Concise synthesis of E/F ring spiroethers from tigogenin. Carbaanalogs of steroidal sapogenins and their biological activity

Czajkowska-Szczykowska, Dorota; Olchowik-Grabarek, Ewa; Sękowski, Szymon; Żarkowski, Jacek; Morzycki, Jacek W.

doi:10.1016/j.jsbmb.2022.106174

Cited by 5 publications

(5 citation statements)

References 48 publications

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“…The values of fluorescence anisotropy were automatically calculated by the Perkin-Elmer (LS-55B) spectrofluorometer software (FL WINLAB version. 4.00.02) according to the Jablonski equation (Equation ( 1)) [86,87]:…”

Section: Measurements Of Membrane Fluiditymentioning

confidence: 99%

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Cannabidiol and Cannabigerol Modify the Composition and Physicochemical Properties of Keratinocyte Membranes Exposed to UVA

Wroński¹,

Dobrzyńska

Sękowski

et al. 2023

IJMS

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The action of UVA radiation (both that derived from solar radiation and that used in the treatment of skin diseases) modifies the function and composition of keratinocyte membranes. Therefore, this study aimed to assess the effects of phytocannabinoids (CBD and CBG), used singly and in combination, on the contents of phospholipids, ceramides, lipid rafts and sialic acid in keratinocyte membranes exposed to UVA radiation, together with their structure and functionality. The phytocannabinoids, especially in combination (CBD+CBG), partially prevented increased levels of phosphatidylinositols and sialic acid from occurring and sphingomyelinase activity after the UVA exposure of keratinocytes. This was accompanied by a reduction in the formation of lipid rafts and malondialdehyde, which correlated with the parameters responsible for the integrity and functionality of the keratinocyte membrane (membrane fluidity and permeability and the activity of transmembrane transporters), compared to UVA-irradiated cells. This suggests that the simultaneous use of two phytocannabinoids may have a protective effect on healthy cells, without significantly reducing the therapeutic effect of UV radiation used to treat skin diseases such as psoriasis.

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Section: Measurements Of Membrane Fluiditymentioning

confidence: 99%

“…The label was added to cells suspended in 10 mM PBS (pH = 7.4) at a final concentration of 1 µM. The prepared samples were well vortex-mixed and incubated for 20 min at 25 • C. Lipid raft formation was analyzed according to Czajkowska-Szczykowska et al [87].…”

Section: Analysis Of Lipid Raft Formation Using Fluorescence Techniquementioning

confidence: 99%

Cannabidiol and Cannabigerol Modify the Composition and Physicochemical Properties of Keratinocyte Membranes Exposed to UVA

Wroński¹,

Dobrzyńska

Sękowski

et al. 2023

IJMS

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“…[37] Tigogenin (spirostane sapogenin) against C. albicans. [40] The main mechanism of action described for steroid saponins against fungi has been the disruption of the cell membrane, causing the membrane to become more permeable to ions and the extravasation of cellular components to occur. [41] Diosgenin has already demonstrated antifungal activity against other species, such as the ability to prevent the fungus Cryptococcus neoformans from crossing the blood-brain barrier and prevent cryptococcal meningitis, through the inhibition of the virulence factor and the proteolytic activity of the recombinant Mpr1 protein without affecting the viability of the fungus.…”

Section: Discussionmentioning

confidence: 99%

“…Dioscin against C. glabrata and C. parapsilosis [37] . Tigogenin (spirostane sapogenin) against C. albicans [40] …”

Section: Discussionmentioning

confidence: 99%

In vitro Evaluation of Fungal Susceptibility and Inhibition of Virulence by Diosgenin

do Socorro Costa,

da Silva,

Santos Araújo

et al. 2024

Chemistry & Biodiversity

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Fungal infections are a public health problem that mainly affects immunosuppressed people, Candida spp. have been responsible for most sources of contamination and invasive fungal infections described around the world. The need arises to find new therapeutic approaches to combat growing infections. Plants and natural products have been considered a valuable source for discovering new molecules with active ingredients. Diosgenin is a sapogenin found in the families of Leguminosae and Dioscoreaceae, it is obtained mainly from the dioscin saponin through the hydrolysis method, it is a phytochemical that has been highlighted in the treatment of various diseases, as well as in combating microbial resistance. The present study aimed to evaluate the susceptibility of fungal strains to diosgenin, as well as verify the association with the reference drug and evaluate the inhibition of the virulence factor through morphological changes in the yeast state to the filamentous form of hyphae and pseudohyphae in strains of Candida albicans, Candida tropicalis and Candida krusei using the broth microdilution method and microculture technique. Antifungal assays revealed that diosgenin was not able to inhibit the growth of the tested strains.

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“…The antimicrobial activity was examined on the six bacteria strains: Staphylococcus aureus ATCC 700699; Staphylococcus aureus 8325-4; Staphylococcus epidermitis ATCC 14990; Bacillus cereus ATCC 13061; Escherichia coli ATCC 35218; and Pseudomonas aeruginosa ATCC BAA-1744. Analyses were performed according to Czajkowska-Szczykowska et al [ 28 ]. Briefly, the compounds (RT–DMPC nanocomplex and pure RT as control) were added to a Mueller Hinton broth (MHB) medium for the bacteria to a final RT concentration of 500 µM and 5 mg/mL (7.4 mM) of DMPC.…”

Section: Methodsmentioning

confidence: 99%

Interaction of Rhus typhina Tannin with Lipid Nanoparticles: Implication for the Formulation of a Tannin–Liposome Hybrid Biomaterial with Antibacterial Activity

Sękowski

Naziris

Olchowik-Grabarek

et al. 2023

JFB

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Tannins are natural plant origin polyphenols that are promising compounds for pharmacological applications due to their strong and different biological activities, including antibacterial activity. Our previous studies demonstrated that sumac tannin, i.e., 3,6-bis-O-di-O-galloyl-1,2,4-tri-O-galloyl-β-D-glucose (isolated from Rhus typhina L.), possesses strong antibacterial activity against different bacterial strains. One of the crucial factors of the pharmacological activity of tannins is their ability to interact with biomembranes, which may result in the penetration of these compounds into cells or the realization of their activity on the surface. The aim of the current work was to study the interactions of sumac tannin with liposomes as a simple model of the cellular membrane, which is widely used in studies focused on the explanation of the physicochemical nature of molecule–membrane interactions. Additionally, these lipid nanovesicles are very often investigated as nanocarriers for different types of biologically active molecules, such as antibiotics. In the frame of our study, using differential scanning calorimetry, zeta-potential, and fluorescence analysis, we have shown that 3,6-bis-O-di-O-galloyl-1,2,4-tri-O-galloyl-β-D-glucose interacts strongly with liposomes and can be encapsulated inside them. A formulated sumac–liposome hybrid nanocomplex demonstrated much stronger antibacterial activity in comparison with pure tannin. Overall, by using the high affinity of sumac tannin to liposomes, new, functional nanobiomaterials with strong antibacterial activity against Gram-positive strains, such as S. aureus, S. epidermitis, and B. cereus, can be formulated.

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Concise synthesis of E/F ring spiroethers from tigogenin. Carbaanalogs of steroidal sapogenins and their biological activity

Cited by 5 publications

References 48 publications

Cannabidiol and Cannabigerol Modify the Composition and Physicochemical Properties of Keratinocyte Membranes Exposed to UVA

Cannabidiol and Cannabigerol Modify the Composition and Physicochemical Properties of Keratinocyte Membranes Exposed to UVA

In vitro Evaluation of Fungal Susceptibility and Inhibition of Virulence by Diosgenin

Interaction of Rhus typhina Tannin with Lipid Nanoparticles: Implication for the Formulation of a Tannin–Liposome Hybrid Biomaterial with Antibacterial Activity

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