Catharanthus roseus | |
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Scientific classification | |
Kingdom: | Plantae |
Clade: | Tracheophytes |
Clade: | Angiosperms |
Clade: | Eudicots |
Clade: | Asterids |
Order: | Gentianales |
Family: | Apocynaceae |
Genus: | Catharanthus |
Species: | C. roseus |
Binomial name | |
Catharanthus roseus | |
Synonyms | |
(See also Synonyms section) |
Catharanthus roseus, commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, [2] is a perennial species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but is grown elsewhere as an ornamental and medicinal plant, and now has a pantropical distribution. It is a source of the drugs vincristine and vinblastine, used to treat cancer. [3] It was formerly included in the genus Vinca as Vinca rosea.
It has many vernacular names among which are arivotaombelona or rivotambelona, tonga, tongatse or trongatse, tsimatiririnina, and vonenina. [4]
Two varieties are recognized
Catharanthus roseus is an evergreen subshrub or herbaceous plant growing 1 m (39 in) tall. The leaves are oval to oblong, 2.5–9 cm (1.0–3.5 in) long and 1–3.5 cm (0.4–1.4 in) wide, glossy green, hairless, with a pale midrib and a short petiole 1–1.8 cm (0.4–0.7 in) long; they are arranged in opposite pairs. The flowers range from white with a yellow or red center to dark pink with a darker red center, with a basal tube 2.5–3 cm (1.0–1.2 in) long and a corolla 2–5 cm (0.8–2.0 in) diameter with five petal-like lobes. The fruit is a pair of follicles 2–4 cm (0.8–1.6 in) long and 3 mm (0.1 in) wide. [12] [13] [14] [15] [</ref>
In its natural range along the dry coasts of southern Madagascar, Catharanthus roseus is considered weedy and invasive, often self-seeding prolifically in disturbed areas along roadsides and in fallow fields. [16] [17] It is also, however, widely cultivated and is naturalized in subtropical and tropical areas of the world such as Australia, Bangladesh, India, Malaysia, Pakistan, and the United States. [12] It is so well adapted to growth in Australia that it is listed as a noxious weed in Western Australia and the Australian Capital Territory, [18] and also in parts of eastern Queensland. [19]
As an ornamental plant, it is appreciated for its hardiness in dry and nutritionally deficient conditions, popular in subtropical gardens where temperatures never fall below 5–7 °C (41–45 °F), and as a warm-season bedding plant in temperate gardens. It is noted for its long flowering period, throughout the year in tropical conditions, and from spring to late autumn, in warm temperate climates. Full sun and well-drained soil are preferred. Numerous cultivars have been selected, for variation in flower colour (white, mauve, peach, scarlet, and reddish-orange), and also for tolerance of cooler growing conditions in temperate regions.
Notable cultivars include 'Albus' (white flowers), 'Grape Cooler' (rose-pink; cool-tolerant), the Ocellatus Group (various colours), and 'Peppermint Cooler' (white with a red centre; cool-tolerant). [12]
In the U.S. it often remains identified as "Vinca" although botanists have shifted its identification and it often can be seen growing along roadsides in the south.
In the United Kingdom it has gained the Royal Horticultural Society's Award of Garden Merit [20] (confirmed 2017). [21]
In Ayurveda (Indian traditional medicine) the extracts of its roots and shoots, although poisonous, are used against several diseases. In traditional Chinese medicine, extracts from it have been used against numerous diseases, including diabetes, malaria, and Hodgkin's lymphoma. [22] [13] In the 1950s, vinca alkaloids, including vinblastine and vincristine, were isolated from Catharanthus roseus while screening for anti-diabetic drugs. [23] This chance discovery led to increased research into the chemotherapeutic effects of vinblastine and vincristine. Conflict between historical indigenous use, and a patent from 2001 on C. roseus-derived drugs by western pharmaceutical companies, without compensation, has led to accusations of biopiracy. [24]
Vinblastine and vincristine, chemotherapy medications used to treat several types of cancers, are found in the plant [25] [26] [27] [28] and are biosynthesised from the coupling of the alkaloids catharanthine and vindoline. [29] The newer semi-synthetic chemotherapeutic agent vinorelbine, used in the treatment of non-small-cell lung cancer, [27] [30] can be prepared either from vindoline and catharanthine [27] [31] or from the vinca alkaloid leurosine, [32] in both cases via anhydrovinblastine. [31] The insulin-stimulating vincoline has been isolated from the plant. [33] [34]
Despite the medical importance and wide use, the desired alkaloids (vinblastine and vincristine) are naturally produced at very low yields. Additionally, it is complex and costly to synthesize the desired products in a lab, resulting in difficulty satisfying the demand and a need for overproduction. [35] Treatment of the plant with phytohormones, such as salicylic acid [36] and methyl jasmonate, [37] [38] have been shown to trigger defense mechanisms and overproduce downstream alkaloids. Studies using this technique vary in growth conditions, choice of phytohormone, and location of treatment. Concurrently, there are various efforts to map the biosynthetic pathway producing the alkaloids to find a direct path to overproduction via genetic engineering. [39] [40]
C. roseus is used in plant pathology as an experimental host for phytoplasmas. [41] This is because it is easy to infect with a large majority of phytoplasmas, and also often has very distinctive symptoms such as phyllody and significantly reduced leaf size. [42]
In 1995 and 2006 Malagasy agronomists and American political ecologists studied the production of Catharanthus roseus around Fort Dauphin and Ambovombe and its export as a natural source of the alkaloids used to make vincristine, vinblastine and other vinca alkaloid cancer drugs. Their research focused on the wild collection of periwinkle roots and leaves from roadsides and fields and its industrial cultivation on large farms. [43] [44] [45]
Rosinidin is the pink anthocyanidin pigment found in the flowers of C. roseus. [46] Lochnericine is a major alkaloid in roots. [47]
C. roseus can be extremely toxic if consumed orally by humans, and is cited (under its synonym Vinca rosea) in the Louisiana State Act 159. All parts of the plant are poisonous. On consumption, symptoms consist of mild stomach cramps, cardiac complications, hypotension, systematic paralysis eventually leading to death. [48]
According to French botanist Pierre Boiteau, its poisonous properties are made known along generations of Malagasy people as a poison consumed in ordeal trials, even before the tangena fruit was used. This lent the flower one of its names vonenina, from Malagasy : vony enina meaning "flower of remorse". [49]
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 similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. Rarer still, they may contain elements such as phosphorus, chlorine, and bromine.
Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison. Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.
Catharanthus is a genus of flowering plants in the family Apocynaceae. Like the genus Vinca, they are known commonly as periwinkles. There are eight known species. Seven are endemic to Madagascar, though one, C. roseus, is widely naturalized around the world. The eighth species, C. pusillus, is native to India and Sri Lanka. The name Catharanthus comes from the Greek for "pure flower".
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 disease, neuroblastoma, and small cell lung cancer among others. It is given intravenously.
Vinca 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.
Fort-Dauphin is a city on the southeast coast of Madagascar. It is the capital of the Anosy Region and of the Taolagnaro District. It has been a port of local importance since the early 1500s. A new port, the Ehoala Port was built in 2006–2009. Fort-Dauphin was the first French settlement in Madagascar.
Vinorelbine (NVB), sold under the brand name Navelbine among others, is a chemotherapy medication used to treat a number of types of cancer. This includes breast cancer and non-small cell lung cancer. It is given by injection into a vein or by mouth.
Vinblastine (VBL), sold under the brand name Velban among others, is a chemotherapy medication, typically used with other medications, to treat a number of types of cancer. This includes Hodgkin's lymphoma, non-small-cell lung cancer, bladder cancer, brain cancer, melanoma, and testicular cancer. It is given by injection into a vein.
Vinca alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus and other vinca plants. They block beta-tubulin polymerization in a dividing cell.
Vindesine, also termed Eldisine, is a semisynthetic vinca alkaloid derived from the flowering plant Catharanthus roseus. Like the natural and semisynthetic vinca alkaloids derived from this plant, vindesine is an inhibitor of mitosis that is used as a chemotherapy drug. By inhibiting mitosis, vinedsine blocks the proliferation of cells, particularly the rapidly proliferation cells of certain types of cancer. It is used, generally in combination with other chemotherapeutic drugs, in the treatment of various malignancies such as leukaemia, lymphoma, melanoma, breast cancer, and lung cancer.
Ambovombe-Androy, or just Ambovombe, is a city in the far south of Madagascar, and the capital of the Androy region. Ambovombe has now acquired city status with an officially estimated population in 2018 of 114,230.
A mitotic inhibitor, microtubule inhibitor, or tubulin inhibitor, is a drug that inhibits mitosis, or cell division, and is used in treating cancer, gout, and nail fungus. These drugs disrupt microtubules, which are structures that pull the chromosomes apart when a cell divides. Mitotic inhibitors are used in cancer treatment, because cancer cells are able to grow through continuous division that eventually spread through the body (metastasize). Thus, cancer cells are more sensitive to inhibition of mitosis than normal cells. Mitotic inhibitors are also used in cytogenetics, where they stop cell division at a stage where chromosomes can be easily examined.
Strictosidine synthase (EC 4.3.3.2) is an enzyme in alkaloid biosynthesis that catalyses the condensation of tryptamine with secologanin to form strictosidine in a formal Pictet–Spengler reaction:
Catharanthus trichophyllus is a species of flowering plant in the family Apocynaceae. It is endemic to Madagascar, where it is most common in northern regions.
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.
Vindoline is a chemical precursor to vinblastine. Vindoline is formed through biosynthesis from Tabersonine.
Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids. Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.
16-Hydroxytabersonine is a terpene indole alkaloid produced by the plant Catharanthus roseus. The metabolite is an intermediate in the formation of vindoline, a precursor needed for formation of the pharmaceutically valuable vinblastine and vincristine. 16-hydroxytabersonine is formed from the hydroxylation of tabersonine by tabersonine 16-hydroxylase (T16H). Tabersonine 16-O-methyltransferase (16OMT) methylates the hydroxylated 16 position to form 16-methoxytabersonine.
Bis(cyclopentadienyl)titanium(III) chloride, also known as the Nugent–RajanBabu reagent, is the organotitanium compound which exists as a dimer with the formula [(C5H5)2TiCl]2. It is an air sensitive green solid. The complex finds specialized use in synthetic organic chemistry as a single electron reductant.
Catharanthine and vindoline are terpenoid indole alkaloids naturally produced within the Madagascar periwinkle plant whose dimerization produces the anti-cancer drugs vinblastine and vincristine. The precursor of catharanthine and vindoline is strictosidine, the common precursor of all indole alkaloids. The localization of catharanthine and vindoline within the plant tissue has been heavily studied in recent years with conflicting results. The dimerization of catharanthine and vindoline to form vinblastine and vincristine is catalyzed by a peroxidase and a reductase, and includes several intermediate compounds.
https://link.springer.com/chapter/10.1007/978-3-319-51620-2_7