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Synthesis and structure--activity relationship of violaceoid D, a cytotoxic alkylated phenol isolated from Aspergillus violaceofuscus Gasperini.
- Source :
-
Bioscience, Biotechnology & Biochemistry . Apr2023, Vol. 87 Issue 4, p363-370. 8p. - Publication Year :
- 2023
-
Abstract
- The enantioselective synthesis of violaceoid D, a cytotoxic phenolic compound isolated from the culture broth of Aspergillus violaceofuscus Gasperini, was achieved. The total synthesis involves stereoselective construction of the stereogenic center of violaceoid D via Sharpless asymmetric dihydroxylation, followed by Smiles rearrangement. The absolute configuration of natural violaceoid D was determined to be R from the specific rotation value. Synthesized violaceoid D and its analogs were evaluated for cytotoxicity against two human cancer cell lines, Jurkat and HCT116. Because the enantiomer of violaceoid D showed no cytotoxicity, it is plausible that violaceoid D binds selectively to specific target molecules, such as proteins in the cancer cells. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ASPERGILLUS
*PHENOL
*CANCER cells
*CELL lines
Subjects
Details
- Language :
- English
- ISSN :
- 09168451
- Volume :
- 87
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Bioscience, Biotechnology & Biochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 162612232
- Full Text :
- https://doi.org/10.1093/bbb/zbac212