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

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.

Lichen-Derived Diffractaic Acid Inhibited Dengue Virus Replication in a Cell-Based System

“…Depsides and depsidones are lichen-derived secondary metabolites with several biological activities such as anticancer, antibacterial, antioxidant, antiparasitic, and antiviral [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ]. We extracted, purified, and screened the anti-DENV2 activity of Usnea baileyi , Usnea aciculifera , and Parmotrema dilatatum and found three compounds with inhibitory activity against DENV2 over 90%.…”

“…Their core structures are composed of orcinol [ 7 ]. Depsides and depsidones with various biological activities have been reported, including antioxidant [ 8 , 9 ], antimicrobial [ 10 , 11 ], antiparasitic [ 12 ], anticancer [ 13 , 14 ], and antiviral [ 15 , 16 , 17 ]. A previous study showed that atranorin and its derivatives exhibited anti-hepatitis C virus (HCV) activity in the entry and replication stage [ 17 ].…”

Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities

“…Cordia millenii investigation resulted in a new analog, 6 that was assigned by spectral and X-ray analyses. This compound had promising HIV-1 integrase efficacy (IC 50 4.65 µM) in comparison to chicoric acid (IC 50 0.33 µM) ( Dongmo Zeukang et al, 2019 ).…”

Physicochemical and Microbiological Characteristics of Stem Bark Exudate Gum of Cordia millenii Tree in Conventional Release Tablets

“…Major uses of Cordia millenii tree are in the area of timber industry and traditional herbal medicine [ 30 , 32 , 33 ]. In African phytomedicine (where it is an indigenous plant), various parts are used to treat or manage fevers, cough, stomachache, toothache, inflammatory-related disorders, HIV, diarrhea, dysentery, ringworm, and worm infestation [ 30 , 33 – 36 ].…”

“…Phytochemicals isolated from different parts of Cordia millenii plant include glycosides (triterpenoids), resins, lipids, sugars, alkaloids, essential oils, tannins, flavonoids (phenolic compounds), steroids, saponins, terpenoid benzoquinones called cordiachromes A–F, and the latest being cordidepsine [ 29 , 34 , 36 , 37 ]. When the stem is slashed, viscous liquid oozes out freely after 7–10 days and continues for several weeks.…”