Epoxyquinol A, B

A: NPEdia
B: NPEdia
Producing organism
uncharacterized fungus
Biological activity
antiangiogenic activity
isolation and structural determination
  • Kakeya H, Onose R, Koshino H, Yoshida A, Kobayashi K, Kageyama S, Osada H.: Epoxyquinol A, a highly functionalized pentaketide dimer with antiangiogenic activity isolated from fungal metabolites.
    J Am Chem Soc, 124(14): 3496-3497 (2002) PMID: 11929225
  • Kakeya H, Onose R, Yoshida A, Koshino H, Osada H.: Epoxyquinol B, a fungal metabolite with a potent antiangiogenic activity.
    J Antibiot, 55(9): 829-831 (2002) PMID: 12458775
  • synthesis
  • Shoji M, Imai H, Mukaida M, Sakai K, Kakeya H, Osada H, Hayashi Y.: Total synthesis of epoxyquinols A, B, and C and epoxytwinol A and the reactivity of a 2H-pyran derivative as the diene component in the Diels-Alder reaction.
    J Org Chem, 70(1): 79-91 (2005) PMID: 15624908 [ doi: 10.1021/jo048425h ]
  • Shoji M, Yamaguchi J, Kakeya H, Osada H, Hayashi Y.: Total synthesis of (+)-epoxyquinols A and B.
    Angew Chem Int Ed Engl, 41(17): 3192-3194 (2002) PMID: 12207386 [ doi: 10.1002/1521-3773(20020902)41:17<3192::AID-ANIE3192>3.0.CO;2-E ]
  • Shoji M, Kishida S, Takeda M, Kakeya H, Osada H, Hayashi Y.
    A practical total synthesis of both enantiomers of epoxyquinols A and B.
    Tetrahedron Lett. 43, 9155-9158 (2002) [ doi: 10.1016/S0040-4039(02)02271-2 ]
  • synthesis by other group
  • Mehta G, Islam K.
    Total synthesis of the novel angiogenesis inhibitors epoxyquinols A and B.
    Tetrahedron Lett. 44, 3569-3572 (2003) [ doi: 10.1016/S0040-4039(03)00621-X ]
  • biological activity
  • Kamiyama H, Usui T, Uramoto M, Takagi H, Shoji M, Hayashi Y, Kakeya H, Osada H.: Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation.
    J Antibiot, 61(2): 94-97 (2008) PMID: 18408330 [ doi: 10.1038/ja.2008.117 ]
  • Additional information