Development of ergosterol peroxide probes for cellular localisation studies

Ling, Taotao; Lang, Walter H.; Martínez-Montemayor, Michelle M.; Rivas, Fátima

doi:10.1039/c9ob00145j

Cited by 24 publications

(16 citation statements)

References 35 publications

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“…A more rigorous report guided by the principle that a set of negative controls was required to conduct washout experiments of the EP probe, and orthogonal fluorescent chromophores had to be synthesized for live cell studies. 69 Also, the cell lines with fluorescently-tagged organelle were generated to compliment the use of organelle trackers. The hydroxyl group at C-3 of the EP was the direct coupling site for the biotin and chromophores to avoid any further chemical modification of the EP that could interfere with its naive action (compounds 11d – g , Figure 10 ).…”

Section: Triterpenoid Chemical Probesmentioning

confidence: 99%

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Ling¹,

Boyd²,

Rivas³

2022

Chem. Res. Toxicol.

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The triterpenoid natural products have played an important role in understanding mechanistic models of human diseases. These natural products are diverse, but many have been characterized as reactive oxygen species (ROS) modulators. ROS can regulate cell survival and function, which ultimately affects biological processes leading to disease. The triterpenoids offer an untapped source of creativity to generate tool compounds with high selectivity to regulate ROS. This brief Review highlights the diverse complexity by which these secondary metabolites induce many cell death modalities (apoptosis, autophagy, ferroptosis, etc.) that can affect various complex cell signaling pathways through ROS and ultimately lead to evading or accelerating cell death.

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Section: Triterpenoid Chemical Probesmentioning

confidence: 99%

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Ling¹,

Boyd²,

Rivas³

2022

Chem. Res. Toxicol.

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“…Moreover, fourteen known compounds, including eight triterpenoids, hexagonin F ( 3 ) [ 30 ], sinensoic acid ( 4 ) [ 31 ], 24( E )-3 β -hydroxylanosta-8,24-dien-26-al-21-oic acid ( 5 ) [ 32 ], trametenolic acid ( 6 ) [ 33 ], eburicoic acid ( 7 ) [ 34 ], 24-methylenelanost-8-en-3-ol ( 8 ) [ 35 ], eburicodiol ( 9 ) [ 36 ], and gloeophyllin B ( 10 ) [ 37 ]; four steroids, ergosterol peroxide ( 11 ) [ 38 ], ergosterol ( 12 ) [ 39 ], (22 E )-ergosta-7,22-dien-3 β -ol ( 13 ) [ 40 ], and (22 E ,24 R )-5-hydroxy-5 α -ergosta-7,22-diene-3,6-dione ( 14 ) [ 41 ]; and two isocoumarins, oospoglycol ( 15 ) [ 42 ] and oospolactone ( 16 ) [ 43 ], were identified. In addition, eleven known constituents, including one triterpenoid, lupeol ( 17 ) [ 44 ]; seven steroids, ergosterol peroxide ( 11 ), (22 E )-ergosta-7,22-dien-3 β -ol ( 13 ), (22 E ,24 R )-5-hydroxy-5 α -ergosta-7,22-diene-3,6-dione ( 14 ), 9,11-dehydroergosterol peroxide ( 18 ) [ 45 ], 5,8-epidioxy-(5 α ,8 α ,22 E )-ergosta-6,22-dien-3-one ( 19 ) [ 46 ], ergosta-7,22-diene-3-one ( 20 ) [ 40 ], and stigmast-4-en-3-one ( 21 ) [ 47 ]; and three benzenoids, syringic acid ( 22 ) [ 48 ], isovanillic acid ( 23 ) [ 49 ], and tyrosol ( 24 ) [ 50 ], were characterized from the fruiting bodies of T. suaveolens . The known compounds were identified by comparison of their physical and spectroscopic data with those previously published.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 14 was reported to attenuate the growth and triggered an apoptotic process in prostate cancer cells [ 55 ]. Inhibition of various tumor cell lines by compound 19 was also determined [ 46 ]. Based on our anti-inflammatory examination results and reported bioactivities in the literature, it can be concluded that the fruiting bodies of T. cubensis and T. suaveolens could be promising as anti-inflammatory lead drugs or natural, healthy ingredients.…”

Section: Resultsmentioning

confidence: 99%

Constituents from the Fruiting Bodies of Trametes cubensis and Trametes suaveolens in Vietnam and Their Anti-Inflammatory Bioactivity

Ngân

Cheng³

et al. 2021

Molecules

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It is reported that various fungi have been used for medicine and edible foods. The tropical Trametes genus is popular and well-known in Vietnam for its health effects and bioactivities. In this study, the fruiting bodies of the edible fungi T. cubensis and T. suaveolens were collected in Vietnam. The preliminary bioactivity screening data indicated that the methanol extracts of the fruiting bodies of T. cubensis and T. suaveolens displayed significant inhibition of superoxide anion generation and elastase release in human neutrophils. Therefore, the isolation and characterization were performed on these two species by a combination of chromatographic methods and spectrometric analysis. In total, twenty-four compounds were identified, and among these (1–3) were characterized by 1D-, 2D-NMR, and HRMS analytical data. In addition, the anti-inflammatory potentials of some purified compounds were examined by the cellular model for the inhibition of superoxide anion generation and elastase release in human neutrophils. Among the isolated compounds, (5,14), and (19) displayed significant anti-inflammatory potential. As the results suggest, the extracts and isolated compounds from T. cubensis and T. suaveolens are potential candidates for the further development of new anti-inflammatory lead drugs or natural healthy foods.

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“…A series of EP analogs containing BODIPY or a biotin moiety was obtained by Rivas et al as probes for cellular localization studies [ 149 ]. They demonstrated that EP is distributed across the cytosol with significant accumulation in the endoplasmic reticulum.…”

Section: Endoperoxidesmentioning

confidence: 99%

Structure and Biological Activity of Ergostane-Type Steroids from Fungi

2022

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Mushrooms are known not only for their taste but also for beneficial effects on health attributed to plethora of constituents. All mushrooms belong to the kingdom of fungi, which also includes yeasts and molds. Each year, hundreds of new metabolites of the main fungal sterol, ergosterol, are isolated from fungal sources. As a rule, further testing is carried out for their biological effects, and many of the isolated compounds exhibit one or another activity. This study aims to review recent literature (mainly over the past 10 years, selected older works are discussed for consistency purposes) on the structures and bioactivities of fungal metabolites of ergosterol. The review is not exhaustive in its coverage of structures found in fungi. Rather, it focuses solely on discussing compounds that have shown some biological activity with potential pharmacological utility.

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Development of ergosterol peroxide probes for cellular localisation studies

Abstract: Cell-permeable ergosterol peroxide probes were synthesized to advance their biological understanding and therapeutic potential.

Cited by 24 publications

References 35 publications

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

Constituents from the Fruiting Bodies of Trametes cubensis and Trametes suaveolens in Vietnam and Their Anti-Inflammatory Bioactivity

Structure and Biological Activity of Ergostane-Type Steroids from Fungi

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