Synthesis and biosynthesis of isocordoin.
In the search of a convenient synthesis for isocordoin (1), a potential anticancer natural product, 2',4'-dihydroxychalcone was inoculated in cell suspension cultures of Morus nigra, which were expected to contain an active prenyltransferase. After 24 hours the target compound was easily isolated from the metabolite extract. Optimization of the biotransformation resulted in a 85% yield of the prenyl derivative.
Vitali
A
A
Ferrari
F
F
Monache
G D
GD
Bombardelli
E
E
Botta
B
B
D000098:Acetophenones / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000737:chemistry; D001711:Biotransformation; D002396:Catechols / Q000138:chemical synthesis*; D002460:Cell Line; D002599:Chalcone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D047188:Chalcones; D046508:Culture Techniques; D004122:Dimethylallyltranstransferase / Q000378:metabolism; D012118:Resorcinols / Q000737:chemistry; D019685:Rosales / Q000737:chemistry*
D000098:Acetophenones; D000972:Antineoplastic Agents, Phytogenic; D001547:Benzaldehydes; D002396:Catechols; D047188:Chalcones; D012118:Resorcinols; C438026:isocordoin; C059354:2',4'-dihydroxychalcone; D002599:Chalcone; D004122:Dimethylallyltranstransferase; C412963:resacetophenone