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Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth
- Source :
- Journal of agricultural and food chemistry. 63(44)
- Publication Year :
- 2015
-
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.
- Subjects :
- Breast Neoplasms
Saccharomyces cerevisiae
chemistry.chemical_compound
Structure-Activity Relationship
Amide
Lactobacillus
Cell Line, Tumor
Cytotoxic T cell
Humans
Cytotoxicity
IC50
Cell Proliferation
biology
Chemistry
Plant Extracts
Daidzein
General Chemistry
biology.organism_classification
Amides
Growth Inhibitors
Lactic acid
Soy Milk
Biochemistry
Fermentation
Lactates
Female
Soybeans
General Agricultural and Biological Sciences
Subjects
Details
- ISSN :
- 15205118
- Volume :
- 63
- Issue :
- 44
- Database :
- OpenAIRE
- Journal :
- Journal of agricultural and food chemistry
- Accession number :
- edsair.doi.dedup.....c727c5bd79991a5ebfd8c440b9304491