A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare

Polyphenols are known dietary antioxidants. They have recently attracted considerable interest in uses to prevent skin aging and hyperpigmentation resulting from solar UV-irradiation. <i>Prunus persica</i> (L.) leaves are considered by-products and were reported to have a remarkable anti...

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Main Authors: Eman S. Mostafa, Ahmed Maher, Dalia A. Mostafa, Sameh S. Gad, Mahmoud A.M. Nawwar, Noha Swilam
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Antioxidants
Subjects:
Online Access:https://www.mdpi.com/2076-3921/10/3/436
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spelling doaj-eabb747f647f4fc4a136241f7f8d3ad42021-03-13T00:04:26ZengMDPI AGAntioxidants2076-39212021-03-011043643610.3390/antiox10030436A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for SkincareEman S. Mostafa0Ahmed Maher1Dalia A. Mostafa2Sameh S. Gad3Mahmoud A.M. Nawwar4Noha Swilam5Department of Pharmacognosy, Faculty of Pharmacy, October University of Modern Sciences and Arts (MSA), Giza 12451, EgyptDepartment of Biochemistry, Faculty of Pharmacy, October University for Modern Sciences and Arts (MSA), Giza 12451, EgyptDepartment of Pharmaceutics, Faculty of Pharmacy, October University of Modern Sciences and Arts (MSA), Giza 12451, EgyptDepartment of Pharmacology, Faculty of Pharmacy, October University for Modern Sciences and Arts (MSA), Giza 12451, EgyptNational Research Centre, Department of Phytochemistry, Dokki, Cairo 12622, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, The British University in Egypt (BUE), Cairo 11837, EgyptPolyphenols are known dietary antioxidants. They have recently attracted considerable interest in uses to prevent skin aging and hyperpigmentation resulting from solar UV-irradiation. <i>Prunus persica</i> (L.) leaves are considered by-products and were reported to have a remarkable antioxidant activity due to their high content of polyphenols. This study aimed at the development of a cosmeceutical anti-aging and skin whitening cream preparation using ethanol leaves extract of <i>Prunus persica</i> (L.) (PPEE) loaded in solid lipid nanoparticles (SLNs) to enhance the skin delivery. Chemical investigation of PPEE showed significantly high total phenolic and flavonoids content with notable antioxidant activities (DPPH, ABTS, and <i>β</i>-carotene assays). A unique acylated kaempferol glycoside with a rare structure, kaempferol 3<i>-O-β</i>-<i><sup>4</sup>C<sub>1</sub></i>-(6″-<i>O</i>-3,4-dihydroxyphenylacetyl glucopyranoside) (KDPAG) was isolated for the first time and its structure fully elucidated. It represents the first example of acylation with 3,4-dihydroxyphenyl acetic acid in flavonoid chemistry. The in-vitro cytotoxicity studies against a human keratinocytes cell line revealed the non-toxicity of PPEE and PPEE-SLNs. Moreover, PPEE, PPEE-SLNs, and KDPAG showed good anti-elastase activity, comparable to that of <i>N</i>-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone. Besides, PPEE-SLNs and KDPAG showed significantly (<i>p</i> < 0.001) higher anti-collagenase and anti-tyrosinase activities in comparison to EDTA and kojic acid, respectively. Different PPEE-SLNs cream formulae (2% and 5%) were evaluated for possible anti-wrinkle activity against UV-induced photoaging in a mouse model using a wrinkle scoring method and were shown to offer a highly significant protective effect against UV, as evidenced by tissue biomarkers (SOD) and histopathological studies. Thus, the current study demonstrates that <i>Prunus persica</i> leaf by-products provide an interesting, valuable resource for natural cosmetic ingredients. This provides related data for further studying the potential safe use of PPEE-SLNs in topical anti-aging cosmetic formulations with enhanced skin permeation properties.https://www.mdpi.com/2076-3921/10/3/436kaempferol 3<i>-O</i>-<i>β</i>-<i><sup>4</sup>C<sub>1</sub></i>-(6″-<i>O</i>-3,4-dihydroxyphenylacetyl glucopyranoside) by-productssolid lipid nanoparticlesantioxidantin-vitro skin related enzymesin-vivo anti-wrinkle
collection DOAJ
language English
format Article
sources DOAJ
author Eman S. Mostafa
Ahmed Maher
Dalia A. Mostafa
Sameh S. Gad
Mahmoud A.M. Nawwar
Noha Swilam
spellingShingle Eman S. Mostafa
Ahmed Maher
Dalia A. Mostafa
Sameh S. Gad
Mahmoud A.M. Nawwar
Noha Swilam
A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare
Antioxidants
kaempferol 3<i>-O</i>-<i>β</i>-<i><sup>4</sup>C<sub>1</sub></i>-(6″-<i>O</i>-3,4-dihydroxyphenylacetyl glucopyranoside) by-products
solid lipid nanoparticles
antioxidant
in-vitro skin related enzymes
in-vivo anti-wrinkle
author_facet Eman S. Mostafa
Ahmed Maher
Dalia A. Mostafa
Sameh S. Gad
Mahmoud A.M. Nawwar
Noha Swilam
author_sort Eman S. Mostafa
title A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare
title_short A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare
title_full A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare
title_fullStr A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare
title_full_unstemmed A Unique Acylated Flavonol Glycoside from <i>Prunus persica</i> (L.) var. Florida Prince: A New Solid Lipid Nanoparticle Cosmeceutical Formulation for Skincare
title_sort unique acylated flavonol glycoside from <i>prunus persica</i> (l.) var. florida prince: a new solid lipid nanoparticle cosmeceutical formulation for skincare
publisher MDPI AG
series Antioxidants
issn 2076-3921
publishDate 2021-03-01
description Polyphenols are known dietary antioxidants. They have recently attracted considerable interest in uses to prevent skin aging and hyperpigmentation resulting from solar UV-irradiation. <i>Prunus persica</i> (L.) leaves are considered by-products and were reported to have a remarkable antioxidant activity due to their high content of polyphenols. This study aimed at the development of a cosmeceutical anti-aging and skin whitening cream preparation using ethanol leaves extract of <i>Prunus persica</i> (L.) (PPEE) loaded in solid lipid nanoparticles (SLNs) to enhance the skin delivery. Chemical investigation of PPEE showed significantly high total phenolic and flavonoids content with notable antioxidant activities (DPPH, ABTS, and <i>β</i>-carotene assays). A unique acylated kaempferol glycoside with a rare structure, kaempferol 3<i>-O-β</i>-<i><sup>4</sup>C<sub>1</sub></i>-(6″-<i>O</i>-3,4-dihydroxyphenylacetyl glucopyranoside) (KDPAG) was isolated for the first time and its structure fully elucidated. It represents the first example of acylation with 3,4-dihydroxyphenyl acetic acid in flavonoid chemistry. The in-vitro cytotoxicity studies against a human keratinocytes cell line revealed the non-toxicity of PPEE and PPEE-SLNs. Moreover, PPEE, PPEE-SLNs, and KDPAG showed good anti-elastase activity, comparable to that of <i>N</i>-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone. Besides, PPEE-SLNs and KDPAG showed significantly (<i>p</i> < 0.001) higher anti-collagenase and anti-tyrosinase activities in comparison to EDTA and kojic acid, respectively. Different PPEE-SLNs cream formulae (2% and 5%) were evaluated for possible anti-wrinkle activity against UV-induced photoaging in a mouse model using a wrinkle scoring method and were shown to offer a highly significant protective effect against UV, as evidenced by tissue biomarkers (SOD) and histopathological studies. Thus, the current study demonstrates that <i>Prunus persica</i> leaf by-products provide an interesting, valuable resource for natural cosmetic ingredients. This provides related data for further studying the potential safe use of PPEE-SLNs in topical anti-aging cosmetic formulations with enhanced skin permeation properties.
topic kaempferol 3<i>-O</i>-<i>β</i>-<i><sup>4</sup>C<sub>1</sub></i>-(6″-<i>O</i>-3,4-dihydroxyphenylacetyl glucopyranoside) by-products
solid lipid nanoparticles
antioxidant
in-vitro skin related enzymes
in-vivo anti-wrinkle
url https://www.mdpi.com/2076-3921/10/3/436
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