosides)
Thioqlycosides are a group of compounds that yield upon
hydrolysis sulphurated aglycones (often with acrid volatile
flavors).
The sugar part is always β-D-1-glucopyranosyl residue, which is
linked to the aglycone via a sulpher atom.
The appropriate hydrolytic enzyme, a thioglucosidase known as
myrosinase, always accompanies glucosinolates.
42. Glycosides Dr. Mostafa Hegazy
Sinigrin
Occurrence: seeds of black mustard (Brassica nigra family Cruciferae).
Black mustard seed contains myrosin enzyme and when macerated with water it
yields volatile oil (90% of which is allylisothiocyanate).
Preparation of sinigrin:
The crushed defatted seeds are treated with boiling alcohol …?. Most of the fixed
oil is removed by expressing the marc while hot and sinigrin is extracted by
maceration with cold water. The aqueous extract is then treated with mild alkali
(BaCO3) to neutralize
any free acidity and concentrated to a syrupy liquid. the aqueous extract is boiled
with alcohol 95%....? and the alcoholic extract is filtered from the precipitated
mucilage and cooled when
sinigrin crystallizes out.
43. Glycosides Dr. Mostafa Hegazy
Hydrolysis of sinigrin:
Sinigrin can be hydrolyzed by myrosin into allylisothiocyanate, glucose and
potassium hydrogen sulfate.
44. Glycosides Dr. Mostafa Hegazy
Sinalbin white mustard seed (Sinapis alba).
Hydrolysis: Upon hydrolysis of sinalbin with
myrosinase, it yields P. hydroxybenzyl
isothiocyanate, sinapine hydrogen sulfate and
glucose. The P-hydroxybenzyl isothiocyanate (acrinyl
isothiocyanate) is an oily liquid having a pungent
taste and rubefacient properties but, owing to its slight
volatility, it lacks the pungent odor of
allylisothiocyanate (c.f black mustard). Sinapine
hydrogen sulfate is the salt of an unstable quaternary
alkaloid and is hydrolyzed by KOH to yield sinapic
acid and choline.
45. Glycosides Dr. Mostafa Hegazy
Uses: as a plasters as rubefacients and counter irritants. condiments . In large
doses as emetic. It should be noted that many glucosinolates have an antithyroid
and goiter inducing effect in man.