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Anthaquinones

Anthaquinones. Active components of many crude drugs with purgative properties Colored compounds traditionally used as dyes Mostly glycosides (mainly glucosides or rhamnosides) Sugar residue is prerequisite for pharmacological effects 9,10-anthraquinone as basic st.

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Anthaquinones

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  1. Anthaquinones • Active components of many crude drugs with purgative properties • Colored compounds traditionally used as dyes • Mostly glycosides (mainly glucosides or rhamnosides) • Sugar residue is prerequisite for pharmacological effects • 9,10-anthraquinone as basic st.

  2. Classes of Anthraquinones Based on degree of oxidation status oxid. red.

  3. Biosynthesis of Anthraquinones • Mainly produced via acylpolymalonate (acetate-malonate) pathway in Polygonaceae & Rhamnaceae & Leguminosae…. • Starts with acetyl CoA carboxylation to malonly CoA then continues in the usual way of formation of the poly-keto-methylene-chain with simultaneous loss of CO2 followed by cyclisation • Shikimate-mediated in Rutaceae, Rubiaceae & Gesneriaceae

  4. In the biosynthesis of the anthraquinones for the formation of the poly-keto-methylene-chain : 1 acetyl CoA and 7 Malonyl CoA are used.

  5. Anthraquinones from Shikimic Acid

  6. Important anthraquinones: OH at C-1 and C-8R at C-3: CH3………………ChrysophanolR at C-3: CH2OH………….Aloe-emodineR at C-3: COOH…………. RheinR at C-3: CH3 and at C-6 OH Frangula-emodineR at C-3: CH3 and at C-6 OCH3 Phycion

  7. Natural Sources • Widespread in plant kingdom • Produced by microorganimsms e.g. Penicillium & Aspergillus spp • Anthraquinone-rich plant families: Liliaceae, Polygonaceae, Rhamnaceae, Rubiaceae, Fabaceae, Rutaceae Animals produce anthraquinones e.g. cochineal insect

  8. Medicinal Use of Antharquinones • Purgatives • Pure compounds are rarely prescribed • Mostly used as simple extracts of crude drugs • Sugar moiety increases solubility & facilitates transport to the site of action • Aglycone is active part • Anthroneis the most effective form • Normal flora in colon liberates aglycone to stimulate peristalsis • Too much anthrones in crude drugs are not suitable for use (frangula bark storing to allow {O} to anthraquinone

  9. Frangula Bark • Dried bark of Rhamnus frangula L. (Rhamnaceae) • Fresh frangula rich anthrones (too strong) • Storing for one year to oxidize (mild activity and widely used) • 2-4% glucofrangulins • Frangulin A & B are minor

  10. Cascara Bark Dried bark of Rhamnuspurshiana(Rhamnaceae) • Cascara (Spanish word from cascara sagrada=sacred bark) • Fresh cascara like frangula (must be stored before use) • 6-9% Anthraquinones mainly Cascarosides A-D • A & B aloe-emodineanthrone (aglycone) • C & D chrysophanolanthrone (aglycone)

  11. Aloe spp (Liliaceae) • Aloe barbadensis, A. feroxdried juice from the leaves (from leave base) • Strong purgative • Barbaloin A & B (stereoisomers) • Aloinosides A & B (stereoisomers) • Aloin= H2O-sol. components of aloe Aloin might be used for barbaloin Best avoid aloin (ambiguous term)

  12. Other Aloe Preparations • Aloe vera leaf mucilage from parenchymatous layer • Herbal remedy for sunburn • Cosmetic industry • FREE FROM ANTHRAQUINONES

  13. Rhubarb radix الرواند • Dried rhizomes & roots of Rheum palmatum (Polygonaceae) • Active Ingredients: mixture of complex anthraquinone glycosides. Aglycone classification • Noncarboxyllated chrysophanol, aloe-emodin, emodin & physcion • COOH-containing e.g. rhein • Anthrones & dianthrones of the above • Hetero-dianthrones of anthrones Tannins of rhubarb responsible for mild activity

  14. Raponticin: A stilbene glucoside from Rheum raponticum, R. undulatum; estrogenic action, treatment of menopausol symptoms; Alzheimer’s disease(?)

  15. Senna Folium • Dried leaves of Cassia angustifoliaor Cassia senna= C. acutifolia (Fabaceae) • Sennosides A-D • Sennosides A & B (Homodiantrone) • Sennosides C & D (heterodianthrone) • Sennosides A & B are ingredients of many products in the market

  16. Senna fructus • Dried fruit of C. sennaor C. angustifolia • Same active ingredients as leaves in addition to rhein dianthrones containing up to 10-sugar molecules • Milder laxative than leaves

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