Journal
FOOD CHEMISTRY
Volume 338, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2020.127656
Keywords
Estrogenic activity; Bisguaiacol; Structure-activity relationships; MCF-7; VM7Luc4E2; Lignin-derivable
Funding
- National Science Foundation [DMR-1506623]
Ask authors/readers for more resources
This study investigated the estrogenic activity of six newly synthesized bisguaiacols, which showed undetectable activity at concentrations lower than 10(-7) M and significantly lower activity than BPA within an environmentally relevant range. Addition of a single methoxy group led to a significant reduction in activity, while incorporation of more methoxy groups had subtle but pronounced impacts. In conclusion, these lignin-inspired bisguaiacols are seen as promising sustainable alternatives to BPA and BPF.
Bisguaiacols are promising lignin-derivable alternatives to bisphenol A (BPA), but limited bioassay data are available on their estrogenic activity (EA). Herein, we investigated the estrogen receptor alpha (ER alpha)-mediated EA of six newly synthesized bisguaiacols, which differed in the number and location of methoxy substituents, through in vitro assays: MCF-7 cell proliferation and VM7Luc4E2 transactivation. The six bisguaiacols had undetectable EA at concentrations less than 10(-7) M, most importantly, with significantly lower EA than BPA over an environmentally relevant range of 10(-10)-10(-7) M. Adding a single methoxy group led to significant reduction in EA in all cases, relative to BPA and one petroleum-derived BPA analogue (bisphenol F, BPF), and the incorporation of more methoxy groups had subtler, but pronounced, impacts on either ER alpha binding or MCF-7 cell proliferation. In short, the six lignin-inspired bisguaiacols presented herein are viewed as promising sustainable alternatives to BPA and BPF.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available