Medicinal plants and medical plant materials that contain anthracene derivatives

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 С 6 -С 2 -С 6. Anthracene Anthraquinone

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.

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.

Monomer compounds of the reduced form Monomer of the oxidizing form AnthranolAnthrone Oxianthrone Anthraquinone

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

Dimers Sennosides A & B

Condensed Hypericin

Physical and chemical properties Anthraquinones 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.

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

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.

MP and MRM which contain emodines (chryzacines)

Frangulae Cortex – Alder buckthorn bark, EuPh, BPh Frangula alnus- Alder Buckthorn, Frangula, Alder Dogwood Rhamnaceae- Buckthorn family Constituents. Anthraquinone derivatives present mainly in the form of glycosides. The rhamnoside (frangulin) was isolated in 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). Content : minimum 7.0 per cent of glucofrangulins. Glucofrangulin AGlucofrangulin B

Possible admixtures of Alnus incana (Grey Alder), Alnus glutinosa (Black Alder) and of Rhamnus cathartica (Buckthorn)

Rhamnilum. Frangin

RHAMNI CARTHARTICAE FRUCTUS – 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

Rhei Radices – Rhubarb root, EuPh Rheum palmatum L. Polygonaceae Synonims: 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 ( g) powder has astringent effect.

Radices Rhei

RUMICIS RADICES - 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.

Aloes arborescentis folia recens – Aloe leaf, EuPh, BPh Aloe arborescens Mill Liliaceae Synonims: Cape aloes, socotrine aloes, bitter aloe, century plant Content : minimum 18.0 per cent of hydroxyanthracene derivatives, expressed as barbaloin, Constituents. Aloe-emodin and its glycoside chrysophanol, rheum-emodin. Hydroxyanthracene derivatives: as the principal components % aloins A and B (=aloin, barbaloin = 10-C- β-D-glucosyl diastereoisomers of aloe-emodin anthrone); up to 20% of resinous substances, chromone derivatives (the main is 8-C-glycosylchromone aloeresin B), polysaccharides, amino acids, steroid compounds, enzymes. barbaloin (aloin)

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.

Sennae Folia – Cassia leaf, EuPh, BPh Sennae Fructus - Cassia fructus Cassia acutifolia- Alexandrian senna Cassia angustifolia- Tinnevelly senna or Indian senna Fabaceae 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. Sennosides A and B Rhein

Senna leaves and fruits

Cafiol 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”.

MP and MRM containing alizarines

Rubiae Rhizomata cum radicibus Rubia tinctorum- Common Madder,Rubia Rubiaceae 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.

MRM and drugs from Rubia

HYPERICI HERBA – 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

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