Resveratrol and Resveratrol Analogues—Structure—Activity Relationship

Abstract

Resveratrol (3,4',5-trihydroxy-trans-stilbene) is a compound found in wine and is held responsible for a number of beneficial effects of red wine. Besides the prevention of heart disease and significant anti-inflammatory effects, resveratrol might inhibit tumor cell growth and even play a role in the aging process. We here describe the structure-activity relationship of resveratrol and analogues of resveratrol regarding the free radical scavenging and antitumor effects of this exciting natural compound. In addition, we have synthesized a number of analogues of resveratrol with the aim to further improve the beneficial effects of resveratrol. Our studies were based on the analysis of structural properties, which were responsible for the most important effects of this compound. Striking in vivo effects can be observed with hexahydroxystilbene (M8), the most effective synthetic analogue of resveratrol. We could show that M8 inhibits tumor as well as metastasis growth of human melanoma in two different animal models, alone and in combination with dacarbacine.

Tubulin-interactive stilbene derivatives as anticancer agents

“…It occurs in the human diet as a constituent of peanuts, grapes and red wine. Its chemopreventive activity is supposed to be related to its ability to arrest cell cycle progression or to initiate tumor cell death by apoptosis [51]. Surprisingly, this compound does not interact with tubulin.…”

“…SAR analysis indicated the significance of the cis configuration of the olefinic bridge and 3,4,5-trimethoxyphenyl moiety in relation to the cytotoxic and anti-tubulin properties of stilbenes [3]. Substitution of the resveratrol molecule hydroxy groups with methoxy substituents improves the bioavailability of the compound by inhibiting conjugation reactions with sulphuric or glucuronic acids [51]. A methylated derivative of cis-resveratrol, 3,4',5-trimethoxy-cis-stilbene (Fig.…”

The Inhibitory Effect of Natural Stilbenes and Their Analogues on Catalytic Activity of Cytochromes P450 Family 1 in Comparison with Other Phenols - Structure and Activity Relationship

“…In the last decade, new stilbene derivatives have been designed and synthesized in order to find more potent chemopreventive agents (Szekeres et al, 2010). The additional aim of this approach was to find resveratrol derivatives demonstrating better bioavailability in comparison to the parent compound.…”

“…Among this group, stilbenoids are compounds displaying multiple activities of interest with regard to cancer prevention and therapy, and their anticancer properties have been proven in various animal models (Szekeres et al, 2010). In this review, we summarize the results of studies on inhibitory activity of trans-resveratrol (3,4',5-trimethoxy-trans-stilbene), the best recognized trans-stilbene (Figure 1), and its natural and synthetic analogues toward expression and activity of CYPs responsible for procarcinogen activation.…”

Effect of different presentations of resveratrol on cell proliferation and epitelial thickness of the oral mucosa of wistar rats

“…The relationship between diet and health has prompted intense research into bioactive compounds in foods. Resveratrol is a bioactive compound that can be found in grape skin (e.g., grape juice, wine and compounding solution of resveratrol) and may have been partly responsible for the health-promoting properties observed in populations in the Mediterranean region 3,4 . There has been a growing interest in the role of antioxidants, such as resveratrol, in oral and dental tissues.…”