| RRC ID |
74898
|
| Author |
Shoji A, Arai Y, Asakawa R, Saito T, Kuramochi K, Yajima A.
|
| Title |
Synthesis and structure-activity relationship of violaceoid D, a cytotoxic alkylated phenol isolated from Aspergillus violaceofuscus Gasperini.
|
| Journal |
Biosci Biotechnol Biochem
|
| 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.
|
| Volume |
87(4)
|
| Pages |
363-370
|
| Published |
2023-3-21
|
| DOI |
10.1093/bbb/zbac212
|
| PII |
6967133
|
| PMID |
36592963
|
| MeSH |
Antineoplastic Agents* / pharmacology
Humans
Molecular Structure
Phenol*
Phenols / pharmacology
Stereoisomerism
Structure-Activity Relationship
|
| IF |
1.516
|
| Resource |
| Human and Animal Cells |
HCT116(RCB2979) |
