Journal
JOURNAL OF NATURAL PRODUCTS
Volume 79, Issue 8, Pages 2039-2044Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.6b00335
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Funding
- Russian Science Foundation [14-13-00263]
- Russian Science Foundation
- Russian Science Foundation [14-13-00263] Funding Source: Russian Science Foundation
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An original synthesis of the acetogenin muricadienin, the bioprecursor of solamin, has been developed. The key step in the five-step 41% overall yield synthesis is the catalytic cross-cydomagnesiation reaction of functionally substituted 1,2-dienes with EtMgBr in the presence of Cp2TiCl2 and magnesium metal. It has been demonstrated for the first time that muricadienin exhibits a moderate in vitro inhibitory activity against topoisomerases I and II alpha, key cell cycle enzymes. Using flow cytometry, muricadienin was shown to have high cytotoxicity toward the HEK293 kidney cancer cells (IC50 0.39 mu M).
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