Bioassay-Guided Chromatographic Isolation and Identification of Antibacterial Compounds from Artemisia annua L. That Inhibit Clostridium perfringens Growth

Abstract

Clostridium perfringens is the causative agent of necrotic enteritis leading to significant losses in the poultry industry. Dichloromethane and n-hexane extracts of aerial parts of Artemisia annua (Asteraceae) exhibited activity against C. perfringens with minimum inhibitory concentrations (MIC) of 185 and 270 μg/mL, respectively. Bioassay-guided fractionation of the extracts gave several active fractions (MIC between 75 and 600 μg/mL). Investigations of the most active fractions resulted in the isolation and characterization of the polyacetylene ponticaepoxide (MIC between 100 and 200 μg/mL) and (+)-threo-(5E)-trideca-1,5-dien-7,9,11-triyne-3,4-diol (MIC between 400 and 800 μg/mL), the flavonols chrysosplenol D (MIC between 200 and 400 μg/mL) and casticin (slight inhibition at 800 μg/mL), and 2,4-dihydroxy-6-methoxyacetophenone (slight inhibition at 800 μg/mL). Also, the coumarin scopoletin and the sesquiterpene lactone artemisinin were isolated from active fractions but showed no inhibition of C. perfringens growth at 800 and 2000 μg/mL, respectively. Fractions containing essential oil components with camphor constituting >60% did not show inhibition of C. perfringens up to 1600 μg/mL. Extracts and some active fractions showed higher antibacterial effect than individual bioactive compounds, suggesting that synergistic effects may underlie the observed antibacterial effect. The present study adds new valuable information on the antibacterial effect of A. annua against C. perfringens.

The First Report on Chemical Composition and Antimicrobial Activity of Artemisia scoparia Waldst. et Kit. Extracts

“…Scoparone was previously isolated from A. scoparia [16][17][18][19][20][21] but was also found in some other species of this genus. Among others scoparone was found in A. capillaris, [22][23][24] A. annua, 25,26 and A. dracunculus. 27 Other abounded components in DE were nonacosane (5.9%), stigmasterol (4.9%), and tritriacontane (3.9%), while in EE scopoletin (1.2%) and vanillin derivatives (2.6%) were above threshold.…”

Phytochemistry, Pharmacology and Mode of Action of the Anti-Bacterial Artemisia Plants

“…A. annua is the most studied plant in the Artemisia genus. Ivarsen et al reported that dichloromethane and n-hexane extracts of the aerial parts of A. annua were active against C. perfringens with a MIC value of 185 and 270 µg/mL, respectively [ 10 ]. In addition, A. annua extracts have also been reported to inhibit a significant number of pathogens such as E. coli , S. typhi , B. subtilis , S. aureus , and C. perfringens [ 63 , 64 ].…”

“…In addition, A. annua extracts have also been reported to inhibit a significant number of pathogens such as E. coli , S. typhi , B. subtilis , S. aureus , and C. perfringens [ 63 , 64 ]. The high anti-bacterial properties of A. annua are due to its primary compounds from essential oil including monoterpenoids group were 30.7% artemisia ketone (18) , 15.8% camphor (33) , and 18.2% from sesqueiterpenes [ 23 ] and also from sabinene ( 1 ), linalool ( 19 ), camphene ( 8 ), α-pinene ( 9 ), α-terpineol ( 24 ), borneol ( 31 & 32 ), camphor ( 33 ), eugenol ( 75 ), and coumarins [ 10 ]. The terpenoids (monoterpenoids) α-terpineol ( 24 ) is also found in A. feddei [ 13 ] and A. princeps Pamp [ 41 ] with a very low to very high activity against 20 pathogenic bacteria with a MIC value of 30 to 3200 µg/mL [ 13 , 41 ].…”

“…A. afra has been found effective against depression, cardiovascular disease, spasms, oxidation, and mycobacteria [ 9 ]. A. annua has been reported to be used to control fevers for over 2 millennia as well as malaria and bacterial infections [ 10 ]. A. indica had high anti-bacterial and antioxidant activities and, thus, its essential oil has been used in the pharmaceutical and food industries [ 11 ].…”

Mechanism of Chinese Medicinal-Medicated Leaven for Preventing and Treating Gastrointestinal Tract Diseases

“…The essential oil of A. annua has an antipathogenic activity such as gram-positive, gram-negative bacterial strains and yeast strains and can interfere with the expression of cell-associated and soluble virulence factors [6]. There are several active fractions and components exhibiting activity against Clostridium perfringens with different minimum inhibitory concentrations [7]. A. annua L. extracts exhibit antimicrobial activity against the periodontopathic microorganisms Aggregatibacter actinomycetemcomitans, Fusobacterium nucleatum subsp.…”