3-O-Methylquercetin from Achyrocline satureioides—cytotoxic activity against A375-derived human melanoma cell lines and its incorporation into cyclodextrins-hydrogels for topical administration

Doneda, Eduarda; Bianchi, S.; Pittol, Vanessa; Kreutz, Tainá; Scholl, Juliete Nathali; Ibañez, Irene L.; Bracalente, Candelaria; Durán, Hebe; Figueiró, Fabrício; Klamt, Fábio; Bassani, Valquíria Linck

doi:10.1007/s13346-020-00882-6

Cited by 8 publications

(8 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Therefore, among the quercetin conjugates, 3-O-methylquercetin seems to be a suitable candidate for anticancer therapeutics and extracts from plants which contain high amounts of 3-O-methylquercetin or its glycosides, e.g., N. tabacum, Ophioglossum pedunculosum, Achyrocline satureioides, and Rhamnus nakaharai, ,− should be considered as interesting materials for preparation of pharmaceuticals or dietary supplements.…”

Section: Discussionmentioning

confidence: 99%

Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Stężycka,

Frańska

2023

ACS Omega

View full text Add to dashboard Cite

Recently, much interest has been devoted to finding effective G-quadruplex ligands, both of synthetic or natural origins, which may be of potential use in the field of cancer therapy. Among compounds of natural origin, a common flavonol quercetin has attracted notable attention. Yet, only a modest number of papers have been concerned with a comparison of quercetin conjugates binding to G-quadruplexes. In this study, we applied the survival yield (SY) method in order to compare the stability of G-tetrad complexes with quercetin and its conjugates, namely, 3-Oglycosides and O-methylated conjugates. According to the determined values of E comδ50 , flavonol glycosides bind most effectively with G-tetrads, whereas, among flavonols, 3-O-methylquercetin makes the most effective bonds. Because the aglycone structure is of crucial importance for biological processes, 3-O-methylquercetin seems to be a suitable candidate for anticancer therapeutics, and the extracts from the plants, which contain high amounts of 3-O-methylquercetin or its glycosides, should be considered as interesting materials for preparation of pharmaceuticals or dietary supplements.

show abstract

Section: Discussionmentioning

confidence: 99%

Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Stężycka,

Frańska

2023

ACS Omega

View full text Add to dashboard Cite

show abstract

“…The polymer provides a wide range of viscosity grades depending on the substitution degree and ratios [94]. The systematic search retrieved four articles considering HPMC as a gelling agent in physical hydrogels [95][96][97][98]. Two of them investigated the incorporation of cyclodextrin complexes with APIs into a semisolid gel.…”

Section: Cellulose Derivatives As a Gelling Agentmentioning

confidence: 99%

“…The authors hypothesized that this is due to the presence of a diffusion layer on the skin surface and the cyclodextrin acts as a carrier through it towards the lipophilic skin layer [95]. In another more recent study performed by Doneda and colleagues, different cyclodextrin complexes of the lipophilic flavonoid 3-O-methylquercetin were used to allow its incorporation into a hydrophilic topical formulation [97]. HPMC was used as a gelling agent at 3.5% concentration in the presence of 1% propylene glycol.…”

Section: Cellulose Derivatives As a Gelling Agentmentioning

confidence: 99%

“…Typical yield stress for semisolid formulations is in the range 20-50 (80) Pa and varies according to the method used for its determination [153]. The incorporation of cyclodextrin complexes within the HPMC gel matrix could lead to a decrease in the apparent viscosity, possibly due to hydrophobic interactions between the cyclodextrins and the polymer chains [97]. The composition and type of liposomes also affect, in a different manner, the rheology behavior of a carbomer gel, and can either increase or decrease its yield stress, apparent viscosity, and elasticity [206].…”

Section: Rheology Studiesmentioning

confidence: 99%

See 1 more Smart Citation

Gel Formulations for Topical Treatment of Skin Cancer: A Review

Slavkova

Tzankov

Popova

et al. 2023

Gels

View full text Add to dashboard Cite

Skin cancer, with all its variations, is the most common type of cancer worldwide. Chemotherapy by topical application is an attractive strategy because of the ease of application and non-invasiveness. At the same time, the delivery of antineoplastic agents through the skin is difficult because of their challenging physicochemical properties (solubility, ionization, molecular weight, melting point) and the barrier function of the stratum corneum. Various approaches have been applied in order to improve drug penetration, retention, and efficacy. This systematic review aims at identifying the most commonly used techniques for topical drug delivery by means of gel-based topical formulations in skin cancer treatment. The excipients used, the preparation approaches, and the methods characterizing gels are discussed in brief. The safety aspects are also highlighted. The combinatorial formulation of nanocarrier-loaded gels is also reviewed from the perspective of improving drug delivery characteristics. Some limitations and drawbacks in the identified strategies are also outlined and considered within the future scope of topical chemotherapy.

show abstract

“…As a common folk herb, it is mainly used for the treatment of gastrointestinal diseases and bacterial and viral infections as it has anti-inflammatory and analgesic effects. , It has been reported that its methanolic extracts had a certain anti-hepatoma effect against a human hepatocellular carcinoma cell line, Hep G2 . The cytotoxic activity against A375-derived human melanoma cell lines and antioxidant and anti-inflammatory activities were successively reported in recent years, − which suggested strong medicinal potentials. Through the further research of the chemical constituents of A. satureioides , it was found that there were many bioactive chemical constituents, including flavonoids and phenylpropanoids. − We have been devoted to the localization of A. satureioides for several years and were surprised to find two unprecedented derivatives, 1 and 2 , of 2-methyl-1-(2,3,4,6-tetrahydroxyphenyl)propan-1-one and ( S )-2-methyl-1-(2,3,4,6-tetrahydroxyphenyl)butan-1-one, respectively.…”

Section: Introductionmentioning

confidence: 99%

Achyrophenols A–F: Polycyclic Polyphenol Lactone Skeletons and a Nor-Ursane-Type Triterpenoid from Achyrocline Satureioides

et al. 2021

View full text Add to dashboard Cite

Two novel derivatives of 2-methyl-1-(2,3,4,6-tetrahydroxyphenyl)propan-1-one and (S)-2-methyl-1-(2,3,4,6-tetrahydroxyphenyl)butan-1-one (1 and 2), four novel six-membered lactone phenols (3–6), and a nor-ursane type triterpenoid (7) named Achroacid, were isolated from the aerial part of Achyrocline satureioides. The absolute configurations of 1–7 are presented by spectroscopic data and X-ray crystallographic analysis. A DP4plus evaluation was applied to determine the final stereochemistry for 1 and 2. The biosynthesis pathway of 1 and 2 was proposed. 1 has potential on anti-Gram-negative bacteria. Both 1 and 2 exhibited a significant impact on anti-H1299 cells. Compounds 3–7 showed moderate cancer cell lethality and significant anti-inflammatory activities.

show abstract

3-O-Methylquercetin from Achyrocline satureioides—cytotoxic activity against A375-derived human melanoma cell lines and its incorporation into cyclodextrins-hydrogels for topical administration

Cited by 8 publications

References 60 publications

Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Gel Formulations for Topical Treatment of Skin Cancer: A Review

Achyrophenols A–F: Polycyclic Polyphenol Lactone Skeletons and a Nor-Ursane-Type Triterpenoid from Achyrocline Satureioides

Contact Info

Product

Resources

About