Beyond resveratrol: A review of natural stilbenoids identified from 2009–2013

Niesen, Daniel B.; Hessler, Craig; Seeram, Navindra P.

doi:10.3233/jbr-130062

Cited by 54 publications

(45 citation statements)

References 46 publications

(77 reference statements)

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“…The majority of resveratrol tetramers contain a benzofuran moiety because the tetramers are primarily “dimers of dimers” [ 13 ]. Since 2010, 13 resveratrol tetramers ( 69 – 81 ) were isolated and identified, whereas, ten tetramers were discovered in the plants of Dipterocarpaceae ( Table A1 ; Figure 5 ).…”

Section: Phytochemistrymentioning

confidence: 99%

“…As the research information on REVs has accumulated, several reviews appeared from 2010 to 2017 [ 1 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. In 2013, the biosynthesis, chemistry, and proprieties of REVs in grapes were summarized by Riccardo et al [ 11 ]; the structures of oligostilbenoids in Dipterocarpaceae plants and their biological activities were reviewed [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…In 2013, the biosynthesis, chemistry, and proprieties of REVs in grapes were summarized by Riccardo et al [ 11 ]; the structures of oligostilbenoids in Dipterocarpaceae plants and their biological activities were reviewed [ 12 ]. Another review published in 2013 [ 13 ] summarized 60 stilbenes, including 27 REVs found from 2009 to 2013, but the source plants were not mentioned. In 2014, Lim et al reviewed resveratrol and its oligomers in modulating sphingolipid metabolism and signaling in diseases [ 14 ]; another article in 2014 reviewed REVs for the prevention and treatment of cancers [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

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Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers

Shen

Zhou

et al. 2017

Molecules

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Resveratrol oligomers (REVs), a major class of stilbenoids, are biosynthesized by regioselective oxidative coupling of two to eight units of resveratrol monomer. Due to their unique structures and pleiotropic biological activities, natural product chemists are increasingly focusing on REVs in the last few decades. This study presents a detailed and thorough examination of REVs, including chemical structures, natural resources, and biological activities, during the period of 2010–2017. Ninety-two new REVs compounds, including 39 dimers, 23 trimers, 13 tetramers, six resveratrol monomers, six hexamers, four pentamers, and one octamer, have been reported from the families of Dipterocarpaceae, Paeoniaceae, Vitaceae, Leguminosae, Gnetaceae, Cyperaceae, Polygonaceae Gramineae, and Poaceae. Amongst these families, Dipterocarpaceae, with 50 REVs, accounts for the majority, and seven genera of Dipterocarpaceae are involved, including Vatica, Vateria, Shorea, Hopea, Neobalanocarpus, Dipterocarpus, and Dryobalanops. These REVs have shown a wide range of bioactivities. Pharmacological studies have mainly focused on potential efficacy on tumors, bacteria, Alzheimer’s disease, cardiovascular diseases, and others. The information updated in this review might assist further research and development of novel REVs as potential therapeutic agents.

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Section: Phytochemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers

Shen

Zhou

et al. 2017

Molecules

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“…Stilbenes have been widely studied for their medicinal properties . In contrast, while some are known as phytoalexins, studies on their pesticidal activity have been sparse.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 3,5‐Dimethoxystilbene Analogs

Weng

Alı

Estep

et al. 2016

Chemistry & Biodiversity

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In our continuing effort to discover natural product-based pest management agents, derivatives of 3,5-dimethoxystilbene were synthesized yielding 27 new and six known compounds. Compounds 11 and 12 showed strong Aedes aegypti larvicidal activity (LC 45.31 and 49.93 μm, respectively). Furthermore, 11 and 12 exhibited high effectiveness against larvae of pesticide-susceptible and pyrethroid-resistant strains of Ae. aegypti; activity against the adult mosquitoes was low. Compounds 6f, 6g, and 6i at either 83.3 or 166.7 μg/ml reduced the mobility of second-stage juveniles (J2) of the root-knot nematode (Meloidogyne incognita) that hatched from eggs immersed in the test compounds for 7 days. However, there was little or no effect on J2 placed directly into these compounds, and none of the analogs suppressed M. incognita egg hatch. The compounds were tested for inhibition of some agriculturally important fungi; 6a, 7a, and 7e demonstrated strong inhibition of Colletotrichum species. Activity of the stilbenes against some human pathogens was also explored; 11, 12, and 16 showed moderate inhibitory activity against Cryptococcus neoformans, Staphylococcus aureus, methicillin-resistant S. aureus, and Mycobacterium intracellulare. Except for 11 and 12, which were active against mosquito larvae and some human pathogens, no single analog demonstrated activity in all the tests, indicating specific activities. Synthesis of the analogs and structure-activity relationships are discussed.

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“…Resveratrol polymerization leads to an extensive structural diversity. Indeed more than a hundred of naturally occurring stilbenes have been isolated and identified from different sources (Niesen, Hessler, & Seeram, 2013). The stilbene derivatives identified in grape (in various parts of the plant, such as leaves, roots, clusters, and stems) by accurate MS, include monomers, glucoside derivatives, dimers (viniferins), trimmers, and tetramers (Flamini, Mattivi, De Rosso, Arapitsas, & Bavaresco, 2013) therefore a winemaking technique able to enrich wine with different stilbenoids would be very attractive for winemakers.…”

mentioning

confidence: 99%

Effects of ageing on stilbenes and biogenic amines in red grape winemaking with stem contact maceration

Basile

Alba

Suriano

et al. 2017

J Food Process Preserv

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Stem contact maceration is a technique used in red winemaking for wines poor of phenolic constituents (tannins) in order to improve organoleptic characteristics and ensure color stability over time. This article investigates how the presence of different amounts of de‐stemmed bunches affects stilbenoids, known for their nutraceutical properties and biogenic amines (BAs), known for their adverse physiological and toxicological effects, at racking and after 24 months of storage in Primitivo wine. Stilbenes found in Primitivo were not influenced by the stems during maceration/fermentation. The ageing period resulted in isomerization phenomena of trans forms of piceid and resveratrol to the corresponding cis forms. The presence of stems during the winemaking did not induced the production or enhanced BAs content. Therefore, this enological practice does not represent a limit in terms of food safety and product quality. Practical applications Red wines poor in proanthocyanidins are subjected to color loss and decrease of organoleptic properties over time. Stem contact maceration is a technique used in red winemaking in order to enforce structure and stabilize color over time. Since food safety and product quality are of paramount importance, this study for the first time examines the presence of dangerous biogenic amines (BAs) and potent antioxidant stilbenoids throughout the production and aging of red wines produced with this technique. Results may benefit the winemaking industry and researchers who are striving to improve the processing and marketing of red wine.

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Beyond resveratrol: A review of natural stilbenoids identified from 2009–2013

Cited by 54 publications

References 46 publications

Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers

Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers

Synthesis and Biological Evaluation of 3,5‐Dimethoxystilbene Analogs

Effects of ageing on stilbenes and biogenic amines in red grape winemaking with stem contact maceration

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