A new isoflavanone from the trunk of <i>Horsfieldia pandurifolia</i>

Ma, Qin; Liu, Yujiao; Zhan, Rui; Chen, Ye‐Gao

doi:10.1080/14786419.2015.1043554

Cited by 20 publications

(3 citation statements)

References 23 publications

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“…This substance showed a great difference in optical rotation value ([α] 20 D +44.0, MeOH) when compared to compound 1 ([α] 22 D −184.6, MeOH), confirming that 1 has a new structure . A few other coumaronochromone analogues bearing a hydroxy group at the C-3 position have been reported from several plant sources, but their stereostructures have not been reported. − This is the first study to determine the absolute configuration of a 3-hydroxycoumaronochromone derivative. The absolute configuration at the C-2 and C-3 positions of 1 was determined through comparison between the experimental and calculated electronic circular dichroism (ECD) spectra.…”

Section: Resultsmentioning

confidence: 59%

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

et al. 2018

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Apios americana is an important food crop producing edible tubers with high nutritional and medicinal values and is widely cultivated in many countries. Despite its usefulness, research on its secondary metabolites and biological activities has been limited. In the present study, a new coumaronochromone, (2 R,3 S)-3,7,4'-trihydroxy-5-methoxycoumaronochromone (1), and two new isoflavone glucosides, 7,2',4'-trihydroxy-5-methoxyisoflavone-4'- O-β-d-glucopyranoside (3) and 5,7,4'-trihydroxyisoflavone-7- O-β-d-gentiotrioside (5), were isolated from the tubers of A. americana via chromatographic separation. Seventeen known compounds (2, 4, and 6-20) were also obtained from this plant part. The chemical structures of 1, 3, and 5 were determined by the interpretation of spectroscopic data. The absolute structure of the new compound 1 was established from experimental and calculated electronic circular dichroism spectra. This is the first study to determine the absolute configuration of a 3-hydroxycoumaronochromone derivative. The potential anti-inflammatory activity of the 20 isolates obtained was evaluated by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Among the isolates, seven compounds (1, 3, 6-8, 15, and 20) showed substantial inhibition of nitric oxide production in RAW 264.7 cells, with the most active being compound 1 (IC value of 0.38 ± 0.04 μM).

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Section: Resultsmentioning

confidence: 59%

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

et al. 2018

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“…To determine the overlapping peaks at δ H 6.88–6.94 ppm, the 13 C NMR and 2D NMR experiments (Figures S1–S3), including heteronuclear single-quantum correlation (HSQC) and heteronuclear multiple-bond correlation (HMBC), were then conducted. On the basis of these results, genistein was identified [17] from the genistein-containing subfractions (D-4 and D-5). Bioactive fractions, together with the active ingredient, were rapidly obtained from the combination of bioactivity-guided fractionation and NMR-based identification of the UCME EtOAc-soluble fraction.…”

Section: Resultsmentioning

confidence: 99%

Bioactivity-Guided Fractionation and NMR-Based Identification of the Immunomodulatory Isoflavone from the Roots of Uraria crinita (L.) Desv. ex DC

Chan

Liu

et al. 2019

Foods

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Uraria crinita is used as a functional food ingredient. Little is known about the association between its immunomodulatory activity and its metabolites. We applied a precise strategy for screening metabolites using immunomodulatory fractions from a U. crinata root methanolic extract (UCME) in combination with bioactivity-guided fractionation and NMR-based identification. The fractions from UCME were evaluated in terms of their inhibitory activity against the production of pro-inflammatory cytokines (IL-6 and TNF-α) by lipopolysaccharide (LPS)-stimulated mouse bone marrow-derived dendritic cells (BMDC). The role of the isoflavone genistein was indicated by the 1H NMR profiling of immunomodulatory subfractions (D-4 and D-5) and supported by the result that genistein-knockout subfractions (D-4 w/o and D-5 w/o) had a lower inhibitory activity compared to genistein-containing subfractions. This study suggests that genistein contributes to the immunomodulatory activity of UCME and will help in the standardization of functional food.

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“…Tabla 18.Comparación de los desplazamientos químicos del compuesto Av5 con los de la luteolina (Ismail et al , 2014;Ma et al En la Tabla 20 y Figura 105 se muestran los promedios de los porcentajes de inhibición de la inflamación en los 6 grupos tratados en los tiempos: 1, 3, 5 y 7 horas de experimentación. FCHCl3 Av presentó los mayores porcentajes de inhibición a la primera hora después de comenzar el estudio (61,98%) y los valores menores a la séptima hora de seguimiento (68,94%).…”

Section: Elucidación Estructural De Av5unclassified

Estudio fitoquímico y screening de la actividad biológica de las especies Conyza trihecatactis y Ageratina vacciniaefolia

Muñoz¹

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Este trabajo se desarrolló teniendo en cuenta dos aspectos fundamentales: químico y biológico. El aspecto químico involucró procesos de extracción, fraccionamiento, aislamiento y purificación de los metabolitos secundarios presentes en las partes aéreas de las especies vegetales estudiadas; y en el aspecto biológico, los extractos etanólicos completos y las fracciones obtenidas se les evaluó la actividad antiinflamatoria (método de inducción de inflamación con -carragenina), la actividad citotóxica (método del MTT), la capacidad antioxidante (método del DPPH) con cuantificación de fenoles (método Folin-Ciocaulteu) y la toxicidad aguda en Artemia salina.

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A new isoflavanone from the trunk of Horsfieldia pandurifolia

Cited by 20 publications

References 23 publications

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Bioactivity-Guided Fractionation and NMR-Based Identification of the Immunomodulatory Isoflavone from the Roots of Uraria crinita (L.) Desv. ex DC

Estudio fitoquímico y screening de la actividad biológica de las especies Conyza trihecatactis y Ageratina vacciniaefolia

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