Vincoline

Last updated
Vincoline
Vincoline.svg
Names
IUPAC name
Methyl (2β,3β,5α,12β,19α,20S)-2-hydroxy-6,7-didehydro-3,20-epoxyaspidospermidine-3-carboxylate
Preferred IUPAC name
Methyl (3aS,3a1S,4S,6R,6aS,11bR)-6a-hydroxy-4-methyl-6a,7,12,13-tetrahydro-1H,3a1H,4H,6H-3a,6-methanoindolizino[1′,8′:4,5,6]oxepino[3,4-b]indole-6-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1
    Key: YOQNZWXFGROKGY-KVKBDHCBSA-N
  • InChI=1/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1
    Key: YOQNZWXFGROKGY-KVKBDHCBBE
  • C[C@H]1[C@]23C[C@@](O1)([C@]4([C@@]5([C@H]2N(CC5)CC=C3)c6ccccc6N4)O)C(=O)OC
Properties
C21H24N2O4
Molar mass 368.433 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vincoline is an alkaloid isolated from Catharanthus roseus . [1] In a mouse model, it has been found to stimulate insulin secretion. [2]

Related Research Articles

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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 species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but grown elsewhere as an ornamental and medicinal plant. 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.

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Enteroendocrine cell

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Dauricine Chemical compound

Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid. It has been isolated from the Asian vine Menispermum dauricum, commonly known as Asian moonseed, and the North American vine Menispermum canadense, commonly known as Canadian moonseed. Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so. Dauricine has been studied in vitro for its potential to inhibit cancer cell growth and to block cardiac transmembrane Na+, K+, and Ca2+ ion currents.

Canadine Chemical compound

(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.

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Akuammicine Alkaloid

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.

References

  1. Aynilian, GH; Weiss, SG; Cordell, GA; Abraham, DJ; Crane, FA; Farnsworth, NR (1974). "Catharanthus alkaloids. XXIX. Isolation and structure elucidation of vincoline". Journal of Pharmaceutical Sciences. 63 (4): 536–8. doi:10.1002/jps.2600630409. PMID   4828700.
  2. Yao, XG; Chen, F; Li, P; Quan, L; Chen, J; Yu, L; Ding, H; Li, C; Chen, L; Gao, Z; Wan, P; Hu, L; Jiang, H; Shen, X (2013). "Natural product vindoline stimulates insulin secretion and efficiently ameliorates glucose homeostasis in diabetic murine models". Journal of Ethnopharmacology. 150 (1): 285–97. doi:10.1016/j.jep.2013.08.043. PMID   24012527.