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Journal of Natural Medicines
Published in: Journal of Natural Medicines 1/2018

Open Access 01-01-2018 | Review

Enzyme-linked immunosorbent assay for the quantitative/qualitative analysis of plant secondary metabolites

Authors: Seiichi Sakamoto, Waraporn Putalun, Sornkanok Vimolmangkang, Waranyoo Phoolcharoen, Yukihiro Shoyama, Hiroyuki Tanaka, Satoshi Morimoto

Published in: Journal of Natural Medicines | Issue 1/2018

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Abstract

Immunoassays are antibody-based analytical methods for quantitative/qualitative analysis. Since the principle of immunoassays is based on specific antigen–antibody reaction, the assays have been utilized worldwide for diagnosis, pharmacokinetic studies by drug monitoring, and the quality control of commercially available products. Berson and Yalow were the first to develop an immunoassay, known as radioimmunoassay (RIA), for detecting endogenous plasma insulin [1], a development for which Yalow was awarded the Nobel Prize in Physiology or Medicine in 1977. Even today, after half a century, immunoassays are widely utilized with some modifications from the originally proposed system, e.g., radioisotopes have been replaced with enzymes because of safety concerns regarding the use of radioactivity, which is referred to as enzyme immunoassay/enzyme-linked immunosorbent assay (ELISA). In addition, progress has been made in ELISA with the recent advances in recombinant DNA technology, leading to increase in the range of antibodies, probes, and even systems. This review article describes ELISA and its applications for the detection of plant secondary metabolites.
Literature
1.
2.
3.
Bennett RN, Wallsgrove RM (1999) Secondary metabolites in plant defence mechanisms. New Phytol 127:617–633CrossRef
4.
5.
Bourgaud F, Gravot A, Milesi S, Gontier E (2001) Production of plant secondary metabolites: a historical perspective. Plant Sci 161:839–851CrossRef
6.
7.
Avrameas S, Ternynck T, Guesdon JL (1978) Coupling of enzymes to antibodies and antigens. Scand J Immunol 8:7–23CrossRef
8.
Nakane PK, Kawaoi A (1974) Peroxidase-labeled antibody. A new method of conjugation. J Histochem Cytochem 22:1084–1091CrossRefPubMed
9.
Craven GR, Steers E, Anfinsen CB (1965) Purification, composition and molecular weight of the β-galactosidase of Escherichia coli K12. J Biol Chem 240:2468–2477PubMed
10.
Dray F, Andrieu JM, Renaud F (1975) Enzyme immunoassay of progesterone at the pictogram level using β-galactosidase as label. Biochim Biophys Acta 403:131–138CrossRefPubMed
11.
Comoglio S, Celada F (1976) An immuno-enzymatic assay of cortisol using E. coli β-galactosidase as label. J Immunol Methods 10:161–170CrossRefPubMed
12.
Hitchcock CHS, Bailey FJ, Crimes AA, Dean DAG, Davis PJ (1981) Determination of soya proteins in food using an enzyme-linked immunosorbent assay procedure. J Sci Food Agric 32:157–165CrossRef
13.
14.
Engvall E, Perlmann P (1971) Enzyme-linked immunosorbent assay (ELISA). Quant Assay immunoglobul G Immunochem 8:871–874
15.
Van Weemen BK, Schuurs AH (1971) Immunoassay using antigen-enzyme conjugates. FEBS Lett 15:232–236CrossRefPubMed
16.
Belanger L, Sylvestre C, Dufour D (1973) Enzyme-linked immunoassay for alpha-fetoprotein by competitive and sandwich procedures. Clin Chim Acta 48:15–18CrossRefPubMed
17.
Lindström P, Wager O (1978) IgG autoantibody to human serum albumin studied by the ELISA-technique. Scand J Immunol 7:419–425CrossRefPubMed
18.
Slightom EL (1978) The analysis of drugs in blood, bile, and tissue with an indirect homogeneous enzyme immunoassay. J Forensic Sci 23:292–303CrossRefPubMed
19.
Nierwenhuijzen Kruseman AC (1983) Application of ELISA for assessment of antiserum immunoreactivity in endocrine immunocytochemical studies. J Clin Pathol 36:406–410CrossRefPubMedPubMedCentral
20.
Matyjaszek-Matuszek B, Pyzik A, Nowakowski A, Jarosz MJ (2013) Diagnostic methods of TSH in thyroid screening tests. Ann Agric Environ Med 20:731–735PubMed
21.
Oguri H, Hirama M, Tsumuraya T, Fujii I, Maruyama M, Uehara H, Nagumo Y (2003) Synthesis-based approach toward direct sandwich immunoassay for ciguatoxin CTX3C. J Am Chem Soc 125:7608–7612CrossRefPubMed
22.
Boscolo S, Pelin M, De Bortoli M, Fontanive G, Barreras A, Berti F, Sosa S, Chaloin O, Bianco A, Yasumoto T, Prato M, Poli M, Tubaro A (2013) Sandwich ELISA assay for the quantitation of palytoxin and its analogs in natural samples. Environ Sci Technol 47:2034–2042CrossRefPubMed
23.
Ueda H, Tsumoto K, Kubota K, Suzuki E, Nagamune T, Nishimura H, Schueler PA, Winter G, Kumagai I, Mohoney WC (1996) Open sandwich ELISA: a novel immunoassay based on the interchain interaction of antibody variable region. Nat Biotechnol 14:1714–1718CrossRefPubMed
24.
Suzuki T, Munakata Y, Morita K, Shinoda T, Ueda H (2007) Sensitive detection of estrogenic mycotoxin zearalenone by open sandwich immunoassay. Anal Sci 23:65–70CrossRefPubMed
25.
Ihara M, Suzuki T, Kobayashi N, Goto J, Ueda H (2009) Open-sandwich enzyme immunoassay for one-step noncompetitive detection of corticosteroid 11-deoxycortisol. Anal Chem 81:8298–8304CrossRefPubMed
26.
Islam KN, Ihara M, Dong J, Kasagi N, Mori T, Ueda H (2011) Direct construction of an open-sandwich enzyme immunoassay for one-step noncompetitive detection of thyroid hormone T4. Anal Chem 83:1008–1014CrossRefPubMed
27.
Hara Y, Dong J, Ueda H (2013) Open-sandwich immunoassay for sensitive and broad-range detection of a shellfish toxin gonyautoxin. Anal Chim Acta 793:107–113CrossRefPubMed
28.
Köhler G, Milstein C (1975) Continuous cultures of fused cells secreting antibody of predefined specificity. Nature 256:495–497CrossRefPubMed
29.
Holliger P, Hudson PJ (2005) Engineered antibody fragments and the rise of single domains. Nat Biotechnol 23:1126–1136CrossRefPubMed
30.
Hadacek F, Bachmann G (2015) Low-molecular-weight metabolite systems chemistry. Front Environ Sci 3:12CrossRef
31.
Harborne JB (1999) Classes and functions of secondary products. In: Walton NJ, Brown DE (eds) Chemicals from plants, perspectives secondary plant products. Imperial College Press, London, pp 1–25
32.
Pongkitwitoon B, Sakamoto S, Tanaka H, Tsuchihashi R, Kinjo J, Morimoto S, Putalun W (2010) Enzyme-linked immunosorbent assay for total isoflavonoids in Pueraria candollei using anti-puerarin and anti-daidzin polyclonal antibodies. Planta Med 76:831–836CrossRefPubMed
33.
Sakamoto S, Yusakul G, Pongkitwitoon B, Paudel MK, Tanaka H, Morimoto S (2015) Simultaneous determination of soy isoflavone glycosides, daidzin and genistin by monoclonal antibody-based highly sensitive indirect competitive enzyme-linked immunosorbent assay. Food Chem 169:127–133CrossRefPubMed
34.
Lu Z, Morinaga O, Tanaka H, Shoyama Y (2003) A quantitative ELISA using monoclonal antibody to survey paeoniflorin and albiflorin in crude drugs and traditional Chinese herbal medicines. Biol Pharm Bull 26:862–866CrossRefPubMed
35.
Ishiyama M, Shoyama Y, Murakami H, Shinohara H (1995) Production of monoclonal antibodies and development of an ELISA for solamargine. Cytotechnology 18:153–158CrossRefPubMed
36.
Phrompittayarat W, Putalun W, Tanaka H, Jetiyanon K, Wittaya-Areekul S, Ingkaninan K (2007) Determination of pseudojujubogenin glycosides from Brahmi based on immunoassay using a monoclonal antibody against bacopaside I. Phytochem Anal 18:411–418CrossRefPubMed
37.
Zhu S, Shimokawa S, Shoyama Y, Tanaka H (2006) A novel analytical ELISA-based methodology for pharmacologically active saikosaponins. Fitoterapia 77:100–108CrossRefPubMed
38.
Fujii S, Morinaga O, Uto T, Nomura S, Shoyama Y (2014) Development of a monoclonal antibody-based immunochemical assay for liquiritin and its application to the quality control of licorice products. J Agric Food Chem 62:3377–3383CrossRefPubMed
39.
Yusakul G, Sakamoto S, Juengwatanatrakul T, Putalun W, Tanaka H, Morimoto S (2016) Preparation and application of a monoclonal antibody against the isoflavone glycoside daidzin using a Mannich reaction-derived hapten conjugate. Phytochem Anal 27:81–88CrossRefPubMed
40.
Kitisripanya T, Jutathis K, Inyai C, Komaikul J, Udomsin O, Yusakul G, Tanaka H, Putalun W (2016) Anti-miroestrol polyclonal antibodies: a comparison of immunogen preparations used to obtain desired antibody properties. J Nat Med 70:296–299CrossRefPubMed
41.
Tanaka H, Xuan LJ, Morimoto S, Shoyama Y, Isobe R, Nojima K (2001) Direct determination of naturally occurring biologically active compound–serum albumin conjugate by matrix-assisted laser desorption/ionization mass spectrometry. J Spectrosc 15:1–18CrossRef
42.
Singh KV, Kaur J, Varshney GC, Raje M, Suri CR (2004) Synthesis and characterization of hapten-protein conjugates for antibody production against small molecules. Bioconjug Chem 15:168–173CrossRefPubMed
43.
Sakamoto S, Yusakul G, Tsuneura Y, Putalun W, Usui K, Miyamoto T, Tanaka H, Morimoto S (2017) Sodium periodate-mediated conjugation of harringtonine enabling the production of a highly specific monoclonal antibody, and the development of a sensitive quantitative analysis method. Analyst 142:1140–1148CrossRefPubMed
44.
Sakamoto S, Nagamitsu R, Yusakul G, Miyamoto T, Tanaka H, Morimoto S (2017) Ultrasensitive immunoassay for monocrotaline using monoclonal antibody produced by N,N′-carbonyldiimidazole mediated hapten-carrier protein conjugates. Talanta 168:67–72CrossRefPubMed
45.
46.
Tanaka H, Fukuda N, Shoyama Y (1999) Formation of monoclonal antibody against a major ginseng component, ginsenoside Rb1 and its characterization. Cytotechnology 29:115–120CrossRefPubMedPubMedCentral
47.
Joo EJ, Ha YW, Shin H, Son SH, Kim YS (2009) Generation and characterization of monoclonal antibody to ginsenoside Rg3. Biol Pharm Bull 32:548–552CrossRefPubMed
48.
Morinaga O, Tanaka H, Shoyama Y (2006) Detection and quantification of ginsenoside Re in ginseng samples by a chromatographic immunostaining method using monoclonal antibody against ginsenoside Re. J Chromatogr B 830:100–104CrossRef
49.
Fukuda N, Tanaka H, Shoyama Y (2000) Formation of monoclonal antibody against a major ginseng component, ginsenoside Rg1 and its characterization. Monoclonal antibody for a ginseng saponin. Cytotechnology 34:197–204CrossRefPubMedPubMedCentral
50.
Qu H, Wang Y, Shan W, Zhang Y, Feng H, Sai J, Wang Q, Zhao Y (2015) Development of ELISA for detection of Rh1 and Rg2 and potential method of immunoaffinity chromatography for separation of epimers. J Chromatogr B 985:197–205CrossRef
51.
Morinaga O, Tanaka H, Shoyama Y (2006) Enzyme-linked immunosorbent assay for the determination of total ginsenosides in ginseng. Anal Lett 39:287–296CrossRef
52.
Sritularak B, Morinaga O, Yuan CS, Shoyama Y, Tanaka H (2009) Quantitative analysis of ginsenosides Rb1, Rg1, and Re in American ginseng berry and flower samples by ELISA using monoclonal antibodies. J Nat Med 63:360–363CrossRefPubMed
53.
Wei TQ, Zheng YF, Dubowy M, Sharma M (2014) Sandwich assay for tacrolimus using 2 antitacrolimus antibodies. Clin Chem 60:621–630CrossRefPubMed
54.
Towbin H, Motz J, Oroszlan P, Zingel O (1995) Sandwich immunoassay for the hapten angiotensin II. A novel assay principle based on antibodies against immune complexes. J Immunol Methods 181:167–176CrossRefPubMed
55.
Qu H, Wang X, Qu B, Kong H, Zhang Y, Shan W, Cheng J, Wang Q, Zhao Y (2016) Sandwich enzyme-linked immunosorbent assay for naringin. Anal Chim Acta 903:149–155CrossRefPubMed
56.
Better M, Chang CP, Robinson RR, Horwitz AH (1988) Escherichia coli secretion of an active chimeric antibody fragment. Science 240:1041–1043CrossRefPubMed
57.
Jost CR, Kurucz I, Jacobus CM, Titus JA, George AJT, Segal DM (1994) Mammalian expression and secretion of functional single-chain Fv molecules. J Biol Chem 269:26267–26273PubMed
58.
Bei R, Schlom J, Kashmiri SV (1995) Baculovirus expression of a functional single-chain immunoglobulin and its IL-2 fusion protein. J Immunol Methods 186:245–255CrossRefPubMed
59.
Davis GT, Bedzyk WD, Voss EW, Jacobs TW (1991) Single chain antibody (SCA) encoding genes: one-step construction and expression in eukaryotic cells. Biotechnology 9:165–169PubMed
60.
Whitelam GC, Cockburn W, Owen MR (1994) Antibody production in transgenic plants. Biochem Soc Trans 22:940–945CrossRefPubMed
61.
Sakamoto S, Taura F, Putalun W, Pongkitwitoon B, Tsuchihashi R, Morimoto S, Kinjo J, Shoyama Y, Tanaka H (2009) Construction and expression of specificity-improved single-chain variable fragments against the bioactive naphthoquinone, plumbagin. Biol Pharm Bull 32:434–439CrossRefPubMed
62.
Pongkitwitoon B, Sakamoto S, Morinaga O, Juengwatanatrakul T, Shoyama Y, Tanaka H, Morimoto S (2011) Single-chain variable fragment antibody against ginsenoside Re as an effective tool for the determination of ginsenosides in various ginsengs. J Nat Med 65:24–30CrossRefPubMed
63.
Yusakul G, Sakamoto S, Pongkitwitoon B, Tanaka H, Morimoto S (2016) Effect of linker length between variable domains of single chain variable fragment antibody against daidzin on its reactivity. Biosci Biotechnol Biochem 80:1306–1312CrossRefPubMed
64.
Paudel MK, Sakamoto S, Huy LV, Tanaka H, Miyamoto T, Morimoto S (2017) The effect of varying the peptide linker length in a single chain variable fragment antibody against wogonin glucuronide. J Biotechnol 251:47–52CrossRefPubMed
65.
Yusakul G, Sakamoto S, Tanaka H, Morimoto S (2016) Efficient expression of single chain variable fragment antibody against paclitaxel using Bombyx mori nucleopolyhedrovirus bacmid DNA system and its characterizations. J Nat Med 70:592–601CrossRefPubMed
66.
Paudel MK, Takei A, Sakoda J, Juengwatanatrakul T, Sasaki-Tabata K, Putalun W, Shoyama Y, Tanaka H, Morimoto S (2012) Preparation of a single-chain variable fragment and a recombinant antigen-binding fragment against the anti-malarial drugs, artemisinin and artesunate, and their application in an ELISA. Anal Chem 84:2002–2008CrossRefPubMed
67.
Paudel MK, Sakamoto S, Tanaka H, Morimoto S (2017) An overview and comparison of a recombinant antigen-binding fragment and an antigen-binding fragment from a monoclonal antibody against wogonin glucuronide. J Nat Med 71:703–710CrossRefPubMed
68.
Sakamoto S, Taura F, Pongkitwitoon B, Putalun W, Tsuchihashi R, Kinjo J, Tanaka H, Morimoto S (2010) Development of sensitivity-improved fluorescence-linked immunosorbent assay using a fluorescent single-domain antibody against the bioactive naphthoquinone, plumbagin. Anal Bioanal Chem 396:2955–2963CrossRefPubMed
69.
Sakamoto S, Tanizaki Y, Pongkitwitoon B, Tanaka H, Morimoto S (2011) A chimera of green fluorescent protein with single chain variable fragment antibody against ginsenosides for fluorescence-linked immunosorbent assay. Protein Expr Purif 77:124–130CrossRefPubMed
Metadata
Title
Enzyme-linked immunosorbent assay for the quantitative/qualitative analysis of plant secondary metabolites
Authors
Seiichi Sakamoto
Waraporn Putalun
Sornkanok Vimolmangkang
Waranyoo Phoolcharoen
Yukihiro Shoyama
Hiroyuki Tanaka
Satoshi Morimoto
Publication date
01-01-2018
Publisher
Springer Singapore
Published in
Journal of Natural Medicines / Issue 1/2018
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-017-1144-z

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