Stability of Sucrose Fatty Acid Esters under Acidic and Basic Conditions

Okumura, Haruo; Kitazawa, Naoki; Wada, Shoichi; Hotta, Hiroshi

doi:10.5650/jos.60.313

Cited by 14 publications

(9 citation statements)

References 17 publications

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“…The absolute configurations of the sugar moieties were determined by alkaline hydrolysis. Indeed, SEs tend to degrade differently under basic and acidic hydrolysis conditions . Under basic conditions, hydrolysis occurred exclusively at the ester bonds; however, under acidic conditions, the glycosidic bond preferentially breaks.…”

Section: Resultsmentioning

confidence: 99%

“…Indeed, SEs tend to degrade differently under basic and acidic hydrolysis conditions. 45 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 46,47 or NaOH.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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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%

Section: ■ Results and Discussionmentioning

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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“…Animal studies indicate that sucrose fatty acid esters are hydrolyzed by intestinal enzymes into sucrose and fatty acids and that their metabolites are not toxic . In addition, sucrose esters are chemically hydrolyzed under acidic or basic conditions and can be disintegrated by bacterial lipases . Tween 80 and Cremophor RH40 are also degraded in the intestine or in the blood, but the effects of the metabolites are unknown.…”

Section: Discussionmentioning

confidence: 99%

Sucrose Esters Increase Drug Penetration, But Do Not Inhibit P‐Glycoprotein in Caco‐2 Intestinal Epithelial Cells

Kiss

Hellinger

Pilbat

et al. 2014

Journal of Pharmaceutical Sciences

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“…Specific acyl sucrose regioisomers have been shown to have different physicochemical properties, including significantly varying critical micelle concentrations (CMCs) and different stability under acidic and basic conditions at elevated temperatures. [6,7] The regioisomers of sucrose laurate and sucrose caprate have previously been separated using analytical reversed-phase high-performance liquid chromatography (RP-HPLC), [8] and the structure of acyl sucrose regioisomers has been identified by nuclear magnetic resonance (NMR) spectroscopy and proven to exhibit little variation in chemical shifts depending on the size of the fatty acid (see Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Structural Analyses of Sucrose Laurate Regioisomers by Mass Spectrometry Techniques

Lie

Stensballe

Pedersen

2015

Journal of Carbohydrate Chemistry

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6-And 6 -O-lauroyl sucrose were isolated and analyzed by matrix-assisted laser desorption/ionisation (MALDI) time-of-flight (TOF) mass spectrometry (MS), Orbitrap high-resolution (HR) MS, and electrospray-ionization (ESI) tandem mass spectrometry (MS/MS). The analyses aimed to explore the physicochemical differences between the regioisomers and how the position of the fatty acid ester substitution affects the molecular and conformational stability. MALDI-TOF MS resulted in signals characteristic for the molecular ion adducts with sodium and potassium, [M + Na] + and [M + K] + , m/z 547.9 and 563.8, respectively, and Orbitrap HRMS confirmed the mass of [M + Na] + (m/z 547.2712). ESI-MS/MS on the precursor ion [M + Na] + resulted in product ion mass spectra showing two high-intensity signals for each sample. 6-O-Lauroyl sucrose produced signals located at m/z 547.27 and m/z 385.21, corresponding to the 6-O-lauroyl glucose sodium adduct ions, while the signals for 6 -O-lauroyl sucrose were located at m/z 385.22 and 367.20, respectively corresponding to the sodium adduct ions with 6-O-lauroyl fructose and 6-O-lauroyl fructosyl. The mass spectra of the two regioisomers were clearly different, and the investigation revealed the importance of the position of the fatty acid ester for the conformational stability and resulting fragmentation pathways of sucrose laurate regioisomers. The results of the employed MS techniques indicated the higher stability of the glycosidic linkage in 6-O-lauroyl sucrose, compared to the 6 -O-regioisomer.

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Stability of Sucrose Fatty Acid Esters under Acidic and Basic Conditions

Cited by 14 publications

References 17 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

Sucrose Esters Increase Drug Penetration, But Do Not Inhibit P‐Glycoprotein in Caco‐2 Intestinal Epithelial Cells

Structural Analyses of Sucrose Laurate Regioisomers by Mass Spectrometry Techniques

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