Isolation and structure elucidation of cyclopeptide alkaloids from Ziziphus nummularia and Ziziphus spina-christi by HPLC-DAD-MS and HPLC-PDA-(HRMS)-SPE-NMR

Tuenter, Emmy; Foubert, Kenn; Apers, Sandra; Pieters, Luc

doi:10.1016/j.phytochem.2017.02.029

Cited by 24 publications

(15 citation statements)

References 20 publications

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“…[910] Z. spina-christi has documented antimicrobial, antifungal,[111213] anti-inflammatory,[14] antioxidant,[1516] and antidiabetic properties. [1718] The chemical composition, that is, the presence of flavonoids,[12] alkaloids,[19] and saponins,[20] is consistent with these activities.…”

Section: Introductionmentioning

confidence: 89%

A completely polyherbal conditioning and antioxidant shampoo: A phytochemical study and pharmaceutical evaluation

et al. 2019

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A BSTRACT Aim: A recent approach in shampoo research has been to find a natural alternative for synthetic detergents that have deteriorative effects on hair follicles. This study aimed at the formulation of a completely herbal shampoo containing a natural foaming agent, in addition to having conditioning, antioxidant, and antimicrobial effects. Material and Methods: The leaves of Salix babylonica L., Ziziphus spina-christi L. (Willd), and Glycyrrhiza glabra rhizomes were extracted with 70% methanol then quantified for their phenolic and flavonoid contents using colorimetric assays that were qualitatively identified by Ultra-performance liquid chromatography (UPLC) with tandem mass spectrometry (MS-MS). The mineral content was also estimated. The radical scavenging activity was estimated using 1,1-diphenyl-2-Picrylhydrazyl (DPPH) and the half maximal inhibitory concentration (IC50) was determined. Additionally, the antimicrobial activity was tested using agar diffusion assay and compared to vancomycin and ketoconazole. Four formulations, consisting of the different plant extracts and a combination of the extracts, were prepared and evaluated for several physicochemical properties. The best formula was evaluated for its conditioning effects using scanning electron microscope and blind touch tests by asking volunteers for grading the formulations. Results and Discussion: UPLC-MS-MS analysis of S. babylonica and Z. spina-christi allowed tentative identification of 12 phytoconstituents in each. Z. spina-christi showed the highest phenolic content and a high copper, zinc, and manganese content beside the best antioxidant activity, whereas G. glabra had a high potency against Bacillus cereus and Candida albicans . The polyherbal shampoo formulation (F4) was selected as an optimized formulation because of a high foam stability after 4 min, low wetting time (2 s), surface tension reduction, and comparable results for percent solid content. F4 showed good conditioning effect and consumer contentment. Conclusion: The formulated polyherbal shampoo is chemical free, extra-nourishing shampoo with excellent conditioning, cleansing, and antimicrobial effects.

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Section: Introductionmentioning

confidence: 89%

A completely polyherbal conditioning and antioxidant shampoo: A phytochemical study and pharmaceutical evaluation

et al. 2019

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“…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%

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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“…Spinanine B ( 451 ) (Fig. 59), a cyclopeptide alkaloid from the stem bark of Ziziphus spina - christi (Rhamnaceae), inhibited the K1 strain of P. falciparum without cytotoxicity to MRC-5 cells at 64 µM [280]. Evaluation of the antiplasmodial activity of 19 cyclopeptide alkaloids facilitated some SAR conclusions.…”

Section: Macrocyclesmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

124

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BackgroundMalaria remains a significant public health challenge in regions of the world where it is endemic. An unprecedented decline in malaria incidences was recorded during the last decade due to the availability of effective control interventions, such as the deployment of artemisinin-based combination therapy and insecticide-treated nets. However, according to the World Health Organization, malaria is staging a comeback, in part due to the development of drug resistance. Therefore, there is an urgent need to discover new anti-malarial drugs. This article reviews the literature on natural products with antiplasmodial activity that was reported between 2010 and 2017.MethodsRelevant literature was sourced by searching the major scientific databases, including Web of Science, ScienceDirect, Scopus, SciFinder, Pubmed, and Google Scholar, using appropriate keyword combinations.Results and DiscussionA total of 1524 compounds from 397 relevant references, assayed against at least one strain of Plasmodium, were reported in the period under review. Out of these, 39% were described as new natural products, and 29% of the compounds had IC50 ≤ 3.0 µM against at least one strain of Plasmodium. Several of these compounds have the potential to be developed into viable anti-malarial drugs. Also, some of these compounds could play a role in malaria eradication by targeting gametocytes. However, the research into natural products with potential for blocking the transmission of malaria is still in its infancy stage and needs to be vigorously pursued.

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Isolation and structure elucidation of cyclopeptide alkaloids from Ziziphus nummularia and Ziziphus spina-christi by HPLC-DAD-MS and HPLC-PDA-(HRMS)-SPE-NMR

Cited by 24 publications

References 20 publications

A completely polyherbal conditioning and antioxidant shampoo: A phytochemical study and pharmaceutical evaluation

A completely polyherbal conditioning and antioxidant shampoo: A phytochemical study and pharmaceutical evaluation

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

Antiplasmodial natural products: an update

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