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    Lecture 26 - Cyanophore Cyanogenic Glycosides (Compatibility Mode)

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    1. Cyanogenic glycosides are glycosides that yield hydrocyanic acid (HCN) on hydrolysis. Common examples include amygdalin and sambunigrin. 2. Enzymes such as amygdalin hydrolase and prunasin hydrolase catalyze reactions that produce HCN from cyanogenic glycosides. 3. Cyanogenic glycosides such as amygdalin are found in apricot pits and are sometimes claimed to have anti-cancer properties, though the FDA does not recognize these claims due to potential toxicity from HCN.

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    Lecture 26 - Cyanophore Cyanogenic Glycosides (Compatibility Mode)

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    ahsanonweb1983
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    1. Cyanogenic glycosides are glycosides that yield hydrocyanic acid (HCN) on hydrolysis. Common examples include amygdalin and sambunigrin. 2. Enzymes such as amygdalin hydrolase and prunasin hydrolase catalyze reactions that produce HCN from cyanogenic glycosides. 3. Cyanogenic glycosides such as amygdalin are found in apricot pits and are sometimes claimed to have anti-cancer properties, though the FDA does not recognize these claims due to potential toxicity from HCN.

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    Lecture 26 - Cyanophore Cyanogenic Glycosides [Compatibility Mode]

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    1. Cyanogenic glycosides are glycosides that yield hydrocyanic acid (HCN) on hydrolysis. Common examples include amygdalin and sambunigrin. 2. Enzymes such as amygdalin hydrolase and prunasin hydrolase catalyze reactions that produce HCN from cyanogenic glycosides. 3. Cyanogenic glycosides such as amygdalin are found in apricot pits and are sometimes claimed to have anti-cancer properties, though the FDA does not recognize these claims due to potential toxicity from HCN.

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    Lecture 26 - Cyanophore Cyanogenic Glycosides (Compatibility Mode)

    Uploaded by

    ahsanonweb1983
    1. Cyanogenic glycosides are glycosides that yield hydrocyanic acid (HCN) on hydrolysis. Common examples include amygdalin and sambunigrin. 2. Enzymes such as amygdalin hydrolase and prunasin hydrolase catalyze reactions that produce HCN from cyanogenic glycosides. 3. Cyanogenic glycosides such as amygdalin are found in apricot pits and are sometimes claimed to have anti-cancer properties, though the FDA does not recognize these claims due to potential toxicity from HCN.

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    PHARM.

    D Chemical Pharmacognosy- I Lecture May 9th, 2011

    Cyanophore (Cyanogenic) GLYCOSIDES


    M. Ahsan Khalid, B.Pharm, Pharm. D B.Pharm,
    M.Phil Scholar (RIPS/RIU) HIPSHIPS-HUKIC

    Cyanophore (Cyanogenic) Glycosides


    Glycosides that yield hydrocyanic acid (HCN) on hydrolysis common glycosides are derivatives of mandelonitrile (benzaldehyde - cyanohydrin)
    1. Amygdalin ------- mandelonitrile (aglycone)
    prunasin

    2. Sambunigrin ------- S - mandelonitrile (aglycone)

    accompanied by enzymes (-glucosidases) that catalyze reactions


    amygdalin glucose + prunasin glucose + mandelonitrile HCN + benzaldehyde

    Cyanophore (Cyanogenic) Glycosides


    amygdalin A glucose + prunasin B glucose + mandelonitrile C HCN + benzaldehyde
    A - amygdalin hydrolase B - prunasin hydrolase C - mandelonitrile lyase

    widely used as flavoring agent anti cancer claim ---- amygdalin (laetrile or Vit B17) - control of sickle cell anemia
    not recognized by FDA as a cancer drug because of high HCN content, potential for overdose or poisoning

    Cyanogenic Glycoside
    aglycones are derived from nitrogen intermediates (amino acid)
    Test: 1. Sodium picrate (yellow) --HCN-- Na isopurpurate (brick red) 2. Guaiacum resin (in methanol) + CuSO4 --HCN----blue coloration of paper 3. Quantitative analysis of glycoside plant in water + tartaric acid ---Steam distilled-----HCN(determine by AgCl) other methods GC, TMS

    Wild Cherry USP XVIII (1970)


    Synonym: wild black cherry, Virginian prune bark, rum or whisky bark Origin: carefully dried stem bark of Prunus serotina (Rosaceae) - also known as Prunus virginiana (wild black cherry tree) Constituent: prunasin ---partial H+---- HCN p-coumaric acid, trimethyl gallic acid Use: flavoring vehicle (cough remedies) sedative expectorant, antitussive, astringent used for colds, bronchitis, whooping cough Adverse: fatal poisoning when ingested in large amounts

    Apricot pits

    Kernel of various varieties of Prunus americana (Rosaceae) sold as a health food as source of laetrile or amygdalin - sold due to amygdalin but banned by FDA due to ineffectivity and potential danger

    Other Cyanogenic glycosides


    1. Linamarin Flax, linseed, lint bells Linum usitatissimum (Linaceae) - treatment of diarrhea, constitpation, gastritis; poultice skin inflammation - adverse effect: intestinal blockage - capable of cholesterol and bleeding time 2. Prulaurasin (Cherry - laurel leaves) Prunus laurocerasus (Rosaceae) 3. Manihotoxin(cassava) Manihot utilissima (Euphorbiaceae) 4. Dhurrin Sorghum vulgare (Poaceae)

    Other Cyanogenic glycosides


    5. Sambunigrin Sambucwas nigra (Caprifoliaceae) 6. Vicianin Vicia angustifolia (Fabaceae) 7. Phaseolunatin Phaseolus lunatus (Fabaceae) 8. Amygdalin Prunus amygdalus (Rosaceae) Prunus persica (Rosaceae) - peach
    - constipation, cough, bad breath, blisters, bronchitis - abundant in persic oil, peach kernel oil , seed, bark, leaves and flowers

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