Reference - Detail
| RRC ID | 57930 |
|---|---|
| Author | Kamo S, Saito T, Kusakabe Y, Tomoshige S, Uchiyama M, Tsubaki K, Kuramochi K. |
| Title | Synthetic and Biological Studies of Juglorubin and Related Naphthoquinones. |
| Journal | J Org Chem |
| Abstract |
Juglorubin, juglorescein, and juglocombins A/B are naturally occurring naphthoquinone dimers isolated from Streptomyces sp. These dimers are proposed to be biogenetically derived from juglomycin C, a monomeric naphthoquinone isolated from the same Streptomyces sp. In this study, the dimerization of a juglomycin C derivative, a key step in the total syntheses of these natural products, was investigated. Juglorubin was synthesized from the minor product of the dimerization via the formation of the juglocombin A/B stereoisomers. A mechanism for the dimerization reaction as well as a plausible biosynthetic pathway to obtain juglorubin from juglomycin C are proposed. Furthermore, the antibacterial and cytotoxic activities of five synthetic compounds were evaluated. Among the compounds tested in this study, 1'-O-methyljuglocombin B dimethyl ester and juglomycin C exhibited antibacterial activity against Bacillus subtilis. 1'-O-Methyljuglocombin B dimethyl ester and juglomycin C showed cytotoxicity against human colon carcinoma HCT116 cells and human leukemia HL-60 cells. 1'-O-Methyljuglocombin B dimethyl ester exhibited cytotoxicity against human normal MRC-5 cells as strong as that against human cancer cells. In contrast, juglomycin C was less toxic against normal MRC-5 cells, indicating a significant selectivity toward cancer cells. |
| Volume | 84(21) |
| Pages | 13957-13966 |
| Published | 2019-11-1 |
| DOI | 10.1021/acs.joc.9b02119 |
| PMID | 31596085 |
| MeSH | Anti-Bacterial Agents / chemical synthesis* Anti-Bacterial Agents / chemistry Anti-Bacterial Agents / pharmacology* Antineoplastic Agents / chemical synthesis* Antineoplastic Agents / chemistry Antineoplastic Agents / pharmacology* Bacillus subtilis / drug effects Cell Line, Tumor Chemistry Techniques, Synthetic Escherichia coli / drug effects Humans Naphthoquinones / chemical synthesis* Naphthoquinones / chemistry Naphthoquinones / pharmacology* |
| IF | 4.335 |
| Altmetric score |
オルトメトリクス指標項目
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| The most frequently cited source | X(Twitter) |
| Total number of mentions | 11 |
| Altmetric score changes over past 6months | 0.0 |
| Resource | |
| Human and Animal Cells | HCT116(RCB2979) HL-60 |