Vinca rosea periwinkles

Vinca alkaloids (vincristine, vinblastine, vindesine) are derived from the periwinkle plant (Vinca rosea), they bind to tubulin and inhibit its polymerization into microtubules and spindle formation, thus producing metaphase arrest. They are cell cycle specific and interfere also with other cellular activities that involve microtubules, such as leukocyte phagocytosis, chemotaxis, and axonal transport in neurons. Vincristine is mainly neurotoxic and mildly hematotoxic, vinblastine is myelosuppressive with veiy low neurotoxicity whereas vindesine has both, moderate myelotoxicity and neurotoxicity. 

The discovery of vinblastine and vincristine is one of the most intriguing examples of serendipity in scientihc research in recent years. In 1952, the Canadian medical researcher Robert Laing Noble (1910-90) received a package from his brother. Dr. Clark Noble, containing 25 leaves from the Madagascar periwinkle plant. Vinca rosea. Clark had received the leaves from one of his patients in Jamaica, who said that natives on the island often used the plant to control their diabetes when insulin was not available. Clark, who was retired, suggested that his brother study the plant for possible use as a drug for the treatment of diabetes. 

The contractile proteins of the spindle apparatus must draw apart the replicated chromosomes before the cell can divide. This process is prevented by the so-called spindle poisons (see also colchicine, p. 316) that arrest mitosis at metaphase by disrupting the assembly of microtubules into spindle threads. The vinca alkaloids, vincristine and vinblastine (from the periwinkle plant. Vinca rosea) exert such a cell-cycle-specific effect. Damage to the nervous system is a predicted adverse effect arising from injury to microtubule-operated axonal transport mechanisms. 

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. 

Vinblastine and vincristine are alkaloids isolated from plants of the periwinkle family (Vinca rosea). These compounds cause cells to stop at metaphase and inhibit assembly of microtubules, and likewise, failure of mitotic spindle formations. They inhibit synthesis of nucleic acids and proteins. 

Vinblastine is an alkaloid derived from the periwinkle plant Vinca rosea. Its mechanism of action involves inhibition of tubulin polymerization, which disrupts assembly of microtubules, an important part of the cytoskeleton and the mitotic spindle. This inhibitory effect results in mitotic arrest in metaphase, bringing cell division to a halt, which then leads to cell death. Vinblastine and other vinca alkaloids are metabolized by the liver P450 system, and the majority of the drug is excreted in feces via the biliary system. As such, dose modification is required in the setting of liver dysfunction. The main adverse effects are outlined in Table 54-4, and they include nausea and vomiting, bone marrow suppression, and alopecia. This agent is also a potent vesicant, and care must be taken in its administration. It has clinical activity in the treatment of Hodgkin s... 

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. 

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

Vincristine [vin KRIS teen] and vinblastine [vin BLAST een] are structurally-related compounds derived from the periwinkle plant, Vinca rosea. They are therefore referred to as the vinca alkaloids. A structurally related new (and less toxic) agent, vinorelbine [vye NO rel been] shows promise in the treatment of advanced non-small cell lung cancer. 

The vinca alkaloids, vincristine and vinblastine (from the periwinkle plant, Vinca rosea), inhibit the polymerization of tubulin subunits into microtubuli. Damage to the nervous system is a predicted adverse effect arising from injury to microtubule-operated axonal transport mechanisms. 

Thomas Jefferson, Samuel Johnson Immanuel Kant Raumoljia serpentina (Apocynaceae) Ravmolfia serpentina (Apocynaceae) Vinca rosea (Madagascar periwinkle) (Apocynaceae)... 

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. 

Vinca alkaloids (vincristine, vinblastine, vinorelbine) are derived from the periwinkle plant (Vinca rosea). These agents work by binding to tubulin at a site different than colchicine or paclitaxel. They block polymerization, which prevents the formation of the mitotic spindle, and are used as antineoplastic agents. Taxanes produce a stabilization of microtubules similar to colchicine, but by a different mechanism, and also halt cells in metaphase. Paclitaxel (taxol) is the taxane used clinically. It is derived from the bark of the pacific yew. Taxol disrupts several microtubule-based functions as completely as inhibitors of polymerization, emphasizing the importance of assembly/disassembly balance in microtubule function. Recently, it has been found that paclitaxel also binds to and inhibits the function of a protein called bcl-2, an inhibitor of one or more pathways involved in mediating apoptosis. PaclitaxeTs interference with this function promotes apoptosis in addition to its microtubule-related inhibition of cell division. 

First studies were undertaken with Periwinkle plants from Jamaica. The roots, stems, and leaves all contain active material the leaves contain the highest proportion of activity, but in the seeds almost no activity is found.Today we know that four of the pure alkaloids, crystallised from extracts of Vinca rosea plants, namely vinblastine [(169), = vincaleukoblastine)], vincristine [(170), = leurocristine], vinleurosine [= leurosine, (183)], and vinrosidine [= leurosidine, (181)] show good effects in suppression of tumour growth. In the last decade about fifty-five alkaloids have been found in Vinca rosea extracts and tested for their pharmacological effects. Besides the four mentioned none of the... 

Vinca alkaloids are extracted from the periwinkle plant. Vinca rosea, although newer ones are semi-synthetic. They bind to tubulin and prevent its polymerization into microtubules. Microtubules form the spindle during mitosis, so vinca alkaloids halt mitosis at a certain stage. 

Vinblastine is an alkaloid derived from Vinca rosea, the periwinkle plant. Its mechanism of action involves depolymerization of microtubules, which are an important part of the cytoskeleton and the mitotic spindle. The drug binds specifically to the microtubular protein tubulin in dimeric form the drug-tubulin complex joins to the forming end of... 

Initial methods for the isolation of vinblastine from the periwinkle plants (vinca rosea) had been described (5,7,23-25) and well documented in several texts including the previous profile of vinblastine sulfate (12). Isolation of vinblastine and vincristine from Catharanthus roseus continues to receive attention, and several procedures have been reported (mainly in the patent literature) for the isolation and separation of these alkaloids (24-29). Extracts of Catharanthus roseus have been found to contain N-demethylvinblastine and this can be used to prepare vincristine by formylating the alkaloid mixture before separation and purification (30). 

The compounds selected for evaluation as potential anticancer agents could be of natural or synthetic origin. Compounds of natural origin have often provided new leads in the novelty of structures with anticancer activity. Mans et al. have enlisted several examples of naturally derived anticancer compounds [35]. For example, vincristine derived from the periwinkle plant Vinca rosea, etoposide is derived from the mandrake plant Podophyllum peltatum, and taxol, which is... 

Periwinkle (Vinca rosea), 300ft-c Periwinkle (V. rosea), 86ft-c... 

Periwinkle. 1. Tropical periwinkle small, 40-80 cm high, subshrub with glossy leaves and violet, red, or white flowers (Apocynaceae). The tropical P. (also Catharanthus roseus, previously named as Vinca rosea) was originally indigenous to Madagascar but is... 

The biosynthesis and chemistry of alkaloids have been discussed in a recent book on natural products (Hendrickson, 1965). Hendrickson has pointed out the important contributions made to structural chemistry by instrumental methods of analysis such as UV, IR, NMR, and ORD spectroscopy. One of the alkaloids discussed in which reference to the use of infrared spectroscopy was made was vindoline (CIII) (a compound isolated from periwinkles Vinca rosea in a search for anticancer agents). Dihydrovindoline hydrochloride on mild pyrolysis yielded a ketone C21H28-N2O2. The infrared spectrum of this compound showed absorption at 1709cm", which indicated a cyclohexanone. This result was used, together with other information, in determining the total structure. 

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