Isoformononetin → (+)-Pisatin

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]([C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:12][O:13][C:5]=2[CH:4]=1)=[O:10].[CH3:21][O:22]C1C=CC(C2C(=O)C3C=CC(O)=CC=3OC=2)=C(O)C=1.C[O:43]C1C=CC(C2C(=O)C3C=CC(O)=CC=3OC=2)=CC=1O.C1OC2C=C(C3C(=O)C4C=CC(O)=CC=4OC=3)C=CC=2O1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C@H:9]3[O:10][C:15]4[C:14](=[CH:19][C:18]5[O:22][CH2:21][O:20][C:17]=5[CH:16]=4)[C@@:11]3([OH:43])[CH2:12][O:13][C:5]=2[CH:4]=1

Komponenten

Edukt 4

HCID 3764Isoformononetin

HCID 5280448Calycosin

HCID 5280551Xenognosin B

HCID 5281805Pseudobaptigenin

Produkt 1

HCID 101689(+)-Pisatin

Versuchsvorschrift

Isoformononetin, 2′-hydroxyformononetin, 3′-hydroxyformononetin (calycosin) and pseudobaptigenin were purchased from Apin (Abingdon, UK). Maackiairi and pisatin were kindly provided by Dr. H. D. VanEtten, (University of Arizona, Tucson). Maackiain glucoside and maackiain glucose malonate standards were gifts from Dr. S. Tebayashi (Kochi University, Japan). Medicarpin was from a lab collection. Other isoflavonoids were from Indofine Chemical Company (Somerville, N.J.). CO was obtained from Aldrich and all other chemicals were from Sigma (St. Louis, Mo.).