2nd Shift Glycosides: Common Sources Flashcards

1
Q

5 Anthracene/Anthraquinone Glycosides

A
  1. Aloes
  2. Rhubarb
  3. Cascara sagrada
  4. Frangula
  5. Senna
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2
Q

Biological source of aloes

A

dried latex leaves of Aloe barbadensis (Curacao aloe)

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3
Q

Organoleptic properties of aloes
*color
*odor
*taste
*texture

A

*color - brownish black opaque mass
*odor - strong odor, resembles iodoform
*taste - bitter
*texture - waxy, somewhat resinous

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4
Q

Chemical constituents of aloes

A

aloe emodin (free state), aloin (glycoside), emodin oxanthrone, emodin anthrone, emodin anthranol, emodin, isobarbaloin and a resin, aloesin

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5
Q

free state constituent of aloes

A

aloe emodin

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6
Q

glycoside constituent of aloes

A

aloin

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7
Q

biological source and family of rhubarb

A

Rhubarb, rhizomes and roots of Rheum officinale; Polygonaceae

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8
Q

Preparation of rhubarb

A

rhizomes are collected from 6-10 year old plants and are cut in either longitudinal or transverse manner

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9
Q

Chemical constituents of rhubarb

A

*Anthraquinone with COOH: rhein, glucorhein
*Anthraquinone without COOH: emodin, aloe-emodin, chrysophanol, physcion
*Anthrone and dianthrone of emodin
*Heterodianthrones: Palmidin A, B and C
*Other constituents: rheinolic acid, pectin, starch, fat and calcium oxalate

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10
Q

biological source and family of cascara sagrada

A

dried bark of Rhamnus purshiana; Rhamnaceae

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11
Q

preparation of cascara sagrada

A

Bark collected during dry season

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12
Q

Organoleptic Description of Cascara sagrada:
* Color:
* Odor:
* Taste
* Size (Thickness):
* Shape:
* External Bark:

A
  • Color: Outside-Purplish brown; Inside-Reddish brown
  • Odor: Nauseatic odor
  • Taste: Persistently bitter
  • Size (Thickness): 1-4 mm
  • Shape: Occurs in quills or channels. Also available in small, flat and broken segments
  • External Bark: smooth with presence of scattered lenticel, lichens and cork
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13
Q

chemical constituent of cascara sagrada

A

*Normal O-glycosides (10-20%)
* Aloin like C-glycosides (80-90%) e.g. Barbaloin/Aloin, Deoxybarbaloin (Chrysaloin)
* Main active constituents: Cascarosides A, B, C and D

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14
Q

another name for Deoxybarbaloin

A

chrysaloin

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15
Q

biological source and family of frangula

A

dried bark of Rhamnus frangula; Rhamnaceae

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16
Q

preparation of frangula

A

Like cascara, bark collected during dry season

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17
Q

Chemical constituents of frangula

A
  • Glucofrangulins A and B
  • Frangulin A and B
  • Also contains Emodin and Chrysophanic acid
18
Q

Biological source and family of senna

A

*Dried leaflets of Cassia senna L.
*Cassia acutifolia (Alexandria senna)
*Cascara angustifolia (Tinnevelley senna)

Fam. Leguminoseae

19
Q

Preparation of senna

A

Leaves are collected in April and in September and subsequently allowed to dry under the sun, then leaflets are separated thru garbling

20
Q

Collection month for Senna

A

April and September

21
Q

Organoleptic description of alexandria senna based on:
color:
odor:
taste:
size:
shape:
texture:

A

Pale greyish green
Slight
Mucilaginous and Bitter
L: 2-4 cm W 7-12 mm
Ovate-lanceolate
Thin and brittle

22
Q

Organoleptic description of tinnevelley senna based on:
color:
odor:
taste:
size:
shape:
texture:

A

yellowish green
slight
Mucilaginous and Bitter
L: 2.5-5 cm W 3-8 mm
Lanceolate
Thin and flexible

23
Q

Chemical constituents of Senna

A
  • Sennosides A, B, C and D
  • Also contains kaempferol
24
Q

Method of extraction for sennosides

A
  • Dried and powdered leaves is macerated with 80% acetone/90%
    methanol for 6 hours, followed by cold water for 2 hours.
  • The sennosides and other anthracene derivatives can be extracted with a mixture of polyethylene glycol in 70% v/v ethanol
  • Drug powder is macerated with citric acid in methanol followed by repeated extraction with mixture of methanol, toluene and ammonia. The resulting extract is treated with conc. solution of calcium chloride to salt out calcium derived sennosides.
25
Q

4 Phenol Glycosides

A

arbutin, gaultherin, salicin, populin

26
Q

biological source and family of arbutin

A
  • Dried leaves of Bergenia crassifolia (Fam. Saxifragaceae)
  • Dried leaves of Uva-ursi/Bearberry Arctostaphylos uva-ursi (Fam. Ericaceae)
27
Q

biological source and family of gaultherin

A

Leaves of Gaultheria procumbens L. (Fam. Ericacea)

28
Q

description of gaultherin

A

Needle-shaped start formation when crystallize with acetone and soluble in water and alcohol

29
Q

chemical constituents of gaultherin

A
  • Upon hydrolysis of gaultherin with 3% Sulfuric Acid, it forms 1 mole
    of methyl salicylate, d-glucose and d-xylose.
  • Upon enzymatic hydrolysis with gaultherase, it give 1 mole of primeverose, a disaccharide and methyl salicylate.
30
Q

chemical name of salicin

A

Saligenin b-Dglucopyranoside

31
Q

biological source of salicin

A
  • Bark of poplar (Populus) and willow (Salix)
  • Salix fragilis or Salix purpurea (Fam. Salicaceae)
32
Q

preparation of salicin

A

Powdered bark is macerated with hot water for several hours, filtered and treated with lead acetate to precipitate and remove the tannins. Next, subsequently treated with hydrogen sulfite to remove excess of lead. Then, filtrate is neutralized with ammonia to allow salicin to crystallize after chilling.

33
Q

chemical constituents of salicin

A

Hydrolyzed by the enzyme emulsin yielding one mole of saligenin and d-glucose.

34
Q

chemical name of populin

A

Salicin benzoate

35
Q

biological source and family of populin

A

Populus tremula L., P. nigra L. (Fam. Salicaceae)

36
Q

preparation of populin

A

May be prepared from Salicin by melting with benzoic anhydride or Salicin and benzoyl chloride in presence of KOH.

37
Q

3 Cardiac/Steroid Glycosides

A

digitalis, Squill(European, Indian and Red Squill), Strophantus

38
Q

biological source and family of digitalis

A

Dried leaves of Digitalis purpurea L. (Fam Scrophulariaceae)

39
Q

preparation of digitalis

A

Leaves are normally picked in the afternoon during Aug/Sept. and dried using stream of hot air not more than 60C. However, it causes loss in potency due to chemical degradation.

40
Q

description of digitalis
color:
taste:
shape:

A
  • Color; Dark greyish green
  • Taste: Bitter
  • Shape: Orate-lanceolate to broadly ovate
41
Q

chemical constituents of digitalis

A

Contains three important glycosides namely: Purpurea glycoside A, B and C, which upon hydrolysis give rise to digitoxin, gitoxin and gitalin, respectively. Further hydrolysis gives digitoxigenin, gitoxigenin and gitaligenin.

42
Q

biological source and family of european squill

A

fleshy inner bulb scales of white variety
of Urginea maritima (L.) Baker (Liliaceae)