Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents.
Pinostrobin (5-hydroxy-7-methoxyflavanone) obtained in relatively large amounts from fingerroot (Boesenbergia pandurata) was converted to its C-6 and C-8 prenylated derivatives. The Mitsunobu reaction, europium(III)-catalyzed Claisen-Cope rearrangement, and Claisen reaction coupled with cross-metathesis were used as the key steps. Using a sealed-vessel microwave reactor, the Mitsunobu and Claisen/Cope reactions occurred smoothly with short reaction times and in satisfactory yields. The target compounds and five new intermediary substances showed cytotoxic activity toward SK-BR-3, MCF-7, PC-3, and Colo-320DM human tumor cell lines, and all of them had significantly lower IC(50) (microM) values than pinostrobin.
Poerwono
Hadi
H
Faculty of Pharmacy, Airlangga University, Jalan Dharmawangsa Dalam, Surabaya 60286, Indonesia.
Sasaki
Shigeru
S
Hattori
Yoshiyuki
Y
Higashiyama
Kimio
K
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008872:Microwaves; D009369:Neoplasms / Q000188:drug therapy*; D054876:Prenylation; D030521:Zingiberaceae / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D044950:Flavanones; C411294:pinostrobin