Cordidepsine is A Potential New Anti-HIV Depsidone from Cordia millenii , Baker

Chemical investigation of Baker resulted in the isolation of a new depsidone, cordidepsine ( ), along with twelve known compounds including cyclooctasulfur ( ), lup-20(29)-en-3-triacontanoate ( ), 1-(26-hydroxyhexacosanoyl)glycerol ( ), glyceryl-1-hexacosanoate ( ) betulinic acid ( ), lupenone ( ), -amyrone ( ), lupeol ( ), -amyrin ( ), allantoin ( ), 2'-(4-hydroxyphenyl)ethylpropanoate ( ) and stigmasterol glycoside ( ). Hemi-synthetic reactions were carried out on two isolated compounds ( and ) to afford two new derivatives, that is, cordicerol A ( ) and cordicerol 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 ( )], monoglycerol derivatives [1-(26-hydroxyhexacosanoyl)glycerol ( ) and glyceryl-1 hexacosanoate ( )] were isolated for the first time from genus while sulfur allotrope [cyclooctasulfur ( )] was isolated for the first time from plant origin. Biological assays cordidepsine ( ) exhibited significant anti-HIV integrase activity with IC = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.