Regiospecific synthesis, anti-inflammatory and anticancer evaluation of novel 3,5-disubstituted isoxazoles from the natural maslinic and oleanolic acids

Chouaïb, Karim; Romdhane, Anis; Delemasure, Stéphanie; Dutartre, Patrick; Elie, Nicolas; Touboul, David; Jannet, Hichem Ben; Hamza, M’hamed Ali

doi:10.1016/j.indcrop.2016.03.024

Cited by 42 publications

(38 citation statements)

References 32 publications

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“…Maslinic acid (MA) is a pentacyclic triterpene derived from olives that has produced no pharmacological problems for elderly people. Its pharmacological functions include anti-inflammatory, anti-tumor and anti-oxidative properties, among others [ 9 , 10 ]. Thus, the anti-inflammatory activity of MA may relieve pain in patients with knee OA.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of maslinic acid with whole-body vibration training in elderly women with knee osteoarthritis

et al. 2018

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PurposeMaslinic acid (MA) is a component derived from a natural olive-based extract known to have pharmacological functions that include suppressing inflammation. This study examined how MA, in conjunction with whole-body vibration training (WBVT), can improve knee and muscle function in elderly women with knee osteoarthritis (OA).MethodsThe study was a double-blinded, placebo-controlled, randomized intervention study that enrolled individuals with knee pain. Participants were 26 females aged 65–85 years with knee OA. They performed WBVT and ingested either 16.7 mg of MA or a placebo daily for 20 weeks. We compared the effect of WBVT with placebo (WBVT/P) and WBVT with MA (WBVT/MA) in participants with various degrees of knee OA (Kellgren and Lawrence (K-L) grade) using the Japanese Orthopaedic Association (JOA) score and isokinetic dynamometer measurements to evaluate knee and muscle function with two-way ANOVA.ResultsBased on the results of two-way ANOVA analysis of muscle function measurements, there was significant interaction (time × group) (P = 0.03) in the “isokinetic extension peak torque” domain for severe OA (K-L grade ≥ 3). The simple main effect of time in the WBVT/MA group (P = 0.04) contributed to this interaction. The JOA score for WBVT/MA supported the main effect of group as having a significant correlation in the “pain on walking” (P = 0.04) and “range of motion” (P < 0.01) domains. Participants with severe knee OA in the WBVT/MA group improved in these domains, whereas the WBVT/P group had few positive results.ConclusionsParticipants with severe OA who ingested MA in conjunction with WBVT improved their knee and muscle function. This study suggests that ingesting the anti-inflammatory supplement MA while participating in WBVT, elderly women can reduce knee OA and improve their knee muscle strength.

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Section: Introductionmentioning

confidence: 99%

Evaluation of maslinic acid with whole-body vibration training in elderly women with knee osteoarthritis

et al. 2018

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“…On the other hand, it seems that the replacement of the halogen group (ring A) from fluorine (compounds 3f and 3d) to bromine (compounds 3e and 3c) reduced the potency by nearly half, meaning that the nature of the halogen attached to ring A at the 6-position and hence the mesomerism effect exerted by each one could be a key factor for cytotoxic activity. 30,31 These results clearly indicate the importance of halogens as substituents in 3HFs to get interesting cytotoxic activity. The findings above led us to investigate the influence of halogen substituents on the biological properties of this class of flavonoids.…”

Section: Scheme 2 Synthesis Of Compounds 6a-6fmentioning

confidence: 90%

New flavonoid glycosides conjugates: synthesis, characterization, and evaluationof their cytotoxic activities

Souiei¹,

Garah²,

Belkacem³

et al. 2019

Turk J Chem

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A series of novel halogenated 3-hydroxyflavones (3HFs) were prepared by reacting halogenated hydroxyacetophenones with the appropriate aromatic aldehyde. Glycosylation of 3HFs with acetobromoglucose and deprotection of the acetyl protective groups afforded the desired 3-O -flavonoids glycosides in satisfactory yields. All the prepared compounds were tested for their cytotoxic activity against HCT-116, MCF-7, and OVCAR-3 human cancer cell lines.The 3HFs exhibited higher cytotoxic activities compared with the glycosylated flavonoids. Overall, the structure-activity relationship study showed that the introduction of glycoside moiety at the C-3 OH position does not improve the bioactivity.Recent interest in the O -glycoside and/or C -glycoside forms has been stimulated by the potential health benefits arising from the hugely diverse bioactivities of these flavonoid derivatives. The specific properties of these flavonoid derivatives might be due to the presence of aromatic and glycoside moieties and many hydroxyl groups. However, the dietary flavonoid C -glycosides have received less attention than their corresponding O -glycosides. 7 Among the flavonoid derivatives of pharmacological and biological interest, the 3-hydroxyflavones (3HFs) or flavonols constitute a major class as they are endowed with various biological activities such as antiinflammatory, 8 antiacetylcholinesterase, 9 antioxidant, 10,11 anticancer, 12,13 antidepressant, 14,15 antidiabetic, 16 antimicrobial, 17 antihypertensive, 18 anti-HIV, 19 and antiallergic. 20 On the other hand, it has been found that almost all the dietary flavonoids, especially flavonols, exist in nature as α -or β -glycoside forms such as flavonoid glucosides, rhamnosides, galactosides, arabinosides, and rutinosides. 3,21 As a special type of flavonoid O -glycoside, flavonol * Correspondence: hichem.bjannet@gmail.com This work is licensed under a Creative Commons Attribution 4.0 International License.O -glycosides are often found in nature and so far more than 1500 of them have been isolated and characterized, mostly from higher plants, 22 and the majority of these compounds ( ∼80%) have a sugar linkage at the 3-OH.Moreover, flavonol O -glycosides have been proven to have promising pharmaceutical activities. 23 The high rate of occurrence and the importance of flavonol glycosides have attracted attention to synthetic studies of this group of natural products.It was further reported that natural flavonols are frequently substituted at variable positions, mainly by hydroxyl, methoxyl, isoprenyl, and glycosyl groups, and it was also thought that biological activities of flavonols are due to the presence of these substituents. 24 Nevertheless, it has been demonstrated that halogenated organic derivatives also exhibit significant biological activities. 25Since halogenated substituted flavonols are not found in nature and since glycosylation of flavonoids improves their solubility, stability, and bioavailability relative to flavonoid aglycones, and as a part of our general program in ...

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“…The copper‐catalyzed MW‐assisted 1,3‐DC reactions between the alkyne derivatives 82 a and 82 b obtained from the natural pentacyclic triterpenoid maslinic ( 81 b ) and oleanolic acids ( 81 a ) and a series of aryl NOs, afforded regiospecifically the expected 3,5‐disubstituted isoxazoles 83 a and 83 b in almost quantitative yields (Scheme ) . The reaction times were shorter than those reported in the literature (max 10 min instead of hours and days).…”

Section: Nitrile Oxide Cycloadditions Under Microwave (Mw) Activationmentioning

confidence: 95%

1,3‐Dipolar Cycloaddition Reactions of Nitrile Oxides under “Non‐Conventional” Conditions: Green Solvents, Irradiation, and Continuous Flow

Plumet

2020

ChemPlusChem

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The 1,3‐dipolar cycloaddition reactions (DCs) of nitrile oxides (NOs) to alkenes and alkynes are useful methods for the synthesis of 2‐isoxazolines and isoxazoles respectively, which are important classes of heterocyclic compounds in organic and medicinal chemistry. Most of these reactions are carried out in organic solvents and under thermal activation. Nevertheless the use of supercritical carbon dioxide (scCO2) and ionic liquids (Ils) as alternative solvents and the application of microwave (MW) and ultrasound (US) as alternative activation procedures have evident advantages from the “Green Chemistry” point of view. The critical discussion on the applications of these “unconventional” activation methods and reaction conditions in the 1,3‐DCs of NOs is the objective of the present Review.

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Regiospecific synthesis, anti-inflammatory and anticancer evaluation of novel 3,5-disubstituted isoxazoles from the natural maslinic and oleanolic acids

Cited by 42 publications

References 32 publications

Evaluation of maslinic acid with whole-body vibration training in elderly women with knee osteoarthritis

Evaluation of maslinic acid with whole-body vibration training in elderly women with knee osteoarthritis

New flavonoid glycosides conjugates: synthesis, characterization, and evaluationof their cytotoxic activities

1,3‐Dipolar Cycloaddition Reactions of Nitrile Oxides under “Non‐Conventional” Conditions: Green Solvents, Irradiation, and Continuous Flow

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