Matrix solid-phase dispersion combined with micro-fractionation bioactivity evaluation screening polymethoxylated flavones from Citrus peels.
Citrus peel
antioxidant
matrix solid-phase dispersion
micro-fractionation bioactive evaluation
polymethoxyflavones
Journal
Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554
Informations de publication
Date de publication:
Nov 2023
Nov 2023
Historique:
revised:
08
09
2023
received:
05
08
2023
accepted:
17
09
2023
medline:
27
11
2023
pubmed:
28
9
2023
entrez:
28
9
2023
Statut:
ppublish
Résumé
Polymethoxyflavones were a unique class of natural and safe flavonoids containing two or more methoxy groups, which were also the most abundant edible part in Citrus peel. The optimum condition in the process of selective extraction of polymethoxylated flavones from Citrus peel by matrix solid-phase dispersion (MSPD) was as follows: SBA-15 as adsorbent, ethyl acetate as eluent, the mass ratio of adsorbent to sample 1:1, and the mixture of sample and adsorbent was ground for 3 min. Twelve antioxidants were successfully screened by micro-fractionation bioactivity evaluation assay, in which four of them were flavonoid glycosides, seven of them were polymethoxylated flavones, and one was phenylpropanoid. 1-sinapoly-β-D-glucopyranoside (1) was reported for the first time in Citrus peel. And antioxidant capacity of 1-sinapoly-β-D-glucopyranoside, 5, 7, 8, 3', 4', 5'-hexamethoxyflavone (6), hexamethoxyflavone (11), and 5, 6, 7, 4'-tetramethoxyflavone (7) were reported for the first time. Nobiletin (compound 8), 3, 5, 6, 7, 8, 3', 4'-heptamethoxyflavone (9) and tangeretin (10) were isolated and purified by countercurrent chromatography combined with preparative liquid chromatography. Antioxidant activity evaluation indicated that the three isolated polymethoxylated flavones owned similar antioxidant activity. This study indicated that MSPD combined with micro-fractionation bioactive evaluation was efficient in screening bioactive compounds for rapid extraction and effective pinpointing bioactive substances in natural products.
Identifiants
pubmed: 37759397
doi: 10.1002/jssc.202300570
doi:
Substances chimiques
Antioxidants
0
Flavones
0
Flavonoids
0
Plant Extracts
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300570Subventions
Organisme : National Natural Science Foundation of China
ID : 21978266
Organisme : Natural Science Foundation of Zhejiang Province
ID : LBY22H280004
Organisme : Taizhou Science and Technology Plan Project
ID : 21nya10
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
Zhang H, Cui J, Tian G, DiMarco-Crook C, Gao W, Zhao C, et al. Efficiency of four different dietary preparation methods in extracting functional compounds from dried tangerine peel. Food Chem. 2019;289:340-350.
Li S, Pan MH, Lo C-Y, Tan D, Wang Y, Shahidi F, et al. Chemistry and health effects of polymethoxyflavones and hydroxylated polymethoxyflavones. J Funct Foods. 2009;1:2-12.
Tu B, Chen Z, Liu Z, Li R, Hu YJJRA. Study of the structure-activity relationship of flavonoids based on their interaction with human serum albumin. RSC Adv. 2015;5:73290-73300.
Chen J, Wang Y, Zhu T, Yang S, Cao J, Li X, et al. Beneficial Regulatory effects of polymethoxyflavone-rich fraction from Ougan (Citrus reticulata cv. Suavissima) Fruit on gut microbiota and identification of its intestinal metabolites in mice. Antioxidants 2020;9:831-840.
Ahmad B, Friar EP, Vohra MS, Khan N, Serpell CJ, Garrett MD, et al. Hydroxylated polymethoxyflavones reduce the activity of pancreatic lipase, inhibit adipogenesis and enhance lipolysis in 3T3-L1 mouse embryonic fibroblast cells. Chem Biol Interact. 2023;379:110503. https://doi.org/10.1016/j.cbi.2023.110503
Wang Y, Jin R, Chen J, Cao J, Xiao J, Li X, et al. Tangeretin maintains antioxidant activity by reducing CUL3 mediated NRF2 ubiquitination. Food Chem. 2021;365:130470-130480.
Tung Y-C, Chou Y-C, Hung W-L, Cheng A-C, Yu R-C, Ho C-T, et al. Polymethoxyflavones: Chemistry and Molecular Mechanisms for Cancer Prevention and Treatment. Curr Pharmacol Rep. 2019;5:98-113.
Wang M, Meng D, Zhang P, Wang X, Du G, Brennan C, et al. Antioxidant protection of nobiletin, 5-demethylnobiletin, tangeretin, and 5-demethyltangeretin from Citrus Peel in Saccharomyces cerevisiae. J Agric Food Chem. 2018;66:3155-3160.
Gana R, Liua Y, Li H, Xia Y, Guo H, Geng F, et al. Natural sources, refined extraction, biosynthesis, metabolism, and bioactivities of dietary polymethoxyflavones (PMFs). Food Sci Huma Well. 2024;13:27-49.
Wang Y, Jin R, Chen J, Cao J, Xiao J, Li X, et al. Tangeretin maintains antioxidant activity by reducing CUL3 mediated NRF2 ubiquitination. Food Chem. 2021;365:130470.
Barker S, Long AR, Short AR. Isolation of drug residues from tissues by solid phase dispersion. J Chromatogr A. 1989;475:353-361.
Wianowska D, Gil MJ. New insights into the application of MSPD in various fields of analytical chemistry. TrAC Trend Anal Chem. 2019;112:29-51.
Kool J, Giera M, Irth H, Niessen WM. Advances in mass spectrometry-based post-column bio-affinity profiling of mixtures. Anal Bioanal Chem. 2011;399:2655-2668.
Tao JM, Rappe AM. Physical adsorption: theory of van der Waals interactions between particles and clean surfaces. Phys Rev Lett. 2016;112:106101-106106.
Mansur A, Kim K, Kim D, Yoo M, Jang H, Kim D, et al. Matrix solid-phase dispersion extraction method for HPLC determination of flavonoids from buckwheat sprouts. LWT Food Sci Technol. 2020;133:1-10.
Cao W, Hu SS, Ye LH, Cao J, Pang XQ, Xu JJ. Trace matrix solid phase dispersion using a molecular sieve as the sorbent for the determination of flavonoids in fruit peels by ultra-performance liquid chromatography. Food Chem. 2016;190:474-480.
Fang L, Lin T, Chen B, You H, Wu C, Chu C, et al. High-performance liquid chromatography micro-fraction bioactive evaluation combined with countercurrent chromatographic separation of antioxidants from Citrus peel and their tyrosinase inhibition activities. J Sep Sci. 2023;46:2200764. https://doi.org/10.1002/jssc.202200764
Xu TT. Study on chemical compositions and metabonomics of the peels of mandarins and oranges by UPLC-QTOF-MS. Savannah, GA: West South University; 2018.
Singhal SS, Singhal S, Singhal P, Singhal J, Horne D, Awasthi S. Didymin: an orally active citrus flavonoid for targeting neuroblastoma. OncoTargets Ther. 2017;8:29428-29441.
Liu J. Study on efficient separation of polymethoxylated flavones from Citri Reticulatae Pericarpium and their potential inhibitory activity against Sars-Cov-2 3CLpro. Mod Tradit Chin Med Materia World Sci Technol. 2021:23:4622-4631.
Han S, Kim H, Lee J, Mok S, Lee SJJAFC. Isolation and Identification of Polymethoxyflavones from the Hybrid Citrus. Hallabong 2010;58:9488-9491.
Xu Y, Lv X, Yang G, Zhan J, Li M, Long T, et al. Simultaneous separation of six pure polymethoxyflavones from sweet orange peel extract by high performance counter current chromatography. Food Chem. 2019;292:160-165.