Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities

Loureiro, Daniela R. P.; Magalhães, Álvaro F.; Soares, José X.; Pinto, José Cardoso; Azevedo, Carlos Lima; Vieira, Sara F.; Henriques, Ana C.; Ferreira, Helena; Neves, Nuno M.; Bousbaa, Hassan; Reis, Salette; Afonso, Carlos; Pinto, Madalena

doi:10.1002/cmdc.201900735

Cited by 12 publications

(16 citation statements)

References 38 publications

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“…Total synthesis of xanthone derivatives has been reported due to the trace isolation yield of certain xanthones from natural sources. The total synthesis of termicalcicolanone A, α-mangostin, and mangiferin has been reported recently [90][91][92][93].…”

Section: Synthesis Of Xanthone Derivativesmentioning

confidence: 99%

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

et al. 2021

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The annual number of cancer deaths continues increasing every day; thus, it is urgent to search for and find active, selective, and efficient anticancer drugs as soon as possible. Among the available anticancer drugs, almost all of them contain heterocyclic moiety in their chemical structure. Xanthone is a heterocyclic compound with a dibenzo-γ-pyrone framework and well-known to have “privileged structures” for anticancer activities against several cancer cell lines. The wide anticancer activity of xanthones is produced by caspase activation, RNA binding, DNA cross-linking, as well as P-gp, kinase, aromatase, and topoisomerase inhibition. This anticancer activity depends on the type, number, and position of the attached functional groups in the xanthone skeleton. This review discusses the recent advances in the anticancer activity of xanthone derivatives, both from natural products isolation and synthesis methods, as the anticancer agent through in vitro, in vivo, and clinical assays.

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Section: Synthesis Of Xanthone Derivativesmentioning

confidence: 99%

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

et al. 2021

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“…To complement the information disclosed, the pharmacokinetic parameters were evaluated in this document using the SWISSADME platform [59]. Based on the analyses of Table 1, it may be concluded that more than half of the isolated marine compounds (1-6, 9, 20-22, 29-41, 43-46) follow Lipinski rules [60], but only ten (5,27,29,38,40,41,(43)(44)(45)(46) are predicted to have high BBB permeability.…”

Section: Adme Propertiesmentioning

confidence: 99%

“…Based on the analyses of Table 1 , it may be concluded that more than half of the isolated marine compounds ( 1 – 6 , 9 , 20 – 22 , 29 – 41 , 43 – 46 ) follow Lipinski rules [ 60 ], but only ten ( 5 , 27 , 29 , 38 , 40 , 41 , 43 – 46 ) are predicted to have high BBB permeability.…”

Section: Adme Propertiesmentioning

confidence: 99%

Small Molecules of Marine Origin as Potential Anti-Glioma Agents

et al. 2021

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Marine organisms are able to produce a plethora of small molecules with novel chemical structures and potent biological properties, being a fertile source for discovery of pharmacologically active compounds, already with several marine-derived agents approved as drugs. Glioma is classified by the WHO as the most common and aggressive form of tumor on CNS. Currently, Temozolomide is the only chemotherapeutic option approved by the FDA even though having some limitations. This review presents, for the first time, a comprehensive overview of marine compounds described as anti-glioma agents in the last decade. Nearly fifty compounds were compiled in this document and organized accordingly to their marine sources. Highlights on the mechanism of action and ADME properties were included. Some of these marine compounds could be promising leads for the discovery of new therapeutic alternatives for glioma treatment.

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“…These xanthones are usually highly substituted, with different substituent patterns being the substituents found to be essential for four types; hydroxy, methoxy, methyl, and methoxycarbonyl groups. It seems that the methoxy group is not common in bioactive marine xanthones [ 50 ], but yicathins B ( 3 ) and C ( 4 ) ( Figure 2 ), which were recently prepared by total synthesis [ 51 ], present such a group at C-8. Other examples include xanthones bearing a 6-methoxy group ( 2 ) and ( 6 ) and 7-methoxy group ( 13 ) and ( 15 ) ( Figure 2 ).…”

Section: New Marine Xanthones Isolated Since 2010mentioning

confidence: 99%

Marine-Derived Xanthone from 2010 to 2021: Isolation, Bioactivities and Total Synthesis

2022

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Marine life has proved to be an invaluable source of new compounds with significant bioactivities, such as xanthones. This review summarizes the advances made in the study of marine-derived xanthones from 2010 to 2021, from isolation towards synthesis, highlighting their biological activities. Most of these compounds were isolated from marine-derived fungi, found in marine sediments, and associated with other aquatic organisms (sponge and jellyfish). Once isolated, xanthones have been assessed for different bioactivities, such as antibacterial, antifungal, and cytotoxic properties. In the latter case, promising results have been demonstrated. Considering the significant bioactivities showed by xanthones, efforts have been made to synthesize these compounds, like yicathins B and C and the secalonic acid D, through total synthesis.

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Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 12 publications

References 38 publications

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

Small Molecules of Marine Origin as Potential Anti-Glioma Agents

Marine-Derived Xanthone from 2010 to 2021: Isolation, Bioactivities and Total Synthesis

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