Synthesis and highly potent hypolipidemic activity of alpha-asarone- and fibrate-based 2-acyl and 2-alkyl phenols as HMG-CoA reductase inhibitors

Mendieta‐Moctezuma, Aarón; Jiménez, Fabiola; Garduño‐Siciliano, Leticia; Mojica-Villegas, Angélica; Rosales-Acosta, Blanca; Villa‐Tanaca, Lourdes; Chamorro-Cevallos, Germán; Medina-Franco, José L.; Meurice, Nathalie; Gutiérrez, Rsuini U.; Montiel, Luisa E.; Cruz, María del Carmen; Tamariz, Joaquı́n

doi:10.1016/j.bmc.2014.09.022

Cited by 26 publications

(11 citation statements)

References 72 publications

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“…Based on 1 H- 1 H COSY and HMBC correlations, compound 3 was suggested to be a known compound 1-(2′-hydroxy- 4′, 5′-dimethoxyphenyl) propan-1-one. The structure was confirmed by comparing 1 H-NMR and 13 C-NMR spectral data to the data reported by Mendieta and co-workers [17].…”

Section: Resultssupporting

confidence: 71%

Potential in vitro anti-allergic, anti-inflammatory and cytotoxic activities of ethanolic extract of Baliospermum montanum root, its major components and a validated HPLC method

Pipatrattanaseree

Itharat

Mukkasombut

et al. 2019

BMC Complement Altern Med

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BackgroundThe root of Baliospermum montanum has been used as an ingredient of traditional Thai medicines for the treatments of several diseases including itching eczema, muscle and joint inflammation, and cancer. Few studies have been done on phytochemical components of this root. In this study, we isolated major compounds of the crude ethanolic extract of B. montanum root and developed and validated a high performance liquid chromatographic (HPLC) method for the determination of its major components. We then investigated anti-allergic, anti-inflammatory and cytotoxic activities of the extract.MethodsThe aims of this study were to investigate in vitro activities including inhibitory effect of β-hexosaminidase released from RBL-2H3 cells, inhibition of nitric oxide (NO) production from RAW 264.7 cells and cytotoxic activity against cancerous liver cell lines (HepG2 and KKU M156) by using sulforhodamine B (SRB) assay. Isolation of major components was conducted by using column chromatographic method. Isolated major compounds were analyzed by using high performance liquid chromatography (HPLC).ResultsThe crude extract exhibited the highest cytotoxic activity, with IC50 less than 1 μg/mL, while its anti-allergy and anti-inflammation were also potent with IC50 less than 6 μg/mL. Three propiophenones isolated from B. montanum root exhibited moderate cytotoxic activities (IC50 > 20 μg/mL). Two of the propiophenones found were major components that can be detected by HPLC. The developed and validated HPLC method showed good accuracy, precision, and linearity.ConclusionThe results of this study suggested that ethanolic extract of of B.montanum root can be a potential source of anti-allergy, anti-inflammation, and anti-cancer compounds. The isolated compounds can serve as markers when B. montanum is used in herbal remedies but not as overall responsive markers. The HPLC method developed may be useful for quality control in the production of the extract and for further formulation developments. However, investigation of several associated biological activities is necessary before the development can proceed further. Minor active compounds should be isolated and a more sensitive analytical method should be developed to detail the key responsive components of the ethanolic extract of B. montanum root.Electronic supplementary materialThe online version of this article (10.1186/s12906-019-2449-0) contains supplementary material, which is available to authorized users.

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Section: Resultssupporting

confidence: 71%

Potential in vitro anti-allergic, anti-inflammatory and cytotoxic activities of ethanolic extract of Baliospermum montanum root, its major components and a validated HPLC method

Pipatrattanaseree

Itharat

Mukkasombut

et al. 2019

BMC Complement Altern Med

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“…The adverse effects of HFD on metabolic homeostasis such as dyslipidemia, diabetes mellitus, and cardiovascular diseases, as hypertension and coronary heart disease, are linked to adipose tissue physiology and are highly influenced by gender [34,35]. In addition, the use of complementary treatments such as herbal remedies [36,37] and synthetic products [38,39] have been considered to have huge potential as an information source and starting point for the development of antiobesity products. oxaziridines, heterocyclic compounds containing oxygen, nitrogen and carbon atoms in a three-membered ring, were first reported in the mid-fifties by Emmons [40].…”

Section: Discussionmentioning

confidence: 99%

Hypolipidemic effect of dihydroisoquinoline oxaziridine in high-fat diet-fed rats

Aydi

Gara

Chaaben

et al. 2016

Biomedicine & Pharmacotherapy

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“…The enol form has been identified to be the only one minimum in the ground state while the chelated keto form identified to be the minimum in the excited state [6,7]. Available solid state crystal structures of HBP and related ligands are all of the chelated enol form [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Cyclic Voltammetric Study of 2‐Hydroxybenzophenone (HBP) Derivatives and the Correspondent Change in the Orbital Energy Levels in Different Solvents

2020

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The experimental UV and CV of five substituted 2-hydroxybenzophenones in solvents acetonitrile, n-dimethylformamide and dimethylsulfoxide are presented. Results obtained were used to determine their experimental highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and the results were compared to their theoretical model. The derivatives with an electron withdrawing group (EWG) have more favourable reduction potential, electron affinity, lower dipole moment, lower LUMO and HOMO energy levels and longer absorption λ max compared to those containing an electron donating group. Acetonitrile enhances the reduction potential especially for those of derivatives with EWG, leading to higher reduction potential compared to solvents DMF and DMSO.

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Synthesis and highly potent hypolipidemic activity of alpha-asarone- and fibrate-based 2-acyl and 2-alkyl phenols as HMG-CoA reductase inhibitors

Cited by 26 publications

References 72 publications

Potential in vitro anti-allergic, anti-inflammatory and cytotoxic activities of ethanolic extract of Baliospermum montanum root, its major components and a validated HPLC method

Potential in vitro anti-allergic, anti-inflammatory and cytotoxic activities of ethanolic extract of Baliospermum montanum root, its major components and a validated HPLC method

Hypolipidemic effect of dihydroisoquinoline oxaziridine in high-fat diet-fed rats

Cyclic Voltammetric Study of 2‐Hydroxybenzophenone (HBP) Derivatives and the Correspondent Change in the Orbital Energy Levels in Different Solvents

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