Synthesis and evaluation of berberine derivatives and analogs as potential antiacetylcholinesterase and antioxidant agents

Roselli, Mariagrazia; Cavalluzzi, Maria Maddalena; Bruno, Claudio; Lovece, Angelo; Carocci, Alessia; Franchini, Carlo; Habtemariam, Solomon; Lentini, Giovanni

doi:10.1016/j.phytol.2016.10.005

Cited by 25 publications

(22 citation statements)

References 40 publications

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“…24 Two BBR analogs were found to be good acetylcholinesterase inhibitors and more potent than BBR as radical scavengers. 25 Three synthesized BBR derivatives were found to induce a stronger effect of cell cycle arrest and cell death through apoptosis. 26 Moreover, a study reported the hypoglycemic activity of modified BBR.…”

Section: Introductionmentioning

confidence: 99%

Berberine and its structural analogs have differing effects on functional profiles of individual gut microbiomes

Zhang

et al. 2020

Gut Microbes

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The understanding of the effects of compounds on the gut microbiome is limited. In particular, it is unclear whether structurally similar compounds would have similar or distinct effects on the gut microbiome. Here, we selected berberine (BBR), an isoquinoline quaternary alkaloid, and 16 structural analogs and evaluated their effects on seven individual gut microbiomes cultured in vitro. The responses of the individual microbiomes were evaluated by metaproteomic profiles and by assessing butyrate production. We show that both interindividual differences and compound treatments significantly contributed to the variance of metaproteomic profiles. BBR and eight analogs led to changes in proteins involved in microbial defense and stress responses and enrichment of proteins from Verrucomicrobia, Proteobacteria, and Bacteroidetes phyla. It also led to a decrease in proteins from the Firmicutes phylum and its Clostridiales order which correlated to decrease proteins involved in the butyrate production pathway and butyrate concentration. Three of the compounds, sanguinarine, chelerythrine, and ethoxysanguinarine, activated bacterial protective mechanisms, enriched Proteobacteria, increased opacity proteins, and markedly reduced butyrate production. Dihydroberberine had a similar function to BBR in enriching the Akkermansia genus. In addition, it showed less overall adverse impacts on the functionality of the gut microbiome, including a better maintenance of the butyrate level. Our study shows that ex vivo microbiome assay can assess differential regulating effects of compounds with subtle differences and reveals that compound analogs can have distinct effects on the microbiome.

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Section: Introductionmentioning

confidence: 99%

Berberine and its structural analogs have differing effects on functional profiles of individual gut microbiomes

Zhang

et al. 2020

Gut Microbes

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“…As with the crude plant extracts, the number of natural products belonging to the various structural classes that offer neuroprotection under neurodegenerative conditions are staggeringly high [76]. Numerous review articles, including those on phenolic acids [77], flavonoids [78,79,80,81,82,83], alkaloids [83,84], monoterpenoids [85], and diterpenoids [86], provide a list with therapeutic promise for AD. The various classes of compounds that have been shown to target Aβ aggregations and prevent Aβ neurotoxicity, for example, include β-sheet-binding dyes such as Chrysamine G [87]; oligopeptides [88,89,90,91,92]; and polyphenols such as curcumin, myricetin, morin, quercetin, kaempferol (+)-catechin, (−)-epicatechin, nordihydroguaiaretic acid (Figure 4), and tannic acid [93,94,95].…”

Section: Multi-target Approach—lessons From Natural Productsmentioning

confidence: 99%

Natural Products in Alzheimer’s Disease Therapy: Would Old Therapeutic Approaches Fix the Broken Promise of Modern Medicines?

Habtemariam

2019

Molecules

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Despite extensive progress in understanding the pathology of Alzheimer’s disease (AD) over the last 50 years, clinical trials based on the amyloid–beta (Aβ) hypothesis have kept failing in late stage human trials. As a result, just four old drugs of limited clinical outcomes and numerous side effects are currently used for AD therapy. This article assesses the common pharmacological targets and therapeutic principles for current and future drugs. It also underlines the merits of natural products acting through a polytherapeutic approach over a monotherapy option of AD therapy. Multi-targeting approaches through general antioxidant and anti-inflammatory mechanisms coupled with specific receptor and/or enzyme-mediated effects in neuroprotection, neuroregeneration, and other rational perspectives of novel drug discovery are emphasized.

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“…Total free radical scavenging capacity of the extracts using the stable DPPH radical was determined according to the previously reported procedure [43,44], with some modifications. A calibration curve (R 2 = 0.9934) was prepared using different concentrations of gallic acid in methanol (0-4 µg/mL).…”

Section: Dpph Assaymentioning

confidence: 99%

Optimization of Microwave-Assisted Extraction of Antioxidants from Bamboo Shoots of Phyllostachys pubescens

et al. 2020

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Bamboo is a well-known medicinal plant in Southeast Asia that recently has attracted attention for its high polyphenol content and its medical and nutraceutical applications. In this work, polyphenols have been recovered for the first time by microwave-assisted extraction (MAE) from an unusual Italian cultivar of Phyllostachys pubescens bamboo shoots. The effects of three independent variables, such as extraction time, temperature, and solid/liquid ratio, on polyphenol recovery yield were investigated and successfully optimized through the response surface methodology. We demonstrated that MAE is an excellent polyphenols extraction technique from bamboo shoots because the total phenolic content obtained under microwave irradiation optimal conditions (4 min at 105 °C with 6.25 mg/mL ratio) was about eight-fold higher than that obtained with the conventional extraction method. Furthermore, higher total flavonoid content was also obtained under MAE. Consistent with these results, MAE enhanced the extract antioxidant properties with significant improved DPPH, ABTS, and FRAP scavenging ability. Therefore, this innovative extraction process enhances the recovery of biologically active compounds from Phyllostachys pubescens bamboo shoots with a dramatic reduction of time and energy consumption, which paves the way for its industrial application in functional food production.

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Synthesis and evaluation of berberine derivatives and analogs as potential antiacetylcholinesterase and antioxidant agents

Cited by 25 publications

References 40 publications

Berberine and its structural analogs have differing effects on functional profiles of individual gut microbiomes

Berberine and its structural analogs have differing effects on functional profiles of individual gut microbiomes

Natural Products in Alzheimer’s Disease Therapy: Would Old Therapeutic Approaches Fix the Broken Promise of Modern Medicines?

Optimization of Microwave-Assisted Extraction of Antioxidants from Bamboo Shoots of Phyllostachys pubescens

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