Seasonality effect on the composition of oxindole alkaloids from distinct organs of Uncaria tomentosa from the Caribbean region of Costa Rica

Alvarenga-Venutolo, Silvana; Rosales-López, Catalina; Sánchez-Chinchilla, Luis; Muñoz-Arrieta, Rodrigo; Aguilar-Cascante, Francisco

doi:10.1016/j.phytochem.2018.03.008

Cited by 9 publications

(5 citation statements)

References 17 publications

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“…Similarly, the other oxindoles examined, corynoxine ( 1 ) (0–0.42 mg/g) and its epimer, corynoxine B ( 2 ) (0 to 0.17 mg/g), were inconsistent in their representation with previously investigated specimens. In Uncaria species, the oxindole content is known to be affected by environment and seasonal factors such as total precipitation and plant water content. , It is therefore possible that oxindole alkaloid biosynthesis from their indole precursors requires certain levels of water and oxygen. A short discussion about the biosynthesis of the kratom alkaloids (Figure S2) is provided in the Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

“…In Uncaria species, the oxindole content is known to be affected by environment and seasonal factors such as total precipitation and plant water content. 18,19 It is therefore possible that oxindole alkaloid biosynthesis from their indole precursors requires certain levels of water and oxygen. A short discussion about the biosynthesis of the kratom alkaloids (Figure S2) is provided in the Supporting Information.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors

et al. 2021

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Ten indole and oxindole alkaloids (1–10) were isolated from the freshly collected leaves of Malaysian Mitragyna speciosa (Kratom). The chemical structures of these compounds were established on the basis of extensive 1D and 2D NMR and HRMS data analysis. The spectroscopic data of mitragynine oxindole B (4) are reported herein for the first time. The spatial configuration of mitragynine oxindole B (4) was confirmed by single-crystal X-ray diffraction. Simultaneous quantification of the isolated alkaloids in the M. speciosa leaf specimens collected from different locations in the northern region of Peninsular Malaysia was also performed using UPLC-MS/MS. The oxindole alkaloids (1–4) and the indole alkaloid (10) were assessed for binding affinity at opioid receptors. Corynoxine (1) showed high binding affinity to μ-opioid receptors with a K i value of 16.4 nM. Further, corynoxine (1) was 1.8-fold more potent than morphine in rats subjected to a nociceptive hot plate assay. These findings have important implications for evaluating the combined effects of the minor oxindole alkaloids in the overall therapeutic activity of M. speciosa.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors

et al. 2021

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“…Beyond these, many others factors can have significant qualitative and quantitative effects on the production of secondary metabolites that represent a chemical interface between plants and the environment. Consequently, the metabolic pathways can be altered, leading to the biosynthesis of different compounds, or the same compounds in different proportions, according to the stimulus provided by the environment in which the plant is located (Morais 2009;Alvarenga-Venutolo et al 2018).…”

Section: Introductionmentioning

confidence: 99%

Biological studies and chromatograms aided by chemometric analysis in evaluation of seasonality and extraction method of Croton grewioides extracts

et al. 2022

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The genus Croton is the second largest genus of Euphorbiaceae family, comprising more than 1300 registered species. The species Croton grewioides is endemic in the northeast of Brazil and distributed mainly throughout the caatinga biome presenting, in its essential oils, various compounds with biological activities such as pupicidal, larvicidal, insecticidal, and bactericidal. The secondary metabolites commonly found in their extracts include diterpenes, phenols, steroids, and aglycone and glycoside flavonoids derivatives, which can undergo variations based on climatic changes that modify processes such as photosynthesis, transpiration and nutrient cycle. To understand the effects of seasonal variability and extraction method on the biological activities of polar extracts from C. grewioides, fingerprint chromatograms were analyzed aided by chemometric analysis. In vitro assays of cytotoxicity against HL-60 and HepG2 cancer cells and anti-acetylcholinesterase activity were performed. Seasonal effects could only be observed in the chemical profiles of the methanolic and ethanolic extracts from accessions 113 and 126, respectively. Considering the extraction method, the chromatograms of aqueous and hydroalcoholic extracts of all the accessions were similar, but differed from those for the corresponding methanolic and ethanolic extracts. Five hexane partitions were active against HL-60 cell line, displaying inhibition values between 81 and 93%. Only the ethanolic extract of accession 101 (winter), the methanolic partition from the methanolic extract, and the decoction of accession 113 (winter) presented high inhibition values against the acetylcholinesterase enzyme. This study enabled elucidation of the effects of seasonality and extraction method on the biological activities presented by the C. grewioides extracts.

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“…Uncaria tomentosa (Willd.) DC belongs to the Rubiaceae family, it is a plant species of the Amazon region, popularly known as cat's claw (Alvarenga et al, 2018). This species has various medicinal properties such as anti-inflammatory (Yatoo et al, 2018), anticancer (Zhang et al, 2015), contraceptive (Nogueira et al, 2011), antiasthmatic (Azevedo et al, 2018), antiarthritic (Rajamanikyam et al, 2017, and immunostimulant (Baraya et al, 2017) activities, mainly antibacterial activity of endophytic fungi extracts, especially against Enterecoccus faecalis (Rodrigues et al, 2018), which is a Gram-positive bacterium, ubiquitous, highly resistant and commonly found in the root canal system (Qian- Wang et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Chromatography and bioautography of endophytic fungi extracts of Uncaria tomentosa (Willd.) DC with antibacterial activity

Gonã‡Alves¹,

ARAÃšJO²,

Brasil³

et al. 2019

J. Med. Plants Res.

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Endophytic fungi of different species have already proved their efficacy against a range of pathogenic bacteria. However, the separation of the compounds contained in these extracts that actually have an effective activity is not a constant, but it is essential for the scientific knowledge to formulate a new medication. Thus, this study aimed to separate compounds from two endophytic fungi extracts of Uncaria tomentosa with positive results against Gram-positive and Gram-negative bacteria. The separation was carried out by thin-layer chromatography and bioautography. For this, it was necessary to produce fungal extracts from the endophytes Colletotrichum (23916) and Fusarium (23952), which were separated from the liquid state by filtration. The remaining filtrate was divided into ethyl acetate and then concentrated in a rotary evaporator at 40°C. Antimicrobial activity was evaluated and the Minimum Inhibitory Concentration (MIC) was determined with the following test microorganisms: Escherichia coli, Enterecoccus faecalis, Klebsiella pneumoniae and Staphylococcus aureus. Subsequently, it was carried out the thin layer chromatography (TLC) of the extracts using hexane, ethyl acetate/hexane, ethyl acetate and acetate/methanol. The reading was performed in 312 nm UV light, and right after the chromatography, the bioautography was carried out. The following Rf values were obtained: 0.30 for K. pneumoniae and 0.35 for E. coli, in ethyl acetate, for the extract 23952, and 0.81 for K. pneumoniae and 0.41 for S. aureus, in styrene acetate, for the extract 23916, confirming different compounds by bioautography. Therefore, it was concluded that several compounds present in the extracts tested have antibacterial activity.

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Seasonality effect on the composition of oxindole alkaloids from distinct organs of Uncaria tomentosa from the Caribbean region of Costa Rica

Cited by 9 publications

References 17 publications

Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors

Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors

Biological studies and chromatograms aided by chemometric analysis in evaluation of seasonality and extraction method of Croton grewioides extracts

Chromatography and bioautography of endophytic fungi extracts of Uncaria tomentosa (Willd.) DC with antibacterial activity

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