Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers

Teng, Yuou; Li, Xuzhe; Yang, Ke; Li, Xuehui; Zhang, Zijun; Wang, Luyao; Deng, Zhijie; Song, Binbin; Yan, Zhihong; Zhang, Yongmin; Lu, Kui; Yu, Peng

doi:10.1016/j.ejmech.2016.09.024

Cited by 20 publications

(20 citation statements)

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“…The FRAP value of chalcone dimer 44 was calculated from the calibration curve derived from dilutions of a vitamin C standard, measuring the decrease in absorption of the complex at 660 nm. Compound 44 exhibited better activity in the FRAP assay than the positive control, gallic acid (648.44 and 531.02 mg/mM, equivalent amounts of vitamin C) [29].…”

Section: Ferric Reducing Antioxidant Power (Frap) Methodsmentioning

confidence: 91%

“…The other tested compounds showed comparable or weaker ABTS scavenger properties than 1 (>200 µM TEAC/g) [27]. The ABTS radical scavenging profile of the chalcone desmethylxanthohumol (3) was expressed as the half-maximal effective concentration (EC 50 ), presenting an EC 50 of 0.54 ± 0.09 µM, slightly less than that of gallic acid (0.35 ± 0.01 µM) [29].…”

Section: Abts Radical Cation Scavenging Activity (Teac Method)mentioning

confidence: 97%

“…A limited number of derivatives can be obtained from Moraceae [18][19][20], Fabaceae [21][22][23] and Asteraceae [24] families. More than half of the chalcones, mainly derivatives of xanthohumol, were prepared by synthesis [12][13][14][25][26][27][28][29] (compounds 1-44, Table 1). To refer that Popoola et al identified isoxanthohumol isolated from the aerial part of Helichrysum teretifolium as a chalcone derivative 21 [24] while the remaining literature classify isoxanthohumol as a flavanone derivative 102 [12][13][14].…”

Section: Natural Occurrence and Structural Variation Of Prenylflavonomentioning

confidence: 99%

“…To refer that Popoola et al identified isoxanthohumol isolated from the aerial part of Helichrysum teretifolium as a chalcone derivative 21 [24] while the remaining literature classify isoxanthohumol as a flavanone derivative 102 [12][13][14]. 3-methoxyxanthohumol synthesis [28] [29] Most of the known derivatives are prenylated on the A-ring (Table 2), except licochalcone A (17) that has an 1,1-dimethylallyl unit at C-5 of B-ring ( Figure 2). Among the former ones, 3 -prenyl substitution is the most abundant side attachment, being most of these derivatives also hydroxylated at positions 2 > 4 > 4 and methylated at positions 6 > 4 > 2 ( Table 2).…”

Section: Natural Occurrence and Structural Variation Of Prenylflavonomentioning

confidence: 99%

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The Antioxidant Activity of Prenylflavonoids

Santos

Silva

2020

Molecules

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Prenylated flavonoids combine the flavonoid moiety and the lipophilic prenyl side-chain. A great number of derivatives belonging to the class of chalcones, flavones, flavanones, isoflavones and other complex structures possessing different prenylation patterns have been studied in the past two decades for their potential as antioxidant agents. In this review, current knowledge on the natural occurrence and structural characteristics of both natural and synthetic derivatives was compiled. An exhaustive survey on the methods used to evaluate the antioxidant potential of these prenylflavonoids and the main results obtained were also presented and discussed. Whenever possible, structure-activity relationships were explored.

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Section: Ferric Reducing Antioxidant Power (Frap) Methodsmentioning

confidence: 91%

Section: Abts Radical Cation Scavenging Activity (Teac Method)mentioning

confidence: 97%

Section: Natural Occurrence and Structural Variation Of Prenylflavonomentioning

confidence: 99%

Section: Natural Occurrence and Structural Variation Of Prenylflavonomentioning

confidence: 99%

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The Antioxidant Activity of Prenylflavonoids

Santos

Silva

2020

Molecules

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“…The chalcone was found as a promising anti-ischemic stroke drug candidate, providing novel dual-antioxidant mechanism strategies and concepts for oxidative stress-related disease treatment [52]. The prenylated chalcones (51) were reported for good antioxidant activity [53]. Figure 6 represents the structures of antioxidant chalcones.…”

Section: Antioxidant Chalconesmentioning

confidence: 99%

Biological Role of Chalcones in Medicinal Chemistry

Tekale¹,

Mashele²,

Pooe³

et al. 2020

Vector-Borne Diseases - Recent Developments in Epidemiology and Control

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Chalcones are promising synthons and bioactive scaffolds of great medicinal interest due to their numerous pharmacological and biological activities. They are well recognized to possess antimicrobial, anticancer, antitubercular, antioxidant, anti-inflammatory, antileishmanial, and other significant biological activities. This chapter highlights recent updates and applications of chalcones as biologically, pharmacologically, and medicinally important entities.

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Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

Yılmaz

Menteşe

Sökmen

2020

Journal of Heterocyclic Chem

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A new series of 1,3‐benzoxazol‐2(3H)‐one hybrid compounds, including coumarin, isatin 1,3,4‐triazole and 1,3,4‐thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti‐urease properties. The synthesized benzoxazole‐coumarin (6a–e) and benzoxazole‐isatin (10a–c) hybrids showed remarkable urease inhibitory activities with IC50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC50 of standard thiourea is 0.5027 ± 0.0293. The synthesized benzoxazole‐triazole (8a–c) and benzoxazole‐thiadiazole (9a–c) hybrids showed similar urease inhibitory activities with IC50 (μM), ranging from 0.3861 ± 0.0379 to 0.5126 ± 0.0345. The antioxidant activity of the synthesized compounds was evaluated for their antioxidant activities, such as reducing power and ABTS (2,2′‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulphonic acid) diammonium salt) radical scavenging. The results of ABTS radical scavenging activities of some of the synthesized molecules showed higher activities than standard Trolox, SC50 (μM) = 213.04 ± 18.12. One benzoxazole‐coumarin (6f), two benzoxazole‐isothiocyanate (7b, 7c), and two benzoxazole‐triazole (8b, 8c) derivatives showed higher activities (SC50 (μM) values, 82.07 ± 10.34, 120.19 ± 7.30, 104.58 ± 10.55, 153.26 ± 7.14, and 144.82 ± 10.68, respectively) than standard Trolox, (SC50 (μM) = 213.04 ± 18.12).

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Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers

Cited by 20 publications

References 28 publications

The Antioxidant Activity of Prenylflavonoids

The Antioxidant Activity of Prenylflavonoids

Biological Role of Chalcones in Medicinal Chemistry

Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

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