Structure–activity relationships of diverse xanthones against multidrug resistant human tumor cells

Wang, Qiwen; Ma, Chenyao; Ma, Yi; Li, Xiang; Chen, Yong; Chen, Jianwei

doi:10.1016/j.bmcl.2016.12.045

Cited by 10 publications

(7 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Curved spine, abnormal urogenital opening, pericardial edema, muscle necrosis, and reduced swim bladder were found as distinct aberrant phenotypes in larvae exposed to 9.4 μM of compound 7 , see Figure . Compound 7 has been reported to have cytotoxic effects in vitro. ,, As one of the least toxic compounds in this study, compound 8 demonstrated few visible phenotypical changes in larvae exposed to concentrations above the MTC-value (75 μM). Slow heart rate and reduced touch response appeared to be the most common toxic effects observed in larvae when exposed to higher concentrations, 100 and 200 μM.…”

Section: Resultsmentioning

confidence: 63%

“…Compound 7 has been reported to have cytotoxic effects in vitro. 20,36,48 As one of the least toxic compounds in this study, compound 8 demonstrated few visible phenotypical changes in larvae exposed to concentrations above the MTC-value (75 μM). Slow heart rate and reduced touch response appeared to be the most common toxic effects observed in larvae when exposed to higher concentrations, 100 and 200 μM.…”

Section: Toxicological Evaluation In Larval Zebrafishmentioning

confidence: 68%

“…49 In another study, compound 8 did not exhibit potent cytotoxic activity against the growth of different human tumor cell lines. 20 Studies on benzoates and xanthones isolated from S. longepedunculata are sparse. 2,3-Dimethoxy-4-hydroxy-benzophenone (compound 3) has showed low cytotoxicity against pancreatic cancer PANC-1 cells, 18 and in another study, 3 exhibited antiplasmodial activity.…”

Section: Toxicological Evaluation In Larval Zebrafishmentioning

confidence: 99%

See 2 more Smart Citations

Inhibition of Seizure-Like Paroxysms and Toxicity Effects of Securidaca longepedunculata Extracts and Constituents in Zebrafish Danio rerio

Moussavi,

van der Ent,

Diallo

et al. 2024

ACS Chem. Neurosci.

View full text Add to dashboard Cite

Plants used in traditional medicine in the management of epilepsy could potentially yield novel drug compounds with antiepileptic properties. The medicinal plant Securidaca longepedunculata is widely used in traditional medicine in the African continent, and epilepsy is among several indications. Limited knowledge is available on its toxicity and medicinal effects, such as anticonvulsant activities. This study explores the potential in vivo inhibition of seizure-like paroxysms and toxicity effects of dichloromethane (DCM) and ethanol (EtOH) extracts, as well as isolated xanthones and benzoates of S. longepedunculata. Ten phenolic compounds were isolated from the DCM extract. All of the substances were identified by nuclear magnetic resonance spectroscopy. Assays for toxicity and inhibition of pentylenetetrazole (PTZ)-induced seizure-like paroxysms were performed in zebrafish larvae. Among the compounds assessed in the assay for maximum tolerated concentration (MTC), benzyl-2-hydroxy-6-methoxy-benzoate (MTC 12.5 μM), 4,8-dihydroxy-1,2,3,5,6pentamethoxyxanthone (MTC 25 μM), and 1,7-dihydroxy-4-methoxyxanthone (MTC 6.25 μM) were the most toxic. The DCM extract, 1,7-dihydroxy-4-methoxyxanthone and 2-hydroxy-1,7-dimethoxyxanthone displayed the most significant inhibition of paroxysms by altering the locomotor behavior in GABA A receptor antagonist, PTZ, which induced seizures in larval zebrafish. The EtOH extract, benzyl benzoate, and benzyl-2-hydroxy-6-methoxy-benzoate unexpectedly increased locomotor activity in treated larval zebrafish and decreased locomotor activity in nontreated larval zebrafish, seemingly due to paradoxical excitation. The results reveal promising medicinal activities of this plant, contributing to our understanding of its use as an antiepileptic drug. It also shows us the presence of potentially new lead compounds for future drug development.

show abstract

Section: Resultsmentioning

confidence: 63%

Section: Toxicological Evaluation In Larval Zebrafishmentioning

confidence: 68%

Section: Toxicological Evaluation In Larval Zebrafishmentioning

confidence: 99%

See 1 more Smart Citation

Inhibition of Seizure-Like Paroxysms and Toxicity Effects of Securidaca longepedunculata Extracts and Constituents in Zebrafish Danio rerio

Moussavi,

van der Ent,

Diallo

et al. 2024

ACS Chem. Neurosci.

View full text Add to dashboard Cite

show abstract

“…Allaxanthone C, structurally close to 3, have been shown to induce a prolongation of survival in a xenograft murine model of human chronic lymphocytic leukemia 14 . 1,3,8-trihydroxy-2-methoxyxanthone 4 was also tested again different multidrugresistant human tumor cells and was moderately active against taxol resistant SMMC-7721 human liver carcinoma cell line (IC 50 = 42 µM) 15 . All of this suggest that xanthones structurally close to 3 or 4 should be tested against Hep3B cells lines in order to find a potential lead against hepatocellular carcinoma, however the activity of isolated compounds is rather moderate compared to the activity of the crude ethanolic extract of H. laricifolium (IC 50 = 11.5 µg/mL), suggesting that other compounds with better activity may be present in the plant, or that some synergetic effect may occur between the constituents of this species.…”

Section: Resultsmentioning

confidence: 99%

XANTONAS AISLADAS DE Hypericum laricifolium Juss. Y SU ACTIVIDAD ANTIPROLIFERATIVA CONTRA LAS CÉLULAS HEP3B

Moisela

Brel

Bourdy

et al. 2018

rsqp

View full text Add to dashboard Cite

En el presente trabajo se describe el aislamiento de 6 xantonas, una fenil-γ-pirona, el ácido 3-epibetulínico y quercetina a partir de las partes aéreas de Hypericum laricifolium Juss. (Hypericaceae), colectada en Perú. Los compuestos aislados fueron evaluados por su capacidad para inhibir el crecimiento de células de hepatocarcinoma humano Hep3B. El compuesto más activo fue la xantona 3, con una concentración inhibitoria (CI50) de 12 µM.

show abstract

“…It is known that small chemical changes can modulate, or drastically modify, the biological activities of dimeric xanthones [6]. For example, partial hydrogenation of one of the aromatic rings [7], and the presence of hydroxy [8] or amino [3] polar groups in the xanthone core can determine their biological profile. It is thus crucial to find new synthetic methods that allow for obtaining diverse dimeric xanthones rapidly and efficiently.…”

Section: Introductionmentioning

confidence: 99%

Expeditious Multicomponent Synthesis of Xanthone Dimers

Bornadiego¹,

Dı́az²,

Marcos³

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

Xanthones are a type of compound widely found in many natural products from plants, fungi, and lichens and are considered privileged structures. Frequently, xanthones occur in nature as dimers, which often exhibit singular and potent biological effects. Although diverse methods for the synthesis of monomeric xanthones are known, dimeric xanthones remain synthetically challenging targets. Reported syntheses of dimeric xanthones are very scarce, and invariably involve a large number of synthetic steps. We have recently developed a multicomponent synthesis of xanthones starting from 3-carbonylchromones, isocyanides, and dienophiles. Here we report a similar one-pot tandem procedure, involving a [4+1]-[4+2] cycloaddition, that readily affords dimeric xanthones and dihydroxanthones, which are structurally similar to bioactive ergochromes.

show abstract

Structure–activity relationships of diverse xanthones against multidrug resistant human tumor cells

Cited by 10 publications

References 17 publications

Inhibition of Seizure-Like Paroxysms and Toxicity Effects of Securidaca longepedunculata Extracts and Constituents in Zebrafish Danio rerio

Inhibition of Seizure-Like Paroxysms and Toxicity Effects of Securidaca longepedunculata Extracts and Constituents in Zebrafish Danio rerio

XANTONAS AISLADAS DE Hypericum laricifolium Juss. Y SU ACTIVIDAD ANTIPROLIFERATIVA CONTRA LAS CÉLULAS HEP3B

Expeditious Multicomponent Synthesis of Xanthone Dimers

Contact Info

Product

Resources

About