2nd Shift Glycosides: Common Sources Flashcards
5 Anthracene/Anthraquinone Glycosides
- Aloes
- Rhubarb
- Cascara sagrada
- Frangula
- Senna
Biological source of aloes
dried latex leaves of Aloe barbadensis (Curacao aloe)
Organoleptic properties of aloes
*color
*odor
*taste
*texture
*color - brownish black opaque mass
*odor - strong odor, resembles iodoform
*taste - bitter
*texture - waxy, somewhat resinous
Chemical constituents of aloes
aloe emodin (free state), aloin (glycoside), emodin oxanthrone, emodin anthrone, emodin anthranol, emodin, isobarbaloin and a resin, aloesin
free state constituent of aloes
aloe emodin
glycoside constituent of aloes
aloin
biological source and family of rhubarb
Rhubarb, rhizomes and roots of Rheum officinale; Polygonaceae
Preparation of rhubarb
rhizomes are collected from 6-10 year old plants and are cut in either longitudinal or transverse manner
Chemical constituents of rhubarb
*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
biological source and family of cascara sagrada
dried bark of Rhamnus purshiana; Rhamnaceae
preparation of cascara sagrada
Bark collected during dry season
Organoleptic Description of Cascara sagrada:
* Color:
* Odor:
* Taste
* Size (Thickness):
* Shape:
* External Bark:
- 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
chemical constituent of cascara sagrada
*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
another name for Deoxybarbaloin
chrysaloin
biological source and family of frangula
dried bark of Rhamnus frangula; Rhamnaceae
preparation of frangula
Like cascara, bark collected during dry season
Chemical constituents of frangula
- Glucofrangulins A and B
- Frangulin A and B
- Also contains Emodin and Chrysophanic acid
Biological source and family of senna
*Dried leaflets of Cassia senna L.
*Cassia acutifolia (Alexandria senna)
*Cascara angustifolia (Tinnevelley senna)
Fam. Leguminoseae
Preparation of senna
Leaves are collected in April and in September and subsequently allowed to dry under the sun, then leaflets are separated thru garbling
Collection month for Senna
April and September
Organoleptic description of alexandria senna based on:
color:
odor:
taste:
size:
shape:
texture:
Pale greyish green
Slight
Mucilaginous and Bitter
L: 2-4 cm W 7-12 mm
Ovate-lanceolate
Thin and brittle
Organoleptic description of tinnevelley senna based on:
color:
odor:
taste:
size:
shape:
texture:
yellowish green
slight
Mucilaginous and Bitter
L: 2.5-5 cm W 3-8 mm
Lanceolate
Thin and flexible
Chemical constituents of Senna
- Sennosides A, B, C and D
- Also contains kaempferol
Method of extraction for sennosides
- 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.
