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Book ChapterDOI

Stilbenoids: Chemistry and bioactivities

TL;DR: Stilbenoids are formed by a particular branch of the flavonoid biosynthetic pathway and are of special interest to natural product researchers for their roles in plant resistance to fungal pathogens and their biological effects as discussed by the authors.
Abstract: 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.
Citations
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Journal ArticleDOI
TL;DR: This review focuses on the distribution of stilbenes and 2-arylbenzofuran derivatives in the plant kingdom, the chemical structure of stILbenes in the Vitaceae family and their taxonomic implication.

288 citations

Journal ArticleDOI
TL;DR: The history and recent progress in the isolation, chemical synthesis, and biology of this fascinating class of phytochemicals is documented, while providing new insight on the biosynthesis and future prospects for the field as a whole is provided.
Abstract: 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.

251 citations

Journal ArticleDOI
TL;DR: In this article, the 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, caffetannin, etc.
Abstract: 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.

237 citations


Cites background from "Stilbenoids: Chemistry and bioactiv..."

  • ...Stilbenoids have been found to form oligomers up to hexamers, often in the plants grown in southern Asia and nearby areas, particularly those used in traditional medicines [94–97]....

    [...]

Journal ArticleDOI
08 Jan 2021
TL;DR: In this article, the authors focused on phenolic acids, flavonoids, stilbenoids, and lignans and focused their review on how different polyphenol structures influence their biological activity and their roles in abiotic stress responses.
Abstract: 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.

200 citations

Journal ArticleDOI
TL;DR: This review 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.
Abstract: 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.

200 citations


Cites background from "Stilbenoids: Chemistry and bioactiv..."

  • ...Stilbenes are part of the stilbenoid family of compounds found in nature that are characterized by two aromatic rings, being joined by a methylene bridge [168]....

    [...]

References
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Journal ArticleDOI
10 Jan 1997-Science
TL;DR: It is suggested that resveratrol, a common constituent of the human diet, merits investigation as a potential cancer chemopreventive agent in humans.
Abstract: Resveratrol, a phytoalexin found in grapes and other food products, was purified and shown to have cancer chemopreventive activity in assays representing three major stages of carcinogenesis. Resveratrol was found to act as an antioxidant and antimutagen and to induce phase II drug-metabolizing enzymes (anti-initiation activity); it mediated anti-inflammatory effects and inhibited cyclooxygenase and hydroperoxidase functions (antipromotion activity); and it induced human promyelocytic leukemia cell differentiation (antiprogression activity). In addition, it inhibited the development of preneoplastic lesions in carcinogen-treated mouse mammary glands in culture and inhibited tumorigenesis in a mouse skin cancer model. These data suggest that resveratrol, a common constituent of the human diet, merits investigation as a potential cancer chemopreventive agent in humans.

4,786 citations

Book
01 Jun 1972
TL;DR: The chemistry and biology of Rocaglamides and related derivatives from Aglaia species (Meliacease) are discussed in detail in a recent paper by.
Abstract: S. S. Ebada, N. Lajkiewicz, J. A. Porco Jr., M. Lin-Weber, and P. Proksch: Chemistry and biology of Rocaglamides (=Flavaglines) and related derivatives from Aglaia species (Meliacease). - M. A. R. C. Bulusu, K. Baumann, and A. Stuetz: Chemistry of the immunomodulatory macrolides ascomycin and related analogues. - R. I. Misico, V. Nicotra, J. C. Oberti, G. Barboza, R. R. Gil, and G. Burton: Withanolides and related steroids.

2,115 citations

Journal Article
TL;DR: In vivo, resveratrol blocks the multistep process of carcinogenesis at various stages: it blocks carcinogen activation by inhibiting aryl hydrocarbon-induced CYP1A1 expression and activity, and suppresses tumor initiation, promotion and progression.
Abstract: Resveratrol, trans-3,5,4'-trihydroxystilbene, was first isolated in 1940 as a constituent of the roots of white hellebore (Veratrum grandiflorum O. Loes), but has since been found in various plants, including grapes, berries and peanuts. Besides cardioprotective effects, resveratrol exhibits anticancer properties, as suggested by its ability to suppress proliferation of a wide variety of tumor cells, including lymphoid and myeloid cancers; multiple myeloma; cancers of the breast, prostate, stomach, colon, pancreas, and thyroid; melanoma; head and neck squamous cell carcinoma; ovarian carcinoma; and cervical carcinoma. The growth-inhibitory effects of resveratrol are mediated through cell-cycle arrest; upregulation of p21Cip1/WAF1, p53 and Bax; down-regulation of survivin, cyclin D1, cyclin E, Bcl-2, Bcl-xL and clAPs; and activation of caspases. Resveratrol has been shown to suppress the activation of several transcription factors, including NF-kappaB, AP-1 and Egr-1; to inhibit protein kinases including IkappaBalpha kinase, JNK, MAPK, Akt, PKC, PKD and casein kinase II; and to down-regulate products of genes such as COX-2, 5-LOX, VEGF, IL-1, IL-6, IL-8, AR and PSA. These activities account for the suppression of angiogenesis by this stilbene. Resveratrol also has been shown to potentiate the apoptotic effects of cytokines (e.g., TRAIL), chemotherapeutic agents and gamma-radiation. Phamacokinetic studies revealed that the target organs of resveratrol are liver and kidney, where it is concentrated after absorption and is mainly converted to a sulfated form and a glucuronide conjugate. In vivo, resveratrol blocks the multistep process of carcinogenesis at various stages: it blocks carcinogen activation by inhibiting aryl hydrocarbon-induced CYP1A1 expression and activity, and suppresses tumor initiation, promotion and progression. Besides chemopreventive effects, resveratrol appears to exhibit therapeutic effects against cancer. Limited data in humans have revealed that resveratrol is pharmacologically quite safe. Currently, structural analogues of resveratrol with improved bioavailability are being pursued as potential therapeutic agents for cancer.

1,377 citations

Journal ArticleDOI
TL;DR: The African treeCombretum caffrum (Combretaceae) has been found to contain a powerful inhibitor of tubulin polymerization (IC502–3 μM), the growth of murine lymphocytic leukemia and human colon cancer cell lines.
Abstract: The African tree Combretum caffrum (Combretacae) has been found to contain a powerful inhibitor of tubulin polymerization (IC50 2-3 microM), the growth of murine lymphocytic leukemia (L 1210 and P 388 with ED50 approximately 0.003 microM and human colon cancer cell lines [(e.g. LoVo (ED50 = 0.005 microgram/ml), HT 29 (ED50 0.02 microgram/ml, Colo 205 (ED50 = 0.07 microgram/ml), DLD-1 (ED50 = 0.005 microgram/ml) and HCT-15 (ED50 = 0.0009 microgram/ml] designated combretastatin A-4 (1c). The structure assigned by spectral techniques was confirmed by synthesis.

707 citations

Journal ArticleDOI
14 Jan 1993-Nature
TL;DR: It is reported here that regenerated tobacco plants containing stilbene synthase genes are more resistant to infection by Botrytis cinerea, the first report of increased disease resistance in transgenic plants based on an additional foreign phytoalexin.
Abstract: Although phytoalexins have long been inferred to be important in the defence of plants against fungal infection, there are few reports showing that they provide resistance to infection. Several plants, including grapevine, synthesize the stilbene-type phytoalexin resveratrol when attacked by pathogens. Stilbenes with fungicidal potential are formed in several unrelated plant species, such as peanut (Arachis hypogaea), grapevine (Vitis vinifera) and pine (Pinus sylvestris). Stilbene biosynthesis only specifically requires the presence of stilbene synthase. Furthermore, the precursor molecules for the formation of hydroxy-stilbenes are malonyl-CoA and p-coumaroyl-CoA, both present in plants. To investigate the potential of stilbene biosynthetic genes in a strategy of engineering pathogen resistance, we isolated stilbene synthase genes from grapevine, where they are expressed at a high level, and transferred them into tobacco. We report here that regenerated tobacco plants containing these genes are more resistant to infection by Botrytis cinerea. This is, to our knowledge, the first report of increased disease resistance in transgenic plants based on an additional foreign phytoalexin.

670 citations