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Synthetic and Biological Studies of Juglorubin and Related Naphthoquinones.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Nov 01; Vol. 84 (21), pp. 13957-13966. Date of Electronic Publication: 2019 Oct 23. - Publication Year :
- 2019
-
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.
- Subjects :
- Anti-Bacterial Agents chemistry
Antineoplastic Agents chemistry
Bacillus subtilis drug effects
Cell Line, Tumor
Chemistry Techniques, Synthetic
Escherichia coli drug effects
Humans
Naphthoquinones chemistry
Anti-Bacterial Agents chemical synthesis
Anti-Bacterial Agents pharmacology
Antineoplastic Agents chemical synthesis
Antineoplastic Agents pharmacology
Naphthoquinones chemical synthesis
Naphthoquinones pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31596085
- Full Text :
- https://doi.org/10.1021/acs.joc.9b02119