Scribd Logo
Upload

Welcome to Scribd!

  • 160 views

    Anthraquinine

    Uploaded by

    pallavib.85
    Anthracene glycosides are oxygenated derivatives of anthracene that are used as laxatives, anti-inflammatories, and dyes, and include compounds like sennosides, cascarosides, and rhein found in plants like senna, cascara, and rhubarb which are reduced or oxidized forms of anthraquinone that can exist as aglycones or glycosides.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd

    Anthraquinine

    Uploaded by

    pallavib.85
    160 views38 pages
    Anthracene glycosides are oxygenated derivatives of anthracene that are used as laxatives, anti-inflammatories, and dyes, and include compounds like sennosides, cascarosides, and rhein found in plants like senna, cascara, and rhubarb which are reduced or oxidized forms of anthraquinone that can exist as aglycones or glycosides.

    Original Title

    PPT ANTHRAQUININE.pptx

    Copyright

    © © All Rights Reserved

    Available Formats

    PPTX, PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    Anthracene glycosides are oxygenated derivatives of anthracene that are used as laxatives, anti-inflammatories, and dyes, and include compounds like sennosides, cascarosides, and rhein found in plants like senna, cascara, and rhubarb which are reduced or oxidized forms of anthraquinone that can exist as aglycones or glycosides.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    160 views38 pages

    Anthraquinine

    Uploaded by

    pallavib.85
    Anthracene glycosides are oxygenated derivatives of anthracene that are used as laxatives, anti-inflammatories, and dyes, and include compounds like sennosides, cascarosides, and rhein found in plants like senna, cascara, and rhubarb which are reduced or oxidized forms of anthraquinone that can exist as aglycones or glycosides.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    You are on page 1of 38

    Anthracene (Anthraquinone)

    Glycosides
    Anthracene glycosides are oxygenated derivativesof pharmacological
    importance that are used as laxatives or cathartics, anti-inflammatory,
    antibacterial, antifungal and also as natural dyes.
    based on anthracene molecule
    O OH O

    tautomerization Oxidation

    Reduction

    H H H OH
    Anthrone Anthranol Oxanthrone

    Reduction

    O Oxidation
    8 1
    9

    10
    5 4
    O
    Anthraquinone
    Anthranols and Anthrones

    Reduced anthraquinone derivatives.


    Occur either freely (aglycones) or as glycosides.
    Isomers.

    Anthrone: Parent structure (pale yellow, non-


    soluble in alkali, non-fluorescent)

    Anthronol: brown-yellow, soluble in alkali,


    strongly fluorescent
    Anthronol derivatives(e.g. in Aloe – have similar
    properties – fluorescence used foridentification)
    2
    Oxanthrones

    Found in Cascara bark oxanthrone

    Intermediate products (between


    anthraquinones and anthranols)
    When oxidised oxanthrones it form
    anthraquinones
    Oxanthrones are detected by Modified
    Borntrager’s Test
    (oxanthrones oxidised using hydrogen
    peroxide)
    3
    Dianthrones
    Derived from 2 anthrone
    molecules
    2 molecules may/not be
    identical
    Dianthrones are form easily
    due to mild oxidation of
    anthrones
    It form important
    aglycones
    Cassia
    Rheum
    The activity decreases as oxidation level increase.

    Forms of Anthracene derivatives in Plants:


    Aglycones:

    OH OH OH OH OH OH OH OH
    O O O O

    HO CH3 CH2OH CH3 COOH


    O O O O
    Emodin Aloe-emodin Chrysophanol Rhein
    Glycosides:
    O- glycosides:
    e. g. Cascarosides A & B. They are both O- and C- glycosides. Each
    one contain two sugar unites.
    Glc O OH
    O

    CH2OH
    R1 R
    R= Glc, R1= H Cascaroside A
    C- glycosides: R= H, R1= Glc Cascaroside B
    e. g. Barbaloin it is formed from t he removal of one sugar from
    Cascarosides.

    OH OH
    O

    CH2OH
    H Glc
    Introduction to Anthraquinones
    Historically: Rhubarb, Senna, Aloes and
    Cascara were all used as purgative drugs.

    Monocotyledons: Only Liliaceae.


    Most commonly C-glycoside: barbaloin.

    Dicotyledons: Rubiaceae, Leguminosae,


    Polygonaceae, Rhamnaceae, Ericaceae,
    Euphorbiaceae, Lythraceae, Saxifragaceae,
    Scrophulariaceae and Verbenacacea. Also in
    certain fungi andlichen.
    10
    Reduced derivatives ofanthraquinones
    Oxanthrones, anthranols and anthrones

    Compounds formed by the union of 2


    anthrone molecules
    Dianthrones

    Aglycones:
    Chrysophanol/Chrysophanic acid : Rhubarb and
    Senna.
    Rhein : Rhubarb and Senna
    Aloe-emodin : Rhubarb and Senna
    11

    Emodin : Rhubarb and Cascara


    Senna - Leguminosae
    1) Consists of the dried
    leaflets of Cassia acutifolia
    (Alexandrian senna)

    2) dried leaflets of Cassia


    angustifolia (Tinnevelly
    senna –indian senna).

    Use: Laxative & purgative


    Alexandrian senna
    Syn.: Folia senna, Cassia senna,
    Egyptian senna, Nubian senna
    B.S.: dried leaflets of Cassia acutifolia
    Delile.
    Family: Leguminosae
    G.s.: Indigenous to Africa (tropical
    regions), Sudan, middle and nile
    territories
    Used since 9thand 10th century
    Itroduced into medicine by Arab
    physicians (used both the leaves and
    pods)
    Exported by Alexandria – name of the
    Sudanese drug.
    Indian Senna
    Syn.: Cassia leaf, Sonmukhi, senai-ki-patti, bhumiari
    B.S.: dried leaflets of Cassia angustifolia Vahl.
    Family: Leguminosae
    G.S.: South India, Tinneveley & Ramanathpurum district,
    Pakistan
    Morphology:
    Color: yellowish green
    Odour: Slight & characteristic
    Taste: Bitter & mucilagenous
    Shape: lanceolate to ovate lanceolate,
    entire margin, uneven base, acute apex,
    lamina pubesent.
    Size: 2.5 cm-6 cm long & 5mm-8mm wide.
    Cultivation &collection
    It is small shrub up to 1-1.5 mt. height. Twice a year & after
    paddy crops.
    Soil required is sandy loamy, coarse gravelly, loamy soil
    which well ploughed, leveled & semi-irrigated.
    Seeds sawn in October & February. Within 2-3 months plant
    are ready for collection.
    Leaflets are collected by hand before flowring. Dried in shade
    to maintain natural green color.
    1ststage: leaflet are greenish in color & thick
    2ndstage: harvesting is done after 30 days of 1st stage
    3rdstage: plant are uprooted
    Packing: in bales with pressure that cause oblique impressions in
    leaves. it remain less brittle and in good condition.
    Fresh: anthron, dried at 20-50◦ - dianthron, above 50◦ -
    anthraquinone
    Senna – chemical Constituents
    Senna consist four types of glycosides:
    Sennoside A
    Sennoside B
    Sennoside C
    Sennoside D
    In theiractivecostituentsare sennoside A, sennosidesB
    Upon hydrolysis of sennosides it gives two molecules
    glucose+aglycones: Sennidin A and Sennidin B. Rhein
    8-glucosides, Rhein 8-diglucosides
    Aloe-emodin
    Crysophenic acid, myricyl alcohol, resin
    Tinnevellin glycoside(indian senna), 6-hydroxy mucizin
    glucoside
    Chemical constituents:
    Comparison of
    Alexandrian and Tinnevelly Senna
    Macroscopical Macroscopical

    larger than 4 cmin exceeds 5cm in length


    length
    Grey-green Yellow-green
    Asymmetric at base Less asymmetric at
    base
    Broken and curled at broken and normally
    edges flat
    Few press markings Often shows
    impressions (mid vein)
    21
    Comparison between
    Alexandrian and Tinnevelly Senna

    Microscopical Microscopical

    Hairs less numerous


    Hairs – numerous (approximately six
    (approximately three epidermal cells apart)
    epidermal cells apart) Stomata have 2-3
    Most stomata have subsidiary cells with
    twosubsidiary cells
    the respective ratio
    7:3

    22
    Senna – Allied Drugs &Substitutes
    1. Bombay, Mecca and Arabian Sennas (found in Cassia
    angustifolia from Arabia).
    2. Palthe senna( Cassia Auriculata)
    3. Dog senna – Cassia obovata
    4. Cassia podocarpa
    5. Argel leaves – Solenostemma argel
    6. Coriario myrtifolia

    24
    Senna Fruit

    25
    Chemical test:
    Borntrager’s and Modified Borntrager’s test:

    Boil plant material with dil. HCl for 10 min, filter and shake with
    organic solvent (Ether or Benzene).Separate the organic solvent.
    Add ammonia/ NH 4OH .Positive result indicated by Rose Red
    colour in the aqueous alkaline layer.
    Cascara
    Syn: Sacred bark, cortex rhamni, Californian buckthron, cascara
    sagrada
    B.S.; Rhamnus pershiana
    Family: Rhamnaceae
    G.S.: N.Colifornia, columbia, canada, Kenya
    Morphology:
    Color: outer surface: dark purple to brown (lichens & moss)
    Inner surface: yellow to reddish brown
    Odour: cherecterictic
    Taste: bitter
    Shape: Single squill, curved or channel
    Size: 5-20 cm long, 2-3 cm wide, 1.2-4 mm thick
    Chem const: Cascaroside A,B,C,D
    Use: bark extractcollected, dried and stored for 12 months
    (↓ anthraquinone content -> less toxic)
    more violent purgative
    griping action
    harder to eliminate

    Use: night before to clear bowels for x-rays.


    Larg dose use as cathartic.
    Chemical constituents:
    (i) 4 primary glycosides
     O- and C- linkages

    To get aglycones FeCl3


    To get aloins oxidise withacid

    (ii) C-glycosides - twoaloins


     barbaloin – derived from aloe-emodin
     chrysaloin – derived from chrysophanol
    (iii) a number of O-glycosides
     derived from emodin oxanthrone, aloe-emodin, chrysophanol
    (iv) various dianthrones
     incl. emodin, aloe-emodin, chrysophanol, herterodianthrones palmidin A
    BC
    (v) aloe-emodin, chrysophanol, emodin in free state
    Rhubarb
    Syn.: Rheum, Radix rhei, da huang
    B.S.: Peeled & dried rhizomes , root of Rheum officinale
    Bail., R.palmetum L., R.rhaponticum Willd (chinese)
    R.emodi Wall., R. webbianum Royale (Indian)
    Family: Polygonaceae
    G.S.: Tibet to south east china, germany, south europe,
    kashmir, kullu, Sikkim, UP, panjab, nepal
    Morphology
    Color: fresh surface after cut pink to dull grey in day
    light & reddish brown UV
    Odour: Characteristics
    Taste: Bitter, gritty, astringent
    Size: 8-10 cm in length, 3-4 cm thick
    C.C.: rhein, glucorhein, emodin, aloe emodin and
    chrysophenol
    Palmidin A, B, C
    Rheinoside A,B,C,D
    USE
    Bitter, stomachic, laxative, purgative, diarrhoea,
    eczema, psoriasis
    ADULTRANTS
    Rheum rhaponticum,
    R. undulatum
    R.copactum
    Japanese rhubarb
    ALOE
    Syn.: Kumari, musabar, korphad, Gheekunwar, Ghrit
    kumara
    B.S.: dried juce of leaves of Aloe barbadensis Miller(
    Curacao Aloe), Aloe perryi Baker (Socotrine aloe),
    Aloe ferox Miller., Aloe spicata Baker (Cape Aloe)
    Family: Liliaceae
    G.S.: Estern & southern Africa, west Indies, India,
    western region.
    Aloe perryi, barbadensis, ferox
    Preparation of Cape Aloes
     Cape Aloes are prepared from the wild plants of Aloe
    ferox.

     Leaves are cut transversely near thebase.

     Twohundred leaves arranged around a shallow hole in


    the ground (lined withcanvas or goatskin).

     Cut ends overlap &drain into the canvas.


    After 6hrs all the juiceis collected.

     Transferred to adrum.

     Boiled for 4hrs on an open fire.

     P41oured into tins while hot  solidifies.


    Preparation of Cape Aloes

    42
    Cape Aloes - Characteristics
    Dark brown or Green-
    brown

    Glassy masses

    Thin fragments have a


    deep olive colour

    Semi-transparent.
    43
    Cape Aloes - Characteristics
    Powder: green-yellow

    When rubbed two pieces


    of drug together – powder is
    found on the surfaces.

    Characteristic sour odour


    (rhubarb/apple-tart odour).

    Taste: nauseous and bitter.

    Microscopy: powder in
    lactophenol – amorphous.
    44
    Characteristics of Curacao Aloes
    Colour: yellow-brown – chocolate brown.
    Cut at base, V shaped container of wood 1-2 mlong with cut
    surface towards container.
    Poor qualities (overheated) blackcolour.
    Opaque
    Breaks witha waxyfacture
    Semi-transparent
    More opaque on keeping.
    Nauseous and bitter taste.
    Thick hot juice taken completely in copper(metal) pan till it
    become thick(hard)

    45
    Socotrine aloe
    Juice collected on goat skin and allow to dry for long
    time without heating or boliling.
    It forms viscous pasty mass which is filled in
    container of wood.
    Zinzibar aloe
    Same as above
    Also called monkey skin aloe.
    Aloes - Constituents
    C-glycosides
    Resins
    Glycosides
    Aloin
    Barbaloin
    Isobarbaloin
    Aloe-emodin

    Cape Aloes: Also Contain


    Aloinoside A &Aloinoside B
    (O-glycosides of
    barbaloin)
    47
    Aloe - Constituents

    48
    Aloe Constituents &Chemical
    Tests:
     Unlike C-glycosides, O-glycosides
    of Aloe are not hydrolysed by
    heating withdilute acids or alkali.
    Can be decomposed withferric
    chloride &dilute HCl
    Modified Borntrager’s Test– oxidative
    hydrolysis. Anthraquinones give a
    red colour when shaken withdilute
    ammonia.
    General test for aloes.--All Aloes give
    a stronggreen fluorescence with
    borax (characteristic of
    49
    anthranols) -
    Aloe - Uses
    Purgative, abortification,
    emolient, stomachic,
    stimulant &tonic.
    Used in solar, tharmal,
    radiation burns, in skin
    irritation
    Cosmetic

    50
    Aloe vera Products
    These are derived from
    the mucilage gel –
    parenchyma cells
    Should not be confused
    withaloes (juice of
    pericycle – juice used for
    laxative effect).
    Cosmetic industry
    (usefulness often
    exaggerated) - Used as
    suntan lotions, tonics and
    food additives.
    Mucilage =
    52
    polysaccharide of
    glucomannans and pectin

    You might also like