Catharanthus rosea

The observation that fractions of the rosey periwinkle, Catharanthus rosea, produced severe leukopenia, resulted in the isolation and development of two major anticancer drugs, vincristine and vinblastine. These two complex, dimeric indole-indoline alkaloids are important in the treatment of acute childhood leukemia (vincristine), Hodgkin s disease (vinblastine), and metastatic testicular tumors (vinblastine), and continue to be manufactured today by mass cultivation and processing of their natural source. 

Svoboda GH. Alkaloids of Vinca rosea (Catharanthus rosea).9. 27. Extraction and characterization of leurosidine and leurocristine. Lloydia 1961 24 173-178. 

Figure 3.10a. Effect of nitrogen applied to soil on the alkaloid content of Vinca perenne and Vinca (Catharanthus) rosea in 1972 and 1973. Nitrogen applied one time at 0 week and at the levels 1 = Ig 2 = 2g 3 = 4g 4 = 8g NH4N03/pot.

The discovery of medicinal alkaloids from Catharanthus roseus G. Don (Vinca rosea L.) represents one of the most important introductions of plant products into the cancer chemotherapeutic armamentarium. The relatively unique effects and toxicities of these agents have allowed the design of multiagent chemotherapy programs that have demonstrated sufficient effectiveness to achieve cures even of advanced tumors in many instances. This great accomplishment is possible only because of the inclusion of many different drugs, including the binary Vinca alkaloids. 

The correct botanical name of this pantropical flowering plant is Catharanthus roseus G. Don. A commonly used name is Vinca rosea L. 

Vinblastine (4) and vincristine (5) are closely related indole-dihydroindole dimers (bisindole alkaloids), isolated from Catharanthus roseus (L.) G. Don (formerly known as Vinca rosea L.), the Madagascar periwinkle. Both of these anticancer agents, known as vinca alkaloids in the medical literature, are specific binders of tubulin, leading to tubulin depolymerization and cell cycle arrest in the metaphase stage. 

Other examples of natural drugs may be pointed out streptozotocin (from streptomyces achromogenes), bleomycin (from streptomyces verticillus), adriamy-cin and daunomycin (from streptomyces pencetius), mitomycin C (from streptomyces caesipitosus), vincristine, vinblastine and vindoline (from catharanthus roseus or vinca rosea L.). 

The Madagascar periwinkle Catharanthus roseus (= Vinca rosea) (Apocynaceae) is a small herb or shrub originating in Madagascar, but now common in the tropics and widely cultivated as an ornamental for its shiny dark green leaves and pleasant five-lobed flowers. Drug material is now cultivated in many parts of the world, including the USA, Europe, India, Australia, and South America. 

Alkaloid from Vinca rosea (Catharanthus roseus) (Apocynaceae)... 

MADAGASCAR PERIWINKLE -- Catharanthus roseus, formerly Vinca rosea. Family Apocynaceae (Dogbane family). 

A number of alkaloids with the aspidospermine skeleton occur in the genus Vinca and are dealt with in detail in Chapter 12. They include the very important base vindoline (CIII) which not only occurs as the free base in Vinca rosea (= Lochnera rosea = Catharanthus roseus) but also as part of the dimeric alkaloids vinblastine (vincaleucoblastine) and leurosine, whereas the Aa-formyl analog, CIV, forms part of the dimeric alkaloid leurocristine (5, 72a). These dimeric alkaloids have been used successfully for the treatment of certain forms of cancer in man (5). Vindolinine (CVI) has also been isolated from V. rosea and its dihydro-decarbomethoxy derivative, tuboxenin (CVI-A), which is the parent member of the series, occurs in a Pleiocarpa species (53). ( + )-Vincadif-formine (XCIII, 6, 74) has already been mentioned as the racemic form of (— )-6,7-dihydrotabersonine (Section II, O). It has been found in V. difformis and in Rhazya stricta (51b) where the (+) form also occurs. 

NSC 49842 Velban Velbe ) is one of the vinca alkaloids from Vinca rosea (Catharanthus roseus) (Apocynaceae). It is a cytotoxic ANTICANCER AGENT used by injection for acute leukaemias, lymphomas and some solid tumours, vinblastine sulfate vinblastine, vincaleucoblastine vinblastine, vincaleukoblastine vinblastine. 

Vinblastine sulfate is the nonproprietary name assigned by the United States Adopted Names Council to the compound originally named vinca-leukoblastine sulfate1 s 3. It is the 1 1 sulfate salt of an alkaloid obtained from the plant Vinca rosea Linn. (Catharanthus roseus G. Don) of the family Apocynaceae, better known as Madagascar periwinkle. Frequently the name is abbreviated to VLB sulfate. It is also identified by the code numbers NSC-49812 and 29060-LE4. The elucidation of the molecular structure, stereochemistry, and absolute configuration of this interesting compound is fully documented in the literature5 7 8. 

Catharanthus roseus G.Don, (syn. Vinca rosea (L.), Lochnera rosea (L.), Reichb.), family Apocynaceae, is a perennial herb, 50-80 cm high. The flowers are white, pink or red. The plant originates from Madagascar and is now pantropic in its distribution. It is cultivated for two purposes as an ornamental... 

Fig. 15. Catharanthus roseus (L.), G.Don =VinM rosea lj.=Lochnera rosea L.Reichb.) Culti vation in the Tuticorin district, Southern India. 

Table I, Crown Gall Cells of Catharanthus roseus (Vinca rosea L.)...

In 1959 a series of bisindole alkaloids were isolated from Vinca rosea L. Catharanthus roseus G. Don). Of signal importance have been vinblastine (169) (= vincaleukoblastine) and vincristine (170) (= leurocristine), both of which show anti-tumour activity (see Section 18, p. 333). Structurally clarified also are leurosidine (= vinrosidine), leurosine, pleurosine, and isoleurosine , while only one half of Catharine is known. 

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