Synthesis and Evaluation of Bakuchiol Derivatives as Potential Anticancer Agents

Abstract

A series of bakuchiol derivatives were synthesized and evaluated for their anti-proliferative and the inhibitory activities on SMMC7721 cell line migration using PX-478 as a positive control. The results showed (S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10) to have the best activity among the tested compounds, which included PX-478. In addition, compound 10 showed greater inhibitory activity than that of bakuchiol in the transwell migration and invasion assays at every dose. In western blotting tests, compound 10 showed a promising ability to downregulate the expression of HIF-1α and its associated downstream proteins MMP-2 and MMP-9. Moreover, this effect was dose-dependent and could represent a possible mechanism of action for the anticancer activity of compound 10.

New derivatives of a natural nordentatin

“…The UV-vis spectra were obtained on a Shimadzu (UV-1800) UV-vis spectrometer. The target compounds (1a-1j) were semi-synthesized by an acylation method with slight modification [19,20]. The starting material, nordentatin (1), was collected from our previous research [2].…”

Bakuchiol – a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches

“…Notably, bromopropane, with anhydrous K 2 CO 3 in acetone as the catalyst affords O-alkylated derivative 81 (Scheme 21a) and acyl derivatives 82 obtained by treating 1 with appropriate alkanoic anhydride in presence of catalytic amount of DMAP (Scheme 21b). 47 Bakusylan ( 83) is an novel hybrid molecule prepared from salicylic acid with bakuchiol (1) via modied Steglich esterication method using DCC as condensing agent and DMAP as catalyst (Scheme 21c). 68 Recently, Li and co-workers (2021) introduced a well-dened cationic amphiphilic groups under non-catalytic system.…”

“…Notably, bromopropane, with anhydrous K 2 CO 3 in acetone as the catalyst affords O -alkylated derivative 81 ( Scheme 21a ) and acyl derivatives 82 obtained by treating 1 with appropriate alkanoic anhydride in presence of catalytic amount of DMAP ( Scheme 21b ). 47 …”

“… 79 From this view point, Wu and co-workers adopted this p -TSA–Ni(NO 3 ) 2 catalytic system for nitration on bakuchiol ( Scheme 24a ) at C(3)-position. In another study, Chen and co-workers, 47 used MgCl 2 –Et 3 N systems 80 for formylation ( Scheme 24b ).…”

Bakuchiol—A new allergen in cosmetics

“…17015‐60‐0) is a purified meroterpene phenol, and is found mainly in Psoralea corylifolia (babchi seeds), as well as in some other Asian plants, for example, Psoralea glandulosa , Pimelea drupaceae (cherry riceflower), and Ulmus davidiana (Father David elm) . In in vitro and experimental models, bakuchiol has shown various biological properties, including anticancer, antioxidant, oestrogen‐like, antimicrobial, antifungal, liver‐protective, antidiabetic and immune‐suppressive activity . This compound has been found to reduce photoageing and to have antiacne activity, similarly to retinoids .…”