''Vinca'' alkaloids are a set of
anti-mitotic and
anti-microtubule alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of simila ...
agents originally derived from the periwinkle plant ''
Catharanthus roseus
''Catharanthus roseus'', commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a species of flowering plant in the family Apocynaceae. It is native and endemic to M ...
'' (
basionym
In the scientific name of organisms, basionym or basyonym means the original name on which a new name is based; the author citation of the new name should include the authors of the basionym in parentheses. The term "basionym" is used in both bota ...
''Vinca rosea'') and other ''
vinca
''Vinca'' (; Latin: ''vincire'' "to bind, fetter") is a genus of flowering plants in the family Apocynaceae, native to Europe, northwest Africa and southwest Asia. The English name periwinkle is shared with the related genus ''Catharanthus'' (an ...
'' plants. They block
beta-tubulin polymerization in a dividing cell.
Sources
The Madagascan periwinkle ''
Catharanthus roseus
''Catharanthus roseus'', commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a species of flowering plant in the family Apocynaceae. It is native and endemic to M ...
'' L. is the source for a number of important natural products, including
catharanthine
Catharanthine is a terpene indole alkaloid produced by the medicinal plant ''Catharanthus roseus'' and ''Tabernaemontana divaricata''. Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown ...
and
vindoline
Vindoline is a chemical precursor to vinblastine.
Vindoline is formed through biosynthesis from Tabersonine.
See also
* Lochnericine
Lochnericine is a major monoterpene indole alkaloid present in the roots of ''Catharanthus roseus''. It is al ...
and the vinca alkaloids it produces from them:
leurosine and the
chemotherapy
Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemother ...
agents
vinblastine and
vincristine
Vincristine, also known as leurocristine and marketed under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer. This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's ...
, all of which can be obtained from the plant.
The newer
semi-synthetic chemotherapeutic agent
vinorelbine is used in the treatment of
non-small-cell lung cancer
Non-small-cell lung cancer (NSCLC) is any type of epithelial lung cancer other than small-cell lung carcinoma (SCLC). NSCLC accounts for about 85% of all lung cancers. As a class, NSCLCs are relatively insensitive to chemotherapy, compared to s ...
and is not known to occur naturally. However, it can be prepared either from vindoline and catharanthine
or from leurosine,
in both cases by synthesis of anhydrovinblastine, which "can be considered as the key intermediate for the synthesis of vinorelbine."
The leurosine pathway uses the
Nugent–RajanBabu reagent in a highly
chemoselective de-oxygenation of leurosine.
Anhydrovinblastine is then reacted sequentially with
''N''-bromosuccinimide and
trifluoroacetic acid
Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with ...
followed by
silver tetrafluoroborate to yield vinorelbine.
Applications
''Vinca'' alkaloids are used in
chemotherapy
Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemother ...
for cancer. They are a class of
cell cycle
The cell cycle, or cell-division cycle, is the series of events that take place in a cell that cause it to divide into two daughter cells. These events include the duplication of its DNA (DNA replication) and some of its organelles, and sub ...
–specific
cytotoxic drugs
Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemotherap ...
that work by inhibiting the ability of cancer cells to divide: Acting upon tubulin, they prevent it from forming into
microtubules
Microtubules are polymers of tubulin that form part of the cytoskeleton and provide structure and shape to eukaryotic cells. Microtubules can be as long as 50 micrometres, as wide as 23 to 27 nm and have an inner diameter between 11 a ...
, a necessary component for
cellular division. The ''vinca'' alkaloids thus prevent microtubule ''polymerization'', as opposed to the mechanism of action of
taxane
Taxanes are a class of diterpenes. They were originally identified from plants of the genus '' Taxus'' (yews), and feature a taxadiene core. Paclitaxel (Taxol) and docetaxel (Taxotere) are widely used as chemotherapy agents. Cabazitaxel was FDA ...
s.
''Vinca'' alkaloids are now produced
synthetically and used as drugs in cancer therapy and as immunosuppressive drugs. These compounds include vinblastine, vincristine,
vindesine, and vinorelbine. Additional researched ''vinca'' alkaloids include
vincaminol
Vincaminol (C20H26N2O2) is a chemical that is a part of the Vinca alkaloid group, which were discovered in the 1950s by a Canadian scientist and are derived from ''Vinca minor'' (periwinkle). Vincaminol is not as well known as some of the other Vi ...
,
vineridine
Vineridine (vineridin) is a vinca alkaloid
''Vinca'' alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant ''Catharanthus roseus'' (basionym ''Vinca rosea'') and other '' vinca'' ...
, and
vinburnine.
Vinpocetine is a semi-synthetic
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...
of
vincamine (sometimes described as "a
synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to:
Science
* Synthetic chemical or compound, produced by the process of chemical synthesis
* Synthetic ...
ethyl ester of apovincamine").
Minor ''vinca'' alkaloids include minovincine, methoxyminovincine, minovincinine, vincadifformine, desoxyvincaminol, and vincamajine.
References
{{Reflist
External links
Chemotherapeutic ''vinca'' alkaloids
Mitotic inhibitors
Plant toxins