New phenolic compounds from <i>Calothamnus quadrifidus</i> R.Br. aerial parts and their antioxidant activity

Ibrahim, Reham R.; Ibrahim, Howida Kamal; Shabana, Samah; El-Hosari, Doaa G.; Ali, Sahar A.; Mahgoub, Shahenda; Moharram, Fatma A.

doi:10.1080/14786419.2020.1789982

Cited by 7 publications

(3 citation statements)

References 21 publications

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“…Negative ESI-MS showed a molecular ion peak at 169.11 [M-H], which corresponded to a Mwt of 170. 1 H NMR and 13 C NMR, and ESI-MS data agreed with the reported data [16]. Accordingly, the compound was confirmed to be gallic acid, see Figure 1a.…”

Section: Structure Elucidation Of Isolated Metabolitessupporting

confidence: 88%

Neuroprotective Role of Microbial Biotransformed Metabolites of Sinapic Acid on Repetitive Traumatic Brain Injury in Rats

Soliman¹,

Hamed²,

Marrez³

et al. 2022

Pharmacophore

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Sinapic acid biotransformation was studied and screened using eleven fungal cultures. Penicillium chermesinum AUMC 275, Aspergillus ochraceus AUMC 11328, and Paecilomyces variotii AUMC 5618 showed positive results in the production of metabolites. Sinapic acid biotransformation resulted in the production of gallic acid after 10 days incubation with P. chermesinum, protocatechuic acid after 7 days with A. ochraceus, and ferulic acid after 5 days with P. variotii. The investigated compounds' anti-inflammatory efficacy results, as well as the suggested binding mechanism, affinity, preferred orientation of each docking pose, and binding free energy with the GSK-3β enzyme, were predicted using molecular modeling. The predicted interaction energies for the examined chemicals agreed with the experimental findings. Moreover, we evaluated the neuroprotective potential of the obtained metabolites using the mild repetitive traumatic brain injury (mRTBI) model. Animals were exposed to 5 repetitive hits once per day by weight drop device and were divided into 6 groups (control, mTBI, mRTBI-10, mRTBI-10+Fa, mRTBI-10+PCA, mRTBI-10+GA). All the treatments decreased cortical contents of Tau protein (dementia marker), inflammatory markers (TNF- and il-6), and signaling molecules such as GSK3B and DKK-1. Furthermore, the histological findings added another neuroprotective potential of obtained metabolites where marked improvements and ameliorative effect on the histoarchtexture of the hippocampus and mild changes in the hippocampus layers by GA, PCA, and FA, respectively. All these effects were mirrored in behavior outcomes, and a significant enhancement in animal behavior was observed. We concluded that GA, PCA, and FA have therapeutic potential for preventing TBI-induced brain injury.

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Section: Structure Elucidation Of Isolated Metabolitessupporting

confidence: 88%

Neuroprotective Role of Microbial Biotransformed Metabolites of Sinapic Acid on Repetitive Traumatic Brain Injury in Rats

Soliman¹,

Hamed²,

Marrez³

et al. 2022

Pharmacophore

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“…Plants are potential sources of natural antioxidants that protects the cells against the damaging effects of reactive oxygen species (ROS) [26]. The scavenging ability of DPPH radical is widely used for antioxidant evaluation of natural products besides other several in vitro complementary assays based on inactivation of O2and NO radicals [27]. DPPH assay was selected to evaluate the antioxidant power of the extracts.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Phytochemical Screening and Biological Evaluation of Dypsis Leptocheilos Leaves Extract and Molecular Docking Study of the Isolated Compounds

Ibrahim

Elsharawy

Elhassab

et al. 2020

Int J Pharm Pharm Sci

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Objective: phytochemical investigation of the ethyl acetate fraction (EAF) of 80% aqueous methanol extract (AME) of Dypsis leptocheilos leaves, in addition to evaluation of the antioxidant, cytotoxic and antimicrobial activities of the AME and EAF. Docking was used to predict and understand cytotoxicity of the isolated compounds. Methods: The ethyl acetate fraction (EAF) of Dypsis leptocheilos leaves was subjected to different chromatographic separation techniques. Structures of the isolated compounds were established by different spectroscopic techniques (1H/13C NMR). Antioxidant activity was evaluated by DPPH assay, while cytotoxicity was evaluated by MTT cell viability assay. Antimicrobial activity was evaluated by agar diffusion method. The docking study was conducted using Auto Dock Vina; the estrogen receptor (PDB 5t92) was used as a receptor for the docking. Results: Chromatographic separation techniques were led to the isolation of five phenolic compounds; these compounds were identified to be apigenin 8-C-β-D-glucopyranoside (Vitexin) (1), apigenin 6-C-β-D-glucopyranoside (Isovitexin) (2), luteolin 7-O-β-D-glucopyranoside (3), luteolin 8-C-β-D-glucopyranoside (Orientin) (4), luteolin 6-C-β-D-glucopyranoside (Isoorientin) (5). They were isolated and identified for the first time from this plant species. The AME and EAF showed moderate activity against Gram positive and Gram negatvie bacteria, while both of them showed similar and powerful antioxidant activity with SC50 = 12.8±0.56 µg/ml and SC50 = 17±0.77 µg/ml respectively, compared to ascorbic (reference drug) SC50 = 14.2±0.35 µg/ml. The EAF showed higher cytotoxic activity on the MCF-7 cells (human breast cancer cell line), with IC50 = 12.3 ± 1.82 µg/ml, compared to Vinblastine Sulfate (reference drug). All isolated compounds showed good binding affinity to the estrogen receptors existed in the MCF-7 cell. Conclusion: Five phenolic compounds were isolated for the first time from the EAF of Dypsis leptocheilos leaves. The AME and EAF extracts showed variable antioxidant, antimicrobial and cytotoxic activities.

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“…Compound 5 ( Tiliroside ). Yellow powder, UV λmax (MeOH, nm): 200, 268, 315, IR (cm −1) 3246, 1648, 1590, 1 H‐NMR (400 MHz, CD 3 OD) δ H ppm: 3.33 (1 H, t, J =1.7, H‐4“), 3.42–3.50 (3H, m, H‐5”,H‐3“, H‐2”), 4.19 (1 H, dd, J =11.8, 6.6, H‐6“a), 4.29 (1 H, dd, J =11.8, 3.0, H‐6”b), 5.23 (1H, d, J =7.5, H‐1“), 6.07 (1 H, d, J =16.0, H‐8”‘), 6.14 (1 H, d, J =2.1, H‐6), 6.31 (1H,d, J =2.1, H‐8), 6.78 ‐ 6.84 (4 H, m, H‐3’, H‐5’, H‐3“‘, H‐5”‘), 7.32 (2H, d, J =8.6, H‐2“‘,H‐6”‘), 7.41 (1 H, d, J =16.0, H‐7“‘), 7.99 (2 H, d, J =9.0, H‐2’, H‐6’).1 3 C‐NMR (100 MHz, CD 3 OD) δ C ppm: 158.8 (C‐2), 135.5 (C‐3), 179.7 (C‐4), 163.3 (C‐5), 100.5 (C‐6), 166.8 (C‐7), 95.3 (C‐8), 159.7 (C‐9), 105.8 (C‐10), 123.1 (C‐1’), 132.5 (C‐2’, C‐6’), 116.4 (C‐3’, C‐5’), 161.5 (C‐4’), 104.4 (C‐1”), 76.2 (C‐2“), 78.4 (C‐3”), 72.1 (C‐4“), 76.1 (C‐5”), 64.6 (C‐6“) 127.5 (C‐1”‘), 131.5 (C‐2“‘, C‐6”‘), 117.1 (C‐3“‘, C‐5”‘), 162.4 (C‐4“‘), 146.9 (C‐7”‘), 115.1 (C‐8“‘), 169.1 (C‐9”‘) [40] …”

Section: Methodsmentioning

confidence: 99%

New Specific α‐Glucosidase Inhibitor Flavonoid from Thymelaea tartonraira Leaves: Structure Elucidation, Biological and Molecular Docking Studies

Soltani

Koubaa

Dhouib

et al. 2023

Chemistry & Biodiversity

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The phytochemical investigation of Thymelaea tartonraira leaves led to the isolation and characterization of six compounds, including one new flavonoid glycoside identified as hypolaetin 8-O-β-D-galactopyranoside (4) along with five known compounds, daphnoretin (1), triumbelletin (2), genkwanin (3), tiliroside (5) and yuankanin (6). Their structures were established based on spectroscopic methods, such as UV, IR, NMR, and HR-ESI-MS. Triumbelletin (2) and tiliroside (5) were isolated for the first time from T. tartonraira leaves. The antioxidant property of all isolated compounds was tested based on DPPH, FRAP and total antioxidant capacity assays. Compound 4 displayed an antioxidant potency more interesting than vitamin C with an IC 50 = 15.00 � 0.50 μg/ ml, followed by compound 5. Furthermore, the both compounds 4 and 5 were tested for their α-amylase inhibitory activity in-vitro. Compound 4 displayed higher potency to inhibit α-amylase, with an IC 50 = 46.49 � 2.32 μg/ml, than compound 5, with an IC 50 = 184.2 � 9.2 μg/ml, while the reference compound acarbose presented the highest potency to inhibit α-amylase with an IC 50 = 0.44 � 0.022 μg/ml. Compound 4 displayed a strong inhibitory ability of α-glucosidase activity approximately twice more than the reference compound, acarbose, with IC 50 values of 60.00 � 3.00 and 125.00 � 6.25 μg/ml, respectively. Thus, compound 4 exhibited a specific inhibitory activity for α-glucosidase. The molecular docking studies have supported our findings and suggested that compound 4 has been involved in various binding interactions within the active site of both enzymes α-amylase and α-glucosidase.

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New phenolic compounds from Calothamnus quadrifidus R.Br. aerial parts and their antioxidant activity

Cited by 7 publications

References 21 publications

Neuroprotective Role of Microbial Biotransformed Metabolites of Sinapic Acid on Repetitive Traumatic Brain Injury in Rats

Neuroprotective Role of Microbial Biotransformed Metabolites of Sinapic Acid on Repetitive Traumatic Brain Injury in Rats

Phytochemical Screening and Biological Evaluation of Dypsis Leptocheilos Leaves Extract and Molecular Docking Study of the Isolated Compounds

New Specific α‐Glucosidase Inhibitor Flavonoid from Thymelaea tartonraira Leaves: Structure Elucidation, Biological and Molecular Docking Studies

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