Codinaeopsin

Codinaeopsin
Names
IUPAC name
5-((1H-indol-3-yl)methyl)-3-((1R,2R,4aS,6R,8S,8aS)-2-((E)-but-2-en-2-yl)-4a,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-hydroxy-1H-pyrrol-2(5'H)-one
Identifiers
3D model (JSmol)
  • InChI=1S/C32H40N2O3/c1-7-19(3)26-21(5)14-31(6)13-18(2)12-20(4)28(31)27(26)29(35)24-16-32(37,34-30(24)36)15-22-17-33-25-11-9-8-10-23(22)25/h7-11,14,16-18,20,26-28,33,37H,12-13,15H2,1-6H3,(H,34,36)/b19-7+/t18-,20+,26-,27-,28+,31+,32?/m1/s1
    Key: FFIWOIAVVDGNHZ-ZQXRKGDHSA-N
  • C/C=C(\C)/[C@H]1[C@H]([C@@H]2[C@H](C[C@H](C[C@]2(C=C1C)C)C)C)C(=O)C3=CC(NC3=O)(CC4=CNC5=CC=CC=C54)O
Properties
C32H40N2O3
Molar mass 500.683 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Codinaeopsin is an antimalarial isolated from a fungal isolate found in white yemeri trees (Vochysia guatemalensis) in Costa Rica. It is reported to have bioactivity against Plasmodium falciparum with an IC50 = 2.3 μg/mL (4.7 μM). Pure codinaeopsin was reported to be isolated with a total yield of 18 mg/mL from cultured fungus.[1] The biosynthesis of codinaeopsin involves a polyketide synthase-nonribosomal peptide synthetase (PKS-NRPS) hybrid.

  1. ^ Kontnik, Renee; Clardy, Jon (2008). "Codinaeopsin, an Antimalarial Fungal Polyketide". Org. Lett. 10 (18): 4149–4151. doi:10.1021/ol801726k. PMC 2626159. PMID 18698786.