Enantiomeric chromones from Harrisonia perforata

Guo, Linghong; Zheng, Rong; Liu, Zhi Wen; Wang, Wen Jing; Li, Guo Qiang; Fan, Chun Lin; Ye, Wen Cai; Tao, Chun

doi:10.1016/j.phytol.2014.10.014

Cited by 9 publications

(18 citation statements)

References 16 publications

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“…2). The closest analogs are (2'S)perforatin C (6) and its enantiomer (2'R)-perforatin C (7), which have been reported from Harrisonia perforata (Rutaceae) [12] (Fig. 3).…”

Section: Resultsmentioning

confidence: 85%

Prenylated chromones and coumarins from the leaves of Billburttia capensoides Sales & Hedge (Apiaceae)

Andrianjakaniaina¹,

Rakotondramanana²,

Benatrehina³

et al. 2021

GSC Biol. and Pharm. Sci.

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Billburttia Sales & Hedge is a new genus endemic to Madagascar, which belongs to the Apiaceae family and comprises of two species, namely Billburttia capensoides and B. vaginoides. The present work was undertaken in a view to explore secondary metabolites from the leaves of B. capensoides, contributing to have more knowledge on the chemical profile of this species. Liquid-liquid partition followed by chromatographic separation of its ethanolic extract led to the isolation of two new prenylated chromones, 2'R-hydroxy-7-O-methylallopeucenin and the known coumarins imperatorin and xanthotoxin. Their chemical structures were established on the basis of spectroscopic methods including nuclear magnetic resonance (NMR) and high resolution mass spectrometry, and by comparison with the reported data in the literature. The structure of the compound 3 was confirmed by single-crystal X-ray diffraction. This is the first report on the nonvolatile constituents of B. capensoides. The presence of imperatorin and xanthotoxin supported that the new endemic genus Billburttia belongs to the Apiaceae family. All these data may induce further research on this species in order to find new chemical entities with biological and chemotaxonomic interests.

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“…2). The closest analogs are (2'S)perforatin C (6) and its enantiomer (2'R)-perforatin C (7), which have been reported from Harrisonia perforata (Rutaceae) [12] (Fig. 3).…”

Section: Resultsmentioning

confidence: 85%

Prenylated chromones and coumarins from the leaves of Billburttia capensoides Sales & Hedge (Apiaceae)

Andrianjakaniaina¹,

Rakotondramanana²,

Benatrehina³

et al. 2021

GSC Biol. and Pharm. Sci.

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“…configs. of 417a/417b were assigned by Mosher's method [198]. From the same plant, 422a/422b were reported as a pair of enantiomeric molecules by Yuan et al in 2017 [199].…”

Section: Chromanesmentioning

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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“…This was dispersed in water (4.0 L) and extracted with light petroleum and ethyl acetate in turn. The light petroleum and ethyl acetate portions (1 kg) were combined and then passed over a silica gel column, eluting with a gradient of light petroleum-acetone (from 1:0 to 0:1), to yield 5 major fractions (1)(2)(3)(4)(5). Subsequently, Fr.3 (200 g) was separated over an MCI column (MeOH-H 2 O from 3:7 to 10:0) to obtain 4 sub-fractions (3A-3D).…”

Section: Isolation and Purificationmentioning

confidence: 99%

“…is the only species growing in China [1], and has been used as a folk medicine against malaria and boils [2]. Several chromones [3][4][5][6], limonoids [4,[7][8][9][10][11], quassinoids [12,13], and polyketides [14] have been isolated from H. perforata. As part of our effort to search for biologically active constituents of this species [7,12,15], a new pair of chromone enantiomers, perforisone A, along with four known compounds, peucenin-7methyl ether (2) [16], umtatin (3) [17], greveichromenol (4) [17], and saikochromone A (5) [18], were isolated from the leaves and stems of the title plant.…”

mentioning

confidence: 99%

(±)-Perforison A, A Pair of New Chromone Enantiomers from Harrisonia perforata

Yuan

Gao

Zhang

et al. 2017

Natural Product Communications

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Dedicated to Prof. Lisheng Ding on the occasion of his 60th birthday. (+)-Perforison A and (−)-perforison A, a new pair of chromone enantiomers, along with four known compounds, were isolated from the leaves and stems of Harrisonia perforata. Their structures and absolute configurations were determined on the basis of extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. The cytotoxic activities in vitro of these compounds were evaluated, but none showed significant activity.

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Enantiomeric chromones from Harrisonia perforata

Cited by 9 publications

References 16 publications

Prenylated chromones and coumarins from the leaves of Billburttia capensoides Sales & Hedge (Apiaceae)

Prenylated chromones and coumarins from the leaves of Billburttia capensoides Sales & Hedge (Apiaceae)

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

(±)-Perforison A, A Pair of New Chromone Enantiomers from Harrisonia perforata

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