Comparative Analysis of the Phenolic Profile of Lycium barbarum L. Fruits from Different Regions in China

Lycium barbarum L. (LB) fruits have high nutritive values and therapeutic effects. The aim of this study was to comprehensively evaluate the differences in phenolic composition of LB fruits from different geographical regions. Different methods of characterization and statistical analysis of data showed that different geographic sources of China could be significantly separated from each other. The highest total phenolic compound (TPC) content was observed in LB fruits from Ningxia (LBN), followed by those from Gansu (LBG) and Qinghai (LBQ). The Fourier transform infrared (FTIR) spectra of LB fruits revealed that LBQ had a peak at 2972 cm−1 whereas there was no similar peak in LBG and LBQ. A new HPLC method was established for the simultaneous determination of 8 phenolic compounds by quantitative analysis of multiple components by a single marker (QAMS), including 4 phenolic acids (chlorogenic acid, caffeic acid, 4-hydroxycinnamic acid, and ferulic acid), 1 coumarin (scopoletin), and 3 flavonoids (kaempferol-3-O-rutinoside, rutin, and narcissoside). It was showed that rutin was the most dominant phenolic compound in LBQ, although the average content of 4 phenolic acids was also high in LBQ, and scopoletin was the richest in LBG. UHPLC-Q-TOF-MS was used to qualitatively analyze the phenolics, which showed LBN was abundant in phenolic acids, LBQ was rich in flavonoids, and coumarins were the most plentiful in LBG. In conclusion, this study can provide references for the quality control and evaluation of phenolics in LB fruits and their by-products.

[1]  H. Qu,et al.  Discrimination of Geographical Origins of Wolfberry (Lycium barbarum L.) Fruits Using Stable Isotopes, Earth Elements, Free Amino Acids, and Saccharides. , 2022, Journal of agricultural and food chemistry.

[2]  Yingli Wang,et al.  Carotenoid Contents of Lycium barbarum: A Novel QAMS Analyses, Geographical Origins Discriminant Evaluation, and Storage Stability Assessment , 2021, Molecules.

[3]  J. Duan,et al.  Chemical constituents from Lycium barbarum (Solanaceae) and their chemophenetic significance , 2021, Biochemical Systematics and Ecology.

[4]  Qian Lv,et al.  Anti-hypertensive and cardioprotective activities of traditional Chinese medicine-derived polysaccharides: A review. , 2021, International journal of biological macromolecules.

[5]  Li Yang,et al.  Chemical characterization and 5α-reductase inhibitory activity of phenolic compounds in goji berries. , 2021, Journal of pharmaceutical and biomedical analysis.

[6]  Jie Zhang,et al.  Lycium barbarum mitigates radiation injury via regulation of the immune function, gut microbiota, and related metabolites. , 2021, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[7]  J. Yoshino,et al.  Preparation of solid solution and crystal-glass composite consisting of stable phenoxyl radical and its phenol analogue , 2020 .

[8]  D. Barlič-Maganja,et al.  HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Extracts from Two Helichrysum italicum Species , 2020, Metabolites.

[9]  M. Gancarz,et al.  Polyphenol Composition and Antioxidant Potential of Instant Gruels Enriched with Lycium barbarum L. Fruit , 2020, Molecules.

[10]  Zheng Hu,et al.  Design of Thiazolo[5,4-d]thiazole-Bridged Ionic Covalent Organic Polymer for Highly Selective Oxygen Reduction to H2O2 , 2020 .

[11]  Rongxia Liu,et al.  Quantitative analysis of bioactive components in walnut leaves by UHPLC-Q-Orbitrap HRMS combined with QAMS. , 2020, Food chemistry.

[12]  J. Kusz,et al.  Interactions in flavanone and chalcone derivatives: Hirshfeld surface analysis, energy frameworks and global reactivity descriptors. , 2020, Acta crystallographica. Section C, Structural chemistry.

[13]  Yajun Wang,et al.  Changes in Metabolome and Nutritional Quality of Lycium barbarum Fruits from Three Typical Growing Areas of China as Revealed by Widely Targeted Metabolomics , 2020, Metabolites.

[14]  Zhongfu Wang,et al.  Arabinogalactan derived from Lycium barbarum fruit inhibits cancer cell growth via cell cycle arrest and apoptosis. , 2020, International journal of biological macromolecules.

[15]  P. Gabrielli,et al.  Grape Seeds: Chromatographic Profile of Fatty Acids and Phenolic Compounds and Qualitative Analysis by FTIR-ATR Spectroscopy , 2019, Foods.

[16]  Hui Yan,et al.  Lycium barbarum L. leaves ameliorate type 2 diabetes in rats by modulating metabolic profiles and gut microbiota composition. , 2019, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[17]  Xiaoxiong Zeng,et al.  Ultrasonic-assisted extraction and high-speed counter-current chromatography purification of zeaxanthin dipalmitate from the fruits of Lycium barbarum L. , 2019, Food chemistry.

[18]  Shuang Yang,et al.  Quality evaluation of Lycium barbarum (wolfberry) from different regions in China based on polysaccharide structure, yield and bioactivities , 2019, Chinese Medicine.

[19]  Wei Li,et al.  Pro-inflammatory cytokines serve as communicating molecules between the liver and brain for hepatic encephalopathy pathogenesis and Lycium barbarum polysaccharides protection. , 2019, Journal of ethnopharmacology.

[20]  Xuan Zhan,et al.  Effects of Lycium barbarum Polysaccharides on Health and Aging of C. elegans Depend on daf-12/daf-16 , 2019, Oxidative medicine and cellular longevity.

[21]  Xiaoxiong Zeng,et al.  Modulating effects of polysaccharides from the fruits of Lycium barbarum on the immune response and gut microbiota in cyclophosphamide-treated mice. , 2019, Food & function.

[22]  Hui Yan,et al.  Comparison of Functional Components and Antioxidant Activity of Lycium barbarum L. Fruits from Different Regions in China , 2019, Molecules.

[23]  Zhen Yue,et al.  Lycium barbarum polysaccharides promote osteoblasts viability by regulating microRNA‐17/PTEN , 2019, Life sciences.

[24]  R. Chang,et al.  Delay of cone degeneration in retinitis pigmentosa using a 12-month treatment with Lycium barbarum supplement. , 2019, Journal of ethnopharmacology.

[25]  Guiju Sun,et al.  Comparative Metabolic Profiling of Lycium Fruits (Lycium barbarum and Lycium chinense) from Different Areas in China and from Nepal , 2019, Journal of Food Quality.

[26]  G. Rocchetti,et al.  Italian Lycium barbarum L. Berry: Chemical Characterization and Nutraceutical Value , 2018, Natural Product Communications.

[27]  Duangjai Tungmunnithum,et al.  Flavonoids and Other Phenolic Compounds from Medicinal Plants for Pharmaceutical and Medical Aspects: An Overview , 2018, Medicines.

[28]  Shuyin Bao,et al.  Antioxidant effects of Lycium barbarum polysaccharides on photoreceptor degeneration in the light-exposed mouse retina. , 2018, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[29]  Xueqin Ma,et al.  Simultaneous determination of seven phenylethanoid glycosides in Cistanches Herba by a single marker using a new calculation of relative correction factor. , 2018, Journal of separation science.

[30]  Caroline S. Weckerle,et al.  The genus Lycium as food and medicine: A botanical, ethnobotanical and historical review. , 2018, Journal of ethnopharmacology.

[31]  G. Zengin,et al.  UHPLC-QTOF-MS analysis of bioactive constituents from two Romanian Goji (Lycium barbarum L.) berries cultivars and their antioxidant, enzyme inhibitory, and real-time cytotoxicological evaluation. , 2018, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[32]  Jânio Sousa Santos,et al.  Use of principal component analysis (PCA) and hierarchical cluster analysis (HCA) for multivariate association between bioactive compounds and functional properties in foods: A critical perspective , 2018 .

[33]  Chi-Tang Ho,et al.  Use of UHPLC-TripleQ with synthetic standards to profile anti-inflammatory hydroxycinnamic acid amides in root barks and leaves of Lycium barbarum , 2017, Journal of food and drug analysis.

[34]  D. Montesano,et al.  Fatty Acids and Phytosterols to Discriminate Geographic Origin of Lycium barbarum Berry , 2018, Food Analytical Methods.

[35]  Bing Zhang,et al.  Quantitative analysis of multi-components by single marker—a rational method for the internal quality of Chinese herbal medicine , 2017, Integrative medicine research.

[36]  S. Grigorakis,et al.  Phytochemical analysis and antioxidant activity of Lycium barbarum (Goji) cultivated in Greece , 2016, Pharmaceutical biology.

[37]  K. So,et al.  Four new dicaffeoylspermidine derivatives from Lycium barbarum , 2016 .

[38]  Wanpeng Xi,et al.  Functional constituents and antioxidant activities of eight Chinese native goji genotypes. , 2016, Food chemistry.

[39]  Wen Gao,et al.  Rapid separation and identification of multiple constituents in Danhong Injection by ultra-high performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight tandem mass spectrometry. , 2016, Chinese journal of natural medicines.

[40]  O. Chupakhin,et al.  Synthesis and antifungal activity of 3-substituted imidazo[1,2-b][1,2,4,5]tetrazines , 2015, Russian Chemical Bulletin.

[41]  Mingcheng Guo,et al.  Investigation of amino acids in wolfberry fruit (Lycium barbarum) by solid-phase extraction and liquid chromatography with precolumn derivatization , 2015 .

[42]  R. Hemamalini,et al.  Spectroscopic investigation (FTIR spectrum), NBO, HOMO-LUMO energies, NLO and thermodynamic properties of 8-Methyl-N-vanillyl-6-nonenamideby DFT methods. , 2015, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[43]  S. Magiera,et al.  Chromatographic Determination of Phenolic Acids and Flavonoids in Lycium barbarum L. and Evaluation of Antioxidant Activity , 2015, Food Analytical Methods.

[44]  Y. Mabkhot,et al.  Crystal structure of (E)-3-mesityl-1-phenylprop-2-en-1-one, C18H18O , 2014 .

[45]  M. Bronze,et al.  Application of FTIR-ATR to Moscatel dessert wines for prediction of total phenolic and flavonoid contents and antioxidant capacity. , 2014, Food chemistry.

[46]  Qian Chen-qi.  Chemical Composition Analysis and Quality Identification of Gastrodia Tuber in Tibet Based on HPLC-MS , 2014 .

[47]  Satheesh George,et al.  TOTAL PHENOLICS AND FLAVONOIDS IN SELECTED MEDICINAL PLANTS FROM KERALA , 2014 .

[48]  T. H. Roberts,et al.  Techniques for Analysis of Plant Phenolic Compounds , 2013, Molecules.

[49]  Skender Demaku,et al.  Synthesis, Characterization and Antibacterial Studies of 2-Amino-5-{4-(4-amino-4-carboxy-butylamino)- 3-(1-(2-hydroxy-phenylimino)-ethyl)-2-oxo-2H-chromen-7-ylamino}-pentanoic acid and its Metal (II) Complexes , 2013 .

[50]  N. Xu,et al.  Antioxidant Flavonol Compounds from the Marine Cordgrass Spartina anglica , 2013 .

[51]  J. K. Kim,et al.  Metabolomics for the Quality Assessment of Lycium chinense Fruits , 2012, Bioscience, biotechnology, and biochemistry.

[52]  Cuihua Song,et al.  A developed pre-column derivatization method for the determination of free fatty acids in edible oils by reversed-phase HPLC with fluorescence detection and its application to Lycium barbarum seed oil , 2011 .

[53]  Pei Chen,et al.  A non-targeted approach to chemical discrimination between green tea dietary supplements and green tea leaves by HPLC/MS. , 2011, Journal of AOAC International.

[54]  J. Shreeve,et al.  Functionalized Tetrazoles from Cyanogen Azide with Secondary Amines , 2009 .

[55]  R. Pedreschi,et al.  HPLC-DAD characterisation of phenolic compounds from Andean oca (Oxalis tuberosa Mol.) tubers and their contribution to the antioxidant capacity , 2009 .

[56]  A. Urbain,et al.  Ultra-performance liquid chromatography/time-of-flight mass spectrometry as a chemotaxonomic tool for the analysis of Gentianaceae species. , 2009, Phytochemical analysis : PCA.

[57]  H. Matsuda,et al.  Medicinal flowers. XXII. Structures of chakasaponins V and VI, chakanoside I, and chakaflavonoside A from flower buds of Chinese tea plant (Camellia sinensis). , 2008, Chemical & pharmaceutical bulletin.

[58]  Heinz W. Siesler,et al.  A FTIR and 2D-IR Spectroscopic Study on the Microdynamics Phase Separation Mechanism of the Poly(N-isopropylacrylamide) Aqueous Solution , 2008 .

[59]  R. Chang,et al.  Use of Anti-aging Herbal Medicine, Lycium barbarum, Against Aging-associated Diseases. What Do We Know So Far? , 2008, Cellular and Molecular Neurobiology.

[60]  M. Kikuchi,et al.  Five new phenylethanoid glycosides from the whole plants of Lamium purpureum L. , 2006, Chemical & pharmaceutical bulletin.

[61]  Yu-Fei Wang,et al.  Palaeophytochemical constituents of cretaceous Ginkgo coriacea Florin leaves , 2006 .

[62]  W. Cho,et al.  Total synthesis of oxyfagaronine, phenolic benzo[c]phenanthridine and general synthetic way of 2,3,7,8- and 2,3,8,9-tetrasubstituted benzo[c]phenanthridine alkaloids. , 2006, Chemical & pharmaceutical bulletin.

[63]  C. Yin,et al.  3,3a-Dihydrocyclopenta[b]chromen-1(2H)-ones from the reaction of salicylaldehyde and 2-cyclopenten-1-one. , 2005, Acta crystallographica. Section C, Crystal structure communications.

[64]  T. Noro,et al.  Constituents from the bark of Tabebuia impetiginosa. , 2004, Phytochemistry.

[65]  G. Tian,et al.  Structural characterization of the glycan part of glycoconjugate LbGp2 from Lycium barbarum L. , 2001, Carbohydrate research.

[66]  G. Troup,et al.  Development of seed polyphenols in berries from Vitis vinifera L. cv. Shiraz. , 2000 .

[67]  G. Williamson,et al.  Dietary intake and bioavailability of polyphenols. , 2000, The Journal of nutrition.

[68]  D. Athanasopoulos,et al.  Crystal structure of 6-hydroxyflavanone, C15H12O3 , 1998 .

[69]  T. Nohara,et al.  Chemical constituents of Astragali Semen , 1993 .