Raucaffrinoline

Raucaffrinoline
Names
IUPAC name
[(1R,10S,12S,13R,14S,16S,18R)-13-(hydroxymethyl)-14-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C21H24N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,10,12-13,16-18,20,24H,7-9H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1
    Key: XIMPCXFLDSKALH-FXRWJBKJSA-N
  • C[C@H]1[C@@H]([C@@H]2C[C@@H]3N1[C@@H]4C2[C@H]([C@@]5(C4)C3=NC6=CC=CC=C56)OC(=O)C)CO
Properties
C21H24N2O3
Molar mass 352.434 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Raucaffrinoline is an indole alkaloid isolated from the leaves of various plants in the Rauvolfia family, such as Rauvolfia yunnanensis.[1][2][3][4]

References

  1. ^ Khan MA, Siddiqui S (February 1972). "Isolation and structure of raucaffrinoline--a new alkaloid from Rauwolfia caffra sonder". Experientia. 28 (2): 127–128. doi:10.1007/BF01935708. PMID 5020328.
  2. ^ Rosenthal C, Mueller U, Panjikar S, Sun L, Ruppert M, Zhao Y, et al. (December 2006). "Expression, purification, crystallization and preliminary X-ray analysis of perakine reductase, a new member of the aldo-keto reductase enzyme superfamily from higher plants". Acta Crystallographica. Section F, Structural Biology and Crystallization Communications. 62 (Pt 12): 1286–1289. doi:10.1107/S174430910605041X. PMC 2225361. PMID 17142919.
  3. ^ Cao P, Liang Y, Gao X, Li XM, Song ZQ, Liang G (November 2012). "Monoterpenoid indole alkaloids from Alstonia yunnanensis and their cytotoxic and anti-inflammatory activities". Molecules. 17 (11): 13631–13641. doi:10.3390/molecules171113631. PMC 6268798. PMID 23159924.
  4. ^ Geng CA, Liu XK (September 2013). "Five new indole alkaloids from the leaves of Rauvolfia yunnanensis". Fitoterapia. 89: 42–47. doi:10.1016/j.fitote.2013.05.017. PMID 23707746.
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