https://www.rsc.org/suppdata/np/c2/c2np20049j/c2np20049j.pdf

Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae

Since the dawn of the 20th century, the average life expectancy at birth has nearly doubled due to advances in science and medicine. As medical records grew more reliable, it became apparent that, while overall life span was increasing, there were significant epidemiological differences between geographical regions, with people from countries such as Japan, France, and Switzerland enjoying longer life expectancy as compared to other regions of the world. The causative factors for these disparities in both mortality and morbidity have been attributed not only to genetics but also to the contributions of highly variable lifestyle and environmental influences.1 Barring differences in modernization and public health policy, diet is the most significant epidemiological factor cross-culturally and is thought to be a profoundly important contributor to health and overall well-being.

Prior to the early 1990s, there was a general consensus in support of the belief that moderate alcohol consumption significantly lowered the risk of coronary heart disease (CHD).2 However, it was not clear whether this was true of all alcoholic beverages or which constituents in the drinks were responsible for these beneficial properties.3 In 1992, Siemann and Creasy4 reported that resveratrol (1) was present in significant concentrations in red wine, drawing attention to the fact that it was also an active principle found in Japanese and Chinese folk medicines used to treat ailments related to the liver, skin, heart, and lipid metabolism.5 The discovery of resveratrol in wine was particularly timely; although the correlation between high fat and cholesterol consumption and coronary heart disease was widely accepted,6 certain populations, namely the French, had a low incidence of CHD mortality despite a diet and lifestyle that exposed these individuals to elevated risk factors.7 The cardioprotective ability of resveratrol, its oligomers, along with other phytochemicals present in wine, appeared to resolve this “French Paradox” and advanced the notion that a chemical constituent of one’s diet could be beneficial to health.8 Although the reality of the French Paradox remains contentious,9,10 research into the health benefits of resveratrol has exploded as a result. The reported biological activities of resveratrol are numerous, including antioxidant,11 anticancer,12 antidiabetic,13,14 cardioprotective,15 and even antiaging properties,16 to name a few. The body of literature regarding the biological activity of resveratrol is expansive and beyond of the scope of this review. We invite the readers to the following resources for background on this exciting and ongoing field of research.17−21

Despite its enormous popularity, resveratrol is but a single compound in a large, structurally diverse class of oligomeric stilbenoids that are present in the wines and foods that we consume.22,23 Until recently, access to these oligomeric natural products was limited to isolation from natural sources, which severely hampered their biological evaluation. The scientific interest in resveratrol has undoubtedly instigated the renewed attention in these compounds by the chemical community. Advances in the characterization, isolation techniques, and synthesis of these natural products have significantly enriched our understanding of their chemistry and biology. Our review seeks to document the history and recent progress in the isolation, chemical synthesis, and biology of this fascinating class of phytochemicals, while providing new insight on the biosynthesis and future prospects for the field as a whole.

Chemistry and Biology of Resveratrol-Derived Natural Products

In addition to the commonly used classification as hydrolyzable tannins and condensed tannins, tannins can also be categorized into two other types: polyphenols of constant chemical structure (Type A) and polyphenols of variable composition (Type B). Both types of tannins and related polyphenols account for a large part of plant polyphenols, but accurate structure-activity correlations on a molecular basis can be determined mainly for type A compounds, among which are hydrolysable tannins such as the ellagitannins and their oxidized congeners, some gallotannins, epigallocatechin gallate, caffetannins, etc. Among the activities determined on a molecular basis are the chemical, biological and pharmacological actions such as superoxide anion scavenging, apoptosis, antitumor, anti-EVB, anti-MRSA and anti-plasmin inhibitory activities, etc., in addition to their fundamental activities, i.e., binding to proteins, large molecular compounds and metallic ions, and antioxidant activities. Some structure-specific activities were found for the condensation of dehydroellagitannins with co-existing compounds under mild conditions, and the host-mediated antitumor actions of ellagitannin oligomers. Structures and activities of metabolites of geraniin, a dehydroellagitannin, were revealed. Some stilbenoids and phlorotannins of firm structures have been known to have many activities similar to those of the type A tannins.

/pdf/tannins-of-constant-structure-in-medicinal-and-food-plants-1usnqnkxpp.pdf

Tannins of Constant Structure in Medicinal and Food Plants—Hydrolyzable Tannins and Polyphenols Related to Tannins

Abiotic stressors such as extreme temperatures, drought, flood, light, salt, and heavy metals alter biological diversity and crop production worldwide. Therefore, it is important to know the mechanisms by which plants cope with stress conditions. Polyphenols, which are the largest group of plant-specialized metabolites, are generally recognized as molecules involved in stress protection in plants. This diverse group of metabolites contains various structures, from simple forms consisting of one aromatic ring to more complex ones consisting of large number of polymerized molecules. Consequently, all these molecules, depending on their structure, may show different roles in plant growth, development, and stress protection. In the present review, we aimed to summarize data on how different polyphenol structures influence their biological activity and their roles in abiotic stress responses. We focused our review on phenolic acids, flavonoids, stilbenoids, and lignans.

https://www.mdpi.com/2223-7747/10/1/118/pdf

The Role of Polyphenols in Abiotic Stress Response: The Influence of Molecular Structure

Most anti-cancer drugs are derived from natural resources such as marine, microbial and botanical sources. Cutaneous malignant melanoma is the most aggressive form of skin cancer, with a high mortality rate. Various treatments for malignant melanoma are available, but due to the development of multi-drug resistance, current or emerging chemotherapies have a relatively low success rates. This emphasizes the importance of discovering new compounds that are both safe and effective against melanoma. In vitro testing of melanoma cell lines and murine melanoma models offers the opportunity for identifying mechanisms of action of plant derived compounds and extracts. Common anti-melanoma effects of natural compounds include potentiating apoptosis, inhibiting cell proliferation and inhibiting metastasis. There are different mechanisms and pathways responsible for anti-melanoma actions of medicinal compounds such as promotion of caspase activity, inhibition of angiogenesis and inhibition of the effects of tumor promoting proteins such as PI3-K, Bcl-2, STAT3 and MMPs. This review thus aims at providing an overview of anti-cancer compounds, derived from natural sources, that are currently used in cancer chemotherapies, or that have been reported to show anti-melanoma, or anti-skin cancer activities. Phytochemicals that are discussed in this review include flavonoids, carotenoids, terpenoids, vitamins, sulforaphane, some polyphenols and crude plant extracts.

Review of Natural Compounds for Potential Skin Cancer Treatment

Stilbenoids are formed by a particular branch of the flavonoid biosynthetic pathway. They are of special interest to natural product researchers for their roles in plant resistance to fungal pathogens and their biological effects. This review in the volume of Bioactive Natural Products provides a comprehensive account of the occurrence, chemistry, biological roles and activities of the stilbenoids. Nearly 800 stilbenoids, isolated from natural sources in the recent 12 years, are grouped into structural types and discussed in terms of their reported pharmacological activity. The major groups of stilbenoids which are discussed in detail include stilbenes, bibenzyls, bisbibenzyls, phenanthrenoids, stilbene oligomers etc. Detailed tables and figures list the occurrence of stilbenoids in major plant species, and methods used for extracting and analyzing stilbenoids are discussed. Biosynthetic pathways and chemical synthesis are reviewed and the biological activities of stilbenoids are also addressed. The coverage of the new structures is from 1994 to 2006.

Hong Jun Zhang

Papers

Stilbenoids: Chemistry and bioactivities