Metabolite profiling of isoflavones and anthocyanins in black soybean [Glycine max (L.) Merr.] seeds by HPLC-MS and geographical differentiation analysis in Southwest China

Wu, HengAn; Deng, Juzhi; Yang, Caiqiong; Zhang, Jing; Zhang, Qing; Wang, Xiaochun; Yang, Feng; Yang, Wenyu; Liu, Jiang

doi:10.1039/c6ay02970a

Cited by 31 publications

(26 citation statements)

References 30 publications

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“…In addition to isoflavones, a variety of flavonoids have been detected in soybeans, including anthocyanidin, kaempferol, and naringenin conjugates (Cavaliere et al., ; Ho et al., ; Shin et al., ; Wu et al., ). Black soybeans are known to contain anthocyanins such as cyanidin, delphinidin, peonidin, and petunidin glucosides, in addition to isoflavones (Shin et al., ; Wu et al., ). The isoflavones and anthocyanins in soybeans share some steps of the biosynthetic pathway of flavonoid (Ahmad, Li, Wang, Rehman, & Zhao, ).…”

Section: Discussionmentioning

confidence: 99%

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pH‐adjusted solvent extraction and reversed‐phase HPLC quantification of isoflavones from soybean (Glycine max (L.) Merr.)

Cho¹,

Jung

Nam

et al. 2020

Journal of Food Science

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Soybeans, Glycine max (L.) Merr., are among the most important food crops worldwide. Isoflavones are major bioactive phytochemicals in soybeans, and have a variety of health benefits, including antioxidative, antiatherosclerotic, antiinflammatory, and weak estrogen‐like effects. The isoflavone content and composition of soybeans vary according to the cultivar and the extraction solvent conditions. Therefore, we investigated the effects of three different solvent pHs (1.0, 5.5, and 10.0) on the isoflavone, total phenolic, and total flavonoid contents and antioxidant capacities of eight soybean cultivars developed in Korea. Twelve isoflavones in soybeans were efficiently separated and identified on a reversed‐phase high‐performance liquid chromatography (HPLC) system. The percentage distribution of isoflavones measured by HPLC in the eight soybean cultivars at various extraction pHs decreased as follows: malonyl isoflavones (67.2% to 81.3%) > isoflavone glucosides (16.2% to 29.0%; as nonacylated form) > acetyl isoflavones (1.6% to 5.9%). The highest contents of isoflavone glucosides, malonyl derivatives, and acetyl derivatives were extracted at solvent pHs of 10.0, 1.0, and 5.5, respectively. The solvent extraction at pH 1.0 yielded a lower total isoflavone content than those at pHs 5.5 and 10.0. However, the highest total phenolic and flavonoid contents were extracted from soybeans at pH 1.0. Soybeans extracted at pH 10.0 displayed the highest antioxidant capacities in the 2,2′‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) radical assay. Taken together, these results suggest that proper solvent pH adjustment is needed to maximize the extraction of targeted forms of isoflavones from soybeans. Practical Application Soybeans contain a variety of bioactive compounds, including isoflavones, which function as antioxidants and weak phytoestrogens. Chemical and instrumental analyses can facilitate the selection of soybean cultivars with high amounts of isoflavones for soybean breeding and isoflavone‐enriched product development. Proper solvent pH adjustment allows for the efficient extraction of high amounts of targeted isoflavone subgroups (acetyl and malonyl forms) from soybeans for functional food products.

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Section: Discussionmentioning

confidence: 99%

“…This discrepancy may be due to differences in the soybean cultivars and extraction methods. The isoflavone and anthocyanin contents of soybeans are known to be influenced by a variety of factors, including the cultivar, geographical location, and extraction method (Hong, Kim, Sohn, Kim, & Cho, ; Lin & Giusti, ; Wu et al., ).…”

Section: Discussionmentioning

confidence: 99%

pH‐adjusted solvent extraction and reversed‐phase HPLC quantification of isoflavones from soybean (Glycine max (L.) Merr.)

Cho¹,

Jung

Nam

et al. 2020

Journal of Food Science

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“…The compositions and contents of polyphenols in plants, in general, are affected by both environmental and genetic factors. Many researchers studied the effect of these factors on the contents of anthocyanins, isoflavones, and phenolic compounds in different soybean varieties including black soybeans [20][21][22][23][24] . Different studies have been targeting different components with respect to both number and identity, and hence, the reported total contents of these polyphenols are wide-ranging.…”

mentioning

confidence: 99%

Isoflavones, anthocyanins, phenolic content, and antioxidant activities of black soybeans (Glycine max (L.) Merrill) as affected by seed weight

Choi

Yoon

Lee

et al. 2020

Sci Rep

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Seed weight is regulated by several genes which in turn could affect the metabolite contents, yield, and quality of soybean seeds. Due to these, seed weight is receiving much attention in soybean breeding. In this study, seeds of 24 black soybean varieties and a reference genotype were grown in Korea, and grouped as small (< 13 g), medium (13–24 g), and large (> 24 g) seeds based on their seed weight. The contents of six anthocyanins, twelve isoflavones, and total phenolic, and the antioxidant activities were determined, and the association of each with seed weight was analyzed. The total anthocyanin (TAC) and total isoflavone (TIC) contents were in the ranges of 189.461–2633.454 mg/100 g and 2.110–5.777 mg/g, respectively and were significantly different among the black soybean varieties. By comparison, the average TAC and TIC were the highest in large seeds than in small and medium seeds while the total phenolic content (TPC) was in the order of small seeds > large seeds > medium seeds. Besides, large seeds showed the maximum 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging activity, whereas small seeds showed the maximum ferric reducing antioxidant power (FRAP) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical (ABTS) scavenging activities. FRAP activity was positively associated with TIC and TAC, the former association being significant. On the other hand, ABTS and DPPH activities were positively correlated to TPC, the later association being significant. Overall, our findings demonstrated the influence of seed weight on anthocyanin, isoflavone, and phenolic contents and antioxidant activities in black soybeans. Besides, the dominant anthocyanins and isoflavones were the principal contributors to the variations observed in the black soybean varieties, and hence, these components could be selectively targeted to discriminate a large population of black soybean genetic resources.

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“…Isoflavon utama dalam bentuk glikosida berupa genistin dan daidzin (Teekachunhatean et al 2013). Pada kedelai hitam, daidzein, genistein, glisitein, dan daidzin adalah isoflavon utama yang menunjukkan aktivitas sebagai agen pencegah pada beberapa penyakit kronis (Wu et al 2017;Ren et al 2016).…”

Section: Pendahuluanunclassified

Perbandingan Kandungan Genistein Pada Berbagai Varietas Kedelai (Glycine max) Di Indonesia

Hasanah¹,

Sukrasno²,

Hartati³

2020

j. penelit. pertan. tanam. pangan

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Soybeans is a functional food, containing higher isoflavone compared to that of other food crops. Genistein, daidzein and glisitein are components of soybean isoflavones. Genistein to function as a protective agent against cancer and cardiovascular diseases. The content of genistein in soybean can be influenced by soybean varieties and plant maturities. This study was aimed to determine the genistein content of soybean varieties in Indonesia. The experiment was carried out at Biology Pharmacy

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Metabolite profiling of isoflavones and anthocyanins in black soybean [Glycine max (L.) Merr.] seeds by HPLC-MS and geographical differentiation analysis in Southwest China

Abstract: Twelve isoflavones and eight anthocyanins were quantified in black soybean seeds by HPLC-MS analyses; the coupled OPLS-DA multivariate statistical analysis helped us to determine their geographical origin.

Cited by 31 publications

References 30 publications

pH‐adjusted solvent extraction and reversed‐phase HPLC quantification of isoflavones from soybean (Glycine max (L.) Merr.)

pH‐adjusted solvent extraction and reversed‐phase HPLC quantification of isoflavones from soybean (Glycine max (L.) Merr.)

Isoflavones, anthocyanins, phenolic content, and antioxidant activities of black soybeans (Glycine max (L.) Merrill) as affected by seed weight

Perbandingan Kandungan Genistein Pada Berbagai Varietas Kedelai (Glycine max) Di Indonesia

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