Development of dihydrochalcone-functionalized gold nanoparticles for augmented antineoplastic activity

Payne, Jason; Badwaik, Vivek; Waghwani, Hitesh Kumar; Moolani, Harsh V; Tockstein, Sarah; Thompson, David H.; Rajalingam, Dakshinamurthy

doi:10.2147/ijn.s143506

Cited by 22 publications

(10 citation statements)

References 37 publications

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“…From natural sources, dihydrochalcones are isolated as aglycones and their glycosides.Most extensively described dihydrochalcones are phloretin and its 2 -O-glucoside named phloridzin, isolated from a genus of small trees and shrubs Malus. Many studies proved numerous biological activities of phloridzin, such as anti-diabetic, anti-inflammatory, anti-oxidant, antihyperglycemic, antimicrobial, cardio-and hepatoprotective, anti-obesity and others [18][19][20][21][22]. Similar activities have been reported for phloretin [23].…”

Section: Introductionsupporting

confidence: 55%

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

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Flavonoids, including chalcones, are more stable and bioavailable in the form of glycosylated and methylated derivatives. The combined chemical and biotechnological methods can be applied to obtain such compounds. In the present study, 2′-hydroxy-2-methylchalcone was synthesized and biotransformed in the cultures of entomopathogenic filamentous fungi Beauveria bassiana KCH J1.5, Isaria fumosorosea KCH J2 and Isaria farinosa KCH J2.6, which have been known for their extensive enzymatic system and ability to perform glycosylation of flavonoids. As a result, five new glycosylated dihydrochalcones were obtained. Biotransformation of 2′-hydroxy-2-methylchalcone by B. bassiana KCH J1.5 resulted in four glycosylated dihydrochalcones: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′-hydroxy-2-hydroxymethyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, and 2′,4-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. In the culture of I. fumosorosea KCH J2 only one product was formed—3-hydroxy-2-methyldihydrochalcone 2′-O-β-d-(4″-O-methyl)-glucopyranoside. Biotransformation performed by I. farinosa KCH J2.6 resulted in the formation of two products: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside and 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. The structures of all obtained products were established based on the NMR spectroscopy. All products mentioned above may be used in further studies as potentially bioactive compounds with improved stability and bioavailability. These compounds can be considered as flavor enhancers and potential sweeteners.

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Section: Introductionsupporting

confidence: 55%

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

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“…In general, the results showed that LSTE, F1, F2 and their Au NPs had the potential to be used as antidiabetic agents. Pure isolated phytochemicals have demonstrated activities against alpha-glucosidase in previous studies [47,48]. Recently, Etsassala et al [89] reported a strong antidiabetic activity of ten abietane diterpenes.…”

Section: In-vitro Antidiabetic Studiesmentioning

confidence: 97%

“…Furthermore, since no external stabilizers were employed, it could also be concluded that the same constituents were responsible for the stabilization of the nanoparticles (see Scheme 1). Many investigations concluded that polyphenols, which are abundant in plants, are associated with the reduction of metal salts when combined with plant extracts [47,48]. This may also explain why F1 and F2 (which contain similar functionality) were not only able to reduce gold to its zero-valence state but also formed Au NPs with very similar characteristics to that of the LSTE.…”

Section: Uv-visible Spectroscopic Analysismentioning

confidence: 99%

“…As far as we know, procyanidins have not been identified from the plant previously and no nanoparticle synthesis reported.Gold nanoparticles is one of the most widely used nanomaterials because of an array of interesting properties including the ease of its surface chemistry [40]. Among the importance of Au NPs is the ease of synthesis, characterization, surface modification, low toxicity, tunable surface plasmon resonance, biostability and biocompatibility [5,33,40,47,56,58]. The advantage that comes with these is the applications in biomedicals.…”

mentioning

confidence: 99%

“…The advantage that comes with these is the applications in biomedicals. Due to its small size, Au NPs can penetrate cells to interact with different molecules without causing damage making it the preferred candidate in drug delivery, cancer therapy among other applications [47,56].…”

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confidence: 99%

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Green Synthesis of Gold Nanoparticles Capped with Procyanidins from Leucosidea sericea as Potential Antidiabetic and Antioxidant Agents

et al. 2020

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In this study, procyanidins fractions of dimers and trimers (F1-F2) from the Leucosidea sericea total extract (LSTE) were investigated for their chemical constituents. The total extract and the procyanidins were employed in the synthesis of gold nanoparticles (Au NPs) and fully characterized. Au NPs of 6, 24 and 21 nm were obtained using LSTE, F1 and F2 respectively. Zeta potential and in vitro stability studies confirmed the stability of the particles. The enzymatic activity of LSTE, F1, F2 and their corresponding Au NPs showed strong inhibitory alpha-amylase activity where F1 Au NPs demonstrated the highest with IC 50 of 1.88 µg/mL. On the other hand, F2 Au NPs displayed the strongest alpha-glucosidase activity at 4.5 µg/mL. F2 and F2 Au NPs also demonstrated the highest antioxidant activity, 1834.0 ± 4.7 µM AAE/g and 1521.9 ± 3.0 µM TE/g respectively. The study revealed not only the ability of procyanidins dimers (F1 and F2) in forming biostable and bioactive Au NPs but also, a significant enhancement of the natural products activities, which could improve the smart delivery in future biomedical applications.Biomolecules 2020, 10, 452 2 of 24 applying nanoparticles through the green route is their biocompatibility [5]. Many green synthesized nanoparticles have demonstrated interesting biological activities [5,10] including antimicrobial and antidiabetic properties.Diabetes mellitus has undoubtedly become a serious health challenge. More worrisome is type II diabetes mellitus (T2DM), which accounts for 90% of diabetes mellitus. It occurs as a result of the inefficient processing of insulin [11]. As of 2017, the population of adults between the ages of 20 and 79 that suffered from diabetes was 425 million [12]. This is equivalent to 9.9% of the world's population [12]. By estimation, this disease would have drastically increased by 48% in 28 years if not properly managed [13]. Although drugs like miglitol, vigliobose as well as acarbose are available in the market, they are costly and their continuous use is associated with side effects like diarrhea, dropsy, heart failure, damage to the liver, weight gain, abdominal pain, hyperglycemia, and flatulence, necessitating the need for more potent and newer remedies [14][15][16].It is well established that bioactive compounds in various plants possess significant effects in delaying and management of T2DM [17]. Extracts from different plants have been reported as alpha-glucosidase and alpha-amylase inhibitors [18][19][20][21][22][23][24][25][26][27]. Additionally, biologically synthesized Au NPs using plant extracts showed interesting antidiabetic activity. The extracts of Chamalcostus cuspidatus [28], Gymnema sylvestre [29], Cassia fistula stem bark [30], Hericium erinaceus [31], Turbinaria conoides [32], Sambucus nigra [33] and Sargassum swartzi [34] displayed antidiabetic activities in various investigations. Silver/gold NPs of Ocimum basilicum [35] and cinnamon extract [36] also lowers glucose levels. The use of single molecules as reducing/stabilizing agents for ...

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Surface‐Functionalized Gold Nanoparticles for Environmental Remediation

Thangadurai

Manjubaashini

Nataraj

2022

Nanotechnology for Environmental Remediation

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Development of dihydrochalcone-functionalized gold nanoparticles for augmented antineoplastic activity

Cited by 22 publications

References 37 publications

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Green Synthesis of Gold Nanoparticles Capped with Procyanidins from Leucosidea sericea as Potential Antidiabetic and Antioxidant Agents

Surface‐Functionalized Gold Nanoparticles for Environmental Remediation

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