A new class of biflavonoids: 2'-hydroxygenistein dimers from the roots of white lupin.
Two novel isoflavonoid dimers presumably originating from 2'-hydroxygenistein, 5,7,4'-trihydroxycoumaranochroman-4-one-(3-->5"')-5",7",2"'4"'- tetrahydroxyisoflavone (1, lupinalbisone A) and 5,7,4'-trihydroxycoumaranochroman-4-one-(3-6")-5",7",2"',4"'-te trahydroxyisoflavone (2, lupinalbisone B) were isolated from the roots of Lupinus albus L., and their structures involving relative stereochemistry were elucidated by spectroscopic methods. Using horse radish peroxidase and 2'-hydroxygenistein (3) as the substrate revealed the formation of these dimers together with 5,7,4'-trihydroxycoumaronochromone (4, lupinalbin A). Dimerization of 3 caused a remarkable increase of antifungal activity.
Sakasai
M
M
Department of Applied Bioscience, Faculty of Agriculture, Hokkaido University, Sapporo, Japan.
Fukui
H
H
Yamane
H
H
Kyaw
A N
AN
Tahara
S
S
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002963:Cladosporium / Q000187:drug effects; D019281:Dimerization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D010944:Plants / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D000935:Antifungal Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007529:Isoflavones; C412241:lupinalbisone A; C412242:lupinalbisone B