Potential Antitumor Agents. XVII. Physalin B and 25,26-Epidihydrophysalin C From Witheringia coccoloboides

Antoun, Mikhail D.; Abramson, D.; Tyson, Richard L.; Chang, Ching-jer; McLaughlin, Jerry L.; Peck, Garnet; Cassady, John M.

doi:10.1021/np50017a013

Cited by 51 publications

(35 citation statements)

References 2 publications

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“…Compound 4a obtained by the hydrogenation of 4 was weaker than all the others, and compound 5 had no activity at the concentrations tested. Previous studies had already demonstrated that 2 and 3, but not 1, 4 and 5, were cytotoxic to tumor cell lines in vitro [9][10][11]19,20]. Thus, As mentioned before, previous studies of the biological activity of physalins led to the conclusion that the presence of the conjugated cyclohexenone moiety is essential for cytotoxicity [9,12].…”

Section: Biological Resultsmentioning

confidence: 84%

“…Based on these studies, it has been postulated that the presence of the double bond between C-2 and C-3 (ring A) is a fundamental chemical feature responsible for those actions [9,12,20]. In addition, Antoun et al [20] demonstrated that the 5,6-epoxy ring of physalins is also responsible for antitumor activity, and Lee and Houngton [19] recently reinforced the importance of the functional groups located at C-5 and C-6 as well. However, it seems that the structure requirements for cytotoxic activity are far from being decisively elucidated.…”

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confidence: 99%

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Preliminary Investigation of Structure-Activity Relationship of Cytotoxic Physalins

Magalhães¹,

Veras²,

Pessoa³

et al. 2006

LDDD

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Physalins D (1), B (2), F (3), 5α-ethoxy-6β-hydroxy-5,6-dihydrophysalin B (4) and E (5), all isolated from Physalis angulata L. extracts, were tested for cytotoxic activity using a panel of tumor cell lines and sea urchin eggs. In general, the most active compounds were 1 and 3, followed by 2 and 4. Compound 4a obtained by the hydrogenation of 4 was weaker than all the others in tumor cells and possessed no activity in sea urchin eggs. Compound 5 had no activity in tumor cells and exhibited activity in sea urchin eggs only in the third cleavage and blastulae. The present data suggest that the cytotoxic effect of physalins is probably determined by the combination of the conjugated cyclohexanone moiety and the presence of an oxygen located at both C-5 and C-6.

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Section: Biological Resultsmentioning

confidence: 84%

mentioning

confidence: 99%

Preliminary Investigation of Structure-Activity Relationship of Cytotoxic Physalins

Magalhães¹,

Veras²,

Pessoa³

et al. 2006

LDDD

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“…The positive control tested was rifampicin which has an MIC value of 0.2 mg/mL. The overall results suggested that the main compound in the fraction A1-29-12, which showed the antimycobacterial activity, is physalin D. Concerning the cytotoxic activity physalin B presents high activity (ID 50 0.32-0.35 mg/mL) against mouse tumour cells (Antoun et al, 1981). As far as we know, there is a lack of scientific evidence about the cytotoxicity of physalin D.…”

Section: Antimycobacterial Physalins 447mentioning

confidence: 96%

Antimycobacterial physalins from Physalis angulata L. (Solanaceae)

Januário

Filho

Pietro

et al. 2002

Phytotherapy Research

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Crude extracts and fractions from aerial parts of Physalis angulata have been bioassayed for antimycobacterial activity. Fraction A1-29-12 containing physalins B, F and D exhibited a minimum inhibitory concentration value (MIC) against Mycobacterium tuberculosis H(37)Rv strain of 32 microg/mL. Purified physalin B and physalin D were also tested showing MIC values against Mycobacterium tuberculosis H(37)Rv strain of > 128 microg/mL and 32 microg/mL respectively, suggesting that physalin D plays a relevant role in the antimycobacterial activity displayed. Structural elucidation of both physalins D and B was based on detailed (13)C and (1)H NMR spectral analysis with the aid of 2D-correlation spectroscopy ((1)H-(1)H, COSY, HSQC and HMBC). The assignment of the (13)C chemical shift for physalin D is reported here for the first time.

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“…26,27 Compound 1 (64 mg): the electrospray ionization mass spectrometry (ESIMS) showed a molecular ion at m/z 533. …”

Section: Structural Determination Of Physalin B and Cmentioning

confidence: 99%

High-Throughput Bioluminescence Screening of Ubiquitin-Proteasome Pathway Inhibitors from Chemical and Natural Sources

Ausseil

Samson²,

Aussagues

et al. 2007

SLAS Discovery

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To discover original inhibitors of the ubiquitin-proteasome pathway, the authors have developed a cell-based bioluminescent assay and used it to screen collections of plant extracts and chemical compounds. They first established a DLD-1 human colon cancer cell line that stably expresses a 4Ubiquitin-Luciferase (4Ub-Luc) reporter protein, efficiently targeted to the ubiquitinproteasome degradation pathway. The assay was then adapted to 96-and 384-well plate formats and calibrated with reference proteasome inhibitors. Assay robustness was carefully assessed, particularly cell toxicity, and the statistical Z´ factor value was calculated to 0.83, demonstrating a good performance level of the assay. A total of 18,239 molecules and 15,744 plant extracts and fractions thereof were screened for their capacity to increase the luciferase activity in DLD-1 4Ub-Luc cells, and 21 molecules and 66 extracts inhibiting the ubiquitin-proteasome pathway were identified. The fractionation of an active methanol extract of Physalis angulata L. aerial parts was performed to isolate 2 secosteroids known as physalin B and C. In a cell-based Western blot assay, the ubiquitinated protein accumulation was confirmed after a physalin treatment confirming the accuracy of the screening process. The method reported here thus provides a robust approach to identify novel ubiquitin-proteasome pathway inhibitors in large collections of chemical compounds and natural products. (Journal of Biomolecular Screening 2007:106-116)

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Potential Antitumor Agents. XVII. Physalin B and 25,26-Epidihydrophysalin C From Witheringia coccoloboides

Cited by 51 publications

References 2 publications

Preliminary Investigation of Structure-Activity Relationship of Cytotoxic Physalins

Preliminary Investigation of Structure-Activity Relationship of Cytotoxic Physalins

Antimycobacterial physalins from Physalis angulata L. (Solanaceae)

High-Throughput Bioluminescence Screening of Ubiquitin-Proteasome Pathway Inhibitors from Chemical and Natural Sources

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