The extracts from the bark of Prunus avium and Prunus cerasus have been analyzed by using high pressure liquid chromatography/electrospray ionization mass spectrometry. For the first time in the bark of Prunus species flavonoid C-glycosides have been detected. On the basis of the characteristic fragmentation patterns of their [M-H]− and [M + H]+ ions, three flavonoid C-glycosides have been identified, namely apigenin-6,8-di-C-glucoside (vicenin-2), apigenin-6-C-glucoside (isovitexin) and chrysin-8-C-glucoside. Taking into account the widely studied biological activities of flavonoid C-glycosides, the barks of these common fruit trees seem to be interesting materials of potential medical or cosmetic application.
TalhiOSilvaAMS.Advances in C-glycosyl flavonoid research. Curr Org Chem2012;
16: 859–896.
2.
RusinAChrubasikMPapajK, et al.
C-glycosidic genistein conjugates and their antiproliferative activity. J Chem2013;
2013: 1–14.
3.
XiaoJCapanogluEJassbiAR, et al.
Advance on the flavonoid C-glycosides and health benefits. Crit Rev Food Sci Nutr2016;
56: S29–S45.
4.
XiaoJMuzashviliTSGeorgievMI.Advances in the biotechnological glycosylation of valuable flavonoids. Biotechnol Adv2014;
32: 1145–1156.
5.
SzejaWGrynkiewiczGRusinA.Isoflavones, their glycosides and glycoconjugates. Synthesis and biological activity. Curr Org Chem2017;
21: 218–235.
6.
WenaLZhaoYJiangY, et al.
Identification of a flavonoid C-glycoside as potent antioxidant. Free Radic Biol Med2017;
110: 92–101.
7.
HeMMinJ-WKongW-L, et al.
A review on the pharmacological effects of vitexin and isovitexin. Fitoterapia2016;
115: 74–85.
8.
GanesanKXuB.Molecular targets of vitexin and isovitexin in cancer therapy: a critical review. Ann N Y Acad Sci2017;
1401: 102–113.
9.
CaoXLiuLYuanQ, et al.
Isovitexin reduces carcinogenicity and stemness in hepatic carcinoma stem-like cells by modulating MnSOD and FoxM1. J Exp Clin Cancer Res2019;
38: 264.
10.
LiangXXuCCaoX, et al.
Isovitexin suppresses cancer stemness property and induces apoptosis of osteosarcoma cells by disruption of the DNMT1/miR-34a/bcl-2 axis. Cancer Manag Res2019;
11: 8923–8936.
11.
LeeI-CBaeJ-S.Hepatoprotective effects of vicenin-2 and scolymoside through the modulation of inflammatory pathways. J Nat Med2020;
74: 90–97.
12.
SinghalSSJainDSinghalP, et al.
Targeting the mercapturic acid pathway and vicenin-2 for prevention of prostate cancer. Biochim Biophys Acta Rev Cancer2017;
1868: 167–175.
13.
BaruahTJKmaL.Vicenin-2 acts as a radiosensitizer of the non-small cell lung cancer by lowering Akt expression. BioFactors2019;
45: 200–210.
14.
YinYYeLNiuZ, et al.
Anti-inflammatory effects of vicenin-2 on dextran sulfatesodium-induced colitis in mice. Drug Dev Res2019;
80: 546–555.
15.
OyetayoAMBadaSO.Phytochemical screening and antibacterial activity of Prunus avium extracts against selected human pathogens. JOCAMR2017;
4: 1–8.
16.
AroraDSMahajanH.In vitro evaluation and statistical optimization of antimicrobial activity of Prunus cerasoides stem bark. Appl Biochem Biotechnol2018;
184: 821–837.
17.
KangHKwakT-KKimB-G, et al.
The anti-inflammatory effect of Prunus yedoensis bark extract on adipose tissue in diet-induced obese mice.Evid Based Complement Alternat Med2015;
2015: 937904.
18.
YamaguchiKLiggettJLKimN-C, et al.
Anti-proliferative effect of horehound leaf and wild cherry bark extracts on human colorectal cancer cells. Oncol Rep2006;
15: 275–281.
19.
KomakechRKangYLeeJ-H, et al.
A review of the potential of phytochemicals from Prunus africana (hook f.) Kalkman stem bark for chemoprevention and chemotherapy of prostate cancer. Evid-Based complementAlternat Med2017;
2017: 3014019.
20.
HwangDKimHShinH, et al.
Cosmetic effects of Prunus padus bark extract. Korean J Chem Eng2014;
31: 2280–2285.
21.
HubertJAngelisAAligiannisN, et al.
In vitro dermo-cosmetic evaluation of bark extracts from common temperate trees. Planta Med2016;
82: 1351–1358.
22.
PoonamVRaunak KumarG, et al.
Chemical constituents of the genus Prunus and their medicinal properties. Curr Med Chem2011;
18: 3758–3824.
23.
Luna-VázquezFJIbarra-AlvaradoCRojas-MolinaA, et al. Prunus. In: YahiaEM (ed.) Fruit and vegetable phytochemicals: chemistry and human health. 2nd ed.
New Jersey:
John Wiley & Sons, Inc., pp.1215–1226.
24.
SmailagićAVeljovićSGašićU, et al.
Phenolic profile, chromatic parameters and fluorescence of different woods used in Balkan cooperage. Ind Crops Prod2019;
132: 156–167.
25.
StobieckiMStaszkówAPiaseckaA, et al.
LC-MSMS profiling of flavonoid conjugates in wild Mexican lupine, Lupinus reflexus. J Nat Prod2010;
73: 1254–1260.
26.
HooperAMCaulfieldJCHaoB, et al.
Isolation and identification of desmodium root exudates from drought tolerant species used as intercrops against Striga hermonthica. Phytochemistry2015;
117: 380–387.
27.
GattusoGCaristiCGargiuliC, et al.
Flavonoid glycosides in bergamot juice (Citrus bergamia risso). J Agric Food Chem2006;
54: 3929–3935.
28.
BarrecaDBelloccoECaristiC, et al.
Flavonoid composition and antioxidant activity of juices from chinotto (citrus × myrtifolia raf.) fruits at different ripening stages. J Agric Food Chem2010;
58: 3031–3036.
29.
FerreresFGil-IzquierdoAVinholesJ, et al.
Approach to the study of C-glycosyl flavones acylated with aliphatic and aromatic acids from Spergularia rubra by high-performance liquid chromatography-photodiode array detection/electrospray ionization multi-stage mass spectrometry. Rapid Commun Mass Spectrom2011;
25: 700–712.
30.
CaoJYinCQinY, et al.
Approach to the study of flavone di-C-glycosides by high performance liquid chromatography tandem ion trap mass spectrometry and its application to characterization of flavonoid composition in Viola yedoensis. J Mass Spectrom2014;
49: 1010–1024.
31.
SchulzeAEDe BeerDVilliersA, et al.
Chemometric analysis of chromatographic fingerprints shows potential of Cyclopia maculata (Andrews) kies for production of standardized extracts with high xanthone content. J Agric Food Chem2014;
62: 10542–10551.
32.
FriščićMBucarFPilepićKH.LC-PDA-ESI-MSn analysis of phenolic and iridoid compounds from Globularia spp. J Mass Spectrom2016;
51: 1211–1236.
33.
GouveaDRBuquiGALopesJLC, et al.
An UPLC-MS/MS method for determination of vicenin-2 and lychnopholic acid in rat plasma and its application to a pharmacokinetic study. J Braz Chem Soc2017;
28: 427–434.
34.
PatelNKSharath KumarLMGajeraJ, et al.
Isolation and characterization of flavonoid C-glycosides from Prosopis glandulosa torr. leaves. Phcog Mag2018;
14: 451–454.
35.
LuoYRenZDuB, et al.
Structure identification of vicenin II extracted from Dendrobium officinale and the reversal of TGF-β1-induced epithelial-mesenchymal transition in lung adenocarcinoma cells through TGF-β/Smad and PI3K/Akt/mTOR signaling pathways. Molecules2019;
24: 144.
36.
SallesBCCDa SilvaMATaniguthiL, et al.
Passiflora edulis leaf extract: evidence of antidiabetic and antiplatelet effects in rats. Biol Pharm Bull2020;
43: 169–174.
37.
BernardoJFerreresFGil-IzquierdoA, et al.
Medicinal species as MTDLs: Turnera diffusa willd. Ex Schult inhibits CNS-enzymes and delays glutamate excitotoxicity in SH-SY5Y cells via oxidative damage. Food Chem Toxicol2017;
106: 466–476.
38.
Llorent-MartínezEJZenginGLobineD, et al.
Phytochemical characterization, in vitro and in silico approaches for three Hypericum species. New J Chem2018;
42: 5204–5214.
39.
RavisankaraSAliKAAwikaJM.Structural profile of soluble and bound phenolic compounds in TEFF (Eragrostis tef) reveals abundance of distinctly different flavones in white and brown varieties. Food Chem2018;
263: 265–274.
40.
Abad-GarcíaBGarmón-LobatoSBerruetaLA, et al.
New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadrupole mass spectrometry. Rapid Commun Mass Spectrom2008;
22: 1834–1842.
41.
WolffTBerruetaLAValenteLMM, et al.
Comprehensive characterisation of polyphenols in leaves and stems of three anti-dengue virus type-2 active brazilian Faramea species (rubiaceae) by HPLC-DAD-ESI-MS/MS. Phytochem Anal2019;
30: 62–72.
42.
LiHSongFXingJ, et al.
Screening and structural characterization of α-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MSn and SORI-CID FTICR MS. J Am Soc Mass Spectrom2009;
20: 1496–1503.
43.
GengPSunJZhangM, et al.
Comprehensive characterization of C-glycosyl flavones in wheat (Triticum aestivum L.) germ using UPLC-PDA-ESI/HRMSn and mass defect filtering. J Mass Spectrom2016;
51: 914–930.
44.
HaoBCaulfieldJCHamiltonML.Biosynthesis of natural and novel C-glycosyl flavones utilizing recombinant Oryza sativa C-glycosyltransferase (OsCGT) and desmodium incanum root proteins. Phytochemistry2016;
125: 73–87.
45.
LapčíkO.Isoflavonoids in non-leguminous taxa: a rarity or a rule?Phytochemistry2007;
68: 2909–2916.
46.
ChengGBaiYZhaoY, et al.
Flavonoids from Ziziphus jujuba mill var. Spinosa. Tetrahedron2000;
56: 8915–8920.
47.
BórquezJKennellyEJSimirgiotisMJ.Activity guided isolation of isoflavones and hyphenated HPLC-PDA-ESI-ToF-MS metabolome profiling of Azorella madreporica clos. from Northern Chile. Food Res Int2013;
52: 288–297.
48.
PrawatsriSSuksamrarnAChindaduangA, et al.
Abietane diterpenes from Hyptis suaveolens. Chem Biodivers2013;
10: 1494–1500.
49.
ZhuJYiXZhangJ, et al.
Chemical profiling and antioxidant evaluation of yangxinshi tablet by HPLC-ESI-Q-TOF-MS/MS combined with DPPH assay. J Chromatogr B Analyt Technol Biomed Life Sci2017;
1060: 262–271.
50.
GeibelMTreuttertDMeierN.Characterization of sour cherries by HPLC-analysis of the bark-flavonoids combined with multivariate statistics. Euphytica1990;
45: 229–235.
51.
GeibelMGeigerHTreutterD.Tectochrysin 5- and genistein 5-glucosides from the bark of Prunus cerasus. Phytochemistry1990;
29: 1351–1353.
52.
GeibelMFeuchtW.Flavonoid 5-glucosids from prunus cerasus bark and their characteristic weak glycosidic bonding. Phytochemistry1991;
30: 1519–1521.
53.
MimakiYSashidaYAdachuT, et al.
Chemical study on the genus Prunus (Rosaceae) comparative studies on the chemical constituent of the barks of the subgenera Cerasus padus and Laurocerasus plants. Nat Med1994;
48: 86–91.
54.
GüçlüFS.Identification of polyphenols in homogenetic and heterogenetic combination of cherry graftings. Pak J Bot2019;
51: 2067–2072.
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