(E)-Methylisoeugenol and Elemicin:  Antibacterial Components of Daucus carota L. Essential Oil against Campylobacter jejuni

Abstract

The essential oil of wild Daucus carota L. obtained from aerial parts at the end of the flowering stage (DCEO) was reported as antimicrobial against the human enteropathogen Campylobacter jejuni. The aim of the present study was to extend this analysis to other Campylobacter species and to identify the active compounds of the essential oil, subjected to GC, GC-MS, and (13)C NMR analysis. A minimum inhibitory concentration assay was used to quantify the antimicrobial activity of DCEO and the major components, isolated on column chromatography. Growth of all the C. jejuni, Campylobacter coli, and Campylobacter lari strains tested, including one multidrug resistant C. jejuni, was inhibited to the same extent by DCEO. Molecules that were responsible for the antibacterial activity were identified as (E)-methylisoeugenol and elemicin. Moreover, the use of structural analogues of these compounds allowed us to identify important features that may account for the activity.

Antibacterial activity in spices and local medicinal plants against clinical isolates of Karachi, Pakistan

“…For this study, plants having MIC below or equal to 250 µg/ml was considered significant; however, plants having MIC in the range of 500-2000 µg/ml were recorded (their values are not included in Table 2). In recent years, many papers have been published on the plants mentioned in this study, but careful literature search revealed that, mostly, they have described antibacterial activity of volatile oils of the plants (Dorman & Deans, 2000;Rossi et al, 2007;Shayegh et al, 2008;Pinto et al, 2009). Alcoholic extracts of these medicinal plants are reported to have MIC ≥500 µg/ml for antibiotic-sensitive and -resistant strains of clinical isolates, American Type Culture Collection (ATCC) and reference cultures Doughari et al, 2007;Parekh and Chanda, 2007;Jabeen et al, 2008;Khan et al, 2009).…”

Essential oil of Daucus carota subsp. halophilus: Composition, antifungal activity and cytotoxicity

“…halophilus oils showed effective antifungal activity against dermatophyte strains, being the oil rich in elemicine (sample 2 ripe umbels from Cabo de S. Vicente) the most active, with MIC and MLC values ranging from 0.16 to 0.64 l/ml. Accordingly, in a previous publication, elemicin revealed a marked antimicrobial activity against Campylobacter jejuni (Rossi et al, 2007a). However, some essential oil doses that have the ability to completely inhibit fungal growth showed also relatively high cytotoxicity to different types of cells cultured in vitro, in a dose-dependent manner (Prashar et al, 2004;Dijoux et al, 2006;Fabian et al, 2006;Horváthová et al, 2006).…”

“…Daucus carota L. (Apiaceae) is an aromatic plant used since olden times in traditional medicine, due to recognized therapeutic properties, namely the antibacterial and antifungal activity of their essential oils (carrot oil). Although this plant has been subject to several investigations (Saad et al, 1995;Mazzoni et al, 1999;Mockute and Nivinskiene, 2004;Staniszewska et al, 2005;Kula et al, 2006;Wu et al, 2006;Rossi et al, 2007a) some scientific reports do not refer to the subspecies, a crucial aspect of this polymorphic species presenting 11 interrelated subspecies (Castroviejo, 2003). In addition, some reports do not make reference to the developmental stage at which the plants were harvested and how this influences essential oil production and quality.…”

Two New Guaiane-Type Sesquiterpene Glycosides from the Fruits of Daucus carota L.

“…1) Pharmacological studies on the plant of D. carota have demonstrated antibacterial, 2) antifungal, 3) anthelmintic, hepatoprotective 4) and cytotoxic 5) activities. The previous research on chemical constituents of D. carota has carried out the presence of sesquiterpenes, [6][7][8] chromones, 9) flavonoids, 10,11) coumarins 6,12) and anthocyanins.…”

“…The previous research on chemical constituents of D. carota has carried out the presence of sesquiterpenes, [6][7][8] chromones, 9) flavonoids, 10,11) coumarins 6,12) and anthocyanins. 13,14) As a part of our ongoing investigation on bioactive constituents, [15][16][17][18] we initiated a phytochemical investigation on the fruits of D. carota L., which resulted in the isolation of two new guaiane-type sesquiterpene glycosides, 11-O-acetyl-torilolone 8-O-b-D-glucopyranoside (1) and 1b-hydroxytorilolone 11-O-b-D-glucopyranoside (2). In this paper, we report the isolation and structure elucidation of them.…”