Cordidepsine is A Potential New Anti-HIV Depsidone from Cordia millenii, Baker.
Rostanie Dongmo ZeukangXavier Siwe NoundouMaurice Tagatsing FotsingTuribio Tabopda KuiateJoseph Tanyi MbaforRui Werner Maçedo KrauseMuhammad Iqbal ChoudharyAlex de Théodore AtchadéPublished in: Molecules (Basel, Switzerland) (2019)
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.
Keyphrases
- mass spectrometry
- high resolution
- gas chromatography
- magnetic resonance
- liquid chromatography
- antiretroviral therapy
- hiv positive
- hiv testing
- human immunodeficiency virus
- hiv infected
- capillary electrophoresis
- high performance liquid chromatography
- hiv aids
- ms ms
- hepatitis c virus
- electronic health record
- men who have sex with men
- structure activity relationship
- tandem mass spectrometry
- big data
- high speed
- oxidative stress
- south africa
- optical coherence tomography
- magnetic resonance imaging
- molecular docking
- human health
- contrast enhanced
- simultaneous determination
- electron transfer
- deep learning
- essential oil