Dammarane-type saponins from leaves of  Ziziphus spina-christi

Bozicevic, Alen; Mieri, Maria De; Benedetto, Angela Di; Gafner, Frank; Hamburger, Matthias

doi:10.1016/j.phytochem.2017.02.028

Cited by 26 publications

(44 citation statements)

References 19 publications

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“…The peak eluting at t R of 52.9 min exhibited product ions with characteristic losses of deoxyhexose [M -H -C 6 H 10 O 4 ] -, deoxyhexose and hexose [M -H -C 6 H 10 O 4 − C 6 H 10 O 5 ]and deoxyhexose and water [M -H -C 6 H 10 O 4 -H 2 O] -(m/z 911, 893, and 749, respectively). These losses of characteristic sugars may correspond to jujuboside B (1) and B1 (2), previously reported in Ziziphus jujuba and Z. spinachristi (Yoshikawa et al 1997;Bozicevic et al 2017) and both belonging to the same genus of Z. joazeiro.…”

Section: Lc-dad-mssupporting

confidence: 61%

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Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Nascimento

Fonseca

Campos

et al. 2020

Rev. Bras. Farmacogn.

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Ziziphus joazeiro Mart., Rhamnaceae, is a plant native to northeast Brazil where it is known as "juazeiro." Its bark, rich in saponins, is widely utilized in folk medicine and as a supply to produce cosmetics. Aiming at the preservation of the species and the search for an alternative vegetal raw material, the phytochemical profiles of bark and leaves were compared by chemical techniques. The foaming index and gravimetric studies indicated that, in general, bark values were approximately twice than those of the leaves. The same occurred with the hemolysis indexes. Extracts were dereplicated by liquid chromatography with diode array detection coupled to mass spectrometry analyses using an atmospheric pressure chemical ionization source, which indicated that at least 5 saponins were common to all bark and leaf samples. The direct infusion high-resolution mass spectrometry analyses revealed at least 44 different saponins distributed between the bark and leaves of the analyzed plant, of which 40 were described for the first time. The data showed that there were similarities between the studied plant organs as demonstrated by mass spectrometry, foaming index, and hemolysis indexes. Therefore, with the application of a suitable standardization procedure the leaves could be a promising source for obtaining "juazeiro-type" saponins.

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Section: Lc-dad-mssupporting

confidence: 61%

“…This fact may indicate that jujuboside is a good marker for these plant organs. Saponins (23) and (25), reported by Bozicevic et al (2017) in Z. spina-christi, were found in almost all bark and leaf samples. In contrast, cristinin A2 was found only in bark samples.…”

Section: Hr-msmentioning

confidence: 81%

Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Nascimento

Fonseca

Campos

et al. 2020

Rev. Bras. Farmacogn.

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“…Note that jujubosides are the main compounds of bark and wood extracts and comprise approximately 30% of all tentatively identified substances (see Tables 2 and S2). Nine have been described in previous studies, 10,12 seven were reported in Ziziphus species, 28,32–34 three in B. monnieri , 39 and the other eight are being tentatively identified for the first time in the literature. All new structures are only proposed based on product ion scan and high‐resolution measurements and their structures should be further confirmed by nuclear magnetic resonance (NMR) spectra in future work.…”

Section: Resultsmentioning

confidence: 87%

“…Aglycones listed in Table 1 as 1 , 5 , 7 , and 8 have already been reported in AA, 3,8,10,12 and some other aglycones were described in different species: 2 in B. monnieri ; 39 3 in H. trichocarpa ; 35 4 in Z. jujuba and Z. joazeiro ; 28,31 6 in Z. joazeiro ; 29 9 in P. ginseng ; 37,38 10 and 15 in H. acerba ; 36 and 11 , 12 , 13 and 14 in Z. spina‐christ. 32 …”

Section: Resultsmentioning

confidence: 99%

“…An MS/MS library was created through a literature search of saponins already described for AA 3,8–10,12 and other species of the Rhamnaceae family such as Ziziphus joazeiro , 28–30 Z. jujuba , 28,31–34 Z. spina‐christi , 32 Hovenia trichocarpa 35 and H. acerba , 36 as well as for other species with dammarane saponins such as Panax ginseng 37,38 and Bacopa monnieri. 39 No phytochemical data are available for the other two Ampelozizyphus species.…”

Section: Methodsmentioning

confidence: 99%

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Mass spectrometry as a tool for the dereplication of saponins from Ampelozizyphus amazonicus Ducke bark and wood

Mendonça

Simas

et al. 2020

Phytochemical Analysis

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Introduction Mass spectrometry in natural products research has been used as a first step to identify possible chemical structures and to guide subsequent efforts to isolate novel compounds. Preparations of Ampelozizyphus amazonicus Ducke (AA) are known for their high content of saponins, especially dammarane‐type triterpenoid aglycones. In the Amazon, where it is known as “saracura‐mirá”, roots and bark are widely used for the treatment and prevention of malaria, while the wood is discarded. The extract prepared from the wood is also saponin‐rich, but its exact chemical composition has not been described. Objective This study provides information on the chemical profiling and tentative structural identification of the major compounds (saponins) present in aqueous and ethanol extracts of bark and wood of AA by mass spectrometry. Methods The strategy used to identify compounds present in all samples was ultra‐high‐performance liquid chromatography with an ultraviolet detector coupled to tandem mass spectrometry (UHPLC‐UV‐MS/MS) for the analysis of fragmentation patterns through product ion scan using MZmine 2 software. Also, direct sample injection and electrospray ionisation combined with high‐resolution mass spectrometry (DI‐ESI‐HRMS) measurements were performed. Results The extracts showed chemical similarity, and 95 saponins were tentatively identified in AA wood and bark, including 73 which are described for the first time as tentative structures for this plant species. Conclusion This research describes a useful method for the fast and simultaneous tentative identification of major saponins in AA, contributing to the study of the chemical properties of this genus and family. Furthermore, it demonstrates the importance of the qualitative dereplication process, allowing a straightforward way to propose the tentative identification of compounds.

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Ziziphus lotus (L.) Lam. as a Source of Health Promoting Products: Metabolomic Profile, Antioxidant and Tyrosinase Inhibitory Activities

Cacciola¹,

D’Angelo²,

Raimondo³

et al. 2022

Chemistry & Biodiversity

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The methanolic extract of the stem bark of a wild species of jujube, Ziziphus lotus (L.) Lam., growing in Sicily, was chemically and biologically investigated. The chemical profile was defined by UHPLC‐HR‐ESI‐Orbitrap/MS analysis whereas antioxidant and tyrosinase inhibitory activities were investigated by in vitro assays. The extract showed a high total phenolic and flavonoid content (TPC=271.65 GAE/g and TFC=188.11 RE/g extract). Metabolomic analysis revealed a rich phytocomplex characterized by phenols, cyclopeptide alkaloids, and triterpenoid saponins, some of which here detected for the first time. The mushroom tyrosinase inhibition assay displayed that the methanolic extract efficiently inhibits the monophenolase and diphenolase activity. Furthermore, the extract showed a strong ability to scavenge DPPH, a good Fe3+ reducing antioxidant power, in addition to a Fe2+ chelating activity. Taken together, these results suggest possible novel applications of wild jujube stem bark as a source of potential skin‐care agents with several uses in pharmaceutical and cosmetic industries.

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Dammarane-type saponins from leaves of Ziziphus spina-christi

Cited by 26 publications

References 19 publications

Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Mass spectrometry as a tool for the dereplication of saponins from Ampelozizyphus amazonicus Ducke bark and wood

Ziziphus lotus (L.) Lam. as a Source of Health Promoting Products: Metabolomic Profile, Antioxidant and Tyrosinase Inhibitory Activities

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