Chemical constituents from Waltheria indica exert in vitro activity against Trypanosoma brucei and T. cruzi

Cretton, Sylvian; Bréant, Lise; Pourrez, Lucie; Ambuehl, Chiara; Perozzo, Remo; Marcourt, Laurence; Kaiser, Marcel; Cuendet, Muriel; Christen, Philippe

doi:10.1016/j.fitote.2015.06.007

Cited by 45 publications

(30 citation statements)

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“…Cretton et al. isolated waltheriones A ( 121 ), C ( 122 ), and E‒L ( 123 ‒ 130 ), together with antidesmone and 8‐deoxoantidesmone ( 131 ) (Figure ) from Waltheria indica in the years 2014 and 2015 . Compounds 125 , 126 , and 129 (Figure ) showed potent and selective growth inhibition toward Trypanosoma cruzi with IC 50 values of 0.02 ( 125 ) and 0.04 ( 126 , 129 ) μM.…”

Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

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Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

158

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To follow-up on our prior Part I review, this Part II review summarizes and provides updated literature on novel quinoline and quinazoline alkaloids isolated during the period of 2009-2016, together with the biological activity and the mechanisms of action of these classes of natural products. Over 200 molecules with a broad range of biological activities, including antitumor, antiparasitic and insecticidal, antibacterial and antifungal, cardioprotective, antiviral, anti-inflammatory, hepatoprotective, antioxidant, anti-asthma, antitussive, and other activities, are discussed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

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Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

“…Thus, the selectivity index (SI: IC 50 cytotoxicity/IC 50 anti‐T. cruzi activity) values of most of the waltheriones ranged from 1.8 to 33.8, making them too toxic to be considered as antichagasic hits . The sole exception was 122 with a cytotoxicity IC 50 of 101 μM and better SI of 52.4 …”

Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

158

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“…A complementary LC-MS-based dereplication indicated that the more lipophilic NPs belong to the quinoline alkaloids waltherione C, E, and G and to flavonoid aglycones, whereas the more polar group of constituents included cyclopeptide alkaloids adouetin X and Y [33,34]. The effective passive permeability values of the pharmacologically active waltheriones C, E, and G were calculated and such compounds were found to have medium permeability (l " Fig.…”

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confidence: 99%

“…Compared to the medium permeant waltherione C, waltherione A bears an additional hydroxy group in the cycloheptane ring (Fig. S1, Supporting Information) [34]. The crude extract of P. montana var.…”

mentioning

confidence: 99%

“…Phellopterin (≥ 99 %) and isoimperatorin (≥ 98%) was purchased from PhytoLab GmbH. Waltherione A, C, E, and G were isolated and dereplicated from W. indica as previously described (minimum purity of 95 %) [33,34]. (50 g) were powdered and extracted with 0.5 L of boiling water for 1 h. After filtration, the aqueous extract was evaporated and concentrated to 100 mL.…”

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Prediction of the Passive Intestinal Absorption of Medicinal Plant Extract Constituents with the Parallel Artificial Membrane Permeability Assay (PAMPA)

et al. 2016

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At the early drug discovery stage, the high-throughput parallel artificial membrane permeability assay is one of the most frequently used in vitro models to predict transcellular passive absorption. While thousands of new chemical entities have been screened with the parallel artificial membrane permeability assay, in general, permeation properties of natural products have been scarcely evaluated. In this study, the parallel artificial membrane permeability assay through a hexadecane membrane was used to predict the passive intestinal absorption of a representative set of frequently occurring natural products. Since natural products are usually ingested for medicinal use as components of complex extracts in traditional herbal preparations or as phytopharmaceuticals, the applicability of such an assay to study the constituents directly in medicinal crude plant extracts was further investigated. Three representative crude plant extracts with different natural product compositions were chosen for this study. The first extract was composed of furanocoumarins (Angelica archangelica), the second extract included alkaloids (Waltheria indica), and the third extract contained flavonoid glycosides (Pueraria montana var. lobata). For each medicinal plant, the effective passive permeability values Pe (cm/s) of the main natural products of interest were rapidly calculated thanks to a generic ultrahigh-pressure liquid chromatography-UV detection method and because Pe calculations do not require knowing precisely the concentration of each natural product within the extracts. The original parallel artificial membrane permeability assay through a hexadecane membrane was found to keep its predictive power when applied to constituents directly in crude plant extracts provided that higher quantities of the extract were initially loaded in the assay in order to ensure suitable detection of the individual constituents of the extracts. Such an approach is thus valuable for the high-throughput, cost-effective, and early evaluation of passive intestinal absorption of active principles in medicinal plants. In phytochemical studies, obtaining effective passive permeability values of pharmacologically active natural products is important to predict if natural products showing interesting activities in vitro may have a chance to reach their target in vivo.

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Design, Synthesis and Biological Activity of C3 Hemisynthetic Triterpenic Esters as Novel Antitrypanosomal Hits

et al. 2021

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Research for innovative drugs is crucial to contribute to parasitic infections control and eradication. Inspired by natural antiprotozoal triterpenes, a library of 12 hemisynthetic 3‐ O ‐arylalkyl esters was derived from ursolic and oleanolic acids through one‐step synthesis. Compounds were tested on Trypanosoma , Leishmania and the WI38 cell line alongside with a set of triterpenic acids. Results showed that the triterpenic C3 esterification keeps the antitrypanosomal activity (IC 50 ≈1.6–5.5 μ m ) while reducing the cytotoxicity compared to parent acids. Unsaturation of the ester alkyl chain leads to an activity loss interestingly kept when a sterically hindered group replaces the double bond or shields the ester group. An ursane/oleanane C3 hydroxylation was the only important feature for antileishmanial activity. Two candidates, dihydrocinnamoyl and 2‐fluorophenylpropionyl ursolic acids, were tested on an acute mouse model of African trypanosomiasis with significant parasitemia reduction at day 5 post‐infection for the dihydrocinnamoyl derivative. Further evaluation on other alkyl/protective groups should be investigated both in vitro and in vivo .

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Chemical constituents from Waltheria indica exert in vitro activity against Trypanosoma brucei and T. cruzi

Cited by 45 publications

References 28 publications

Biologically active quinoline and quinazoline alkaloids part II

Biologically active quinoline and quinazoline alkaloids part II

Prediction of the Passive Intestinal Absorption of Medicinal Plant Extract Constituents with the Parallel Artificial Membrane Permeability Assay (PAMPA)

Design, Synthesis and Biological Activity of C3 Hemisynthetic Triterpenic Esters as Novel Antitrypanosomal Hits

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