Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale-up for the flavonoid Naringenin

Gaggeri, Raffaella; Rossi, Daniela; Collina, Simona; Mannucci, Barbara; Baierl, Marcel; Juza, Markus

doi:10.1016/j.chroma.2011.02.038

Cited by 57 publications

(37 citation statements)

References 26 publications

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“…(89) The HPLC enantioselective separation of (R/S)-naringenin, a chiral flavonoid found in several fruits juices has been performed on both analytical and (semi)-preparative scale using an amylose derived Chiralpak AD chiral stationary phase. (90) Five flavonoid including naringenin from Drynaria fortunei were isolated in another study. (91) Using various chromatographic methods, three fl avonoids including naringenin were isolated from the pollen of Typha angustata.…”

Section: Extraction and Isolation Techniques Of Naringeninmentioning

confidence: 99%

A Review on Pharmacological and Analytical Aspects of Naringenin

Patel

Singh

Patel

2014

Chin. J. Integr. Med.

181

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Flavonoids are a widely distributed group of phytochemicals having benzo-pyrone nucleus, and more than 4,000 different flavonoids have been described and categorized into flavonols, flavones, flavanones, isoflavones, catechins and anthocyanidins. Flavonoids occurs naturally in fruits, vegetables, nuts, and beverages such as coffee, tea, and red wine, as well as in medical herbs. Flavonoids are responsible for the different colors of plant parts and are important constituents of the human diet. Flavanoids have different pharmacological activities, such as antioxidant, anti-allergic, antibacterial, anti-inflammatory, antimutagenic and anticancer activity. Naringenin belongs to the flavanones and is mainly found in fruits (grapefruit and oranges) and vegetables. Pharmacologically, it has anticancer, antimutagenic, anti-inflammatory, antioxidant, antiproliferative and antiatherogenic activities. Naringenin is used for the treatments of osteoporosis, cancer and cardiovascular diseases, and showed lipid-lowering and insulin-like properties. In the present review, detailed pharmacological and analytical aspects of naringenin have been presented, which revealed the impressive pharmacological profile and the possible usefulness in the treatment of different types of diseases in the future. The information provided in this communication will act as an important source for development of effective medicines for the treatment of various disorders.

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Section: Extraction and Isolation Techniques Of Naringeninmentioning

confidence: 99%

A Review on Pharmacological and Analytical Aspects of Naringenin

Patel

Singh

Patel

2014

Chin. J. Integr. Med.

181

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“…Since the development of the first commercialized catalytic asymmetric synthesis of l ‐DOPA, enantioselective hydrogenation has played a relevant role in the preparation of chiral compounds, especially in industrial processes, and it is still one of the most reliable catalytic methods for the preparation of optically active molecules . Besides asymmetric synthesis, enantioselective HPLC resolution on CSPs has also been successfully employed for the isolation of enantiopure compounds, being a viable route for straightforward and rapid access to both enantiomers with high optical purity and yields . The determination of the absolute configuration of enantiopure compounds is then another unavoidable and complementary step to enantiopreparation, for which single‐crystal X‐ray diffraction is still considered the experimental technique of choice .…”

Section: Introductionmentioning

confidence: 99%

Studies on the Enantiomers of RC-33 as Neuroprotective Agents: Isolation, Configurational Assignment, and Preliminary Biological Profile

et al. 2013

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In this study we addressed the role of chirality in the biological activity of RC-33, recently studied by us in its racemic form. An asymmetric synthesis procedure was the first experiment, leading to the desired enantioenriched RC-33 but with an enantiomeric excess (ee) not good enough for supporting the in vitro investigation. An enantioselective high-performance liquid chromatography (HPLC) procedure was then successfully carried out, yielding both RC-33 enantiomers in amounts and optical purity suitable for the pharmacological study. The absolute configuration of pure enantiomers was easily assigned exploiting the asymmetric synthesis previously devised. As emerged in the preliminary in vitro biological investigation, (S)- and (R)-RC-33 possess a comparable affinity towards the σ1 receptor and a very a similar behavior in the calcium influx assay, resulting in an equally effective σ1 receptor agonist. Overall, the results obtained so far suggest that the interaction with the biological target is nonstereoselective and leads us to hypothesize that there is a lack of stereoselectivity in the biological activity of RC-33.

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“…Hence, compounds interacting with both the ES and the PAS of AChE could not only alleviate cognitive deficits associated with cholinergic neuron depletion but also inhibit Ab peptide aggregation. These so-called bivalent ligands are now being developed as a new avenue of AD therapeutic approach (Gaggeri et al, 2010(Gaggeri et al, , 2011Khan et al, 2011;Langjae et al, 2007;Martino et al, 2006Martino et al, , 2008Nisar et al, 2011). The PAS varies among AChEs and that from Torpedo californica, for example, consists of aromatic and carboxylic acid residues, Asp72, Tyr70, Tyr121, Trp279 and Phe290 (Szegletes et al, 1998).…”

Section: Resultsmentioning

confidence: 99%