A Non-Centrosymmetric Polymorph of 5-Hydroxy-7-Methoxy-2-Phenylchroman-4-One

Brito, Iván; Simirgiotis, Mario J.; Brito, Anghel; Werner, M.; Bórquez, Jorge; Winterhalter, Peter; Cárdenas, Alejandro

doi:10.4067/s0717-97072015000100020

Cited by 7 publications

(7 citation statements)

References 13 publications

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“…These data are in agreement with the literature [35,40]. Furthermore the X-ray crystal structure of this compound was already published by us [41].…”

Section: Fast Hpccc Isolation Of Major Compounds In N Ramosissima Mesupporting

confidence: 93%

Fast Isolation of Flavonoids from the Endemic Species Nolana ramosissima I.M. Johnst and Its Endothelium-Independent Relaxation Effect in Rat Aorta

et al. 2020

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The infusion of the desertic plant Nolana ramosissima I.M. Johnst showed vascular smooth muscle relaxation in rat aorta and the presence of several phenolic compounds, which were detected by high resolution UHPLC-Orbitrap-HESI-MS. In addition, five flavonoids were rapidly isolated from a methanolic extract using high-performance counter-current chromatography (HPCCC). The N. ramosissima extract showed endothelium-independent relaxation effect in rat aorta. Sixty-one compounds were detected in the infusion, mainly glycosylated flavonoids, flavanones and several oxylipins, suggesting that a synergistic effect between the compounds in the extracts could be responsible for the relaxation activity. Vascular activity experiments were done in isolated organ bath. In rat aorta, a nitric oxide inhibitor did not prevent the relaxation effects of the extract; however, a selective guanylyl cyclase inhibitor partially blunted this effect. The compound 5,3 -dihydroxy-4 7-dimethoxyflavone presented higher relaxation effect than 100 µg/mL of N. ramosissima extract. The extract and the isolated metabolites from N. ramosissima can show relaxation effects on rat aorta by a mechanism that is independent of the endothelium.

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“…These data are in agreement with the literature [35,40]. Furthermore the X-ray crystal structure of this compound was already published by us [41].…”

Section: Fast Hpccc Isolation Of Major Compounds In N Ramosissima Mesupporting

confidence: 93%

Fast Isolation of Flavonoids from the Endemic Species Nolana ramosissima I.M. Johnst and Its Endothelium-Independent Relaxation Effect in Rat Aorta

et al. 2020

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“…3 for both structures and both levels of calculations. On the other hand, the phenyl group also has free rotation between 10º and 95º at room temperature, which may explain first, the discrepancy between experimental and theoretical structures and second, all polymorphic structures found for the structure II and informed in the literature [23][24][25]. …”

Section: Geometries and Energetic Stabilitymentioning

confidence: 99%

“…However, the other two structures are derived from the second one and differing essentially by the orientation of the phenyl group with respect to the plane of chromon ring of the compound [24,25]. X-ray crystallographic data of three structures for second compound reported the torsion angles of phenyl group were 24.8º, 38.5º [23,24], and 85.6º [25]. For the first structure had been reported a torsion angle of phenyl group was 71.5º.…”

Section: Introductionmentioning

confidence: 99%

Electronic and Structural Properties of 5-Hydroxy-7-Metoxyflavanone: A Theoretical Approach

Padilla-Campos

Zárate

2016

J. Chil. Chem. Soc.

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Electronic and structural properties of two polymorphic modifications of 5-hydroxy-7-methoxyflavanone (pinostrobin) were theoretically investigated and compared with experimental crystallographic data. In the literature, four polymorphic modifications of pinostrobin had been reported. The present study has established that only two of them are relevant as they differ only in the position of the methoxy group whereas other structures are derived from the rotation of the phenyl group. Both structures differ in about 1.5 kJ/mol, but the activation energy of methoxy torsion was greater than 16 kJ/mol. In addition, both have similar electronic structures but it was established with slight differences in reactivity.

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“…This plant is well recognized as an important source of diterpenes bearing the mulinane skeleton with interesting biological activities 2 . The relative stereochemistry of the title compound was assigned by spectroscopic data and by chemical transformations 3 . In this paper we report the absolute configuration of the title compound which has been determined from the refinement of the Flack parameter 15 , x = 0.05 (11), which indicate that the correct configuration had been assigned against 925, CuKα Bijvoet pairs.…”

Section: Introductionmentioning

confidence: 99%

Absolute Configuration of Mulinolic Acid

Brito

Bórquez

Huarote

et al. 2017

J. Chil. Chem. Soc.

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The structure of this mulinolic acid consists of a mulinane skeleton and the corresponding isopropyl, methyl, carboxyl and methyl groups at C3, C8, C5, C13, respectively, which are β-oriented, whereas the hydroxyl group at C13 is α-oriented. The cyclopentane (A), ciclohexane (B) and cicloheptene (C) rings are trans (A/B) and (B/C) cis fused, and in an envelope, chair, and twist conformation respectively.In the crystal the molecules are linked by two intermolecular OH⋅⋅⋅O hydrogen bond forming bidimensional supramolecular structures with graph-set notation R4 4 (12), R4 4 (40), R6 6 (46) and C4 4 (46). The absolute configuration of the title compound has been determined from the refinement of the Flack parameter 16 . On this basis the absolute configuration was assigned as C3R, C5S, C8S, C9S, C10S and C13R.

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A Non-Centrosymmetric Polymorph of 5-Hydroxy-7-Methoxy-2-Phenylchroman-4-One

Cited by 7 publications

References 13 publications

Fast Isolation of Flavonoids from the Endemic Species Nolana ramosissima I.M. Johnst and Its Endothelium-Independent Relaxation Effect in Rat Aorta

Fast Isolation of Flavonoids from the Endemic Species Nolana ramosissima I.M. Johnst and Its Endothelium-Independent Relaxation Effect in Rat Aorta

Electronic and Structural Properties of 5-Hydroxy-7-Metoxyflavanone: A Theoretical Approach

Absolute Configuration of Mulinolic Acid

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