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Chemical investigation of Cordia millenii, Baker resulted in the isolation of a new depsidone, cordidepsine ( 1 ), along with twelve known compounds including cyclooctasulfur ( 2 ), lup-20(29)-en-3-triacontanoate ( 3 ), 1-(26-hydroxyhexacosanoyl)glycerol ( 4 ), glyceryl-1-hexacosanoate ( 5 ) betulinic acid ( 6 ), lupenone ( 7 ), β -amyrone ( 8 ), lupeol ( 9 ), β -amyrin ( 10 ), allantoin ( 11 ), 2'-(4-hydroxyphenyl)ethylpropanoate ( 12 ) and stigmasterol glycoside ( 13 ). Hemi-synthetic reactions were carried out on two isolated compounds ( 5 and 6 ) to afford two new derivatives, that is, cordicerol A ( 14 ) and cordicerol B ( 15 ), 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 ( 3 )], monoglycerol derivatives [1-(26-hydroxyhexacosanoyl)glycerol ( 4 ) and glyceryl-1 hexacosanoate ( 5 )] were isolated for the first time from Cordia genus while sulfur allotrope [cyclooctasulfur ( 2 )] was isolated for the first time from plant origin. Biological assays cordidepsine ( 1 ) exhibited significant anti-HIV integrase activity with IC 50 = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.

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