Combination of the essential oil constituents citral, eugenol and thymol enhance their inhibitory effect on Crithidia fasciculata and Trypanosoma cruzi growth

Azeredo, Camila Maria Oliveira de; Soares, Maurílio J.

doi:10.1590/s0102-695x2013000500007

Cited by 27 publications

(26 citation statements)

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“…Previous work has indicated that interactions between eugenol and thymol are dependent on the focal taxon. Eugenol and thymol synergistically inhibited E. coli (Pei et al, 2009) and porcine gut microbiota (Michiels, Missotten, Fremaut, De Smet, & Dierick, 2007), and a eugenol-thymol-citral combination had synergistic toxicity to Trypanosoma cruzi (Azeredo & Soares, 2013). However, eugenol and thymol had antagonistic effects against Crithidia fasciculata (Azeredo & Soares, 2013).…”

Section: Discussionmentioning

confidence: 99%

“…Eugenol and thymol synergistically inhibited E. coli (Pei et al, 2009) and porcine gut microbiota (Michiels, Missotten, Fremaut, De Smet, & Dierick, 2007), and a eugenol-thymol-citral combination had synergistic toxicity to Trypanosoma cruzi (Azeredo & Soares, 2013). However, eugenol and thymol had antagonistic effects against Crithidia fasciculata (Azeredo & Soares, 2013). C. bombi is known to be genetically diverse (Salathé & Schmid-Hempel, 2011), with genotype-specific infection ability (Barribeau, Sadd, du Plessis, & Schmid-Hempel, 2014) and growth rate (Ulrich & Schmid-Hempel, 2012).…”

Section: Discussionmentioning

confidence: 99%

“…Thymol is produced from isoprenoid precursors via the methylerythritol phosphate (MEP) pathway from substrates involved in primary metabolism (Pichersky et al, 2006), meaning that precursors of thymol and related compounds are found in all plant species. As a terpenoid, thymol is a member of the most diverse class of plant volatiles (Pichersky et al, 2006 (Pei, Zhou, Ji, & Xu, 2009), but antagonistic effects against Crithidia fasciculata (Azeredo & Soares, 2013). However, compounds with similar or overlapping targets typically have additive effects (Jia et al, 2009).…”

Section: Study Systemmentioning

confidence: 99%

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Synergistic effects of floral phytochemicals against a bumble bee parasite

Palmer‐Young¹,

Sadd

Irwin

et al. 2017

Ecology and Evolution

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Floral landscapes comprise diverse phytochemical combinations. Individual phytochemicals in floral nectar and pollen can reduce infection in bees and directly inhibit trypanosome parasites. However, gut parasites of generalist pollinators, which consume nectar and pollen from many plant species, are exposed to phytochemical combinations. Interactions between phytochemicals could augment or decrease effects of single compounds on parasites. Using a matrix of 36 phytochemical treatment combinations, we assessed the combined effects of two floral phytochemicals, eugenol and thymol, against four strains of the bumblebee gut trypanosome Crithidia bombi. Eugenol and thymol had synergistic effects against C. bombi growth across seven independent experiments, showing that the phytochemical combination can disproportionately inhibit parasites. The strength of synergistic effects varied across strains and experiments. Thus, the antiparasitic effects of individual compounds will depend on both the presence of other phytochemicals and parasite strain identity. The presence of synergistic phytochemical combinations could augment the antiparasitic activity of individual compounds for pollinators in diverse floral landscapes.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Study Systemmentioning

confidence: 99%

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Synergistic effects of floral phytochemicals against a bumble bee parasite

Palmer‐Young¹,

Sadd

Irwin

et al. 2017

Ecology and Evolution

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“…For example, gallic acid was lethal to Leishmania donovani 26, and thymol and eugenol inhibited growth of Trypanosoma cruzi and Crithidia fasciculata 27. It is therefore likely that some floral phytochemicals may inhibit trypanosome parasites of bumble bees.…”

mentioning

confidence: 99%

“…Cell culture-based methods have been used to quantify the effects of phytochemicals on insect-vectored trypanosome species such as Leishmania donovani 24, Trypanosoma cruzi 2743, and Trypanosoma brucei 244445 that cause disease in humans and are close phylogenetic relatives of C. bombi 46. Here, we extend a previously described C. bombi cell culturing method47 to assess variation in the direct effects of nine floral phytochemicals—two alkaloids, one cyanogenic glycoside, a hydroxycinnamic acid, a hydroxycinnamic acid ester, a gallic acid, a phenylpropene, and two terpenoids—on four different C. bombi strains.…”

mentioning

confidence: 99%

Bumble bee parasite strains vary in resistance to phytochemicals

Palmer‐Young¹,

Sadd

Stevenson

et al. 2016

Sci Rep

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Nectar and pollen contain diverse phytochemicals that can reduce disease in pollinators. However, prior studies showed variable effects of nectar chemicals on infection, which could reflect variable phytochemical resistance among parasite strains. Inter-strain variation in resistance could influence evolutionary interactions between plants, pollinators, and pollinator disease, but testing direct effects of phytochemicals on parasites requires elimination of variation between bees. Using cell cultures of the bumble bee parasite Crithidia bombi, we determined (1) growth-inhibiting effects of nine floral phytochemicals and (2) variation in phytochemical resistance among four parasite strains. C. bombi growth was unaffected by naturally occurring concentrations of the known antitrypanosomal phenolics gallic acid, caffeic acid, and chlorogenic acid. However, C. bombi growth was inhibited by anabasine, eugenol, and thymol. Strains varied >3-fold in phytochemical resistance, suggesting that selection for phytochemical resistance could drive parasite evolution. Inhibitory concentrations of thymol (4.53–22.2 ppm) were similar to concentrations in Thymus vulgaris nectar (mean 5.2 ppm). Exposure of C. bombi to naturally occurring levels of phytochemicals—either within bees or during parasite transmission via flowers—could influence infection in nature. Flowers that produce antiparasitic phytochemicals, including thymol, could potentially reduce infection in Bombus populations, thereby counteracting a possible contributor to pollinator decline.

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Eugenol carbonate activity against Plasmodium falciparum, Leishmania braziliensis, and Trypanosoma cruzi

Clemente

Pineda

Yepes

et al. 2021

Archiv der Pharmazie

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Neglected tropical diseases are a major health problem throughout the world, and there are few effective and safe drugs. In this study, we report the design and synthesis of a novel series of carbonates of eugenol using different aliphatic alcohols and N,N‐carbonyldiimidazole. Spectroscopic techniques, including 1H nuclear magnetic resonance (NMR), 13C NMR, Fourier transform infrared, and high‐resolution mass spectrometry, were used to confirm the structures of the synthesized compounds. In vitro and in silico studies of prodrugs of eugenol were performed to determine their antiplasmodial, trypanocidal, and leishmanicidal activities, and also their cytotoxicity. Compounds were highly active against Leishmania braziliensis and Plasmodium falciparum, whereas the activity shown for Trypanosoma cruzi was moderate. Molecular docking was used to determine a possible mode of action of eugenol against the dihydroorotate dehydrogenase of the three parasites (TcDHODH, LbDHODH, and PfDHODH). Notably, the docking results showed that eugenol not only has binding energy similar to that of the natural substrate (−7.2 and −7.1, respectively) but also has interactions with relevant biological residues of PfDHODH. This result indicates that eugenol could act as a substrate for PfDHODH in the pyrimidine biosynthesis pathway of P. falciparum. In conclusion, the combination of certain aliphatic alcohols and eugenol through a carbonate bond could significantly increase the antiparasitic activity of this class of compounds, which merits further studies.

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Combination of the essential oil constituents citral, eugenol and thymol enhance their inhibitory effect on Crithidia fasciculata and Trypanosoma cruzi growth

Cited by 27 publications

References 30 publications

Synergistic effects of floral phytochemicals against a bumble bee parasite

Synergistic effects of floral phytochemicals against a bumble bee parasite

Bumble bee parasite strains vary in resistance to phytochemicals

Eugenol carbonate activity against Plasmodium falciparum, Leishmania braziliensis, and Trypanosoma cruzi

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