Flavonoids: An Outstanding Structural Core for the Inhibition of Xanthine Oxidase Enzyme

Mathew, Bijo; Suresh, Jerad; Mathew, Githa Elizabeth; Rasheed, Sherin A.; Vilapurathu, Jobin Kunjumon; Jayaraj, P.

doi:10.2174/1573408011666150730204108

Cited by 24 publications

(12 citation statements)

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“…The decrease of uric acid levels in serum could be due to the presence of the compounds quercetin, kaempferol and rutin in PR-ME extract as detected in LCMS/MS. In fact, kaempferol, quercetin and rutin were capable of reducing the accumulation of purine metabolites in blood following PO-induction rats as reported by several researchers [ 14 , 51 , 52 , 53 ].…”

Section: Discussionmentioning

confidence: 79%

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Isa¹,

Ablat

Mohamad

2018

Molecules

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Plumeria rubra Linn of the family Apocynaceae is locally known in Malaysia as “Kemboja”. It has been used by local traditional medicine practitioners for the treatment of arthritis-related disease. The LCMS/MS analysis of the methanol extract of flowers (PR-ME) showed that it contains 3-O-caffeyolquinic acid, 5-caffeoquinic acid, 1,3-dicaffeoquinic acid, chlorogenic acid, citric acid, 3,3-di-O-methylellagic acid, kaempferol-3-O-glucoside, kaempferol-3-rutinoside, kaempferol, quercetin 3-O-α-l-arabinopyranoside, quercetin, quinic acid and rutin. The flower PR-ME contained high amounts of phenol and flavonoid at 184.632 mg GAE/g and 203.2.2 mg QE/g, respectively. It also exhibited the highest DPPH, FRAP, metal chelating, hydrogen peroxide, nitric oxide superoxide radical scavenging activity. Similarly, the XO inhibitory activity in vitro assay possesses the highest inhibition effects at an IC50 = 23.91 μg/mL. There was no mortality or signs of toxicity in rats at a dose of 4 g/kg body weight. The administration of the flower PR-ME at doses of 400 mg/kg to the rats significantly reduced serum uric acid 43.77%. Similarly, the XO activity in the liver was significantly inhibited by flower PR-ME at doses of 400 mg/kg. These results confirm that the flower PR-ME of P. rubra contains active phytochemical compounds as detected in LCMS/MS that contribute to the inhibition of XO activity in vitro and in vivo in reducing acid uric level in serum and simultaneously scavenging the free radical to reduce the oxidative stress.

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Section: Discussionmentioning

confidence: 79%

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Isa¹,

Ablat

Mohamad

2018

Molecules

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“…Moreover, these with two hydroxyl groups located at ortho - position on ring B at C(3) and C(4), showed stronger activity than those with the equivalent substitutes but located at the meta - position ( 5 > 6 ≫ 4 ). It is explained based on molar refractivity parameter; the high polarizability will enhance the attractive dispersion interactions with an aromatic residue of enzyme binding site through π–π stacking interactions (Costantino et al 1996 ; Mathew et al 2015 ). However, when the C(4) hydroxyl was methylated, the above conclusion is reversed.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of chalcone derivatives as potential non-purine xanthine oxidase inhibitors

et al. 2016

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BackgroundBased on some previous research, the chalcone derivatives exhibited potent xanthine oxidase inhibitory activity, e.g. sappanchalcone (7), with IC50 value of 3.9 μM, was isolated from Caesalpinia sappan. Therefore, objectives of this research are design and synthesis of 7 and other chalcone derivatives by Claisen–Schmidt condensation and then evaluate their XO inhibitory activity.ResultsFifteen chalcone derivatives were synthesized by Claisen–Schmidt condensation, and were evaluated for XO inhibitory activity. Nine out of 15 synthetic chalcones showed inhibitory activity (3; 5–8; 10–13). Sappanchalcone derivatives (11) (IC50, 2.5 μM) and a novel chalcone (13) (IC50, 2.4 μM) displayed strong xanthine oxidase inhibitory activity that is comparable to allopurinol (IC50, 2.5 μM). The structure–activity relationship of these chalcone derivatives was also presented.ConclusionsIt is the first research on synthesis sappanchalcone (7) by Claisen–Schmidt condensation. The overall yield of this procedure was 6.6 %, higher than that of reported procedure (4 %). Design, synthesis, and evaluation of chalcone derivatives were carried out. This result suggests that the chalcone derivative can be used as potential non-purine XO inhibitors.Graphical abstractThe chalcone derivatives as potential non-purine xanthine oxidase inhibitors Electronic supplementary materialThe online version of this article (doi:10.1186/s40064-016-3485-6) contains supplementary material, which is available to authorized users.

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“…Among the two isoforms of monoamine oxidase A and B, MAO−B is responsible for oxidative deamination of various biogenic and xenobiotic amines . This resulted the production of reactive oxygen species (ROS) as the neurotoxic by‐product which leads to the neuronal damage .…”

Section: Introductionmentioning

confidence: 99%

Ethoxylated Head of Chalcones as a New Class of Multi‐Targeted MAO Inhibitors

et al. 2019

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A series of eleven ethoxysubstituted chalcones (E1-E11) were synthesized and investigated for their inhibitory potential towards human recombinant monoamine oxidase A and B (hMAOÀ A and hMAOÀ B, respectively) and acetylcholinesterase (AChE). IC 50 values of 4.63 � 0.15 and 0.053 � 0.003 μM were obtained for MAOÀ A and MAOÀ B, respectively, by the most interesting compound (2E)-1-(4-ethoxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (E7), and it was characterized by a high selectivity index (SI = 87.4) for MAOÀ B. Inhibitions by E7 against MAOÀ A and MAOÀ B were recovered (75.9 and 74.5%, respectively) to near the levels of reversible references (77.1 and 77.4%, respectively). The inhibition modes of E7 for MAOÀ A and MAOÀ B were competitive with K i values of 2.65 � 0.064 and 0.011 � 0.0011 μM, respectively. Compounds (2E)-1-(4ethoxyphenyl)-3-(4-ethylphenyl) prop-2-en-1-one (E10) and (2E)-1-(4-ethoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (E11) showed good inhibitions against AChE with IC 50 values of 2.86 � 0.041 and 3.23 � 0.0073 μM, respectively. A combined molecular docking/MM-GBSA approach was used that employed quantum mechanics (QM) partial charges; this technique revealed the molecular rationale behind the observed MAOÀ B selectivity for this molecular series. Taken together, these results indicate that E7 is a potent, selective and reversible competitive inhibitor of MAOÀ B with moderately potent AChE inhibitory activity that has potential as a multitargeting drug

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Flavonoids: An Outstanding Structural Core for the Inhibition of Xanthine Oxidase Enzyme

Cited by 24 publications

References 0 publications

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Design and synthesis of chalcone derivatives as potential non-purine xanthine oxidase inhibitors

Ethoxylated Head of Chalcones as a New Class of Multi‐Targeted MAO Inhibitors

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