|Title:||Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth||Authors:||Ke, Y.-Y.
|Keywords:||breast cancer; cytotoxicity; fermentation; latifolicinin; organic synthesis; soymilk||Issue Date:||2015||Journal Volume:||63||Journal Issue:||44||Start page/Pages:||9715-9721||Source:||Journal of Agricultural and Food Chemistry||Abstract:||
The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of β-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and l-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their l-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 μM) and 10-fold less toxic to Detroit-551 normal cells. ? 2015 American Chemical Society.
|DOI:||10.1021/acs.jafc.5b04028||metadata.dc.subject.other:||Amides; Amino acids; Cytology; Cytotoxicity; Diseases; Esters; Fermentation; Flavonoids; Lactic acid; Breast Cancer; Cytotoxic activities; Fermentation process; Functional components; latifolicinin; Organic synthesis; Soy milk; Structure activity relationships; Cells; amide; beta-(4-hydroxyphenyl)lactic acid farnesyl amide; growth inhibitor; lactic acid derivative; latifolicinin A; plant extract; breast tumor; cell proliferation; chemistry; drug effects; female; fermentation; human; Lactobacillus; metabolism; microbiology; pathophysiology; pharmacology; Saccharomyces cerevisiae; soybean; soybean milk; structure activity relation; tumor cell line; Amides; Breast Neoplasms; Cell Line, Tumor; Cell Proliferation; Female; Fermentation; Growth Inhibitors; Humans; Lactates; Lactobacillus; Plant Extracts; Saccharomyces cerevisiae; Soy Milk; Soybeans; Structure-Activity Relationship
|Appears in Collections:||化學系|
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