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Chiliadenus lopadusanus Brullo is an Asteraceae plant species endemic to Lampedusa island, the largest island of the Pelage archipelago, Italy. The organic extract of its whole aerial parts, showing antibiotic activity against Staphylococcus aureus and Acinetobacter baumannii, wasfractionated employing bioguided purification procedures affording th...
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... the corresponding organic extracts, that of Chiliadenus lopadusanus showed a growth inhibiting activity against some human pathogenic bacteria. C. lopadusanus Brullo (Figure 1) is an Asteraceae endemic species growing spontaneously on Lampedusa island, the largest island of the Pelage archipelago, about 100 km from the North Africa coast and 200 km from the Sicily coast, Italy [27]. The essential oils produced by the leaves and flowers of C. lopadusanus were first investigated by Sacco and Maffei [28] using GC and GC-MS spectrometry and camphor, borneol, and 1,8-cineole ( Figure 2) were identified as the major constituents. ...
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... (dd, 17.2 and 10.7, H-2), 5.29 (br t, 7.3, H-6), 5.23 (dd, 17.2 and 1.2, H-1A), 5.17 (br dd, 8.5 and 1.3, H-10), 5.08 (dd, 10.7 and 1.2, H-1B), 4.66 (ddd, 11.8, 8.5 and 2.7, H-9), 2.10 (2H, m, H-4), 2.02 (2H, m, H-8), 1.74 (3H, s, Me-12), 1.71 (3H, s, Me-13), 1.68 (3H, s, Me-14), 1.60 (2H, m, H-5), 1.30 (s, Me-15); 13 C NMR (see Table S1), δ: 144.9 (d, C-2 ...
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... it would be of considerable interest to evaluate the possible use of a combination of the three compounds for the prevention of biofilm-related infections. Figure S1. 1 H NMR spectrum of 9-hydroxynerolidol, 1 (CDCl 3 , 400 MHz); Figure S2. 13 C NMR spectrum of 9-hydroxynerolidol, 1 (CDCl 3 , 100 MHz). Figure S3. ...
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... C NMR spectrum of 9-oxonerolidol, 2 (CDCl 3 , 100 MHz). Figure S10. COSY spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S11. ...
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... C NMR spectrum of 9-oxonerolidol, 2 (CDCl 3 , 100 MHz). Figure S10. COSY spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S11. HSQC spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400/100 MHz); Figure S12. ...
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... spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S11. HSQC spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400/100 MHz); Figure S12. HMBC spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400/100 MHz). Figure S13. ...
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... spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400/100 MHz). Figure S13. NOESY spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S14. ...
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... spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400/100 MHz). Figure S13. NOESY spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S14. ESIMS spectrum of 9-oxonerolidol, 2, recorded in positive modality; Figure S15. 1 H NMR spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S16. ...
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... spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S14. ESIMS spectrum of 9-oxonerolidol, 2, recorded in positive modality; Figure S15. 1 H NMR spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S16. 13 C NMR spectrum of chiliadenol B, 3 (CDCl 3 , 100 MHz); Figure S17. ...
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... spectrum of 9-oxonerolidol, 2 (CDCl 3 , 400 MHz); Figure S14. ESIMS spectrum of 9-oxonerolidol, 2, recorded in positive modality; Figure S15. 1 H NMR spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S16. 13 C NMR spectrum of chiliadenol B, 3 (CDCl 3 , 100 MHz); Figure S17. ...
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... spectrum of 9-oxonerolidol, 2, recorded in positive modality; Figure S15. 1 H NMR spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S16. 13 C NMR spectrum of chiliadenol B, 3 (CDCl 3 , 100 MHz); Figure S17. COSY spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S18. ...
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... C NMR spectrum of chiliadenol B, 3 (CDCl 3 , 100 MHz); Figure S17. COSY spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S18. HSQC spectrum of chiliadenol B, 3 (CDCl 3 , 400/100 MHz); Figure S19. ...
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... spectrum of chiliadenol B, 3 (CDCl 3 , 400 MHz); Figure S18. HSQC spectrum of chiliadenol B, 3 (CDCl 3 , 400/100 MHz); Figure S19. HMBC spectrum of chiliadenol B, 3 (CDCl 3 , 400/100 MHz); Figure S20. ...
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The dried aerial parts of the plant Artemisia glabella Kar. et Kir. contain about 1.1% of the very important sesquiterpene lactone arglabin. This compound can be extracted by supercritical CO2 giving a 20 time concentrated extract containing about 22% arglabin. The CO2 extract can be efficiently treated by hydrostatic countercurrent chromatography...
Citations
... The biofilm formation abilities of COL-R A. baumannii and COL-R E. coli were assessed via CV staining, as previously described and with minor modifications (23). A fresh single colony was cultured overnight. ...
Multidrug-resistant Gram-negative bacterial infections pose a serious threat to public health and safety. Colistin is a line of defense against these infections, but colistin-resistant (COL-R) bacteria have emerged worldwide. This study aimed to explore the synergistic potential of nitazoxanide (NTZ) in combination with colistin for the treatment of COL-R Acinetobacter baumannii and Escherichia coli strains in vitro and in vivo . The checkerboard and time-killing assays indicated that NTZ in combination with colistin exhibited potent antibacterial activity against COL-R A. baumannii and COL-R E. coli . The antibiofilm activity measured by crystal violet staining and scanning electron microscopy combined with a confocal laser scanning microscope revealed that the combination of NTZ and colistin could inhibit biofilm formation and eradicate the formed biofilm. This study also demonstrated that the application of this drug combination to an in vivo infection model significantly increased the survival rate of Galleria mellonella larvae. Hemolysis tests revealed that the combination of NTZ and colistin showed no cytotoxicity. Altogether, the combination of NTZ and colistin showed promising synergistic antibacterial and antibiofilm effects in vitro and in vivo . This combination might be used as an alternative therapy for treating COL-R A. baumannii and COL-R E. coli infections.
IMPORTANCE
Colistin is used as a last resort in many infections caused by multidrug-resistant Gram-negative bacteria; however, colistin-resistant (COL-R) is on the rise. Hence, it is critical to develop new antimicrobial strategies to overcome COL-R. We found that nitazoxanide (NTZ) combined with colistin showed notable synergetic antibacterial activity. These findings suggest that the NTZ/colistin combination may provide an effective alternative route to combat COL-R A. baumannii and COL-R Escherichia coli infections.
... The active metabolites belong to the farnesane-type sesquiterpenoids (9-hydroxynerolidol, 9-oxonerolidol, and chiliadenol B). It was suggested that these metabolites have the potential to be developed into new antibiotics (Masi et al., 2021). Both disciplines tackle infection. ...
The Saint Catherine region of southern Sinai Peninsula’s drylands encompasses a unique combination of geophysical conditions. These features have formed highly diverse habitats, which support extremely complex plant communities. Throughout history, the local Bedouin population has used many of these plants for therapeutic purposes. The objectives of this study were to document the medicinal knowledge for as many as possible plant species, evaluate this ethnobotanic knowledge against a modern biomedical database, and identify links between the two disciplines. On-site gathering of information, through structured interviews with two local key informants, revealed the traditional use of 90 native vegetation species for a range of therapeutic purposes. Surveying the modern biomedical uses of these plant species in the PubMed database revealed medicinal use for 41 of them, as well as other plant species without known traditional therapeutic uses. Of the 41 plant species, in-depth integration of traditional and modern knowledge was implemented for 20 species, for which sufficient information was found in the PubMed. The results highlight the common ground between the two disciplines, and propose bridges between traditional and modern medicines. The study stresses the need for additional research in ethnobotany, which may assist in developing new plant-based medications.
... Some of those compounds are either already marketed (daptomycin 37) or in advanced stages of clinical development (ramoplanin 32) for the treatment of complicated infections caused by multidrugresistant bacterial strains. The development of new antibiotics based on LPDs is of vital importance because MRSA (methicillin resistant Staphylococcus aureus) strains are rapidly increasing, [10][11][12][13][14][15]. ...
Natural products are a vital source for agriculture, medicine, cosmetics and other fields. Lipodepsipeptides (LPDs) are a wide group of natural products distributed among living organisms such as bacteria, fungi, yeasts, virus, insects, plants and marine organisms. They are a group of compounds consisting of a lipid connected to a peptide, which are able to self-assemble into several different structures. They have shown different biological activities such as phytotoxic, antibiotic, antiviral, antiparasitic, antifungal, antibacterial, immunosuppressive, herbicidal, cytotoxic and hemolytic activities. Their biological activities seem to be due to their interactions with the plasma membrane (MP) because they are able to mimic the architecture of the native membranes interacting with their hydrophobic segment. LPDs also have surfactant properties. The review has been focused on the lipodepsipeptides isolated from fungal and bacterial sources, on their biological activity, on the structure–activity relationships of some selected LPD subgroups and on their potential application in agriculture and medicine. The chemical and biological characterization of lipodepsipeptides isolated in the last three decades and findings that resulted from SCI-FINDER research are reported. A critical evaluation of the most recent reviews dealing with the same argument has also been described.
... baumannii) and S. aureus, with MIC values of 150 µg/mL and 75 µg/mL, respectively. Compound 130 exhibited antibacterial activity against A. baumannii and S. aureus, with the same MIC value of 150 µg/mL [57]. ...
Infectious diseases caused by bacteria and fungi are threatening human health all over the world. It is an increasingly serious problem that the efficacies of some antibacterial and antifungal agents have been weakened by the drug resistance of some bacteria and fungi, which makes a great need for new antibiotics. Sesquiterpenoids, with abundant structural skeleton types and a wide range of bioactivities, are considered as good candidates to be antibacterial and antifungal agents. In the past decades, many sesquiterpenoids were isolated from plants and fungi that exhibited good antibacterial and antifungal activities. In this review, the names, source, structures, antibacterial and antifungal degrees, and mechanisms of sesquiterpenoids with antibacterial and antifungal activity from 2012 to 2022 are summarized, and the structure-activity relationship of these sesquiterpenoids against bacteria and fungi is also discussed.
... GC-MS analysis revealed that the most abundant VOCs produced by B186 were 2,6,10-trimethyldodecane, and 2-methylheptadecane. Both compounds have been previously reported for their antibacterial and antibiofilm activity [50,51]. Another study reported heptadecane and other related VOCs as bioactive compounds emitted by an endophytic bacteria, B. atrophaeus XEGI50 with a broad spectrum of antimicrobial activity [52]. ...
Bacteria produces secondary metabolites (SMs) and volatile organic compounds (VOCs) that have a significant role in the control of phytopathogens. In this study, the antagonistic activity and the effect of VOCs produced by endophytic bacteria Bacillus sp. B186, Bacillus sp. H274, Pseudomonas sp. B451, Bacillus sp. Andi542, and Streptomyces sp. Sh800 isolated from sugar beet and sea beet plants on the virulence traits of Enterobacter roggenkampii Kh2, the causal agent of postharvest sugar beet soft rot disease were evaluated. All endophytic bacteria tested showed antagonistic activity against bacterial pathogens in vitro. The results of enzymatic activity, HCN production, antibiosis, and siderophore production were varied amongst strains. The VOCs emitted from endophytic bacteria significantly reduced soft root symptoms and the growth of E. roggenkampii Kh2 at different levels. Our results revealed that VOCs produced by all endophytic bacteria significantly reduced swarming and swimming motility, also chemotaxis behavior of E. roggenkampii Kh2 cells toward sugar beet root extract. The VOCs produced by endophytic bacteria except Bacillus sp. B186 significantly reduced twitching motility of E. roggenkampii Kh2. The influence of VOCs on biofilm formation by bacterial pathogen was varied amongst endophytic bacteria. The gas chromatography-mass spectrometry (GC-MS) analysis revealed that strains B186, B451, Andi542, H274, and Sh800 produced 14, 34, 36, 28, and 16 VOCs, respectively with high quality. Our finding provide new information regarding the potential of VOCs with antibacterial activity and as a biocontrol tool for reducing bacterial soft rot disease at harvest.
... Lampedusa, together with Linosa, form the Pelagie Islands Archipelago, minor Sicilian islands in the Mediterranean sea, which have proven to be a fertile source of microorganisms and plants producing secondary metabolites with noteworthy biological activities. Among these were the phytotoxins produced by Neufusicoccum batangarum, the causal agent of the scabby canker of cactus pear (Opuntia ficus-indica L.) [6], an exopolysaccharide produced as plant defense mechanism [7], and some farnesane-type sesquiterpenoids with antibiotic activity against resistant clinic bacteria that were isolated from the native plant Chiliadenus lopadusanus [8]. ...
... Thus, two strictly coastal lichens, the widespread Roccella phycopsis (right, Figure 1) and the rare Ramalina implexa (left, Figure 1), were collected from rocky and sloping coasts of Lampedusa Island. erpenoids with antibiotic activity against resistant clinic bacteria that were isolated from the native plant Chiliadenus lopadusanus [8]. Thus, two strictly coastal lichens, the widespread Roccella phycopsis (right, Figure 1) and the rare Ramalina implexa (left, Figure 1), were collected from rocky and sloping coasts of Lampedusa Island. ...
The antibiotic and nematocidal activities of extracts from two coastal lichen species collected on Lampedusa Island (Sicily), Ramalina implexa Nyl. and Roccella phycopsis Ach., were tested. Methyl orsellinate, orcinol, (+)-montagnetol, and for the first time 4-chlororcinol were isolated from Roccella phycopsis. (+)-Usnic acid was obtained from Ramalina implexa. The crude organic extract of both lichen species showed strong antibiotic activity against some bacterial species and nematocidal activity. Among all the pure metabolites tested against the infective juveniles (J2) of the root-knot nematode (RKN) Meloydogine incognita, (+)-usnic acid, orcinol, and (+)-montagnetol had significant nematocidal activity, comparable with that of the commercial nematocide Velum® Prime, and thus they showed potential application in agriculture as a biopesticide. On the contrary, methyl orsellinate and 4-chlororcinol had no nematocidal effect. These results suggest that the substituent pattern at ortho-para-position in respect to both hydroxyl groups of resorcine moiety, which is present in all metabolites, seems very important for nematocidal activity. The organic extracts of both lichens were also tested against some Gram-positive and Gram-negative bacteria. Both extracts were active against Gram-positive species. The extract of Ramalina implexa showed, among Gram-negative species, activity against Escherichia coli and Acinetobacter baumannii, while that from Roccella phycopsis was effective towards all test strains, with the exception of Pseudomonas aeruginosa. The antimicrobial activity of (+)-usnic acid, methyl orsellinate, and (+)-montagnetol is already known, so tests were focused on orcinol and 4-chlororcinol. The former showed antibacterial activity against all Gram positive and Gram-negative test strains, with the exception of A. baumannii and K. pneumoniae, while the latter exhibited a potent antibacterial activity against Gram-positive test strains and among Gram-negative strains, was effective against A. baumannii and K. pneumonia. These results suggest, for orcinol and 4-chlororcinol, an interesting antibiotic potential against both Gram-positive and Gram-negative bacterial strains.
... Acinetobacter baumannii 5 Chiliadenus lopadusanus [82]; Cistus creticus (CC) and Cistus salviifolius (CS) [93]; Rumex crispus L. and Rumex sanguineus [94] Acinetobacter spp. ...
... In addition, four plants (Crinum angustum Steud. [81], Limonium avei (De Not.) Brullo and Erben [31], Cytinus hypocistis [62], Chiliadenus lopadusanus [82]) were documented as active against the most pathogenic methicillin-resistant strain (MRSA). ...
... Three studies listed Daucus carota subsp. Maximus [95], Lavandula × intermedia [18] and Cytinus [62] as plants effective against the Acinetobacter genus, and another three studies documented Chiliadenus lopadusanus [82], Cistus creticus (CC), and Cistus salviifolius (CS) [93] as effective against A. baumannii. Among these, the Daucus carota plant is effective at a concentration ranging from 1.25 to 2.50 µL/mL, Lavandula × intermedia essential oil (pure) generated an inhibition zone of 47 mm, and Cytinus ethanolic and water extracts (0.5 mg/disc) showed an inhibition zone of around 10 mm. ...
Drug resistance threatening humans may be linked with antimicrobial and anthelmintic resistance in other species, especially among farm animals and, more in general, in the entire environment. From this perspective, Green Veterinary Pharmacology was proven successful for the control of parasites in small ruminants and for the control of other pests such as varroa in bee farming. As in anthelmintic resistance, antimicrobial resistance (AMR) represents one of the major challenges against the successful treatment of infectious diseases, and antimicrobials use in agriculture contributes to the spread of more AMR bacterial phenotypes, genes, and proteins. With this systematic review, we list Italian plants with documented antimicrobial activity against possible pathogenic microbes. Methods: The literature search included all the manuscripts published since 1990 in PubMed, Web of Science, and Scopus using the keywords (i) “antimicrobial, plants, Italy”; (ii) “antibacterial, plant, Italy”; (iii) “essential oil, antibacterial, Italy”; (iv) “essential oil, antimicrobial, Italy”; (v) “methanol extract, antibacterial, Italy”; (vi) “methanol extract, antimicrobial, Italy”. Results: In total, 105 manuscripts that documented the inhibitory effect of plants growing in Italy against bacteria were included. One hundred thirty-five plants were recorded as effective against Gram+ bacteria, and 88 against Gram−. This will provide a ready-to-use comprehensive tool to be further tested against the indicated list of pathogens and will suggest new alternative strategies against bacterial pathogens to be employed in Green Veterinary Pharmacology applications.
... Bioactivity-guided purification was performed using anti-fungal bioassays against the phytopathogenic fungus S. vesicarium. This is a traditional method used in natural product discovery that allows researchers to isolate the pure bioactive compounds from a complex mixture, such as plants' organic extracts [33][34][35][36]. In particular, following the identification of a crude extract with promising biological activity, the next step is its (often multiple) consecutive bioactivity-guided fractionation until the pure bioactive compounds are isolated [37]. ...
To cope with the rising food demand, modern agriculture practices are based on the indiscriminate use of agrochemicals. Although this strategy leads to a temporary solution, it also severely damages the environment, representing a risk to human health. A sustainable alternative to agrochemicals is the use of plant metabolites and plant-based pesticides, known to have minimal environmental impact compared to synthetic pesticides. Retama raetam is a shrub growing in Algeria’s desert areas, where it is commonly used in traditional medicine because of its antiseptic and antipyretic properties. Furthermore, its allelopathic features can be exploited to effectively control phytopathogens in the agricultural field. In this study, six compounds belonging to isoflavones and flavones subgroups have been isolated from the R. raetam dichloromethane extract and identified using spectroscopic and optical methods as alpinumisoflavone, hydroxyalpinumisoflavone, laburnetin, licoflavone C, retamasin B, and ephedroidin. Their antifungal activity was evaluated against the fungal phytopathogen Stemphylium vesicarium using a growth inhibition bioassay on PDA plates. Interestingly, the flavonoid laburnetin, the most active metabolite, displayed an inhibitory activity comparable to that exerted by the synthetic fungicide pentachloronitrobenzene, in a ten-fold lower concentration. The allelopathic activity of R. raetam metabolites against parasitic weeds was also investigated using two independent parasitic weed bioassays to discover potential activities on either suicidal stimulation or radicle growth inhibition of broomrapes. In this latter bioassay, ephedroidin strongly inhibited the growth of Orobanche cumana radicles and, therefore, can be proposed as a natural herbicide.
... This activity was essentially related to the presence of three farnesane-type sesquiterpenes, namely 9-hydroxynerolidol, 9-oxonerolidol, and chiliadenol B (1-3, Figure 1), respectively. The sesquiterpenes 1-3 were identified by comparing their optical rotation data (specific optical rotation: [] 25 D = +5.2 for 1, +14.4 for 2, and +4.0 for 3) and spectroscopic data (IR, UV, 1D 1 H and 13 C NMR and ESIMS) with the literature [12]. Their purity >98% was ascertained by 1 9-Hydroxynerolidol and 9-oxonerolidol (1 and 2) were isolated for the first time together from Solanum melongena [13]. ...
... Plant material (450 g) was extracted by H 2 O/MeOH (1/1, v/v) and the organic extract was purified by a combination of column and TLC as recently reported [12] to obtain all samples as pure oils, namely for 9-hydroxynerolidol (1, 12.4 mg), 9-oxonerolidol (2, 11.7 mg) and chiliadenol B (3, 20.4 mg). 1 The chemical shifts are in δ values (ppm) from TMS. 2 These two signals could be exchanged. ...
9-Hydroxynerolidol, 9-oxonerolidol, and chiliadenol B are three farnesane-type sesquiterpenoids isolated from Chiliadenus lopadusanus that have shown an interesting activity against human pathogens as Gram+ and Gram− bacteria resistant to antibiotics. However, the absolute configuration (AC) of these interesting sesquiterpenes has not been assigned so far. Vibrational and electronic circular dichroism spectra have been recorded and correlations are pointed out for the three compounds. Density functional theory (DFT) calculations are used in conjunction with Mosher’s method of investigation to assign AC. Statistical analysis is considered to quantitatively define the choice of AC from VCD spectra.
... There has been remarkable interest in the last twenty years in the discovery of natural substances as a potential reservoir of innovative therapeutic solutions for human health, with the prospect of integrating and sometimes replacing conventional drugs. In particular, there is a growing interest in the study of natural substances extracted from plants to counter the galloping phenomenon of antibiotic resistance, i.e., the development and spread of microorganisms resistant to the drugs used in anti-infective therapies [1][2][3][4]. The misuse and abuse of antimicrobials in humans and animals have accelerated the growing phenomenon of antimicrobial resistance worldwide. ...
... Structure of 6-acetoxy-1β-, 6-acetoxy-1α-, and 6-acetoxy-10-β-hydroguaiantrienolide, haagenolide, and 1,10-epoxyhaagenolide(1)(2)(3)(4)(5), and the diastereomeric S-and R-MTPA esters of haagenolide(6 and 7). ...
... Structure of 6-acetoxy-1β-, 6-acetoxy-1α-, and 6-acetoxy-10-β-hydroguaiantrienolide, haagenolide, and 1,10-epoxyhaagenolide(1)(2)(3)(4)(5), and the diastereomeric Sand R-MTPA esters of haagenolide(6 and 7). ...
Cotula cinerea, belonging to the tribe Anthemideae, is a plant widespread in the Southern hemisphere. It is frequently used in folk medicine in North African countries for several of its medical properties, shown by its extracts and essential oils. The dichloromethane extract obtained from its aerial parts demonstrated antibiotic activity against Enterococcus faecalis and was fractionated by bioguided purification procedures affording five main sesquiterpene lactones. They were identified by spectroscopic methods (NMR and ESIMS data) as guaiantrienolides, i.e., 6-acetoxy-1β-,6-acetoxy-1α-, and 6-acetoxy-10-β-hydroxyguaiantrienolide (1–3), and germacrenolides, i.e., haagenolide and 1,10-epoxyhaagenolide (4 and 5). The absolute configuration was assigned by applying the advanced Mosher’s method to haagenolide and by X-ray diffraction analysis to 1,10-epoxyhaagenolide. The specific antibiotic and antibiofilm activities were tested toward the clinical isolates of Enterococcus faecalis. The results showed that compounds 3–5 have antibacterial activity against all the strains of E. faecalis, while compound 2 exhibited activity only toward some strains. Compound 1 did not show this activity but had only antibiofilm properties. Thus, these metabolites have potential as new antibiotics and antibiofilm against drug resistant opportunistic pathogens.
