Synthesis of stentorin

Cameron, Donald W.; Riches, Andrew G.

doi:10.1016/0040-4039(95)00248-b

Cited by 25 publications

(15 citation statements)

References 8 publications

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“…Hypericin and related monocarboxylic acid ( 3 ) have also been found in insects [ 45 ]. Similar octahydroxylated compounds have been described for protozoa (stentorin, 4 , from Stentor coeruleus ) [ 46 , 47 ] and fossil sea lily (fringelite D, 5 , from Apiocrinus sp.) [ 48 , 49 ].…”

Section: Hypericin and Related Compoundssupporting

confidence: 60%

Photosensitizing Antivirals

et al. 2021

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Antiviral action of various photosensitizers is already summarized in several comprehensive reviews, and various mechanisms have been proposed for it. However, a critical consideration of the matter of the area is complicated, since the exact mechanisms are very difficult to explore and clarify, and most publications are of an empirical and “phenomenological” nature, reporting a dependence of the antiviral action on illumination, or a correlation of activity with the photophysical properties of the substances. Of particular interest is substance-assisted photogeneration of highly reactive singlet oxygen (1O2). The damaging action of 1O2 on the lipids of the viral envelope can probably lead to a loss of the ability of the lipid bilayer of enveloped viruses to fuse with the lipid membrane of the host cell. Thus, lipid bilayer-affine 1O2 photosensitizers have prospects as broad-spectrum antivirals against enveloped viruses. In this short review, we want to point out the main types of antiviral photosensitizers with potential affinity to the lipid bilayer and summarize the data on new compounds over the past three years. Further understanding of the data in the field will spur a targeted search for substances with antiviral activity against enveloped viruses among photosensitizers able to bind to the lipid membranes.

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Section: Hypericin and Related Compoundssupporting

confidence: 60%

Photosensitizing Antivirals

et al. 2021

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“…These substances include keronopsin isolated from Pseudokeronopsis rubra Ehrenberg, 1836 (Höfle et al 1994), euplotins (Dini et al 1993;Guella et al 1994), raikovenal (Guella et al 1995;Rosini et al 1998) and epoxyfocardin (Guella et al 1996) from Euplotes species, blepharismin from Blepharisma japonicum Suzuki, 1954(Gioffrè et al 1993Checcucci et al 1997), stentorin from Stentor coeruleus Ehrenberg, 1830 (Tao et al 1993;Cameron et al 1995), spirostomin from Spirostomum teres Claparede et Lachmann, 1858(Sera et al 2006, maristentorin from Maristentor dinoferus Lobban et al, 2002(Mukherjiee et al 2006, climacostol from Climacostomum virens Ehrenberg, 1833 (Miyake et al 2003), and monoprenyl-hydroquinone from Spirostomum ambiguum Ehrenberg, 1835 (Buonanno et al 2012). Interestingly, due to its antimicrobial and pro-apoptotic activity in some tumor cell lines, the sesquiterpenoid euplotin C was recently proposed for the design of new drugs (Savoia et al 2004;Cervia et al 2006Cervia et al , 2007.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

et al. 2012

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Climacostol is a defense toxin produced by the ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that shows antimicrobial, antiparasitic, and cytotoxic activities. In this study we investigate the antimicrobial activity of climacostol and its alkyl and alkynyl derivatives against a panel of bacterial and fungal pathogens. Our results show a good and comparable antimicrobial activity of the three compounds, which have resulted effective against Gram-positive bacteria and Candida with MIC and MBC ranging from 8 to 32 mg L −1 , whereas no significant effect against Gram-negative species has been observed. Taken as a whole, the experimental data reported in the current study suggest that differences in the saturation rate of the lateral chain of climacostol are not related to the activity of the molecule. Therefore, it is likely that the general structure of the two moieties, i.e., the di-hydroxy-phenyl group and the alkenyl chains, contributes to the overall antibiotic behaviour.

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“…Since the toxins contained in the extrusomes of C. virens and S. coeruleus have been identified as "climacostol", i. e., 5-(Z)-non-2-enyl-benzene-l,3-diol (Masaki et al, 1999(Masaki et al, , 2004, and "stentorin", i. e., 2,2',4,4',5,5',7,7'-octahydroxy-3,3'-diisopropylnaphthodianthrone (Tao et al, 1993;Cameron & Riches, 1995;Iio et al, 1995), respectively, and their synthetic preparations were available from Dr. H. Iio (Department of Material Science, Osaka City University), it was directly assessed to which extent S. sphagnetorum is resistant to these toxins. The climacostol and stentorin preparations (maintained dissolved in ethanol and stored in the dark at -20 °C) were used after serial dilutions with SMB and their activities on S. sphagnetorum were measured as median lethal concentrations (LC 50 ) essentially according to the procedure described by Harumoto et al (1998) except that the effect was monitored after 1 h instead of 1 d. As shown in Figure 1, the LC 50 value was measured to be more than 100 pg/ml in the case of stentorin, and to be 10.65 pg/ml in the case of climacostol.…”

Section: Insensitivity Of S Sphagnetorum To Extrusomal Toxins Ofc Vmentioning

confidence: 99%

“…This extrusome feature has for long been reputed to be indicative that a primary function of the major extrusome molecules was related with photoreception. However the isolation and the chemically characterization of some of these molecules from pigmented extrusomes (also known as pigmentocysts) of B. japonicum (Gioffre et al, 1993;Checcucci et al, 1997) and S. coeruleus (Tao et al, 1993;Cameron & Riches, 1995), and from colourless extrusomes of Climacostomum virens (Masaki et al, 1999(Masaki et al, , 2004 and Spirostomum teres (Iio et al, 2004, Abstract in 46 th Symp. Chem.…”

Section: Introductionmentioning

confidence: 99%

Variations in the efficiency of ciliate extrusomal toxins against a common ciliate predator, the catenulidStenostomum Sphagnetorum

Buonanno¹

2005

Italian Journal of Zoology

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Species of ciliates are able to defend against predators by discharging toxins contained in their extrusomes (cortical extrusive organelles). This chemical defence was comparatively investigated in four species of ciliates, i.e., Climacostomum virens, Loxodes striatus, Spirostomum teres, and Stentor coeruleus against their common predator, i.e., the turbellarian Stenostomum sphagnetorum. The results showed that S. sphagnetorum ingests wild-type specimens of all the four ciliate species. However, the wild-type specimens of L. striatus and S. teres were immediately regurgitated apparently unharmed by S. sphagnetorum, while specimens artificially deprived of their extrusomes were normally eaten and ingested. In addition to reinforcing previous evidence that ciliates rely on extrusomal toxins for defence against their natural predators, these results were taken as a general indication that a successful defence of ciliates against their predators depends also on a different sensitivity of the predator to their extrusomal toxins.

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Synthesis of stentorin

Cited by 25 publications

References 8 publications

Photosensitizing Antivirals

Photosensitizing Antivirals

Antimicrobial activity of the protozoan toxin climacostol and its derivatives

Variations in the efficiency of ciliate extrusomal toxins against a common ciliate predator, the catenulidStenostomum Sphagnetorum

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