Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium

Presley, Christopher C; Du, Yongle; Dalal, Seema; Merino, Emilio F.; Butler, Joshua H.; Rakotonandrasana, Stéphan; Rasamison, Vincent E.; Cassera, María B.; Kingston, David G. I.

doi:10.1016/j.bmc.2017.06.017

Cited by 15 publications

(10 citation statements)

References 28 publications

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“…Importantly, the presence of the 1,3,5-trioxepane-ring in 132 and 134 correlated with improved activity [103]. Another bioassay-guided purification, this time of Crinim firmifolium leaf extract, led to the isolation of the new 2-alkylquinolinones 136 and the known 137 , which were both active against the 3D7 and Dd2 strains with mild cytotoxicity against A2780 mammalian ovarian cancer cells [104]. Incorporation of a branched alkyl into 137 to form 138 improved antiplasmodial activity, suggesting that branching of the alkyl side chain is beneficial to potency [104].…”

Section: Alkaloidsmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

122

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BackgroundMalaria remains a significant public health challenge in regions of the world where it is endemic. An unprecedented decline in malaria incidences was recorded during the last decade due to the availability of effective control interventions, such as the deployment of artemisinin-based combination therapy and insecticide-treated nets. However, according to the World Health Organization, malaria is staging a comeback, in part due to the development of drug resistance. Therefore, there is an urgent need to discover new anti-malarial drugs. This article reviews the literature on natural products with antiplasmodial activity that was reported between 2010 and 2017.MethodsRelevant literature was sourced by searching the major scientific databases, including Web of Science, ScienceDirect, Scopus, SciFinder, Pubmed, and Google Scholar, using appropriate keyword combinations.Results and DiscussionA total of 1524 compounds from 397 relevant references, assayed against at least one strain of Plasmodium, were reported in the period under review. Out of these, 39% were described as new natural products, and 29% of the compounds had IC50 ≤ 3.0 µM against at least one strain of Plasmodium. Several of these compounds have the potential to be developed into viable anti-malarial drugs. Also, some of these compounds could play a role in malaria eradication by targeting gametocytes. However, the research into natural products with potential for blocking the transmission of malaria is still in its infancy stage and needs to be vigorously pursued.

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Section: Alkaloidsmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

122

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“…These activities have been attributed to the presence of alkaloids in these Crinum species. [5][6][7][8][9] Crinum pedunculatum, also known as swamp lily, belongs to the family Amaryllidaceae. Plants of the Crinum species have been reported to contain phytoconstituents such as coumarins, catechic tannins, triterpenes, anthocyanidins, polyphenols among others.…”

Section: Introductionmentioning

confidence: 99%

Analgesic, Anti-inflammatory, and Anti-pyretic Activities of Crinum pedunculatum R.Br. Bulb Extracts

Doe¹,

Danquah²,

Ohemeng³

et al. 2021

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Background: Crinum pedunculatum R.Br. bulbs are used for the topical management of inflammation by traditional healers in the southern region of Ghana. Objectives: This study aims to assess the analgesic, anti-inflammatory, and anti-pyretic activities of different solvent extracts of Crinum pedunculatum. Methods: The analgesic, anti-inflammatory, and anti-pyretic activities of the bulb extracts of Crinum pedunculatum were determined in rats at doses of 100, 200, and 400 mg/kg. The acetic acid induced writhing test was used to determine the analgesic activity, carrageenan was employed to determine the anti-inflammatory activity, and Brewer's yeast-induced pyrexia was studied to evaluate the extract's anti-pyretic activity. Results: All solvent extracts of Crinum pedunculatum significantly decreased (P < 0.001) the frequency of writhing in rats at all doses with 400 mg/kg of the ethanolic extract showing a 98% inhibition comparable to that obtained with diclofenac sodium at 94%. These extracts also caused the inhibition of the increase in paw diameter induced by the administration of carrageenan with 400 mg/kg of the ethyl acetate extract of Crinum pedunculatum causing a 97% inhibition of paw oedema. All doses (100, 200, and 400 mg/kg) of the methanol extract caused a significant decrease (P < 0.0001) in the temperature of rats induced via the administration of yeast with ethanol and ethyl acetate extracts also showed a significant reduction (P < 0.001) in rectal temperature. Conclusion: These results obtained indicate that the methanolic, ethanolic, and ethyl acetate extracts of Crinum pedunculatum R.Br. possess analgesic, anti-inflammatory, and antipyretic activities.

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“…Many of these compounds (PQS) have been previously isolated for their antibiotic, antifungal, and anti-algal activity against human, plant, and animal pathogens (58). Several previous studies have also explored the antimalarial potential of alkylquinolones (59)(60)(61). In particular, the compounds were isolated from different strains of P. aeruginosa, which inhibited the growth P. falciparum (58).…”

Section: Discussionmentioning

confidence: 99%

Detection of Quorum Sensing Signal Molecules, Particularly N-Acyl Homoserine Lactones, 2-Alky-4-Quinolones, and Diketopiperazines, in Gram-Negative Bacteria Isolated From Insect Vector of Leishmaniasis

Mesa¹,

Higuita-Castro²,

Robledo³

et al. 2021

Front. Trop. Dis

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Gram-negative bacteria are known to use a quorum sensing system to facilitate and stimulate cell to cell communication, mediated via regulation of specific genes. This system is further involved in the modulation of cell density and metabolic and physiological processes that putatively either affect the survival of insect vectors or the establishment of pathogens transmitted by them. The process of quorum sensing generally involves N-acyl homoserine lactones and 2-alkyl-4-quinolones signaling molecules. The present study aimed to detect and identify quorum sensing signaling molecules of AHLs and AHQs type that are secreted by intestinal bacteria, and link their production to their extracellular milieu and intracellular content. Isolates for assessment were obtained from the intestinal tract of Pintomyia evansi (Leishmania insect vector). AHLs and AHQs molecules were detected using chromatography (TLC) assays, with the aid of specific and sensitive biosensors. For identity confirmation, ultra-high-performance liquid chromatography coupled with mass spectrometry was used. TLC assays detected quorum sensing molecules (QSM) in the supernatant of the bacterial isolates and intracellular content. Interestingly, Pseudomonas otitidis, Enterobacter aerogenes, Enterobacter cloacae, and Pantoea ananatis isolates showed a migration pattern similar to the synthetic molecule 3-oxo-C6-HSL (OHHL), which was used as a control. Enterobacter cancerogenus secreted C6-HSL, a related molecules to N-hexanoyl homoserine lactone (HHL), while Acinetobacter gyllenbergii exhibited a migration pattern similar to 2-heptyl-4-quinolone (HHQ) molecules. In comparison to this, 3-oxo-C12-HSL (OdDHL) type molecules were produced by Lysobacter soli, Pseudomonas putida, A. gyllenbergii, Acinetobacter calcoaceticus, and Pseudomonas aeruginosa, while Enterobacter cloacae produced molecules similar to 2-heptyl-3-hydroxy-4-quinolone (PQS). For Pseudomonas putida, Enterobacter aerogenes, P. ananatis, and Pseudomonas otitidis extracts, peak chromatograms with distinct retention times and areas, consistent with the molecules described in case of TLC, were obtained using HPLC. Importantly, P. ananatis produced a greater variety of high QSM concentration, and thus served as a reference for confirmation and identification by UHPLC-MRM-MS/MS. The molecules that were identified included N-hexanoyl-L-homoserine lactone [HHL, C10H18NO3, (M + H)], N-(3-oxohexanoyl)-L-homoserine lactone [OHHL, C10H16NO4, (M + H)], N-(3-oxododecanoyl)-L-homoserine lactone [OdDHL, C16H28NO4, (M + H)], and 2-heptyl-3-hydroxy-4(1H)-quinolone [PQS, C16H22NO2, (M + H)]. Besides this, the detection of diketopiperazines, namely L-Pro-L-Tyr and ΔAla-L-Val cyclopeptides was reported for P. ananatis. These molecules might be potentially associated with the regulation of QSM system, and might represent another small molecule-mediated bacterial sensing system. This study presents the first report regarding the detection and identification of QSM and diketopiperazines in the gut sand fly bacteria. The possible effect of QSM on the establishment of Leishmania must be explored to determine its role in the modulation of intestinal microbiome and the life cycle of Pi. evansi.

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Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium

Cited by 15 publications

References 28 publications

Antiplasmodial natural products: an update

Antiplasmodial natural products: an update

Analgesic, Anti-inflammatory, and Anti-pyretic Activities of Crinum pedunculatum R.Br. Bulb Extracts

Detection of Quorum Sensing Signal Molecules, Particularly N-Acyl Homoserine Lactones, 2-Alky-4-Quinolones, and Diketopiperazines, in Gram-Negative Bacteria Isolated From Insect Vector of Leishmaniasis

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