Plant bitters and sweeteners

Plant bitters and sweeteners

1. Arpit Rajaram Suralkar M Pharmacy (Quality Assurance) 1

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3. 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. Sucrose sets gold standard for sweet taste as it’s taste is quick, short lived and clear and also abundantly available in nature It imparts viscosity to drug and also even act as preservative for liquid dosage form It is nutritive too 3

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5. Compatible sweetness even in low concentration. cheap and easily available agreeable odour Stability- heat stable, non hygroscopic non toxic inert Easy to handle in formulation- water solubility, dissolution rate, etc 5

6. CLASSIFICATION OF sweetenerES Nutritive Sweeteners Non Nutritive sweeteners 6

7. Alternative nutritive sweeteners are sugar alcohol such as Sorbitol, Mannitol, Lacitol etc. It is having properties like less sweet and less calories FRUCTOSE- 4Kcal/gm the same as sucrose and it doesn't cause fluctuation in blood sugar, thus better choice for diabetic patients. 1.5 times sweeter than sugar and cost effective for food industry. Still ideal alternative for sugar does not exist????? 7

8. Mostly are artificial* Examples include Aspartame, Saccahrin, Clycamate, Alitame etc. More sweet and thus only small quantity is required for sweetening food preparation. 8

9. Sweetness potency= 9 E.g. 0.75 gm/litre solution of aspartame matches with the sweetness of 100 gm/litre solution of sucrose. Therefore aspartame is considered as 133 times sweeter than sucrose.

10.  The sweetness potency is also dependant on taster, the pH, the viscosity of formulation, etc 10

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12. 12 SWEETNERS FROM NATURAL ORIGIN Stevioside Glycyrrhizin Neohesperidin Dihydrochalcone Thaumatin Monellins Sucralose Sorbitol

13. Source: It is Steviol glycoside obtained from leaves of the Stevia rebaudiana Berrtoni Family: Compositeae. G.S.-paraguay, Brazil, Japan, China, Taiwan, Thailand, Malaysia. 13

14.  Properties : 14 It is 160- 170 times sweeter than sucrose. It is heat stable and pH stable and do not ferment. It does not induce a glycemic response. Natural sweetener to diabetics and carbohydrate controlling diets. 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 tainted with a bitter and undesirable after taste. No side effects. Both are diterpene Glycosides .

15.  Structure: It is made up from a diterpene known as Steviol . Stevioside is formed by attaching glucose molecules to the steviol structure. 15

16.  Preparation : the leaves are extracted with water/ water ethanol mix and further purified by treatment with CaOH 2 /MgOH 2 / carbonate. The ratio of rebaudioside to stevioside can be increased by using methanol for extraction of leaves  Rebaudioside A is approximately one third higher than stevioside and tastes better. But it is unstable and gets decopmosed to light. 16

17.  Uses- as Sweetning agent as table top sweetner, in confectioneries, soft drinks and fruit products. 17 DISADVANTAGE: Steviol has been reported to be mutagenic.

18. Biological Source : It is a mixed Ca & K salt of Glycyrrhizic acid found in Glycyrrhiza glabra Family : Leguminosae Characteristics : Glycirrhizin is 50x-100x sweeter than Sucrose Ammonium Glycyrrhizinate is 50x sweeter than sucrose and its salt are characterized by a delayed sweetness onset and characteristic liquorice taste  more like flavouring agent than sweetener 18

19. Preparation: A crude extract of liquorice root is to be prepared with the help of counter current extraction with water. After removal of polysaccharide, Glycyrrizin can be precipitated from crude extract with sulphuric acid. Ammonium glycirrhizinate is prepared by treatment with NH3, followed by subssquent drying and precipitation with ethanol. 19

20.  Chemical Constituents : Chemical Constituents :-It is a triterpenoids glycoside glycirrhizin. H2O Glycyrrhizic acid ---------> Glycyrrhetic acid (aglycone)+ 2 molecules of glucuronic acid The acid form is not particularly water-soluble, but its ammonium salt is soluble in water at PH greater than 4.5. It also contain liquirtin and liquiritigenin(flavonoid glycoside). Glycyrrhizic acid is a triterpenic glycoside of β-Amyrin type which contains two β-1,2 Glycosidic linked Glucoronic acid. 20

21. As flavoring agent and as flavor enhancing effect in food products. In the treatment of peptic ulcers and as an expectorant, produce anti-inflammatory effects, is used in the treatment of chronic hepatitis and cirrhosis. 21

22.  Causes Oedema and Hypertension. So, its dose should be 200 mg per day or less. 22

23. Biological source: It is a flavonoid compound present in the bitter orange Citrus aurantium Var amara Family : Rutaceae Characteristics: 330x >> Sucrose It is characterized by pronounced Menthol like after taste which limits its use. It act synergistically with a number of other sweeteners. It has flavor enhancing system. 23

24.  Preparation: It is prepared from neohesperidin by hydration of neohesperidin under alkaline condition. 24

25. Use : It is used in confectionery, chewing gum, beverages and dairy products 25

26. Source: -It is obtained from the arils of fruits of Thaumatococcus danielli Family:- Marantaceae. Properties: It is approximately 3500 times sweeter than sucrose The sweetness shows delayed onset and long persistent taste. It loses its sweetness on heating. It is highly water soluble, stable below Ph 5.5. 26

27. Chemical Constituent:-It is a polypeptide containing Thaumatin I & Thaumatin II as major components. Preparation: It is extracted with water and then purified by Ion exchange chromatography. Use: It is used as flavor enhancer rather than as a sweetener. It is used as flavor enhancer in confectionary, chewing gum and similar products. 27

28.  The sweetness of thaumatin shows delayed onset and long persistent liquorices like taste. 28  It loses its sweetness on heating or splitting disulphide bridge

29. Biological source: It is intensely sweet polypeptide constituent present in the fruits of tropical plant Dioscoreophyllum cumminsii Stapf Diels (serendipity berry) Family: Menispermaceae Characteristicc: 2000x >> Sucrose Sweetness of the polypeptide Monellin is sensitive to conformational changes caused by heat or hydrolytic decomposition, so rendering it unsuitable as normal sweetener. 29

30. It is semisythetic sweetener Based on discovery- halogenation increases sweetness of carbohydrates It is trichlorogalctosucralose 30

31. It solubale in water and ethanol It is 600x >> sucrose Sweeteness is slightly delayed but persistant for long time International authority limits its use* Evidence of benefit is lacking for long- term weight loss with some data supporting weight gain and heart disease risks. 31

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33. Are 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. Bitters increases the appetite and stimulates digestion by acting on the mucous membranes of the mouth. It also increases the flow of bile, stimulate repair of gut wall lining and regulate the secretion of insulin and glucagons. They stimulate the gustatory nerves and increase the psychic secretion of gastric juices. These are also used as anti-tumour and anti-malarial agents 32 33

34.  Some of the bitters belong to alkaloids 34 7/11/2018  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 monoterpenoids with pyran cyclopentane ring.

35.  Geranyl phosphate I r ido i d 35 7/11/2018

36. Its is the reciprocal of the dilution of a compound, a liquid or an extract that still has a bitter taste. It is determined by comparison with quinine hydrochloride, the bitterness value of which is set at 2,00,000. Brucin can also be used as standard for bitterness Amirogentin present in Gentian is considered bittermost substance 36 7/11/2018

37.  Synonyms: Yellow Gentian, Gall weed, Bitter wart, Radix Gentianae. 37 Biological Source: It consist of dried rhizome and roots of Gentiana lutea Linn. Family : Gentianaceae. CHEMICAL CONSTITUENTS: It consist of the bitter glycoside GENTIOPICRIN as active constituent. › Other bitter compounds are Genticin, Amaropanin, Amarogentin & Amaoswerin. › It also contains Gentiin, Gentiamarin, Gentisic acid, Tannins, Pectin and calcium oxalates. 7/11/2018

38.  USES: Potent stomachic and treats GI problems like indigestion. 38 7/11/2018 › Emmenogoggue (enhance menstrual flow) › This bitter stem less is used to treat wounds. › To treat arthritis, sore throat, Jaundice › Gentian extract are used in variety of foods and cosmetics. Contra indications: Avoided in pregnancy and lactation. Contra indicated in gastric and duodenal ulcers. Adverse effects: Raw extract may cause nausea, vomiting and diarrhea.

39.  Synonyms: Andrographis Paniculata, Kalmegh 39 7/11/2018 Biological cource: The drug consist of dried or fresh leaves and aerial portion of the plants Andrographis paniculata Nees. Family: Acanthaceae. Chemical Constituents • It contains a bitter compound andrographolide up to 1 % › It is diterpene lactone. › Some other compounds such as neoandrographolide, andrographosterol, andrographiside, flavonoids, phenolic compounds and some waxy material are present.

40.  Uses: It is used as bitter tonic and stomachic. 40 7/11/2018 › It also known as “green chiretta” in India. › It is used in the treatment of torpid liver (impaired nerve impulses) and jaundice. › The decoction of the plant is used as blood purifier. › The decoction of the leaves is given with spices such as cardamom, clove or cinnamon for stomach ailment in infants. › It produce enzyme induction.

41. Synonyms: Chiretta, Chirayta, Bitter stick Biological source: It consist of the dried entire herb of Swertia chirata 41 Family: Gentianaceae Chemical Constituents: It contains bitter glycosides amrogentin 0.04 % and amroswerin 0.03%. › The other two extremely bitter principles ie chiratin and ophelic acid also present in crude drug. Other compound include chiratol, mangiferin, swertianin, chiratanin, chiratenol. Uses: It is used as bitter tonic and stomachic. › It is also used as antimalarial in some part of India. 7/11/2018

42. Synonyms: Picrorhiza, Kutki Biological source: It consist of dried rhizomes and roots of Picrorhiza kurroa Royle. Family: Scrophularelareaceae Chemical constituents: It contains cyclopentanopyran monoterpenoids, a class of glycosides . It contains picroside I, Picroside II and kutkoside up to 3-4 % . drug also contains about 9 % cathartic acid. Uses : It is used as bitter tonic and stomachic. It is also used as laxatives in small doses and cathartic ( produce psychological relief) in large doses. It is used as hepatoprotective in Jaundice. It is also used as liver tonic. 42 7/11/2018

43. SYNONYM :- Bitter wood, Jamaica Quassia BIOLOGICAL SOURCE :- It consists of the dried stem wood of Picrasma excelsa Family Simarubaceae CHEMICAL CONSTITUENTS :- It contains about 0.2% of the bitter lactone i.e. quassin & its hemiacetal Neoquassin . USES :- Bitter tonic , It is given as an enema in the form of infusion to expel threadworms , It possesses insecticidal properties. 43 7/11/2018

44. SYNONYM :- Gudmar , Madhunashini BIOLOGICAL SOURCE :- It consists of the leaves of a perennial woody climber plant known as Gymnema sylvestre Family Asclepiadaceae . CHEMICAL CONSTITUENTS :- It contains pentriacontae , hentriacontane , phytin , α & β chlorophylls. Gymnemic acids (anti-sweet compounds), the mixture of triterpene saponins & antraquinone derivatives. USES :- Stomachic, stimulant, laxative & diuretic. Antidiabetic due to indirect stimulation of insulin secretion from pancreas. 44 7/11/2018

45. SYNONYM :- Egyptian privet, Lawsonia -alba BIOLOGICAL SOURCE :- It consists of fresh or dried leaves of the plant Lawsonia – inermis Family: Lythraceae . 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 45 7/11/2018

46.  Other examples- Nux vomica, Karela, Methi, etc… 46 7/11/2018

47. Pharmacognosy and phytochemistry by Rangari part II Pharmacognosy and phytochemistry by Gokhale, Kokate, Purohit 47