Vindoline

Last updated
Vindoline
Vindoline.svg
Names
IUPAC name
Methyl 3β,4β-dihydroxy-16-methoxy-1-methyl-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3α-carboxylate
Systematic IUPAC name
Methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.871 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-558-0
PubChem CID
UNII
  • InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
    Key: CXBGOBGJHGGWIE-ACSXSLCXSA-N
  • InChI=1/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
    Key: CXBGOBGJHGGWIE-ACSXSLCXBW
  • CC[C@@]12C=CCN3[C@@H]1[C@@]4(CC3)c5ccc(cc5N([C@H]4C([C@@H]2OC(=O)C)(C(=O)OC)O)C)OC
Properties
C25H32N2O6
Molar mass 456.539 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vindoline is a chemical precursor to vinblastine. [1] Vindoline is formed through biosynthesis from Tabersonine.

See also

Related Research Articles

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Bansal, Raj K. (2003). A Textbook of Organic Chemistry. New Age International Limited. p. 644. ISBN 978-81-224-1459-2.

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<i>Catharanthus</i> Genus of flowering plants

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".

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<span class="mw-page-title-main">Pronucleus</span> Nucleus of a sperm or an egg cell during fertilization

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<span class="mw-page-title-main">Vinblastine</span> Chemotherapy medication

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.

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<i>Catharanthus roseus</i> Species of flowering plant in the family Apocynaceae

Catharanthus roseus, commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, 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. It was formerly included in the genus Vinca as Vinca rosea.

<i>Vinca</i> alkaloid

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<span class="mw-page-title-main">Vindesine</span> Chemical compound

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.

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<span class="mw-page-title-main">Vincoline</span> Chemical compound

Vincoline is an alkaloid isolated from Catharanthus roseus. In a mouse model, it has been found to stimulate insulin secretion.

<span class="mw-page-title-main">Tabersonine</span> Chemical compound

Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also in the genus Voacanga. Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine. The enzyme leading to its formation is currently unknown. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

<span class="mw-page-title-main">16-Hydroxytabersonine</span> Chemical compound

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.

<span class="mw-page-title-main">Bis(cyclopentadienyl)titanium(III) chloride</span> Chemical compound

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.

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References

  1. Liu, J; Zhu, J; Tang, L; Wen, W; Lv, S; Yu, R (2014). "Enhancement of vindoline and vinblastine production in suspension-cultured cells of Catharanthus roseus by artemisinic acid elicitation". World Journal of Microbiology and Biotechnology. 30 (1): 175–80. doi:10.1007/s11274-013-1432-z. PMID   23864440. S2CID   7350499.