Anti-inflammatory and antinociceptive potential of Maclura pomifera (Rafin.) Schneider fruit extracts and its major isoflavonoids, scandenone and auriculasin

Küpeli, Esra; Orhan, İlkay Erdoğan; Toker, Gülnur; Yeşilada, Erdem

doi:10.1016/j.jep.2006.02.021

Cited by 50 publications

(45 citation statements)

References 32 publications

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“…Triterpenoids contents in all BP parts by HPLC-DAD According to pharmacological and phytochemical reports on Moraceae plants, they possess antinociceptive and antiinflammatory potency and enrich certain triterpenoid constituents such as betulinic acid, ursolic acid, and oleanolic acid. [12][13][14][15][16] The above triterpenoids possess antinociceptive and anti-inflammatory activity in rodents. [17][18][19] Hence, we further measured the triter- Each value is represented as mean AE SEM (N ¼ 7{10).…”

Section: Effects Of Bp Radix and Fruit On The Microvascular Permeabilmentioning

confidence: 99%

Comparison with Various Parts ofBroussonetia papyriferaas to the Antinociceptive and Anti-Inflammatory Activities in Rodents

Lin

Chen²,

Wu³

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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Section: Effects Of Bp Radix and Fruit On The Microvascular Permeabilmentioning

confidence: 99%

Comparison with Various Parts ofBroussonetia papyriferaas to the Antinociceptive and Anti-Inflammatory Activities in Rodents

Lin

Chen²,

Wu³

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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“…As discussed in previous papers, M. pomifera is a rich source of isoflavones, some of which are "chemically constitutional isomers" [10]. Besides for its activity on PDE5, the prenylated isoflavone osajin (1) has also been studied as an antioxidant, an anticancer and antibacterial agent [11][12][13].…”

Section: Extraction Of Osajin (1) and Synthesis Ofmentioning

confidence: 99%

5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one

Ribaudo

Ongaro

Zagotto

2018

Molbank

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Natural and semi-synthetic compounds are being studied as novel phosphodiesterase 5 (PDE5) inhibitors for the treatment of erectile dysfunction, pulmonary hypertension, and lower urinary symptoms. Maclura pomifera is a source of flavonoids, one of the main classes of molecules investigated for these purposes. The extraction of the natural isoflavone osajin and its modification to obtain a semi-synthetic derivative are described in this short note. 1 H and 13 C-nuclear magnetic resonance spectroscopy (NMR), mass spectrometry, high-performance liquid chromatography (HPLC) and spectroscopic characterization of the title compound are also hereby provided. Two-dimensional (2D) nuclear Overhauser effect spectroscopy (NOESY) NMR, supported by in silico conformational studies, was used to achieve a complete assignment of the proton signals, assessing the correct chemical structure of the compound. Heteronuclear single quantum coherence spectroscopy (HSQC) and heteronuclear multiple bond correlation (HMBC) NMR experiments were performed to assign 13 C chemical shifts. Calculated chemical properties and preliminary in silico docking suggest that this molecule might be a promising candidate as PDE5 inhibitor.

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“…Comanche Indians in North America used the Osage orange roots decoction to treat sore eyes [4]. M. pomifera and its components possess several biological activities including cytotoxic, antitumor, antibacterial, estrogenic, antifungal, antiviral, and antimalarial activities [5][6][7][8][9][10][11][12][13]. Recently, isoflavones isolated from Osage orange have been demonstrated to protect brain cells, or neurons, from the toxic effect of amyloid beta peptide, which is believed to be responsible for the degeneration of neurons in Alzheimer's disease patients.…”

Section: Introductionmentioning

confidence: 99%

Isolation and biological evaluation of prenylated flavonoids from Maclura pomifera

Ross

Orazbekov

Radhakrishnan

et al. 2017

Planta Medica International Open

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Phytochemical analysis of the ethanolic extract of Maclura pomifera fruits yielded four new compounds (I-IV) along with eleven known compounds (V-XV). The crude extract exhibited significant activity towards cannabinoid receptors (CB1: 103.4% displacement; CB2: 68.8% displacement) and possibly allosteric interaction with and opioid receptors (−49.7 and −53.8% displacement, resp.). Compound I was found to be possibly allosteric for and opioid receptors (−88.4 and −27.2% displacement, resp.) and showed moderate activity (60.5% displacement) towards CB1 receptor. Compound II exhibited moderate activity towards cannabinoid receptors CB1 and CB2 (47.9 and 42.3% displacement, resp.). The known compounds (V-VIII) exhibited prominent activity towards cannabinoid receptors: pomiferin (V) (IC 50 of 2.110 and 1.318 M for CB1 and CB2, resp.), auriculasin (VI) (IC 50 of 8.923 M for CB1), warangalone (VII) (IC 50 of 1.670 and 4.438 M for CB1 and CB2, resp.), and osajin (VIII) (IC 50 of 3.859 and 7.646 M for CB1 and CB2, resp.). The isolated compounds were also tested for inhibition of human monoamine oxidase-A and monoamine oxidase-B enzymes activities, where all the tested compounds showed fewer inhibitory effects on MAO-A compared to MAO-B activities: auriculasin (VI) (IC 50 of 1.91 and 45.98 M for MAO-B and MAO-A, resp.).

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Anti-inflammatory and antinociceptive potential of Maclura pomifera (Rafin.) Schneider fruit extracts and its major isoflavonoids, scandenone and auriculasin

Cited by 50 publications

References 32 publications

Comparison with Various Parts ofBroussonetia papyriferaas to the Antinociceptive and Anti-Inflammatory Activities in Rodents

Comparison with Various Parts ofBroussonetia papyriferaas to the Antinociceptive and Anti-Inflammatory Activities in Rodents

5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one

Isolation and biological evaluation of prenylated flavonoids from Maclura pomifera

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