Abstract
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 IC50 = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.
Highlights
Acquired Immune Deficiency Syndrome (AIDS) is one of the major viral infections ravaging the world; around 76.1 million people have been infected since the first report in 1981 [1]
We report here the isolation and structural identification of fifteen compounds from C. millenii and some hemi-synthetic derivatives
(4) [11], glyceryl-1-hexacosanoate (5) [12], which are monoglycerides and this is the first report of monoglycerol from Cordia genus
Summary
Acquired Immune Deficiency Syndrome (AIDS) is one of the major viral infections ravaging the world; around 76.1 million people have been infected since the first report in 1981 [1]. According to the report of the Cameroon Population Based HIV Impact Assessment (CAMPHIA) in 2018, viral prevalence in Cameroon is 3.4% [2] and about 37 million people around the world are currently living with the infection [1]. The resistance to treatment may be due to the new interference mechanisms with antimicrobial activity and the emergence of some conditions that weaken the patient’s innate immunity [4]. Since antimicrobial drugs remain necessary for the treatment of many diseases, it is imperative to search for new and efficient ones that may reduce bacterial resistance. The current work identified potential antibacterial agents from Cordia millenii
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