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Partial 13 C NMR spectrum of methanol – water (4:1) crude extracts of R. communis, A.cepa and S. jamaicensis (solvent, D 2 O) before refreeze-drying (a, c and e), and after refreeze-drying (b, d and f), respectively. X denotes signals from internal standard (TSP). NB: unmarked peaks represent other compounds in the plant extract.
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SUMMARY Methanol-water (4:1, v/v) crude extracts (50 mg mL-1) of 25 Jamaican medicinal plants were screened in vitro for anthelmintic activity using infective third-stage larvae of Strongyloides stercoralis. The most effective extract was further chemically scrutinized to isolate and identify the source of the bioactivity, and the efficacy of this...
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... additional freeze-drying (2 × 24 h), methanol concentration in the extracts was reduced by 1·4, 2·8 and 10·0 fold, respectively (Table 1). Nuclear magnetic resonance spectra indicated reduced levels of methanol in the crude extract samples before and after refreeze-drying (Fig. 1). Methanol concen- trations were calculated based on signal intensities in the spectra. The other crude extracts were similarly refreeze-dried and for the same duration (2 × 24 ...
Citations
... Eryngial is an aliphatic and aromatic aldehyde with antibacterial activity and responsible for the flavor and aroma of culantro and other plants (Abiko et al. 2020;Karakaya et al. 2020). In addition, it has anthelmintic, antibacterial, and anti-inflammatory activity, being characterized as a yellowish oil with a pungent odor (Paul et al. 2011;Forbes et al. 2014). Considering that aldehydes, such as eryngial, are derived from α-or β-oxidation of fatty acids (Bridgemohan et al. 2021), and that carnitine is involved in fatty acids Fig. 2 Growth parameters of 102-day-old Eryngium foetidum L. plants sprayed with water or carnitine, and grown under different water conditions. ...
Unlabelled:
Water stress influences plant growth and metabolism. Carnitine, an amino acid involved in lipid metabolism, has been related to responses of plants to abiotic stresses, also modulating their metabolites. Culantro (Eryngium foetidum L.) is a perennial herb, rich in essential oils, native to Latin America, commonly used due to its culinary and medicinal properties. Here, we investigated the effect of exogenous carnitine on morphophysiology and the essential oil profile of culantro plants under water stress. For this, plants were grown under three water conditions: well-watered, drought stress, and re-watered; and sprayed with exogenous carnitine (100 µM) or water (control). Culantro growth was impaired by drought and enhanced by re-watering. Carnitine, in turn, did not reverse drought effects on growth, and impaired the growth of re-watered plants, also improving photosynthetic pigment content. Water conditions and carnitine application changed the essential oil profile of the plants. Drought and re-watering improved the production of eryngial, which was even increased with exogenous carnitine in re-watered plants. In addition, hydroquinone was only produced with the combination of re-watering and carnitine application. The application of exogenous carnitine can be a strategy to induce the production of essential oil compounds with cosmetic and pharmaceutical importance in culantro.
Supplementary information:
The online version contains supplementary material available at 10.1007/s13205-023-03757-y.
... Some of the few previous studies have provided information about the phytochemicals' availability in E. foetidum extracts (Aly, 2010;Dawilai et al., 2013;Forbes et al., 2014;Garcia et al., 1999). They have pharmacological properties, such as antioxidant, antibacterial, antidiabetic, anti-inflammatory (Anusha et al.;Dalukdeniya and Rathnayaka, 2017;Dawilai et al., 2013;Garcia et al., 1999;Malik et al., 2016;Okon et al., 2013;Thomas et al., 2017), due to the presence of those important phytochemicals. ...
... In vitro, Eryngial (trans-2-dodecenal), a bioactive agent extracted from Eryngium foetidum petrol extract, exhibited acute toxicity in L3 larvae of S. stercoralis (Forbes et al. 2014). This substance's rapid inactivation of the larvae may partly justify its lipophilicity, as this property enables it to cross the cuticle easily. ...
... This substance's rapid inactivation of the larvae may partly justify its lipophilicity, as this property enables it to cross the cuticle easily. According to the 24 and 48 h LD50 values, the immediate effect of eryngial is optimally comparable to ivermectin in vitro, indicating its suitability for drug development research (Forbes et al. 2014). ...
... Some examples of medicinal herbs with anti-Strongyloides properties Plant species LD50 (mM) = 0·461 S. stercoralisForbes et al. (2014) ...
Strongyloidiasis could be a significant global health issue undervalued in several countries, which is caused by Strongyloides spp. Challenges stemming from the use of anthelmintic chemotherapy, such as the development of resistance, the progressive cost of medicines, environmental toxicity of chemicals, and residuals in beast products have increased interest in promoting alternative means of control for the use of plant-based parasite control methods. A study on herbal extracts may offer a less expensive yet equally effective alternative for the prevention and treatment of helminthic multi-resistance. We systematically searched the Web of Sciences, PubMed/MEDLINE, and Scopus databases to explore original publications related to medicinal plants and Strongyloides in English on September 29, 2021. The keywords of medicinal plant, traditional medicine, plant extract, herbal medicine, herbal extract, natural drug, Strongyloides, strongyloidiasis, Strongyloides infection, and helminth were used in our search. Researchers can make use of this review as a quick reference. In this study, we have summarized recent advancements and published investigations on herbal and naturally derived medicines in treating strongyloidiasis undertaken by several researchers worldwide. These medicinal herbs, as well as the active and significant compounds they contain, such as alkaloids, phenolic derivatives, tannins, and terpenes, have been outlined in recent articles. Various studies on herbal remedies to treat strongyloidiasis have been undertaken to date, but further research is still required on moderately effective and low harmful substances.
... Another main compound, 2-dodecenal-E, has a role as an anthelminthic drug, and an antibacterial agent 38 . It has also been reported that the 2-dodecenal-E component has an excellent anticonvulsant property 39 . ...
Ducrosia anethifolia L., an aromatic plant of the Apiaceae family, is traditionally used in Iran to improve the odor of foods and drinks. Different biological activities have been reported for this plant such as antibacterial, cytotoxic, antiproliferative, antianxiety, and sedative. The essential oil profile of D. anethifolia was investigated in different plant situations (phenological stages, stalks and fresh aerial parts in seed stage, and powdered and non-powdered seeds in 2018 and 2019). The essential oil was isolated by hydro-distillation using a Clevenger apparatus and was analyzed by gas chromatography. Decanal was the main compound of essential oil in floral-budding stage (40.26%). However, through plant growth and development, its amount decreased and the amount of 2-dodecenal-E increased (up to 64.51% in fresh seed stages). In the seeds, chrysanthenyl acetate was the major ingredient of the essential oil (49.11%), especially in aged and powdered seeds. The maximum and minimum essential oil content (w/v) was obtained from powdered seeds of 2019 (1.95%) and floral-budding stage (0.34%), respectively. Interestingly, principle component analyses (PCA) based on 15 main combinations of the essential oil scattered the studied samples in ordered arrangement from the floral-budding stage to the aged seeds. Briefly, obvious fluctuations were observed in the essential oil of D. anethifolia under various circumstances; flavorous decanal in floral budding, anticonvulsant 2-dodecenal-E in stems, and sedative chrysanthenyl acetate in powdered seeds. It seems this overlooked plant is proving worthy as a new nutraceutical, in any situations.
... The primary anthelmintic component from Eryngium foetidum was discovered as eryngial (trans-2-dodecenal) after a bioassay-guided isolation utilizing a Strongyloides stercoralis testing model. In a 24-hour larval mortality experiment, it has a lower LD50 (461 M) than ivermectin, a positive control (LD 50 = 2.25 mM) [44]. ...
Since ancient times, medicinal plants have been exploited as an anthelmintic. Herbal medicines originating from plant sources are less costly and also have a minimal side impact on the host organism as compared to synthetic medications, which are more expensive and have more side effects. According to the folk claims, there are many species of plants that have demonstrated and reported promising anthelmintic activity. It could be used to create drug candidates in the search for novel antihelmintic herbal medications. The various methods of extraction have been explored to obtain anthelmintic phytoconstituents from the plants. The aqueous extract followed by methanolic and ethanolic extract has shown more significant anthelmintic potential as proven in different in vivo and in vitro studies. However, the anthelmintic potential depends on the presence of major phytoconstituents present in the plants like tannins, which shows more potential followed by flavonoids. Besides phenolic compounds, saponins and alkaloids are also reported to be responsible for anthelmintic activity. Different new active principles were identified from various medicinal plants and studied through both in vivo and in vitro models where possible mechanism of action have also been identified in some cases.
... is species is also used in ethnomedicine, since it has shown potential application in diseases related to the gastrointestinal tract and acts as an antibacterial, analgesic, anti-inflammatory, anthelmintic, anticonvulsant, and anticancer agent, thus proving to have great ethnopharmacological importance for people [10][11][12]. In this sense, studies have analyzed the applications of E. foetidum and have pointed to its pharmacological potential, notably Bhavana et al. [3], Forbes et al. [13], Sumitha et al. [14], and Leitão et al. [15], confirming the bioactive and antioxidant potential of this plant. ...
Eryngiumfoetidum L. is popularly known as chicória-do-Pará, is native to the Amazon region, and is widely distributed in Northern Brazil. It is considered a versatile species due to its diversified uses in ethnomedicine, gastronomy, and pharmaceutical industry. The objective of this study was to review the literature on the traditional uses, chemical composition, and pharmacological activities of E. foetidum based on information published in national and international scientific articles between the years 2011 and 2021. Literature searches were performed with the combination of the expressions “Eryngium foetidum L.,” “chicória-do-Pará,” “traditional uses,” “ethnobotany,” “volatile compounds,” and “essential oil.” The species is widely used as a flavoring condiment in beans, meat, duck, and fish, and in the preparation of tucupi (cassava sap), showing to have great importance for the Amazonian food culture. In traditional medicine, it has analgesic, antibacterial, antiflu, and antipyretic applications. The chemical profile is characterized by the presence of aromatic and aliphatic aldehydes, mainly (2E)-2-dodecenal in leaves and 2,3,4-trimethylbenzaldehyde in roots, in addition to fixed compounds such as carotenoids, flavonoids, and phenols. These compounds have shown diverse biological activities and potential antibacterial, anthelmintic, and antioxidant applications, confirming their potential for use in folk medicine. Therefore, it is inferred that this aromatic plant has vast potential uses and is an important alternative as a natural resource for the food and pharmaceutical industries in view of its antioxidant capacity and bioactive compounds.
... trans-2-Dodecenal is a natural product isolated from Eryngium foetidum and Coriandrum sativum [68,69]. Though trans-2-alkenals being practically ubiquitous in Heteroptera [70,71], no isolation of trans-2dodecenal has been reported from stink bugs. ...
Odorant-binding proteins (OBPs) play essential roles in the functioning of insect peripheral olfactory systems. To fully understand the olfactory roles of OBPs in Halyomorpha halys, an important invasive pest found worldwide, we studied the expression and functional characterization of five OBP-associated genes from H. halys that are clustered in the genome. The tissue distribution of the OBP gene cluster suggests that these genes were enriched in nymph and adult antennae, indicating their possible involvement in the chemosensory process. The different expression levels of the five OBPs in nymph and adult antennae suggest that this gene cluster is regulated independently. Ligand-binding experiments have shown similar specificities of these five OBPs towards several organic compounds, including the alarm pheromone of H. halys (trans-2-decenal), the aggregation pheromone of Plautia stali (methyl (2E, 4E, 6Z)-decatrienoate), and plant volatile compounds (e.g., cis-3-hexenyl benzoate and β-ionone). In particular, trans-2-dodecenal, an alarm pheromone analog, exhibited high affinity to the five OBP proteins and alarm pheromone activity towards H. halys. Thus, this OBP cluster may mediate the response of stink bugs to the both the alarm pheromone and host-related volatiles and could be an interesting target to design novel olfactory regulators for the management of H. halys infestations.
... Aldehydes have been reported to be efficient however with varied specificity and levels of activity, which is related not solely to the functional group present and further to hydrogen bonding parameters (11). (E)-2-Dodecenal, a major component of the oil, has been found to possess anthelmintic activity against Strongyloides stercoralis (12). ...
This investigation displays antioxidant potential of Cymbocarpum erythraeum essential oils and their biological effects like cytotoxic and anticholinesterase. The antioxidant capacities of the essential oils were estimated by DPPH, TBA, TOS assays. The anticholinesterase activity of essential oils was estimated utilizing Ellman method. The human U-87MG and PC-3 were handled and measurements were estimated by MTT test. The root essential oil showed high cytotoxic activity on PC-3 cells with 48.33% whereas aerial part essential oils indicated high cytotoxic activity on U-87MG cells with 34.62% at 0.03 mg/L. Root oil presented the highest acetylcholinesterase and butyrylcholinesterase inhibition (IC50: 113, 197 µM, respectively). The GC-FID and GC-MS assays showed that major components of aerial part with flowers and root oils were (E)-2-decenal (52.1%); (E)-2-dodecenal (36.1%), and (E)-2-tetradecenal (22.3%), respectively. (E)-2-dodecenal was a major compound of root il and exhibited AChE and BuChE inhibitory (IC50: 100, 136 µM, respectively) and antioxidant effects.
... From a bioassay-guided isolation using a Strongyloides stercoralis testing model, eryngial (trans-2-dodecenal) was identified as the main anthelmintic compound. Its LD 50 (461 µM) in a 24 h larval mortality assay is lower than the positive control ivermectin (LD 50 = 2.25 mM) [69]. ...
Intestinal parasitic nematodes infect approximately two billion people worldwide. In the absence of vaccines for human intestinal nematodes, control of infections currently relies mainly on chemotherapy, but resistance is an increasing problem. Thus, there is an urgent need for the discovery and development of new anthelmintic drugs, especially ones with novel mechanisms of action. Medicinal plants hold great promise as a source of effective treatments, including anthelmintic therapy. They have been used traditionally for centuries and are mostly safe (if not, their toxicity is well-known). However, in most medicinal plants the compounds active against nematodes have not been identified thus far. The free-living nematode C. elegans was demonstrated to be an excellent model system for the discovery of new anthelmintics and for characterizing their mechanism of action or resistance. The compounds discussed in this review are of botanical origin and were published since 2002. Most of them need further studies of their toxicity, mechanisms and structure-activity relationship to assess more fully their potential as drugs.
... ANNONACEAE Annona squamosa L. Ata/Ata do mato α-pineno, sabineno, limoneno (Andrade et al., 2001). APIACEAE Eryngium foetidum L.Chicória trans-2-dodecenal(Forbes et al., 2014), actividad antiinflamatoria(Dawilai et al., 2013). APOCYNACEAE Himatanthus articulatus (Vahl) Woodson ...
The research aimed to study the ethnobotanical evaluation of some medicinal plants of the community of Caruarú, Isla de Mosqueiro-PA, and to search their phytochemical and pharmacological applications. Semi-structured interviews, Shannon-Wiener diversity indices and equity, consensus value techniques, relative Importance, and informant consensus factor were evaluated. Fabaceae was the most representative family. Diversity and equity were 1.61 and 0.95, respectively. Anacardium occidentale, Cinnamomum verum, Eleutherine bulbousa, and Caamembeca spectabilis received the greatest consensus use. The greatest relative importance was for A. occidentale L. and C. spectabilis. The greatest informant consensus factor was for the genitourinary system. The leaf and the tea were the most used. The preparations of the plants and their applications configure essential data for future analysis.
