New phenolics from the wood of Casearia grewiifolia

Rayanil, Kanok‐on; Nimnoun, Chanisara; Tuntiwachwuttikul, Pittaya

doi:10.1016/j.phytol.2011.09.007

Cited by 18 publications

(12 citation statements)

References 23 publications

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“…A comparison of NMR data of 3 with that of 2 indicated that the significant difference was the coupling constant between H-7 and H-8 ( J 7,8 = 9.3 Hz of 2 and J 7,8 = 6.6 Hz of 3 ) ( Table 1 ). These findings suggested that 3 was a stereoisomer of 2 , and it was determined to be erythro form in comparison with structurally related compounds reported in literatures 27 30 . Interestingly, compound 3 was also found to be a racemic mixture, and was further resolved to yield 3a (4.5 mg) and 3b (4.1 mg) over HPLC using a chiral column.…”

Section: Resultssupporting

confidence: 71%

Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Lai

Zhou

et al. 2016

Sci Rep

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Eight pairs of enantiomeric neolignans, norlignans, and sesquineolignans (1a/1b–8a/8b), together with five known neolignans (9a/9b and 10–12), have been isolated from 70% acetone extract of the whole plants of Phyllanthus glaucus Wall. (Euphorbiaceae). The racemic or partial racemic mixtures were successfully separated by chiral HPLC using different types of chiral columns with various mobile phases. Their structures were elucidated on the basis of extensive spectroscopic data. The absolute configurations of 2a/2b were determined by computational analysis of their electronic circular dichroism (ECD) spectrum, and the absolute configurations of other isolates were ascertained by comparing their experimental ECD spectra and optical rotation values with those of structure-relevant compounds reported in literatures. Compounds 4a/4b featured unique sesquineolignan skeletons with a novel 7-4′-epoxy-8′-8′′/7′-2′′ scaffold, consisting of an aryltetrahydronaphthalene and a dihydrobenzofuran moiety. The planar structures of compounds 2, 3, 7, and 8 were documented previously; however, their absolute configurations were established for the first time in this study. The antioxidant activities of 1a/1b–8a/8b were evaluated using DPPH free radical scavenging assay, and the results demonstrated that compounds 1b and 3b showed potent DPPH radical scavenging activities with IC50 values of 5.987 ± 1.212 and 9.641 ± 0.865 μg/mL, respectively.

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Section: Resultssupporting

confidence: 71%

Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Lai

Zhou

et al. 2016

Sci Rep

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“…Recently, research regarding the chemical constituents of some medicinal and edible plants, including the fruits of Rubus idaeus and Crataegus pinnatifida and the seed of Cerasus pseudocerasus , led to the isolation of a series of 1-oxygenated 1,2-diarylpropan-3-ols ( 1 – 18 ) (Figure ), including seven pairs of diastereomers ( 1 / 2 , 3 / 4 , 6 / 7 , 8 / 9 , 11 / 12 , 14 / 15 , and 17 / 18 ). − ,,, Their two-dimensional (2D) structures were elucidated through spectroscopic data analyses (UV, one-dimensional (1D) and 2D NMR, and high-resolution electrospray ionization mass spectrometry (HRESIMS)). Initially, the 1 H NMR spectra of 1,2-diarylpropan-1-alkoxy-3-ols were measured in CDCl 3 , because they were isolated from the low polarity fractions.…”

Section: Resultsmentioning

confidence: 99%

“…). − Of these compounds, the 1,2-diarylpropan-3-ol type is an important group belonging to the β-1 linkage group, with diverse pharmacological properties. Over the past decades, more and more 1,2-diarylpropan-3-ols have been found in roots, rhizomes, stems, bark, leaves, seeds, and fruits of plants. − The syntheses of these compounds, especially chiral ones (Figure ), have attracted attention from researchers in the area of organic synthesis. − …”

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confidence: 99%

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by ¹H NMR Spectroscopy

et al. 2021

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The structural elucidation of chiral molecules with more than one stereocenter is usually a tricky problem. In this paper, efficient 1H NMR spectroscopic approaches for assigning the erythro and threo configurations of 1-oxygenated 1,2-diarylpropan-3-ols were developed. By analysis of the chemical shift differences of diastereotopic methylene H2-3 (Δδ3) in CDCl3 or the chemical shift differences of H-1 and H-2 (Δδ1,2) in methanol-d 4, deuterated dimethyl sulfoxide, and acetone-d 6, the configurations of 1-oxygenated 1,2-diarylpropan-3-ols can be rapidly and conveniently determined.

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“…being determined via the TDDFT-ECD method [75]. Compounds 121 and 122 were first reported as racemic mixtures from Casearia grewiifolia in 2012 [76] and were resolved into two pairs of enantiomers by Qiu et al in 2018, with the rel. and abs.…”

Section: Simple Phenylpropanoidsmentioning

confidence: 99%

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

Capon

et al. 2022

Molecules

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The knowledge that natural products (NPs) are potent and selective modulators of important biomacromolecules (e.g., DNA and proteins) has inspired some of the world’s most successful pharmaceuticals and agrochemicals. Notwithstanding these successes and despite a growing number of reports on naturally occurring pairs of enantiomers, this area of NP science still remains largely unexplored, consistent with the adage “If you don’t seek, you don’t find”. Statistically, a rapidly growing number of enantiomeric NPs have been reported in the last several years. The current review provides a comprehensive overview of recent records on natural enantiomers, with the aim of advancing awareness and providing a better understanding of the chemical diversity and biogenetic context, as well as the biological properties and therapeutic (drug discovery) potential, of enantiomeric NPs.

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New phenolics from the wood of Casearia grewiifolia

Cited by 18 publications

References 23 publications

Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by ¹H NMR Spectroscopy

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

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New phenolics from the wood of Casearia grewiifolia

Cited by 18 publications

References 23 publications

Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by 1H NMR Spectroscopy

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

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Product

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About

Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by ¹H NMR Spectroscopy