Bruceanol G

Bruceanol G is a cytotoxic quassinoid isolated from Brucea antidysenterica with potential antitumor and antileukemic properties.[1][2]

Bruceanol G
Names
IUPAC name
Methyl 15β-{[(2E)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-1β,11β,12α-trihydroxy-2,16-dioxo-13,20-epoxy-13β-picrasan-21-oate
Systematic IUPAC name
Methyl (1R,2S,3S,3aS,3a1R,4R,6aR,7aS,8R,11S,11aS,11bS)-4-{[(2E)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-1,2,11-trihydroxy-8,11a-dimethyl-5,10-dioxotetradecahydro-2H-3,3a1-(epoxymethano)phenanthro[10,1-bc]pyran-3-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C30H40O13/c1-12-8-16(32)23(35)28(6)15(12)10-17-29-11-40-30(26(38)39-7,24(36)19(34)21(28)29)22(29)20(25(37)41-17)42-18(33)9-13(2)27(4,5)43-14(3)31/h9,12,15,17,19-24,34-36H,8,10-11H2,1-7H3/b13-9+/t12-,15+,17-,19-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1
    Key: LNFLSPAGUXRAML-GLQLFLDVSA-N
  • InChI=1S/C30H40O13/c1-12-8-16(32)23(35)28(6)15(12)10-17-29-11-40-30(26(38)39-7,24(36)19(34)21(28)29)22(29)20(25(37)41-17)42-18(33)9-13(2)27(4,5)43-14(3)31/h9,12,15,17,19-24,34-36H,8,10-11H2,1-7H3/b13-9+/t12-,15+,17-,19-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1
    Key: LNFLSPAGUXRAML-GLQLFLDVSA-N
  • C[C@@H]1CC(=O)[C@H]([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)OC(=O)/C=C(\C)/C(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
Properties
C30H40O13
Molar mass 608.637 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Okano, M; Fukamiya, N; Aratani, T; Juichi, M; Lee, KH (1985). "Antitumor agents, 74. Bruceanol-A and -B, two new antileukemic quassinoids from Brucea antidysenterica". Journal of Natural Products. 48 (6): 972–5. doi:10.1021/np50042a017. PMID 3841557.
  2. Imamura, K; Fukamiya, N; Nakamura, M; Okano, M; Tagahara, K; Lee, KH (1995). "Bruceanols G and H cytotoxic quassinoids from Brucea antidysenterica". Journal of Natural Products. 58 (12): 1915–9. doi:10.1021/np50126a019. PMID 8691212.


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