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The Essential Oil of Spilanthes acmella Murr

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Abstract

Eighteen compounds have been characterized by GC/MS and Kovats indices in the essential oil of Spilanthes acmella. The major constituents identified were β-caryophyllene (30.2%), γ-cadinene (13.3%) and thymol (18.3%).
... Extracts of A. oleracea had been found to exert certain activities such as antimicrobial, antioxidant, diuretic, larvicidal, analgesic and mosquitocidal activities (Dubey et al., 2014). It was found to contain many important bioactive compounds such as spilanthol, αand β-amyrinester, stigmasterol, miricilic alcohol glycosides, sitosterol, saponins and triterpenes which are responsible for antioxidant activities and other therapeutic uses (Lemos et al., 1991). Among the chemical components, spilanthol is considered to be the major active compound which can impart various important biological activities. ...
... Panc-1 cells treated with 100 µg/ml of methanol extract of Eclipta prostrate showed cell survival value of 0.50 (George et al., . Similarly, methanol extract of Bidens pilosa also showed significant cytotoxic effect against HeLa and KB cells (Lemos et al., 1991). From our experiment (Figure 3), different concentrations of the methanol extract showed a concentration-dependent cytotoxic effects. ...
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Acmella oleracea has been widely used in various traditional medicines for the treatment of different diseases ranging from infection, helminthiasis, peptic ulcer to dental abscess. In this experiment, we analysed the antioxidant property of the methanol extract of A. oleracea by hydroxyl radical-scavenging assay and hydrogen peroxide-scavenging assay. In both the scavenging assays, the plant extract showed free radical scavenging activities in a concentration-dependent manner. The cytotoxic property was also determined by MTT assay, which indicated a potential cytotoxic effect on cancer cell lines such as HeLa (ATCC® CCL-2™) and V79 (ATCC® CCL-93™) cells. Higher cytotoxicity was noticed on V79 with an IC50 of 54.341 µg/ml. The plant extract was only moderately toxic on HeLa. The results indicated that the plant contains important bioactive compounds having pharmacological properties.
... The leaves are used as immunomodulatory, adaptogenic, diuretic, tooth paste, lithotriptic, antiscorbitic, sailagogine, antibacterial, tonic and digestive [2][3][4][5][6][7] . The leaves are reported to contain alkaloids, carbohydrates, pungent amide tannins, steroids, carotenoids, essential oils, sesquiterpenes, amino acids, etc [8][9][10][11][12] . So far no systematic study has been reported to evaluate the immunomodulatory potency of its leaves extract. ...
... Acmella oleracea is already known to be a rich source of important bioactive compounds such as amides, aand b-amyrinester, miricilic alcohol glycosides, sitosterol, saponins, stigmasterol, and triterpenes which are attributed to different biological activities (Lemos et al. 1991;Paulraj et al. 2013). N-Isobutyl-(2E,4Z,8Z,10E)-dodecatetraenamide recorded here is also reported from other species of Acmella (Leng et al. 2011). ...
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Context: A variety of Acmella oleracea (L.) R.K. Jansen (Asteraceae) is used by the Mizo people of India and Myanmar for intestinal helminthiasis. Objective: To perform a chemical analysis of the plant extract using gas chromatography-mass spectrometry (GC-MS) and test the anthelmintic activity on intestinal parasites. Materials and methods: An extract of the aerial parts was prepared in hexane and analysed using GC-MS. Survival test was performed in vitro on the cestode, Taenia tetragona, and the nematode, Ascaridia perspicillum. Concentrations of 1.25, 2.5, 5, 10 and 20 mg/mL, prepared in phosphate-buffered saline (PBS) with 1% dimethylsulphoxide (DMSO), were tested. Negative control was maintained in PBS with DMSO, and albendazole was used as a reference drug. Each treatment consisted of six worms and was done until death was confirmed. Scanning electron microscopy was used to describe the structural changes. Results: Nineteen compounds were detected. The major compounds were fatty alcohols such as 3,7,11,15-tetramethylhexadec-2-en-1-ol and (9Z)-9-hexadecen-1-ol. Important bioactive compounds including an alkylamide, N-isobutyl-(2E,4Z,8Z,10E)-dodecatetraenamide, and a triterpenoid, lupeol, were also confirmed. The lethal concentration (LC50) of the plant extract was 5128.61 ppm on T. tetragona and 8921.50 ppm on A. perspicillum. Tegumental shrinkage, erosion of microtriches, and distortion of the suckers were observed on the cestode. The nematode showed collapse of the lips and shrunk cuticle. Conclusions: Acmella oleracea contains important bioactive compounds, which are responsible for the broad-spectrum anthelmintic activity. Further study on the pharmacology of the compounds is warranted.
... Chemically, S. acmella is known to contain several important compounds including α-and β-amyrinester, amides, miricilic alcohol glycosides, saponins, sitosterol, stigmasterol and triterpenes (15). These compounds have attributed a variety of pharmacological properties. ...
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Spilanthes acmella Murr., popularised as toothache plant, is a well-known culinary and medicinal plant for different purposes, but its use as an anthelmintic is apparently exclusive to the Mizo people of India and Myanmar. A chloro-form extract of Spilanthes acmella Murr. was analysed in a single quadrupole GC-MS system, from which it was found that the major compound was an alkylamide, N-isobutyl-(2E,4Z,8Z,10E)-dodecatetraenamide. A comparative study was performed on the anthelmintic activity of the plant extract and praziquantel (PZQ) against an intestinal cestode, Raillietina echinobothrida. In terms of efficacy, PZQ was more potent, but the plant extract was also effective at all concentrations tested. PZQ caused severe shrinkage and folds of the tegument, constriction of the suckers, dislocation of spines and erosion of microtriches. The plant extract caused shrinkage and folds on the main body but not on the scolex. Damage on the suckers is more pronounced than in PZQ-treated cestodes. The spines were completely removed. The current findings indicate that S. acmella is a good source of compounds with anthelmintic activity.
... range of pharmacological properties. [14] Hexadecanoic acid or palmitic acid detected in A. oleracea in the present study is already known to have anti-inflammatory activity. [15] In addition to this compound, N-isobutyl-(2E,4Z,8Z,10E)-dodecatetraenamide and N-isobutyl-2E, 6Z, 8E-decatrienamide recorded here are also reported from other species Acmella. ...
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Background: Among its many uses, Acmella oleracea (L.) R. K. Jansen as an anthelmintic agent for general intestinal helminthiasis is remarkable because of its indigenous usage in the Mizo traditional medicine. However, the rationale has not been established. Objectives: The objective of this study is to perform chemical analysis of the plant extract using gas chromatography-mass spectrometry (GC-MS) and to test the anthelmintic activity on intestinal helminths. Materials and Methods: Methanol extract of the whole plant was prepared and volatile compounds were analyzed using GC-MS. Anthelmintic activity was studied by survival test on the cestode Raillietina echinobothrida and the nematode Ascaridia galli. Anthelmintic effects were examined using scanning electron microscopy. Results: Thirteen compounds were detected, with methyl n-hexadecanoate (palmitic acid) as the major constituents. N-Alkylamides such as N-isobutyl-(2E,4Z,8Z,10E)-dodecatetraenamide and N-(2-phenylethyl) non-2(E)-en-6, 8-diynamide were present. The plant extract was significantly effective (P < 0.05) at all concentrations tested on both the parasites and showed dose-dependent activity similar to that of albendazole. On the cestode, tegumental shrinkage, erosion of microtriches, and destruction of suckers with clumping of the spines were observed. The nematode was also extensively deformed with its lips collapsed, warty surface on the head, and contracted cuticle on the main body. Conclusion: A. oleracea contains bioactive compounds that have broad-spectrum activity on cestode and nematode parasites.
... It was found to contain many important bioactive compounds such as spilanthol, amyrinester, stigmasterol, miricilic alcohol glycosides, sitosterol, saponins, and triterpenes which are responsible for therapeutic uses. [14,[77][78][79][80] As aresult of phytochemical studies, alkyl amides such as 3-acetylaleuritolic acid, β-sitostenone, scopoletin, vanillic acid, trans-ferulic acid, and transisoferulic acid have been found [9,53] (Table 2). Spilanthol, undeca-2E,7Z,9E-trienoic acid isobutylamide,2E)-N-(2methylbutyl)-2-undecene-8,10-diynamide, deca-6,9-dihydroxy-(2E,7E)-dienoic acid isobutylamide, deca-8,9-dihydroxy-(2E,6Z)dienoic acid isobutylamide, nona-2,3-dihydroxy-6,8-diynoic acid 2-phenylethylamide Leaf, flower pod, whole plant [3,24,42,43,47,53,63,79,81,82] Phytosterols β-sitostenone, stigmasterol, αand β-amyrins - [83] Essential oils ...
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Acmella oleracea (L.) R.K.Jansen belongs to the family Asteraceae is generally called “toothache plant”. Though Acmella genus has complex patterns, the cylindrical discoid capitula which owe agolden yellow color with red tip make it unique. It is an annual herb, occurring around the world and, is cultivated for horticultural, pharmacological (anti-inflammatory, antimicrobial, anesthetic, antioxidant, antiseptic, antiobesity and anticancer), insecticidal, personal care and culinary purposes. Spilanthol is the major alkamide available in Acmella plant, responsible for its unique sensorial effects. There have been remarkable promote in A.oleracea herb in multidisciplinary studies, and anumber of commercial products have been invented over the years. Its application in the food industry has been scarcely explored and make opportunities for further research. This review provides an updated overview of the growing conditions of the plant, identification methods, edibility as food, functional properties, phytochemicals, and other applications which opens future applications in food production.
... Related plants belonging to the family Asteraceae have been reported to have cytotoxic properties on different cell lines. 17,18 From our data (Figure 1), treatment of DLA with different concentrations of the plant extract showed no evident inhibition of the cell growth. However, for HeLa and V79 cells, there is an inverse relationship between treatment concentration and percent inhibition, suggesting possible proliferative potential of the extract on these two cell lines. ...
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Acmella oleracea (family Asteraceae) is known for its diverse applications such as food supplement, vegetable, antioxidant, antineoplastic, antimicrobial, ornamental plant and pig fodder. We prepared an aqueous extract from which the presence of alkaloids, tannins and saponins were detected. These chemical groups have been known for their wide-ranging therapeutic properties. The antibacterial activity was tested on Gram-negative bacteria such as Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli, and a Gram-positive species Bacillus subtilis. The plant extract showed no activity compared to that of the standard antibiotic tetracycline. Cytotoxic activity was also studied on cancer cell lines. We found an inverse relationship between treatment concentration and percent inhibition for HeLa (ATCC ® CCL-2 ™) and V79 (ATCC ® CCL-93 ™), however, the plant extract showed negligible effect on Dalton's lymphoma ascites even at the highest concentration tested. The lower degree of inhibitions observed at higher concentrations for HeLa and V79 suggests that the plant extract might confer proliferative effect rather than antimitogenic effects on the cancer cells. The results indicate that A. oleracea has unique medicinal properties, which in turn provide the rationale for further investigations.
... Padhan et al. (2017) reported limonene (41%), ocimene (20.4%), myrcene (12%) as the most abundant essential oil constituents in another Indian accession of A. oleracea. Lemos et al. (1991) analysed the essential oil from a Brazilian accession and found (E)-caryophyllene We assume that such variability may be linked to geographical factors and genetics of the plant accessions as well as to the part used and extraction conditions employed (Pavela and Benelli, 2016). Table 3 shows the toxicity of A. oleracea essential oil on three insect pests of littoralis larvae with other authors, it can be noted that its efficacy is comparable to other essential oils considered as very promising for the development of botanical insecticides. ...
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The results of evaluating the effects of essential oils on the behavior and reproduction potential of the western flower thrips Frankliniella occidentalis Perg. are presented. Essential oils of Acorus calamus, Juniperus virginiana, and Melissa officinalis possessed a repellent effect on the larvae. A sample from Lutsea cubeba was characterized by an attractive property. Oil solutions of J. virginiana, Mentha spicata, Nepeta cataria, and Litsea cubeba repelled the thrips females off the leaves of the host plant. Reduced concentrations of oils from J. virginiana, M. officinalis, and M. spicata did not affect the distribution of thrips females between the experimental and control leaves, but the number of offspring was significantly lower on the treated leaves.
... Padhan et al. (2017) reported limonene (41%), ocimene (20.4%), myrcene (12%) as the most abundant essential oil constituents in another Indian accession of A. oleracea. Lemos et al. (1991) analysed the essential oil from a Brazilian accession and found (E)-caryophyllene We assume that such variability may be linked to geographical factors and genetics of the plant accessions as well as to the part used and extraction conditions employed (Pavela and Benelli, 2016). Table 3 shows the toxicity of A. oleracea essential oil on three insect pests of economic importance, including vectors of high medical relevance, and agricultural pests as well. ...
Article
Ethnopharmacological relevance: Acmella oleracea (L.) R.K. Jansen (Compositae), well-known as jambú, is a medicinal herb of pungent taste, native to Brazil but cultivated in different parts of the world due to its aromatic and pharmacological properties. In folk medicine, the plant has been used against parasites and to combat insects and mites. No data are available on the insecticidal activity of jambú essential oil. Aim of the study: To test the jambú essential oil obtained from A. oleracea cultivated in central Italy against the filariasis vector Culex quinquefasciatus, the Egyptian cotton worm, Spodoptera littoralis, and the housefly, Musca domestica. Materials and methods: The chemical composition of the essential oil was achieved by GC-FID and GC-MS analyses. Acute toxicity experiments were conducted on larvae of the filariasis vector C. quinquefasciatus and S. littoralis and adults of M. domestica to determine the LC50 and LC90 values of the oil, along with the positive control, α-cypermethrin. Results: (E)-caryophyllene (20.8%), β-pinene (17.3%), myrcene (17.1%) and caryophyllene oxide (10.0%) were the major volatile constituents. Interestingly, the oil contained little amounts (3.9%) of the insecticidal spilanthol. Jambú essential oil exerted relevant effects on C. quinquefasciatus (LC50 = 42.2mgL-1, LC90 = 73.6mgL-1) and S. littoralis 3rd instar larvae (LC50 = 68.1µg larva-1, LC90 = 132.1µg larva-1). High acute toxicity was also detected testing the jambú oil against adult females of M. domestica, achieving a LD50 value of 44.3µg adult-1 and a LD90 value of 87.5µg adult-1. Conclusions: Taken together our data support the traditional use of jambú as an insecticidal agent and represent the scientific basis for the industrial exploitation of the essential oil in the fabrication of green insecticides.
... It is most abundant during summer with the density of 12.3 but the importance value index (IVI) was found to be highest during winter, i.e. 31.9 [4]. It is known to contain several bioactive compounds including spilanthol, α and β-amyrinester, stigmasterol, miricilic alcohol glycosides, sitosterol, saponins and triterpenes [5]. Among the chemical constituents, spilanthol is known to be the major compound and is assumed to be responsible for most of the biological activities [6]. ...
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Acmella oleracea (L) R.K. Jansen is a perennial and polliniferous herb belonging to family Asteraceae, and is mostly found in tropical and sub-tropical regions. It is widely used as an herbal medicine as a common vegetable. It is known to be highly abundant during summer but the importance value index (IVI) is highest during winter. In the light of these beneficial properties, its nutritive content and antioxidant property were evaluated. Fat, carbohydrate and protein contents were estimated, and the total calorific value was found to be 32.588 kcal/100 g. Nitric oxide scavenging assay showed concentration-dependent increase in its antioxidant activity. The IC50 of extract was calculated as 4.492 was higher than that of the standard butylated hydroxytoluene, i.e. 4.121. The reducing power of the extract also showed concentration dependent activities, but the reducing power of the extract was found to be significantly lower than the standard ascorbic acid. The study supports that A. oleracea has valuable biological properties.
Article
The potential insecticidal activity of Spilanthes acmella Murr. (Compositae) extracts was assessed in this study. The extracts were shown to be toxic against adults of American cockroach, Periplaneta americana L. The active component in S. acmella extract was isolated and identified as N-isobutyl-2,6,8-decatrienamide (spilanthol). The results from topical application of spilanthol show that it has a high acute toxicity and spilanthol was the most potent compound when compared to three conventional insecticides. The potency was found to be 1.3, 2.6 and 3.8 times more toxic than carbaryl, bioresmethrin and lindane, respectively. Electrophysiological studies indicated immediate hyperexcitation followed by complete inhibition of the cockroach cercal nerve activity.
Olean-12-ene-3-O-PD-glactopranosyl (1-4)-0-a-L-rhamnopyranoside: A new triterpenoidal saponin f r o m the roots of Spilanthes a m l l a Mum
  • D K Mukharya
  • A H Ansari
D. K. Mukharya and A. H. Ansari, Olean-12-ene-3-O-PD-glactopranosyl (1-4)-0-a-L-rhamnopyranoside: A new triterpenoidal saponin f r o m the roots of Spilanthes a m l l a Mum. Indian J. Chem. Sect. B, 26B( l), 87 (1987).
Vedantham, a-andPAmyrinesters and sitosterol glucoside f r o m Spilanthes acmella
  • N R Krishnaswamy
  • S Prasanna
  • T R N C Seshadriandt
N. R. Krishnaswamy, S. Prasanna,T. R. SeshadriandT.N.C.Vedantham, a-andPAmyrinesters and sitosterol glucoside f r o m Spilanthes acmella. Phytochem., 14, 1666-1667 (1975).