Cytotoxic meroterpenoids from the macroalga Cystoseira abies-marina

Gouveia, Vera; Seca, Ana M. L.; Barreto, Maria Carmo; Neto, Ana I.; Kijjoa, Anake; Silva, Artur M. S.

doi:10.1016/j.phytol.2013.07.012

Cited by 27 publications

(19 citation statements)

References 15 publications

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“…Phytochemical studies have revealed that species belonging to this genus are rich in phlorotannins, sterols, meroditerpenoids and sesquiterpenoids (Amico, 1995;Moreno et al, 1998;Khanavi et al, 2012;Sathya et al, 2013;Montero et al, 2014), some of which exhibiting antioxidant, antitumoral, antifouling and/or antimicrobial activities with potential applications in the pharmaceutical industry (Amico, 1995;Gouveia et al, 2013;Valls and Piovetti, 1995).…”

Section: Introductionmentioning

confidence: 99%

Can macroalgae provide promising anti-tumoral compounds? A closer look at Cystoseira tamariscifolia as a source for antioxidant and anti-hepatocarcinoma compounds

Vizetto‐Duarte

Custódio

Acosta

et al. 2015

Preprint

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Marine organisms are a prolific source of drug leads in a variety of therapeutic areas. In the last few years, biomedical, pharmaceutical and nutraceutical industries have shown growing interest in novel compounds from marine organisms, including macroalgae. Cystoseira is a genus of Phaeophyceae (Fucales) macroalgae known to contain bioactive compounds. Organic extracts (hexane, diethyl ether, ethyl acetate and methanol extracts) from three Cystoseira species (C. humilis, C. tamariscifolia and C. usneoides) were evaluated for their total phenolic content, radical scavenging activity against DPPH and ABTS radicals, and antiproliferative activity against a human hepatocarcinoma cell line (HepG2 cells). C. tamariscifolia had the highest TPC and RSA. The hexane extract of C. tamariscifolia (CTH) had the highest cytotoxic activity (IC50=2.31 µg/mL), and was further tested in four human tumor (cervical adenocarcinoma HeLa; gastric adenocarcinoma AGS; colorectal adenocarcinoma HCT-15; neuroblastoma SH-SY5Y), and two non-tumor (murine bone marrow stroma S17 and human umbilical vein endothelial HUVEC) cell lines in order to determine its selectivity. CTH strongly reduced viability of all tumor cell lines, especially of HepG2 cells. Cytotoxicity was particularly selective for the latter cells with a selectivity index = 12.6 as compared to non-tumor cells. Incubation with CTH led to a 2-fold decrease of HepG2 cell proliferation as shown by the BrdU incorporation assay. CTH-treated HepG2 cells presented also pro-apoptotic features, such as increased Annexin V/PI binding and dose-dependent morphological alterations in DAPI-stained cells. Moreover, it had a noticeable disaggregating effect on 3D multicellular tumor spheroids. Demethoxy cystoketal chromane, a derivative of the meroditerpenoid cystoketal, was identified as the active compound in CTH and was shown to display selective in vitro cytotoxicity towards HepG2 cells.

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Section: Introductionmentioning

confidence: 99%

Can macroalgae provide promising anti-tumoral compounds? A closer look at Cystoseira tamariscifolia as a source for antioxidant and anti-hepatocarcinoma compounds

Vizetto‐Duarte

Custódio

Acosta

et al. 2015

Preprint

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“…In the present work, we report examples of molecules which illustrate these investigations.Concerning plants such as Juniperus brevifolia, an Azorean endemic conifer, we isolated dehydroabietinol, which was active against human tumor cell lines MCF7, A549 and especially against HeLa (IC50 = 15.7 μM, with a selectivity index SI = IC50Vero/IC50HeLa of 1.78) [1].From seaweed Cystoseira abies-marina, two new meroditerpenes, cystoazorols A and B, were isolated. Cystoazorol A exhibited the highest growth inhibition against HeLa cells (21.6 and 5.9 μM in lag and log growth phases, respectively), with an SI higher than taxol, the positive control [2].Finally, we report the antitumor activity of chalcones obtained by chemical synthesis. Among the different compounds synthesized, the best results against A549 cell line were IC50 values of 367.4 and 311.4 μM for a chalcone and a flavanone, respectively.…”

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confidence: 82%

“…From seaweed Cystoseira abies-marina, two new meroditerpenes, cystoazorols A and B, were isolated. Cystoazorol A exhibited the highest growth inhibition against HeLa cells (21.6 and 5.9 μM in lag and log growth phases, respectively), with an SI higher than taxol, the positive control [2].…”

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confidence: 92%

Searching for Molecules against Cancer in the Azores: Plants, Macroalgae, and Synthetic Compounds

Barreto

Gouveia

Rosa

et al. 2019

The 2nd Molecules Medicinal Chemistry Symposium (MMCS): Facing Novel Challenges in Drug Discovery

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“…However, only a few of these compounds have been investigated for their biomedical properties, such as antioxidant, antibacterial, or cytotoxic activities [14]. Regarding the antitumor activity, the most recent reports have described the capacity of the meroterpenes cystoazorol A and cystoazorones A and B, isolated from Cystoseira abies-marina, to inhibit the growth of HeLa cells [17] and the cytotoxicity of cystoketal, obtained from Cystoseira tamariscifolia, towards HepG2 cells [18].…”

Section: Introductionmentioning

confidence: 99%

Anticancer Activities of Meroterpenoids Isolated from the Brown Alga Cystoseira usneoides against the Human Colon Cancer Cells HT-29

Zbakh

Zubı́a

Reyes

et al. 2020

Foods

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Colorectal cancer (CRC) is one of the most common types of cancers and a leading cause of cancer death worldwide. The current treatment for CRC mainly involves surgery, radiotherapy, and chemotherapy. However, due to the side effects and the emergence of drug resistance, the search for new anticancer agents, pharmacologically safe and effective, is needed. In the present study, we have investigated the anticancer effects of eight algal meroterpenoids (AMTs, 1-8) isolated from the brown seaweed Cystoseira usneoides and their underlying mechanisms of action using HT-29, a highly metastatic human colon cancer cell line. All the tested meroterpenoids inhibited the growth of HT-29 malignant cells and were less toxic towards non-cancer colon cells, with the AMTs 1 and 5 exhibiting selectivity indexes of 5.26 and 5.23, respectively. Treatment of HT-29 cells with the AMTs 1, 2, 3, 4, 5, and 7 induced cell cycle arrest in G2/M phase and, in some instances, apoptosis (compounds 2, 3, and 5). Compounds 1-8 also exhibited significant inhibitory effects on the migration and/or invasion of colon cancer cells. Mechanistic analysis demonstrated that the AMTs 1, 2, 5, 6, 7, and 8 reduced phosphorylation levels of extracellular signal-regulated kinase (ERK) and the AMTs 2, 3, 4, 5, 7, and 8 decreased phosphorylation of c-JUN N-terminal kinase (JNK). Moreover, the AMTs 1, 2, 3, 4, 7, and 8 inhibited phosphorylation levels of protein kinase B (AKT) in colon carcinoma cells. These results provide new insights into the mechanisms and functions of the meroterpenoids of C. usneoides, which exhibit an anticancer effect on HT-29 colon cancer cells by inducing cell cycle arrest and apoptosis via the downregulation of ERK/JNK/AKT signaling pathways.

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Cytotoxic meroterpenoids from the macroalga Cystoseira abies-marina

Cited by 27 publications

References 15 publications

Can macroalgae provide promising anti-tumoral compounds? A closer look at Cystoseira tamariscifolia as a source for antioxidant and anti-hepatocarcinoma compounds

Can macroalgae provide promising anti-tumoral compounds? A closer look at Cystoseira tamariscifolia as a source for antioxidant and anti-hepatocarcinoma compounds

Searching for Molecules against Cancer in the Azores: Plants, Macroalgae, and Synthetic Compounds

Anticancer Activities of Meroterpenoids Isolated from the Brown Alga Cystoseira usneoides against the Human Colon Cancer Cells HT-29

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