Anthraquinone Glycosides

This slide contains sources, collection process, constituents and uses of some important plants for making medicine containing anthraquinone glycosides like Senna, Cascara Sagrada, Aloe, Rhubarb, Chrysarobin.

1. Anthraquinone Glycosides

2. 1 2 3 4 Sources : Botanical and geographical Collection Constituents Uses

3. Anthraquinone Glycosides Anthraquinone are glycosides which possess anthracene or their derivatives as aglycone in which two kept keto group are attached with the benzene ring. Anthraquinone also anthracenedione or dioxoanthracene is ar aromatic compound. Several isomers are possible.

4. Anthranone : Reduced anthraquinone derivatives and keto group is attached with the benzene ring. Found in free or combined form Can converted to other compounds in solution Contains significant therapeutic action of the crude drug Anthranole : Reduced anthraquinine derivatives in which a hydroxyl group is attached with the benzene ring Found in free or combined form Contains significant therapeutic action of the crude drug Oxanthrone : Intermediate products between anthraquinone and anthranols Present in Cascara Sagrada bark Produce anthraquinone on oxidation

5. Hydrolysis: Chemical test of anthraquinone : Borntrager’s test Modified Borntrager’s test

6. Uses Stimulant cathartics Aglycone in free state shows little therapeutic activity Glycone helps in absorption and transportation of aglycone in large intestine Dyestuff precursor Digester additive in papermaking In the production of hydrogenperoxide

7. Cascara Sagrada

8. Botanical Source: Dried bark of Rhamnus purshianus . (Family- Rhamnaceae ) Geographical sources: Native – Pacific coast of North America Commercial supplies- Oregon, Washington, Southern British Columbia Collection: Bark is stripped from the tree Bark is sun dried Broken into small pieces and keep into bags Keep for one years before use Branch of Cascara Sagrada tree Bark of cascara

9. Glycosides O- Glycosides- 10-20% C- Glycosides- 80-90% (Based on emodin) ( Aloin like compounds) They are both O and C- Glycosides

10. Aglycone Unit Emodin , Iso - emodin , Aloe emodin , Methyl- hydrocotoin , Chrysophanic acid Emodin Glycone Unit Rhamnose and Glucose ratio is 1:1

11. Uses The hydroxyanthracene glycosides act as a stimulant laxative by exciting peristalsis in the colon. Emodin of bark may have anti-cancer effects. The food industry sometimes uses cascara as a flavoring agent for liquors, soft drinks, ice cream, and baked goods Has anti ageing properties Hydrating properties Prevents hair problems Caution: High doses can causes diarrhea Pregnant and lactating women are advised not to use Regular use can make you addict of the herb Prolonged use may cause brownish yellow urine

12. Aloe

13. Botanical Sources: Dried latex of leaves of following plants Aloe barbadensis or Aloe vera (Curacao Aloe) Alo ferox , Aloe Africana, Aloe spicata (Cape Aloe) Family- Liliaceae Aloe hereroionsis Aloe Africana Aloe ferox

14. GEOGRAFICAL SOURCE: Curacao Aloe: Aloe barbadensis is a native of northern africa Cape Aloe: Cape Aloe is found in US , Venezuela,Haiti & South Africa Collection: Leaves are cut in March and april Placed cut-end downward in a V-shaped vessel Allowed to harden Hard , bitter tasted latex is collected then

15. Chemical constituents: Curacao Aloe Isobarbaloin Free aloe- emodin Free and combine anthranol Chrysophanic acid Anthranol

16. 2 . Cape Aloe Barbaloin 5-30% Socaloin 7.5-10% also volatile oil and resinous yellow aloin is present . Aloin

17. Uses 1. Aloe perryi,Aloe ferox,aloe babadensis are used as natural flavoring agent in USA. 2. It acts as purgative or laxative mainly unprocessed aloe.Also some drugs are made up of aloe constituents which acts as colon cleanser. 3. it has healing power so used in the treatment of burns and other skin problems. 4. Used hugely in cosmetic products 5. Also some people use this plants as ornamental or decorative plants because of their nice color and shape. 6. According to Cancer Research UK, a potentially deadly product called T-UP is made of concentrated aloe, and promoted as a cancer cure. They say "there is currently no evidence that aloe products can help to prevent or treat cancer in humans"

18. Interactions: 1. We cant intake aloe along with Lanoxin drug as it increases the side effects of lanoxin because aloe is stimulant laxative and decreases the potassium level which aggravates the side effects of this drug.The latex of aloe decreases some drugs activity. 2.We should avoid aloe while taking antidiabetes drugs because both decreases the blood sugar level. 3. Taking aloe before surgery can cause increased bleeding as it has anti blood clotting property.

19. Rhubarb

20. Botanical Sources: Dried roots and rhizomes of Rheum officinale Rheum palmatum Rheum emodi (Indian or Himalayan) Rheum webbianum (Indian or Himalayan) Family- Polygonaceae Geographical sources: Native- China for Chinese Rhubarb and India, Pakistan,Nepal for Indian Rhubarb

21. Rheum officinale Rheum palmatum Rheum emodi Rheum webbianum

22. Collection: Rhizomes are collected in Autumn Peeled and perforated, strung on rope Dried in sun or artificial heat Growing Rhubarb in raised beds Growing Rhubarb in Greenhouse

23. Chemical Constituens : Glycosides of Rhein anthrones Anthraquinones - Rhein , Chrysophanol , Emodin , Aloe emodin , Emodin monomethyl ether Gallic acid, Catechin , Calcium oxalate (7%) Emodin

24. Uses Used as cathartic Astringent Mouthwash for oral ulcer Treat burns, wounds Fibers obtained from rhubarb can be used for the manufacture of paper Used for dyeing of hair.

25. Anything interesting?? R hubarb- “a heated argument or dispute” The leaves attached to the Rhubarb stalk are poisonous. It repel insects! One of its most popular applications….. Pie! Fruit??? Or Vegetable??? Rhubarb enhances the appetite. The impact of the rhubarb depends on how it is prepared. More recently there have been claims that rhubarb can be useful in treatment of Hepatitis B. One of the first medicines to be imported from china to the West

26. Senna

27. Botanical Sources: Dried leaflet of Cassia acutifolia (Alexandria Senna ) Cassia angustifolia ( Tinnevelly Senna ) Family- Leguminosae Geographical Sources: Cassia acutifolia grows near the Nile Aswan to Kordofan Cassia angutifolia grows wild in Somalia, Arabian Peninsula and India Cultivation: Harvested in April and September Cut off the tops of the plants about 15 cm above the ground Dried in the sun Stems and pods are separated from leaflets Leaves are graded and baled or packed in bags Cultivation of Senna

28. Chemical Constituents: 1. Glycosides- Sennoside A and B whose aglycone is rhein dianthrone . 2.Sennosoids C and D whose aglycone is composed of one molecule of rhein and one molecule of aloe- emodin . 3. Monomeric glycosides and Free anthraquinones 4. Senna pod contains active glycosides

29. Uses Cathartic It is safe for shorter period in case of pregnancy or breast feeding Treat irritable bowel syndrome Treat skin disorders Clean the system of worms Purgative

30. Chrysarobin

31. Botanical Sources: It is a mixture of neutral principles obtained from Goa powder which is obtained from Lysogenous cavities in the wood of Andira araroba . Family- Leguminosae . Geographical sources: Portuguese colon on the Malabar Coast of India. Chemical Constituents: Chrysophanol anthrone (30-40%) Emodin anthrone monomethyl ether (20%) Dehydro emodin anthrone monomethyl ether (30%) Chrysophanol Anthrone

32. Properties: Commercial product Brownish to orange-yellow Microcrystalline Odorless Tasteless powder Irritating to mucous membranes Causes dangerous inflammation if it enters the eye