Characterization of Isoflavones from Seed of Selected Soybean (Glycine max L.) Resources Using High-Resolution Mass Spectrometry |
Lee, So-Jeong
(Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA)
Kim, Heon-Woong (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Lee, Suji (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Na, Hyemin (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Kwon, Ryeong Ha (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Kim, Ju Hyung (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Yoon, Hyemyeong (National Agrobiodiversity Center, National Institute of Agricultural Sciences, RDA) Choi, Yu-Mi (National Agrobiodiversity Center, National Institute of Agricultural Sciences, RDA) Wee, Chi-Do (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Yoo, Seon Mi (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) Lee, Sang Hoon (Dept. of Agro-Food Resources, National Institute of Agricultural Sciences, RDA) |
1 | Ruiz-Larrea MB, Mohan AR, Paganga G, Miller NJ, Bolwell GP, Rice-Evans CA. 1997. Antioxidant activity of phytoestrogenic isoflavones. Free Radic Res 26:63-70 DOI |
2 | Seo WD, Kang JE, Choi SW, Lee KS, Lee MJ, Park KD, Lee JH. 2017. Comparison of nutritional components (isoflavone, protein, oil, and fatty acid) and antioxidant properties at the growth stage of different parts of soybean [Glycine max (L.) Merrill]. Food Sci Biotechnol 26:339-347 DOI |
3 | Setchell KD. 1998. Phytoestrogens: The biochemistry, physiology, and implications for human health of soy isoflavones. Am J Clin Nutr 68:1333S-1346S |
4 | Kim EH, Kim SL, Kim SH, Chung IM. 2012a. Comparison of isoflavones and anthocyanins in soybean [Glycine max (L.) Merrill] seeds of different planting dates. J Agric Food Chem 60:10196-10202 DOI |
5 | Kim EH, Lee OK, Kim JK, Kim SL, Lee J, Kim SH, Chung IM. 2014. Isoflavones and anthocyanins analysis in soybean (Glycine max (L.) Merrill) from three different planting locations in Korea. Field Crops Res 156:76-83 DOI |
6 | Kim EH, Ro HM, Kim SL, Kim HS, Chung IM. 2012b. Analysis of isoflavone, phenolic, soyasapogenol, and tocopherol compounds in soybean [Glycine max (L.) Merrill] germplasms of different seed weights and origins. J Agric Food Chem 60:6045-6055 DOI |
7 | Kim HW, Lee SH, Asamenew G, Lee MK, Lee S, Park JJ, Choi Y, Lee SH. 2019. Study on phenolic compounds in lettuce samples cultivated from Korea using UPLC-DAD-QToF/MS. Korean J Food Nutr 32:717-729 |
8 | Kim JA, Chung IM. 2007. Change in isoflavone concentration of soybean (Glycine max L.) seeds at different growth stages. J Sci Food Agric 87:496-503 DOI |
9 | Kim SL, Berhow MA, Kim JT, Chi HY, Lee SJ, Chung IM. 2006. Evaluation of soyasaponin, isoflavone, protein, lipid, and free sugar accumulation in developing soybean seeds. J Agric Food Chem 54:10003-10010 DOI |
10 | Kirakosyan A, Kaufman P, Nelson RL, Kasperbauer MJ, Duke JA, Seymour E, Chang SC, Warber S, Bolling S. 2006. Isoflavone levels in five soybean (Glycine max) genotypes are altered by phytochrome-mediated light treatments. J Agric Food Chem 54:54-58 DOI |
11 | Kudou S, Fleury Y, Welti D, Magnolato D, Uchida T, Kitamura K, Okubo K. 1991a. Malonyl isoflavone glycosides in oybean seeds (Glycine max Merrill). J Agric Biol Chem 55:2227-2233 |
12 | Verdrengh M, Jonsson IM, Holmdahl R, Tarkowski A. 2003. Gentistein as an anti-inflammatory agent. Inflamm Res 52:341-346 DOI |
13 | Sturtz M, Lander V, Schmid W, Winterhalter P. 2006. Preparative isolation of isoflavones from soy and red clover. Mol Nutr Food Res 50:356-361 DOI |
14 | Suh HJ, Kim YS, Chung SH, Kim YS, Lee SD. 1996. Functionality and inhibitory effect of soybean hydrolysate on angiotensin converting enzyme. Korean J Food Nut 9:167-175 |
15 | Szymczak G, Wojciak-Kosior M, Sowa I, Zapala K, Strzemski M, Kocjan R. 2017. Evaluation of isoflavone content and antioxidant activity of selected soy taxa. J Food Compost Anal 57:40-48 DOI |
16 | Wu Q, Wang M, Sciarappa WJ, Simon JE. 2004. LC/UV/ESI-MS analysis of isoflavones in edamame and tofu soybeans. J Agric Food Chem 52:2763-2769 DOI |
17 | Kudou S, Shimoyamada M, Imura T, Uchida T, Okubo K. 1991b. A new isoflavone glycoside in soybean seeds (Glycine max Merrill), Glycitein 7-O-β-D-(6"-O-acetyl)-glucopyranoside. J Agric Biol Chem 55:859-860 |
18 | Vyn TJ, Yin X, Bruulsema TW, Jackson CJC, Rajcan I, Brouder SM. 2002. Potassium fertilization effects on isoflavone concentrations in soybean [Glycine max (L.) Merr.]. J Agric Food Chem 50:3501-3506 DOI |
19 | Wang J, Sporns P. 2000. MALDI-TOF MS analysis of isoflavones in soy products. J Agric Food Chem 48:5887-5892 DOI |
20 | Wu HJ, Deng JC, Yang C, Zhang J, Zhang Q, Wang XC, Yang F, Yang W, Liu J. 2017. Metabolite profiling of isoflavones and anthocyanins in black soybean [Glycine max (L.) Merr.] seeds by HPLC-MS and geographical differentiation analysis in Southwest China. Anal Methods 9:792-802 DOI |
21 | Carneiro AM, Moreira EA, Bragagnolo FS, Borges MS, Pilon AC, Rinaldo D, Funari CS. 2020. Soya agricultural waste as a rich source of isoflavones. Food Res Int 130:108949 DOI |
22 | Carrao-Panizzi MC, Beleia ADP, Kitamura K, Oliveira MCN. 1999. Effects of genetics and environment on isoflavone content of soybean from different regions of Brazil. Pesqui Agropecu Bras 34:1787-1795 |
23 | Lee JH, Hwang SR, Lee YH, Kim K, Cho KM, Lee YB. 2015b. Changes occurring in compositions and antioxidant properties of healthy soybean seeds [Glycine max (L.) Merr.] and soybean seeds diseased by Phomopsis longicolla and Cercospora kikuchii fungal pathogens. Food Chem 185: 205-211 DOI |
24 | Landete JM, Hernandez T, Robredo S, Duenas M, de Las Rivas B, Estrella I, Munoz R. 2015. Effect of soaking and fermentation on content of phenolic compounds of soybean (Glycine max cv. Merit) and mung beans (Vigna radiata [L] Wilczek). Int J Food Sci Nutr 66:203-209 DOI |
25 | Lee CH, Yang L, Xu JZ, Yeung SYV, Huang Y, Chen ZY. 2005. Relative antioxidant activity of soybean isoflavones and their glycosides. Food Chem 90:735-741 DOI |
26 | Lee JH, Ha TJ, Baek IY, Han WY, Cho KM, Park KY, Choung MG. 2008b. Evaluation of isoflavones from the leaves of soybean (Glycine max L.) cultivars. J Appl Biol Chem 51: 172-175 DOI |
27 | Lee MH, Park YH, Oh HS, Kwak TS. 2002. Isoflavone content in soybean and its processed products. Korean J Food Sci Technol 34:365-369 |
28 | Lee MJ, Chung IM, Kim H, Jung MY. 2015a. High resolution LC-ESI-TOF-mass spectrometry method for fast separation, identification, and quantification of 12 isoflavones in soybeans and soybean products. Food Chem 176:254-262 DOI |
29 | Lee S, Lee YB, Kim HS. 2013. Analysis of the general functional components of various soybeans. J Korean Soc Food Sci Nutr 42:1255-1262 DOI |
30 | Charron CS, Allen FL, Johnson RD, Pantalone VR, Sams CE. 2005. Correlations of oil and protein with isoflavone concentration in soybean [Glycine max (L.) Merr.]. J Agric Food Chem 53:7128-7135 DOI |
31 | Clarke DB, Barnes KA, Lloyd AS. 2004. Determination of unusual soya and non-soya phytoestrogen sources in beer, fish products and other foods. Food Addit Contam 21: 949-962 DOI |
32 | Gasparetto JC, Smolarek FSF, de Francisco TMG, Miranda LC, Pontarolo R, Siqueira PF. 2012. Development and validation of an HPLC-DAD method for analysis of the six major isoflavones in extracts from soybean processing. J Am Oil Chem Soc 89:1211-1222 DOI |
33 | Lee SJ, Ahn JK, Kim SH, Kim JT, Han SJ, Jung MY, Chung IM. 2003. Variation in isoflavone of soybean cultivars with location and storage duration. J Agric Food Chem 51: 3382-3389 DOI |
34 | Lee SJ, Kim JJ, Moon HI, Ahn JK, Chun SC, Jung WS, Lee OK, Chung IM. 2008a. Analysis of isoflavones and phenolic compounds in Korean soybean [Glycine max (L.) Merrill] seeds of different seed weights. J Agric Food Chem 56:2751-2758 DOI |
35 | Aguiar CL, Haddad R, Eberlin MN, Carrao-Panizzi MC, Tsai SM, Park YK. 2012. Thermal behavior of malonylglucoside isoflavones in soybean flour analyzed by RPHPLC/DAD and eletrospray ionization mass spectrometry. LWT-Food Sci Technol 48:114-119 DOI |
36 | Caldwell CR, Britz SJ, Mirecki RM. 2005. Effect of temperature, elevated carbon dioxide, and drought during seed development on the isoflavone content of dwarf soybean [Glycine max (L.) Merrill] grown in controlled environments. J Agric Food Chem 53:1125-1129 DOI |
37 | Duenas M, Hernandez T, Robredo S, Lamparski G, Estrella I, Munoz R. 2012. Bioactive phenolic compounds of soybean (Glycine max cv. Merit): Modifications by different microbiological fermentations. Pol J Food Nutr Sci 62:241-250 DOI |
38 | Gu EJ, Kim DW, Jang GJ, Song SH, Lee JI, Lee SB, Kim BM, Cho Y, Lee HJ, Kim HJ. 2017. Mass-based metabolomic analysis of soybean sprouts during germination. Food Chem 217:311-319 DOI |
39 | Gu L, Gu W. 2001. Characterization of soy isoflavones and screening for novel malonyl glycosides using high-performance liquid chromatography-electrospray ionisation-mass spectrometry. Phytochem Anal 12:377-382 DOI |
40 | Yerramsetty V, Mathias K, Bunzel M, Ismail B. 2011. Detection and structural characterization of thermally generated isoflavone malonylglucoside derivatives. J Agric Food Chem 59:174-183 DOI |
41 | Miyazawa M, Sakano K, Nakamura SI, Kosaka H. 1999. Antimutagenic activity of isoflavones from soybean seeds (Glycine max Merrill). J Agric Food Chem 47:1346-1349 DOI |
42 | Yerramsetty V. 2013. Malonyl-conjugates of isoflavones: Structure, bioavailability and chemical modifications during processing. Ph.D. Thesis, Minnesota Univ. Minnesota |
43 | Yoo KM. 2011. Effects of soybean varieties on the physiocochemical and sensory characteristics of tofu. Korean J Food Nutr 24:451-457 DOI |
44 | Lee YH, Kim B, Hwang SR, Kim K, Lee JH. 2018. Rapid characterization of metabolites in soybean using ultra high performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) and screening for α-glucosidase inhibitory and antioxidant properties through different solvent systems. J Food Drug Anal 26:277-291 DOI |
45 | Li Y, Ahmed F, Ali S, Philip PA, Kucuk O, Sarkar FH. 2005. Inactivation of nuclear factor ĸB by soy isoflavone genistein contributes to increased apoptosis induced by chemotherapeutic agents in human cancer cells. Cancer Res 65:6934-6942 DOI |
46 | Lozovaya VV, Lygin AV, Ulanov AV, Nelson RL, Dayde J, Widholm JM. 2005. Effect of temperature and soil moisture status during seed development on soybean seed isoflavone concentration and composition. Crop Sci 45:1934-1940 DOI |
47 | Ohta N, Kuwata G, Akahori H, Watanabe T. 1979. Isoflavonoid constituents of soybeans and isolation of a new acetyl daidzin. Agric Biol Chem 43:1415-1419 DOI |
48 | Huang CC, Hsu BY, Wu NL, Tsui WH, Lin TJ, Su CC, Hung CF. 2010. Anti-photoaging effects of soy isoflavone extract (aglycone and acetylglucoside form) from soybean cake. Int J Mol Sci 11:4782-4795 DOI |
49 | Ha TJ, Lee JH, Shin SO, Shin SH, Han SI, Kim HT, Ko JM, Lee MH, Park KY. 2009. Changes in anthocyanin and isoflavone concentrations in black seed-coated soybean at different planting locations. J Crop Sci Biotechnol 12:79-86 DOI |
50 | Hong JL, Qin XY, Shu P, Wang Q, Zhou ZF, Wang GK, Lin BB, Wang Q, Qin MJ. 2011. Comparative study of isoflavones in wild and cultivated soybeans as well as bean products by high-performance liquid chromatography coupled with mass spectrometry and chemometric techniques. Eur Food Res Technol 233:869-880 DOI |
51 | Huang RY, Chou CC. 2008. Heating affects the content and distribution profile of isoflavones in steamed black soybeans and black soybean Koji. J Agric Food Chem 56:8484-8489 DOI |
52 | Jang HH, Noh H, Kim HW, Cho SY, Kim HJ, Lee SH, Lee SH, Gunter MJ, Ferrari P, Scalbert A, Freisling H, Kim JB, Choe JS, Kwon O. 2020. Metabolic tracking of isoflavones in soybean products and biosamples from healthy adults after fermented soybean consumption. Food Chem 330:127317 DOI |
53 | Jia Y, Ma Y, Zou P, Cheng G, Zhou J, Cai S. 2019. Effects of different oligochitosans on isoflavone metabolites, antioxidant activity, and isoflavone biosynthetic genes in soybean (Glycine max) seeds during germination. J Agric Food Chem 67:4652-4661 DOI |
54 | John KMM, Natarajan S, Luthria DL. 2016. Metabolite changes in nine different soybean varieties grown under field and greenhouse conditions. Food Chem 211:347-355 DOI |
55 | Kim DH, Yang WT, Cho KM, Lee JH. 2020. Comparative analysis of isoflavone aglycones using microwave-assisted acid hydrolysis from soybean organs at different growth times and screening for their digestive enzyme inhibition and antioxidant properties. Food Chem 305:125462 DOI |
56 | Peng H, Li W, Li H, Deng Z, Zhang B. 2017. Extractable and non-extractable bound phenolic compositions and their antioxidant properties in seed coat and cotyledon of black soybean (Glycine max (L.) merr). J Funct Foods 32:296-312 DOI |
57 | Yuk HJ, Song YH, Curtis-Long MJ, Kim DW, Woo SG, Lee YB, Uddin Z, Kim CY, Park KH. 2016. Ethylene induced a high accumulation of dietary isoflavones and expression of isoflavonoid biosynthetic genes in soybean (Glycine max) leaves. J Agric Food Chem 64:7315-7324 DOI |
58 | Zhang S, Zheng Z, Zeng M, He Z, Tao G, Qin F, Chen J. 2017. A novel isoflavone profiling method based on UPLCPDA-ESI-MS. Food Chem 219:40-47 DOI |
59 | Park HJ, Jung MY. 2017. One step salting-out assisted liquid-liquid extraction followed by UHPLC-ESI-MS/MS for the analysis of isoflavones in soy milk. Food Chem 229:797-804 DOI |
60 | Ravindranath MH, Muthugounder S, Presser N, Viswanathan S. 2004. Anticancer therapeutic potential of soy isoflavone, genistein. In Cooper EL, Yamaguchi N (Eds.), Complementary and Alternative Approaches to Biomedicine. pp.121-165. Springer |
61 | Ren Q, Wang J, Liu S, Wang F, Wang H. 2017. Identification and determination of isoflavones in germinated black soybean sprouts by UHPLC−Q-TOF-MS mass spectrometry and HPLC-DAD. Int J Food Prop 20:2877-2887 DOI |