Quinolone Alkaloids Along with Other Constituents from Zanthoxylum rhetsa and their Chemotaxonomic Significance

Tuz-Zohora, Fatema; Muhit, Md. Abdul; Hasan, Choudhury M.; Ahsan, Monira

doi:10.25135/rnp.57.17.11.182

Cited by 6 publications

(2 citation statements)

References 5 publications

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“…1 H‐NMR (400 MHz, DMSO) δ : 7.99 (1H, d, J = 2.8 Hz, H‐2), 7.97 (1H, d, J = 9.4 Hz, H‐5), 7.44 (1H, d, J = 2.8 Hz, H‐3), 7.41 (1H, d, J = 9.4 Hz, H‐6), 4.43 (1H, s, OCH 3 ), 3.96 (1H, s, OCH 3 ), 3.91 (1H, s, OCH 3 ). 13 C‐NMR (101 MHz, DMSO) δ : 164.3 (C‐9a), 157.2 (C‐4), 152.4 (C‐8a), 144.2 (C‐2), 141.8 (C‐7), 141.2 (C‐8), 118.3 (C‐5), 114.6 (C‐3a), 113.0 (C‐6), 105.9 (C‐3), 102.2 (C‐4a), 61.2 (OCH 3 ), 59.9 (OCH 3 ), 57.0 (OCH 3 ) .…”

Section: Resultsmentioning

confidence: 99%

Rapid screening and purification of potential alkaloid neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. roots via ultrafiltration liquid chromatography combined with stepwise flow rate counter‐current chromatography

Chen-xiao

Zhu

et al. 2019

J of Separation Science

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Toddalia asiatica (Linn.) Lam. is a medical plant traditionally used to treat coughs, fevers, and various diseases. Alkaloids are the main active ingredients in Toddalia asiatica (Linn.) Lam., but traditional methods for screening and separation are complex and labor‐intensive. In this work, an efficient strategy was developed to rapidly screen, identify, and separate neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. Ultrafiltration, high performance liquid chromatography, and time‐of‐flight mass spectrometry were employed for rapid screening and identification of neuraminidase inhibitors. A two‐phase solvent system comprising n‐hexane/ethyl acetate/methanol/water (5:5:3:7, v/v) was then selected for separation by high‐speed counter‐current chromatography. A sample loading of 200 mg and a stepwise flow rate were achieved by increasing the flow rate from 2 to 4 mL/min after 4 h. Three main fluoroquinoline alkaloids (haplopine, skimmianine, and 5‐methoxydictamnine) along with two coumarins were obtained via one‐step separation and their structures were determined by mass spectrometry and nuclear magnetic resonance. In vitro assays revealed skimmianine with half‐maximal inhibitory concentration of 16.2 ± 0.7 µmol/L was selected as the potential highest neuraminidase inhibitor. The results suggest that ultrafiltration high performance liquid chromatography–mass spectrometry combined with high‐speed counter‐current chromatography is efficient for the screening and isolation of neuraminidase inhibitors from complex natural products.

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Section: Resultsmentioning

confidence: 99%

Rapid screening and purification of potential alkaloid neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. roots via ultrafiltration liquid chromatography combined with stepwise flow rate counter‐current chromatography

Chen-xiao

Zhu

et al. 2019

J of Separation Science

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“…The fruits and stem bark of Z. rhetsa are used in the treatment of asthma, bronchitis, heart complaints and rheumatism [6]. Chemical analysis of Zanthoxylum rhetsa allows the isolation of two pyranoquinoline alkaloids, 8-methoxy-n-methylflindersine (1) and zanthodioline (2), which has been previously reported from Zanthoxylum rhetsa and Zanthoxylum simulans respectively [7]. The present paper also describes antioxidant, thrombolytic, cytotoxicity and antimicrobial activity of the PE, CTC, CF and AQ soluble fractions of Zanthoxylum rhetsa root bark along with two isolated quinolone alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant, Cytotoxic, Thrombolytic and Antimicrobial Activity of <i>Zanthoxylum rhetsa</i> Root Bark with Two Isolated Quinolone Alkaloids

Zohora¹,

Islam²,

Khan³

et al. 2019

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The background of this study was to investigate the antioxidant, cytotoxic, thrombolytic and antimicrobial activity of the petroleum ether (PE), carbon tetrachloride (CTC), chloroform (CF) and aqueous (AQ) soluble fractions of crude methanolic Zanthoxylum rhetsa root bark with two isolated quinolone alkaloids, 8-methoxy-n-methylflindersine (1) and zanthodioline (2). Structures were characterized by 1D NMR analyses. Antioxidant activity was assessed by using DPPH assay and antimicrobial activity was screened by disc diffusion method. An in vitro thrombolytic model was used to evaluate the clot lysis effect of different extracts of root bark of Z. rhetsa along with streptokinase as a positive control and distilled water as a negative control and the cytotoxic activity of different extracts of Z. rhetsa root bark was evaluated by Brine Shrimp Lethality Bioassay. AQ fraction exhibited strongest antioxidant, cytotoxic and thrombolytic activity among four fractions. The CTC and CF soluble fractions exhibited significant antioxidant, cytotoxic and thrombolytic activity. CTC and AQ fractions gave highest anti-bacterial activity against Vibrio cholera and Klebsiella pneumonia respectively. Compound 1 showed significant activity at a concentration of 100 µgm/disc against Sarcina lutea, Staphylococcus aureus and Salmonella paratyphi-A, Shigella dysenteriae, Shigella boydii and Shigella sonnei with high antioxidant activity. The antioxidant, thrombolytic and antimicrobial activity of 8-methoxy-n-methylflindersine and zanthodioline are the first record from root bark of this plant.

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Bioassay‐Guided Extraction and Isolation of Natural Herbicides from Dried Zanthoxylum limonella Alston Fruits

Chotpatiwetchkul,

Charoenying,

Teerarak

et al. 2024

Asian J Org Chem

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Weeds are problematic plant species around the world. Various strategies exist for controlling weeds, but chemical treatment remains the preferred method, particularly when using natural substances. In this research, a crude aqueous‐methanol extract from dried Zanthoxylum limonella fruits was acid‐base partitioned into four fractions: neutral extract (NE), acid extract (AE), basic extract (BE), and aqueous extract (AQ). These fractions were further separated into seventeen subfractions: NEF1 to NEF7, AEF1 to AEF5, and BEF1 to BEF5, which were then tested for herbicidal activity against the growth of Chinese amaranth (Amaranthus tricolor) and barnyard grass (Echinochloa crus‐galli). Active subfractions were isolated via column chromatography and identified using spectroscopic methods, yielding seven active compounds: xanthoxyline (1), tambulin (2), atanine (3), prudomestin (4), skimmianine (5), p‐methoxybenzoic acid (6), and methyl caffeate (7). Compounds 2–7 had not been previously reported in Z. limonella. Xanthoxyline (1) was identified as the most potent botanical herbicide, fully inhibiting seed germination of Chinese amaranth and barnyard grass. This compound also decreased seed imbibition and α‐amylase activity in both species. Molecular docking studies on the α‐amylase enzyme (PDB ID: 1BG9) revealed that the aromatic, hydroxy, and carbonyl groups of xanthoxyline (1) interact with the enzyme's active sites.

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Quinolone Alkaloids Along with Other Constituents from Zanthoxylum rhetsa and their Chemotaxonomic Significance

Cited by 6 publications

References 5 publications

Rapid screening and purification of potential alkaloid neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. roots via ultrafiltration liquid chromatography combined with stepwise flow rate counter‐current chromatography

Rapid screening and purification of potential alkaloid neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. roots via ultrafiltration liquid chromatography combined with stepwise flow rate counter‐current chromatography

Antioxidant, Cytotoxic, Thrombolytic and Antimicrobial Activity of <i>Zanthoxylum rhetsa</i> Root Bark with Two Isolated Quinolone Alkaloids

Bioassay‐Guided Extraction and Isolation of Natural Herbicides from Dried Zanthoxylum limonella Alston Fruits

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Quinolone Alkaloids Along with Other Constituents from Zanthoxylum rhetsa and their Chemotaxonomic Significance

Cited by 6 publications

References 5 publications

Rapid screening and purification of potential alkaloid neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. roots via ultrafiltration liquid chromatography combined with stepwise flow rate counter‐current chromatography

Rapid screening and purification of potential alkaloid neuraminidase inhibitors from Toddalia asiatica (Linn.) Lam. roots via ultrafiltration liquid chromatography combined with stepwise flow rate counter‐current chromatography

Antioxidant, Cytotoxic, Thrombolytic and Antimicrobial Activity of &lt;i&gt;Zanthoxylum rhetsa&lt;/i&gt; Root Bark with Two Isolated Quinolone Alkaloids

Bioassay‐Guided Extraction and Isolation of Natural Herbicides from Dried Zanthoxylum limonella Alston Fruits

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Antioxidant, Cytotoxic, Thrombolytic and Antimicrobial Activity of <i>Zanthoxylum rhetsa</i> Root Bark with Two Isolated Quinolone Alkaloids