Conithiaquinones A and B, Tetracyclic Cytotoxic Meroterpenes from the Mediterranean Ascidian <i>Aplidium conicum</i>

Ascidians of the genus Aplidium are recognized as an important source of chemical diversity and bioactive natural products. Among the compounds produced by this genus are non-nitrogenous metabolites, mainly prenylated quinones and hydroquinones. This review discusses the isolation, structural elucidation, and biological activities of quinones, hydroquinones, rossinones, longithorones, longithorols, floresolides, scabellones, conicaquinones, aplidinones, thiaplidiaquinones, and conithiaquinones. A compilation of the 13C-NMR spectral data of these compounds is also presented.

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“…Conithiaquinone A ( 52 ) demonstratedmoderate cytotoxicity against MCF-7 cells with an IC 50 value of 44.5 μM [58]. …”

Section: Introductionmentioning

confidence: 99%

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

et al. 2014

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“…Specifically, time-dependent density functional theory (TDDFT) was used to calculate the ECD spectra of the two possible enantiomers of 1 . 7 Using GaussSum 2.2, 8 the theoretical ECD spectra were then compared to the actual 1 ECD spectra (experimentally determined in MeOH, see Supporting Information, Figure S14). This comparison revealed a best experimental/actual ECD spectral match for the 1 R , 3 R , 5 S , 10a R isomer (Figure 3).…”

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confidence: 99%

Ruthmycin, a New Tetracyclic Polyketide from Streptomyces sp. RM-4-15

et al. 2013

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The isolation and structural elucidation of a new tetracyclic polyketide (ruthmycin) from Streptomyces sp. RM-4-15, a bacteria isolated near thermal vents from the Ruth Mullins underground coal mine fire in eastern Kentucky, is reported. In comparison to the well-established frenolicin core scaffold, ruthmycin possesses an unprecedented signature C3 bridge and corresponding fused six member ring. Preliminary in vitro antibacterial, anticancer and antifungal assays revealed ruthmycin to display moderate antifungal activity.

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“…[18][19][20][21][22] Although the calculated absorptions did not fit exactly with the experimentally determined absorption positions (Figure 3), the general features of the ECD spectrum calculated for the 5S,8R,9S,10S isomer showed a much better match with the experimental data than did the inverted spectrum calculated for its enantiomer. As an alternative, electronic circular dichroism (ECD) analysis was used to establish the absolute configuration of 1.…”

Section: Resultsmentioning

confidence: 74%