Photopiperazines A–D, Photosensitive Interconverting Diketopiperazines with Significant and Selective Activity against U87 Glioblastoma Cells, from a Rare, Marine-Derived Actinomycete of the Family Streptomycetaceae
| Autor: | Min-Cheol Kim, Jeffrey J. Rodvold, William Fenical, Henrique Machado, Reiko Cullum, Inho Yang, Alexander Smith |
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| Rok vydání: | 2019 |
| Předmět: |
Stereochemistry
Streptomycetaceae Pharmaceutical Science 01 natural sciences Piperazines Analytical Chemistry Cell Line Tumor Drug Discovery Humans Cytotoxic T cell Diketopiperazines Pharmacology Strain (chemistry) biology Brain Neoplasms 010405 organic chemistry Chemistry Organic Chemistry 16S ribosomal RNA biology.organism_classification 0104 chemical sciences Actinobacteria 010404 medicinal & biomolecular chemistry Complementary and alternative medicine Cell culture Molecular Medicine Drug Screening Assays Antitumor Glioblastoma Two-dimensional nuclear magnetic resonance spectroscopy Cis–trans isomerism Bacteria |
| Zdroj: | Journal of Natural Products. 82:2262-2267 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.9b00429 |
| Popis: | Photopiperazines A-D (1-4), unsaturated diketopiperazine derivatives, were isolated from the culture broth of a rare, marine-derived actinomycete bacterium, strain AJS-327. This strain shows very poor 16S rRNA sequence similarity to other members of the actinomycete family Streptomycetaceae, indicating it is likely a new lineage within this group. The structures of the photopiperazines were defined by analysis of HR-ESI-TOF-MS spectra in conjunction with the interpretation of 1D and 2D NMR data. The photopiperazines are sensitive to light, causing interconversion among the four olefin geometrical isomers, which made purification of each isomer challenging. The photopiperazines are highly cytotoxic metabolites that show selective toxicity toward U87 glioblastoma and SKOV3 ovarian cancer cell lines. |
| Databáze: | OpenAIRE |
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