| Summary: | Chemical investigation of <i>Cordia millenii,</i> Baker resulted in the isolation of a new depsidone, cordidepsine (<b>1</b>), along with twelve known compounds including cyclooctasulfur (<b>2</b>), lup-20(29)-en-3-triacontanoate (<b>3</b>), 1-(26-hydroxyhexacosanoyl)glycerol (<b>4</b>), glyceryl-1-hexacosanoate (<b>5</b>) betulinic acid (<b>6</b>), lupenone (<b>7</b>), <i>β</i>-amyrone (<b>8</b>), lupeol (<b>9</b>), <i>β</i>-amyrin (<b>10</b>), allantoin (<b>11</b>), 2′-(4-hydroxyphenyl)ethylpropanoate (<b>12</b>) and stigmasterol glycoside (<b>13</b>). Hemi-synthetic reactions were carried out on two isolated compounds (<b>5</b> and <b>6</b>) to afford two new derivatives, that is, cordicerol A (<b>14</b>) and cordicerol B (<b>15</b>), respectively. The chemical structures of all the compounds were established based on analysis and interpretation of spectroscopic data such as electron ionization mass spectrometry (EI−MS), high resolution electrospray ionization mass spectrometry (HR-ESI−MS), fast atom bombardment mass spectrometry (FAB−MS), one dimension and two dimension nuclear magnetic resonance (1D and 2D-NMR) spectral data as well as X-ray crystallography (XRC). Lupeol ester derivatives [Lup-20(29)-en-3-triacontanoate (<b>3</b>)], monoglycerol derivatives [1-(26-hydroxyhexacosanoyl)glycerol (<b>4</b>) and glyceryl-1 hexacosanoate (<b>5</b>)] were isolated for the first time from <i>Cordia</i> genus while sulfur allotrope [cyclooctasulfur (<b>2</b>)] was isolated for the first time from plant origin. Biological assays cordidepsine (<b>1</b>) exhibited significant anti-HIV integrase activity with IC<sub>50</sub> = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.
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