More Than Resveratrol: New Insights into Stilbene-Based Compounds

Abstract

The concept of a scaffold concerns many aspects at different steps on the drug development path. In medicinal chemistry, the choice of relevant “drug-likeness” scaffold is a starting point for the design of the structure dedicated to specific molecular targets. For many years, the chemical uniqueness of the stilbene structure has inspired scientists from different fields such as chemistry, biology, pharmacy, and medicine. In this review, we present the outstanding potential of the stilbene-based derivatives. Naturally occurring stilbenes, together with powerful synthetic chemistry possibilities, may offer an excellent approach for discovering new structures and identifying their therapeutic targets. With the development of scientific tools, sophisticated equipment, and a better understanding of the disease pathogenesis at the molecular level, the stilbene scaffold has moved innovation in science. This paper mainly focuses on the stilbene-based compounds beyond resveratrol, which are particularly attractive due to their biological activity. Given the “fresh outlook” about different stilbene-based compounds starting from stilbenoids with particular regard to isorhapontigenin and methoxy- and hydroxyl- analogues, the update about the combretastatins, and the very often overlooked and underestimated benzanilide analogues, we present a new story about this remarkable structure.

The Potential Role of Polyphenols in Modulating Mitochondrial Bioenergetics within the Skeletal Muscle: A Systematic Review of Preclinical Models

“… The chemical structure of pinosylvin, a stilbene-based compound found in plants, berries, and nuts [ 58 ]. …”

Pinosylvin Shifts Macrophage Polarization to Support Resolution of Inflammation

“…Stilbenoids are most commonly found in berries or fruits but also in other types of plants such as ferns and mosses [ 6 , 7 ]. In the present study, we focused on a fairly unexplored stilbenoid, pinosylvin, which can be found particularly in the knots of Pinus sylvestris , also known as Scots pine [ 8 ]. We also used perhaps the most researched stilbenoid, resveratrol, and the structurally closely related pine stilbenoid monomethyl pinosylvin ( Figure 1 ) as a comparison for the principal effects of pinosylvin.…”

Synthesis and Antiproliferative Evaluation of 3-Chloroazetidin-2-ones with Antimitotic Activity: Heterocyclic Bridged Analogues of Combretastatin A-4

“…Imines 9w and 9x are designed to replace the 3,4,5-trimethoxyaryl Ring A with the alternative 3,5-dimethoxyphenyl substitution. This substitution pattern is characteristic of stilbenes such as resveratrol (3,4 ,5-trihydroxystilbene) identified as having therapeutic and chemopreventive roles in colorectal and skin cancers [61,62], and is also present in the related stilbenes pinosylvin, isorhapontigenin, pterostilbene [63,64], which also elicit anti-cancer properties. The structure of the imine 9o was confirmed using X-ray crystallography (Figure 2 and Table 1) showing the E configuration of the imine with an N1-C2 bond length of 1.280(2) Å.…”