Abstract
BackgroundThe present report describes the semi-synthesis of a few O-prenylated phenolic derivatives and their in vitro antitumor activities. These compounds were prepared by modifying two naturally occurring antitumor phenols, 5,7-dihydroxy-3-(1′-hydroxy-1′-phenyl-methyl)-6-methoxy-chroman-4-one (A) and 2′,4′-dihydroxy-3′,6′-dimethoxychalcone (B), previously isolated from Polygonum limbatum Meisn. (Polygonaceae). The structures were elucidated by spectroscopic means and comparison with published data. The cytotoxicity of compounds was determined by using the resazurin assay in the parental drug-sensitive CCRF-CEM cell line and its multidrug-resistant P-glycoprotein-over-expressing subline, CEM/ADR5000.ResultsWe describe in the present paper four new semi-synthetic derivatives of A and B: 5-hydroxy-6-methoxy-7-O-(3′-methylbut-2′-enyl)chroman-4-one (1), trivially named metapchromone, 5-acetoxy-6-methoxy-7-O-[3′-methylbut-2′enyl]chroman-4-one (2), trivially named sargisin, 2′-hydroxy-3′,6′-dimethoxy-4′-O-(3″-methylbut-2″-enyl)chalcone (3) trivially named limbachalcone A, and 2′-acetoxy-3′,6′-dimethoxy-4′-O-(3″-methylbut-2″-enyl)chalcone (4) trivially named tsedengchalcone. Their preliminary cytotoxic activities have been determined. We also report herein the isolation of 1-methylhydantoin (C) and betulinic acid (D) from Polygonum limbatum for the first time.ConclusionsThe study clearly suggests that semi-synthesis involving O-prenylation and acetylation of chalcones or other chromanones should be avoided in a search for anticancer drugs. This conclusion should be helpful when selecting substituents for the synthesis of potential anticancer drugs.
Highlights
The present report describes the semi-synthesis of a few O-prenylated phenolic derivatives and their in vitro antitumor activities
The structure of compound C was established as 1-methyldiazolidine-2,4-dione (Fig. 2). It is a natural product from the Polygonum genus and has been fully characterized here for the first time
We previously reported the cytotoxicity of compound B [3, 4], and the data were reported for a better understanding of the structure-activity relationship (SAR)
Summary
The present report describes the semi-synthesis of a few O-prenylated phenolic derivatives and their in vitro antitumor activities These compounds were prepared by modifying two naturally occurring antitumor phenols, 5,7-dihydroxy-3-(1′-hydroxy-1′-phenyl-methyl)-6-methoxy-chroman-4-one (A) and 2′,4′-dihydroxy3′,6′-dimethoxychalcone (B), previously isolated from Polygonum limbatum Meisn. In the present paper we describe four new semi-synthetic derivatives of compounds A and B: 5-hydroxy-6-methoxy-7-O-(3′-methylbut-2′enyl)chroman-4-one (1) trivially named metapchromone, 5-acetoxy-6-methoxy-7- O-[3′-methylbut- 2′enyl] chroman4-one (2) trivially named sargisin, 2′-hydroxy-3′,6′dimethoxy-4′-O-(3′′-methylbut-2′′-enyl)chalcone (3) trivially named limbachalcone A, and 2′-acetoxy-3′, 6′-dimethoxy-4′-O-(3′′-methylbut-2′′-enyl)chalcone (4), trivially named tsedengchalcone. Their preliminary antitumor activities have been determined. We report the isolation of 1-methylhydantoin (C) as a natural product from the Polygonum genus for the first time
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