lecture 26 - cyanophore cyanogenic glycosides [compatibility mode]
TRANSCRIPT
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PHARM. DChemical Pharmacognosy- I
Lecture May 9th, 2011
Cyanophore (Cyanogenic)GLYCOSIDES
M. M. AhsanAhsan KhalidKhalid, , B.PharmB.Pharm, Pharm. D, Pharm. DM.PhilM.Phil Scholar (RIPS/RIU)Scholar (RIPS/RIU)
HIPSHIPS--HUKICHUKIC
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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 (β-glucosidases) that catalyze reactions
amygdalin glucose + prunasin glucose + mandelonitrile HCN + benzaldehyde
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Cyanophore (Cyanogenic) Glycosidesamygdalin 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
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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 paper3. Quantitative analysis of glycoside
plant in water + tartaric acid ---Steam distilled------HCN(determine by AgCl)
other methods GC, TMS
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Wild Cherry USP XVIII (1970)Synonym: wild black cherry, Virginian prune
bark, rum or whisky barkOrigin: 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 acidUse: flavoring vehicle (cough remedies)
sedative expectorant, antitussive, astringentused for colds, bronchitis, whooping cough
Adverse: fatal poisoning when ingested in large amounts
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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
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Other Cyanogenic glycosides1. 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 time2. Prulaurasin (Cherry - laurel leaves)
Prunus laurocerasus (Rosaceae)3. Manihotoxin(cassava)
Manihot utilissima (Euphorbiaceae)4. Dhurrin
Sorghum vulgare (Poaceae)
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Other Cyanogenic glycosides5. 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