Theoretical study of cyclization of 2′-hydroxychalcone

Yamı́n, Lázaro J.; Blanco, Susana; Luco, Juan M.; Ferretti, F.H.

doi:10.1016/s0166-1280(96)04776-8

Cited by 16 publications

(12 citation statements)

References 11 publications

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“…Isomerization of chalcones to flavanones is a well established chemical phenomenon (Figure 1) [54], [55], [56], [57]. However, this conversion has often been neglected when studying the biological properties of chalcone/flavanone pairs such as LigC/LigF in bioassays.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of Estrogenic Activity of Licorice Species in Comparison with Hops Used in Botanicals for Menopausal Symptoms

et al. 2013

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The increased cancer risk associated with hormone therapies has encouraged many women to seek non-hormonal alternatives including botanical supplements such as hops (Humulus lupulus) and licorice (Glycyrrhiza spec.) to manage menopausal symptoms. Previous studies have shown estrogenic properties for hops, likely due to the presence of 8-prenylnarigenin, and chemopreventive effects mainly attributed to xanthohumol. Similarly, a combination of estrogenic and chemopreventive properties has been reported for various Glycyrrhiza species. The major goal of the current study was to evaluate the potential estrogenic effects of three licorice species (Glycyrrhiza glabra, G. uralensis, and G. inflata) in comparison with hops. Extracts of Glycyrrhiza species and spent hops induced estrogen responsive alkaline phosphatase activity in endometrial cancer cells, estrogen responsive element (ERE)-luciferase in MCF-7 cells, and Tff1 mRNA in T47D cells. The estrogenic activity decreased in the order H. lupulus > G. uralensis > G. inflata > G. glabra. Liquiritigenin was found to be the principle phytoestrogen of the licorice extracts; however, it exhibited lower estrogenic effects compared to 8-prenylnaringenin in functional assays. Isoliquiritigenin, the precursor chalcone of liquiritigenin, demonstrated significant estrogenic activities while xanthohumol, a metabolic precursor of 8-prenylnaringenin, was not estrogenic. Liquiritigenin showed ERβ selectivity in competitive binding assay and isoliquiritigenin was equipotent for ER subtypes. The estrogenic activity of isoliquiritigenin could be the result of its cyclization to liquiritigenin under physiological conditions. 8-Prenylnaringenin had nanomolar estrogenic potency without ER selectivity while xanthohumol did not bind ERs. These data demonstrated that Glycyrrhiza species with different contents of liquiritigenin have various levels of estrogenic activities, suggesting the importance of precise labeling of botanical supplements. Although hops shows strong estrogenic properties via ERα, licorice might have different estrogenic activities due to its ERβ selectivity, partial estrogen agonist activity, and non-enzymatic conversion of isoliquiritigenin to liquiritigenin.

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Section: Discussionmentioning

confidence: 99%

Evaluation of Estrogenic Activity of Licorice Species in Comparison with Hops Used in Botanicals for Menopausal Symptoms

et al. 2013

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“…Chalcones undergo rapid cyclization into flavanones at neutral and lower acidic pH whereas flavones isomers undergo a reversible reaction to their chalcones at basic pH. This interconversion between chalcone and flavanone represents temperature dependent isomerization and racemization of these active compounds ( Furlong and Nudelman, 1988 ; Miles and Main, 1989 ; Nudelman and Furlong, 1991 ; Cisak and Mielczarek, 1992 ; Yamín et al, 1997 ; Andújar et al, 2003 ). Interestingly, these chemical conditions match the cell culture-based assays also.…”

Section: Isoliquiritigenin and Liquiritigeninmentioning

confidence: 99%

Phytochemical and Pharmacological Role of Liquiritigenin and Isoliquiritigenin From Radix Glycyrrhizae in Human Health and Disease Models

Mahesh

Kim

Lee

et al. 2018

Front. Aging Neurosci.

136

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The increasing lifespan in developed countries results in age-associated chronic diseases. Biological aging is a complex process associated with accumulated cellular damage by environmental or genetic factors with increasing age. Aging results in marked changes in brain structure and function. Age-related neurodegenerative diseases and disorders (NDDs) represent an ever-growing socioeconomic challenge and lead to an overall reduction in quality of life around the world. Alzheimer’s disease (AD) and Parkinson’s disease (PD) are most common degenerative neurological disorders of the central nervous system (CNS) in aging process. The low levels of acetylcholine and dopamine are major neuropathological feature of NDDs in addition to oxidative stress, intracellular calcium ion imbalance, mitochondrial dysfunction, ubiquitin-proteasome system impairment and endoplasmic reticulum stress. Current treatments minimally influence these diseases and are ineffective in curing the multifunctional pathological mechanisms. Synthetic neuroprotective agents sometimes have negative reactions as an adverse effect in humans. Recently, numerous ethnobotanical studies have reported that herbal medicines for the treatment or prevention of NDDs are significantly better than synthetic drug treatment. Medicinal herbs have traditionally been used around the world for centuries. Radix Glycyrrhizae (RG) is the dried roots and rhizomes of Glycyrrhiza uralensis or G. glabra or G. inflata from the Leguminosae/Fabaceae family. It has been used for centuries in traditional medicine as a life enhancer, for the treatment of coughs and influenza, and for detoxification. Diverse chemical constituents from RG have reported including flavanones, chalcones, triterpenoid saponins, coumarines, and other glycosides. Among them, flavanone liquiritigenin (LG) and its precursor and isomer chalcone isoliquiritigenin (ILG) are the main bioactive constituents of RG. In the present review, we summarize evidence in the literature on the structure and phytochemical properties and pharmacological applications of LG and ILG in age-related diseases to establish new therapeutics to improve human health and lifespan.

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“…This is reasonable because cyclization of 2 0 -hydroxychalcones to flavanones has been reported in a number of studies demonstrating an intramolecular equilibrium being present between a flavanone-type and a chalcone-type molecular ion. [38][39][40][41] 3,3 0 ,4,4 0 -Tetrahydroxy-6-methoxychalcone (7), licochalcone B (18) and echinatin (29) were identified by comparison with the corresponding reference standards. In the MS 2 experiment, 7, 18 and 29 underwent characteristic X B À fragmentation to produce the ions at m/z 191, 191 and 175, respectively.…”

Section: Chalconesmentioning

confidence: 99%

Characterization of fifty‐one flavonoids in a Chinese herbal prescription Longdan Xiegan Decoction by high‐performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry and photodiode array detection

Wang

Yang

et al. 2008

Rapid Comm Mass Spectrometry

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High-performance liquid chromatography coupled to electrospray ionization (ESI) tandem mass spectrometry and photodiode array detection (HPLC-DAD-ESI-MS(n)) was developed to identify and characterize the flavonoids in a Chinese formulated preparation, Longdan Xiegan Decoction (LXD). In total, fifty-one flavonoids (27 flavones, 10 flavanones, 7 chalcones, 5 flavonols and 2 isoflavones) were characterized. Eighteen compounds among them including a newly detected flavonoid, naringin, from the ingredient herbs, were unambiguously determined by comparing the retention times (t(R)), UV spectral data and mass fragmentation behaviors with those of the reference compounds. Another thirty-three compounds were tentatively identified by referencing to the reported data of their UV and MS spectra. The ESI-MS/MS fragmentation behavior of flavones (OMe-substituted, O-glycosides, C-glycosides), chalcones, flavonols and their appropriate characteristic pathways were proposed. In negative ion ESI-MS all the flavonoids yielded prominent [M--H](-) ions in the first order mass spectra. Fragmentation with a loss of mass of 15 Da (CH(3)), 18 Da (H(2)O), 28 Da (CO), 44 Da (CO(2)), 56 Da (2CO) and the residues of glucose and glucuronic acid observed in the MS/MS spectra were useful for aiding the structural identification of the flavonoids investigated.

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Theoretical study of cyclization of 2′-hydroxychalcone

Cited by 16 publications

References 11 publications

Evaluation of Estrogenic Activity of Licorice Species in Comparison with Hops Used in Botanicals for Menopausal Symptoms

Evaluation of Estrogenic Activity of Licorice Species in Comparison with Hops Used in Botanicals for Menopausal Symptoms

Phytochemical and Pharmacological Role of Liquiritigenin and Isoliquiritigenin From Radix Glycyrrhizae in Human Health and Disease Models

Characterization of fifty‐one flavonoids in a Chinese herbal prescription Longdan Xiegan Decoction by high‐performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry and photodiode array detection

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