Bioactive chemical constituents from ellipeiopsis cherrevensis and stelechocarpus cauliflorus

Abstract

Chemical investigation of the aerial parts of Ellipeiopsis cherrevensis R. E. Fr. (family Annonaceae) led to the isolation of three polyoxygenated cyclohexenes namely ferrudiol and zeylenol and a new derivative, ellipeiopsol D, along with two flavonoid glycosides, tiliroside and kaempferol-3-Ο-rutinoside, as well as a new natural chalcone, 2', 4' –dihydroxy-3'–(2-hydroxybenzyl)-6'–methoxychalcone and one alkaloid, lanuginosine. From the leaves and stems of another annonaceous plant, Stelechocarpus cauliflorus R. E. Fr., four lignans namely galgravin, licarin A, acuminatin, and a 2:1 mixture of veraguensin and galgravin, four aporphine alkaloids which are aristolactam AII, piperolactams A and D noraristolodione, two flavonoids namely engeletin and astilbin, together with one sesquiterpenoid, spathulenol, were isolated. The structure determination of these compounds was accomplished by spectroscopic methods, including UV, IR, MS and NMR, and comparison with previously reported data. 2', 4' –Dihydroxy-3' –(2-hydroxybenzyl)-6' –methoxychalcone, licarin A and piperolactam D exhibited antituberculosis, anti HSV-I and cytotoxic activities, whereas the chalcone also showed antimalarial activity. Acumination displayed antituberculosis and cytotoxic activities, while galgravin exhibited antituberculosisand anti HSV-I activities. Tiliroside, kaempferol-3-Ο-rutinoside, ferrudiol and zeylenol were all able to stimulate lymphocyte proliferation, whereas the latter two cyclohexenes also showed anti HSV-I and antituberculosis activities. In addition, bioactivity-guided fractionation yielded engeletin and astilbin as inhibitors of aldose reductase enzyme and Advance Glycation End Products formation.