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// Workers AI · dad joke modeWhat did Vinorine say to wine? "You're a grape friend

From Wikipedia, the free encyclopedia
Vinorine
Names
Other names
22-Norajmala-1,19-dien-17α-yl acetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C21H22N2O2/c1-3-12-10-23-16-8-13(12)18-17(23)9-21(20(18)25-11(2)24)14-6-4-5-7-15(14)22-19(16)21/h3-7,13,16-18,20H,8-10H2,1-2H3/b12-3-/t13-,16-,17-,18?,20+,21+/m0/s1
    Key: CLDVMRAEPFQOSD-WEOXKLFPSA-N
  • C/C=C\1/CN2[C@H]3C[C@@H]1C4[C@@H]2C[C@]5([C@@H]4OC(=O)C)C3=NC6=CC=CC=C56
Properties
C21H22N2O2
Molar mass 334.419 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vinorine is an indole alkaloid isolated from Alstonia.[1] It is produced in trees in the Rauvolfia genus by the enzyme vinorine synthase.[2][3][4]

References

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  1. Cao, P.; Liang, Y.; Gao, X.; Li, X. M.; Song, Z. Q.; Liang, G. (2012). "Monoterpenoid indole alkaloids from Alstonia yunnanensis and their cytotoxic and anti-inflammatory activities". Molecules (Basel, Switzerland). 17 (11): 13631–41. doi:10.3390/molecules171113631. PMC 6268798. PMID 23159924.
  2. Bayer A, Ma X, Stockigt J (2004). "Acetyltransfer in natural product biosynthesis--functional cloning and molecular analysis of vinorine synthase". Bioorg. Med. Chem. 12 (10): 2787–95. doi:10.1016/j.bmc.2004.02.029. PMID 15110860.
  3. Stockigt J; Koepke, J; Bayer, A; Linhard, V; Fritzsch, G; Zhang, B; Michel, H; Stöckigt, J (2004). "Vinorine synthase from Rauvolfia: the first example of crystallization and preliminary X-ray diffraction analysis of an enzyme of the BAHD superfamily". Biochim. Biophys. Acta. 1701 (1–2): 129–32. doi:10.1016/j.bbapap.2004.06.011. PMID 15450182.
  4. Ma X, Koepke J, Panjikar S, Fritzsch G, Stockigt J (2005). "Crystal structure of vinorine synthase, the first representative of the BAHD superfamily". J. Biol. Chem. 280 (14): 13576–83. doi:10.1074/jbc.M414508200. PMID 15665331.