Balance of Δ5-and Δ7-sterols and stanols in halophytes in connection with salinity tolerance

Розенцвет, О. А.; Котлова, Е. Р.; Нестеров, В. Н.; Senik, Svetlana V.; Shavarda, Aleksey L.

doi:10.1016/j.phytochem.2022.113156

Cited by 8 publications

(4 citation statements)

References 52 publications

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“…and Cucurbitaceae Juss. families are dominated by the Δ7-phytosterol structure [24]. However, the B-ring's double bond structure seems disappear in tomatidine and replaced with hydrogen atoms in C5 and C8 (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Tomatidine Extraction from Various Solvents and Cancer Inhibition Mechanism Through In Silico Analysis

Lisdiana,

Iswari,

Christijanti

et al. 2023

Trends Sci

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Tomatidine is an alkaloid-steroid contained in tomato plant organs that potentially developed as an anti-cancer molecule. However, inappropriate use of solvents is frequently becoming an obstacle in the extractions process. In addition, the mechanism of action of tomatidine in the inhibition of cancer cell signaling pathways needs to be investigated. Therefore, this research aims to discover an appropriate solvent to extract tomatidine effectively, and to analyze the inhibition mechanism of tomatidine against the cancer growth pathway. A total of 80 kg of fresh tomatoes were cut into pieces and steamed at 120 °C for 30 min, then mashed and soaked for 3 days in 70 % ethanol, aquadest, petroleum ether, and chloroform separately, continued with GC/MS analysis. Molecular docking was conducted using targeted proteins including B-Raf proto-oncogen serine/ threonine protein kinase (BRAF), Vascular endothelial growth factor A (VEGFA), Smoothened protein (SMO), Cyclin-dependent kinase 2 (CDK2), and Tyrosine-protein kinase/ Janus kinase-1 (JAK1). The ligand-receptor was performed using AutoDock Vina v1.2.0. The highest extracted tomatidine was found in chloroform at 2.44 % of total alkaloid-steroid, and cannot be found in water. The highest interaction is observed in the SMO-tomatidine interaction complex, followed by JAK-1. Furthermore, physicochemical properties of tomatidine make it invaginated into the hydrophobic side of the target proteins that are mainly triggered by van der Waals and alkyl interaction. Based on the in-silico study, tomatidine significantly interacted in the oncogenic signaling pathways that therapeutically potential inhibit cancer cell proliferation. Further study should be focused on the effectiveness analysis of the SHH signaling pathway in the cancer cell. HIGHLIGHTS Important findings in this study include: Tomatidine, an alkaloid-steroid, is properly extracted in chloroform, petroleum ether and 70 % ethanol, however cannot extracted in aquadest. Furthermore, the aquadest content in 70 % ethanol is likely to reduce the solubility of the tomatidine The tomatidine physicochemical property provides a closed covalent bond that makes it more insoluble in the polar solvent. The only polar side is supported by the hydroxyl group in C-4, side chain C-17, and amide side in N-24 that allowed hydrogen bond formation which is relevant to the docking result In molecular docking, tomatidine strongly triggers Van der Waal forces, alkyl, and pi interaction than hydrogen bond or ionic force Interestingly, ligand-receptor interaction always makes tomatidine invaginated or folded into the protein hydrophobic side and strongly attract non-polar and aromatic amino acid, mostly Val, Ala, Leu, and Phe The significant finding is that tomatidine creates valid interactions with CDK2, BRAF, VEGFA, JAK1, and SMO that are involved in cancer cell proliferation, evading apoptosis, and sustained angiogenesis. The highest interaction is observed in the SMO-tomatidine interaction complex, which may affect the Sonic Hedgehog (SHH) signaling pathway (one of the most significant oncogenic pathways in various types of cancer) Tomatidine is therapeutically potential to inhibit cancer cell proliferation through protein inhibition activities against the SHH signaling pathway in the cancer cell GRAPHICAL ABSTRACT

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Section: Resultsmentioning

confidence: 99%

Tomatidine Extraction from Various Solvents and Cancer Inhibition Mechanism Through In Silico Analysis

Lisdiana,

Iswari,

Christijanti

et al. 2023

Trends Sci

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“…Recent in vivo studies revealed an antidiabetic [ 18 ], a hepatoprotective [ 14 ] and a nephroprotective effect [ 19 ]. These activities are attributed to the presence of various bioactive compounds in Atriplex species such as triterpenes [ 20 ], sterols and phytoecdysteroids [ 21 , 22 , 23 ], but most importantly—triterpene saponins [ 24 , 25 , 26 ] and phenolic compounds [ 11 , 12 , 13 , 14 , 17 , 18 , 19 , 27 , 28 ]. Saponins represent an important group of plant metabolites that are characterized by a wide range of pharmacological activities and clinical applicability.…”

Section: Introductionmentioning

confidence: 99%

Antihyaluronidase and Antioxidant Potential of Atriplex sagittata Borkh. in Relation to Phenolic Compounds and Triterpene Saponins

et al. 2023

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The genus Atriplex provides species that are used as food and natural remedies. In this work, the levels of soluble phenolic acids (free and conjugated) and flavonoids in extracts from roots, stems, leaves and flowers of the unexplored Atriplex sagittata Borkh were investigated by LC-ESI-MS/MS, together with their antioxidant and antihyaluronidase activity. Phenolic acids were present in all parts of A. sagittata; and were most abundant in the leaves (225.24 μg/g dw.), whereas the highest content of flavonoids were found in the flowers (242.71 μg/g dw.). The most common phenolics were 4-hydroxybenzoic and salicylic acids, kaempferol-3-glucoside-7-rhamnoside, kaempferol-3-rutinoside and the rare narcissoside, which was present in almost all morphotic parts. The stem extract had the highest antioxidant activity and total phenolic content (611.86 mg/100 g dw.), whereas flower extract exerted the most potent antihyaluronidase effect (IC50 = 84.67 µg/mL; control—quercetin: IC50 = 514.28 μg/mL). Phytochemical analysis of the flower extract led to the isolation of two triterpene saponins that were shown to be strong hyaluronidase inhibitors (IC50 = 33.77 and 168.15 µg/mL; control—escin: IC50 = 307.38 µg/mL). This is the first report on the presence of phenolics and saponins in A. sagittata. The results suggest that both groups of metabolites may contribute to the overall activity of this plant species.

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“…STs are known to be essential components of membranes, being responsible not only for structural but also for regulatory functions in many key cellular processes. The most common ∆-5 plant STs are β-sitosterol, stigmasterol (24-ethyl sterols), and campesterol (24-methyl sterol), as well as avenasterol and cholesterol, which are contained in relatively small amounts in most species [10]. STs are found in plant tissues both in the free state and in conjunction with fatty acids, as well as in the form of sterylglycosides and acylsterylglycosides.…”

Section: Introductionmentioning

confidence: 99%

The Composition and the Content of ∆-5 Sterols, Fatty Acids, and the Activity of Acyl-Lipid Desaturases in the Shoots of Ephedra monosperma, Introduced in the Botanical Garden of the Cryolithozone of Yakutia

et al. 2023

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Evergreen plants in permafrost ecosystems survive unfavorable autumn cooling and extremely low winter temperatures by maintaining optimal physiological activity of tissue cell membranes. To some extent, these features are due to the properties of shoot lipids performing a number of functions during adaptation. Sterols (STs) play a key role in regulating the fluidity and permeability of plant membranes (phytosterols) with a wide structural diversity. The composition of neutral lipids, STs, and fatty acids (FAs) in shoots of the evergreen shrub Ephedra monosperma growing in the Botanical Garden cryolithozone was first studied with HPTLC-UV/Vis/FLD and GC-MS. Twenty FAs were found, from C14:0 to C23:0; they included mono-, di-, tri-, and tetraene FAs. The high content of β-sitosterol among other ∆-5 sterols and an increased amount of C18:2(∆9,12) linoleic acid in lipids composition during the autumn–winter period was found to play an important role in the adaptation of ephedra shoots to the autumn–winter period, providing the cell membrane with greater plasticity, fluidity, and flexibility. The important role of diene linoleic fatty acid C18:2(∆9,12) in ephedra shoot lipids in the processes of low-temperature adaptation was shown.

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Balance of Δ5-and Δ7-sterols and stanols in halophytes in connection with salinity tolerance

Cited by 8 publications

References 52 publications

Tomatidine Extraction from Various Solvents and Cancer Inhibition Mechanism Through In Silico Analysis

Tomatidine Extraction from Various Solvents and Cancer Inhibition Mechanism Through In Silico Analysis

Antihyaluronidase and Antioxidant Potential of Atriplex sagittata Borkh. in Relation to Phenolic Compounds and Triterpene Saponins

The Composition and the Content of ∆-5 Sterols, Fatty Acids, and the Activity of Acyl-Lipid Desaturases in the Shoots of Ephedra monosperma, Introduced in the Botanical Garden of the Cryolithozone of Yakutia

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