Anti-angiogenic and antiproliferative properties of the lichen substances (-)-usnic acid and vulpinic acid

Koparal, Ayşe Tansu

doi:10.1515/znc-2014-4178

Cited by 59 publications

(46 citation statements)

References 29 publications

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“…For usnic acid ( 3 ) an inhibition of the migration of cultivated HUVEC was previously observed . This is consistent with our observation of its effect on 518A2 melanoma cells.…”

Section: Discussionsupporting

confidence: 92%

Antiangiogenic and Toxic Effects of Genistein, Usnic Acid, and Their Copper Complexes in Zebrafish Embryos at Different Developmental Stages

Draut

Rehm

Begemann

et al. 2017

Chemistry & Biodiversity

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Angiogenesis plays a major role in the normal embryonic development and in diseases such as cancer. Drugs that control angiogenesis are an alternative way to tackle this disease. The polyphenols usnic acid (3), genistein (5), and daidzein (6) were tested for antiangiogenic and unwanted effects in zebrafish embryos whose blood vessel system resembles that of mammals. The established tyrosine kinase inhibitors axitinib (1) and tyrphostin AG490 (2) were included for comparison. All compounds except 6 caused distinct antiangiogenic effects such as a concentration-dependent reduction of intersegmental vessels, dorsal longitudinal anastomotic vessels, subintestinal veins and secondary sprouts. As side effects, pericardial oedema and the impairment of blood flow were observed. Usnic acid (3), genistein (5) and Cu(II)-genisteinate (7) gave rise to a curvature of the spine. Compounds 5 and 7 also induced cell death in the head of the embryos at higher doses. All effects were more pronounced when the compounds had been applied at an early stage (24 hpf) rather than at 48 hpf. The copper complexes 4 and 7 showed a stronger antiangiogenic effect than the free ligands 3 and 5. The genistein complex 7 was antiangiogenic at doses so low that side effects were tolerable, and thus it may be a potential anticancer drug candidate.

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“…For usnic acid ( 3 ) an inhibition of the migration of cultivated HUVEC was previously observed . This is consistent with our observation of its effect on 518A2 melanoma cells.…”

Section: Discussionsupporting

confidence: 92%

Antiangiogenic and Toxic Effects of Genistein, Usnic Acid, and Their Copper Complexes in Zebrafish Embryos at Different Developmental Stages

Draut

Rehm

Begemann

et al. 2017

Chemistry & Biodiversity

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“…In a study by Koparal (2015), (-)-usnic acid demonstrated antiangiogenic properties by inhibiting tube formation in a time and dose dependent manner, with IC 50 427.9 and 71.5 lM after 24 and 48 h of incubation, respectively.…”

Section: Antiangiogenic Activitymentioning

confidence: 99%

Enantioselective activity of usnic acid: a comprehensive review and future perspectives

2019

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This review is focused on the comparison of the biological and pharmacological activities of usnic acid enantiomers. Most of the available data refer to (?)-usnic acid, while the left-handed isomer has been less often significantly studied. Special attention was paid to the experiments comparing both (?)-and (-)-usnic acid at the same time, the results of which indicated interesting differences, however no tendency as to which enantiomer was more potent could be observed. Nevertheless, more studies, especially on (-)-usnic acid, are needed to give a final explanation for the similarities and differences between both usnic acid enantiomers. These should be especially directed to steric structure-activity relationship of the enantiomers, tested under the same experimental conditions, which may help to explain the possible mechanisms of their actions.

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“…Vulpinic acid exhibits antibiotic activities against bacteria [13] and fungi [14]. Moreover, the anti-cancer effects of vulpinic acid have been reported, which includes anti-angiogenesis, anti-proliferative properties, and cytotoxicity to human cancer cells [15][16][17]. The protective effects of vulpinic acid against oxidative stress in endothelial cells were discovered additionally, suggesting it as a drug candidate to treat atherosclerosis [18].…”

Section: Introductionmentioning

confidence: 99%

Vulpinic Acid Controls Stem Cell Fate toward Osteogenesis and Adipogenesis

Nam

Kim

et al. 2019

Genes

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Vulpinic acid, a naturally occurring methyl ester of pulvinic acid, has been reported to exert anti-fungal, anti-cancer, and anti-oxidative effects. However, its metabolic action has not been implicated yet. Here, we show that vulpinic acid derived from a mushroom, Pulveroboletus ravenelii controls the cell fate of mesenchymal stem cells and preadipocytes by inducing the acetylation of histone H3 and α-tubulin, respectively. The treatment of 10T1/2 mesenchymal stem cells with vulpinic acid increased the expression of Wnt6, Wnt10a, and Wnt10b, which led to osteogenesis inhibiting the adipogenic lineage commitment, through the upregulation of H3 acetylation. By contrast, treatment with vulpinic acid promoted the terminal differentiation of 3T3-L1 preadipocytes into mature adipocytes. In this process, the increase in acetylated tubulin was accompanied, while acetylated H3 was not altered. As excessive generation of adipocytes occurs, the accumulation of lipid drops was not concentrated, but dispersed into a number of adipocytes. Consistently, the expressions of lipolytic genes were upregulated and inflammatory factors were downregulated in adipocytes exposed to vulpinic acid during adipogenesis. These findings reveal the multiple actions of vulpinic acid in two stages of differentiation, promoting the osteogenesis of mesenchymal stem cells and decreasing hypertrophic adipocytes, which can provide experimental evidence for the novel metabolic advantages of vulpinic acid.

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Anti-angiogenic and antiproliferative properties of the lichen substances (-)-usnic acid and vulpinic acid

Cited by 59 publications

References 29 publications

Antiangiogenic and Toxic Effects of Genistein, Usnic Acid, and Their Copper Complexes in Zebrafish Embryos at Different Developmental Stages

Antiangiogenic and Toxic Effects of Genistein, Usnic Acid, and Their Copper Complexes in Zebrafish Embryos at Different Developmental Stages

Enantioselective activity of usnic acid: a comprehensive review and future perspectives

Vulpinic Acid Controls Stem Cell Fate toward Osteogenesis and Adipogenesis

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