Skip to main content

Chalcones in Diets

  • Reference work entry
  • First Online:
Handbook of Dietary Phytochemicals

Abstract

Chalcones are plant-derived polyphenolic compounds commonly found in edible plants such as tomatoes, apples, licorice, and fingerroot. The molecular structure of two aromatic rings connected by three carbons with conjugated carbonyl group and double bond results in the yellow or orange color of chalcones. The compound is biosynthetically available through chalcone synthase pathway and structurally related to flavanone and anthraquinone. A wide range of biological activities were found to be associated with natural chalcones from food and these activities havebeen proven to be contributed by the keto-ethylenic group in the main structure of chalcones. The biological activities reported include antioxidant, antimicrobial, anticancer, anti-inflammatory, antihypertensive, antidiabetic, anti-obesity, anti-neuroprotective, and hepatoprotective effects. Moreover, these chalcones have excellent profile in terms of food safety by showing non-toxicity against normal cells through a number of animal and human clinical studies. The overall beneficial effects of chalcones revealed that these compounds are highly nutritious and safe to be consumed, as well as highly potential lead compounds to be further developed into alternative drugs to treat various diseases.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 649.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 699.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

References

  • Adam A, Crespy V, Levrat-Verny MA et al (2002) The bioavailability of ferulic acid is governed primarily by the food matrix rather than its metabolism in intestine and liver in rats. J Nutr 132:1962–1968

    Article  CAS  PubMed  Google Scholar 

  • Alonso-Salces RM, Herrero C, Barranco A (2006) Polyphenolic compositions of Basque natural ciders: a chemometric study. Food Chem 97:438–446

    Article  CAS  Google Scholar 

  • Amiot MJ, Tacchini M, Aubert S (1992) Phenolic composition and browning susceptibility of various apple cultivars at maturity. J Food Sci 57:958–962

    Article  CAS  Google Scholar 

  • Andreotti C, Costa G, Treutter D (2006) Composition of phenolic compounds in pear leaves as affected by genetics, ontogenesis and the environment. Sci Hortic 109:130–137

    Article  CAS  Google Scholar 

  • Aratsu C, Ehata T, Miyataka S (2003) Japan Patent JP2003238417A

    Google Scholar 

  • Asero R, Mistrello G, Roncarolo D et al (2000) Lipid transfer protein: a pan-allergen in plant-derived foods that is highly resistant to pepsin digestion. Int Arch Allergy Immunol 122:20–32

    Article  CAS  PubMed  Google Scholar 

  • Ashfaq UA, Masoud MS, Nawaz Z et al (2011) Glycyrrhizin as antiviral agent against hepatitis C virus. J Transl Med 9:112

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Asl MN, Hosseinzadeh H (2008) Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. Phytother Res 724:709–724

    Article  CAS  Google Scholar 

  • Atef Y, El-Fayoumi HM, Abdel-Mottaleb Y et al (2017) Effect of cardamonin on hepatic ischemia reperfusion induced in rats: role of nitric oxide. Eur J Pharmacol 815:446–453

    Article  CAS  PubMed  Google Scholar 

  • Baba K, Nakata K, Taniguchi M et al (1990) Chalcones from Angelica keiskei. Phytochemistry 29:3907–3910

    Article  CAS  Google Scholar 

  • Ballester A-R, Molthoff J, de Vos R et al (2010) Biochemical and molecular analysis of pink tomatoes: deregulated expression of the gene encoding transcription factor SIMYB12 leads to pink tomato fruit color. Plant Physiol 152:71–84

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Boeck P, Leal PC, Yunes RA et al (2005) Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones. Arch Pharm Chem Life Sci 338:87–95

    Article  CAS  Google Scholar 

  • Borrego F, Canales I, Lindley MG (1995) Neohesperidin dihydrochalcone: state of knowledge review. Z Lebensm Unters Forsch 200:32–37

    Article  CAS  Google Scholar 

  • Bors W, Heller W, Michel C et al (1990) Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol 186:343–355

    Article  CAS  PubMed  Google Scholar 

  • Bovy A, de Vos R, Kemper M et al (2002) High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1. Plant Cell 14:2509–2526

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bremner P, Meyer J (1998) Pinocembrin Chalcone: An Antibacterial Compound from Helichrysum trilineatum. Planta Medica 64(8):777–777

    Google Scholar 

  • Bugianesi R, Salucci M, Leonardi C (2004) Effect of domestic cooking on human bioavailability of naringenin, chlorogenic acid, lycopene and beta-carotene in cherry tomatoes. Eur J Nutr 43:360–366

    Article  CAS  PubMed  Google Scholar 

  • Burda S, Oleszek W, Lee CY (1998) Phenolic compounds and their changes in apples during maturation and cold storage. J Agric Food Chem 38:945–948

    Article  Google Scholar 

  • Burt S (2004) Essential oils: their antibacterial properties and potential applications in foods-A review. Int J Food Microbiol 94:223–253

    Article  CAS  PubMed  Google Scholar 

  • Calliste C, Le Bail J, Trouillas P et al (2001) Chalcones: structural requirements for antioxidant estrogenic and antiproliferative activities. Anticancer Res 21:3949–3956

    CAS  PubMed  Google Scholar 

  • Capanoglu E, Beekwilder J, Boyacioglu D (2008) Changes in antioxidants and metabolite profiles during production of tomato paste. J Agric Food Chem 56:964–973

    Article  CAS  PubMed  Google Scholar 

  • Challice J (1981) Chemotaxonomic studies in the family Rosaceae and the evolutionary origins of the subfamily Maloideae. Preslia 53:289–301

    Google Scholar 

  • Chan EWC, Lim YY, Wong LF et al (2008) Antioxidant and tyrosinase inhibition properties of leaves and rhizomes of ginger species. Food Chem 109:477–483

    Article  CAS  Google Scholar 

  • Charoensin S, Punvittayagul C, Pompimon W (2010) Toxicological and clastogenic evaluation of pinocembrin and pinostrobin isolated from Boesenbergia pandurata in Wistar rats. Thai J Toxicol 25:29–40

    Google Scholar 

  • Cheenpracha S, Karalai C, Ponglimanont C et al (2006) Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata. Bioorg Med Chem 14:1710–1714

    Article  CAS  PubMed  Google Scholar 

  • Chin YW, Jung HA, Liu Y (2007) Anti-oxidant constituents of the roots and stolons of licorice (Glycyrrhiza glabra). J Agric Food Chem 55:4691–4697

    Article  CAS  PubMed  Google Scholar 

  • Chinnici F, Gaiani A, Natali N et al (2004) Improved HPLC determination of phenolic compounds in Cv. Golden delicious apples using a monolithic column. J Agric Food Chem 52:3–7

    Article  CAS  PubMed  Google Scholar 

  • Cho YC, Lee SH, Yoon G et al (2010) Licochalcone E reduces chronic allergic contact dermatitis and inhibits IL-12p40 production through down-regulation of NF-κB. Int Immunopharmacol 10:1119–1126

    Article  CAS  PubMed  Google Scholar 

  • Chow EJ, Sediva I (2013) Influenza A infection and anaphylaxis in a pediatric patient hospitalized for asthma exacerbation. R I Med J 100:35–36

    Google Scholar 

  • Chu X, Jiang L, Wei M et al (2013) Attenuation of allergic airway inflammation in a murine model of asthma by Licochalcone A. Immunopharmacol Immunotoxicol 35:653–661

    Article  PubMed  Google Scholar 

  • Chularojanamontri L, Tuchinda P, Kulthanan K et al (2016) A double-blinded, randomized, vehicle-controlled study to access skin tolerability and efficacy of an anti-inflammatory moisturizer in treatment of acne with 0.1% adapalene gel. J Dermatol Treat 27:140–145

    Article  CAS  Google Scholar 

  • Chung PP, Mohamad TAST, Akhtar MN et al (2018) Antinociceptive effects of cardamonin in mice: possible involvement of trpv1, glutamate, and opioid receptors. Molecules 23:2237

    Article  CAS  Google Scholar 

  • Crespy V, Aprikian O, Morand C et al (2001a) Bioavailability of phloretin and phloridzin in rats. J Nutr 131:3227–3230

    Article  CAS  PubMed  Google Scholar 

  • Crespy V, Morand C, Besson C et al (2001b) Comparison of the intestinal absorption of quercetin, phloretin and their glucosides in rats. J Nutr 131:2109–2114

    Article  CAS  PubMed  Google Scholar 

  • Damazio RG, Zanatta AP, Cazarolli LH et al (2010) Antihyperglycemic activity of naphthylchalcones. Eur J Med Chem 45:1332–1337

    Article  CAS  PubMed  Google Scholar 

  • Dao TT, Nguyen PH, Lee HS et al (2011a) Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata. Bioorg Med Chem Lett 21:294–298

    Article  CAS  PubMed  Google Scholar 

  • Dao TTH, Linthorst HJM, Verpoorte R (2011b) Chalcone synthase and its functions in plant resistance. Phytochem Rev 10:397–412

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Delphi L, Sepehri H (2016) Apple pectin: a natural source for cancer suppression in 4T1 breast cancer cells in vitro and express p53 in mouse bearing 4T1 cancer tumors, in vivo. Biomed Pharmacother 84:637e44

    Article  CAS  Google Scholar 

  • Di Lecce G, Martínez-Hueĺamo M, Tulipani S et al (2013) Setup of a UHPLC−QqQ-MS method for the analysis of phenolic compounds in cherry tomatoes, tomato sauce, and tomato juice. J Agric Food Chem 61:8373–8380

    Article  PubMed  CAS  Google Scholar 

  • Diamandis P, Tyers M, Dirks PB (2008) Canada Patentn CA2606658A1

    Google Scholar 

  • Dinkova-Kostova AT, Abeygunawardana C, Talalay P (1998) Chemoprotective properties of phenyl propenoids, bis (benzylidene) cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers. J Med Chem 41:5287–5296

    Article  CAS  PubMed  Google Scholar 

  • Dogukan A, Tuzcu M, Agca CA et al (2011) A tomato lycopene complex protects the kidney from cisplatin-induced injury via affecting oxidative stress as well as bax, bcl-2, and hsps expression. Nutr Cancer 63:427–434

    Article  CAS  PubMed  Google Scholar 

  • Dolatowski ZJ, Stadnik J, Stasiak D (2007) Applications of ultrasound in food technology. Acta Sci Pol Technol Aliment 6:89–99

    Google Scholar 

  • Dong X, Du L, Pan Z et al (2010) Synthesis and biological evaluation of novel hybrid chalcone derivatives as vasorelaxant agents. Eur J Med Chem 45:3986–3992

    Article  CAS  PubMed  Google Scholar 

  • Dziedzic SZ, Hudson BJF, Barnes G (1985) Polyhydroxydihydrochalcones as antioxidants for lard. J Agric Food Chem 33:244–246

    Article  CAS  Google Scholar 

  • Ehrenkranz JRL (2006) US Patent US20060189512A1

    Google Scholar 

  • Enoki T, Ohnogi H, Nagamine K et al (2007) Antidiabetic activities of chalcones isolated from a Japanese herb, Angelica keiskei. J Agric Food Chem 55:6013–6017

    Article  CAS  PubMed  Google Scholar 

  • Fenwick G, Lutomski J, Nieman C (1990) Glycyrrhiza glabra L. (Liquorice): composition, uses and analysis. Food Chem 38:119–143

    Article  CAS  Google Scholar 

  • Fischer TC, Gosch C, Pfeiffer J (2007) Flavonoid genes of pear (Pyrus communis). Trees 21:521–529

    Article  CAS  Google Scholar 

  • Foetisch K, Son D, Altmann F et al (2001) Tomato (Lycopersicon esculentum) allergens in pollen-allergic patients. Eur Food Res Technol 213:259–266

    Article  CAS  Google Scholar 

  • Friedlander JI, Shorter B, Moldwin RM (2012) Diet and its role in interstitial cystitis/bladder pain syndrome (IC/BPS) and comorbid conditions. BJU Int 109:15841591

    Article  Google Scholar 

  • Fu Y, Zhou E, Wei Z et al (2014) Glycyrrhizin inhibits the inflammatory response in mouse mammary epithelial cells and a mouse mastitis model. FEBS J 281:2543–2557

    Article  CAS  PubMed  Google Scholar 

  • Fujioka H, Nakahara K, Oki T et al (2010) The first asymmetric total syntheses of both enantiomers of cryptocaryone. Tetrahedron Lett 51:1945–1946

    Article  CAS  Google Scholar 

  • Fujiwara K, Nakashima S, Sami M et al (2013) Ninety-day dietary toxicity study of apple polyphenol extracts in Crl: CD (SD) rats. Food Chem Toxicol 56:214–222

    Article  CAS  PubMed  Google Scholar 

  • Furusawa J, Funakoshi-Tago M, Mashino T et al (2009) Glycyrrhiza inflata-derived chalcones, Licochalcone A, Licochalcone B and Licochalcone D, inhibit phosphorylation of NF-κB p65 in LPS signaling pathway. Int Immunopharmacol 9:499–507

    Article  CAS  PubMed  Google Scholar 

  • Gafner F, Schmid D, Lozza J et al (2013) Tetra-carboxy-methyl-naringenin-chalcone, a new active to treat rosacea. Househ Pers Care Today 8:14–16

    Google Scholar 

  • Gahler S, Otto K, Bohm V (2003) Alterations of vitamin C, total phenolics, and antioxidant capacity as affected by processing tomatoes to different products. J Agric Food Chem 51:7962–7968

    Article  CAS  PubMed  Google Scholar 

  • Galicia-Cabrera RM (2007) Tomato processing. In: Hui YH (ed) Handbook of food products manufacturing. Wiley-Interscience, Hoboken, pp 1091–1121

    Chapter  Google Scholar 

  • Gann PH, Ma J, Giovannucci E et al (1999) Lower prostate cancer risk in men with elevated plasma lycopene levels: results of a prospective analysis. Cancer Res 59:1225–1230

    CAS  PubMed  Google Scholar 

  • Gaur R, Yadav KS, Verma RK et al (2014) In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin. Phytomedicine 21:415–422

    Article  CAS  PubMed  Google Scholar 

  • Geissman TA (1941) Anthochlor pigments. The pigment of Coreopsis douglasii. J Am Chem Soc 63:656–658

    Article  CAS  Google Scholar 

  • Geyer JA, Keenan SM, Woodard CL et al (2009) Selective inhibition of Pfmrk, a Plasmodium falciparum CDK, by antimalarial 1, 3-diaryl-2-propenones. Bioorg Med Chem Lett 19:1982–1985

    Article  CAS  PubMed  Google Scholar 

  • Glöck I, Blaschke G, Veit M (2001) Validated methods for direct determination of hydroquinone and sulfate in human urine after oral intake of bearberry leaf extract by capillary zone electrophoresis. J Chromatogr B 761:261–266

    Article  Google Scholar 

  • Gómez-Romero M, Segura-Carretero A, Fernández-Gutiérrez A (2010) Metabolite profiling and quantification of phenolic compounds in methanol extracts of tomato fruit. Phytochemistry 71:1848–1864

    Article  PubMed  CAS  Google Scholar 

  • Gosch C, Halbwirth H, Kuhn J et al (2009) Biosynthesis of phloridzin in apple (Malus domestica Borkh.). Plant Sci 176:223–231

    Article  CAS  Google Scholar 

  • Gosch C, Halbwirth H, Stich K (2010a) Phloridzin: biosynthesis, distribution and physiological relevance in plants. Phytochemistry 71:838–843

    Article  CAS  PubMed  Google Scholar 

  • Gosch C, Halbwirth H, Schneider B (2010b) Cloning and heterologous expression of glycosyltransferases from Malus x domestica and Pyrus communis, which convert phloretin to phloretin 2′-O-glucoside (phloridzin). Plant Sci 178:299–306

    Google Scholar 

  • Grieb SMD, Theis RP, Burr D et al (2009) Food groups and renal cell carcinoma: results from a case-control study. J Am Diet Assoc 109:656–667

    Article  PubMed  Google Scholar 

  • Guo J, Liu A, Cao H et al (2008) Biotransformation of the chemopreventive agent 2′,4′,4-trihydroxychalcone (isoliquiritigenin) by udp-glucuronosyltransferases. Drug Metab Dispos 36:2104–2112

    Article  CAS  PubMed  Google Scholar 

  • Han B, Zhao H (2010) Effects of hydroxysafflor yellow A in the attenuation of MPTP neurotoxicity in mice. Neurochem Res 35:107–113

    Article  CAS  PubMed  Google Scholar 

  • Haraguchi H, Tanimoto K, Tamura Y et al (1998) Mode of antibacterial action of retrochalcones from Glycyrrhiza inflata. Phytochemistry 48:125e129

    Article  Google Scholar 

  • Hassan M, El Yazidi C, Landrier JF et al (2007) Phloretin enhances adipocyte differentiation and adiponectin expression in 3T3-L1 cells. Biochem Biophys Res Commun 361:208–213

    Article  CAS  PubMed  Google Scholar 

  • Hatziieremia S, Gray AI, Ferro VA et al (2006) The effects of cardamonin in lipopolysaccharide-induced inflammatory protein production and MAP kinase and NFκB signalling pathways in monocytes/macrophages. Br J Pharmacol 149:188–198

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hayat F, Salahuddin A, Umar S et al (2010) Synthesis, characterization, antiamoebic activity and cytotoxicity of novel series of pyrazoline derivatives bearing quinoline tail. Eur J Med Chem 45:4669–4675

    Article  CAS  PubMed  Google Scholar 

  • He Y, Yang L, Liu Y et al (2009) Characterization of cardamonin metabolism by P450 in different species via HPLC-ESI-ion trap and UPLC-ESI-quadrupole mass spectrometry. Acta Pharmacol Sin 30:1462–1470

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hirai S, Kim YI, Goto T et al (2007) Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages. Life Sci 81:1272–1279

    Article  CAS  PubMed  Google Scholar 

  • Honda H, Nagai Y, Matsunaga T (2014) Isoliquiritigenin is a potent inhibitor of NLRP3 inflammasome activation and diet-induced adipose tissue inflammation. J Leukoc Biol 96:1087–1100

    Article  PubMed  CAS  Google Scholar 

  • Horiba T, Nishimura I, Nakai Y et al (2010) Naringenin chalcone improves adipocyte functions by enhancing adiponectin production. Mol Cell Endocrinol 323:208–214

    Article  CAS  PubMed  Google Scholar 

  • Hua X, Fu YJ, Zu YG et al (2010) Plasma pharmacokinetics and tissue distribution study of cajaninstilbene acid in rats by liquid chromatography with tandem mass spectrometry. J Pharm Biomed Anal 52:273–279

    Article  CAS  PubMed  Google Scholar 

  • Huang L, Nikolic D, van Breemen RB (2017) Hepatic metabolism of licochalcone A, a potential chemopreventive chalcone from licorice (Glycyrrhiza inflata), determined using liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem 409:6937–6948

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hudson BJF, Lewis JI (1983) Polyhydroxy flavonoid antioxidants for edible oils. Structural criteria for activity. Food Chem 10:47–55

    Article  CAS  Google Scholar 

  • Iijima Y, Suda K, Suzuki T et al (2008) Metabolite profiling of Chalcones and flavanones in tomato fruit. J Jpn Soc Hortic Sci 77:94–102

    Article  CAS  Google Scholar 

  • Ingarsal N, Saravanan G, Amutha P et al (2007) Synthesis, in vitro antibacterial and antifungal evaluations of 2-amino-4-(1-naphthyl)-6-arylpyrimidines. Eur J Med Chem 42:517–520

    Article  CAS  PubMed  Google Scholar 

  • Isa NM, Abdelwahab SI, Mohan S et al (2012) In vitro anti-inflammatory, cytotoxic and antioxidant activities of boesenbergin A, a chalcone isolated from Boesenbergia rotunda (L.) (fingerroot). Braz J Med Biol Res 45:524–530

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Isbrucker RA, Burdock GA (2006) Risk and safety assessment on the consumption of Licorice root (Glycyrrhiza sp.), its extract and powder as a food ingredient, with the emphasis on the pharmacology and toxicology of glycyrrhizin. Regul Toxicol Pharmacol 46:167–192

    Article  CAS  PubMed  Google Scholar 

  • Israf DA, Khaizurin TA, Syahida A et al (2007) Cardamonin inhibits COX and iNOS expression via inhibition of p65NF-κB nuclear translocation and Iκ-B phosphorylation in RAW 264.7 macrophage cells. Mol Immunol 44:673–679

    Article  CAS  PubMed  Google Scholar 

  • Iwamura C, Shinoda K, Yoshimura M et al (2010) Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol Int 59:67–73

    Article  CAS  PubMed  Google Scholar 

  • James S, Aparna JS, Paul AM et al (2017) Cardamonin inhibits colonic neoplasia through modulation of MicroRNA expression. Scientific Reports 7:13945

    Google Scholar 

  • Jamshidzadeh A, Baghban M, Azarpira N et al (2008) Effects of tomato extract on oxidative stress induced toxicity in different organs of rats. Food Chem Toxicol 46:3612–3615

    Article  CAS  PubMed  Google Scholar 

  • Jarosz M, Taraszewska A (2014) Risk factors for gastroesophageal reflux disease: the role of diet. Przegląd Gastroenterol 9:297–301

    Google Scholar 

  • Jez JM, Ferrer JL, Bowman ME et al (2001) Structure and mechanism of chalcone synthase-like polyketide synthases. J Ind Microbiol Biotechnol 27:393–398

    Article  CAS  PubMed  Google Scholar 

  • Jugde H, Nguy D, Moller I (2008) Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple. FEBS J 275:3804–3814

    Article  CAS  PubMed  Google Scholar 

  • Jun R, Zhengang W (1988) Pharmacological research on the effect of licorice. J Tradit Chin Med 8:307–309

    Google Scholar 

  • Jun N, Hong G, Jun K (2007) Synthesis and evaluation of 2′, 4′, 6′-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorg Med Chem 15:2396–2402

    Article  CAS  PubMed  Google Scholar 

  • Jung JI, Chung E, Seon MR et al (2006) Isoliquiritigenin (ISL) inhibits ErbB3 signaling in prostate cancer cells. Biofactors 28:159–168

    Article  CAS  PubMed  Google Scholar 

  • Jung M, Triebel S, Anke T et al (2009) Influence of apple polyphenols on inflammatory gene expression. Mol Nutr Food Res 53:1263–1280

    Article  CAS  PubMed  Google Scholar 

  • Kamei J, Saitoh A, Asano T et al (2005) Pharmacokinetic and pharmacodynamic profiles of the antitussive principles of Glycyrrhizae radix (licorice), a main component of the Kampo preparation Bakumondo-to (Mai-men-dong-tang). Eur J Pharmacol 507:163–168

    Article  CAS  PubMed  Google Scholar 

  • Kanagarajan V, Thanusu J, Gopalakrishnan M (2010) Synthesis and in vitro microbiological evaluation of an array of biolabile 2-morpholino-N-(4, 6-diarylpyrimidin-2-yl) acetamides. Eur J Med Chem 45:1583–1589

    Article  CAS  PubMed  Google Scholar 

  • Kawai Y, Nishikawa T, Shiba Y et al (2008) Macrophage as a target of quercetin glucuronides in human atherosclerotic arteries: implication in the anti-atherosclerotic mechanism of dietary flavonoids. J Biol Chem 283:9424–9434

    Article  CAS  PubMed  Google Scholar 

  • Kayser O, Kiderlen AF (2001) In vitro leishmanicidal activity of naturally occurring chalcones. Phytother Res 15:148–152

    Article  CAS  PubMed  Google Scholar 

  • Khan R, Islam B, Akram M (2009) Antimicrobial activity of five herbal extracts against multi drug resistant (MDR) strains of bacteria and fungus of clinical origin. Molecules 14:586–597

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Khatib S, Nerya O, Musa R et al (2005) Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety. Bioorg Med Chem 13:433–441

    Article  CAS  PubMed  Google Scholar 

  • Kiat TS, Pippen R, Yusof R (2006) Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease. Bioorg Med Chem Lett 16:3337–3340

    Article  CAS  PubMed  Google Scholar 

  • Kim JK, Shin EK, Park JH (2010) Antitumor and antimetastatic effects of licochalcone a in mouse models. J Mol Med (Berl) 88:829–838

    Article  CAS  Google Scholar 

  • Kim MS, Pyun HB, Hwang JK (2013) Effects of orally administered Fingerroot (Boesenbergia pandurata) extract on Oxazolone-induced atopic dermatitis-like skin lesions in hairless mice. Food Sci Biotechnol 22:257–264

    Google Scholar 

  • Kim DU, Chung HC, Kim C et al (2017) Oral intake of Boesenbergia pandurata extract improves skin hydration, gloss, and wrinkling: a randomized, double-blind, and placebo-controlled study. J Cosmet Dermatol 16:512–519

    Article  PubMed  Google Scholar 

  • Kim H-G, Oh H-J, Ko J-H (2019) Lanceoleins A−G, hydroxychalcones, from the flowers of Coreopsis lanceolata and their chemopreventive effects against human colon cancer cells. Bioorg Chem 85:274–281

    Article  CAS  PubMed  Google Scholar 

  • Kirana C, Jones GP, Record IR et al (2007) Anticancer properties of panduratin a isolated from Boesenbergia pandurate (Zingiberaceae). J Nat Med 61:131–137

    Article  CAS  Google Scholar 

  • Kojima T, Akiyama H, Sasai M (2000) Anti-allergic effect of apple polyphenol on patients with atopic dermatitis: A pilot study. Allergol Int 49:69–73

    Article  CAS  Google Scholar 

  • Kolbe L, Immeyer J, Batzer J et al (2006) Anti-inflammatory efficacy of Licochalcone A: correlation of clinical potency and in vitro effects. Arch Dermatol Res 298:23–30

    Article  CAS  PubMed  Google Scholar 

  • Kondo Y, Urisu A, Tokuda R (2001) Identification and characterization of the allergens in the tomato fruit by immunoblotting. Int Arch Allergy Immunol 126:294–299

    Article  CAS  PubMed  Google Scholar 

  • Kostanecki SV, Tambor J (1899) Ueber die sechs isomeren monooxybenzalacetophenone (monooxychalkone). Ber Dtsch Chem Ges 32:1921–1926

    Article  Google Scholar 

  • Kozawa M, Morita N, Baba K et al (1978) Chemical components of the roots of Angelica keiskei Koidzumi. II. The structure of chalcone derivatives. Yakugaku Zasshi 98:210–214

    Article  CAS  PubMed  Google Scholar 

  • Krause M, Galensa R (1992) Determination of naringenin and naringenin-chalconein tomato skins by reversed phase HPLC after solid phase extraction. Z Lebensm Unters Forsch 194:29–32

    Article  CAS  Google Scholar 

  • Kunimasa K, Kuranuki S, Matsuura N, Iwasaki N, Ikeda M, Ito A, Sashida Y, Mimaki Y, Yano M, Sato M, Igarashi Y, Oikawa T (2009) Identification of nobiletin, a polymethoxyflavonoid, as an enhancer of adiponectin secretion. Bioorgan Med Chem Lett 19: 2062–2064

    Google Scholar 

  • Kuramoto K, Suzuki S, Sakaki H et al (2017) Licochalcone A specifically induces cell death in glioma stem cells via mitochondrial dysfunction. FEBS Open Bio 7:835–844

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kwon HS, Park JH, Kim DH et al (2008) Licochalcone A isolated from licorice suppresses lipopolysaccharide-stimulated inflammatory reactions in RAW264.7 cells and endotoxin shock in mice. J Mol Med 86:1287–1295

    Article  CAS  PubMed  Google Scholar 

  • Lazarus SA, Bowen K, Garg ML (2004) Tomato juice and platelet aggregation in type 2 diabetes. JAMA 292:805–806

    Article  CAS  PubMed  Google Scholar 

  • Lea AGH, Arnold GMJ (1978) The phenolics of ciders: bitterness and astringency. J Sci Food Agric 29:478–483

    Article  CAS  Google Scholar 

  • Lee CK, Son SH, Park KK et al (2008) Licochalcone A inhibits the growth of colon carcinoma and attenuates cisplatin-induced toxicity without a loss of chemotherapeutic efficacy in mice. Nordic Pharmacological Society. Basic Clin Pharmacol Toxicol 103:48–54

    Article  CAS  PubMed  Google Scholar 

  • Lee JH, Regmi SC, Kim JA et al (2011) Apple flavonoid phloretin inhibits Escherichia coli O157:H7 biofilm formation and ameliorates colon inflammation in rats. Infect Immun 79:4819–4827

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lee HE, Yang G, Han SH (2018) Anti-obesity potential of Glycyrrhiza uralensis and licochalcone A through induction of adipocyte browning. Biochem Biophys Res Commun 503:2117e2123

    Article  Google Scholar 

  • Li R, Kenyon GL, Cohen FE et al (1995) In vitro antimalarial activity of chalcones and their derivatives. J Med Chem 38:5031–5037

    Article  CAS  PubMed  Google Scholar 

  • Li DQ, Wang Q, Yuan ZF et al (2008) Pharmacokinetics and tissue distribution study of orientin in rat by liquid chromatography. J Pharm Biomed Anal 47:429–434

    Article  PubMed  CAS  Google Scholar 

  • Li G, Simmler C, Chen L et al (2017) Cytochrome P450 inhibition by three licorice species and fourteen licorice constituents. Eur J Pharm Sci 109:182–190

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lin YM, Zhou Y, Flavin MT et al (2002) Chalcones and flavonoids as anti-tuberculosis agents. Bioorg Med Chem 10:2795–2802

    Article  CAS  PubMed  Google Scholar 

  • Lin ST, Tu SH, Yang PS et al (2016) Apple polyphenol phloretin inhibits colorectal cancer cell growth via inhibition of the type 2 glucose transporter and activation of p53-mediated signaling. J Agric Food Chem 64:6826e37

    Article  Google Scholar 

  • Lina BA, Reus AA, Hasselwander O et al (2012) Safety evaluation of Evesse™ EPC, an apple polyphenol extract rich in flavan-3-ols. Food Chem Toxicol 50:2845–2053

    Article  CAS  PubMed  Google Scholar 

  • Liu F, Wei Y, Yang XZ et al (1992) Hypotensive effects of safflower yellow in spontaneously hypertensive rats and influence on plasma renin activity and angiotensin II level. Yao Xue Xue Bao 27:785–787

    CAS  PubMed  Google Scholar 

  • Lu Y, Foo Y (1997) Identification and quantification of major polyphenols in apple pomace. Food Chem 59:187–194

    Article  CAS  Google Scholar 

  • Lu YY, Liang J, Chen SX, Wang BX (2018) Phloridzin alleviate colitis in mice by protecting the intestinal brush border T and improving the expression of sodium glycogen transporter 1. J Funct Foods 45:348–354

    Article  CAS  Google Scholar 

  • Ma L, Wang R, Nan Y, Li W, Wang Q, Jin F (2016) Phloretin exhibits an anticancer effect and enhances the anticancer ability of cisplatin on non-small cell lung cancer cell lines by regulating expression of apoptotic pathways and matrix metalloproteinases. Int J Oncol 48:843-853

    Google Scholar 

  • Ma Y, Yu T, Zhang Y et al (2018) The protective effect of cardamonin on the factors involved in delayed cerebral vasospasm in a rat model of subarachnoid haemorrhage. Int J Clin Exp Pathol 11:5955–5961

    CAS  PubMed  PubMed Central  Google Scholar 

  • Mahmood AA, Mariod AA, Abdelwahab SI et al (2010) Potential activity of ethanolic extract of Boesenbergia rotunda (L.) rhizomes extract in accelerating wound healing in rats. J Med Plant Res 4:1570–1576

    Google Scholar 

  • Malathi P, Crane RK (1969) Phlorizin hydrolase: a beta-glucosidase of hamster intestinal brush border membrane. Biochim Biophys Acta 173:245–256

    Article  CAS  PubMed  Google Scholar 

  • Mangas JJ, SuaÂrez B, Picinelli A et al (1997) Differentiation of phenolic profile of apple juices prepared according to two membrane techniques. J Agric Food Chem 45:4777–4784

    Article  CAS  Google Scholar 

  • Mark DH, Larry AH (1993) Variation in concentrations of phloridzin and phloretin in apple foliage. Phytochem 34:1251–1254

    Google Scholar 

  • Marliyana SD, Rukayadi Y, Ismail IS (2015) Inhibitory properties of panduratin A and 4-hydroxypanduratin A isolated Kaempferia pandurata against some pathogenic bacteria. Curr Top Toxicol 11:23–28

    Google Scholar 

  • Marliyana SD, Mujahidin D, Syah YM (2017) Time-kill assay of 4-Hydroxypanduratin a isolated from Kaempferia Pandurata against foodborne pathogens. Mol Ther 12:166–173

    CAS  Google Scholar 

  • Massey LK, Roman-Smith H, Sutton RAL (1993) Effect of dietary oxalate and calcium on urinary oxalate and risk of formation of calcium oxalate kidney stones. J Am Diet Assoc 93:901–906

    Article  CAS  PubMed  Google Scholar 

  • Mathiesen L, Malterud KE, Sund RB (1996) Uncoupling of respiration and inhibition of ATP synthesis in mitochondria by C-methylated flavonoids from Myrica gale L. Eur J Pharm Sci 4:373–379

    Article  CAS  Google Scholar 

  • Mayr H, Kempf B, Ofial AR (2003) π-Nucleophilicit in carbon-carbon bond-forming reactions. Acc Chem Res 36:66–77

    Article  CAS  PubMed  Google Scholar 

  • McRae KB, Lidster PD, de Marco AC et al (1990) Comparison of the polyphenol profiles of apple fruit cultivars by correspondence analysis. J Sci Food Agric 50:329–342

    Article  CAS  Google Scholar 

  • Mendes V, Monteiro RR, Pestana D et al (2008) Xanthohumol influences preadipocyte differentiation: implication of antiproliferative and apoptotic effects. J Agric Food Chem 56:11631–11637

    Article  CAS  PubMed  Google Scholar 

  • Messier C, Grenier D (2011) Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. Mycoses 54:e801–e806

    Article  CAS  PubMed  Google Scholar 

  • Mintz-Oron S, Mandel T, Rogachev I et al (2008) Gene expression and metabolism in tomato fruit surface tissues. Plant Physiol 147:823–851

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mishra N, Arora P, Kumar B et al (2008) Synthesis of novel substituted 1,3-diaryl propenone derivatives and their anti-malarial activity in vitro. Eur J Med Chem 43:1530–1535

    Article  CAS  PubMed  Google Scholar 

  • Mishra LC, Bhattacharya A, Bhasin VK (2009) Phytochemical licochalcone A enhances antimalarial activity of artemisinin in vitro. Acta Trop 109:194–198

    Article  CAS  PubMed  Google Scholar 

  • Moco S, Bino RJ, Vorst O et al (2006) A liquid chromatography – mass spectrometry-based metabolome database for tomato. Plant Physiol 141:1205–1218

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Modzelewska A, Pettit C, Achanta G et al (2006) Anti-cancer activities of novel chalcone and bis-chalcone derivatives. Bioorg Med Chem 14:3491–3495

    Article  CAS  PubMed  Google Scholar 

  • Khalifa MMA, Bakr AG, Osman AT (2017) Protective effects of phloridzin against methotrexate-induced liver toxicity in rats. Biomedicine & Pharmacotherapy 95: 529–535

    Google Scholar 

  • Monge P, Solheim E, Scheline RR (1984) Metabolism in the rat: phloretin. Xenobiotica 14:917–924

    Article  CAS  PubMed  Google Scholar 

  • Muir SR, Collins GJ, Robinson S et al (2001) Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols. Nat Biotechnol 19:470–474

    Article  CAS  PubMed  Google Scholar 

  • Nabekura T, Hiroi T, Kawasaki T et al (2015) Effects of natural nuclear factor-kappa B inhibitors on anticancer drug efflux transporter human P-glycoprotein. Biomed Pharmacother 70:140–145

    Article  CAS  PubMed  Google Scholar 

  • Nadelmann L, Tjørnelunda J, Christensenb E et al (1997) High-performance liquid chromatographic determination of licochalcone A and its metabolites in biological fluids. J Chromatogr B 695:389–400

    Article  CAS  Google Scholar 

  • Nakagawa-Goto K, Bastow KF, Wu JH et al (2005) Total synthesis and bioactivity of unique flavone desmosdumotin B and its analogs. Bioorg Med Chem Lett 15:3016–3019

    Article  CAS  PubMed  Google Scholar 

  • Nakahara K, Trakoontivakorn G (1999) Antioxidative and antimutagenic properties of some local agricultural products in Thailand. In: Paper presented a highlight of collaborative research activities between Thai research organizations and JIRCAS, Bangkok, 3 March 1999, pp 141–143

    Google Scholar 

  • Nakahara K, Trakoontivakorn G, Alzoreky NS et al (2002) Antimutagenicity of some edible Thai plants, and a bioactive carbazole alkaloid, mahanine, isolated from Micromelum minutum. J Agric Food Chem 50:4796–4802

    Article  CAS  PubMed  Google Scholar 

  • Nakamura Y, Watanabe S, Miyake N et al (2003) Dihydrochalcones: evaluation as novel radical scavenging antioxidants. J Agric Food Chem 51:3309–3312

    Article  CAS  PubMed  Google Scholar 

  • Nakata K, Taniguchi M, Baba K (1999) Three chalcones from Angelica keiskei. Nat Med 53:329–332

    CAS  Google Scholar 

  • Nelson JA, Falk RE (1993) The efficacy of phloridzin and phloretin on tumor cell growth. Anticancer Res 13:2287e92

    Google Scholar 

  • Nguyen MT, Awale S, Tezuka Y et al (2004) Xanthine oxidase inhibitory activity of Vietnamese medicinal plants. Biol Pharm Bull 27:1414–1421

    Article  CAS  PubMed  Google Scholar 

  • Nielsen SF, Chen M, Theander TG et al (1995) Synthesis of antiparasitic licorice chalcones. Bioorg Med Chem Lett 5:449–452

    Article  Google Scholar 

  • Nielsen SF, Boesen T, Larsen M et al (2004) Antibacterial chalcones-bioisosteric replacement of the 4′-hydroxy group. Bioorg Med Chem 12:3047–3054

    Article  CAS  PubMed  Google Scholar 

  • Nishigaki I, Rajkapoor B, Rajendran P et al (2010) Effect of fresh apple extract on glycated protein/iron chelate-induced toxicity in human umbilical vein endothelial cells in vitro. Nat Prod Res 24:599–609

    Article  CAS  PubMed  Google Scholar 

  • Nomura T, Fukai T, Akiyama T (2002) Chemistry of phenolic compounds of licorice (Glycyrrhiza species) and their estrogenic and cytotoxic activities. Pure Appl Chem 74:1199–1206

    Article  CAS  Google Scholar 

  • Nurrachma MY, Fadliyah H, Meiyanto E (2018) Fingerroot (Boesenbergia pandurate): a prospective anticancer therapy. Indones J Can Chemoprevention 9:102–109

    Article  Google Scholar 

  • Obara H, Onodera J (1979) Structure of carthamin. Chem Lett 8:201–204

    Article  Google Scholar 

  • Olson G, Betton D, Robinson K (2000) Concordance of toxicity of pharmaceuticals in humans and in animals. Regul Toxicol Pharmacol 32:56–67

    Article  CAS  PubMed  Google Scholar 

  • Olthof MR, Hollman PCH, Katan MB (2001) Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr 131:66–71

    Article  CAS  PubMed  Google Scholar 

  • Omar HR, Komarova I, El-Ghonemi M (2012) Licorice abuse: time to send a warning message. Ther Adv Endocrinol Metab 3:125–138

    Article  PubMed  PubMed Central  Google Scholar 

  • Ongwisespaiboon O, Jiraungkoorskul W (2017) Fingerroot, Boesenbergia rotunda and its aphrodisiac activity. Pharmacogn Rev 11:27–30

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Pandey DK, Shekelle R, Selwyn BJ et al (1995) Dietary vitamin C and beta-carotene and risk of death in middle-aged men. The Western Electric Study. Am J Epidemiol 142:1269–1278

    Article  CAS  PubMed  Google Scholar 

  • Park HG, Bak EJ, Woo GH et al (2012) Licochalcone E has an antidiabetic effect. J Nutr Biochem 23:759–767

    Article  CAS  PubMed  Google Scholar 

  • Park SY, Kim EJ, Choi HJ et al (2014) Anti-carcinogenic effects of non-polar components containing licochalcone A in roasted licorice root. Nutr Res Pract 8:257–266

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Patil CB, Mahajan SK, Katti SA (2009) Chalcone-A versatile molecule. J Pharm Sci Res 1:11–22

    CAS  Google Scholar 

  • Peng F, Tang H, Liu P, Shen J (2017) Isoliquiritigenin modulated miR-374a/PTEN/Akt axis to suppress breast cancer tumorigenesis and metastasis. Sci Rep 7:9022

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Peschel W, Sanchez-Rabaneda F, Diekmann W et al (2006) An industrial approach in the search of natural antioxidants from vegetable and fruit wastes. Food Chem 97:137–150

    Article  CAS  Google Scholar 

  • Phillips SL, Polzin DJ (1998) Clinical disorders of potassium homeostasis. Hyperkalemia and hypokalemia. Vet Clin North Am 28:545–564

    Article  CAS  Google Scholar 

  • Priyadharsini P, Muthukumar T (2016) Interactions between arbuscular mycorrhizal fungi and potassium-solubilizing microorganisms on agricultural productivity. In: Meena VS, Maurya BR, Prakash Verma J et al (eds) Potassium solubilizing microorganisms for sustainable agriculture. Springer, New York, pp 111–125

    Chapter  Google Scholar 

  • Qiao H, Zhang X, Wang T et al (2014) Pharmacokinetics, biodistribution and bioavailability of isoliquiritigenin after intravenous and oral administration. Pharm Biol 52:228–236

    Article  CAS  PubMed  Google Scholar 

  • Quynh LL, Yvonne L, Stephan S et al (2006) Design of tomato fruits with reduced allergenicity by dsRNAi-mediated inhibition of NSLTP (Lyc e 3) expression. Plant Biotechnol J 4:231–242

    Article  CAS  Google Scholar 

  • Ramirez-Ambrosi M, Abad-Garcia B, Viloria-Bernal M (2013) A new ultrahigh performance liquid chromatography with diode array detection coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry analytical strategy for fast analysis and improved characterization of phenolic compounds in apple products. J Chromatogr A 1316:78–91

    Article  CAS  PubMed  Google Scholar 

  • Reagan-Shaw S, Eggert D, Mukhtar H (2010) Antiproliferative effects of apple peel extract against cancer cells. Nutr Cancer 62:517e24

    Article  Google Scholar 

  • Rechner AR, Spencer JPE, Kuhnle G et al (2001) Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic Biol Med 30:1213–1222

    Article  CAS  PubMed  Google Scholar 

  • Reddy VM, Reddy KR (2010) Synthesis and biological evaluation of some novel-3-(5-substituted benzimidazole-2-yl)-5-aryl isoxazolines. Chin Chem Lett 21:1145–1148

    Article  CAS  Google Scholar 

  • Reddy MVB, Su CR, Chiou WF et al (2008) Design, synthesis, and biological evaluation of mannich bases of heterocyclic chalcone analogs as cytotoxic agents. Bioorg Med Chem 16:7358–7370

    Article  CAS  PubMed  Google Scholar 

  • Ren G, Sun A, Deng C et al (2015) The anti-inflammatory effect and potential mechanism of cardamonin in DSS-induced colitis. Am J Physiol Gastrointest Liver Physiol 309:G517–G527

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ren Y, Yan Y, Tan Y et al (2018) Isoliquiritigenin inhibits mouse S180 tumors with a new mechanism that regulates autophagy by GSK-3β/TNF-α pathway. Eur J Pharmacol 838:11–22

    Article  CAS  Google Scholar 

  • Rezk BM, Haenen GR, van der Vijgh WJ (2002) The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem Biophys Res Commun 295:9–13

    Article  CAS  PubMed  Google Scholar 

  • Rodriguez MJ, Ortiz M, VaÂzquez A et al (1982) Competitive kinetics in the inhibition of sugar intestinal transport by phlorizin in vivo. Rev Esp Fisiol 38:397–402

    CAS  PubMed  Google Scholar 

  • Rondini L, Peyrat-Maillard MN, Marsset-Baglieri A et al (2002) Sulfated ferulic acid is the main in vivo metabolite found after short-term ingestion of free ferulic acid in rats. J Agric Food Chem 50:3037–3041

    Article  CAS  PubMed  Google Scholar 

  • Ross JA, Kasum CM (2002) Dietary flavonoids: bioavailability, metabolic effects, and safety. Annu Rev Nutr 22:19–34

    Article  CAS  PubMed  Google Scholar 

  • Sahu NK, Balbhadra SS, Choudhary J et al (2012) Exploring pharmacological significance of chalcone scaffold: a review. Curr Med Chem 19:209–225

    Article  CAS  PubMed  Google Scholar 

  • Salama SM, Ibrahim IAA, Shahzad N et al (2018) Hepatoprotectivity of Panduratin A against liver damage: in vivo demonstration with a rat model of cirrhosis induced by thioacetamide. J Pathol Microbiol Immunol 126:710–721

    CAS  Google Scholar 

  • Sandra W, Daniel K, Kay F et al (2003) Molecular characterization and allergenic activity of Lyc e 2 (b-fructofuranosidase), a glycosylated allergen of tomato. Eur J Biochem 270:1327–1337

    Article  CAS  Google Scholar 

  • Scalbert A, Williamson G (2000) Dietary intake and bioavailability of polyphenols. J Nutr 130:2073S–2085S

    Article  CAS  PubMed  Google Scholar 

  • Schiavano GF, De Santi M, Brandi G et al (2015) Inhibition of breast cancer cell proliferation and in vitro tumorigenesis by a new red apple cultivar. PLoS One 10:e0135840

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Schieber A, Keller P, Carle R (2001) Determination of phenolic acids and flavonoids of apple and pear by high-performance liquid chromatography. J Chromatogr A 910:265–273

    Article  CAS  PubMed  Google Scholar 

  • Seleem D, Benso B, Noguti J et al (2016) In vitro and in vivo antifungal activity of Lichochalcone-A against Candida albicans biofilms. PLoS One 11:e0157188

    Google Scholar 

  • Selvam TP, Karthick V, Kumar PV et al (2013) Antiepileptic activity of novel 2-(substituted benzylidene)-7-(4-fluorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one derivatives. Lett Drug Des Discovery 10:204–211

    CAS  Google Scholar 

  • Sesso H, Gaziano JM, Liu S et al (2003) Flavonoid intake and risk of cardiovascular disease in women. Am J Clin Nutr 77:1400–1408

    Article  CAS  PubMed  Google Scholar 

  • Shan B, Cai YZ, Brooks JD (2007) The in vitro antibacterial activity of dietary spice and medicinal herb extracts. Int J Food Microbiol 117:112–119

    Article  CAS  PubMed  Google Scholar 

  • Sharma A, Chakravarti B, Gupt MP (2010) Synthesis and anti-breast cancer activity of biphenyl based chalcones. Bioorg Med Chem 18:4711–4720

    Article  CAS  PubMed  Google Scholar 

  • Shindo K, Kato M, Kinoshita A (2006) Analysis of antioxidantactivities contained in the Boesenbergia pandurata Schult. Rhizome. Biosci Biotechnol Biochem 70:2281–2284

    Article  CAS  PubMed  Google Scholar 

  • Shoji T, Akazome Y, Kanda T et al (2004) The toxicology and safety of apple polyphenol extract. Food Chem Toxicol 42:959–967

    Article  CAS  PubMed  Google Scholar 

  • Si H, Xu C, Zhang J et al (2018) Licochalcone A: an effective and low-toxicity compound against toxoplasma T gondii in vitro and in vivo. IJP Drugs Drug Resist 8:238–245

    Article  Google Scholar 

  • Siener R, Seidler A, Voss S et al (2016) The oxalate content of fruit and vegetable juices, nectars and drinks. J Food Compos Anal 45:108–112

    Article  CAS  Google Scholar 

  • Silaste ML, Alfthan G, Aro A et al (2007) Tomato juice decreases LDL cholesterol levels and increases LDL resistance to oxidation. Br J Nutr 98:1251–1258

    Article  CAS  PubMed  Google Scholar 

  • Simmler C, Hajirahimkhan A, Lankin DC et al (2013) Dynamic residual complexity of the isoliquiritigenin-liquiritigenin interconversion during bioassay. J Agric Food Chem 61:2146–2157

    Article  CAS  PubMed  Google Scholar 

  • Simonetti P, Gardana C, Riso P (2005) Glycosylated flavonoids from tomato puree are bioavailable in humans. Nutr Res 25:717–726

    Article  CAS  Google Scholar 

  • Slimestad R, Verheul MJ (2005) Content of chalconaringenin and chlorogenic acid in cherry tomatoes is strongly reduced during postharvest ripening. J Agric Food Chem 53:7251–7256

    Article  CAS  PubMed  Google Scholar 

  • Slimestad R, Fossen T, Verheul MJ (2008) The flavonoids of tomatoes. J Agric Food Chem 56:2436–2441

    Article  CAS  PubMed  Google Scholar 

  • Spanos GA, Wrolstad RE (1992) Phenolics of apple, pear, and white grape juices and their changes with processing and storages A review. J Agric Food Chem 40:1478–1487

    Article  CAS  Google Scholar 

  • Stangl V, Lorenz M, Ludwig A et al (2005) The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. J Nutr 135:172–178

    Article  CAS  PubMed  Google Scholar 

  • Sun J, Liu RH (2008) Apple phytochemical extracts inhibit proliferation of estrogen-dependent and estrogen-independent human breast cancer cells through cell cycle modulation. J Agric Food Chem 56:11661e7

    Article  Google Scholar 

  • Sung MW, Li PCH (2004) Chemical analysis of raw, dry-roasted, and honey-roasted licorice by capillary electrophoresis. Electrophoresis 25:3434–3440

    Article  CAS  PubMed  Google Scholar 

  • Tan BC, Tan SK, Wong SM et al (2015) Distribution of flavonoids and Cyclohexenyl Chalcone derivatives in conventional propagated and in vitro-derived field-grown Boesenbergia rotunda (L.) Mansf. Evid Based Complement Alternat Med 2015:451870

    Article  PubMed  PubMed Central  Google Scholar 

  • Tangkanakul P, Trakoontivakorn G, Saengprakai J (2011) Antioxidant capacity and Antimutagenicity of thermal processed Thai foods. Jpn Agric Res Q 45:211–218

    Article  Google Scholar 

  • Tewtrakul S, Subhadhirasakul S, Puripattanavong J et al (2003) HIV-1 protease inhibitory substances from the rhizomes of Boesenbergia pandurate Holtt. Songklanakarin J Sci Technol 25:503–508

    CAS  Google Scholar 

  • Thongson C, Davidson PM, Mahakarnchanakul W (2004) Antimicrobial activity of ultrasound-assisted solvent-extracted spices. Lett Appl Microbiol 39:401–406

    Article  CAS  PubMed  Google Scholar 

  • Tomás-Barberán FA, Clifford MI (2000) Flavanones, chalcones and dihydrochalcones – nature, occurrence and dietary burden. J Sci Food Agric 80:1073–1080

    Article  Google Scholar 

  • Townsend MK, Devore EE, Resnick NM et al (2013) Acidic fruit intake in relation to incidence and progression of urinary incontinence. Int Urogynecol J 24:605–612

    Article  PubMed  Google Scholar 

  • Trakoontivakorn G, Nakahara K, Shinmoto H et al (2001) Structural analysis of a novel Antimutagenic compound, 4-Hydroxypanduratin A, and the Antimutagenic activity of flavonoids in a Thai spice, Fingerroot (Boesenbergia pandurate Schult.) against mutagenic heterocyclic amines. J Agric Food Chem 49:3046–3050

    Article  CAS  PubMed  Google Scholar 

  • Tsukiyama RI, Katsura H, Tokuriki N et al (2002) Antibacterial activity of licochalcone A against spore-forming bacteria. Antimicrob Agents Chemother 6:1226e1230

    Google Scholar 

  • Utsintong M, Massarotti A, Caldarelli A et al (2013) Parallel synthesis of “click” chalcones as antitubulin agents. Med Chem 9:510–516

    Article  CAS  PubMed  Google Scholar 

  • Vallverdú-Queralt A, Jáuregui O, Di Lecce G et al (2011) Screening of the polyphenol content of tomato-based products through accurate-mass spectrometry (HPLC–ESI-QTOF). Food Chem 129:877–883

    Article  PubMed  CAS  Google Scholar 

  • Velliquette RA, Grann K, Missler SR et al (2015) Identification of a botanical inhibitor of intestinal diacylglyceride acyltransferase 1 activity via in vitro screening and a parallel, randomized, blinded, placebo-controlled clinical trial. Nutr Metab 12:27

    Article  CAS  Google Scholar 

  • Verhoeyen ME, Bovy A, Collins G et al (2002) Increasing antioxidant levels in tomatoes through modification of the flavonoid biosynthetic pathway. J Exp Bot 53:2099–2106

    Article  CAS  PubMed  Google Scholar 

  • Versari A, Biesenbruch S, Barbanti D et al (1997) Adulteration of fruit juices: Dihydrochalcones as quality markers for apple juice identification. Lebensm Wiss Technol 30:585–589

    Article  CAS  Google Scholar 

  • Vikram A, Jayaprakasha GK, Jesudhasan PR (2010) Suppression of bacterial cell-cell signalling, biofilm formation and type III secretion system by citrus flavonoids. J Appl Microbiol 109:515–527

    Article  CAS  PubMed  Google Scholar 

  • Vilkhu K, Mawson R, Simons L (2008) Applications and opportunities for ultrasound assisted extraction in the food industry – a review. Innov Food Sci Emerg Technol 9:161–169

    Article  CAS  Google Scholar 

  • Vineetha VP, Girija S, Soumya RS et al (2014) Polyphenol-rich apple (Malus domestica L.) peel extract attenuates arsenic trioxide induced cardiotoxicity in H9c2 cells via its antioxidant activity. Food Funct 5:502–511

    Article  CAS  PubMed  Google Scholar 

  • Vogel S, Ohmayer S, Brunner G et al (2008) Natural and non-natural prenylated chalcones: synthesis, cytotoxicity and anti-oxidative activity. Bioorg Med Chem 16:4286–4293

    Article  CAS  PubMed  Google Scholar 

  • Walker BR, Connacher AA, Webb DJ et al (1992) Glucocorticoids and blood pressure: a role for the cortisol/cortisone shuttle in the control of vascular tone in man. Clin Sci 83:171–178

    Article  CAS  Google Scholar 

  • Walker BR, Sang KS, Williams BC et al (1994) Direct and indirect effects of carbenoxolone on responses to glucocorticoids and noradrenaline in rat aorta. J Hypertens 12:33–39

    Article  CAS  PubMed  Google Scholar 

  • Wang JH, Luo JY, Dong L et al (2004) Epidemiology of gastroesophageal reflux disease: a general population-based study in Xi’an of Northwest China. World J Gastroenterol 10:1647–1651

    Article  PubMed  PubMed Central  Google Scholar 

  • Wang KL, Hsia SM, Chan CJ et al (2013) Inhibitory effects of isoliquiritigenin on the migration and invasion of human breast cancer cells. Expert Opin Ther Targets 17:337–349

    Article  PubMed  CAS  Google Scholar 

  • Wei X, Liu H, Sun X et al (2005) Hydroxysafflor yellow A protects rat brains against ischemia-reperfusion injury by antioxidant action. Neurosci Lett 368:58–62

    Article  CAS  Google Scholar 

  • Welter S (2014) Impact of biotic factors on the allergenic potential of tomato and identification of cyclophilin as a new putative tomato allergen. Doctoral Thesis

    Google Scholar 

  • Westphal S, Kempf W, Foetisch K et al (2004) Tomato profilin Lyc e 1: IgE cross-reactivity and allergenic potency. Allergy 59:526–532

    Article  CAS  PubMed  Google Scholar 

  • Williams AH (1964) Dihydrochalcones: their occurrence and use as indicators in chemical plant taxonomy. Nature 202:824–825

    Article  CAS  Google Scholar 

  • Woo SW, Rhim DB, Kim C et al (2015) Effect of standardized Boesenbergia pandurate extract and its active compound Panduratin a on skin hydration and barrier function in human epidermal keratinocytes. Prev Nutr Food Sci 20:15–21

    Article  PubMed  PubMed Central  Google Scholar 

  • Wu JH, Wang XH, Yi YH et al (2003) Anti-AIDS agents 54, A potent anti-HIV chalcone and flavonoids from genus Desmos. Bioorg Med Chem Lett 13:1813–1815

    Article  CAS  PubMed  Google Scholar 

  • Wu CH, Ho YS, Tsai CY et al (2009) In vitro and in vivo study of phloretin-induced apoptosis in human liver cancer cells involving inhibition of type II glucose transporter. Int J Cancer 124:2210e9

    Article  Google Scholar 

  • Wu KH, Ho CT, Chen ZF (2018) The apple polyphenol phloretin inhibits breast cancer cell migration and proliferation via inhibition of signals by type 2 glucose transporter. J Food Drug Anal 26:221–231

    Article  CAS  PubMed  Google Scholar 

  • Yamakoshi J, Sato T, Matsumura T et al (2004) Safety evaluation of flavonoids-containing tomato skin extract. Pharmacometrics 67:313–321

    Google Scholar 

  • Yamamoto T, Yoshimura M, Yamaguchi F et al (2004) Anti-allergic activity of naringenin chalcone from a tomato skin extract. Biosci Biotechnol Biochem 68:1706–1711

    Article  CAS  PubMed  Google Scholar 

  • Yang CS, Landau JM, Huang MT et al (2001) Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 21:381–406

    Article  CAS  PubMed  Google Scholar 

  • Yang KC, Tsai CY, Wang YJ et al (2009) Apple polyphenol phloretin potentiates the anticancer actions of paclitaxel through induction of apoptosis in human Hep G2 cells. Mol Carcinog 48:420e31

    Article  Google Scholar 

  • Yang R, Yuan BC, Ma YS et al (2017) The anti-inflammatory activity of licorice, a widely used Chinese herb. Pharm Biol 55:5–18

    Article  CAS  PubMed  Google Scholar 

  • Yanti RY, Lee KH et al (2009) Activity of panduratin A isolated from Kaempferia pandurata Roxb. against multi-species oral biofilms in vitro. J Oral Sci 51:87–95

    Article  CAS  PubMed  Google Scholar 

  • Yao H, Liao ZX, Wu Q, Lei GQ, Liu ZJ, Chen DF, Chen JK, Zhou TS (2006) Antioxidative flavanone glycosides from the branches and leaves of Viscum coloratum. Chem Pharm Bull 54:133–135

    Article  CAS  Google Scholar 

  • Ye L, Gho WM, Chan FL et al (2009) Dietary administration of the licorice flavonoid isoliquiritigenin deters the growth of MCF-7 cells overexpressing aromatase. Int J Cancer 124:1028–1036

    Article  CAS  PubMed  Google Scholar 

  • Yi W, Wetzstein HY (2011) Effects of drying and extraction conditions on the biochemical activity of selected herbs. HortScience 46:70–73

    Article  CAS  Google Scholar 

  • Yoon H, Liu RH (2007) Effect of selected phytochemicals and apple extracts on NF-kappa B activation in human breast cancer MCF-7 cells. J Agric Food Chem 55:3167e73

    Article  CAS  Google Scholar 

  • Yoshimura M, Enomoto T, Dake Y et al (2007) An evaluation of the clinical efficacy of tomato extract for perennial allergic rhinitis. Allergol Int 56:225–230

    Article  CAS  PubMed  Google Scholar 

  • Yoshimura M, Sano A, Kamei JI et al (2009) Identification and quantification of metabolites of orally administered naringenin chalcone in rats. J Agric Food Chem 57:6432–6437

    Article  CAS  PubMed  Google Scholar 

  • Yuan X, Li T, Xiao E et al (2014) Licochalcone B inhibits growth of bladder cancer cells by arresting cell cycle progression and inducing apoptosis. Food Chem Toxicol 65:242–251

    Article  CAS  PubMed  Google Scholar 

  • Yuvaraj AR, Rahman ML, Yusoff MM et al (2016) Photoinhibition effect from strong electron withdrawing nitro group in N-[(E)-(4-bromophenyl)methylidene]-4-nitroaniline. Chemistry of. Adv Mater 1:1–5

    Google Scholar 

  • Zadeh JB, Kor ZM, Goftar MK (2013) Licorice (Glycyrrhiza glabra Linn) as a valuable medicinal plant. Int J Adv Biol Biomed Res 1:1281–1288

    CAS  Google Scholar 

  • Zenger K, Dutta S, Wolff H et al (2015) In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells. Toxicology 336:26–33

    Article  CAS  PubMed  Google Scholar 

  • Zhai L, Blom J, Chen M et al (1995) The antileishmanial agent licochalcone A interferes with the function of parasite mitochondria. Antimicrob Agents Chemother 39:2742–2748

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhang Q, Ye M (2009) Chemical analysis of the Chinese herbal medicine gan-cao (licorice). J Chromatogr A 1216:1954–1969

    Article  CAS  PubMed  Google Scholar 

  • Zhang CX, Ho SC, Chen YM et al (2009a) Greater vegetable and fruit intake is associated with a lower risk of breast cancer among Chinese women. Int J Cancer 125:181–188

    Article  CAS  PubMed  Google Scholar 

  • Zhang X, Liu JP, Qiao H et al (2009b) Determination and pharmacokinetics of Isoliquiritigenin in rat plasma by reverse phase high-performance liquid chromatography after intravenous administration. Chromatographia 70:423–430

    Article  CAS  Google Scholar 

  • Zhang X, Zhu P, Zhang X et al (2013) Natural antioxidant-isoliquiritigenin ameliorates contractile dysfunction of hypoxic cardiomyocytes via AMPK signaling pathway. Mediat Inflamm 2013:390890

    Article  Google Scholar 

  • Zhang X, Qiao H, Zhang T et al (2014a) Enhancement of gastrointestinal absorption of isoliquiritigenin by nanostructured lipid carrier. Adv Powder Technol 25:1060–1068

    Article  CAS  Google Scholar 

  • Zhang ZH, Yu LJ, Hui XC et al (2014b) Hydroxy-safflor yellow A attenuates Abeta(1)(−)(4)(2)-induced inflammation by modulating the JAK2/STAT3/NF-kappa B pathway. Brain Res 1563:72–80

    Article  CAS  PubMed  Google Scholar 

  • Zhou TZ, Deng XM, Qiu JZ (2012) Antimicrobial activity of Licochalcone E against Staphylococcus aureus and its impacts on the production of staphylococcal alpha-toxin. J Microbiol Biotechnol 22:800–805

    Article  CAS  PubMed  Google Scholar 

  • Zhou M, Liu L, Wang W (2015) Role of licochalcone C in cardioprotection against ischemia/reperfusion injury of isolated rat heart via antioxidant, anti-inflammatory, and anti-apoptotic activities. Life Sci 132:27–33

    Article  CAS  PubMed  Google Scholar 

  • Zukiewicz-Sobczak WA, Wroblewska P, Adamczuk P et al (2013) Causes, symptoms and prevention of food allergy. Adv Dermatol Allergol/Postȩpy Dermatologii i Alergologii 30:113–116

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Siau Hui Mah .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2021 Springer Nature Singapore Pte Ltd.

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Mah, S.H. (2021). Chalcones in Diets. In: Xiao, J., Sarker, S.D., Asakawa, Y. (eds) Handbook of Dietary Phytochemicals. Springer, Singapore. https://doi.org/10.1007/978-981-15-4148-3_10

Download citation

Publish with us

Policies and ethics