N-alkylamides of Spilanthes (syn: Acmella): Structure, purification, characterization, biological activities and applications – a review

Sharma, Rahul; Arumugam, N.

doi:10.1016/j.fufo.2021.100022

Cited by 16 publications

(15 citation statements)

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“…Previous studies reported that B. acmella extract exhibited antioxidant, antimicrobial, vasorelaxant ( Prachayasittikul et al, 2009 ; Sharma and Arumugam, 2021 ), anti-inflammatory ( Kim et al, 2018 ), and aphrodisiac ( Sharma et al, 2011 ) activities. In terms of bone activities, it was able to raise alkaline phosphatase levels ( Widyowati, 2011 ).…”

Section: Introductionmentioning

confidence: 99%

“…Phenolics, coumarin, triterpenoid, stigmasterol, and stigmasteryl glucoside contributed to the antioxidant activity, whereas vasorelaxant properties were enhanced by pentacyclic and 3-acetylaleuritolic acid ( Wongsawatkul et al, 2008 ; Prachayasittikul et al, 2009 ). Spilanthol and other alkyl amides present in B. acmella extract also contributed significantly to its anti-inflammatory ( Sharma et al, 2011 ; Bakondi et al, 2019 ) and antioxidant ( Abeysiri et al, 2013 ; Sharma and Arumugam, 2021 ) activities. A recent study also reported that components in B. acmella extract such as 1,3-butanediol 3-pyroglutamate, 2-deoxy-d-ribono-1,4-lactone, methyl pyroglutamate, ampelopsisionoside, icariside B1, bezyl-α-1-arabinopyranosyl-(1,6)-β-d-glucopyranoside ( Widyowati et al, 2020a ), methyl threonolactones, and pyroglutamates contributed to its ALP activity and mineralization of osteoblast MC3T3-E1 cells ( Widyowati et al, 2020b ).…”

Section: Introductionmentioning

confidence: 99%

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Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

et al. 2022

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Blainvillea acmella (L.) Philipson [Asteraceae] (B. acmella) is an important medicinal plant native to Brazil, and it is widely known as a toothache plant. A plethora of studies have demonstrated the antioxidant activities of B. acmella and few studies on the stimulatory effects on alkaline phosphatase (ALP) secretion from bone cells; however, there is no study on its antioxidant and anabolic activity on bone cells. The study aimed to evaluate the phytochemical contents of aqueous and ethanol extracts of B. acmella using gas chromatography mass spectrometry (GCMS) and liquid chromatography time of flight mass spectrometry (LCTOFMS) along with the total phenolic (TPC) and flavonoid (TFC) contents using Folin-Ciocalteu and aluminum colorimetric methods. The extracts of B. acmella leaves were used to scavenge synthetic-free radicals such as 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) assays. The bone anabolic effects of B. acmella extracts on MC3T3-E1 cells were measured with 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazoium bromide (MTT) at 1, 3, 5, and 7 days, Sirius-red and ALP at 7 and 14 days, and Alizarin Red S at 14 and 21 days. Comparatively, ethanol extract of B. acmella (BaE) contributed higher antioxidant activities (IC50 of 476.71 µg/ml and 56.01 ± 6.46 mg L-ascorbic acid/g against DPPH and FRAP, respectively). Anabolic activities in bone proliferation, differentiation, and mineralization were also higher in B. acmella of ethanol (BaE) than aqueous (BaA) extracts. Positive correlations were observed between phenolic content (TPC and TFC) to antioxidant (ABTS and FRAP) and anabolic activities. Conversely, negative correlations were present between phenolic content to antioxidant (DPPH) activity. These potential antioxidant and bone anabolic activities in BaE might be due to the phytochemicals confirmed through GCMS and LCTOFMS, revealed that terpenoids of α-cubebene, cryophyllene, cryophyllene oxide, phytol and flavonoids of pinostrobin and apigenin were the compounds contributing to both antioxidant and anabolic effects in BaE. Thus, B. acmella may be a valuable antioxidant and anti-osteoporosis agent. Further study is needed to isolate, characterize and elucidate the underlying mechanisms responsible for the antioxidant and bone anabolic effects.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

et al. 2022

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“…They are fatty acid amides, derived from a condensation reaction between a fatty acid chain and a decarboxylated amino acid. In fact, it is reported that there are several chemically distinct amine fractions that match to different fatty acids conducting to diverse and numerous N -alkylamides in A. oleracea [ 66 ]. However, the most abundant compound of this class is spilanthol, which is an olefinic N -alkylamide endowed with an isobutyl side chain.…”

Section: Secondary Metabolitesmentioning

confidence: 99%

A Review of the Chemistry and Biological Activities of Acmella oleracea (“jambù”, Asteraceae), with a View to the Development of Bioinsecticides and Acaricides

Ferrati

Baldassarri

Cappellacci

et al. 2022

Plants

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Human pathologies, environmental pollution, and resistance phenomena caused by the intensive use of chemical pesticides have shifted the attention of the agrochemical industries towards eco-friendly insecticides and acaricides. Acmella oleracea (L.) R. K. Jansen (jambù) is a plant native to South America, widely distributed and cultivated in many countries due to its numerous pharmacological properties. This review analyzes literature about the plant, its uses, and current knowledge regarding insecticidal and acaricidal activity. Acmella oleracea has proven to be a potential pesticide candidate against several key arthropod pest and vector species. This property is inherent to its essential oil and plant extract, which contain spilanthol, the main representative of N-alkylamides. As a result, there is a scientific basis for the industrial exploitation of jambù in the preparation of green insecticides. However, studies related to its toxicity towards non-target species and those aimed at formulating and developing marketable products are lacking.

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“…Other bioactive substances such as 3-acetylaleuritolic acid (8), trans-ferulic acid (9), stigmasterol (10), vanillic acid (11), sitosterone (12), and trans-isoferulic acid (13) are also present in extracts from A. oleraceaʼs (▶ Fig. 2) [6].…”

Section: Introductionmentioning

confidence: 99%

“…Spilanthol displays a broad spectrum of biological activity, mainly including anti-inflammatory 2 , 6 , 8 , 9 , analgesic 2 , 6 , 8 , 9 , 10 , 11 , antioxidant 6 , 7 , 8 , 9 , antifungal 2 , 6 , 8 , 12 , bacteriostatic 6 , 7 , 8 , 12 , anti-larvicidal, and insecticidal effects 6 , 8 , 10 , 13 , 14 and therefore has been the subject of great interest. Importantly, spilanthol displays muscle relaxing and skin smoothing effect.…”

Section: Introductionmentioning

confidence: 99%

Extraction, Purification, Quantification, and Stability of Bioactive Spilanthol from Acmella oleracea

et al. 2022

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Acmella oleracea is an ethnobotanically significant plant with a relatiwely high content of spilanthol. Due to its broad spectrum of activity, including anti-inflammatory, antioxidant, analgesic, antifungal, and bacteriostatic properties, it is considered a valuable bioactive natural product. In addition, spilanthol as its main bioactive component inhibits facial muscle contractions, making it an attractive ingredient in anti-wrinkle and anti-aging cosmetics. Due to its muscle paralyzing effects, it is called herbal botox. The commercial interest in spilanthol encourages the development of effective methods of isolating it from plant material. The methodology used in this paper allows for the obtaining of extracts from Acmella oleracea with a relatively high content of spilanthol. An effective method of spilanthol extraction from all aerial parts of Acmella oleracea as well as methods of enriching spilanthol concentration in extracts achieved by removing polar and acidic substances from crude extracts was developed. To quantify the concentration of spilanthol, a simple, fast and economically feasible quantification protocol that uses nuclear magnetic resonance (HNMR) was developed. In addition, it has been proven, that oxidation of spilanthol by air gives (2E,7Z)-6,9-endoperoxy-N-(2-methylpropyl)-2,7-decadienamide. The studies on spilanthol solutions stability were carried out and the conditions for the long-time storage of spilanthol solutions have also been developed. Additionally, for confirmation of obtained results a sensitive (LOQ=1 ng/mL), precise (RSD lower than 7%) and accurate (RE lower than 7.5%), new HPLC-MS/MS method was applied.

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N-alkylamides of Spilanthes (syn: Acmella): Structure, purification, characterization, biological activities and applications – a review

Cited by 16 publications

References 147 publications

Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

A Review of the Chemistry and Biological Activities of Acmella oleracea (“jambù”, Asteraceae), with a View to the Development of Bioinsecticides and Acaricides

Extraction, Purification, Quantification, and Stability of Bioactive Spilanthol from Acmella oleracea

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