Bruceolide

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Bruceolide
Chemical Structure of Bruceolide.png
Names
IUPAC name
Methyl 3,11β,12α,15β-tetrahydroxy-2,16-dioxo-13,20-epoxy-13β-picras-3-en-21-oate
Preferred IUPAC name
Methyl (1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-1,2,4,9-tetrahydroxy-8,11a-dimethyl-5,10-dioxo-1,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-2H-3,3a1-(epoxymethano)phenanthro[10,1-bc]pyran-3-carboxylate
Identifiers
3D model (JSmol)
  • InChI=1S/C21H26O10/c1-7-8-4-10-20-6-30-21(18(28)29-3,15(20)13(25)17(27)31-10)16(26)12(24)14(20)19(8,2)5-9(22)11(7)23/h8,10,12-16,23-26H,4-6H2,1-3H3/t8-,10+,12+,13+,14+,15+,16-,19-,20+,21-/m0/s1
    Key: YLWQKYSDNGHLAO-PWRINDRCSA-N
  • CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)O)(OC5)C(=O)OC)O)O)C)O
Properties
C21H26O10
Molar mass 438.429 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bruceolide is a quassinoid that has been isolated from Bischofia javanica. Synthetic derivatives have shown in vitro antimalarial activity.[1][2]

References[edit]

  1. ^ Murakami, Nobutoshi; Umezome, Takashi; Mahmud, Taifo; Sugimoto, Masanori; Kobayashi, Motomasa; Wataya, Yusuke; Kim, Hye-Sook (March 1998). "Anti-malarial activities of acylated bruceolide derivatives". Bioorganic & Medicinal Chemistry Letters. 8 (5): 459–462. doi:10.1016/S0960-894X(98)00045-6. PMID 9871598.
  2. ^ Organization, World Health (1999). WHO monographs on selected medicinal plants. Geneva: World Health Organization. p. 63. ISBN 9241545178.