Preparative isolation and structural characterization of sucrose ester isomers from oriental tobacco

Jia, Chuanbao; Wang, Yingying; Zhu, Yonghua; Xu, Chunping; Mao, Duobin

doi:10.1016/j.carres.2013.01.021

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…Under basic conditions, hydrolysis occurred exclusively at the ester bonds; however, under acidic conditions, the glycosidic bond preferentially breaks. Thus, to identify a sugar moiety, SE hydrolysis is usually carried out with KOH , or NaOH. , However, in recent studies on members of the genus Physalis , a NaOH solution was used to facilitate sucrose recovery, and high purity levels were achieved. ,, …”

Section: Resultsmentioning

confidence: 99%

Upregulation of Skin-Aging Biomarkers in Aged NHDF Cells by a Sucrose Ester Extract from the Agroindustrial Waste of Physalis peruviana Calyces

Cicchetti¹,

Duroure²,

Borgne³

et al. 2018

J. Nat. Prod.

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As part of a search for new sustainable plant sources of valuable compounds, the EtOAc extract of the discarded calyces of Physalis peruviana fruit was selected for its significant antiaging activity. Eight new sucrose esters (SEs), named peruvioses F-M (1-8), along with three known SEs, peruvioses A (9), peruviose B (10), and nicandrose D (11), were isolated. Their structures were elucidated by comprehensive analyses of their NMR and MS data. A global fragmentation pattern of these SEs was established from their MS data. The SE extract (SEE) at a concentration of 0.5 mg L upregulated multiple skin-aging biomarkers, namely, collagen I, elastin, and fibrillin-1, in aged normal human dermal fibroblast cells. A 36% increase in collagen I was observed. The elastin and fibrillin-1 contents were fully recovered, and an increase of at least 10% in the production of elastin was observed.

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Section: Resultsmentioning

confidence: 99%

Upregulation of Skin-Aging Biomarkers in Aged NHDF Cells by a Sucrose Ester Extract from the Agroindustrial Waste of Physalis peruviana Calyces

Cicchetti¹,

Duroure²,

Borgne³

et al. 2018

J. Nat. Prod.

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“…The SE-enriched fraction was obtained by a similar experimental procedure to that reported previously with some modifications [22]. Specifically, 100 g of tobacco powder was ultrasonically extracted twice in 1000 mL of EtOH at 30 The solution obtained above was subjected to column chromatography using a 24 mm (i.d.)…”

Section: Extraction and Separation Of Ses From Tobacco Leavesmentioning

confidence: 99%

“…To date, there are only a few studies that have reported complete characterization for certain SEs in tobacco. Jia [22] endeavored to characterize two groups of SE isomer mixtures from oriental tobacco with different molecular weights 664 (SE-664) and 650 (SE-650), respectively. High-resolution MS (HRMS) and NMR ( 1 H, 13 C, and heteronuclear single quantum correlation [HSQC]) provided evidence about the basic structure framework and types of aliphatic acids for these SEs.…”

Section: Introductionmentioning

confidence: 99%

Separation, identification, and structural characterization of sucrose ester isomers from tobacco

Zhu,

Yuan,

Xie

et al. 2023

J of Separation Science

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Sucrose esters (SEs) are crucial tobacco smoke flavor precursors and play a significant role in tobacco's functionality. Due to their structural complexity, the separation and analysis of SEs in tobacco remain a major challenge, and massive structures of SEs have not yet been fully identified. In this study, the fractions enriched in SEs were obtained from oriental and flue‐cured tobacco through a series of pretreatments, and two types of SEs (Types I and II) were distinguished by liquid chromatography‐tandem mass spectrometry (LC‐MSn) analysis, with Type II SEs newly characterized in tobacco. Five groups of main SEs were further purified using preparative high‐performance LC (HPLC) coupled to an evaporative light scattering detector, and their structures were characterized by nuclear magnetic resonance spectrometry techniques including 1H, 13C, correlation spectroscopy, heteronuclear single quantum correlation, and heteronuclear multiple bond correlation. By combining LC‐MSn and nuclear magnetic resonance spectrometry, the structures of eight SE isomers were finally proposed, of which four were newly identified. These findings further enhance the understanding of the structural diversity of SEs in tobacco, serving as a valuable reference for future research on the elucidation, synthesis, and metabolism of SEs.

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Patterns of inheritance of acylsugar acyl groups in selected interspecific hybrids of genus Nicotiana

et al. 2020

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Preparative isolation and structural characterization of sucrose ester isomers from oriental tobacco

Cited by 9 publications

References 21 publications

Upregulation of Skin-Aging Biomarkers in Aged NHDF Cells by a Sucrose Ester Extract from the Agroindustrial Waste of Physalis peruviana Calyces

Upregulation of Skin-Aging Biomarkers in Aged NHDF Cells by a Sucrose Ester Extract from the Agroindustrial Waste of Physalis peruviana Calyces

Separation, identification, and structural characterization of sucrose ester isomers from tobacco

Patterns of inheritance of acylsugar acyl groups in selected interspecific hybrids of genus Nicotiana

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