Cordidepsine is A Potential New Anti-HIV Depsidone from <i>Cordia millenii</i>, Baker

• Main Authors: Rostanie Dongmo Zeukang, Xavier Siwe-Noundou, Maurice Tagatsing Fotsing, Turibio Tabopda Kuiate, Joseph Tanyi Mbafor, Rui W. M. Krause, Muhammad Iqbal Choudhary, Alex de Théodore Atchadé
• Format: Article
• Language: English
• Published: MDPI AG 2019-09-01
• Series: Molecules
• Subjects: <i>Cordia millenii</i>; isolation; depsidone; cordidepsine; monoglycerol; allotrope sulfur; anti-HIV activity
• Online Access: https://www.mdpi.com/1420-3049/24/17/3202

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>&#946;</i>-amyrone (<b>8</b>), lupeol (<b>9</b>), <i>&#946;</i>-amyrin (<b>10</b>), allantoin (<b>11</b>), 2&#8242;-(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&#8722;MS), high resolution electrospray ionization mass spectrometry (HR-ESI&#8722;MS), fast atom bombardment mass spectrometry (FAB&#8722;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 IC₅₀ = 4.65 &#956;M; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.