A New Ceramide (Rumexamide) and Other Chemical Constituents from &amp;lt;i&amp;gt;Rumex abyssinicus&amp;lt;/i&amp;gt; Jacq (Polygonaceae): Isolation, Characterization, Antibacterial Activities and Chemophenetic Significance

Tsamo, Léonel Donald Feugap; Yimgang, Lorette Victorine; Wouamba, Steven Collins Njonte; Mkounga, Pierre; Nkengfack, Augustin Ephrem; Voutquenne-Nazabadioko, Laurence; Ngnokam, David; Lenta, Bruno Ndjakou; Sewald, Norbert

doi:10.4236/abc.2021.115018

Cited by 10 publications

(4 citation statements)

References 47 publications

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“…Tirteen compounds (Figure 1) have been isolated and characterized from the chemical investigation of the methanol extract of the bark of Z. gilletii. Based on their spectroscopic ( 1 H and 13 C) NMR and spectrometric (EI-MS) data (see Table 1S on supplementary data), as well as the comparison of these data with those reported in the literature, the isolated compounds have been identifed as 5-hydroxynoracronycine (1) [21], decarine (2) [22], trans-fagaramide (3) [23], cis-fagaramide (4) [24], sesamin (5) [25,26], scoparone (6) [27], scopoletin (7) [28], fridelin (8) [29], lupeol (9) [30,31], erythrodiol-3-O-palmitate (10) [32], vanillic acid (11) [23], stigmasterol (12), and stigmasterol-3-O-β-Dglucopyranoside (13) [31,33].…”

Section: Resultsmentioning

confidence: 67%

Chemical Constituents of the Bark of Zanthoxylum gilletii (Rutaceae) and Their In Vitro Antiplasmodial and Molecular Docking Studies

Dzouemo

Happi

Ahmed

et al. 2022

Journal of Chemistry

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The phytochemical investigations of the methanol extract of Zanthoxylum gilletii bark led to the isolation of thirteen compounds identified as two alkaloids including one acridone 5-hydroxynoracronycine (1) and one benzo [c] phenanthridine decarine (2), three lignans trans- and cis-fagaramide (3 and 4) and sesamin (5), two coumarins scoparone (6) and scopoletin (7), three pentacyclic triterpenoids fridelin (8), lupeol (9) and erythrodiol-3-O-palmitate (10), one phenolic compound vanillic acid (11) as well as two common steroids stigmasterol (12), and its derivative stigmasterol-3-O-β-D-glucopyranoside (13). The structures of all the isolated compounds were elucidated by means of their spectroscopic and spectrometric data (1D, 2D-NMR, MS) as well as the comparison of these data with those reported in the literature. Except for compounds 9 and 11–13, all the other isolated compounds are reported for the first time from Z. gilletii but have been already obtained from other Zanthoxylum species and in the Rutaceae family. Compounds 1, 3–5, and 9 were tested in vitro for their antiplasmodial potencies against Plasmodium falciparum 3D7, and the results revealed that all the tested compounds displayed an inhibition between 51.89% and 54.69% while only the mixture of 3 + 4 gave an IC50 lower than 10 000 nM (IC50 = 1333 nM). Furthermore, all the compounds have been evaluated in silico for their ability to inhibit the Plasmodium falciparum dihydroorotate dehydrogenase 5TBO. Sesamin (5) showed the greatest affinity to the antiplasmodium receptor than artemether® and chloroquine®. Further recorded data from their ADMET study, as well as their chemotaxonomy, are also discussed herein. The present study provides further information to enrich the chemistry of Z. gilletii and its qualification as an important source for good candidates in new antiplasmodial drug development.

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Section: Resultsmentioning

confidence: 67%

Chemical Constituents of the Bark of Zanthoxylum gilletii (Rutaceae) and Their In Vitro Antiplasmodial and Molecular Docking Studies

Dzouemo

Happi

Ahmed

et al. 2022

Journal of Chemistry

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“…An orange-red powder; mp 194-197 o C; UV-Vis (MeOH) λmax nm: 259, 290 and 433; IR (KBr): νmax cm -1 : 3417, 1676, and 1631; EI MS: [M] + peak at m/z 254.0 corresponding C15H10O4 (calc. mass, 254.0579); 1 H-NMR (500 MHz, CDCl3), chemical shift δ in ppm, coupling constant J in Hz: δH 1.43 12.11 (1H, s, OH-8), 12.00 (1H, s, OH-1), 7.81 (1H, dd, J = 7.55, 0.9 , H-5), 7.65 (1H, t, J = 8.45, H-6), 7.64 (1H, d, = 0.9 Hz, H-4), 7.27 (1H, dd, J = 8.45, 0.9, H-7), 7.09 (1H, br.s, H-2), 2.45 (3H, s, H-11); 13 β-Sitosterol (5). White solid; mp 134-136 o C; UV-Vis (CHCl3) λmax nm: no absorption 600-200; IR (KBr) vmax cm -1 : 3415, 2937, 2843, 1659, 1447, 1381 and 1048; EI MS: [M] + peak at m/z 414.4 corresponding to molecular formula C29H50O (calc.…”

Section: Characterization and Identification Of Compoundsmentioning

confidence: 99%

“…White solid; mp 134-136 o C; UV-Vis (CHCl3) λmax nm: no absorption 600-200; IR (KBr) vmax cm -1 : 3415, 2937, 2843, 1659, 1447, 1381 and 1048; EI MS: [M] + peak at m/z 414.4 corresponding to molecular formula C29H50O (calc. mass, 414.3862); 1 H-NMR (500 MHz, CDCl3), chemical shift δ in ppm, coupling constant J in Hz: δ 5.33 (1H, m,, H-6), 3.50 (1H, m, H-3), 0.99 (3H, s, H-19), 0.90 (3H, d, J = 6.55, H-21), 0.83 (3H, t, J = 7.45, H-29), 0.81 (3H, d, J = 6.85, H-26), 0.79 (3H, d, J = 6.8, H-27), 0.66 (3H, s, H-18); 13…”

Section: Characterization and Identification Of Compoundsmentioning

confidence: 99%

“…The phytochemical studies of R. abyssinicus extract revealed the presence of tannins, flavonoids, phenols, quinones, alkaloids, cartenoids, phlobatannins, terpenoids, naphthalenes, stilbenoids, steroid, glycosides, saponins, fats and oils [7][8][9]. Many compounds are reported from R. abyssinicus including chrysophanol (1), physcion (2), emodin (3), citreorosein (4), β-sitosterol (5), aloe-emodin, emodic acid, chrysophanol-8-β-D-glucoside, emodin-β-8-O-D-glucoside, physcion-β-8-O-D-glucoside, bianthrone, emodin-chrysophanol, helminthosporin, epicatechin, epicatechin-3-O-gallate, epicatechin-3-O-(4″-O-methyl)gallate, methyl gallate, oxalic acid, phenolic acid, rumexamide, oleanolic acid, lupeol, 3β,28-dihydroxylup-20 (22)-ene 3βdihydroxylup-20(29)-en-28-oic acid, stigmasterol, stigmasterol-3-O-β-D-glucoside stigmastane-3,6-dione and ergosta-6,22-diene-3,5,8-triol [2,[10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

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In vitro antifungal, anti-inflammatory and cytotoxic activities of Rumex abyssinicus rhizome extract and bioassay-guided isolation of cytotoxic compounds from Rumex abyssinicus

Emam¹,

Yaya²,

Choudhary³

et al. 2022

Bull. Chem. Soc. Eth.

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ABSTRACT. Rumex abyssinicus showed strong cytotoxicity against HeLa cells (IC50 = 22.25 μg/mL) and weak cytotoxicity against PC3 and BJ cells with percent inhibition of 58.6, 25.8 and 29.7% at 30.0 μg/mL. It showed moderate antifungal activity against Aspergillus niger with a percent growth inhibition of 55.5% at 3000 µg/mL. It also strongly inhibited oxidative burst with IC50 value of 24.8 μg/mL. DCM (100%) and DCM: EtOAc (1:1) fractions showed strong cytotoxicity against HeLa cells, whilst pet ether: DCM (1:1) fraction showed strong cytotoxicity against PC3 cells with IC50 values of 29.3, 26.3 and 24.3 μg/mL, respectively. Moreover, the DCM: EtOAc (1:1) fraction inhibited ROS production with IC50 value of 18.8 μg/mL. Cytotoxic fractions afforded chrysophanol (1), physicon (2), emodin (3), citreorosein (4) and β-sitosterol (5). Among the isolated compounds, emodin (3) showed strong cytotoxicity against HeLa cells, whilst chrysphanol (1) and physicon (2) showed strong cytotoxicity against PC3 cells with IC50 values of 8.94, 22.5, and 28.5 µM, respectively. In addition, emodin (3) and citreorosein (4) showed strong inhibition against ROS production with an IC50 value of 16.2 and 38.2 μg/mL. The findings of this study suggest R. abyssinicus as a good candidate for cancer and inflammation management. KEY WORDS: Polygonaceae, Rumex abyssinicu Jacq., Cytotoxic, Antifungal, Anti-Inflammatory, Reactive oxygen species Bull. Chem. Soc. Ethiop. 2022, 36(4), 879-892. DOI: https://dx.doi.org/10.4314/bcse.v36i4.13

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Antimicrobial and Cytotoxic Potential of Helminthosporin from Rumex abyssiniscus Jacq. Discovered as a Novel Source of Syringic Acid and Bis(2-ethyloctyl) Phthalate

et al. 2022

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A New Ceramide (Rumexamide) and Other Chemical Constituents from <i>Rumex abyssinicus</i> Jacq (Polygonaceae): Isolation, Characterization, Antibacterial Activities and Chemophenetic Significance

Cited by 10 publications

References 47 publications

Chemical Constituents of the Bark of Zanthoxylum gilletii (Rutaceae) and Their In Vitro Antiplasmodial and Molecular Docking Studies

Chemical Constituents of the Bark of Zanthoxylum gilletii (Rutaceae) and Their In Vitro Antiplasmodial and Molecular Docking Studies

In vitro antifungal, anti-inflammatory and cytotoxic activities of Rumex abyssinicus rhizome extract and bioassay-guided isolation of cytotoxic compounds from Rumex abyssinicus

Antimicrobial and Cytotoxic Potential of Helminthosporin from Rumex abyssiniscus Jacq. Discovered as a Novel Source of Syringic Acid and Bis(2-ethyloctyl) Phthalate

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