The anti-mycobacterial activity ofArtemisia annuaL is based on deoxyartemisinin and artemisinic acid

Abstract

The discovery of antimalarial artemisinin from Artemisia annua L. is an example of how Traditional Chinese Medicine (TCM) may be exploited to meet a recognized need. In this study, we systemically investigated A. annua L. for its antimicrobial activity and assessed it as a source of bioactive natural products for anti-mycobacterial activity. We used a silica gel column to perform antimicrobial activity-guided purification of the A. annua leaf, whose identity was confirmed by rbcL DNA barcoding, and used UHPLC-HRMS and NMR to elucidate the structure of purified active compounds. The antimicrobial activity of crude extracts, isolated compounds and the control artemisinin (Apollo Scientific Ltd) was assessed against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium smegmatis strains by serial micro dilution method (31.25-1000 μg/mL). The isolated compounds were tested for synergistic effects against mycobacterium. Bioactive compounds were purified and identified as deoxyartemisinin and artemisinic acid. Artemisinic acid (MIC 250 μg/mL) was more effective in comparison to deoxyartemisinin (MIC 500 μg/mL) and artemisinin (MIC 1000 μg/mL) against M. smegmatis. We used a molecular docking approach to investigate the interactions between selected anti-mycobacterial compounds and proteins involved in vital physiological functions in M. tuberculosis, namely MtPks13, MtPknB, MtPanK, MtKasA, MtInhA and MtDprE1 and found artemisinic acid showed docking scores superior to the control inhibiters for MtKasA, suggesting it to be a potential nick for further in vitro biological evaluation and anti-TB drug design.

Unveiling the Phytochemical Profile and Biological Potential of Five Artemisia Species

“…We report herein for the first time on the anti-mycobacterial activity of Artemisia root extracts and that their potency was found to be similar to that of the aerial part extracts. Our results are in agreement with the study of Bhowmick et al [89] which showed the inhibitory effects of an hexane extract from A. annua aerial parts against Mycobacterium smegmatis (MIC range: 250-1000 mg/L). Further, the bioactivity-linked fractionation of the extract revealed that its inhibitory effects were due to the sesquiterpenes deoxyartemisinin and artemisinic acid [89].…”

“…Our results are in agreement with the study of Bhowmick et al [89] which showed the inhibitory effects of an hexane extract from A. annua aerial parts against Mycobacterium smegmatis (MIC range: 250-1000 mg/L). Further, the bioactivity-linked fractionation of the extract revealed that its inhibitory effects were due to the sesquiterpenes deoxyartemisinin and artemisinic acid [89]. Regarding our Artemisia species, the LC-MS/MS analysis showed that chrysartemin A and B were present only in the most active sample-A.…”

Optimal Fermentation of Artemisia annua Residues and Its Effects on Production Performance of Laying Hens

“…The efficacy of furan includes anti-cancer, antidepressant, anti-anxiolytic, anti-inflammatory, antimicrobial, etc., effects [22], which may reduce the anxiety symptoms of laying hens in a closed environment and increase the production performance due to the higher content of 2furyl-5-methyl furan in the fermented AAR. In addition, deoxyartemisinin, n-hexadecanoic acid, and aromandendrene have antimicrobial effects [23][24][25]. Phytol has antimicrobial, anxiolytic, anticonvulsant, anti-inflammatory, and immunomodulatory effects [26], while calarene also has anxiolytic and anticonvulsant effects.…”

Applicability of Redirecting Artemisinins for New Targets

“…ARTS efficacy against bacterial pathogens has been examined in vitro; for example, their anti‐mycobacterial activity was inferior by two orders of magnitudes to that of Rifampicin. [ 69 ] Other in vitro trials revealed a potential use of artemisinin against Helicobacter pylori , both when combined with gentamycin [ 70 ] or alone. [ 71 ] Lin et al., [ 15 ] reported an in vitro anti‐ Staphylococcus aureus effect of artemisinin complexed in beta‐cyclodextrin: 20 mg mL −1 abolished the bacteria within four days.…”