Occurrence of C-Glucoside of Resveratrol Oligomers in Hopea parviflora

Abe, Naohito; Ito, Tetsuro; Oyama, Masayoshi; Sawa, Ryûichi; Takahashi, Yoshikazu; Chelladurai, Veliah; Iinuma, Munekazu

doi:10.1248/cpb.59.239

Cited by 16 publications

(12 citation statements)

References 22 publications

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“…Resveratrol oligomers are formed by the polymerization of two or more resveratrol units to generate dimers, trimers, tetramers, and even more complex derivatives. The biogenesis of these derivatives is still not completely understood, but it appears to involve the coupling of regioisomeric nodes that generate diverse resveratrol dimeric frameworks that can further undergo various regiodivergent reactions to generate more complex structures …”

Section: Introductionmentioning

confidence: 99%

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Espinoza

Inaoka

2017

Annals of the New York Academy of Sciences

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Resveratrol has been extensively studied to investigate its biological effects, including its chemopreventive potential against cancer. Over the past decade, various resveratrol oligomers, both naturally occurring and synthetic, have been described. These resveratrol oligomers result from the polymerization of two or more resveratrol units to form dimers, trimers, tetramers, or even more complex derivatives. Some oligomers appear to have antitumor activities that are similar or superior to monomeric resveratrol. In this review, we discuss resveratrol oligomers with anticancer potential, with emphasis on well-characterized compounds, such as the dimer gnetin-C and other oligomers from Gnetum gnemon, whose safety, pharmacokinetic, and biological activities have been studied in humans.

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Section: Introductionmentioning

confidence: 99%

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Espinoza

Inaoka

2017

Annals of the New York Academy of Sciences

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“…The similar biosynthetic machinery responsible for the production of a resveratrol pentamer glucoside is hopeaside A (61) (Fig. 7) [56]. 2-C-β-glucopyranosyl resveratrol (4) proceeds by epoxidation; it is prone to attack by nucleophiles, such as the electron-rich arenes of 37, which produces 61.…”

Section: Highly Condensed Romentioning

confidence: 99%

Resveratrol oligomer structure in Dipterocarpaceaeous plants

Ito

2020

J Nat Med

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Oligostilbenoids are a group of natural products derived from the oxidative coupling of C6–C2–C6 units found in some plant families. A structurally diverse chemical pool is produced after the successive regioselective and stereoselective oligomerization of resveratrol. This review describes the current status and knowledge of the structure of resveratrol oligomers (ROs) in Dipterocarpaceaeous plants (DPs). Beginning with the recently validated formation of ROs in DPs, each downstream conversion is described from the perspective of the resveratrol coupling mode. Particular emphasis is placed upon the regioselectivity of monomer- and dimer-derived radical–radical coupling processes, which are responsible for producing dimers, trimers, and tetramers with various cyclic frame skeletons, as well as related processes that result in highly condensed scaffolds, such as hexamers and octamers. Trimers in oxidized, dearomatized, and rearranged forms are also summarized, as well as the biogenic relationship between the compounds. Furthermore, emphasis is placed on the O- and C-glucosides of ROs, as well as on the hetero-coupled ROs. In addition, several stereoisomers that originate from asymmetric carbons and the stereochemistry with respect to the conformation due to the chiral axis are described. Besides, NMR spectroscopic properties such as coalescence and anisotropy are briefly described. Approaches to determine absolute configuration are also summarized.

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“…Abe et al [39] isolated four new C-glycosylated structures from Hopea parviflora, namely, 2 pentamers, a trimer, and a dimer. These compounds have been named hopeasides A-D (Fig.…”

Section: C-glycosylated Stilbenesmentioning

confidence: 99%

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

Niesen

Hessler

Seeram

2013

Journal of Berry Research

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Polyphenols constitute a large chemical class of phytochemicals among which the stilbenoid sub-class has attracted significant attention due to their elaborate structural diversity and biological activities. Resveratrol, a well-known stilbene, has been extensively studied due to its wide range of biological activities and occurrence in plant foods, including grape and some berries. Apart from the intact resveratrol molecule and closely related analogs, this compound can be regarded as a monomer which occurs as a primary building block for subsequent polymerization which leads to extensive structural diversity. Consequently, stilbenoids exhibit a vast array of polymerization and oligomeric construction, with over 60 such naturally occurring stilbenes being isolated and identified in the last five years alone, adding to the hundreds which are already known to date. This review updates the literature on natural stilbenoids which have been isolated and identified since 2009 and discusses the biological activities of this sub-class of bioactive polyphenols as a whole.

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Occurrence of C-Glucoside of Resveratrol Oligomers in Hopea parviflora

Cited by 16 publications

References 22 publications

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential

Resveratrol oligomer structure in Dipterocarpaceaeous plants

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

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