Hydrated Rubrolides from the New Zealand Tunicate Synoicum kuranui

Bracegirdle, Joe; Stevenson, Luke J; Sharrock, Abigail V.; Page, Michael; Vorster, Jan; Owen, Jeremy G.; Ackerley, David F.; Keyzers, Robert A.

doi:10.1021/acs.jnatprod.0c01248

Cited by 10 publications

(18 citation statements)

References 18 publications

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“…The antibacterial results reported for 5 and 7 herein are consistent with that recently reported for rubrolide A against MSSA (MIC 13.4 μM). 15 Finally, the prunolides A−C (1−3) and pityriacitrin C (11) were tested for antiplasmodial activity against the Plasmodium falciparum 3D7 strain, with prunolide C (3) displaying weak activity at IC 50 5.1 μM (SI = 7.6), while pityriacitrin C (8, IC 50 15.1 μM, SI = 2.66) was considered inactive (Table S1). All of the compounds tested against P. falciparum demonstrated minimal cytotoxic activities against a human embryonic kidney (HEK293) cell line (Table S1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…aureus strains compared with prunolide D ( 4 ) indicating that monobromination of the B-ring was more favorable than the A-ring system. The antibacterial results reported for 5 and 7 herein are consistent with that recently reported for rubrolide A against MSSA (MIC 13.4 μM) …”

Section: Resultsmentioning

confidence: 99%

“…Recently, it has been shown that plitidepsin also has potent antiviral activity against SARS-CoV-2 that is 27.5 times greater than the current standard of care antiviral treatment remdesivir and is currently undergoing phase 3 clinical trials . Ascidians, in particular those belonging to the genus Synoicum, have also been found to produce bioactive non-nitrogenous polyaromatic butenolide natural products, a structure class that includes rubrolides, − cadiolides, , procerolides, and the dimeric prunolides . The prunolides, tetraphenolic bis-spiroketal compounds containing a rare 1,6,8-trioxadispiro[4.1.4.2]trideca-3,10,12-triene-2,9-dione carbon structure, have only so far been reported from Synoicum species, , with a sample of the Australian colonial ascidian Synoicum prunum (Herdman, 1899) affording the weakly cytotoxic prunolides A–C ( 1 – 3 ) …”

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confidence: 99%

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α-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated β-Carboline Sulfamate from the Ascidian Synoicum prunum

Holland

Prebble

et al. 2022

J. Nat. Prod.

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Seven new polyaromatic bis-spiroketal-containing butenolides, the prunolides D−I (4−9) and cis-prunolide C (10), a new dibrominated β-carboline sulfamate named pityriacitrin C (11), alongside the known prunolides A−C (1−3) were isolated from the Australian colonial ascidian Synoicum prunum. The prunolides D−G (4−7) represent the first asymmetrically brominated prunolides, while cis-prunolide C ( 10) is the first reported with a cis-configuration about the prunolide's bisspiroketal core. The prunolides displayed binding activities with the Parkinson's disease-implicated amyloid protein α-synuclein in a mass spectrometry binding assay, while the prunolides (1−5 and 10) were found to significantly inhibit the aggregation (>89.0%) of α-synuclein in a ThT amyloid dye assay. The prunolides A−C (1−3) were also tested for inhibition of pSyn aggregate formation in a primary embryonic mouse midbrain dopamine neuron model with prunolide B (2) displaying statistically significant inhibitory activity at 0.5 μM. The antiplasmodial and antibacterial activities of the isolates were also examined with prunolide C (3) displaying only weak activity against the 3D7 parasite strain of Plasmodium falciparum. Our findings reported herein suggest that the prunolides could provide a novel scaffold for the exploration of future therapeutics aimed at inhibiting amyloid protein aggregation and the treatment of numerous neurodegenerative diseases.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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α-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated β-Carboline Sulfamate from the Ascidian Synoicum prunum

Holland

Prebble

et al. 2022

J. Nat. Prod.

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“…Over 5,000 halogenated natural products had been reported as of 2011 with structural and functional diversity ( Gribble, 2015 ; Zeng and Zhan, 2019 ). As a key part of halogenated molecules, chlorinated compounds have demonstrated a broad range of remarkable activities ( Gribble, 2015 ), including antibacterial activity ( Bracegirdle et al, 2021 ; Saetang et al, 2021 ) and anticancer activity ( Luo et al, 2018 ). Recently, three new natural chlorinated 3-phenylpropanoic acid derivatives were found with significant and selective inhibitory activities toward Escherichia coli and Staphylococcus aureus ( Shaala et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory compounds from the mangrove endophytic fungus Amorosia sp. SCSIO 41026

Ren

Chen

et al. 2022

Front. Microbiol.

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Three new chlorinated compounds, including two propenylphenol derivatives, chlorophenol A and B (1 and 2), and one benzofuran derivative, chlorophenol C (3), together with 16 known compounds, were isolated from the mangrove endophytic fungus Amorosia sp. SCSIO 41026. 7-Chloro-3,4-dihydro-6,8-dihydroxy-3-methylisocoumarine (4) and 2,4-dichloro-3-hydroxy-5-methoxy-toluene (5) were obtained as new natural products. Their structures were elucidated by physicochemical properties and extensive spectroscopic analysis. Compounds 1, 4, 7, 9, 13, 15, 16, and 19 possessed inhibitory effects against the excessive production of nitric oxide (NO) and pro-inflammatory cytokines in lipopolysaccharide (LPS)-challenged RAW264.7 macrophages without obvious cytotoxicity. Moreover, 5-chloro-6-hydroxymellein (13) further alleviated the pathological lung injury of LPS-administrated mice and protected RAW264.7 macrophages against LPS-induced inflammation through PI3K/AKT pathway in vivo. Our research laid the foundation for the application of compound 13 as a potential anti-inflammatory candidate.

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“…The natural products laboratory has been successful in finding new compounds from marine organisms. [17][18][19][20][21][22][23][24][25] The ocean makes up 70% of the Earth's surface and contributes some of the most diverse and complex ecosystems in the world. 26 With only 20% of the ocean floor mapped 27 and already a rich diversity of unique organisms known within the ocean, 28 it stands to reason that there are thousands more organisms or entire classes potentially even phylum yet to be discovered.…”

Section: Marine Natural Productsmentioning

confidence: 99%

The Feasibility of Establishing a Morphological Cell Profiling Assay to Assess the Bioactivity of Natural Products

Taylor¹

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Morphological cell profiling (MCP) is an assay which quantifies the morphology of cells and cellular components. Changes in the morphology of cells following compound treatment has been shown to assess the bioactivity, and even propose a target of said compound. It is a powerful assay that can be used to assess novel compounds for drug candidature. However, it is currently not transferable between institutions. Thus, this project evaluated the feasibility of establishing an MCP assay at Victoria University of Wellington - Te Herenga Waka to assess the bioactivity of novel natural products from the natural products laboratory. First, a new individualistic approach to select compound concentration for MCP was assessed by flow cytometry with six exemplary drugs. Results concluded this flow cytometry approach can realise an ideal concentration for individual compounds in which the compound treatment was bioactive but not cytotoxic. This approach provides more biologically relevant and accurate information about a compound's bioactivity than previous MCP methods. Second, the feasibility of establishing the assay was assessed by testing the same six drugs through protocol common to MCP assays. Various stains and microscopes were tested for suitability for an MCP; image quantitative software CellProfiler was evaluated for MCP analysis ease; and quality control protocol was attempted. Ultimately, an MCP is currently not feasible at Te Herenga Waka as multiple components to establish the assay are too difficult and time intensive to complete. Third, discorhabdin E, a pyrroloiminoquinone alkaloid, was isolated from the New Zealand marine sponge, Latrunculia kaakaariki. The compound was tested as if it were a novel natural product compound through the new flow cytometry concentration selection protocol to test its effectivity, and was subsequently assessed by morphological analysis.

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Hydrated Rubrolides from the New Zealand Tunicate Synoicum kuranui

Cited by 10 publications

References 18 publications

α-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated β-Carboline Sulfamate from the Ascidian Synoicum prunum

α-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated β-Carboline Sulfamate from the Ascidian Synoicum prunum

Anti-inflammatory compounds from the mangrove endophytic fungus Amorosia sp. SCSIO 41026

The Feasibility of Establishing a Morphological Cell Profiling Assay to Assess the Bioactivity of Natural Products

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