Abstract
Flavonoids are one of the most widely occurring secondary plant constituents and are rich in vegetable and fruit diets as well as beverages of plant origin. In flavonoid glycosides, the sugars can either be linked to the aglycone via an ether bond (O-glycosides) or via a C–C- bond resulting in flavonoid C-glycosides. Their occurrence in food plants, their role in bioactivity of food, and their catabolism are covered in this chapter. The major class of C-glycosylflavonoids in food plants is represented by flavones, in addition dihydrochalcones and C-glycosylisoflavones can be found. Citrus fruits can be considered as a major source of C-glycosylflavones, whereas in most cases relatively low amounts have been found in cereals. A rich source of C-glycosylated dihydrochalcones are tomatoes, as well as rooibos and honeybush herbal teas, and the most common C-glycosylisoflavone puerarin is mainly consumed via kudzu roots. Due to their higher chemical stability in terms of hydrolysis during cooking and also after ingestion, they can be considered as a specific group within flavonoids. Their metabolic fate is clearly different from O-glycosidic flavonoids with absorption of intact glycosides, followed by phase II metabolization. However, also deglycosylation by gut microbiota and degradation of aglycones to compounds like (hydroxy)phenylpropionic acids have been recognized. Only limited data on the actual daily intake of C-glycosylflavonoids including information on content in fresh and processed food are available.
This is a preview of subscription content, log in via an institution to check access.
Abbreviations
- ABTS:
-
2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt
- CGF:
-
C-glycosylflavonoids
- CGT:
-
C-glycosyltransferase
- COX:
-
Cyclooxygenase
- CYP:
-
Cytochrome P450 enzymes
- DPPH:
-
2,2-diphenyl-1-picrylhydrazyl
- ESI:
-
Electrospray ionization
- IC50:
-
Half maximal inhibitory concentration
- IL:
-
Interleukin
- MCF:
-
Human breast cancer cell line
- MIC:
-
Minimal inhibitory concentration
- mRNA:
-
Messenger RNA
- OGF:
-
O-glycosylflavonoids
- PGE-2:
-
Prostaglandin E2
- P-gp:
-
P-glycoprotein
- PXR:
-
Pregnane-X- receptor
- RAW:
-
Mouse macrophage cell line
- TE:
-
Trolox equivalents
- TNF-α:
-
Tumor necrosis factor α
- Vero:
-
African green monkey kidney cells
References
Abad-Garcia B, Garmon-Lobato S, Berrueta LA et al (2012) On line characterization of 58 phenolic compounds in citrus fruit juices from Spanish cultivars by high-performance liquid chromatography with photodiode-array detection coupled to electrospray ionization triple quadrupole mass spectrometry. Talanta 99:213–224. https://doi.org/10.1016/j.talanta.2012.05.042
An F, Wang S, Tian Q et al (2015) Effects of orientin and vitexin from Trollius chinensis on the growth and apoptosis of esophageal cancer EC-109 cells. Oncol Lett 10(4):2627–2633. https://doi.org/10.3892/ol.2015.3618
Bai J, Zhao S, Fan X et al (2019) Inhibitory effects of flavonoids on P-glycoprotein in vitro and in vivo: food/herb-drug interactions and structure-activity relationships. Toxicol Appl Pharmacol 369:49–59. https://doi.org/10.1016/j.taap.2019.02.010
Barreca D, Bellocco E, Caristi C (2010) Distribution of C- and O-glycosyl flavonoids, (3-hydroxy-3-methylglutaryl) glycosyl flavanones and furocumarins in Citrus aurantium L. juice. Food Chem 124(2):576–582. https://doi.org/10.1016/j.foodchem.2010.06.076
Barreca D, Bisignano C, Ginestra G et al (2013) Polymethoxylated, C- and O-glycosyl flavonoids in tangelo (Citrus reticulata x Citrus paradisi) juice and their influence on antioxidant properties. Food Chem 141(2):1481–1488. https://doi.org/10.1016/j.foodchem.2013.03.095
Barreca D, Bellocco E, Leuzzi U et al (2014) Flavonoid C-glycosides in citrus juices from southern Italy: distribution and influence on the antioxidant activity. ACS Symp Ser 1185:189–200. https://doi.org/10.1021/bk-2014-1185.ch009
Barreca D, Gattuso G, Lagana G et al (2016) C- and O-glycosyl flavonoids in Sanguinello and Tarocco blood orange (Citrus sinsensis (L.) Osbeck) juice: identification and influence on antioxidant properties and acetylcholinesterase activity. Food Chem 196:619–627. https://doi.org/10.1016/j.foodchem.2015.09.098
Boncompagni E, Orozco-Arroyo G, Cominelli E et al (2018) Antinutritional factors in pearl millet grains: phytate and goitrogens content variability and molecular characterization of genes involved in their pathways. PLoS One 13(6):e0198394/1–e0198394/30. https://doi.org/10.1371/journal.pone.0198394
Borghi SM, Carvalho TT, Staurengo-Ferrari L et al (2013) Vitexin inhibits inflammatory pain in mice by targeting TRPV1, oxidative stress, and cytokines. J Nat Prod 76(6):1141–1149. https://doi.org/10.1021/np400222v
Braune A, Blaut M (2016) Bacterial species involved in the conversion of dietary flavonoids in the human gut. Gut Microbes 7(3):216–234. https://doi.org/10.1080/19490976.2016.1158395
Brazier-Hicks M, Evans KM, Gershater MC et al (2009) The C-glycosylation of flavonoids in cereals. J Biol Chem 284(27):17926–17934. https://doi.org/10.1074/jbc.M109.009258
Bustos PS, Deza-Ponzio R, Paez PL et al (2018) Flavonoids as protective agents against oxidative stress induced by gentamicin in systemic circulation. Potent protective activity and microbial synergism of luteolin. Food Chem Toxicol 118:294–302. https://doi.org/10.1016/j.fct.2018.05.030
Cai S, Chen Y, Zhang W et al (2013) Comparative study on the excretion of vitexin-4″-O-glucoside in mice after oral and intravenous administration by using HPLC. Biomed Chromatogr 27(11):1375–1379. https://doi.org/10.1002/bmc.2931
Cao H, Liu X, Ulrih NP et al (2019) Plasma protein binding of dietary polyphenols to human serum albumin: a high performance affinity chromatography approach. Food Chem 270:257–263. https://doi.org/10.1016/j.foodchem.2018.07.111
Cardoso CAL, Coelho RG, Honda NK et al (2013) Phenolic compounds and antioxidant, antimicrobial and antimycobacterial activities of Serjania erecta Radlk. (Sapindaceae). Braz J Pharm Sci 49(4):775–782. https://doi.org/10.1590/S1984-82502013000400017
Caristi C, Bellocco E, Gargiulli C et al (2005) Flavone-di-C-glycosides in citrus juices from southern Italy. Food Chem 95(3):431–437. https://doi.org/10.1016/j.foodchem.2005.01.031
Chen GL, Fan MX, Wu JL et al (2019) Antioxidant and anti-inflammatory properties of flavonoids from lotus plumule. Food Chem 277:706–712. https://doi.org/10.1016/j.foodchem.2018.11.040
Courts F, Williamson G (2015) The occurrence, fate and biological activities of C-glycosyl flavonoidsin the human diet. Crit Rev Food Sci Nutr 55(10):1352–1367. https://doi.org/10.1080/10408398.2012.694497
Crozier A, Del Rio D, Clifford MN (2010) Bioavailability of dietary flavonoids and phenolic compounds. Mol Asp Med 31(6):446–467. https://doi.org/10.1016/j.mam.2010.09.007
Czubinski J, Wroblewska K, Czyzniejewski M et al (2019) Bioaccessibility of defatted lupin seed phenolic compounds in a standardized static in vitro digestion system. Food Res Int 116:1126–1134. https://doi.org/10.1016/j.foodres.2018.09.057
Del Rio D, Rodriguez-Mateos A, Spencer JPE et al (2013) Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxid Redox Sign 18(14):1818–1892. https://doi.org/10.1089/ars.2012.4581
Di Pietro A, Conseil G, Perez-Victoria JM et al (2002) Modulation by flavonoids of cell multidrug resistance mediated by P-glycoprotein and related ABC transporters. Cell Mol Life Sci 59(2):307–322. https://doi.org/10.1007/s00018-002-8424-8
Elliger CA, Chan BG, Waiss AC et al (1980) C-Glycosylflavones from Zea mays that inhibit insect development. Phytochemistry 19(2):293–297. https://doi.org/10.1016/S0031-9422(00)81977-9
Ezzat SM, Raslan M, Salama MM et al (2019) In vivo anti-inflammatory activity and UPLC-MS/MS profiling of the peels and pulps of Cucumis melo var. cantalupensis and Cucumis melo var. reticulatus. J Ethnopharmacol 237:245–254. https://doi.org/10.1016/j.jep.2019.03.015
Fantoukh OI, Dale OR, Parveen A et al (2019) Safety assessment of phytochemicals derived from the globalized south African rooibos tea (Aspalathus linearis) through interaction with CYP, PXR, and P-gp. J Agric Food Chem 67(17):4967–4975. https://doi.org/10.1021/acs.jafc.9b00846
Ferreres F, Silva BM, Andrade PB et al (2003) Approach to the study of C-glycosyl flavones by ion trap HPLC-PAD-ESI/MS/MS: application to seeds of quince (Cydonia oblonga). Phytochem Anal 14(6):352–359. https://doi.org/10.1002/pca.727
Ferreres F, Goncalves RF, Gil-Izquierdo A et al (2012) Further knowledge on the phenolic profile of Colocasia esculenta (L.) Shott. J Agric Food Chem 60(28):7005–7015. https://doi.org/10.1021/jf301739q
Figueirinha A, Paranhos A, Perez-Alonso JJ et al (2008) Cymbopogon citratus leaves: characterization of flavonoids by HPLC-PDA-ESI/MS/MS and an approach to their potential as a source of bioactive polyphenols. Food Chem 110(3):718–728. https://doi.org/10.1016/j.foodchem.2008.02.045
Gaitan E, Cooksey RC, Legan J et al (1995) Antithyroid effects in vivo and in vitro of vitexin: a C-glucosylflavone in millet. J Clin Endocrinol Metab 80(4):1144–1147. https://doi.org/10.1210/jcem.80.4.7714083
Gorzalczany S, Marrassini C, Mino J et al (2011) Antinociceptive activity of ethanolic extract and isolated compounds of Urtica circularis. J Ethnopharmacol 134(3):733–738. https://doi.org/10.1016/j.jep.2011.01.025
Hattori M, Shu Y-Z, El-Sedawy AI, Namba T (1998) Metabolism of homoorientin by human intestinal bacteria. J Nat Prod 51(5):874–878
Hirawan R, Beta T (2011) C-glycosylflavone and lignan diglucoside contents of commercial, regular, and whole-wheat spaghetti. Cereal Chem 88(4):338–343. https://doi.org/10.1094/CCHEM-01-10-0010
Hostetler GL, Ralston RA, Schwartz SJ (2017) Flavones: food sources, bioavailability, metabolism, and bioactivity. Adv Nutr 8(3):423–435. https://doi.org/10.3945/an.116.012948
Kadaikunnan S, Rejiniemon TS, Alharbi NS et al (2015) Identification and quantification of phenolic compounds from Trigonella foenum graecum L. and its in-vitro antioxidant, anticancer and antimicrobial activities. Fresenius Environ Bull 24(8a):2643–2649
Kubacey TM, Haggag EG, El-Toumy SA et al (2012) Biological activity and flavonoids from Centaurea alexanderina leaf extract. J Pharm Res 5(6):3352–3361
Kumari S, Raines JM, Martin JM et al (2015) Thermal stability of kudzu root (Pueraria Radix) isoflavones as additives to beef patties. J Food Sci Technol 52(3):1578–1585. https://doi.org/10.1007/s13197-013-1112-x
Li SS, Wu J, Chen LG et al (2014) Biogenesis of C-glycosyl flavones and profiling of flavonoid glycosides in lotus (Nelumbo nucifera). PLoS One 9(10):e108860/1–e108860/11. https://doi.org/10.1371/journal.pone.0108860
Lou SN, Lai YC, Hsu YS et al (2016) Phenolic content, antioxidant activity and effective compounds of kumquat extracted by different solvents. Food Chem 197(A):1–6. https://doi.org/10.1016/j.foodchem.2015.10.096
Mashima K, Mayu H, Suzuki H, Shimosaka M, et al (2019) Identification and characterization of apigenin6-C-Glucosyltransferase involved in biosynthesis ofisosaponarin in Wasabi (Eutrema japonicum). Plant Cell Physiol 0(0):1–11. https://doi.org/10.1093/pcp/pcz164. Advance Access publication on 16 August 2019, available online at https://academic.oup.com/pcp
Materska M (2015) Flavone C-glycosides from Capsicum annuum L.: relationships between antioxidant activity and lipophilicity. Eur Food Res Technol 240(3):549–557. https://doi.org/10.1007/s00217-014-2353-2
McNally DJ, Wurms KV, Labbe C et al (2003) Complex C-Glycosyl flavonoid Phytoalexins from Cucumis sativus. J Nat Prod 66(9):1280–1283. https://doi.org/10.1021/np030150y
Mohamed RS, Marrez DA, Salem SH et al (2019) Hypoglycemic, hypolipidemic and antioxidant effects of green sprouts juice and functional dairy micronutrients against streptozotocin-induced oxidative stress and diabetes in rats. Heliyon 5(2):e01197. https://doi.org/10.1016/j.heliyon.2019.e01197
Ninfali P, Antonini E, Frati A et al (2017) C-glycosyl flavonoids from Beta vulgaris Cicla and Betalains from Beta vulgaris rubra: antioxidant, anticancer and antiinflammatory activities – a review. Phytother Res 31(6):871–884. https://doi.org/10.1002/ptr.5819
Nix A, Paull CA, Colgrave M (2015) The flavonoid profile of pigeonpea, Cajanus cajan: a review. Springerplus 4(1):1–6. https://doi.org/10.1186/s40064-015-0906-x
Pereira-Caro G, Cros G, Yokota T et al (2013) Phtyochemical profiles of black, red, brown, and white rice from Camargue region of France. J Agric Food Chem 61(33):7976–7986. https://doi.org/10.1021/jf401937b
Picariello G, Sciammaro L, Siano F et al (2017) Comparative analysis of C-glycosidic flavonoids from Prosopis spp. and Ceratonia siliqua seed germ flour. Food Res Int 99(1):730–738. https://doi.org/10.1016/j.foodres.2017.06.058
Popovici G, Weissenboeck G (1976) Changes in the flavonoid pattern during development of Avena sativa L. Ber Deut Bot Ges 89(2–3):483–489
Sahreen S, Khan MR, Khan RA et al (2013) Estimation of flavoniods, antimicrobial, antitumor and anticancer activity of Carissa opaca fruits. BMC Complement Altern Med 13:372/1–372/7. https://doi.org/10.1186/1472-6882-13-372
Schulze AE, Beelders T, Koch IS et al (2015) Honeybush herbal teas (Cyclopia spp.) contribute to high levels of dietary exposure to xanthones, benzophenones, dihydrochalcones and other bioactive phenolics. J Food Compos Anal 44:139–148. https://doi.org/10.1016/j.jfca.2015.08.002
Siciliano T, De Tommasi N, Morelli I et al (2004) Study of flavonoids of Sechium edule (Jacq) Swartz (Cucurbitaceae) different edible organs by liquid chromatography photodiode array mass spectrometry. J Agric Food Chem 52(21):6510–6515. https://doi.org/10.1021/jf040214q
Stark T, Hofmann T (2006) Application of a molecular sensory science approach to alkalized cocoa (Theobroma cacao): structure determination and sensory activity of nonenzymatically C-glycosylated flavan-3-ols. J Agric Food Chem 54(25):9510–9521. https://doi.org/10.1021/jf062403+
Vallejo F, Marin JG, Tomas-Barberan FA (2012) Phenolic compound content of fresh and dried figs (Ficus carica L.). Food Chem 130(3):485–492. https://doi.org/10.1016/j.foodchem.2011.07.032
Van Dooren I, Foubert K, Bijttebier S et al (2018) In vitro gastrointestinal biotransformation and characterization of a Desmodium adscendens decoction: the first step in unravelling its behaviour in the human body. J Pharm Pharmacol 70(10):1414–1422. https://doi.org/10.1111/jphp.12978
Vukics V, Guttman A (2009) Structural characterization of flavonoid glycosides by multi-stage mass spectrometry. Mass Spectrom Rev 29(1):1–16. https://doi.org/10.1002/mas.20212
Wang S, Yang C, Tu H et al (2017) Characterization and metabolic diversity of flavonoids in citrus species. Sci Rep 7(1):1–10. https://doi.org/10.1038/s41598-017-10970-2
Wang Y, Liu M, Liu L et al (2018) The structural revision and total synthesis of Carambolaflavone A. J Org Chem 83(7):4111–4118. https://doi.org/10.1021/acs.joc.8b00008
Waridel P, Wolfender JL, Ndjoko K et al (2001) Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. J Chromatogr A 926(1):29–41. https://doi.org/10.1016/S0021-9673(01)00806-8
Webster FH, Wood PJ (eds) (2016) Oats – chemistry and technology, 2nd edn. Woodhead Publishing and AACC International Press, Eagan
Wijaya GY, Mares DJ (2012) Apigenin di-C-glycosides (ACG) content and composition in grains of bread wheat (Triticum aestivum) and related species. J Cereal Sci 56(2):260–267. https://doi.org/10.1016/j.jcs.2012.06.007
Williams CA, Harborne JB, Clifford HT (1973) Negatively charged flavones and tricin as chemosystematic markers in the Palmae. Phtyochemistry 12(10):2417–2430. https://doi.org/10.1016/0031-9422(73)80449-2
Wu QL, Yang YH, Simon J (2011) Chemical profiling and quantification of isoflavone phytoestrogens in kudzu using LC/UV/MSD. Am J Anal Chem 2(6):665–674. https://doi.org/10.4236/ajac.2011.26076
Xiang J, Apea-Bah FB, Ndolo VU et al (2019) Profile of phenolic compounds and antioxidant activity of finger millet varieties. Food Chem 275:361–368. https://doi.org/10.1016/j.foodchem.2018.09.120
Xiao J (2017) Dietary flavonoid aglycones and their glycosides: which show better biological significance? Crit Rev Food Sci Nutr 57(9):1874–1905. https://doi.org/10.1080/10408398.2015.1032400
Xiao J, Capanoglu E, Jassbi AR et al (2016) Advance on the flavonoid C-glycosides and health benefits. Crit Rev Food Sci Nutr 56(1):S29–S45. https://doi.org/10.1080/10408398.2015.1067595
Xiong F, Wang H, Jiang Z et al (2015) Integrated pharmacokinetics and biodistribution of multiple flavonoid C-glycosides components in rat after oral administration of Abrus mollis extract and correlations with bio-effects. J Ethnopharmacol 163:290–296. https://doi.org/10.1016/j.jep.2014.12.067
Xu J, Qian D, Jiang S et al (2014) Application of ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry to determine the metabolites of orientin produced by human intestinal bacteria. J Chromatogr B 944:123–127. https://doi.org/10.1016/j.jchromb.2013.11.002
Zhang Y, Tie X, Bao B et al (2007) Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. Br J Nutr 97(3):484–494. https://doi.org/10.1017/S0007114507336830
Zhang M, Nan H, Wang Y et al (2014) Comparison of flavonoid compounds in the flavedo and juice of two pummelo cultivars (Citrus grandis L. Osbeck) from different cultivation regions in China. Molecules 19(11):17314–17328. https://doi.org/10.3390/molecules191117314
Zu YG, Liu XL, Fu YJ et al (2010) Chemical composition of the SFE-CO2 extracts from Cajanus cajan (L.) Huth and their antimicrobial activity in vitro and in vivo. Phytomedicine 17(14):1095–1101. https://doi.org/10.1016/j.phymed.2010.04.005
Zucolotto SM, Fagundes C, Reginatto FH et al (2012) Analysis of C-glycosyl flavonoids from south American Passiflora species by HPLC-DAD and HPLC-MS. Phytochem Anal 23(3):232–239. https://doi.org/10.1002/pca.1348
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2020 Springer Nature Singapore Pte Ltd.
About this entry
Cite this entry
Bucar, F., Xiao, J.B., Ochensberger, S. (2020). Flavonoid C-Glycosides in Diets. In: Xiao, J., Sarker, S., Asakawa, Y. (eds) Handbook of Dietary Phytochemicals. Springer, Singapore. https://doi.org/10.1007/978-981-13-1745-3_6-1
Download citation
DOI: https://doi.org/10.1007/978-981-13-1745-3_6-1
Received:
Accepted:
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-13-1745-3
Online ISBN: 978-981-13-1745-3
eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences