Anthaquinones
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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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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.


Classes of anthraquinones

Classes of Anthraquinones

Based on degree of oxidation status

oxid.

red.


Biosynthesis of anthraquinones

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


Anthaquinones

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


Anthraquinones from shikimic acid

Anthraquinones from Shikimic Acid


Anthaquinones

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


Natural sources

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


Medicinal use of antharquinones

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


Frangula bark

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


Cascara bark

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)


Aloe spp liliaceae

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)


Other aloe preparations

Other Aloe Preparations

  • Aloe vera leaf mucilage from parenchymatous layer

  • Herbal remedy for sunburn

  • Cosmetic industry

  • FREE FROM ANTHRAQUINONES


Rhubarb radix

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


Anthaquinones

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


Senna folium

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


Senna fructus

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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