Studies of the Egyptian Traditional Folk Medicines. IV. New Isoflavonoid Isolated from Egyptian Licorice

Baba, M.; Sumi, Sakiko; Iwasaki, Noriaki; Hao, Kai; Sakano, Masami; Okada, Yoshihito; Okuyama, Toru

doi:10.3987/com-08-11462

Cited by 8 publications

(9 citation statements)

References 4 publications

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“…Licorice refers to the roots from Glycyrrhiza glabra and have been traditionally used in herbal medicine for over 4000 years 11, 12. In the past decades, extensive chemical studies have resulted in the identification of many flavonoids in the roots of Glycyrrhiza glabra , including about 75 prenylated flavonoids 13–22…”

mentioning

confidence: 99%

A rapid screening method for prenylated flavonoids with ultra‐high‐performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts

Simons

Vincken

Bakx

et al. 2009

Rapid Comm Mass Spectrometry

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Due to their substitution with an isoprenoid group, prenylated flavonoids have an increased affinity for biological membranes and target proteins, enhancing their potential bioactivity. Although many prenylated flavonoids have been described, there are no methods that specifically screen for their presence in complex mixtures, prior to purification. We describe a method based on ultra-high-performance liquid chromatography (UHPLC) with electrospray ionisation mass spectrometry (ESI-MS) that allows rapid screening for prenylated flavonoids in multi-component plant extracts. Identification of the prenylated flavonoids is based on screening for neutral losses of 42 u and 56 u in the positive-ion mode MS(2) and MS(3) spectra within the MS chromatograms. In addition, this method discriminates between a prenyl chain and a ring-closed prenyl (pyran ring), based on the ratio of the relative abundances of the ions that lose 42 u and 56 u (42:56). The application of this screening method on a 70% aq. ethanol, ethanol and ethyl acetate extract of the roots of Glycyrrhiza glabra indicated the presence of 70 mono- and di-prenylated flavonoids. In addition, of each prenylated flavonoid the type of prenylation, chain or pyran ring was determined.

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mentioning

confidence: 99%

A rapid screening method for prenylated flavonoids with ultra‐high‐performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts

Simons

Vincken

Bakx

et al. 2009

Rapid Comm Mass Spectrometry

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“…The most abundant compounds in the selected fractions 2 and 7 were already known characteristic licorice metabolites. Their identity was confirmed through a dereplication process combining 1D, 1 H NMR (at 600 and/or 900 MHz), MS analyses and a comparison of previously published data [20][21][22][23][24]. Hence, licochalcone B [21], liquiritigenin, echinatin, and licoflavone A [23] were the most abundant compounds in fraction 2.…”

Section: Resultsmentioning

confidence: 84%

“…Hence, licochalcone B [21], liquiritigenin, echinatin, and licoflavone A [23] were the most abundant compounds in fraction 2. Whereas, licoisoflavone A, glabrone [20] and licoflavone B, also called prenyllicoflavone A [22], were the most abundant compounds in fraction 7 (Supplementary Material S4, and raw NMR data at doi:10.7910/DVN/DFAVTE). The weight recovery calculated for compounds 1 and 2 were 0.06 and 0.03% w/w (weight compound/weight crude extract), respectively, clearly indicating that both compounds were found in trace amounts in the original extract.…”

Section: Resultsmentioning

confidence: 99%

Isolation and structural characterization of dihydrobenzofuran congeners of licochalcone A

et al. 2017

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In an effort to explore the residual complexity of naturally occurring chalcones from the roots of Glycyrrhiza inflata (Fabaceae), two new licochalcone A (LicA) derivatives were isolated as trace metabolites from enriched fractions. Both constituents contain a dihydrofuran moiety linked to carbons C-4 and C-5 of the retrochalcone core. Compound 1 (LicAF1) represents a new chemical entity, whereas compound 2 (LicAF2) has previously been reported as a Lewis acid catalyzed rearrangement of LicA. Evaluation of chirality revealed that both dihydrofuran derivatives existed as a mixture of R and S enantiomers. Interestingly, when solutions were exposed to sunlight, both dihydrofuran retrochalcones, initially isolated as trans isomers, were found to rapidly isomerize yielding trans and cis isomers. Analysis of the 1D 1H NMR spectra of the photolysis products revealed the presence of two sets of proton resonances ascribed to each of the geometric isomers. An up-field shift of all proton resonances arising from the cis isomer was observed, suggesting that anisotropic shielding effects were introduced through an overall perturbation of the 3-dimensional structure upon photoisomerization. Similar up-field shifts were observed in the 13C spectrum of the cis isomer, except for the C=O, C-α, and C-6 carbons, which experienced downfield shifts. Analogous NMR results were observed for LicA. Hence, the results presented herein encompass the isolation and full characterization of LicAF analogs 1 and 2, and observations of their trans-to-cis photoisomerization through the systematic analysis of their NMR spectra.

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“…Glycyrrhiza glabra. (Shristensen, S. Broegger; Glycyrrhiza, G. glabra Baba, Masaki;Sumi et al 2008) 6a,11a-6a,11a-dehydroglyceollin (18)…”

Section: Glycyrrhiza Glabramentioning

confidence: 99%

“…2008 Glycyrrha (glabra) isoglabrone (Baba, Masaki;Sumi, Sakiko;Iwasaki, Noriaki;Kai, Hisahiro;Sakano, Masami;Okada, Yoshihito;Okuyama, Toru, Heterocycles (2008), 5(12), 3085-3089).…”

Section: Hemileiocarpin (16)mentioning

confidence: 99%

Απομόνωση φυσικών παραγώγων με δράση ανασταλτική των κυκλινοεξαρτώμενων κινασών (CDK’s) σύνθεση αναλόγων τους και μελέτη των βιολογικών ιδιοτήτων τους

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Studies of the Egyptian Traditional Folk Medicines. IV. New Isoflavonoid Isolated from Egyptian Licorice

Cited by 8 publications

References 4 publications

A rapid screening method for prenylated flavonoids with ultra‐high‐performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts

A rapid screening method for prenylated flavonoids with ultra‐high‐performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts

Isolation and structural characterization of dihydrobenzofuran congeners of licochalcone A

Απομόνωση φυσικών παραγώγων με δράση ανασταλτική των κυκλινοεξαρτώμενων κινασών (CDK’s) σύνθεση αναλόγων τους και μελέτη των βιολογικών ιδιοτήτων τους

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