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    Classification of Glycosides

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    m__rubel
    This document classifies and describes various types of glycosides. It divides glycosides into categories based on: 1) the type of sugar moiety, 2) therapeutic activity, 3) the linkage between the sugar and aglycone, and 4) the chemical nature of the aglycone. Examples are provided for many categories including cardiac glycosides, anthraquinone glycosides, saponins, cyanophores, isothiocyanates, and others. Acetals, hemiacetals, and the biosynthesis of prunasin are also briefly discussed.

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    Classification of Glycosides

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    m__rubel
    4K views12 pages
    This document classifies and describes various types of glycosides. It divides glycosides into categories based on: 1) the type of sugar moiety, 2) therapeutic activity, 3) the linkage between the sugar and aglycone, and 4) the chemical nature of the aglycone. Examples are provided for many categories including cardiac glycosides, anthraquinone glycosides, saponins, cyanophores, isothiocyanates, and others. Acetals, hemiacetals, and the biosynthesis of prunasin are also briefly discussed.

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    This document classifies and describes various types of glycosides. It divides glycosides into categories based on: 1) the type of sugar moiety, 2) therapeutic activity, 3) the linkage between the sugar and aglycone, and 4) the chemical nature of the aglycone. Examples are provided for many categories including cardiac glycosides, anthraquinone glycosides, saponins, cyanophores, isothiocyanates, and others. Acetals, hemiacetals, and the biosynthesis of prunasin are also briefly discussed.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    4K views12 pages

    Classification of Glycosides

    Uploaded by

    m__rubel
    This document classifies and describes various types of glycosides. It divides glycosides into categories based on: 1) the type of sugar moiety, 2) therapeutic activity, 3) the linkage between the sugar and aglycone, and 4) the chemical nature of the aglycone. Examples are provided for many categories including cardiac glycosides, anthraquinone glycosides, saponins, cyanophores, isothiocyanates, and others. Acetals, hemiacetals, and the biosynthesis of prunasin are also briefly discussed.

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    Classification of Glycosides

    A.A. On the basis of sugar moiety such as glucoside , rhamnoside, etc.


    CH2 OH O C6H11O5

    CH2OH H H OH OH H O H H O OH O

    Salicin (saligenin + glucose)

    OH Arbutin (hydroquinone + glucose)

    A.B. On the basis of therapeutic activity such as


    - Cardiac glycosides, e.g. Digitalis, Strophenthuss, etc. - Laxative glycosides, e.g. Aloe, Senna, Cascara sagrada, etc.

    C. On the basis of linkage of sugar molecule with the aglycon a) O- Glycosides: here the sugar is combined with the alcoholic or phenolic hydroxyl group of the aglycone.

    R = Glucose in daucosterol

    RO
    OCH3 RO O OH

    R = Rhamnose - glucose

    OH

    b) N- Glycosides: In these glycosides the amino group (-NH2 / -NH-) is condensed with the sugar, e.g. nucleosides, coenzyme, etc.
    NH2 N

    NH2 N N O
    O

    N N

    N N CH2OH OH H H H

    CH2 H H O O CH3 H CH N OH P O

    O H H OH OH N

    HO PH OOH H

    O HO PH OCH2 H3C HO C C H

    Adenosine (Adenine + ribose)

    CH OH

    SH

    Coenzyme A

    c) S- Glycosides: These glycosides contain a sugar moiety attached to the sulfur of the aglycone, e.g. isothiocyanate glycosides.
    C 3H 5 C N S O C6H11O5
    HO CH2 C S C6H11O5 N O SO2-O-K

    SO3K
    Sinalbin

    Sinigrin

    d) C- Glycosides: Condensation of a sugar directly to a carbon atom of the aglycone gives c-glycosides, e.g. aloin, chrysaloin, etc.
    C6H11O5

    OH

    OH
    HO O CH3

    CH2R H C6H11O5
    R = OH, Barbaloin H, Chrysaloin
    CH3 O

    Aloesin

    D) On the basis of the chemical nature of aglycone, the glycosides can be classified into following groups:
    O

    1. Cardioactive
    CH3 CH3 OH HO H

    Digitalis Strophenthus

    + digitoxose Digitoxigenin (cardenolide, C23 steroid)


    O O

    CH3 CH3 OH RO H

    Squill

    R = H, Scillarenin A (bufadienolide, C24 steroid) R = rham glu, Scillaren A 5

    2. Anthraquinone

    OH

    OH

    Cascara sagrada Aloe Senna Rhubarb


    CH2R

    H C6H11O5 R = OH, Barbaloin H , Chrysaloin

    3. Saponin
    CH3

    O CH3

    Glycyrrhiza Dioscorea

    HO

    HO
    + rhamnose, + glucose

    Spiroketal steroid nucleus (neutral) diosgenin

    amyrin (aglycone, pentacyclic triterpenoid, acidic)

    4. Cyanophore

    H C CN O C6H11O5

    Mandelonitrile glucoside

    Wild cherry Bitter almond


    H CH OH

    H C C6H12O6 + CN Mandelonitrile OH

    + HCN Benzadehyde

    5. Isothiocyanates
    C 3H 5 C N S O C6H11O 5 SO3K

    Black mustard White mustard

    Sinigrin myrosin H2O S C CH2 C CH2 + KHSO 4 + C6H12O6 H glucose Allyl isothiocyanate N

    6. Flavanol / flavanoid
    OH HO O OH O OH O C12H21O9

    Citrus fruit

    Rutin

    7. Alcohol
    CH2OH O C6H 11O 5 + H2 O Salicin Saligenin CH 2OH OH + glucose

    Salix Populus

    8. Aldehyde

    CHO

    Vanilla

    OCH3 OR R = H, vanillin R = glu, glucovanillin

    9. Lactone

    Cantharide Tonka beans


    HO O
    Coumarin

    10. Phenol

    OC6H11O5

    OH

    Uva ursi
    + glu

    + H2O

    OH Arbutin

    OH Hydroquinine

    11. Tannin
    HO

    OH OH

    Nutgall Hamamelis leaf

    COO C 6H11O5 Glucogallin (glucoside of gallic acid)

    10

    An acetal is a molecule with two single bonded oxygen attached to the same carbon atom. Hemiacetals and hemiketals are compounds derived from aldehyde and ketones respectively. These compounds are formed by formal addition of an alcohol to the carbonyl group.

    H H+ R C O + ROH R'

    H C OR

    OH Hemiacetal H H+ R' C OR + ROH R' C OR acetal OR OH Hemiacetal (an alcohol) H

    11

    H COOH H NH2

    H H

    H COOH NHOH

    H CH NOH

    L-Phenylalamime

    N-Hydroxy-L-phenylalanine

    Phenylacetaldoxime

    H C N

    OH C N
    glucosyl transferase + UDP glucose

    Mandelonitrile

    a-Hydroxymandelonitrile

    H HO O H O C H N

    H OH OH H H OH

    Prunasin

    The biosynthetic pathway for the cyanogenic glycoside, prunasin.

    12

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