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Murakami A. Looking back at the achievements of functional food science in Japan. Biosci Biotechnol Biochem 2025; 89:147-151. [PMID: 39322268 DOI: 10.1093/bbb/zbae134] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/29/2024] [Accepted: 09/13/2024] [Indexed: 09/27/2024]
Abstract
Functional food science in Japan actively began approximately 40 years ago in the form of specific research projects funded by Grants-in-Aids for Scientific Research from the Ministry of Education, Science and Culture. Then, a new category of healthy food, that is "Food for Specified Health Use" (FOSHU), was established. Toshihiko Osawa organized and held the First International Conference on Food Factors in Hamamatsu, Japan, in 1995. As examples of key achievements in basic science, the chemical identification of numerous active principles in foods, elucidation of their metabolism pathways, and mechanistic findings using "omics" technologies and the discovery of target molecules are remarkable. However, whether FOSHU truly contributes to public health is still unknown. In this minireview, the author looks back on functional food science in Japan to date and, at the same time, describes the prospects to share a vision of the future in the next 10 years.
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Affiliation(s)
- Akira Murakami
- Department of Food Science and Nutrition, School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan
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Wu PS, Wang CY, Hsu HJ, Yen JH, Wu MJ. 8-Hydroxydaidzein Induces Apoptosis and Inhibits AML-Associated Gene Expression in U-937 Cells: Potential Phytochemical for AML Treatment. Biomolecules 2023; 13:1575. [PMID: 38002257 PMCID: PMC10669020 DOI: 10.3390/biom13111575] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/10/2023] [Revised: 09/30/2023] [Accepted: 10/19/2023] [Indexed: 11/26/2023] Open
Abstract
BACKGROUND 8-hydroxydaidzein (8-OHD) is a compound derived from daidzein, known for its anti-inflammatory and anti-proliferative properties in K562 human chronic myeloid leukemia (CML) cells. However, its effects on acute myeloid leukemia (AML) cells have not been fully understood. METHOD To investigate its potential anti-AML mechanism, we employed an integrated in vitro-in silico approach. RESULTS Our findings demonstrate that 8-OHD suppresses the expression of CDK6 and CCND2 proteins and induces cell apoptosis in U-937 cells by activating Caspase-7 and cleaving PARP-1. Microarray analysis revealed that 8-OHD downregulates differentially expressed genes (DEGs) associated with rRNA processing and ribosome biogenesis pathways. Moreover, AML-target genes, including CCND2, MYC, NPM1, FLT3, and TERT, were downregulated by 8-OHD. Additionally, molecular docking software predicted that 8-OHD has the potential to interact with CDK6, FLT3, and TERT proteins, thereby reducing their activity and inhibiting cell proliferation. Notably, we discovered a synergic pharmacological interaction between 8-OHD and cytarabine (Ara-C). CONCLUSIONS Overall, this study provides insights into the therapeutic applications of 8-OHD in treating AML and elucidates its underlying mechanisms of action.
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Affiliation(s)
- Pei-Shan Wu
- Department of Pharmacy, Chia Nan University of Pharmacy and Science, Tainan 717301, Taiwan;
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 717301, Taiwan
| | - Chih-Yang Wang
- Ph.D. Program for Cancer Molecular Biology and Drug Discovery, Taipei Medical University, Taipei 110301, Taiwan;
- Graduate Institute of Cancer Biology and Drug Discovery, Taipei Medical University, Taipei 110301, Taiwan
| | - Hao-Jen Hsu
- Department of Biomedical Sciences and Engineering, Tzu Chi University, Hualien 970, Taiwan;
| | - Jui-Hung Yen
- Department of Molecular Biology and Human Genetics, Tzu Chi University, Hualien 970374, Taiwan;
- Institute of Medical Sciences, Tzu Chi University, Hualien 970374, Taiwan
| | - Ming-Jiuan Wu
- Department of Pharmacy, Chia Nan University of Pharmacy and Science, Tainan 717301, Taiwan;
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 717301, Taiwan
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Soy Extract, Rich in Hydroxylated Isoflavones, Exhibits Antidiabetic Properties In Vitro and in Drosophila melanogaster In Vivo. Nutrients 2023; 15:nu15061392. [PMID: 36986122 PMCID: PMC10054920 DOI: 10.3390/nu15061392] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/10/2023] [Revised: 03/03/2023] [Accepted: 03/07/2023] [Indexed: 03/15/2023] Open
Abstract
In the context of the growing prevalence of type 2 diabetes (T2DM), control of postprandial hyperglycemia is crucial for its prevention. Blood glucose levels are determined by various factors including carbohydrate hydrolyzing enzymes, the incretin system and glucose transporters. Furthermore, inflammatory markers are recognized predictors of diabetes outcome. Although there is some evidence that isoflavones may exhibit anti-diabetic properties, little is known about to what extent their corresponding hydroxylated metabolites may affect glucose metabolism. We evaluated the ability of a soy extract before (pre-) and after (post-) fermentation to counteract hyperglycemia in vitro and in Drosophila melanogaster in vivo. Fermentation with Aspergillus sp. JCM22299 led to an enrichment of hydroxy-isoflavones (HI), including 8-hydroxygenistein, 8-hydroxyglycitein and 8-hydroxydaidzein, accompanied by an enhanced free radical scavenging activity. This HI-rich extract demonstrated inhibitory activity towards α-glucosidase and a reduction of dipeptidyl peptidase-4 enzyme activity. Both the pre- and post-fermented extracts significantly inhibited the glucose transport via sodium-dependent glucose transporter 1. Furthermore, the soy extracts reduced c-reactive protein mRNA and secreted protein levels in interleukin-stimulated Hep B3 cells. Finally, supplementation of a high-starch D. melanogaster diet with post-fermented HI-rich extract decreased the triacylglyceride content of female fruit flies, confirming its anti-diabetic properties in an in vivo model.
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Messina M, Duncan A, Messina V, Lynch H, Kiel J, Erdman JW. The health effects of soy: A reference guide for health professionals. Front Nutr 2022; 9:970364. [PMID: 36034914 PMCID: PMC9410752 DOI: 10.3389/fnut.2022.970364] [Citation(s) in RCA: 17] [Impact Index Per Article: 5.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/15/2022] [Accepted: 07/25/2022] [Indexed: 11/22/2022] Open
Abstract
Soy is a hotly debated and widely discussed topic in the field of nutrition. However, health practitioners may be ill-equipped to counsel clients and patients about the use of soyfoods because of the enormous, and often contradictory, amount of research that has been published over the past 30 years. As interest in plant-based diets increases, there will be increased pressure for practitioners to gain a working knowledge of this area. The purpose of this review is to provide concise literature summaries (400-500 words) along with a short perspective on the current state of knowledge of a wide range of topics related to soy, from the cholesterol-lowering effects of soy protein to the impact of isoflavones on breast cancer risk. In addition to the literature summaries, general background information on soyfoods, soy protein, and isoflavones is provided. This analysis can serve as a tool for health professionals to be used when discussing soyfoods with their clients and patients.
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Affiliation(s)
- Mark Messina
- Soy Nutrition Institute Global, Washington, DC, United States
| | - Alison Duncan
- Department of Human Health and Nutritional Sciences, University of Guelph, Guelph, ON, Canada
| | | | - Heidi Lynch
- Kinesiology Department, Point Loma Nazarene University, San Diego, CA, United States
| | - Jessica Kiel
- Scientific and Clinical Affairs, Medifast Inc., Baltimore, MD, United States
| | - John W. Erdman
- Division of Nutritional Sciences and Beckman Institute, Department of Food Science and Human Nutrition, University of Illinois at Urbana/Champaign, Urbana, IL, United States
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Taniguchi R, Ito C, Keitoku S, Miyake Y, Itoigawa M, Matsui T, Shibata T. Analysis on the Structure of Phlorethols Isolated From the Warm-Temperate Brown Seaweed Sargassum carpophyllum and Their Antioxidant Properties. Nat Prod Commun 2022. [DOI: 10.1177/1934578x221109406] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/15/2022] Open
Abstract
The brown seaweed Sargassum carpophyllum J. Agardh is an unused warm-temperate species in the family Sargassaceae that has been expanding its distribution along the coastal areas of Japan in recent years. In this study, 3 types of phlorotannins were identified from the EtOAc fraction of the 80% MeOH extract of S. carpophyllum. From the spectroscopic (1H NMR, 13C NMR, and HMBC) and ESI/MS data and comparison with those of prior literature, it was demonstrated that the compounds are oligomers of phlorethol, which is one of the subclasses of phlorotannins, that is triphlorethol B (phloroglucinol trimer), tetraphlorethol C (phloroglucinol tetramer), and pentaphlorethol A (phloroglucinol pentamer). Among the phlorethols, tetraphlorethol C and pentaphlorethol A were isolated and identified for the first time from a brown seaweed collected from the East China Sea, including the coastal areas of Japan. The identified phlorethols were tested for their antioxidant properties. In the antioxidant assay using liposomes, the phlorethols showed comparable inhibitory effects to epigallocatechin gallate (tea polyphenol) and α-tocopherol (liposoluble vitamin) on lipid peroxidation by 4 mM 2,2′-azobis(2-methylpropionamidine) dihydrochloride. In addition, it was revealed that pentaphlorethol A has a superoxide anion scavenging activity (50% effective concentration: 21 μM) higher than that (50% effective concentration: 46 μM) of ascorbic acid (hydrosoluble vitamin).
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Affiliation(s)
| | - Chihiro Ito
- Faculty of Pharmacy, Meijo University, Nagoya, Japan
| | - Saki Keitoku
- Graduate School of Bioresources, Mie University, Tsu, Mie, Japan
| | - Yoshiaki Miyake
- Faculty of Health and Medical Sciences, Aichi Shukutoku University, Nagakute, Aichi, Japan
| | - Masataka Itoigawa
- School of Sport and Health Science, Tokai Gakuen University, Miyoshi, Aichi, Japan
| | - Takuya Matsui
- Department of Physiology, School of Medicine, Aichi Medical University, Nagakute, Aichi, Japan
| | - Toshiyuki Shibata
- Graduate School of Bioresources, Mie University, Tsu, Mie, Japan
- Seaweed Biorefinery Research Center, Mie University, Tsu, Mie, Japan
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Wu PS, Wang CY, Chen PS, Hung JH, Yen JH, Wu MJ. 8-Hydroxydaidzein Downregulates JAK/STAT, MMP, Oxidative Phosphorylation, and PI3K/AKT Pathways in K562 Cells. Biomedicines 2021; 9:biomedicines9121907. [PMID: 34944720 PMCID: PMC8698423 DOI: 10.3390/biomedicines9121907] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/08/2021] [Revised: 12/05/2021] [Accepted: 12/10/2021] [Indexed: 12/12/2022] Open
Abstract
A metabolite isolated from fermented soybean, 8-hydroxydaidzein (8-OHD, 7,8,4′-trihydroxyisoflavone, NSC-678112), is widely used in ethnopharmacological research due to its anti-proliferative and anti-inflammatory effects. We reported previously that 8-OHD provoked reactive oxygen species (ROS) overproduction, and induced autophagy, apoptosis, breakpoint cluster region-Abelson murine leukemia viral oncogene (BCR-ABL) degradation, and differentiation in K562 human chronic myeloid leukemia (CML) cells. However, how 8-OHD regulates metabolism, the extracellular matrix during invasion and metastasis, and survival signaling pathways in CML remains largely unexplored. High-throughput technologies have been widely used to discover the therapeutic targets and pathways of drugs. Bioinformatics analysis of 8-OHD-downregulated differentially expressed genes (DEGs) revealed that Janus kinase/signal transducer and activator of transcription (JAK/STAT), matrix metalloproteinases (MMPs), c-Myc, phosphoinositide 3-kinase (PI3K)/AKT, and oxidative phosphorylation (OXPHOS) metabolic pathways were significantly altered by 8-OHD treatment. Western blot analyses validated that 8-OHD significantly downregulated cytosolic JAK2 and the expression and phosphorylation of STAT3 dose- and time-dependently in K562 cells. Zymography and transwell assays also confirmed that K562-secreted MMP9 and invasion activities were dose-dependently inhibited by 8-OHD after 24 h of treatment. RT-qPCR analyses verified that 8-OHD repressed metastasis and OXPHOS-related genes. In combination with DisGeNET, it was found that 8-OHD’s downregulation of PI3K/AKT is crucial for controlling CML development. A STRING protein–protein interaction analysis further revealed that AKT and MYC are hub proteins for cancer progression. Western blotting revealed that AKT phosphorylation and nuclear MYC expression were significantly inhibited by 8-OHD. Collectively, this systematic investigation revealed that 8-OHD exerts anti-CML effects by downregulating JAK/STAT, PI3K/AKT, MMP, and OXPHOS pathways, and MYC expression. These results could shed new light on the development of 8-OHD for CML therapy.
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Affiliation(s)
- Pei-Shan Wu
- Department of Applied Life Science and Health, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan; (P.-S.W.); (P.-S.C.)
| | - Chih-Yang Wang
- Ph.D. Program for Cancer Molecular Biology and Drug Discovery, Taipei Medical University, Taipei 11031, Taiwan;
- Graduate Institute of Cancer Biology and Drug Discovery, Taipei Medical University, Taipei 11031, Taiwan
| | - Pin-Shern Chen
- Department of Applied Life Science and Health, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan; (P.-S.W.); (P.-S.C.)
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan;
| | - Jui-Hsiang Hung
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan;
| | - Jui-Hung Yen
- Department of Molecular Biology and Human Genetics, Tzu Chi University, Hualien 970, Taiwan;
- Institute of Medical Sciences, Tzu Chi University, Hualien 970, Taiwan
| | - Ming-Jiuan Wu
- Department of Applied Life Science and Health, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan; (P.-S.W.); (P.-S.C.)
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan;
- Correspondence: or ; Tel.: +886-6-2664911 (ext. 2520)
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A new sight on soy isoflavones during the whole soy sauce fermentation process by UPLC-MS/MS. Lebensm Wiss Technol 2021. [DOI: 10.1016/j.lwt.2021.112249] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/07/2023]
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Biotransformation of Daidzein, Genistein, and Naringenin by Streptomyces Species Isolated from High-Altitude Soil of Nepal. Int J Microbiol 2021; 2021:9948738. [PMID: 34249126 PMCID: PMC8238566 DOI: 10.1155/2021/9948738] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/29/2021] [Revised: 05/04/2021] [Accepted: 06/14/2021] [Indexed: 11/18/2022] Open
Abstract
Flavonoids have achieved widespread importance in pharmaceutical, food, and cosmetics industries. Furthermore, modification of these naturally occurring flavonoids to structurally diverse compounds through whole cell biotransformation with enhanced biological activities has numerous biotechnological applications. The present study investigated the biotransformation potential of Streptomyces species isolated from a high-altitude-soil sample towards selected flavonoid molecules. The biotransformed metabolites were confirmed by comparing the HPLC chromatogram with authentic compounds and LC-MS/MS analysis. Of these isolates, Streptomyces species G-18 (Accession number: MW663767.1) catalyzed isoflavone molecules daidzein and genistein to produce hydroxylated products at 24 h of reaction condition in a whole cell system. The hydroxylation of daidzein (4′,7-dihydroxyisoflavone) was confirmed at 3′-position of the B ring to produce 3′,4′,7-trihydroxyisoflavone. In addition, Streptomyces species G-14 (Accession number: MW663770.1) and Streptomyces species S4L (Accession number: MW663769.1) also revealed the transformation of daidzein (4′,7-dihydroxyisoflavone) to hydroxy daidzein at a distinct position than that of G-18 isolates, whereas thee Streptomyces species S4L reaction mixture with naringenin as a substrate also revealed the hydroxylated product. Our results demonstrated that microorganisms isolated from different ecological niches have broad application.
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Westrick NM, Smith DL, Kabbage M. Disarming the Host: Detoxification of Plant Defense Compounds During Fungal Necrotrophy. FRONTIERS IN PLANT SCIENCE 2021; 12:651716. [PMID: 33995447 PMCID: PMC8120277 DOI: 10.3389/fpls.2021.651716] [Citation(s) in RCA: 24] [Impact Index Per Article: 6.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 01/10/2021] [Accepted: 03/26/2021] [Indexed: 05/02/2023]
Abstract
While fungal biotrophs are dependent on successfully suppressing/subverting host defenses during their interaction with live cells, necrotrophs, due to their lifestyle are often confronted with a suite of toxic metabolites. These include an assortment of plant defense compounds (PDCs) which can demonstrate broad antifungal activity. These PDCs can be either constitutively present in plant tissue or induced in response to infection, but are nevertheless an important obstacle which needs to be overcome for successful pathogenesis. Fungal necrotrophs have developed a number of strategies to achieve this goal, from the direct detoxification of these compounds through enzymatic catalysis and modification, to the active transport of various PDCs to achieve toxin sequestration and efflux. Studies have shown across multiple pathogens that the efficient detoxification of host PDCs is both critical for successful infection and often a determinant factor in pathogen host range. Here, we provide a broad and comparative overview of the various mechanisms for PDC detoxification which have been identified in both fungal necrotrophs and fungal pathogens which depend on detoxification during a necrotrophic phase of infection. Furthermore, the effect that these mechanisms have on fungal host range, metabolism, and disease control will be discussed.
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Wu PS, Yen JH, Wang CY, Chen PY, Hung JH, Wu MJ. 8-Hydroxydaidzein, an Isoflavone from Fermented Soybean, Induces Autophagy, Apoptosis, Differentiation, and Degradation of Oncoprotein BCR-ABL in K562 Cells. Biomedicines 2020; 8:E506. [PMID: 33207739 PMCID: PMC7696406 DOI: 10.3390/biomedicines8110506] [Citation(s) in RCA: 15] [Impact Index Per Article: 3.0] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/29/2020] [Revised: 11/12/2020] [Accepted: 11/13/2020] [Indexed: 12/22/2022] Open
Abstract
8-Hydroxydaidzein (8-OHD, 7,8,4'-trihydoxyisoflavone) is a hydroxylated derivative of daidzein isolated from fermented soybean products. The aim of this study is to investigate the anti-proliferative effects and the underlying mechanisms of 8-OHD in K562 human chronic myeloid leukemia (CML) cells. We found that 8-OHD induced reactive oxygen species (ROS) overproduction and cell cycle arrest at the S phase by upregulating p21Cip1 and downregulating cyclin D2 (CCND2) and cyclin-dependent kinase 6 (CDK6) expression. 8-OHD also induced autophagy, caspase-7-dependent apoptosis, and the degradation of BCR-ABL oncoprotein. 8-OHD promoted Early Growth Response 1 (EGR1)-mediated megakaryocytic differentiation as an increased expression of marker genes, CD61 and CD42b, and the formation of multi-lobulated nuclei in enlarged K562 cells. A microarray-based transcriptome analysis revealed a total of 3174 differentially expressed genes (DEGs) after 8-OHD (100 μM) treatment for 48 h. Bioinformatics analysis of DEGs showed that hemopoiesis, cell cycle regulation, nuclear factor-κB (NF-κB), and mitogen-activated protein kinase (MAPK) and Janus kinase/signal transducers and activators of transcription (JAK-STAT)-mediated apoptosis/anti-apoptosis networks were significantly regulated by 8-OHD. Western blot analysis confirmed that 8-OHD significantly induced the activation of MAPK and NF-κB signaling pathways, both of which may be responsible, at least in part, for the stimulation of apoptosis, autophagy, and differentiation in K562 cells. This is the first report on the anti-CML effects of 8-OHD and the combination of experimental and in silico analyses could provide a better understanding for the development of 8-OHD on CML therapy.
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Affiliation(s)
- Pei-Shan Wu
- Department of Pharmacy, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan;
| | - Jui-Hung Yen
- Department of Molecular Biology and Human Genetics, Tzu Chi University, Hualien 970, Taiwan; (J.-H.Y.); (P.-Y.C.)
- Institute of Medical Sciences, Tzu Chi University, Hualien 970, Taiwan
| | - Chih-Yang Wang
- Ph.D. Program for Cancer Molecular Biology and Drug Discovery, Taipei Medical University, Taipei 11031, Taiwan;
- Graduate Institute of Cancer Biology and Drug Discovery, Taipei Medical University, Taipei 11031, Taiwan
| | - Pei-Yi Chen
- Department of Molecular Biology and Human Genetics, Tzu Chi University, Hualien 970, Taiwan; (J.-H.Y.); (P.-Y.C.)
- Center of Medical Genetics, Buddhist Tzu Chi General Hospital, Hualien 970, Taiwan
| | - Jui-Hsiang Hung
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan;
| | - Ming-Jiuan Wu
- Department of Pharmacy, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan;
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Chang TS, Wang TY, Yang SY, Kao YH, Wu JY, Chiang CM. Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of Deinococcus geothermalis. Molecules 2019; 24:molecules24122236. [PMID: 31208027 PMCID: PMC6631725 DOI: 10.3390/molecules24122236] [Citation(s) in RCA: 24] [Impact Index Per Article: 4.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/30/2019] [Revised: 06/09/2019] [Accepted: 06/14/2019] [Indexed: 12/31/2022] Open
Abstract
8-Hydroxydaidzein (8-OHDe), an ortho-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of Deinococcus geothermalis (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC50 value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future.
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Affiliation(s)
- Te-Sheng Chang
- Department of Biological Sciences and Technology, National University of Tainan, Tainan 70005, Taiwan.
| | - Tzi-Yuan Wang
- Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan.
| | - Szu-Yi Yang
- Department of Biological Sciences and Technology, National University of Tainan, Tainan 70005, Taiwan.
| | - Yu-Han Kao
- Department of Biological Sciences and Technology, National University of Tainan, Tainan 70005, Taiwan.
| | - Jiumn-Yih Wu
- Department of Food Science, National Quemoy University, Kinmen County 892, Taiwan.
| | - Chien-Min Chiang
- Department of Biotechnology, Chia Nan University of Pharmacy and Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan.
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Lee PG, Lee UJ, Song H, Choi KY, Kim BG. Recent advances in the microbial hydroxylation and reduction of soy isoflavones. FEMS Microbiol Lett 2018; 365:5089968. [PMID: 30184116 DOI: 10.1093/femsle/fny195] [Citation(s) in RCA: 10] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/15/2018] [Accepted: 08/31/2018] [Indexed: 12/17/2023] Open
Abstract
Soy isoflavones are naturally occurring phytochemicals, which are biotransformed into functional derivatives through oxidative and reductive metabolic pathways of diverse microorganisms. Such representative derivatives, ortho-dihydroxyisoflavones (ODIs) and equols, have attracted great attention for their versatile health benefits since they were found from soybean fermented foods and human intestinal fluids. Recently, scientists in food technology, nutrition and microbiology began to understand their correct biosynthetic pathways and nutraceutical values, and have attempted to produce the valuable bioactive compounds using microbial fermentation and whole-cell/enzyme-based biotransformation. Furthermore, artificial design of microbial catalysts and/or protein engineering of oxidoreductases were also conducted to enhance production efficiency and regioselectivity of products. This minireview summarizes and introduces the past year's studies and recent advances in notable production of ODIs and equols, and provides information on available microbial species and their catalytic performance with perspectives on industrial application.
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Affiliation(s)
- Pyung-Gang Lee
- School of Chemical and Biological Engineering, Seoul National University, Seoul 08826, Republic of Korea
- Institute of Molecular Biology and Genetics, Seoul National University, Seoul 08826, Republic of Korea
| | - Uk-Jae Lee
- School of Chemical and Biological Engineering, Seoul National University, Seoul 08826, Republic of Korea
- Institute of Molecular Biology and Genetics, Seoul National University, Seoul 08826, Republic of Korea
| | - Hanbit Song
- School of Chemical and Biological Engineering, Seoul National University, Seoul 08826, Republic of Korea
- Institute of Molecular Biology and Genetics, Seoul National University, Seoul 08826, Republic of Korea
| | - Kwon-Young Choi
- Department of Environmental Engineering, College of Engineering, Ajou University, Suwon 16499, Republic of Korea
| | - Byung-Gee Kim
- School of Chemical and Biological Engineering, Seoul National University, Seoul 08826, Republic of Korea
- Institute of Molecular Biology and Genetics, Seoul National University, Seoul 08826, Republic of Korea
- Bioengineering Institute, Seoul National University, Seoul 08826, South Korea
- Institute of Bioengineering Research, Seoul National University, Seoul 08826, Republic of Korea
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Wu PS, Ding HY, Yen JH, Chen SF, Lee KH, Wu MJ. Anti-inflammatory Activity of 8-Hydroxydaidzein in LPS-Stimulated BV2 Microglial Cells via Activation of Nrf2-Antioxidant and Attenuation of Akt/NF-κB-Inflammatory Signaling Pathways, as Well As Inhibition of COX-2 Activity. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2018; 66:5790-5801. [PMID: 29790749 DOI: 10.1021/acs.jafc.8b00437] [Citation(s) in RCA: 41] [Impact Index Per Article: 5.9] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/08/2023]
Abstract
It was demonstrated that isoflavones can cross the blood-brain barrier, making them desirable candidate agents for the prevention of neurological symptoms. 8-Hydroxydaidzein (8-OHD, 4',7,8-trihydoxyisoflavone) is an isoflavone found only in fermented soy food. Current results showed that 8-OHD inhibited LPS-stimulated production of nitric oxide (NO) and proinflammatory cytokines, such as tumor necrosis factor (TNF)-α and interleukin (IL)-6, by inhibiting gene expression in BV2 microglial cells. Moreover, 8-OHD markedly quenched reactive oxygen species (ROS) and activated NF-E2-related factor 2 (Nrf2) so as to upregulate expression of Phase II enzymes, including heme oxygenase (HO)-1, NAD(P)H quinone dehydrogenase 1 (NQO1), and the modifier subunit of glutamate cysteine ligase (GCLM). 8-OHD also suppressed LPS-stimulated phosphorylation of Akt and NF-κB-p65. The anti-inflammatory activity of 8-OHD was attenuated by the HO-1 inhibitor zinc protoporphyrin (Znpp) but augmented by the PI3K/Akt inhibitor LY294002. 8-OHD also diminished LPS-induced prostaglandin E2 (PGE2) production without affecting cyclooxygenase (COX)-2 expression. In vitro assay shows that 8-OHD displayed mixed-type inhibition of COX-2 with an IC50 of 8.9 ± 1.2 μM. These data suggest that the anti-inflammatory activity of 8-OHD may be associated with the activation of Nrf2/HO-1 and attenuation of Akt/NF-κB signaling pathways as well as inhibition of COX-2 enzyme activity. In conclusion, 8-OHD, a potent Nrf2 activator, Akt/NF-κB activation suppressor, and COX-2 enzyme inhibitor, may have health-promoting effects for mitigating microglia activation and preventing neuroinflammation.
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Affiliation(s)
| | | | - Jui-Hung Yen
- Department of Molecular Biology and Human Genetics , Tzu Chi University , Hualien 970 , Taiwan
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14
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Lee CC, Dudonné S, Kim JH, Kim JS, Dubé P, Kim JE, Desjardins Y, Park JHY, Lee KW, Lee CY. A major daidzin metabolite 7,8,4'-trihydroxyisoflavone found in the plasma of soybean extract-fed rats attenuates monocyte-endothelial cell adhesion. Food Chem 2018; 240:607-614. [PMID: 28946319 DOI: 10.1016/j.foodchem.2017.08.002] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/16/2017] [Revised: 06/30/2017] [Accepted: 08/01/2017] [Indexed: 11/20/2022]
Abstract
Among many functional foods and their phytochemicals, ingestion of soybean (Glycine max) is highly correlated to reduced risk of cardiovascular diseases. Validation of potential health benefits of functional foods requires information about the bioavailability and metabolism of bioactive compounds. In this context, several phase I and II metabolites of isoflavones were target-analyzed in the plasma of rats acutely supplemented with soybean embryo extract. A daidzein metabolite, 7,8,4'-trihydroxyisoflavone (7,8,4'-THI), was found to have the highest average area under curve value (574.3±112.8). Therefore, its potential prevention effect on atherosclerosis was investigated using monocyte-endothelial cell adhesion assay. Different from its precursor daidzein or daidzin, 7,8,4'-THI attenuated adhesion of THP-1 monocytes to tumor necrosis factor-alpha (TNF-α) stimulated human umbilical vein endothelial cells (HUVECs). In addition, 7,8,4'-THI significantly downregulated TNF-α stimulated the expression of vascular cell adhesion molecule-1 and monocyte chemotactic protein-1 and phosphorylation of IκB kinase and IκBα involved in the initiation of atherosclerosis in HUVECs. Therefore, 7,8,4'-THI, a highly bioavailable hydroxylated isoflavone metabolite, has potential anti-atherosclerotic effect via inhibiting monocyte-endothelial adhesion.
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Affiliation(s)
- Charles C Lee
- Department of Food Science, Cornell University, Ithaca, NY 14853, USA.
| | - Stéphanie Dudonné
- Institute of Nutrition and Functional Foods (INAF), Laval University, 2440 Boulevard Hochelaga, Québec, QC G1V0A6, Canada.
| | - Jong Hun Kim
- Research Institute of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Republic of Korea; Advanced Institutes of Convergence Technology, Seoul National University, Suwon 16229, Republic of Korea.
| | - Ji Seung Kim
- Major in Biomodulation, Department of Agricultural Biotechnology, Seoul National University, Seoul 08826, Republic of Korea.
| | - Pascal Dubé
- Institute of Nutrition and Functional Foods (INAF), Laval University, 2440 Boulevard Hochelaga, Québec, QC G1V0A6, Canada.
| | - Jong-Eun Kim
- Research Institute of Biotechnology and Medical Converged Science, Dongguk University-Seoul, Goyang 10326, Republic of Korea.
| | - Yves Desjardins
- Institute of Nutrition and Functional Foods (INAF), Laval University, 2440 Boulevard Hochelaga, Québec, QC G1V0A6, Canada.
| | - Jung Han Yoon Park
- Research Institute of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Republic of Korea; Advanced Institutes of Convergence Technology, Seoul National University, Suwon 16229, Republic of Korea.
| | - Ki Won Lee
- Research Institute of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Republic of Korea; Advanced Institutes of Convergence Technology, Seoul National University, Suwon 16229, Republic of Korea; Major in Biomodulation, Department of Agricultural Biotechnology, Seoul National University, Seoul 08826, Republic of Korea.
| | - Chang Yong Lee
- Department of Food Science, Cornell University, Ithaca, NY 14853, USA.
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15
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Ye H, Dudley SZ, Shaw IC. Escherichia colibiotransformation of daidzein fermentation products from soy-based foods-relevance to food oestrogenicity-based functionality. Int J Food Sci Technol 2017. [DOI: 10.1111/ijfs.13410] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
Affiliation(s)
- Hui Ye
- Human Toxicology Research Group, Department of Chemistry; University of Canterbury; Christchurch New Zealand
| | - Samantha Z. Dudley
- Human Toxicology Research Group, Department of Chemistry; University of Canterbury; Christchurch New Zealand
| | - Ian C. Shaw
- Human Toxicology Research Group, Department of Chemistry; University of Canterbury; Christchurch New Zealand
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16
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Wu SC, Chang CW. Production of 8-Hydroxygenistein through Biotransformation by UsingAspergillus oryzae. CHEM ENG COMMUN 2016. [DOI: 10.1080/00986445.2016.1147030] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/09/2023]
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17
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Maeda S, Kazama Y, Kobayashi A, Yamazaki A, Nakamura S, Yamaguchi M, Maeda H, Ohtsubo K. Improvement of Palatability and Prevention of Abrupt Increases in Postprandial Blood Glucose Levels by Hokurikukona243 after High Pressure Treatment. J Appl Glycosci (1999) 2015. [DOI: 10.5458/jag.jag.jag-2015_013] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/23/2022] Open
Affiliation(s)
- Satoshi Maeda
- Echigo Seika Co., Ltd
- Faculty of Agriculture, Niigata University
| | | | | | | | | | - Masayuki Yamaguchi
- Institute of Crop Science, National Agriculture and Food Research Organization
| | - Hideo Maeda
- Agricultural Research Center, National Agriculture and Food Research Organization
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18
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Mohammadi Sartang M, Mazloomi SM, Tanideh N, Rezaian Zadeh A. The Effects of Probiotic Soymilk Fortified with Omega-3 on Blood Glucose, Lipid Profile, Haematological and Oxidative Stress, and Inflammatory Parameters in Streptozotocin Nicotinamide-Induced Diabetic Rats. J Diabetes Res 2015; 2015:696372. [PMID: 26347893 PMCID: PMC4548139 DOI: 10.1155/2015/696372] [Citation(s) in RCA: 19] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 01/02/2015] [Accepted: 03/10/2015] [Indexed: 01/03/2023] Open
Abstract
OBJECTIVE The aim of the present study was to evaluate the effects of probiotic soymilk fortified with omega-3 in diabetic rats. METHODS Soymilk (SM), fermented soymilk (FSM), and fermented soymilk fortified with omega-3 (FSM + omega-3) were prepared. Rats were randomly assigned to five groups of 13 animals per group. Diabetes was induced by a single injection of streptozotocin (STZ) 15 min after the intraperitoneal administration of nicotinamide (NA). Normal control (NC) and diabetic control (DC) rats received 1 mL/day of distilled water and three groups of diabetic rats were given 1 mL/day of SM, FSM, and FSM + omega-3 products by oral gavage for 28 days. RESULTS Three products significantly (P < 0.05) reduced blood glucose, total cholesterol (TC), triglyceride (TG), and malondialdehyde (MDA) concentrations compared to the DC group, with the maximum reduction seen in the FSM + omega-3 group. Body weight, red blood cells (RBC), haemoglobin (Hb), haematocrit, and superoxide dismutase (SOD) also significantly increased in the FSM + omega-3 group. In the FSM + omega-3 group, MDA level compared with the SM and FSM groups and high sensitivity C-reactive protein (hs-CRP) concentrations compared with the DC and FSM groups were significantly lower (P < 0.05). CONCLUSION Fermented soymilk fortified with omega-3 may be beneficial in diabetes.
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Affiliation(s)
- Mohsen Mohammadi Sartang
- Student Research Committee, School of Nutrition and Food Sciences, Shiraz University of Medical Sciences, Shiraz 7153675541, Iran
| | - Seyed Mohammad Mazloomi
- Department of Food Hygiene and Quality Control, Nutrition and Food Sciences Research Center, School of Nutrition and Food Sciences, Shiraz University of Medical Sciences, Shiraz 7153675541, Iran
- *Seyed Mohammad Mazloomi:
| | - Nader Tanideh
- Stem Cell and Transgenic Technology Research Center, Department of Pharmacology, School of Medicine, Shiraz University of Medical Sciences, Shiraz 7134874478, Iran
| | - Abbas Rezaian Zadeh
- Research Center for Health Sciences, Department of Epidemiology, School of Health, Shiraz University of Medical Sciences, Shiraz 7153675541, Iran
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19
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Wu SC, Chang CW, Lin CW, Hsu YC. Production of 8-hydroxydaidzein Polyphenol Using Biotransformation by Aspergillus oryzae. FOOD SCIENCE AND TECHNOLOGY RESEARCH 2015. [DOI: 10.3136/fstr.21.557] [Citation(s) in RCA: 10] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 11/03/2022]
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20
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Sheih IC, Fang TJ, Wu TK, Chen RY. Effects of fermentation on antioxidant properties and phytochemical composition of soy germ. JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE 2014; 94:3163-70. [PMID: 24652711 DOI: 10.1002/jsfa.6666] [Citation(s) in RCA: 15] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 11/04/2013] [Revised: 02/16/2014] [Accepted: 03/15/2014] [Indexed: 06/03/2023]
Abstract
BACKGROUND Traditional soy-fermented foods, such as miso, douche, natto, and tempeh have been widely used as a dietary supplement in Asian countries, and numerous reports on their phenolics and antioxidant activities have been published. Soy germ contains 10-fold higher phenolics than whole soybean, hence using soy germ as fermentation substrate will be more efficient than whole soybean. RESULTS Soy germ fermented with Aspergillus niger M46 resulted in a high-efficiency bio-transformation of phenolics and flavonoids to their metabolites, and a diverse secondary metabolic product was also found to response oxidation stress of fungal colonisation. Its antioxidant activity against hydroxyl radicals and superoxide radicals (IC50 = 0.8 and 6.15 µg mL(-1) , respectively) was about 205-fold and 47-fold higher than those of unfermented soy germ (IC50 = 164.0 and 290.48 µg mL(-1) ), respectively. These results were similar to those observed for Trolox, and more active than those of BHT and hesperidin. The β-glucosidase and α-amylase produced during fermentation were mainly responsible for mobilisation of the phenolics. CONCLUSION Our results demonstrate that fermented soy germ has the potential to be a good dietary supplement for prevention of oxidative stress-related diseases, and the solid-state bioprocessing strategy could be an innovative approach to enhance the antioxidant activity of soy germ.
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Affiliation(s)
- I-Chuan Sheih
- Department of Food and Beverage Management, Ta Hwa University of Science and Technology, No. 1 Dahua Rd, Qionglin Shiang, Hsinchu County, 307, Taiwan, Republic of China
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21
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Isolation of the Antioxidant Pyranonigrin-A from Rice Mold Starters Used in the Manufacturing Process of Fermented Foods. Biosci Biotechnol Biochem 2014; 71:2515-21. [DOI: 10.1271/bbb.70310] [Citation(s) in RCA: 40] [Impact Index Per Article: 3.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 02/07/2023]
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22
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Improved Palatability and Bio-Functionality of Super-Hard Rice by Soaking in a Barley-Koji MisoSuspension. Biosci Biotechnol Biochem 2014; 77:2419-29. [DOI: 10.1271/bbb.130528] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/08/2022]
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23
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Chang TS. Isolation, bioactivity, and production of ortho-hydroxydaidzein and ortho-hydroxygenistein. Int J Mol Sci 2014; 15:5699-716. [PMID: 24705463 PMCID: PMC4013590 DOI: 10.3390/ijms15045699] [Citation(s) in RCA: 34] [Impact Index Per Article: 3.1] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/03/2014] [Revised: 03/18/2014] [Accepted: 03/27/2014] [Indexed: 12/18/2022] Open
Abstract
Daidzein and genistein are two major components of soy isoflavones. They exist abundantly in plants and possess multiple bioactivities. In contrast, ortho-hydroxydaidzein (OHD) and ortho-hydroxygenistein (OHG), including 6-hydroxydaidzein (6-OHD), 8-hydroxydaidzein (8-OHD), 3'-hydroxydaidzein (3'-OHD), 6-hydroxygenistein (6-OHG), 8-hydroxygenistein (8-OHG), and 3'-hydroxygenistein (3'-OHG), are rarely found in plants. Instead, they are usually isolated from fermented soybean foods or microbial fermentation broth feeding with soybean meal. Accordingly, the bioactivity of OHD and OHG has been investigated less compared to that of soy isoflavones. Recently, OHD and OHG were produced by genetically engineering microorganisms through gene cloning of cytochrome P450 (CYP) enzyme systems. This success opens up bioactivity investigation and industrial applications of OHD and OHG in the future. This article reviews isolation of OHD and OHG from non-synthetic sources and production of the compounds by genetically modified microorganisms. Several bioactivities, such as anticancer and antimelanogenesis-related activities, of OHD and OHG, are also discussed.
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Affiliation(s)
- Te-Sheng Chang
- Department of Biological Science and Technology, National University of Tainan, 33 Sec. 2 Su-Lin St., Tainan 702, Taiwan.
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24
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Lee H, Kim BG, Ahn JH. Production of bioactive hydroxyflavones by using monooxygenase from Saccharothrix espanaensis. J Biotechnol 2014; 176:11-7. [DOI: 10.1016/j.jbiotec.2014.02.002] [Citation(s) in RCA: 18] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/26/2013] [Revised: 02/04/2014] [Accepted: 02/06/2014] [Indexed: 12/17/2022]
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25
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Hsu C, Ho HW, Chang CF, Wang ST, Fang TF, Lee MH, Su NW. Soy isoflavone-phosphate conjugates derived by cultivating Bacillus subtilis var. natto BCRC 80517 with isoflavone. Food Res Int 2013. [DOI: 10.1016/j.foodres.2013.05.027] [Citation(s) in RCA: 14] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/22/2023]
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26
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Hammerbacher A, Schmidt A, Wadke N, Wright LP, Schneider B, Bohlmann J, Brand WA, Fenning TM, Gershenzon J, Paetz C. A common fungal associate of the spruce bark beetle metabolizes the stilbene defenses of Norway spruce. PLANT PHYSIOLOGY 2013; 162:1324-36. [PMID: 23729780 PMCID: PMC3707561 DOI: 10.1104/pp.113.218610] [Citation(s) in RCA: 96] [Impact Index Per Article: 8.0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 03/26/2013] [Accepted: 05/28/2013] [Indexed: 05/03/2023]
Abstract
Norway spruce (Picea abies) forests suffer periodic fatal attacks by the bark beetle Ips typographus and its fungal associate, Ceratocystis polonica. Norway spruce protects itself against fungal and bark beetle invasion by the production of terpenoid resins, but it is unclear whether resins or other defenses are effective against the fungus. We investigated stilbenes, a group of phenolic compounds found in Norway spruce bark with a diaryl-ethene skeleton with known antifungal properties. During C. polonica infection, stilbene biosynthesis was up-regulated, as evidenced by elevated transcript levels of stilbene synthase genes. However, stilbene concentrations actually declined during infection, and this was due to fungal metabolism. C. polonica converted stilbenes to ring-opened, deglycosylated, and dimeric products. Chromatographic separation of C. polonica protein extracts confirmed that these metabolites arose from specific fungal enzyme activities. Comparison of C. polonica strains showed that rapid conversion of host phenolics is associated with higher virulence. C. polonica is so well adapted to its host's chemical defenses that it is even able to use host phenolic compounds as its sole carbon source.
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Affiliation(s)
- Almuth Hammerbacher
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | - Axel Schmidt
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | - Namita Wadke
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | - Louwrance P. Wright
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | - Bernd Schneider
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | - Joerg Bohlmann
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | - Willi A. Brand
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
| | | | | | - Christian Paetz
- Max Planck Institute for Chemical Ecology, 07745 Jena, Germany (A.H., A.S., N.W., L.P.W., B.S., T.M.F., J.G., C.P.)
- Michael Smith Laboratories, University of British Columbia, Vancouver, British Columbia, Canada V6T 1ZA (J.B.); and
- Max Planck Institute for Biogeochemistry, 07745 Jena, Germany (W.A.B.)
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Seo MH, Kim BN, Kim KR, Lee KW, Lee CH, Oh DK. Production of 8-hydroxydaidzein from soybean extract by Aspergillus oryzae KACC 40247. Biosci Biotechnol Biochem 2013; 77:1245-50. [PMID: 23748754 DOI: 10.1271/bbb.120899] [Citation(s) in RCA: 11] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/08/2022]
Abstract
Aspergillus oryzae KACC 40247 was selected from among 60 fungal strains as an effective 7,8,4'-trihydroxyisoflavone (8-hydroxydaidzein)-producing fungus. The optimal culture conditions for production by this strain in a 7-L fermentor were found to be 30 °C, pH 6, and 300 rpm. Under these conditions, A. oryzae KACC 40247 produced 62 mg/L of 8-hydroxydaidzein from soybean extract in 30 h, with a productivity of 2.1 mg/L/h. These are the highest production and productivity for 8-hydroxydaidzein ever reported. To increase production, several concentrations of daidzin and of daidzein as precursor were added at several culture times. The optimal addition time and concentration for daidzin were 12 h and 1,248 mg/L, and those for daidzein were 12 h and 254 mg/L respectively. Maximum production and productivity for 8-hydroxydaidzein with the addition of daidzein were 95 mg/L and 3.2 mg/L/h respectively, and those with the addition of daidzin were 160 mg/L and 4.4 mg/L/h respectively.
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Affiliation(s)
- Min-Ho Seo
- Department of Bioscience and Biotechnology, Konkuk University, Seoul, Republic of Korea
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28
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Chen YF, Chiang ML, Chou CC, Lo YC. Enhancing the antitumor cell proliferation and Cu(2+)-chelating effects of black soybeans through fermentation with Aspergillus awamori. J Biosci Bioeng 2013; 115:400-4. [PMID: 23177213 DOI: 10.1016/j.jbiosc.2012.10.018] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/23/2012] [Revised: 09/20/2012] [Accepted: 10/19/2012] [Indexed: 11/28/2022]
Abstract
In the present study, black soybeans were fermented with Aspergillus awamori at 30°C for 3 days. The effect of fermentation on the antiproliferative effect against human colon cancer cells, Caco-2 and HT-29 as well as Cu(2+)-chelating effect of black soybeans was investigated. It was found that the water, 80% methanol or 80% ethanol extract of fermented black soybeans showed a significantly higher (P < 0.05) antiproliferative and Cu(2+)-chelating effect than did the respective extract of non-fermented black soybeans. Generally, the methanol extract and the ethanol extract of fermented black soybeans exerted higher antiproliferative effect on both Caco-2 and HT-29 cells. While water extract of fermented black soybeans showed the highest Cu(2+)-chelating effect among the various extracts examined. Taking into account of extraction yields further revealed that bioactive principles that exhibit Cu(2+)-chelating effect could be extracted to the largest extent with water as the extraction solvent. With same amount of sample, water extract obtained from fermented black soybeans possesses the highest Cu(2+)-chelating abilities.
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Affiliation(s)
- Yu-Fei Chen
- Graduate Institute of Food Science and Technology, National Taiwan University, Taipei, Taiwan
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29
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Enhancements of isoflavone aglycones, total phenolic content, and antioxidant activity of black soybean by solid-state fermentation with Rhizopus spp. Eur Food Res Technol 2013. [DOI: 10.1007/s00217-013-1936-7] [Citation(s) in RCA: 31] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/27/2022]
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30
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Wittanalai S, Deming RL, Rakariyatham N. Characterization of Soybean Kapi During Fermentation withBacillusspp. FOOD BIOTECHNOL 2012. [DOI: 10.1080/08905436.2012.698768] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/28/2022]
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31
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Chien HL, Yang TC, Chou CC. Effects of Storage Conditions on the Stability of Isoflavone Isomers in Lactic Fermented Soymilk Powder. FOOD BIOPROCESS TECH 2012. [DOI: 10.1007/s11947-012-0792-y] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
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32
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Ichinose H. Molecular and Functional Diversity of Fungal Cytochrome P450s. Biol Pharm Bull 2012; 35:833-7. [DOI: 10.1248/bpb.35.833] [Citation(s) in RCA: 22] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
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Huang YH, Lai YJ, Chou CC. Fermentation temperature affects the antioxidant activity of the enzyme-ripened sufu, an oriental traditional fermented product of soybean. J Biosci Bioeng 2011; 112:49-53. [PMID: 21497549 DOI: 10.1016/j.jbiosc.2011.03.008] [Citation(s) in RCA: 27] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/22/2011] [Revised: 02/21/2011] [Accepted: 03/15/2011] [Indexed: 12/21/2022]
Abstract
In this study, sufu, a Chinese traditional fermented product of soybean, was prepared by ripening salted tofu cubes in the mash of Aspergillus oryzae-fermented rice-soybean koji possessing various hydrolytic enzymes at 25°C, 37°C and 45°C. Antioxidant activity including 2,2-diphenyl-2-picylhydoxyl (DPPH) radical-scavenging activity, Fe(2+)-chelating ability and reducing power exerted by the methanol extract of sufu was determined and compared with that of the non-fermented tofu extract. It was found that antioxidant activity of the sufu extracts was, generally, higher than the non-fermented tofu extract. Ripening temperature and the duration of ripening period affected the antioxidant activity of the sufu extracts. Taking into account of extraction yields, the sufu product ripened at 45°C for 16 days showed the most profound enhancement in the DPPH radical-scavenging effect and Fe(2+)-iron-chelating ability, which is 3.4 and 11.5 folds, respectively, that noted with the non-fermented tofu.
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Affiliation(s)
- Yung-Hsin Huang
- Graduate Institute of Food Science and Technology, National Taiwan University, Taipei 10673, Taiwan
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Construction and application of a functional library of cytochrome P450 monooxygenases from the filamentous fungus Aspergillus oryzae. Appl Environ Microbiol 2011; 77:3147-50. [PMID: 21378053 DOI: 10.1128/aem.02491-10] [Citation(s) in RCA: 26] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/18/2023] Open
Abstract
A functional library of cytochrome P450 monooxygenases from Aspergillus oryzae (AoCYPs) was constructed in which 121 isoforms were coexpressed with yeast NADPH-cytochrome P450 oxidoreductase in Saccharomyces cerevisiae. Using this functional library, novel catalytic functions of AoCYPs, such as catalytic potentials of CYP57B3 against genistein, were elucidated for the first time. Comprehensive functional screening promises rapid characterization of catalytic potentials and utility of AoCYPs.
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Hu HB, Zhu JH. Flavonoid Constituents from the Roots of Acanthopanax brachypus. Chem Pharm Bull (Tokyo) 2011; 59:135-9. [DOI: 10.1248/cpb.59.135] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
Affiliation(s)
- Hao-bin Hu
- College of Chemistry and Chemical Engineering, Longdong University
| | - Ji-hua Zhu
- College of Chemistry and Chemical Engineering, Longdong University
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36
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Ávila MR, Braccini ADL, Albrecht LP, Scapim CA, Mandarino JMG, Bazo GL, Cabral YCF. Effect of storage period on isoflavone content and physiological quality of conventional and transgenic soybean seeds. ACTA ACUST UNITED AC 2011. [DOI: 10.1590/s0101-31222011000100017] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
Abstract
The objective in this research was to evaluate the isoflavone content and the physiological quality of seed from conventional and transgenic soybean cultivars before and after 180 days of storage. Twenty one soybean cultivars: CD 202, CD 206, CD 208, CD 213RR, CD 214RR, CD 215, CD 216, CD 217, CD 218, CD 221, BRS 184, BRS 185, BRS 214, BRS 244RR, BRS 245RR, BRS 246RR, BRS 255, BRS 257, BRS 258, BRS 261 and BRS 262, grown in the 2005/2006 crop season, were assayed. The seeds were packed in Kraft paper bags and stored at room temperature under laboratory conditions. Seeds were evaluated with respect to their germination and vigor (first germination count, accelerated aging and tetrazolium test) and their total isoflavone contents and respective aglycon forms (daidzein, genistein and glycitein),glycosides (daidzine, genistine and glycitine) and malonyl conjugates. A completely randomized block design with six replications with the treatments set out within a subplot scheme (21 cultivars x 2 storage periods) was used. The F-test was used to compare means between storage periods and the Scott-Knott test to compare cultivars for each storage period, both with a 95% probability. It was concluded that isoflavone contents differ between cultivars and show a distinct behavior throughout storage.
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Cheng KC, Lin JT, Wu JY, Liu WH. Isoflavone Conversion of Black Soybean by ImmobilizedRhizopusspp. FOOD BIOTECHNOL 2010. [DOI: 10.1080/08905436.2010.524459] [Citation(s) in RCA: 13] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/18/2022]
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Park JS, Kim DH, Lee JK, Lee JY, Kim DH, Kim HK, Lee HJ, Kim HC. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors. Bioorg Med Chem Lett 2009; 20:1162-4. [PMID: 20022495 DOI: 10.1016/j.bmcl.2009.12.021] [Citation(s) in RCA: 39] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/28/2009] [Revised: 11/04/2009] [Accepted: 12/03/2009] [Indexed: 10/20/2022]
Abstract
Natural o-dihydroxyisoflavone (ODI) derivatives with variable hydroxyl substituent at the aromatic ring of isoflavone and three known isoflavones were isolated from five-year-old Korean fermented soybean paste (Doenjang) and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells comparing with other known isoflavones, 7,8,4'-trihydroxyisoflavone (1) and 7,3',4'-trihydroxyisoflavone (2) inhibited tyrosinase by 50% at a concentration of 11.21+/-0.8 microM and 5.23+/-0.6 microM (IC(50)), respectively, whereas, 6,7,4'-trihydroxyisoflavone (3), daidzein (4), glycitein (5) and genistein (6) showed very low inhibition activity. Furthermore, those compounds significantly suppressed the cellular melanin formation by 50% at a concentration of 12.23+/-0.7 microM (1), 7.83+/-0.7 microM (2), and 57.83+/-0.5(6) and show more activity than arbutin. But, compounds 3, 4, and 5 showed lower inhibition activity. This study shows that the position of hydroxyl substituent at the aromatic ring of isoflavone plays an important role in the intracellular regulation of melanin formation in cell-based assay system.
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Affiliation(s)
- Jun-Seong Park
- R&D Center, AmorePacific Corporation, Kyounggi-do, Republic of Korea.
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39
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Wu CH, Chou CC. Enhancement of aglycone, vitamin K2 and superoxide dismutase activity of black soybean through fermentation with Bacillus subtilis BCRC 14715 at different temperatures. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2009; 57:10695-700. [PMID: 19919117 DOI: 10.1021/jf902752t] [Citation(s) in RCA: 18] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/28/2023]
Abstract
In the present study, the change in the content and activity of some functional constituents including aglycone, the bioactive form of isoflavone, vitamin K2, and superoxide dismutase (SOD) of black soybeans during their solid fermentation with Bacillus subtilis BCRC 14715 at different temperatures (35, 40, 45, and 50 degrees C) for 18 h was investigated. It was generally found that fermentation resulted in an enhancement of these constituents, regardless of fermentation temperature, while varying the fermentation temperature of black soybeans produced variations in the enhancement. The 50 degrees C -fermented black soybean showed the most marked increase in the content of daidzein and genistein aglycone. On the other hand, the highest SOD activity and vitamin K2 content were found in the black soybeans fermented at 45 and 40-45 degrees C, respectively. Thus functional properties of black soybeans can be further improved through fermentation with B. subtilis BCRC 14715.
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Affiliation(s)
- Chia-Hsuan Wu
- Graduate Institute of Food Science and Technology, National Taiwan University, Taipei, Taiwan
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40
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Ye H, Xu H, Yu C, Dai Y, Liu G, Xu W, Yuan S. Hydroxylation of naringin by Trichoderma harzianum to dramatically improve its antioxidative activity. Enzyme Microb Technol 2009. [DOI: 10.1016/j.enzmictec.2009.06.011] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/20/2022]
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Huang RY, Chou CC. Stability of isoflavone isomers in steamed black soybeans and black soybean koji stored under different conditions. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2009; 57:1927-32. [PMID: 19256558 DOI: 10.1021/jf803702x] [Citation(s) in RCA: 10] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/27/2023]
Abstract
Steamed black soybeans and black soybean koji, a potentially functional food additive, were stored at 4 or 25 degrees C with or without deoxidant and desiccant for 120 days. After storage, steamed black soybeans and koji showed various extents of reduction in isoflavone contents dependent on storage temperature, packaging condition, and the kind of isoflavone isomer. Generally, black soybeans and koji showed the highest residual of isoflavone when they were stored at 4 degrees C with deoxidant and desiccant. Under this storage condition, beta-glucosides (daidzin, glycitin, and genistein), acetyl glucosides (acetyldaidzin, acetylglycitin, and acetylgenistin), manlonyl glucosides (malonyldaidzin, malonglycitin, and malonylgenistin), and aglycones (daidzein, glycitein, and genistin) in steamed black soybeans exhibited residuals of 100.1-100.9, 92.0-99.4, 90.0-94.0, and 77.2-78.8%, respectively, of their original contents after 120 days of storage. Meanwhile, the residuals found in black soybean koji were 77.8-90.0, 13.1-88.9, 66.7-85.5, and 76.4-80.6%, respectively.
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Affiliation(s)
- Ru-Yue Huang
- Graduate Institute of Food Science and Technology, National Taiwan University, Taipei, Taiwan
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42
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ortho-Dihydroxyisoflavone derivatives from aged Doenjang (Korean fermented soypaste) and its radical scavenging activity. Bioorg Med Chem Lett 2008; 18:5006-9. [DOI: 10.1016/j.bmcl.2008.08.016] [Citation(s) in RCA: 45] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/28/2008] [Revised: 07/22/2008] [Accepted: 08/06/2008] [Indexed: 11/19/2022]
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43
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Nechepurenko IV, Polovinka MP, Komarova NI, Korchagina DV, Salakhutdinov NF, Nechepurenko SB. Low-molecular-weight phenolic compounds from Hedysarum theinum roots. Chem Nat Compd 2008. [DOI: 10.1007/s10600-008-0009-9] [Citation(s) in RCA: 21] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
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Lee MJ, Kim JH. Estimated dietary isoflavone intake among Korean adults. Nutr Res Pract 2007; 1:206-11. [PMID: 20368940 PMCID: PMC2849024 DOI: 10.4162/nrp.2007.1.3.206] [Citation(s) in RCA: 11] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/13/2007] [Revised: 07/10/2007] [Accepted: 08/14/2007] [Indexed: 11/30/2022] Open
Abstract
This study estimated the isoflavone intake level in Koreans using Food Frequency Questionnaire and analyzed related variables. The results showed that the average daily intake of isoflavone in adults was shown as 23.1 mg. The isoflavone intake level at 50 percentile was 16.9 mg (0~190 mg), and 10% of adults took almost 50 mg of isoflavone a day and 10% took about 5 mg a day. The major food sources for isoflavone in Koreans were in the order of soybean, soybean paste, soy milk, soybean curd (tofu), and bean sprouts; the intake was different depending on age, educational background, occupation, economic standard, and family type. The result showed higher isoflavone intake levels in the group over 30 years old and the highest isoflavone intake in subjects working in farming/fishery, followed by housemakers. According to the differences by families the families with elderly members showed 50% higher isoflavone intake than young families with friends or siblings. Depending on related ecological variables, therefore, various nutrition education programs should be developed for a variety of intakes of soybean foods, along with easy and simple cooking methods as parts of continuous research.
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Affiliation(s)
- Min-June Lee
- Research Institute of Food and Nutritional Sciences, Yonsei University, Seoul 120-749, Korea
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45
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Chang TS, Ding HY, Tai SSK, Wu CY. Metabolism of the soy isoflavones daidzein and genistein by fungi used in the preparation of various fermented soybean foods. Biosci Biotechnol Biochem 2007; 71:1330-3. [PMID: 17485838 DOI: 10.1271/bbb.60573] [Citation(s) in RCA: 30] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/08/2022]
Abstract
The ability of fungi used in the preparation of fermented soybean foods to metabolize the soy isoflavones daidzein and genistein was investigated. A total of 21 fungal strains from dou-chi, miso, sake, soy sauce, and sufu were screened. The genera of the tested fungi included Actinomucor, Aspergillus, Candida, Debaryomyces, Monascus, Mucor, Rhizopus, Saccharomyces, and Zygosaccharomyces. The results were that all tested Aspergillus strains from these soybean foods, including five A. oryzae strains, one A. sojae strain, and one A. tamarii strain, metabolized both daidzein and genistein. In contrast, no other tested fungi from the fermented soybean foods metabolized either daidzein or genistein. The metabolites of daidzein and genistein by Aspergillus strains were identified as 8-hydroxydaidzein and 8-hydroxygenistein, respectively, based on their mass, (1)H-, and (13)C-NMR spectra.
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Affiliation(s)
- Te-Sheng Chang
- Department of Biological Science and Technology, National University of Tainan, Tainan, Taiwan
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46
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Abstract
Biotransformation of the daidzein ditiglate (2) by fungi, Aspergillus niger and Glomerella cingulata was investigated. Compound 2 was transformed to daidzein (1) by A. niger and G. cingulata. This suggested that compound 2 was converted to compound 1 by hydrolysis at both of the C-7 and C-4' positions.
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Affiliation(s)
- Mitsuo Miyazawa
- Faculty of Science and Engineering, Department of Applied Chemistry, Kinki University, Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan.
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Wang LJ, Yin LJ, Li D, Zou L, Saito M, Tatsumi E, Li LT. Influences of processing and NaCl supplementation on isoflavone contents and composition during douchi manufacturing. Food Chem 2007. [DOI: 10.1016/j.foodchem.2006.03.029] [Citation(s) in RCA: 25] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/24/2022]
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48
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Mushroom tyrosinase inhibitory effects of isoflavones isolated from soygerm koji fermented with Aspergillus oryzae BCRC 32288. Food Chem 2007. [DOI: 10.1016/j.foodchem.2007.05.019] [Citation(s) in RCA: 57] [Impact Index Per Article: 3.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/24/2022]
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49
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Russin T, Boye J, Pham H, Arcand Y. Antioxidant Properties of Genistein in a Model Edible Oil System. J Food Sci 2006. [DOI: 10.1111/j.1750-3841.2006.00111.x] [Citation(s) in RCA: 10] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
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50
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Takahashi K, Araki H, Miyazawa M. Biotransformation of isoflavones by the larvae of the common cutworm (Spodoptera litura). Chem Pharm Bull (Tokyo) 2006; 54:719-21. [PMID: 16651777 DOI: 10.1248/cpb.54.719] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
Abstract
Biotransformation of the 5,7,4'-trimethoxyisoflavone (1), 6,7,4'-trimethoxyisoflavone (2), and 7,4'-dimethoxyisoflavone (3) by insects, Spodoptera litura was investigated. Compound 1 was transformed to 5-hydroxy-7,4'-dimethoxyisoflavone (4), 7-hydroxy-5,4'-dimethoxyisoflavone (5) and 4'-hydroxy-5,7-dimethoxyisoflavone (6) by S. litura. Compounds 2 and 3 were hardly metabolized by S. litura. This suggested that compound 1 was converted to compounds 4, 5 and 6 by demethylation at the C-5, C-7 and C-4' position, respectively.
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Affiliation(s)
- Koji Takahashi
- Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosaka, Osaka 577-8502, Japan
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