Isolation and Structure Elucidation by LC-DAD-MS and LC-DAD-SPE-NMR of Cyclopeptide Alkaloids from the Roots of <i>Ziziphus oxyphylla</i> and Evaluation of Their Antiplasmodial Activity

Tuenter, Emmy; Ahmad, Rizwan; Foubert, Kenn; Amin, Adnan; Orfanoudaki, Maria; Cos, Paul; Maes, Louis; Apers, Sandra; Pieters, Luc; Exarchou, Vassiliki

doi:10.1021/acs.jnatprod.6b00633

Cited by 15 publications

(13 citation statements)

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“…The in vitro antiplasmodial activity against P. falciparum strain K1 and the cytotoxicity against MRC-5 cells was determined for ten cyclopeptide alkaloids, isolated from the stem bark of Ziziphus nummularia , Ziziphus spina-christi , Ziziphus jujuba , and the root of Hovenia dulcis , all belonging to the Rhamnaceae family, and the results are shown in Table 1 . The results that were previously reported for cyclopeptide alkaloids isolated from the root bark of H. acida (Phyllanthaceae) and the roots of Z. oxyphylla (Rhamnaceae) [ 6 , 7 ] are also included in this table. The highest antiplasmodial activity was found for spinanine-B ( 3 ), with an IC 50 value of 2.1 μM and without cytotoxic effects in concentrations of 64.0 μM or less.…”

Section: Resultsmentioning

confidence: 99%

“…The extraction, isolation, and structure elucidation of 17 of the 19 cyclopeptide alkaloids included in this manuscript were reported previously [ 6 , 7 , 10 , 11 ]. The isolation procedure of adouetine-X and fragulanine is briefly described here:…”

Section: Methodsmentioning

confidence: 99%

“…Nummularine-B was found to be moderately active (IC 50 value of 10.3 μM) against Plasmodium falciparum , but not mauritine-L and nummularine-B methiodide [ 5 ]. Our research group has previously reported the antiplasmodial activity of cyclopeptide alkaloids from Hymenocardia acida and Ziziphus oxyphylla [ 6 , 7 ]. Based on these results, some preliminary conclusions concerning their SAR (structure-activity relationship) were drawn, but given the fact that the number of compounds tested in each of these studies was relatively small, it was not possible to draw definite conclusions.…”

Section: Introductionmentioning

confidence: 99%

“…In the present paper, the antiplasmodial and cytotoxic activities of ten cyclopeptide alkaloids are reported, of which only the antiplasmodial activity of nummularine-B was reported previously [ 5 ]. These results were then combined with previous data obtained by our group in the same test conditions for nine other cyclopeptide alkaloids from H. acida and Z. oxyphylla [ 6 , 7 ], in order to perform a SAR study, and to identify the molecular characteristics that can account for high antiplasmodial activity.…”

Section: Introductionmentioning

confidence: 99%

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Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

et al. 2017

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Cyclopeptide alkaloids are polyamidic, macrocyclic compounds, containing a 13-, 14-, or 15-membered ring. The ring system consists of a hydroxystyrylamine moiety, an amino acid, and a β-hydroxy amino acid; attached to the ring is a side chain, comprised of one or two more amino acid moieties. In vitro antiplasmodial activity was shown before for several compounds belonging to this class, and in this paper the antiplasmodial and cytotoxic activities of ten more cyclopeptide alkaloids are reported. Combining these results and the IC50 values that were reported by our group previously, a library consisting of 19 cyclopeptide alkaloids was created. A qualitative SAR (structure-activity relationship) study indicated that a 13-membered macrocyclic ring is preferable over a 14-membered one. Furthermore, the presence of a β-hydroxy proline moiety could correlate with higher antiplasmodial activity, and methoxylation (or, to a lesser extent, hydroxylation) of the styrylamine moiety could be important for displaying antiplasmodial activity. In addition, QSAR (quantitative structure-activity relationship) models were developed, using PLS (partial least squares regression) and MLR (multiple linear regression). On the one hand, these models allow for the indication of the most important descriptors (molecular properties) responsible for the antiplasmodial activity. Additionally, predictions made for interesting structures did not contradict the expectations raised in the qualitative SAR study.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

et al. 2017

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“…Compound 45 together with others shows high and specific activities against P. falciparum [39] Evidence-Based Complementary and Alternative Medicine A new alkaloid, tavoyanine A (56), and other known alkaloids, roemerine (57), laurolitsine (58), boldine (59), and sebiferine (60) Aporphine alkaloids (56)(57)(58)(59) and morphinandienone (60) Leaf 1.10. Quinoline Alkaloids.…”

Section: Ancistrocladus Ileboensismentioning

confidence: 99%

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Uzor

2020

Evidence-Based Complementary and Alternative Medicine

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Malaria is one of the major health problems in developing countries. The disease kills a large number of people every year and also affects financial status of many countries. Resistance of the plasmodium parasite, the causative agent, to the existing drugs, including chloroquine, mefloquine, and artemisinin based combination therapy (ACT), is a serious global issue in malaria treatment and control. This warrants an urgent quest for novel compounds, particularly from natural sources such as medicinal plants. Alkaloids have over the years been recognized as important phytoconstituents with interesting biological properties. In fact, the first successful antimalarial drug was quinine, an alkaloid, which was extracted from Cinchona tree. In the present review work, the alkaloids isolated and reported recently (2013 till 2019) to possess antimalarial activity are presented. Several classes of alkaloids, including terpenoidal, indole, bisindole, quinolone, and isoquinoline alkaloids, were identified with a promising antimalarial activity. It is hoped that the reports of the review work will spur further research into the structural modification and/or development of the interesting compounds as novel antimalarial drugs.

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Optimization of extraction and quantification technique for phenolics content of garlic (Allium sativum): An application for comparative phytochemical evaluation based on cultivar origin

Ahmad

Riaz

Al‐tarouti

et al. 2020

Biomedical Chromatography

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A range of conventional, i.e. maceration, percolation, ultrasonic assisted, Soxhlet and Soxtec extraction (STE), to advanced extraction techniques of accelerated solvent extraction (ASE) was utilized for the first time in order to optimize the extract yield and recovery of phenolics-gallic acid (GA), rutin (RT) and quercetin (QT)-quantified via ultra-high performance liquid chromatography with diode array detector (UHPLC-DAD). The effect of solvents (n-hexane, dichloromethane and methanol) and temperature (60, 80 and 100 C) upon extraction yield, phenolic content and antioxidant activity (DPPH, ABTS and DPPH) was studied, and the method was validated in commercial food samples from Saudi Arabia, China and India. A high extract yield with percentage recovery was observed for STE (1221.10 mg/5 g; 24.42%) and ASE techniques (91.50 mg/1 g; 9.15%) in methanol at 100 C. UHPLC-DAD showed retention times (min) of 0.67, 1.93 and 1.90 for GA, RT and QT, respectively in the shortest runtime of 3 min. The yield for phenolics was higher for STE/ASE (ppm): 15.27/15.29 (GA), 85.24/37.56 (RT) and 52.20/33.40 (QT), respectively. In terms of antioxidant activities, low IC 50 values (μg/ml) of 1.09/1.18 (DPPH), 2.11/5.32 (ABTS) and 4.35/7.88 (phenazine methosulfate-nicotinamide adenine dinucleotide) were observed for STE and ASE, respectively. Multivariate analysis for STE showed a significant (P = 0.000) correlation for extraction type vs. extract yield and phenolics content; however, there was no significance for antioxidant activities vs. extraction type. ASE showed a positive correlation for solvent vs. extraction yield, phenolics and antioxidant activity; however, there was no correlation for extraction yield and DPPH activity. Principal component analysis for STE showed a major variability (52.02%) for extraction yield and phenolics in PC1 followed by PC2 (38.30%) for antioxidant activities. For ASE, PC1 (48.68%) showed a positive correlation for solvent vs. extraction yield and phenolics while PC2 (33.12%) showed a positive correlation for temperature and antioxidant activities. STE and ASE were the optimized extraction techniques for the garlic food sample while a significant effect of solvent and temperature was observed upon extraction yield, phenolics and antioxidant activity.

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Isolation and Structure Elucidation by LC-DAD-MS and LC-DAD-SPE-NMR of Cyclopeptide Alkaloids from the Roots of Ziziphus oxyphylla and Evaluation of Their Antiplasmodial Activity

Cited by 15 publications

References 23 publications

Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

Optimization of extraction and quantification technique for phenolics content of garlic (Allium sativum): An application for comparative phytochemical evaluation based on cultivar origin

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