Regio‐ and Diastereo‐Selective Biomimetic Synthesis of (±)‐<i>ϵ</i>‐Viniferin by NIS and Resveratrol

D’Orsi, Rosarita; Morrongiello, Francesca; Laurita, Teresa; Funicello, Maria; Lupattelli, Paolo; Chiummiento, Lucia

doi:10.1002/slct.202101678

Cited by 3 publications

(3 citation statements)

References 30 publications

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“…It is remarkable that in the 13 C spectrum, the effect of an iodine substituent is accompanied by a characteristic diamagnetic shift, as shown by the δC-4 signal at 73.8 ppm ( Figure S21 ). Compound 3 was previously reported by Lee et al [ 25 , 26 ] as products formed from the halogenation of resveratrol.…”

Section: Resultsmentioning

confidence: 95%

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

et al. 2022

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Resveratrol is a well-known natural polyphenol with a plethora of pharmacological activities. As a potent antioxidant, resveratrol is highly oxidizable and readily reacts with reactive oxygen species (ROS). Such a reaction not only leads to a decrease in ROS levels in a biological environment but may also generate a wide range of metabolites with altered bioactivities. Inspired by this notion, in the current study, our aim was to take a diversity-oriented chemical approach to study the chemical space of oxidized resveratrol metabolites. Chemical oxidation of resveratrol and a bioactivity-guided isolation strategy using xanthine oxidase (XO) and radical scavenging activities led to the isolation of a diverse group of compounds, including a chlorine-substituted compound (2), two iodine-substituted compounds (3 and 4), two viniferins (5 and 6), an ethoxy-substituted compound (7), and two ethoxy-substitute,0d dimers (8 and 9). Compounds 4, 7, 8, and 9 are reported here for the first time. All compounds without ethoxy substitution exerted stronger XO inhibition than their parent compound, resveratrol. By enzyme kinetic and in silico docking studies, compounds 2 and 4 were identified as potent competitive inhibitors of the enzyme, while compound 2 and the viniferins acted as mixed-type inhibitors. Further, compounds 2 and 9 had better DPPH scavenging activity and oxygen radical absorbing capacity than resveratrol. Our results suggest that the antioxidant activity of resveratrol is modulated by the effect of a cascade of chemically stable oxidized metabolites, several of which have significantly altered target specificity as compared to their parent compound.

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Section: Resultsmentioning

confidence: 95%

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

et al. 2022

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“…S21). Compound 3 was previously reported by Lee et al [25,26] as products formed from the halogenation of resveratrol.…”

Section: Structure Elucidation Of the Isolated Compoundsmentioning

confidence: 87%

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

Agbadua¹,

Kúsz²,

Berkecz³

et al. 2022

Preprint

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Resveratrol is a well-known natural polyphenol with a plethora of pharmacological activities. As a potent antioxidant, resveratrol is highly oxidizable, and readily reacts with reactive oxygen species (ROS). Such a reaction not only leads to a decrease in ROS levels in a biological environ-ment but may also generate a wide range of metabolites with altered bioactivities. Inspired by this notion, in the current study, our aim was to take a diversity-oriented chemical approach to study the chemical space of oxidized resveratrol metabolites. Chemical oxidation of resveratrol and a bioactivity-guided isolation strategy using xanthine oxidase (XO) and radical scavenging activities led to the isolation of a diverse group of compounds, including a chlorine-substituted compound (2), two iodine-substituted compounds (3 and 4), two viniferins (5 and 6), an eth-oxy-substituted compound (7) two ethoxy-substituted dimers (8 and 9). Compounds 4, 7, 8 and 9 are reported here for the first time. All compounds without ethoxy-substitution exerted stronger XO inhibition than their parent compound, resveratrol. By enzyme kinetic and in silico docking studies compounds 2, 3 and 4 were identified as potent competitive inhibitors of the enzyme while the viniferins acted as mixed-type inhibitors. Further, compounds 2 and 9 had better DPPH scavenging activity and oxygen radical absorbing capacity than resveratrol. Our results suggest that the antioxidant activity of resveratrol is modulated by the effect of a cascade of chemically stable oxidized metabolites, several of which have significantly altered target specificity as compared to their parent compound.

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“…Obtusafuran (11) is a simple dihydrobenzofuran natural product isolated from numerous Dalbergia species like Dalbergia louveli and acts as an inductor of the quinone reductase, an anticarcinogenic marker enzyme. [32,33] > Some compounds, such as (+)-ɛ-Viniferin ( 12), [34,35] Maximol A (δ-Viniferin) (13), [36] and Gnetin C ( 14), [37][38][39] isolated from Vitis thunbergia, [40] and Vitis vinifera, [41] showed free radical scavenging and anti-platelet aggregation activities. (+)-ɛ-Viniferin has also been demonstrated to have anti-inflammatory, anti-carcinogenic, and car-dioprotective properties in vitro.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

et al. 2022

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The 2,3-dihydrobenzofuran heterocyclic systems are found in various biologically active natural and pharmaceutical products of biological relevance such as Phalarine, Rocaglamide, and Furaquinocin A. The interest in the study of 2,3-dihydrobenzofurans is constantly increasing because of their numerous biological properties such as anti-tumor, anticancer, anti-tubercular, and anti-malarial activities. Different methods have been established towards the synthesis of 2,3dihydrobenzofurans involved via intra-and inter-molecular reactions. Besides, the 1,3-dihydroisobenzofuran structure has been identified as a fundamental nucleus in many natural products, bioactive compounds, and functional molecules (e. g., Pestacin, Isopestacin, Citalopram, Xylarinol B, Matriisobenzofuran, Thunberginol F7-O-β-D-glucopyranoside). On the other hand, 1,3-disubstituted isobenzofurans are powerful structural motifs with a wide range of biological activities, like anti-inflammatory, anti-histaminic, and anti-HIV. In the last few years, a decent number of diligent synthetic approaches have been demonstrated toward synthesizing 1,3-disubstituted isobenzofurans. This review focuses on the effective synthetic routes developed to construct 2,3-dihydrobenzofurans and 1,3-dihydroisobenzofurans and their applications in recent years.

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Regio‐ and Diastereo‐Selective Biomimetic Synthesis of (±)‐ϵ‐Viniferin by NIS and Resveratrol

Cited by 3 publications

References 30 publications

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

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