Catharanthus roseus medical properties; extraction; alkaloids ;vinblastine; vincristine; mechanism of action; side effects.

1. Catharanthus roseus
By
Lena kanaan

3. Introduction
Madagascar periwinkle, native to Madagascar. Other names
Cape periwinkle, and "old-maid".
 ornamental plant.
 evergreen subshrub or herbaceous plant growing to 1 m
tall.
 In the wild, it is an endangered plant.
 the main cause of decline is habitat destruction by slash
and burn agriculture.
 It is also however widely cultivated and is naturalised in
subtropical and tropical areas of the world

4. Medical Properties

5.  Leaves :
o vomitive.
o used in diabetes. enhanced secretion of insulin
o young leaves for stomach cramps
o alkaloids anti-cancer Cytochrome P450
oxidation enzymes Inhibition
o as application to wasp, bee stings.

6. Roots:
o purgative , vermifuge,
depurative , hemostatic.
o for dysentery.
o Antibacterial G+ more sensitive than Gantifungal, antiviral.

7. flowers:
o extract used for eyewash in
infants.
o asthma.

8. Solid-liquid extraction:
Two steps:
1) water extraction:
• Acidified water with HCl is optimum at 3.5 ph
• agitation ,hydrogen peroxide for best yield
• centrifugation
2)organic extraction:
• ethyl acetate

9. Active alkaloids
70 alkaloid

10. Most impotent are:
Vinblastine(VincaleukoblastineVLB)
- Vinleurosine (Leurosine)
- Vinrosidine (Leurosidine)
- Vincristine (Leurocristine,LC)
- 2 semi synthetic derivatives:
vindesine and vinorelbine
-

11. Vinblastine: C46H60N4O13S (velban)
Molecular Weight: 909.0526
More used
More stable
Less active
Less toxic
Hodgkin's disease (glands cancer)
Placenta(choriocarcinoma), Breast, lung, head and neck, and testicular
cancer
Vincristine: C46H56N4O10
(oncovin)
Molecular Weight: 824.97
Less used
Clear liquid
Less stable
More active
More toxic
Acute Leukemia especially in children

12. TLC: chloroform methanol (8:2) solvent
ceric ammonium sulphate reagent
Rf values:
0.77 for vinblastine
0.74 for vincristine
UV detection at 254 nm.

13. Synthesis from vinblastine
vinblastine
Vincristine

14. Mechanism of
Action
Active alkaloids
50
alkaloid

15. vinblastine
act by two mechanisms:
Active alkaloids
 At very low concentrations they suppress microtubule dynamics.
50 alkaloid
 at higher concentrations they reduce microtubule polymer mass.
 Recent findings indicate that they also produce microtubule
fragments by stimulating microtubule minus-end detachment from
their organizing centers.
 Also interfere with glutamic acid metabolism
 interferes with nucleic acid synthesis.
Vincristine mechanism is similar:
Stops division of cells
Enters cell during mitosis and blocks formation of microtubules of the mitotic
spindle during metaphase

16. loss of white blood cells and blood platelets
gastrointestinal problems
depression, muscle cramps
Vinblastine:
Causes birth defects so not used for pregnants
Bone marrow damage is dose limiting factor
Vincristine:
Neurotoxity is dose limiting factor
Causes damage to peripheral NS
hair loss
high blood pressure
vertigo and headaches.

17. summary
Catharanthus roseus:
leaves used in diabetes, alkaloids anti-cancer.
70 Active alkaloids: Vinblastine: More used Less toxic for Hodgkin's disease (glands
cancer), and others while Vincristine less used for Acute Leukemia
Vinblastine mechanism: interferes with nucleic acid synthesis.
Vincristine mechanism is similar.
TLC: chloroform methanol solvent
extraction procedures : Solid-liquid extraction