Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth.
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.
The Genomics Research Center, Academia Sinica , 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan.
Yi-Yu
YY
Ke
Department of Chemistry, National Taiwan University , 1 Roosevelt Road, Section 4, Taipei 106, Taiwan.
Chen-Hsuan
CH
Tsai
The Genomics Research Center, Academia Sinica , 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan.
Hui-Ming
HM
Yu
The Genomics Research Center, Academia Sinica , 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan.
Yu-Chen
YC
Jao
The Genomics Research Center, Academia Sinica , 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan.|Department of Chemistry, National Taiwan University , 1 Roosevelt Road, Section 4, Taipei 106, Taiwan.
Jim-Min
JM
Fang
The Genomics Research Center, Academia Sinica , 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan.
Chi-Huey
CH
Wong
D000577:Amides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000503:physiopathology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D005260:Female; D005285:Fermentation; D006131:Growth Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D007773:Lactates / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D007778:Lactobacillus / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D041942:Soy Milk / Q000737:chemistry* / Q000494:pharmacology*; D013025:Glycine max / Q000737:chemistry / Q000382:microbiology*; D013329:Structure-Activity Relationship
D000577:Amides; D006131:Growth Inhibitors; D007773:Lactates; D010936:Plant Extracts; C000608751:beta-(4-hydroxyphenyl)lactic acid farnesyl amide; C000608749:latifolicinin A
breast cancer; cytotoxicity; fermentation; latifolicinin; organic synthesis; soymilk