Does Genistein remain in resonance stabilised form in physiological pH or acidic pH? As a follow up, does the Carbonyl group at 4 position group get deprotonated or Hydroxyl group at 5 position get deprotonated? How does the resonance structure look? I have been looking through literature but have not been able to find any reference to this.
Does the deprotonation start with the carbonyl group or does it always have to start with hydroxyl group?
I may not sound clear as I am an amateur when it comes to organic chemistry.
The first acid dissociation constant for genistein ($\mathrm{p}K_\mathrm{a1}$) is $6.51 \pm 0.20$ (Ref.1), mainly because of hydrogen bonding between $\ce{C_{(4)}}$ carbonyl oxygen and $\ce{C_{(5)}-OH}$, similar to that in acetylacetone (see the diagram):

Therefore, in physiological $\mathrm{pH}$ ($\mathrm{pH} \approx 7.3$) it should be partially ionized. If it is in acedic solution, $\ce{C_{(4)}}$ carbonyl oxygen would be partially or fully protonated based on the acid strength of the solution. Furthermore, the energy minimized three-dimensional structure of genistein shows the hydrogen bonding as depicted in following image (See Figure A; Ref.1):

References:

Yoshiyuki Mizushina, Kazuaki Shiomi, Isoko Kuriyama, Yoshihiro Takahashi, Hiromi Yoshida, “Inhibitory effects of a major soy isoflavone, genistein, on human DNA topoisomerase II activity and cancer cell proliferation,” International Journal of Oncology 2013, 43(6), 1117-1124 (https://doi.org/10.3892/ijo.2013.2032).