Medicinal plants and medical plant materials that contain anthracene derivatives

1. Medicinal plants and medical plant materials that contain anthracene derivatives

2. Anthracene derivatives are organic compounds containing the 9,10-anthracenedione nucleus of different oxidation levels, types of connection and condensation of monomer structures. The general formula is С6-С2-С6. Anthracene Anthraquinone

3. The oxidation level of the medium ring can be different- to anthranol, anthrone, oxanthrone and anthraquinone. Anthranols, anthrones and oxanthrone are easily oxydate even by oxygen in the air thus the most spreaded and studied are anthraquinone derivatives.

4. Classification Monomers – anthracene derivatives with one anthracene molecule. Dimers – compounds with two molecules of anthracene. Condensed– anthracene derivatives, in which two monomers linked between each other with 2 – mono and 1 – double bounds.

5. Monomer compounds of the reduced form Anthranol Anthrone Oxianthrone Monomer of the oxidizing form Anthraquinone

6. According to the location of OH-group, monomer compounds divided on the emodin and alizarin classes 1,2-dihydroxiantrachinine 1,8-dihydroxiantrachinine

7. Dimers Sennosides A & B

8. Condensed Hypericin

10. Physical and chemical propertiesAnthraquinones are yellow, orange or red highly crystalline solids. Their colour intensifies in solutions of alkali and conc. sulphuric acid. The solubility of anthraquinones depends on the form, in which they are present in plants. Free anthraquinone aglycones are soluble in ether, chloroform, benzole and poorly soluble in water. Anthraquinone glycosides are soluble in water, alcohol-water solutions, worse soluble in ethanol, insoluble in benzole, chloroform ant ether. Aglycones and glycosides are soluble in water solution of alkali with the formation of phenolates.

11. Identification reactions react Red colour doesn’t react Chrysophanol Yellow colour react Red colour react Emodin Red colour

12. Anthraquinone derivatives have different actions. • Derivatives of emodine have purgative action. This action appears in 8-12 hours after taking medicines. • Alizarines have spasmolitic and nephrolitic action. • Condenced derivatives have antibacterial action.

13. MP and MRM which contain emodines (chryzacines)

14. Frangulae Cortex – Alder buckthorn bark, EuPh, BPhFrangula alnus- Alder Buckthorn, Frangula, Alder DogwoodRhamnaceae- Buckthorn family Content : minimum 7.0 per cent of glucofrangulins. • Constituents.Anthraquinonederivatives present mainly in the form of glycosides. The rhamnoside (frangulin) was isolated in 1857. This is now known to consist of two isomers- frangulosides A and B, frangula-emodin-8-O-glucoside. The fresh bark contains glucofrangulins. Tanins, peptide alcaloids (frangulanin, franganin). Glucofrangulin A Glucofrangulin B

15. Possibleadmixtures of Alnus incana (Grey Alder), Alnus glutinosa (Black Alder) and of Rhamnus cathartica (Buckthorn)

16. Rhamnilum. Frangin

17. RHAMNI CARTHARTICAEFRUCTUS – • COMMON BUCKTHORN FRUIT, BPh • RHAMNUS CATHARTICA – Common buckthorn • Buckthorn (s): ramsthorn, waythorn • RHAMNACEAE • BAS.2-5 % anthraquinone glycosides: frangula-emodin, chrysophanol, glucofrangulins, frangulins, 3-4 % tannins, flavonoids, pectins, ascorbic acid. • Laxative acting • Decoction, laxative remedies and composition and herbal tea

18. Rhei Radices – Rhubarb root, EuPhRheum palmatum L. PolygonaceaeSynonims: Chinese Rhubarb, Turkey rhubarb.Contains not less than 2.2 % of hydroxyanthracene derivatives, expressed as rhein • Constituents. 3,5-6 % of anthraglycosides- rheum-emodine, chrysophanol, aloe-emodin, physcione, franguloemodin; 7-10% of tannins. • Usses. Is used as a powder or composed powders, tablets (0.5g) and dry extract for treatment of constipation. In low doses (0.05-0.2g) powder has astringent effect.

19. Radices Rhei

20. RUMICISRADICES - Horse sorrel root RUMEX CONFERTUS – Horse sorrel POLYGONACEAE Synonom: monk’s rhubarb BАS: anthracene derivatives (4 %): emodin, chrysophanol, aloe-emodin. Taninns (up to 12 %), flavonoids, oxynaphthaline derivatives, organic acids, resin, vitamin K, essential oil. Laxative (in the big doses); astringent (in the small doses) • Decoctions are used in colitis, enterocolitis and haemoroids.

21. Aloes arborescentis folia recens – Aloe leaf, EuPh, BPhAloe arborescens MillLiliaceaeSynonims: Cape aloes, socotrine aloes, bitter aloe, century plantContent : minimum 18.0 per cent of hydroxyanthracenederivatives, expressed as barbaloin , Constituents. Aloe-emodin and its glycoside chrysophanol, rheum-emodin. Hydroxyanthracene derivatives: as the principal components 25-40 % aloins A and B (=aloin, barbaloin = 10-C-β-D-glucosyldiastereoisomers of aloe-emodinanthrone); up to 20% of resinous substances, chromone derivatives (the main is 8-C-glycosylchromone aloeresin B), polysaccharides, amino acids, steroid compounds, enzymes. barbaloin (aloin)

22. Uses: a powerful colonic laxative (one of the strongest of the anthraquinone group) is used at the acute constipation. Maximum single dose is 50 mg. It should not be administrated during pregnacy. Externally- seborrheic dermatitis and different inflammatory diseases of skin. Also Aloe is widely used in cosmetic industry. As “Aloe vera gel” the stabilized viscous juice from the mucilage-containing parenchyma in the inner part of the succulent aloes leaves. Medicines of biogenic stimulants are obtained from fresh aloe leaves (V.P. Filatov). The medicines of biogenic stimulants - fluid aloe extract for injection, fluid aloe extract, aloe tablets – have the immune modulating, bactericidal and anti-inflammatorry action. They are used in ophthalmology, surgery, gastroenterology, dermatology. Clinical trials show the anti-cancer action of alcohol extract of Aloe.

24. Sennae Folia – Cassia leaf, EuPh, BPhSennae Fructus - Cassia fructusCassia acutifolia- Alexandrian sennaCassia angustifolia- Tinnevelly senna or Indian sennaFabaceae • Constituents. Leaves contain a family of hydroxyanthracene glycosides, the most plentiful of which are sennosides A and B. There are also small amounts of aloe-emodine and rhein 8-glucosides; mucilage; flavonoids and naphthalene precursors. Rhein Sennosides A and B

25. Senna leaves and fruits

26. Usses. Infusion is used as a laxative drug. To reduce the level of resinous substances the infusion should be filtrated after cooling 3-4 hours. Medicines- laxative and antihaemorrhoidal mixes, “Senadexin”, “Cafiol”, “Senade”, “Regulax”. Cafiol

27. MP and MRM containing alizarines

28. Rubiae Rhizomata cum radicibus Rubia tinctorum- Common Madder,RubiaRubiaceae • Constituents. Anthraquinone derivatives up to 3 % (alizarins) - rubiadin-glycoside, rubiadin, rubierythrinic acid; flavonoids, iridoids. • Uses. Medicines are used in treatment of cholelithiasis and nephrolithiasis and gout (podagra), because it dissolves and excretes phosphates, oxalates and urates. Dry extract is the main constituent of Cystenal and Marelin.

29. MRM and drugs from Rubia

30. HYPERICIHERBA – ST. JOINN’S WORT HERB HYPERICUM PERFORATUM, EuPH, BPh HYPERICACEAE Synonyms: tipton’s Weed, Chase-devil, Hypericum Content : minimum 0.08 % of total hypericins, expressed as hypericin BAS: hypericin, pseodohyperecin; flavonoids (hyperoside, rutin), antibiotic substances ( up to 3 % hyperforin), essential oils, up to more than 10% tannins. Antiinflammatory, antimicrobial, astringent, h(a)hemostatic agents

31. Tincture , “Novoimaninum”, infusion and decoction. Tablets “Helarium”