General Introduction, Composition, Chemistry and Chemical classes, Bio-sources, Therapeutic uses of : Alkaloids: Vinca


Alkaloids


Introduction

Alkaloids (whose name originally comes from "alkali-like") can react with acids and then form salts, just like inorganic alkalis. These nitrogen atoms can behave like a base in acid-base reactions. Alkaloids are basic in nature because of the presence of lone pair of electrons on nitrogen atom.

Alkaloids are a huge group of naturally occurring organic compounds which contain nitrogen atom (amino or amido in some cases) in their structures. These nitrogen atoms cause alkalinity of these compounds. These nitrogen atoms are usually situated in cyclic ring system. For example, indole alkaloids are those that contain nitrogen atom in indole ring system.

Alkaloids in their pure form are generally colourless, odourless crystalline solids, and sometime they can be yellowish liquids. Quite often they have bitter taste.


Classification of Alkaloids

Generally based on structures, alkaloids can be divided into classes like indoles, quinolines, isoquinolines, pyrrolidines, pyridines, pyrrolizidines, tropanes, and terpenoids and steroids.

Classification of Alkaloids based on the heterocyclic ring system:

Alkaloid Class Ring System Example(s)
Pyridine Pyridine Nicotine, Coniine
Piperidine Piperidine Lobeline, Piperine
Pyrrolidine Pyrrolidine Hygrine
Tropane Tropane Atropine, Cocaine
Quinoline Quinoline Quinine
Isoquinoline Isoquinoline Morphine, Berberine
Indole Indole Strychnine, Reserpine
Imidazole Imidazole Pilocarpine
Purine Purine Caffeine, Theobromine
Quinazoline Quinazoline Vasicine
Phenanthridine Phenanthridine Colchicine
Acridine Acridine Acronycine
Non-heterocyclic None Hordenine

The alkaloids contain one or more number of nitrogen and can exist in some forms of amines, i.e.

Category of Alkaloid Description Examples
Primary Amines
(R-NH₂)
Contain a nitrogen atom bonded to one carbon group and two hydrogen atoms Norephedrine
Secondary Amines
(R₂-NH)
Contain a nitrogen atom bonded to two carbon groups and one hydrogen atom Ephedrine
Tertiary Amines
(R₃-N)
Contain a nitrogen atom bonded to three carbon groups with no hydrogens attached directly to the nitrogen Atropine
Morphine
Quaternary Ammonium Salts
(R₄-N⁺)
Contain a permanently charged nitrogen atom bonded to four carbon groups Tubocurarine

Vinca


Biological Sources of Vinca Alkaloids

Vinca alkaloids are mainly obtained from Catharanthus roseus (Madagascar periwinkle), belongs to the family – Apocynaceae. This is the primary source of vincristine and vinblastine, along with other indole alkaloids such as ajmalicine, serpentine, and catharanthine.


Composition and Chemistry of Vinca

The bioactive components of Vinca are predominantly indole alkaloids. More than 100 alkaloids have been isolated from different parts of the plant, including the leaves, stems, roots, and flowers.

The two most significant and well-studied alkaloids are vincristine and vinblastine, both of which are used in cancer chemotherapy.

Some major and minor alkaloids found in Vinca are: Vincristine, Vinblastine, Vinpocetine, Reserpine, Ajmalicine, Ajmaline, Yohimbine, Vindesine, Catharanthine, Vindolidine, Vindoline, Vindolicine, Catharoseumine, Tabersonine, Catharanthamine, Catharine.

Along with these it also contains carbohydrate, saponins, tannins, flavonoid, steroids, triterpenoid, loganic acid, triterpenoid etc.

process


Chemical Classes of Vinca Alkaloids

The alkaloids derived from Vinca can be categorized into several chemical classes:

Monoterpenoid Indole Alkaloids:

The primary active compounds, vincristine and vinblastine, belong to this class. These are dimeric indole alkaloids characterized by complex structures formed by the coupling of two monomeric units.

Ajmalicine Alkaloids:

These include ajmalicine, also known as raubasine, which has antihypertensive and vasodilatory properties. Ajmalicine is derived from the indole alkaloid pathway.

Catharanthine Alkaloids:

Catharanthine is another monomeric indole alkaloid found in Vinca that plays a crucial role in the biosynthesis of vincristine and vinblastine. It exhibits various pharmacological properties, including antihypertensive and sedative effects.

Flavonoids and Phenolic Compounds:

While not as prominent as alkaloids, Vinca also contains several flavonoids and phenolic compounds, such as quercetin and kaempferol. These compounds contribute to the antioxidant and anti-inflammatory activities of the plant.


Therapeutic Uses of Vinca Alkaloids

Vinca alkaloids are well-known for their therapeutic properties, particularly in cancer treatment:

Alkaloid Therapeutic Uses
Vincristine, Vinblastine Hodgkin’s and Non-Hodgkins lymphoma, Leukamia, Breast cancer, Lung Cancer, testicular cancer, Wilms’ tumour
Ajmalicine, Serpentine Antihypertensive and Vasodilatory effect used in cerebrovascular disorders
Vincamine Enhancing blood flow in the brain and used in cognitive disorders, memory loss and vertigo.
Vinorelbine, Vindesine Lung and Ovarian cancer
Vinburnine Improving cerebral and coronary circulation, used in conditions like coronary artery diseases and peripheral artery diseases.
Other minor alkaloids Used as antimicrobial, Anti-inflammatory, Anti-bacterial and Anti-fungal actions.