Quinones as Key Intermediates in Natural Products Synthesis. Syntheses of Bioactive Xanthones from Hypericum perforatum 英文参考文献.docVIP

Molecules 2009, 14, 2857-2861; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Quinones as Key Intermediates in Natural Products Synthesis. Syntheses of Bioactive Xanthones from Hypericum perforatum George A. Kraus * and John Mengwasser Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA; E-mail: jhm2876@ (J.M.) * Author to whom correspondence should be addressed; E-mail: gakraus@ Received: 30 July 2009; in revised form: 23 July 2009 / Accepted: 29 July 2009 / Published: 3 August 2009 Abstract: Two bioactive xanthones from Hypericum perforatum have been synthesized by direct routes. Benzo[c]xanthone 5 can be prepared from intermediate 4. Keywords: photoacylation; green chemistry; xanthones Introduction Because of their extensive use as botanical dietary supplements, there is increasing interest in the chemical constituents of Hypericum and Echinacea [1]. Although some components of Hypericum species such as hypericin and hyperforin are well known, these species contain many additional bioactive components, including flavones, procyanidins and xanthones [2]. Among the many xanthones found in Hypericum species, euxanthone (1) and 1-methoxy-7-hydroxyxanthone (2) are found in Hypericum perforatum [3]. Euxanthone exhibits a range of potentially useful biological activities. Recently, researchers reported that euxanthone promotes neurite outgrowth by selectively activating the MAP kinase pathway [4]. Euxanthone showed inhibitory effects on the growth of Plasmodium falciparum with IC50 values in the milligram/milliliter level [5]. Euxanthone also inhibited HIV-1 reverse transcriptase with IC50 values at the milligram/milliliter level [6]. In the vasodilatation assay, both xanthones 1 and 2 exhibited relaxing activity on the contractions evoked by potassium chloride in rat thoracic aorta rings in a dose-dependent manne