Anthraquinones from Vismia mexicana.

Abstract

Vismia mexicana (Clusiaceae) is a small tropical tree found from Mexico to Honduras. The CH2Cl2/MeOH extract from the leaves has been reported to have inhibitory properties against reverse transcriptase of human immunodeficiency virus type 1 (HIV-1 RT). In order to characterize some of its chemical constituents, the EtOAc-soluble fraction of this extract was subjected to column chromatography. A new natural product was isolated and designated vismiaquinone D [1-hydroxy-6-methoxy-7,8-(3',3'-dimethyl-pyrano) anthraquinone]. In addition, vismiaquinone was obtained. The structures of vismiaquinone and vismiaquinone D were determined by 1H and 13C NMR spectroscopy, unambiguous assignments were achieved with DEPT, HSQC, and HMBC experiments, and corroborated by X-ray diffraction studies. The isolated anthraquinones were tested against HIV-1 RT. However, none showed relevant activity, suggesting that other compounds in this extract may be responsible for its HIV-1 RT inhibitory properties.