Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daidzein and glycitein by bacteria isolated from tempe

Klus, Klaus; Barz, W.

doi:10.1007/bf02529741

Cited by 41 publications

(19 citation statements)

References 22 publications

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“…5). The UV spectrum of the latter compound ( max ϭ 212, 230, 257, and 323 nm in methanol) was identical to that of authentic 6,7,4Ј-trihydroxyisoflavone and consistent with values reported earlier (39). Furthermore, the NMR spectrum of the compound proved that it was 6,7,4Ј-trihydroxyisoflavone ( Fig.…”

Section: Fig 2 Hplc Analysis Of (Rs)-liquiritigenin Conversion In supporting

confidence: 89%

“…This substitution pattern is represented in 6,7,4Ј-trihydroxyisoflavone (factor 2), a putative precursor of the constitutively formed isoflavonoid glycitein (35,36). The formation of polyhydroxylated isoflavones, including 6,7,4Ј-trihydroxyisoflavone, from the soybean isoflavones daidzein and glycitein has been observed during tempe (fermented soybean) production and has been attributed to the metabolic capacity of bacteria including Micrococcus and Arthrobacter species by performing hydroxylation and demethylation reactions at ring A (39,48). In the present study, 6,7,4Ј-trihydroxyisoflavone was obtained from enzymatically formed 2,6,7,4Ј-tetrahydoxyisoflavanone by acid treatment.…”

Section: Discussionmentioning

confidence: 99%

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Flavonoid 6-Hydroxylase from Soybean (Glycine maxL.), a Novel Plant P-450 Monooxygenase

Latunde-Dada¹,

Cabello‐Hurtado²,

Czittrich³

et al. 2001

Journal of Biological Chemistry

116

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Cytochrome P-450-dependent hydroxylases are typical enzymes for the modification of basic flavonoid skeletons. We show in this study that CYP71D9 cDNA, previously isolated from elicitor-induced soybean (Glycine max L.) cells, codes for a protein with a novel hydroxylase activity. When heterologously expressed in yeast, this protein bound various flavonoids with high affinity (1.6 to 52 M) and showed typical type I absorption spectra. These flavonoids were hydroxylated at position 6 of both resorcinol-and phloroglucinol-based A-rings. Flavonoid 6-hydroxylase (CYP71D9) catalyzed the conversion of flavanones more efficiently than flavones. Isoflavones were hardly hydroxylated. As soybean produces isoflavonoid constituents possessing 6,7-dihydroxy substitution patterns on ring A, the biosynthetic relationship of flavonoid 6-hydroxylase to isoflavonoid biosynthesis was investigated. Recombinant 2-hydroxyisoflavanone synthase (CYP93C1v2) efficiently used 6,7,4-trihydroxyflavanone as substrate. For its structural identification, the chemically labile reaction product was converted to 6,7,4-trihydroxyisoflavone by acid treatment. The structures of the final reaction products for both enzymes were confirmed by NMR and mass spectrometry. Our results strongly support the conclusion that, in soybean, the 6-hydroxylation of the A-ring occurs before the 1,2-aryl migration of the flavonoid B-ring during isoflavanone formation. This is the first identification of a flavonoid 6-hydroxylase cDNA from any plant species.Flavonoids are a diverse group of natural products that serve important roles in plants during growth, during development, and in defense against microorganisms and pests (1, 2). These compounds are synthesized from phenylpropanoid-and acetate-derived precursors through central pathways furnishing basic C 6 -C 3 -C 6 flavonoid skeletons and, in addition, through a variety of reactions leading to a range of modified aglycones and subsequently to their glycosylated derivatives within each flavonoid class. Many of the enzymes of flavonoid biosynthesis have been extensively studied (3), and recent molecular biological approaches have complemented biochemical methods in elucidating the mechanism and regulation of flavonoid biosynthesis (4). Typical enzymes belonging to the complex branch pathways for the elaboration of flavonoid skeletons are cytochrome P-450-dependent hydroxylases (3), such as flavonoid 3Ј-hydroxylase (5), flavonoid 3Ј,5Ј-hydroxylase (6), isoflavone 2Ј-hydroxylase (7), flavanone 2-hydroxylase (8), flavone synthase II (9, 10), and 2-hydroxyisoflavanone synthase (2HIS) 1 (11-13). Whereas flavonoid 3Ј-hydroxylase and flavonoid 3Ј,5Ј-hydroxylase are responsible for the formation of the 3Ј,5Ј-hydroxylation pattern of the flavonoid B-ring, hydroxylation of the isoflavone B-ring at the 2Ј position (isoflavone 2Ј-hydroxylase) is one of the key reactions leading to pterocarpan structures. The formation of flavones and isoflavones from flavanones is catalyzed by several evolutionarily related P-450s, either in a ...

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Section: Fig 2 Hplc Analysis Of (Rs)-liquiritigenin Conversion In supporting

confidence: 89%

Section: Discussionmentioning

confidence: 99%

Flavonoid 6-Hydroxylase from Soybean (Glycine maxL.), a Novel Plant P-450 Monooxygenase

Latunde-Dada¹,

Cabello‐Hurtado²,

Czittrich³

et al. 2001

Journal of Biological Chemistry

116

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“…Other 12 contaminants such as Brevibacterium epidermidis and Micrococcus luteus known to play a role in the formation of antioxidants in tempeh (Klus and Barz 1995). Furthermore, bacteria in tempeh is also known as one of the factors that play a role in the formation of a bitter taste in tempeh (Barus et al 2008).…”

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confidence: 99%

Klebsiella pneumoniae from Indonesian Tempeh were Genetically Different from that of Pathogenic Isolates

2014

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Tempe merupakan salah satu makanan utama tradisional Indonesia yang terbuat dari kacang kedelai dengan fermentasi menggunakan cendawan Rhizopus oligosporus atau R. microsporus. Selama proses pengolahan, bakteri yang berasal dari lingkungan dan inokulum awal menjadi bagian yang tidak terpisahkan dari tempe, bahkan memiliki peranan yang penting dalam menentukan kualitas akhir pada tempe. Beberapa penelitian telah melaporkan keberadaan Klebsiella pneumoniae pada tempe sebagai salah satu bakteri penghasil vitamin B12 pada tempe. Akan tetapi, K. pneumoniae juga dikenal sebagai patogen oportunis penyebab penyakit pneumonia dan abses hati pada manusia. Pada penelitian ini, metode Enterobacterial Repetitive Intergenic ConsensusPolymerase Chain Reaction (ERIC-PCR) digunakan untuk membandingkan keragaman genetik K. pneumoniae pada tempe dibandingkan dengan isolat medis. Hasil penelitian ini menunjukkan bahwa secara genetik pneumoniae pada tempe berbeda dengan isolat medis. Kata kunci: ERIC-PCR, tempeKlebsiella pneumoniae, Klebsiella pneumoniae,

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“…However, for tempeh, OHD and OHG are not produced by the fungal Rhizopus sp. in the tempeh but by bacteria isolated from tempeh [41,42]. The enzyme of the bacteria for the biotransformation of OHD and OHG from daidzein and genistein remains unknown.…”

Section: Isolation Of Ohd and Ohgmentioning

confidence: 99%

Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein

Chang

2014

IJMS

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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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Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daidzein and glycitein by bacteria isolated from tempe

Cited by 41 publications

References 22 publications

Flavonoid 6-Hydroxylase from Soybean (Glycine maxL.), a Novel Plant P-450 Monooxygenase

Flavonoid 6-Hydroxylase from Soybean (Glycine maxL.), a Novel Plant P-450 Monooxygenase

Klebsiella pneumoniae from Indonesian Tempeh were Genetically Different from that of Pathogenic Isolates

Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein

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