Pyranochromones from <i>Dictyoloma vandellianum</i> A. <scp>Juss</scp> and Their Cytotoxic Evaluation

Alves, Iura Muniz; Abreu, Lucas Silva; Costa, Carlos Maurício de Castro; Hyaric, Mireille Le; Guédès, Michel; Soares, Milena Botelho Pereira; Bezerra, Daniel P.; Velozo, Eudes da Silva

doi:10.1002/cbdv.201600276

Cited by 10 publications

(6 citation statements)

References 11 publications

(15 reference statements)

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“…The structure of this compound and the corresponding acetyl derivative 1a were elucidated by 1D and 2D NMR, HRESIMS and IR. In addition, a known quinolone alkaloid previously described was identified as casimiroine (2), isolated from the same species. 9 The compounds obtained were screened for their cytotoxic activities.…”

Section: Introductionmentioning

confidence: 90%

“…1 Previous phytochemical investigations of D. vandellianum have demonstrated the presence of limonoids, quinolone alkaloids, and pyranochromones. [2][3][4][5] Although hundreds of limonoids have been isolated from various plants, their occurrence in the plant kingdom is limited to plants belonging to Rutales, especially Meliaceae and Rutaceae. 6,7 Therefore, these compounds have been important for systematic classification of the genus in the Rutaceae family.…”

Section: Introductionmentioning

confidence: 99%

“…3,8,9 Recently, it was evaluated the antinociceptive activity of hydrolysable tannins isolated from the methanol extract from leaves, anti-inflammatory activity and cytotoxic of pyranochromones from dichloromethane extract from root barks of D. vandellianum. 2,10 Natural products continue to be a major source of new drugs, and they may be used as prototypes for design of lead molecules. 11,12 From 1940 to 2014, 175 small molecules were approved for cancer treatment, nearly half were natural products or directly derived from them.…”

Section: Introductionmentioning

confidence: 99%

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A NEW SECO-LIMONOID FROM THE INFLORESCENCES OF Dictyoloma vandellianum

Pereira¹,

Abreu²,

Silveira³

et al. 2020

Quim. Nova

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Section: Introductionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A NEW SECO-LIMONOID FROM THE INFLORESCENCES OF Dictyoloma vandellianum

Pereira¹,

Abreu²,

Silveira³

et al. 2020

Quim. Nova

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“…69163) has been deposited at the Herbarium Alexandre Leal Costa. The procedures used for the purification of 5-CK have been described [62]. The percent purity of 5-CK used in the pharmacological experiments carried out was greater than 98%, as determined by high performance liquid chromatography.…”

Section: Animalsmentioning

confidence: 99%

5-O-methylcneorumchromone K Exerts Antinociceptive Effects in Mice via Interaction with GABAA Receptors

Opretzka

Freitas

Santo

et al. 2021

IJMS

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The proper pharmacological control of pain is a continuous challenge for patients and health care providers. Even the most widely used medications for pain treatment are still ineffective or unsafe for some patients, especially for those who suffer from chronic pain. Substances containing the chromone scaffold have shown a variety of biological activities, including analgesic effects. This work presents for the first time the centrally mediated antinociceptive activity of 5-O-methylcneorumchromone K (5-CK). Cold plate and tail flick tests in mice showed that the 5-CK-induced antinociception was dose-dependent, longer-lasting, and more efficacious than that induced by morphine. The 5-CK-induced antinociception was not reversed by the opioid antagonist naloxone. Topological descriptors (fingerprints) were employed to narrow the antagonist selection to further investigate 5-CK’s mechanism of action. Next, based on the results of fingerprints analysis, functional antagonist assays were conducted on nociceptive tests. The effect of 5-CK was completely reversed in both cold plate and tail-flick tests by GABAA receptor antagonist bicuculline, but not by atropine or glibenclamide. Molecular docking studies suggest that 5-CK binds to the orthosteric binding site, with a similar binding profile to that observed for bicuculline and GABA. These results evidence that 5-CK has a centrally mediated antinociceptive effect, probably involving the activation of GABAergic pathways.

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“…vandellianum have led to the isolation of several limonoids, quinolone alkaloids and chromones [14–17]. These classes of compounds display a wide range of biological effects, such as anti-tumor, anti-malarial, anti-leishmania, anti-microbial, anti-inflammatory and anti-viral [17–22]. Recently, relevant anti-inflammatory properties of chromones isolated from D .…”

Section: Introductionmentioning

confidence: 99%

Antinociceptive compounds and LC-DAD-ESIMSn profile from Dictyoloma vandellianum leaves

et al. 2019

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Limonoids, quinolone alkaloids and chromones have been reported as constituents of Dictyoloma vandellianum Adr. Juss. (Rutaceae). Although those compounds are known for their biological activities, only the anti-inflammatory activity of chromones isolated from the underground parts has been evaluated. There are no studies of the pharmacological properties of the aerial parts of D. vandellianum. The present study was carried out to determine the phytochemical profile and antinociceptive activity of the methanol extract, fractions and isolated compounds of leaves of D. vandellianum. The phytochemical profile was performed by HLPC-DAD-ESIMSn and pure substances obtained were characterized by MS and NMR spectroscopy. The antinociceptive activity was assessed using the formalin assay in mice, and the motor function in the rotarod test. ME and all the fractions obtained from ME produced antinociceptive effects. Among them, the ethyl ether fraction was the most active. Data from HPLC-DAD-ESIMSn showed that the ethyl ether fraction presented 42 compounds. The major compounds isolated from this fraction—gallic acid, methyl gallate and 1,2,6-tri-O-galloyl-β-d-glucopyranose–were tested and produced antinociceptive effects. Gallic acid, methyl gallate and 1,2,6-tri-O-galloyl-β-d-glucopyranose at antinociceptive doses did not affect the motor performance in mice in the rotarod test. This work is the first report of the occurrence of gallotanins in D. vandellianum. In addition, the pharmacological study showed that D. vandellianum leaves present antinociceptive activity, probably induced by gallic acid, methyl gallate and 1,2,6-tri-O-galloyl-β-d-glucopyranose.

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Pyranochromones from Dictyoloma vandellianum A. Juss and Their Cytotoxic Evaluation

Cited by 10 publications

References 11 publications

A NEW SECO-LIMONOID FROM THE INFLORESCENCES OF Dictyoloma vandellianum

A NEW SECO-LIMONOID FROM THE INFLORESCENCES OF Dictyoloma vandellianum

5-O-methylcneorumchromone K Exerts Antinociceptive Effects in Mice via Interaction with GABAA Receptors

Antinociceptive compounds and LC-DAD-ESIMSn profile from Dictyoloma vandellianum leaves

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