Plant bitters and sweeters

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PRESENTATION ON Plant bitters & SWEETNERS

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Plant bitters Bitters are the edible natural products mostly consumed before any normal meals to stimulate as well as enhance the appetite. However, the bitter glycoside as a class do possess almost similar activities like the bitters such as : digestive, stomachic and febrifuge. These are not confined to the same chemical class, but the most important ones amongst them contain the glycosides of monoterpenes iridoids with pyran cyclo pentane ring. Monoterpenes : These are derived from C10 geranyl phosphate and constitute important components of volatile oils. Iridoids : These are cyclopentan -(C) – pyran monoterpenoids .

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BITTERNESS VALUE :- It is obtained organoleptically by comparison with a quinine hydrochloride solution which acts as the standard. BITTER principles :- These are hetrogenous vegetative compounds that neither belong to the class of alkaloids nor to the glycosides, but they do possess a characteristic bitter taste. It is however pertinent to observe that bitter principles are invariably of vegetative origin and essentially comprise of C, H & O but are found to be free from N. These are also used as anti- tumour & anti-malarial agents.

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Classification of bitter principles Phenolic Bitter Principles Lactone Bitter Principles Chromone Bitter Principles Coumarin Bitter Principles Coumarone Bitter Principles Miscellaneous

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Phenolic Bitter Principles The crystalline acidic bitter principles having a phenolic function are found in naturally occuring plant sources such as : Humulon Lupulon Biological Source :- They are obtained as an antibiotic constituent from the strobiles of Humulus lupulus L., belonging to natural order Moraceae . Uses :- Exerts bacteriostatic action. Contributes to the bitterness of Hops extract used in making beer.

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Lactone Bitter Principles They essentially possess a 5 membered lactone ring. Eg . α - Santonin and Picrotoxin . Biological Source :- α - Santonin is obtained from the dried unexpanded flower heads of Artemisia maritimia L., Compositae . Uses :- It is mostly used as an anthelmintic (nematodes)

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Chromone , Coumarin & Coumarone Bitter Principles These heterocyclic moieties are derived from γ - pyrone , α - pyron & furan nucleus respectively in combination with a benzene nucleus.

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Chromone Bitter Principles Eg . Khellin , Khellol Glucoside and Visnagin . Biological Source :- These are obtained from the seeds of Ammi visnaga , L. family- Umbelliferae . Uses :- As a potent Vasodilator. Potent selective bronchodilator.

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Coumarin Bitter Principles Eg . Angelicin , Pimpinellin , Psoralen , Methoxsalen , Bergapten & Imperatorin . ANGELICIN Biological Source :- Angelicin occurs in fruit or roots of Angelica archangelica L., Family Umbelliferae . Uses :- It is useful for Enteritis, Flatulance , Gastritis, Rheumatism and Ulcers.

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PIMPINELLIN Biological Source :- It occurs in the fruits and rhizomes of Pimpinellin saxifraga L., family – Umbelliferae .

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Coumarone Bitter Principles Rotenone Synonym :- Canex Biological Source :- The principal insecticidal constituent of the dried derris roots, Derris elliptical Roxb .and D.malaccensis Prain , family Leguminosae . Uses :- Mostly used as a potent pesticide. Widely employed as an acaricide and actoparasiticide in cattles .

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Miscellaneous Bitter Principles :- Examples includes :- Picrotoxin Quassin Lactucin Erythrocentuarin Gentisin Cantharidin

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DRUGS CONTAINING BITTER GLYCOSIDES ARE :- GENTIAN PICRORRHIZA CHIRATA QUASSIA KALMEGH GYMNEMA HENNA

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GENTIAN SYNONYMS :- GENTIAN ROOT, GENTIANA, RADIX GENTIANAE BIOLOGICAL SOURCE :- It is the dried partially fermented rhizome and root of yellow Gentian i.e. Gentiana lutea , family Gentianacae . MACROSCOPY :- COLOUR - Yellowish-Brown ODOUR - Peculiar TASTE - Initially gives a sweet taste followed by intensely bitter taste. SHAPE - The fracture is short and smooth in dried drug , but tough and flexible in moist drug. CHEMICAL CONSTITUENTS :- 1. It contains bitter glycosides mainly Gentiopicrin 2. Amarogentin 3. Gentianin 4. Gentisin , gives yellow colour to drug. 5. It also contains polysaccharides.

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USES :- As a bitter tonic.

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picrorrhiza SYNONYM :- Indian Gentian, Kutki BIOLOGICAL SOURCE :- It consists of dried rhizomes of the plant Picrorrhiza kurroa , family Scrophulariaceae . MACROSCOPY :- COLOUR – Deep greyish brown in colour , externally white, blackish internally with whitish wood. ODOUR - Slight and unpleasant. TASTE - Bitter SHAPE - Cylindrical pieces with longitudinal wrinkles and annulations at the tip. CHEMICAL CONSTITUENTS :- It contains irridoid bitter substances, Picroside 1, Picroside 2, and kutkoside .

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USES :- Bitter tonic, febrifuge and stomachic. Laxative in large doses. Used in treatment of jaundice.

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QUASSIA SYNONYM :- Bitter wood, Jamaica Quassia BIOLOGICAL SOURCE :- It consists of the dried stem wood of Picrasma excelsa , Planchon , family Simarubaceae . It contains about 0.2% of the bitter lactone i.e. quassin & its hemiacetal Neoquassin . MACROSCOPY :- The wood has a bitter taste Odourless It is a diffuse porous wood and the vessels are present in group. CHEMICAL CONSTITUENTS :- It contains Amaroid Compounds like Quassin , Neoquassin , Isoquassin etc.

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USES :- 1. Bitter tonic 2. It is given as an enema in the form of infusion to expel threadworms. 3. It possesses insecticidal properties.

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GYMNEMA SYNONYM :- Gudmar , Madhunashini BIOLOGICAL SOURCE :- It consists of the leaves of a perennial woody climber plant known as Gymnema sylvestre , family Asclepiadaceae . MACROSCOPY :- COLOUR - Green ODOUR - Pleasant and aromatic TASTE - Tasteless SHAPE - Elliptic or ovate with acute or acuminate apex EXTRA - The leaves when chewed have remarkable property of paralysing the taste glands for few hours against sweet and bitter taste. CHEMICAL CONSTITUENTS :- It contains pentriacontae , hentriacontane , phytin , α & β chlorophylls. Gymnemic acids (anti-sweet compounds), the mixture of triterpene saponins & antraquinone derivatives.

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USES :- Stomachic, stimulant, laxative & diuretic. Antidiabetic due to indirect stimulation of insulin secretion from pancreas.

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henna SYNONYM :- Egyptian privet, Lawsonia -alba BIOLOGICAL SOURCE :- It consists of fresh or dried leaves of the plant Lawsonia – inermis Lam. , family Lythraceae . MACROSCOPY :- COLOUR - Greenish-Brown ODOUR - Characteristic TASTE - Bitter and astringent CHEMICAL CONSTITUENT :- It contains lawsone (0.5-1%). Lawsone , the main colouring constituent is said to be a degradation product of primary glycoside hennoside A,B,&C. USES :- It is used as hair dye It shows Anti-bacterial and anti-fungal property.

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NATURAL PLANT SWEETENERS Sweetening agents are the substances which are added to a drug formulation to mask its bitter taste. Sugar is the most widely used natural sweetening agents. It imparts a sweet taste i.e. quick, clean and short lived. It imparts viscosity to drugs and also even act as a preservative for liquid dosage form. It is easily metabolized yielding an energy of 4 Kcal/gm.

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TYPES :- Nutritive Sweeteners :- a. Alternative nutritive sweeteners are sugar alcohol such as Sorbitol , Mannitol , Xylitol , Lactilol , or a mixture of Glucosyl-Sorbitol and Glucosyl Mannitol . b. less sweet and less caloric. c. FRUCTOSE- 4 Kcal/gm the same as sucrose and it does not cause fluctuation in blood sugar, thus better choice for diabetic patients. d. 1.5 times sweetener than sugar and cost effective for food industry.

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2. Non- Nutritive Synthetic Sweetener :- a. Examples include Aspartame, Saccahrin , Cylcamate , Acesulfane -K, and Alitame . b. More Sweetener and thus only small quantity is required for sweetening food preparations.

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Sweeteness POTENCY SWEETNESS POTENCY = SWEETNESS OF 100 gm/ Lt SUCROSE SOLUTION g/Lt of SWEETENER SOLUTION WITH EQUIVALENT SWEETENESS For Eg , 0.75 gm/Lt of Aspartame matches with the sweetness of a 100 gm/Lt of Sucrose solution. Therefore, Aspartame is considered as 133(133X) sweeter than sucrose. An ideal alternative sweetener should have safety along with sweeteness , stability with other food ingredients, higher water solubility, dissolution rate etc.

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Chemical structures Of sweetenrs

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Various sweeteners of Natural Origin :- Stevioside and Rebaudioside Glycyrrhizin Neohesperidin Dihydrochalcone Thaumatin Monellins Sucralose Sorbitol

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Stevioside and Rebaudioside Biological Source :- It is extracted from a SOUTH AMERICAN Plant Stevia rebaudiana Berrtoni family Compositae . Characteristics :- The dried leaves of the plant, the water extract of the leaves and the purified ingredients of extract are used as sweetening agents. It’s sweetness is tainted with a bitter and undesirable after taste. (160X-170X) >> Sucrose No side effects. Both are D iterpane Glycosides . Sweeteness intensity of Rebaudioside A >> 1/3rd higher than that of Stevioside and it’s taste characteristics are also superior but it is unstable.

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Disadvantage :- 1. But Stevioside & Rebaudioside A gives rise to its principal metabolite, Steviol which has been reported to be mutagenic.

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Glycyrrhizin Biological Source :- It is a mixed Ca & K – Salt of Glycyrrhizic acid found in Glycyrrhiza glabra L., LEGUMINOSAE. Characteristics :- (50X-100X) >> Sucrose Ammonium Glycyrrhizinate is 50X sweeter than sucrose and its salts are characterised by a delayed sweeteness onset, a lingering sweeteness with a characteristic liquorice taste. Chemical Constituents :- Glycyrrhizic acid is a triterpenic glycoside of β - Amyrin type which contains two β -1,2 Glycosidic linked Glucoronic acid. H 2 O Glycyrrhizic acid Glycyrrhetic acid ( aglycone ) Ammoniated salt of Glycyrrhizic acid improves the solubility of Glycyrrhizic acid in water.

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USES :- As a flavouring agent and as a flavour enhancing effect in food products. DISADVANTAGES :- Causes Oedema and Hypertension. So, its dose should be 200 mg per day or less in drug formulation.

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Neohesperidin Dihydrochalcone :- Biological Source :- It is a flavonoid compound present in the bitter orange Citrus aurantium Var amara , Rutacea . CHARACTERISTIC :- (330X) >> Sucrose It is characterized by a pronounced Menthol like after taste which limits its use. It acts synergistically with a number of other sweetners . It has a flavour enhancing System.

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Thaumatin Synonym :- Talin Biological Source :- It is a basic protein found in the arils of the fruits of the tropical plant Thaumatococcus danielli , Benth , family Marantaceae . Characteristic :- 1. Highly soluble in water. (3500X) >> Sucrose It’s sweetness shows a delayed onset and long persistent liquorice like taste.

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Chemical Const. :- It consists of structurally related poly-peptides and thaumatin-1 & thaumatin-2 are the major components. Uses :- As a flavour enhancing agent rather than as a sweetener. Disadvantages :- It’s temporal sweetness characteristics don’t favor its use as a single sweetener.

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Monellins Biological Source :- It is an intensely sweet polypeptide constituent present in the fruits of tropical plant Dioscoreophyllum cumminsii Stapf Diels, Menispermaceae . Characteristics :- (2000X) >> Sucrose Sweetness of the polypeptide Monellin is sensitive to conformational changes, so rendering it unsuitable as a normal sweetner .

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Sucralose Biological Source :- 1.It is a semi-synthetic sweetner developed by the British Sugar Company Tate and Lyle in 1976. 2. Chemically, Disaccharide 1’,6’- dichloro-1’,6 dideoxy - β -D fructofuranosyl 4-chloro-4-deoxy- α -D- galactopyranoside which is referred to as Trichlorogalactosucrose . Characteristics :- Soluble in water and ethyl alchol . (600X) >> Sucrose The sweetness is perceived with a slight delay but persists for a longer time. Halogenation increases the sweetness of Carbohydrates substantially. Disadvantages :- Not approved by International Authorities.

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