A Review on the Cytotoxic and Antimicrobial Properties of Xanthones from Cratoxylum cochinchinense

Lee, Su Young; Mojulat, Monjia; Thangaperagasam, Grace; Surugau, Noumie; Tan, Sheri; Jhon, Oliver

doi:10.11594/jtls.13.01.20

Cited by 3 publications

(3 citation statements)

References 46 publications

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“…Finding selective drugs with low toxicity to normal cells that are not Pgp substrates may thus be one of the ways to effectively treat this disease. Several studies concerning the evaluation of the biologic activity of xanthones demonstrated that they often present anti-tumor activity [13,[30][31][32], besides many other interesting biological activities, including anti-oxidant, anti-inflammatory, anti-allergy, anti-bacterial, anti-fungal, and anti-viral activities [12,33,34]. Some cell targets for xanthone derivatives have already been described and include, among others, cyclin dependent kinases, important in cell cycle control [35,36], cytokines, kinases that modulate the activity of PI3K, Akt, and TOR proteins or proteins involved in apoptosis, like Bax, Bcl-2, or caspase 3 [37].…”

Section: Effect Of Chiral Derivatives Of Xanthones On the Growth Of H...mentioning

confidence: 99%

Evaluation of Antitumor Activity of Xanthones Conjugated with Amino Acids

Barbosa,

Araújo,

Gonçalves

et al. 2024

IJMS

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Cancer is a complex disease characterized by several alterations, which confer, to the cells, the capacity to proliferate uncontrollably and to resist cellular death. Multiresistance to conventional chemotherapy drugs is often the cause of treatment failure; thus, the search for natural products or their derivatives with therapeutic action is essential. Chiral derivatives of xanthones (CDXs) have shown potential inhibitory activity against the growth of some human tumor cell lines. This work reports the screening of a library of CDXs, through viability assays, in different cancer cell lines: A375-C5, MCF-7, NCI-H460, and HCT-15. CDXs’ effect was analyzed based on several parameters of cancer cells, and it was also verified if these compounds were substrates of glycoprotein-P (Pgp), one of the main mechanisms of resistance in cancer therapy. Pgp expression was evaluated in all cell lines, but no expression was observed, except for HCT-15. Also, when a humanized yeast expressing the human gene MDR1 was used, no conclusions could be drawn about CDXs as Pgp substrates. The selected CDXs did not induce significant differences in the metabolic parameters analyzed. These results show that some CDXs present promising antitumor activity, but other mechanisms should be triggered by these compounds.

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Section: Effect Of Chiral Derivatives Of Xanthones On the Growth Of H...mentioning

confidence: 99%

Evaluation of Antitumor Activity of Xanthones Conjugated with Amino Acids

Barbosa,

Araújo,

Gonçalves

et al. 2024

IJMS

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“…Nevertheless, their unique structures inspire the design of new analogues with similar biological actions. Among the natural products with different therapeutic uses, xanthone derivatives, representing a great diversity of compounds, possess a broad spectrum of biological and pharmacological activities [ 2 , 3 , 4 , 5 ], such as anticancer [ 6 , 7 ], antimicrobial [ 8 , 9 ], and anti-inflammatory [ 10 , 11 ] activities. For example, disease-preventative and therapeutic properties of mangosteen ( Garcinia mangostana ), also known as the “queen of fruits”, have been ascribed to xanthone derivatives that are present in several parts of the tree, including the pericarp, fruit rind, peel, stem bark, root bark, and leaf [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“… 1. H NMR (400.14 MHz, DMSO-d 6 ): δ = 8.46 (1H, d, J = 7.8 Hz, N-H), 8.18 (1H, dd, J = 8.0 and 1 5. Hz, H-8), 8.13 (1H, d, J = 8 7.…”

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Synthesis and Anti-Inflammatory Evaluation of a Library of Chiral Derivatives of Xanthones Conjugated with Proteinogenic Amino Acids

Vieira

Araújo

Gonçalves

et al. 2023

IJMS

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In recent decades, the relationship between drug chirality and biological activity has been assuming enormous importance in medicinal chemistry. Particularly, chiral derivatives of xanthones (CDXs) have interesting biological activities, including enantioselective anti-inflammatory activity. Herein, the synthesis of a library of CDXs is described, by coupling a carboxyxanthone (1) with both enantiomers of proteinogenic amino esters as chiral building blocks (2–31), following the chiral pool strategy. The coupling reactions were performed at room temperature with good yields (from 44 to 99.9%) and very high enantiomeric purity, with most of them presenting an enantiomeric ratio close to 100%. To afford the respective amino acid derivatives (32–61), the ester group of the CDXs was hydrolyzed in mild alkaline conditions. Consequently, in this work, sixty new derivatives of CDXs were synthetized. The cytocompatibility and anti-inflammatory activity in the presence of M1 macrophages were studied for forty-four of the new synthesized CDXs. A significant decrease in the levels of a proinflammatory cytokine targeted in the treatment of several inflammatory diseases, namely interleukin 6 (IL-6), was achieved in the presence of many CDXs. The amino ester of L-tyrosine (X1AELT) was the most effective in reducing IL-6 production (52.2 ± 13.2%) by LPS-stimulated macrophages. Moreover, it was ≈1.2 times better than the D-enantiomer. Indeed, enantioselectivity was observed for the majority of the tested compounds. Thus, their evaluation as promising anti-inflammatory drugs should be considered.

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Isolation and Pharmacochemistry of  α-Mangostin as a Chemotherapeutic Agent

Meah,

Panichayupakaranant,

Sayeed

et al. 2024

Pharmacognosy Magazine

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A naturally occurring xanthone, mangostanin (1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9 H-xanthen-9-one), was isolated from Garcinia mangostana L. It demonstrates a range of pharmacological effects, such as antibacterial, antifungal, antiviral, anti-inflammatory, and anticancer activity. The α-mangostin’s isoprenyl and benzopyrone skeleton side chains are crucial to its antibacterial activity. In this review, we review the current approach for the isolation of α-mangostin from plant sources and the recent report on its biological activity. The structure–activity relationship is discussed to demonstrate the pharmacophore of α-mangostin responsible for its anti-infective properties, including antibacterial, antifungal, and antiviral activities. The potential approaches for developing α-mangostin for the treatment of infectious diseases are proposed as future perspectives.

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A Review on the Cytotoxic and Antimicrobial Properties of Xanthones from Cratoxylum cochinchinense

Cited by 3 publications

References 46 publications

Evaluation of Antitumor Activity of Xanthones Conjugated with Amino Acids

Evaluation of Antitumor Activity of Xanthones Conjugated with Amino Acids

Synthesis and Anti-Inflammatory Evaluation of a Library of Chiral Derivatives of Xanthones Conjugated with Proteinogenic Amino Acids

Isolation and Pharmacochemistry of  α-Mangostin as a Chemotherapeutic Agent

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A Review on the Cytotoxic and Antimicrobial Properties of Xanthones from Cratoxylum cochinchinense

Cited by 3 publications

References 46 publications

Evaluation of Antitumor Activity of Xanthones Conjugated with Amino Acids

Evaluation of Antitumor Activity of Xanthones Conjugated with Amino Acids

Synthesis and Anti-Inflammatory Evaluation of a Library of Chiral Derivatives of Xanthones Conjugated with Proteinogenic Amino Acids

Isolation and Pharmacochemistry of α-Mangostin as a Chemotherapeutic Agent

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Isolation and Pharmacochemistry of  α-Mangostin as a Chemotherapeutic Agent