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Hierridin B ( 6 ), a methylated hydroquinone isolated from the marine picocyanobacterium  Cyanobium  sp. LEGE 06113, moderately inhibited the growth of colon adenocarcinoma HT-29 cells. Aiming to improve the potential antitumor activity of this natural product, the demethylated analogue, norhierridin B ( 10 ), as well as its structurally-related quinone ( 9 ), were synthesized and evaluated for their growth inhibitory effect on a panel of human tumor cell lines, including the triple-negative breast cancer (TNBC) cells MDA-MB-231, SKBR3, and MDA-MB-468. Norhierridin B ( 10 ) showed a potent growth inhibitory effect on all cancer cell lines. Moreover, the growth inhibitory effect of compound  10  on MDA-MB-231 cells was associated with cell cycle arrest and apoptosis. Norhierridin B ( 10 ) interfered with several p53 transcriptional targets, increasing p21, Bax, and MDM2, while decreasing Bcl-2 protein levels, which suggested the potential activation of a p53 pathway. Altogether, these results evidenced a great improvement of the antitumor activity of hydroquinone  10  when compared to  6  and its structurally-related quinone ( 9 ). Notably, hydroquinone  10  displayed a prominent growth inhibitory activity against TNBC cells, which are characterized by high therapeutic resistance.

Norhierridin B, a New Hierridin B-Based Hydroquinone with Improved Antiproliferative Activity