Cardamonin, as shown by the increasing number of publications, has received growing attention from the scientific community due to the expectations toward its benefits to human health. In this study, research on cardamonin is reviewed, including its natural sources, health promoting aspects, and analytical methods for its determination. Therefore, this article hopes to aid current and future researchers on the search for reliable answers concerning cardamonin's value in medicine.
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References
1.
YadavVR, PrasadS, SungB, AggarwalBB: The role of chalcones in suppression of NF-κB-mediated inflammation and cancer. Int Immunopharmacol, 2011; 11:295–309.
2.
SahuNK, BalbhadraSS, ChoudharyJ, KohliDV: Exploring pharmacological significance of chalcone scaffold: a review. Curr Med Chem, 2012; 19:209–225.
3.
NiL, MengCQ, SikorskiJA: Recent advances in therapeutic chalcones. Expert Opin Ther Pat, 2004; 14:1669–1691.
4.
OrlikovaB, TasdemirD, GolaisF, DicatoM, DiederichM: Dietary chalcones with chemopreventive and chemotherapeutic potential. Genes Nutr, 2011; 6:125–147.
5.
SungB, PrasadS, YadavVR, AggarwalBB: Cancer cell signaling pathways targeted by spice-derived nutraceuticals. Nutr Cancer, 2011; 64:173–197.
6.
BoyleP, DiehmC, RobertsonC: Meta-analysis of clinical trials of Cyclo 3 Fort in the treatment of chronic venous insufficiency. Int Angiol, 2003; 22:250–262.
7.
MagalhãesPJ, CarvalhoDO, CruzJM, GuidoLF, BarrosAA: Fundamentals and health benefits of xanthohumol, a natural product derived from hops and beer. Nat Prod Commun, 2009; 4:591–610.
8.
GerhauserC, AltA, HeissE, et al.: Cancer chemopreventive activity of Xanthohumol, a natural product derived from hop. Mol Cancer Ther, 2002; 1:959–969.
9.
StevensJF, PageJE: Xanthohumol and related prenylflavonoids from hops and beer: to your good health!. Phytochemistry, 2004; 65:1317–1330.
10.
MoreiraMM, CarvalhoAM, ValenteIM, et al.: Novel application of square-wave adsorptive-stripping voltammetry for the determination of xanthohumol in spent hops. J Agric Food Chem, 2011; 59:7654–7658.
11.
XiaoX-Y, HaoM, YangX-Y, et al.: Licochalcone A inhibits growth of gastric cancer cells by arresting cell cycle progression and inducing apoptosis. Cancer Lett, 2011; 302:69–75.
12.
ZiX, SimoneauAR: Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice. Cancer Res, 2005; 65:3479–3486.
13.
TabataK, MotaniK, TakayanagiN, et al.: Xanthoangelol, a major chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma and leukemia cells. Biol Pharm Bull, 2005; 28:1404–1407.
14.
GuidaA, LhoutyMH, TichitD, FiguerasF, GenesteP: Hydrotalcites as base catalysts. Kinetics of Claisen-Schmidt condensation, intramolecular condensation of acetonylacetone and synthesis of chalcone. Appl Catal A Gen, 1997; 164:251–264.
15.
RomanelliG, PasqualeG, SathicqÁ, ThomasH, AutinoJ, VázquezP: Synthesis of chalcones catalyzed by aminopropylated silica sol–gel under solvent-free conditions. J Mol Catal A Chem, 2011; 340:24–32.
16.
Cechinel-FilhoV, VazZR, ZuninoL, CalixtoJB, YunesRA: Synthesis of xanthoxyline derivatives with antinociceptive and antioedematogenic activities. Eur J Med Chem, 1996; 31:833–839.
17.
EddarirS, CotelleN, BakkourY, RolandoC: An efficient synthesis of chalcones based on the Suzuki reaction. Tetrahedron Lett, 2003; 44:5359–5363.
18.
VieiraLCC, PaixãoMW, CorrêaAG: Green synthesis of novel chalcone and coumarin derivatives via Suzuki coupling reaction. Tetrahedron Lett, 2012; 53:2715–2718.
19.
CasiraghiG, CasnatiG, DradiE, MessoriR, SartoriG: A general synthesis of 2′-hydroxychalcones from bromomagnesium phenoxides and cinnamic aldehydes. Tetrahedron, 1979; 35:2061–2065.
20.
SchröderJ, RaiberS, BergerT, et al.: Plant polyketide synthases: a chalcone synthase-type enzyme which performs a condensation reaction with methylmalonyl-CoA in the biosynthesis of C-methylated chalcones. Biochemistry (Mosc), 1998; 37:8417–8425.
21.
AustinMB, NoelJP: The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep, 2003; 20:79–110.
22.
KrishnaBM, ChagantyRB: Cardamonin and alpinetin from the seeds of Alpinia speciosa. Phytochemistry, 1973; 12:238.
23.
DongH, ChenS-X, XuH-X, KadotaS, NambaT: A new antiplatelet diarylheptanoid from alpinia blepharocalyx. J Nat Prod, 1998; 61:142–144.
24.
HuangY, YaoXQ, TsangSY, LauCW, ChenZY: Role of endothelium/nitric oxide in vascular response, to flavonoids and epicatechin. Acta Pharmacol Sin, 2000; 21:1119–1124.
25.
LeHT, PhanMG, PhanTS: Biologically active phenolic constituents from Alpinia gagnepainii K. Schum (Zingiberaceae). Tap Chi Hoa Hoc, 2007; 45:126–130.
26.
LeeJ-H, JungHS, GiangPM, et al.: Blockade of nuclear factor-κB signaling pathway and anti-inflammatory activity of cardamomin, a chalcone analog from Alpinia conchigera. J Pharmacol Exp Ther, 2006; 316:271–278.
27.
LeHT, PhanMG, PhanTS: Further study on chemical constituents and biological activities of Alpinia conchigera Griff. (Zingiberaceae). Tap Chi Hoa Hoc, 2007; 45:260–264.
28.
HeY-q, YangL, LiuY, et al.: Characterization of cardamonin metabolism by P450 in different species via HPLC-ESI-ion trap and UPLC-ESI-quadrupole mass spectrometry. Acta Pharmacol Sin, 2009; 30:1462–1470.
29.
ZhangQ, MyintA, CuiH, GeX, LiuL, ChouG: Determination of cardamonin using a chemiluminescent flow-injection method. Phytochem Anal, 2005; 16:440–445.
30.
WangS, ZhouL, HeW, HuZ: Separation and determination of alpinetin and cardamonin by reverse micelle electrokinetic capillary chromatography. J Pharm Biomed Anal, 2007; 43:1557–1561.
31.
LiuL, ChenX, HuZ: Separation and determination of alpinetin and cardamonin in Alpinia katsumadai Hayata by flow injection–micellar electrokinetic chromatography. Talanta, 2007; 71:155–159.
32.
HuangWZ, ZhangCF, ZhangM, WangZT: A new biphenylpropanoid from Alpinia katsumadai. J Chin Chem Soc, 2007; 54:1553–1556.
33.
LiY-Y, ChouG-X, WangZ-T: New Diarylheptanoids and Kavalactone from Alpinia katsumadai Hayata. Helv Chim Acta, 2010; 93:382–388.
34.
YamamotoN, KawabataK, SawadaK, et al.: Cardamonin Stimulates Glucose Uptake through Translocation of Glucose Transporter-4 in L6 Myotubes. Phytother Res, 2011; 25:1218–1224.
35.
LiaoQ, ShiD-H, ZhengW, XuX-J, YuY-H: Antiproliferation of cardamonin is involved in mTOR on aortic smooth muscle cells in high fructose-induced insulin resistance rats. Eur J Pharmacol, 2010; 641:179–186.
36.
LeeM-Y, SeoC-S, LeeJ-A, et al.: Alpinia katsumadai HAYATA Seed Extract Inhibit LPS-Induced Inflammation by Induction of Heme Oxygenase-1 in RAW264.7 Cells. Inflammation, 2012; 35:746–757.
NgoK-S, BrownGD: Stilbenes, monoterpenes, diarylheptanoids, labdanes and chalcones from Alpinia katsumadai. Phytochemistry, 1998; 47:1117–1123.
39.
XiaoX, SiX, TongX, LiG: Preparation of flavonoids and diarylheptanoid from Alpinia katsumadai hayata by microwave-assisted extraction and high-speed counter-current chromatography. Sep Purif Technol, 2011; 81:265–269.
40.
WangZ-T, LauC-W, ChanFL, et al.: Vasorelaxant effects of cardamonin and alpinetin from Alpinia henryi K. Schum. J Cardiovasc Pharmacol, 2001; 37:596–606.
41.
NuntawongN, SuksamrarnA: Chemical constituents of the rhizomes of Alpinia malaccensis. Biochem Syst Ecol, 2008; 36:661–664.
42.
JantanI, RawehSM, SiratHM, et al.: Inhibitory effect of compounds from Zingiberaceae species on human platelet aggregation. Phytomedicine, 2008; 15:306–309.
43.
JantanI, PisarM, SiratHM, et al.: Inhibitory effects of compounds from Zingiberaceae species on platelet activating factor receptor binding. Phytother Res, 2004; 18:1005–1007.
44.
LinE, LinW-H, WangS-Y, et al.: Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo. J Nutr Biochem, 2012; 23:368–378.
45.
MohamadH, AbasF, PermanaD, et al.: DPPH free radical scavenger components from the fruits of Alpinia rafflesiana Wall. ex. Bak. (Zingiberaceae). Z Naturforsch C, 2004; 59:811–815.
46.
ChowY-L, LeeK-H, VidyadaranS, et al.: Cardamonin from Alpinia rafflesiana inhibits inflammatory responses in IFN-γ/LPS-stimulated BV2 microglia via NF-κB signalling pathway. Int Immunopharmacol, 2012; 12:657–665.
47.
IsrafDA, KhaizurinTA, SyahidaA, LajisNH, KhozirahS: 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, 2007; 44:673–679.
48.
AhmadS, IsrafDA, LajisNH, et al.: Cardamonin, inhibits pro-inflammatory mediators in activated RAW 264.7 cells and whole blood. Eur J Pharmacol, 2006; 538:188–194.
49.
OhtsukiT, KikuchiH, KoyanoT, KowithayakornT, SakaiT, IshibashiM: Death receptor 5 promoter-enhancing compounds isolated from Catimbium speciosum and their enhancement effect on TRAIL-induced apoptosis. Biorg Med Chem, 2009; 17:6748–6754.
50.
ItokawaH, MoritaM, MihashiS: Phenolic compounds from the rhizomes of Alpinia speciosa. Phytochemistry, 1981; 20:2503–2506.
51.
Bheemasankara RaoC, Namosiva RaoT, SuryaprakasamS: Cardamonin and alpinetin from the seeds of Amomum subulatum. Planta Med, 1976; 29:391–392.
52.
HatziieremiaS, GrayAI, FerroVA, PaulA, PlevinR: The effects of cardamonin on lipopolysaccharide-induced inflammatory protein production and MAP kinase and NFκB signalling pathways in monocytes/macrophages. Br J Pharmacol, 2006; 149:188–198.
53.
TewtrakulS, SubhadhirasakulS, PuripattanavongJ, PanphadungT: HIV-1 protease inhibitory substances from the rhizomes of Boesenbergia pandurata Holtt. Songklanakarin J Sci Technol, 2003; 25:503–508.
54.
TewtrakulS, SubhadhirasakulS, KaralaiC, PonglimanontC, CheenprachaS: Anti-inflammatory effects of compounds from Kaempferia parviflora and Boesenbergia pandurata. Food Chem, 2009; 115:534–538.
55.
TrakoontivakornG, NakaharaK, ShinmotoH, et al.: Structural analysis of a novel antimutagenic compound, 4-hydroxypanduratin A, and the antimutagenic activity of flavonoids in a Thai spice, fingerroot (Boesenbergia pandurata Schult.) against mutagenic heterocyclic amines. J Agric Food Chem, 2001; 49:3046–3050.
56.
MurakamiA, KondoA, NakamuraY, OhigashiH, KoshimizuK: Possible anti-tumor promoting properties of edible plants from thailand, and identification of an active constituent, cardamonin, of Boesenbergia pandurata. Biosci Biotechnol Biochem, 1993; 57:1971–1973.
WinNN, AwaleS, EsumiH, TezukaY, KadotaS: Bioactive Secondary Metabolites from Boesenbergia pandurata of Myanmar and Their Preferential Cytotoxicity against Human Pancreatic Cancer PANC-1 Cell Line in Nutrient-Deprived Medium. J Nat Prod, 2007; 70:1582–1587.
60.
PandjiC, GrimmC, WrayV, WitteL, ProkschP: Insecticidal constituents from four species of the zingiberaceae. Phytochemistry, 1993; 34:415–419.
61.
KiatTS, PippenR, YusofR, IbrahimH, KhalidN, RahmanNA: Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease. Bioorg Med Chem Lett, 2006; 16:3337–3340.
62.
MorikawaT, FunakoshiK, NinomiyaK, et al.: Medicinal foodstuffs. XXXIV. structures of new prenylchalcones and prenylflavanones with TNF-α and aminopeptidase N inhibitory activities from Boesenbergia rotunda. Chem Pharm Bull (Tokyo), 2008; 56:956–962.
63.
CaoX-D, DingZ-S, JiangF-S, et al.: Antitumor constituents from the leaves of Carya cathayensis. Nat Prod Res, 2012; 26:2089–2094.
64.
KoorbanallyNA, RandrianarivelojosiaM, MulhollandDA, Quarles van UffordL, van den BergAJJ: Chalcones from the seed of Cedrelopsis grevei (Ptaeroxylaceae). Phytochemistry, 2003; 62:1225–1229.
65.
AderogbaMA, KgatleDT, McGawLJ, EloffJN: Isolation of antioxidant constituents from Combretum apiculatum subsp. apiculatum. S Afr J Bot, 2012; 79:125–131.
66.
WollenweberE, KohorstG, MannK, BellJM: Leaf Gland Flavonoids in Comptonia peregrina and Myrica pensylvanica (Myricaceae). J Plant Physiol, 1985; 117:423–430.
67.
BajgaiSP, PrachyawarakornV, MahidolC, RuchirawatS, KittakoopP: Hybrid flavan-chalcones, aromatase and lipoxygenase inhibitors, from Desmos cochinchinensis. Phytochemistry, 2011; 72:2062–2067.
68.
CarvalhoAM, GonçalvesLM, ValenteIM, RodriguesJA, BarrosAA: Analysis of cardamonin by square wave voltammetry. Phytochem Anal, 2012; 23:396–399.
69.
Al-RehailyAJ, AlbishiOA, El-OlemyMM, MossaJS: Flavonoids and terpenoids from Helichrysum forskahlii. Phytochemistry, 2008; 69:1910–1914.
70.
TerreauxC, HostettmannMPG, Kurt: Antifungal benzoic acid derivatives from Piper Dilatatum in honour of Professor G. H. Neil Towers 75th birthday. Phytochemistry, 1998; 49:461–464.
71.
RuizC, HaddadM, AlbanJ, et al.: Activity-guided isolation of antileishmanial compounds from Piper hispidum. Phytochem Lett, 2011; 4:363–366.
72.
LópezSN, FurlanRLE, ZacchinoSA: Detection of antifungal compounds in Polygonum ferrugineum Wedd. extracts by bioassay-guided fractionation. Some evidences of their mode of action. J Ethnopharmacol, 2011; 138:633–636.
73.
AhmedM, KhaleduzzamanM, Saiful IslamM: Isoflavan-4-ol, dihydrochalcone and chalcone derivatives from Polygonum lapathifolium. Phytochemistry, 1990; 29:2009–2011.
74.
DeritaM, ZacchinoS: Chemotaxonomic importance of sesquiterpenes and flavonoids in five argentinian species of Polygonum genus. J Essent Oil Res, 2011; 23:11–14.
75.
DeritaM, ZacchinoS: Validation of the ethnopharmacological use of Polygonum persicaria for its antifungal properties. Nat Prod Commun, 2011; 6:931–933.
76.
EnglishS, GreenawayW, WhatleyFR: Analysis of phenolics in the bud exudates of Populus deltoides, P. fremontii, P. sargentii and P. Wislizenii by GC-MS. Phytochemistry, 1992; 31:1255–1260.
77.
GreenawayW, ScaysbrookT, WhatleyFR: The analysis of bud exudate of populus euramericana, and of propolis, by gas chromatography—mass spectrometry. Proc R S Lond B Biol Sci, 1987; 232:249–272.
78.
SimirgiotisMJ, AdachiS, ToS, et al.: Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu). Food Chem, 2008; 107:813–819.
79.
ThuyTT, PorzelA, RippergerH, SungTV, AdamG: Chalcones and ecdysteroids from Vitex leptobotrys. Phytochemistry, 1998; 49:2603–2605.
80.
EconomidesC, AdamK-P: Lipophilic flavonoids from the fern Woodsia scopulina. Phytochemistry, 1998; 49:859–862.
81.
TakahashiA, YamamotoN, MurakamiA: Cardamonin suppresses nitric oxide production via blocking the IFN-γ/STAT pathway in endotoxin-challenged peritoneal macrophages of ICR mice. Life Sci, 2011; 89:337–342.
82.
SenR, BaltimoreD: Inducibility of κ immunoglobulin enhancer-binding protein NF-κB by a posttranslational mechanism. Cell, 1986; 47:921–928.
83.
JinF, JinX, JinY, et al.: Structural requirements of 2′,4′,6′-tris(methoxymethoxy) chalcone derivatives for anti-inflammatory activity: The importance of a 2′-hydroxy moiety. Arch Pharm Res, 2007; 30:1359–1367.
84.
MarquesSM, Esteves da SilvaJCG: Firefly bioluminescence: a mechanistic approach of luciferase catalyzed reactions. IUBMB Life, 2009; 61:6–17.
85.
QinY, SunC-Y, LuF-R, et al.: Cardamonin exerts potent activity against multiple myeloma through blockade of NF-κB pathway in vitro. Leuk Res, 2012; 36:514–520.
86.
YadavVR, PrasadS, AggarwalBB: Cardamonin sensitizes tumour cells to TRAIL through ROS- and CHOP-mediated up-regulation of death receptors and down-regulation of survival proteins. Br J Pharmacol, 2012; 165:741–753.
87.
LiN, LiuJ-H, ZhangJ, YuB-Y: Comparative Evaluation of Cytotoxicity and Antioxidative Activity of 20 Flavonoids. J Agric Food Chem, 2008; 56:3876–3883.
88.
ZhuJTT, ChoiRCY, ChuGKY, et al.: Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 Cells: a comparison of different flavonoids in activating estrogenic effect and in preventing β-amyloid-induced cell death. J Agric Food Chem, 2007; 55:2438–2445.
89.
FusiF, CavalliM, MulhollandD, et al.: Cardamonin is a bifunctional vasodilator that inhibits Cav1.2 current and stimulates KCa1.1 current in rat tail artery myocytes. J Pharmacol Exp Ther, 2010; 332:531–540.
90.
OthmanR, KiatTS, KhalidN, et al.: Docking of noncompetitive inhibitors into dengue virus type 2 protease: understanding the interactions with allosteric binding sites. J Chem Inf Model, 2008; 48:1582–1591.
91.
ChoM, RyuM, JeongY, et al.: Cardamonin suppresses melanogenesis by inhibition of Wnt/β-catenin signaling. Biochem Biophys Res Commun, 2009; 390:500–505.
92.
HirataH, TakazumiK, SegawaS, et al.: Xanthohumol, a prenylated chalcone from Humulus lupulus L., inhibits cholesteryl ester transfer protein. Food Chem, 2012; 134:1432–1437.
93.
HeW, LiY, LiuJ, HuZ, ChenX: Specific interaction of chalcone-protein: Cardamonin binding site II on the human serum albumin molecule. Biopolymers, 2005; 79:48–57.
94.
HeW, LiY, TangJ, LuanF, JinJ, HuZ: Comparison of the characterization on binding of alpinetin and cardamonin to lysozyme by spectroscopic methods. Int J Biol Macromol, 2006; 39:165–173.
95.
TavaresEM, CarvalhoAM, GonçalvesLM, et al.: Chemical sensing of chalcones by voltammetry: trans-chalcone, cardamonin and xanthohumol. Electrochim Acta, 2013; 90:440–444.
