Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity

Althaus, Julia B.; Malyszek, Claudine; Kaiser, Marcel; Brun, Reto; Schmidt, Thomas

doi:10.3390/molecules22050796

Cited by 21 publications

(18 citation statements)

References 16 publications

(31 reference statements)

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“…More recent efforts to elucidate the structural and biological properties of the chemical entities within complex anti-parasitic natural product extracts have identified molecules with significant potential for treating NTD’s. For example, recently the antiprotozoal activity of the isolated alkamide dodeca-2 E ,4 E -dienoic acid 4-hydroxy-2-phenyl-ethylamide from Anacyclus pyrethrum roots has been reported against L. donovani , T. b. rhodesiense , T. cruzi and the NF54 strain of Plasmodium falciparum with an IC 50 of 4.19 ± 1.64, 2.26 ± 0.18, 1.88 and 3.18 ± 0.20 µM, respectively [ 31 ]. Australia has a high level of biodiversity providing an exceptional resource for natural product drug discovery.…”

Section: Introductionmentioning

confidence: 99%

Screening a Natural Product-Based Library against Kinetoplastid Parasites

et al. 2017

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Kinetoplastid parasites cause vector-borne parasitic diseases including leishmaniasis, human African trypanosomiasis (HAT) and Chagas disease. These Neglected Tropical Diseases (NTDs) impact on some of the world’s lowest socioeconomic communities. Current treatments for these diseases cause severe toxicity and have limited efficacy, highlighting the need to identify new treatments. In this study, the Davis open access natural product-based library was screened against kinetoplastids (Leishmania donovani DD8, Trypanosoma brucei brucei and Trypanosoma cruzi) using phenotypic assays. The aim of this study was to identify hit compounds, with a focus on improved efficacy, selectivity and potential to target several kinetoplastid parasites. The IC50 values of the natural products were obtained for L. donovani DD8, T. b. brucei and T. cruzi in addition to cytotoxicity against the mammalian cell lines, HEK-293, 3T3 and THP-1 cell lines were determined to ascertain parasite selectivity. Thirty-one compounds were identified with IC50 values of ≤10 µM against the kinetoplastid parasites tested. Lissoclinotoxin E (1) was the only compound identified with activity across all three investigated parasites, exhibiting IC50 values <5 µM. In this study, natural products with the potential to be new chemical starting points for drug discovery efforts for kinetoplastid diseases were identified.

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Section: Introductionmentioning

confidence: 99%

Screening a Natural Product-Based Library against Kinetoplastid Parasites

et al. 2017

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“…Compound 1 was found inhibitory activity on the melanin production in mouse melanoma cells 11 and antiprotozoal activity. 12 Compound 2 significantly inhibited the shoot growth of cress and root growth of barnyard grass at concentrations greater than 1 mM (Figure 4). IC 50 values of compound 2 were 0.95 and 2.2 mM for cress shoots and barnyard grass roots, respectively.…”

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confidence: 96%

“…The 11,12 indicates compound 1 was (E,E)-2,4-undecadien-8,10-diynoic acid isobutylamide (anacycline, Figure 2). This is the first time that this alkamide with diene-diyne structure was isolated from A. oleracea leaves, but it has been previously isolated from Artemisia dracunculus, 11 Achillea ptarmica, and Anacyclus pyrethrum.…”

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confidence: 99%

“…This is the first time that this alkamide with diene-diyne structure was isolated from A. oleracea leaves, but it has been previously isolated from Artemisia dracunculus, 11 Achillea ptarmica, and Anacyclus pyrethrum. 12,13 The molecular formula of compound 2 was determined to be C 17 H 17 NO by using HRESIMS at m/z 252.1385 [M + H] + (calcd. for C 17 H 18 NO, 252.1388, Δ = −0.3 mmu).…”

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confidence: 99%

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Plant Growth Inhibitory Activity of the Extracts of Acmella oleracea and its Growth Inhibitory Substances

Kato‐Noguchi

Suwitchayanon

Boonmee

et al. 2019

Natural Product Communications

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Aqueous methanol extracts of Acmella oleracea inhibited the growth of roots and shoots of cress (Lepidum sativum), lettuce (Lactuca sativa), Italian ryegrass (Lolium multiflorum), and barnyard grass (Echinochloa crus-galli) with the extract concentration-dependent manner. The extracts were then purified and 2 growth inhibitory substances were isolated and identified by spectral data as (E,E)-2,4-undecadien-8,10-diynoic acid isobutylamide (compound 1) and nona-(2Z)-en-6,8-diynoic acid 2-phenylethylamide (compound 2). Compound 1 inhibited the growth of cress roots and shoots at concentrations greater than 0.3 mM and that of barnyard grass root at concentrations greater than 0.03 mM. Compound 2 inhibited the growth of cress shoots and barnyard grass roots at concentrations greater than 1 mM. The inhibition on the seedling growth indicates that both compounds had growth inhibitory activity and may contribute to the inhibitory effect of A. oleracea extracts. This is the first report of having growth inhibitory activity of compounds 1 and 2 on plants.

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“…L6 cells were used to evaluate the toxicity of each compound. Among the alkamides, undeca-2 E ,4 E -dien-8,10-diynoic acid isopentylamide showed the best activity (SI = 7), followed by tetradeca-2 E ,4 E ,12Z-trien-8,10-diynoic acid isobutylamide (SI = 3.9) and deca-2 E ,4 E ,9-trienoic acid isobutylamide (SI = 3.5) (Althaus et al, 2017).…”

Section: Alkamides From Anacyclus Pyrethrum (L) Link Are Active Agaimentioning

confidence: 99%

Asteraceae Plants as Sources of Compounds Against Leishmaniasis and Chagas Disease

et al. 2019

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Leishmaniasis and Chagas disease cause great impact on social and economic aspects of people living in developing countries. The treatments for these diseases are based on the same regimen for over 40 years, thus, there is an urgent need for the development of new drugs. In this scenario, Asteraceae plants (a family widely used in folk medicine worldwide) are emerging as an interesting source for new trypanocidal and leishmanicidal compounds. Herein, we provide a non-exhaustive review about the activity of plant-derived products from Asteraceae with inhibitory action toward Leishmania spp. and T. cruzi . Special attention was given to those studies aiming the isolation (or identification) of the bioactive compounds. Ferulic acid, rosmarinic acid, and ursolic acid ( Baccharis uncinella DC.) were efficient to treat experimental leishmaniasis; while deoxymikanolide ( Mikania micrantha ) and (+)-15-hydroxy-labd-7-en-17-al ( Aristeguietia glutinosa Lam.) showed in vivo anti- T. cruzi action. It is also important to highlight that several plant-derived products (compounds, essential oils) from Artemisia plants have shown high inhibitory potential against Leishmania spp., such as artemisinin and its derivatives. In summary, these compounds may help the development of new effective agents against these neglected diseases.

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Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity

Cited by 21 publications

References 16 publications

Screening a Natural Product-Based Library against Kinetoplastid Parasites

Screening a Natural Product-Based Library against Kinetoplastid Parasites

Plant Growth Inhibitory Activity of the Extracts of Acmella oleracea and its Growth Inhibitory Substances

Asteraceae Plants as Sources of Compounds Against Leishmaniasis and Chagas Disease

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