Perezone, from the gorgonian Pseudopterogorgia rigida, induces oxidative stress in human leukemia cells

Abreu, Paula Alvarez; Wilke, Diego Veras; Araújo, Ana Jérsia; Filho, José Delano Barreto Marinho; Ferreira, Elthon G.; Ribeiro, Carlos Margo R.; Pinheiro, Leandro S.; Amorim, Juliana W.; Valverde, Alessandra L.; Epifanio, Rosângela de A.; Costa-Lotufo, Letı́cia V.; Jimenez, Paula Christine

doi:10.1016/j.bjp.2015.07.020

Cited by 10 publications

(4 citation statements)

References 31 publications

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“…Recent studies have shown that 1 exhibited moderate cytotoxicity (8.2-32.2 µM) against several tumor cell lines. The effect was partially associated to the production of ROS [28]. These results prompted us to assay the potential acute toxicity effects of 1 using the Lorke protocol.…”

Section: Resultsmentioning

confidence: 99%

Antidiabetic and Antihyperalgesic Effects of a Decoction and Compounds from Acourtia thurberi

et al. 2016

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The purpose of this research was to examine the preclinical efficacy of a decoction from the roots of as a hypoglycemic, antihyperglycemic, and antihyperalgesic agent using well-known experimental models in mice. Acute oral administration of decoction did not produce toxic effects in mice, according to the Lorke procedure. decoction (31.6-316.2 mg/kg, p. o.) decreased blood glucose levels during acute hypoglycemic and the oral glucose tolerance and oral sucrose tolerance tests, both in normoglycemic and hyperglycemic animals. Phytochemical analysis of roots led to the isolation of perezone (), a mixture of -pipitzol () and -pipitzol (), and 8--D-glucopyranosyloxy-4-methoxy-5-methyl-coumarin (). A pharmacological evaluation of compounds - (3.2-31.6 mg/kg) using the same assays revealed their hypoglycemic and antihyperglycemic actions. Finally, local administration of decoction (31.6-316.2 µg/paw) and compounds- (3.2-31.6 µg/paw) produced significant inhibition on the licking time during the formalin test in healthy and hyperglycemic mice, demonstrating their antinociceptive and antihyperalgesic potential, respectively. Altogether, these results could be related to the use of for treating diabetes and painful complaints in contemporary Mexican folk medicine. A suitable UPLC-ESI/MS method was developed and successfully applied to quantify simultaneously compounds and in decoction.

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Section: Resultsmentioning

confidence: 99%

Antidiabetic and Antihyperalgesic Effects of a Decoction and Compounds from Acourtia thurberi

et al. 2016

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“…Natural products containing the 1,4-benzoquinone scaffold exhibit a wide range of biological activities. [1][2][3][4][5] Examples of this class of molecules are shown in Figure 1. 2-Methyl-5-(3-methyl-2-butenyl)-1,4-benzoquinone, 1 is a natural product first isolated by Burnett et al in 1968 from the leaves of Pyrola media.…”

Section: Introductionmentioning

confidence: 99%

“…[4] Lastly, the benzoquinone (-)-perezone 5, found in Pseudopterogorgia rigida, has shown promising cytotoxicity toward human tumor cell lines. [5] In light of the interesting biological properties of 1,4benzoquinone containing natural products, easy access via a straight and efficient synthesis is needed. We had recently reported on the concise synthesis of primin 4.…”

Section: Introductionmentioning

confidence: 99%

Concise Synthesis of 1,4‐Benzoquinone‐Based Natural Products as Mitochondrial Complex I Substrates and Substrate‐Based Inhibitors

et al. 2020

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A short, efficient one‐step synthesis of 2‐methyl‐5‐(3‐methyl‐2‐butenyl)‐1,4‐benzoquinone, a natural product from Pyrola media is described. The synthesis is based on a direct late C−H functionalization of the quinone scaffold. The formation of the natural product was confirmed by means of 2D‐NMR spectroscopy. Additional derivatives were synthesized and tested alongside the natural product as potential substrate and substrate‐based inhibitors of mitochondrial complex I (MCI). The structure‐activity relationship study led to the discovery of 3‐methylbuteneoxide‐1,4‐anthraquinone (1 i), an inhibitor with an IC50 of 5 μM against MCI. The identified molecule showed high selectivity for MCI when tested against other quinone‐converting enzymes, including succinate dehydrogenase, and the Na (+)‐translocating NADH:quinone oxidoreductase. Moreover, the identified inhibitor was also active in cell‐based proliferation assays. Therefore, 1 i can be considered as a novel chemical probe for MCI.

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“…For instance, Lobophytum michaelae (Taiwan), Cladiella sp. (Indonesia), Dichotella gemmacea (China) and Antillogorgia rigida (Bahamas) have yielded compounds with high cytotoxic activity against different cell lines such as P388 (mouse lymphoma), HT-29 (colorectal adenocarcinoma), DLD-1 (colorectal adenocarcinoma), HeLa (cervix carcinoma), MCF-7 (breast adenocarcinoma), A549 (lung carcinoma) and Daoy (medulloblastoma), among others [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

New Diterpenes Isolated from the Colombian Caribbean Soft Coral Pseudoplexaura flagellosa and Their Cytotoxic Properties

Estrada¹,

Puyana²,

Castellanos³

et al. 2019

Rec.Nat.Prod.

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Studies about secondary metabolites isolated from soft corals around the world have proven the potential of these organism as producers of compounds with a potent cytotoxic activity. In this work, we obtained the extract of Pseudoplexaura flagellosa collected in Santa Marta, Colombia, the cytotoxic activity of this extract, fractions and compounds was established against SiHa (ATCC® HTB-35™), MDA-MB-231 (ATCC® HTB26™), A549 (ATCC® CRM-CCL-185™), PC3 (ATCC® CRL1435), and L929 (ATCC® CCL1™) cell lines. The results showed that the extract of soft coral P. flagellosa has cytotoxic activity with an IC50 of 35.4, 72.3, 49.8 and 40.5 μg/mL against SiHa, A549, PC3 and MDA-MB-231 cell lines, respectively. Thus, this extract was repeatedly subjected to different chromatographic columns and final purification of these fractions afforded pure compounds 1 -4, which were elucidated by 1D and 2D NMR experiments including 1 H, 13 C, COSY, HSQC, HMBC and NOESY, and HRESIMS. In addition, Mosher method was used to establish the stereochemistry of compound 2 and chemical interconversion allow establishing the stereochemistry of compound 1. These results let to conclude that compound 2 is a new stereoisomers of acetylated asperdiol previously reported on literature. Additionally, three analogues 5, 6, and 7 were synthesized from compound 1 and the cytotoxic activity of all compounds was evaluated using doxorubicin as positive control. The results showed that 6 (IC50 of 19.3, 23.7, 13.4 and 18.7 μg/mL against SiHa, A549, PC3 and MDA-MB-231, respectively) was the most active compound against all the cancer cell lines.

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Perezone, from the gorgonian Pseudopterogorgia rigida, induces oxidative stress in human leukemia cells

Cited by 10 publications

References 31 publications

Antidiabetic and Antihyperalgesic Effects of a Decoction and Compounds from Acourtia thurberi

Antidiabetic and Antihyperalgesic Effects of a Decoction and Compounds from Acourtia thurberi

Concise Synthesis of 1,4‐Benzoquinone‐Based Natural Products as Mitochondrial Complex I Substrates and Substrate‐Based Inhibitors

New Diterpenes Isolated from the Colombian Caribbean Soft Coral Pseudoplexaura flagellosa and Their Cytotoxic Properties

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