Chalcone Isomerase Isozymes with Different Substrate Specificities towards 6′-Hydroxy- and 6′-Deoxychalcones in Cultured Cells of Glycyrrhiza echinata, a Leguminous Plant Producing 5-Deoxyflavonoids

Kimura, Yoshiki; Aoki, Takeshi; Ayabe, Shin-ichi

doi:10.1093/pcp/pce130

Cited by 43 publications

(30 citation statements)

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“…Transcripts of three CHI genes were constitutively detected in L. japonicus seedlings, and the accumulation of the CHI1 and CHI3 transcripts was increased by GSH treatment, which induces an isoflavan phytoalexin, vestitol (Shimada et al, 2000). These expression patterns together with their kinetic parameters indicate that these three CHIs of L. japonicus correspond to the CHI isozymes of another legume, licorice, in which two type II CHIs and one type I CHI were biochemically characterized (Kimura et al, 2001). Furthermore, expressed sequence tag data of soybean (Glycine max; GenBank accession nos.…”

Section: Discussionmentioning

confidence: 89%

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A Cluster of Genes Encodes the Two Types of Chalcone Isomerase Involved in the Biosynthesis of General Flavonoids and Legume-Specific 5-Deoxy(iso)flavonoids in Lotus japonicus

et al. 2003

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Leguminous plants produce 5-deoxyflavonoids and 5-deoxyisoflavonoids that play essential roles in legume-microbe interactions. Together with chalcone polyketide reductase and cytochrome P450 2-hydroxyisoflavanone synthase, the chalcone isomerase (CHI) of leguminous plants is fundamental in the construction of these ecophysiologically active flavonoids. Although CHIs of nonleguminous plants isomerize only 6Ј-hydroxychalcone to 5-hydroxyflavanone (CHIs with this function are referred to as type I), leguminous CHIs convert both 6Ј-deoxychalcone and 6Ј-hydroxychalcone to 5-deoxyflavanone and 5-hydroxyflavanone, respectively (referred to as type II). In this study, we isolated multiple CHI cDNAs (cCHI1-cCHI3) from a model legume, Lotus japonicus. In contrast to previous observations, the amino acid sequence of CHI2 was highly homologous to nonleguminous CHIs, whereas CHI1 and CHI3 were the conventional leguminous type. Furthermore, genome sequence analysis revealed that four CHI genes (CHI1-3 and a putative gene, CHI4) form a tandem cluster within 15 kb. Biochemical analysis with recombinant CHIs expressed in Escherichia coli confirmed that CHI1 and CHI3 are type II CHIs and that CHI2 is a type I CHI. The occurrence of both types of CHIs is probably common in leguminous plants, and it was suggested that type II CHIs evolved from an ancestral CHI by gene duplication and began to produce 5-deoxy(iso)flavonoids along with the establishment of the Fabaceae.

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Section: Discussionmentioning

confidence: 89%

“…Recently, biochemical evidence suggested for the first time that a leguminous plant licorice (Glycyrrhiza echinata) contains both type I and type II CHI isozymes (Kimura et al, 2001). A difference in responsiveness in their expression to elicitor treatment was also shown.…”

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confidence: 99%

A Cluster of Genes Encodes the Two Types of Chalcone Isomerase Involved in the Biosynthesis of General Flavonoids and Legume-Specific 5-Deoxy(iso)flavonoids in Lotus japonicus

et al. 2003

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“…Members of the second subfamily (CHI2) are at least 60% similar to each other and occur in many distantly related plant species. All members of this subfamily that have been biochemically assayed metabolize only naringenin chalcone (Kimura et al, 2001). Based on sequence homology, the soybean CHI1 subfamily belongs to type II CHIs, and the CHI2 subfamily belongs to the type I CHIs.…”

Section: Identification Of Chi Expressed Sequence Tags In Soybeanmentioning

confidence: 99%

Partial Reconstruction of Flavonoid and Isoflavonoid Biosynthesis in Yeast Using Soybean Type I and Type II Chalcone Isomerases

et al. 2005

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Flavonoids and isoflavonoids are major plant secondary metabolites that mediate diverse biological functions and exert significant ecological impacts. These compounds play important roles in many essential physiological processes. In addition, flavonoids and isoflavonoids have direct but complex effects on human health, ranging from reducing cholesterol levels and preventing certain cancers to improving women's health. In this study, we cloned and functionally characterized five soybean (Glycine max) chalcone isomerases (CHIs), key enzymes in the phenylpropanoid pathway that produces flavonoids and isoflavonoids. Gene expression and kinetics analysis suggest that the soybean type I CHI, which uses naringenin chalcone as substrate, is coordinately regulated with other flavonoid-specific genes, while the type II CHIs, which use a variety of chalcone substrates, are coordinately regulated with an isoflavonoid-specific gene and specifically activated by nodulation signals. Furthermore, we found that some of the newly identified soybean CHIs do not require the 4#-hydroxy moiety on the substrate for high enzyme activity. We then engineered yeast (Saccharomyces cerevisiae) to produce flavonoid and isoflavonoid compounds. When one of the type II CHIs was coexpressed with an isoflavone synthase, the enzyme catalyzing the first committed step of isoflavonoid biosynthesis, various chalcone substrates added to the culture media were converted to an assortment of isoflavanones and isoflavones. We also reconstructed the flavonoid pathway by coexpressing CHI with either flavanone 3b-hydroxylase or flavone synthase II. The in vivo reconstruction of the flavonoid and isoflavonoid pathways in yeast provides a unique platform to study enzyme interactions and metabolic flux.Flavonoids and isoflavonoids are major plant secondary metabolites that mediate diverse biological functions and exert significant ecological impacts. Approximately 20% of the carbon fixed by photosynthesis is believed to be channeled into the phenylpropanoid pathway, generating the majority of the phenolic compounds found in nature, including flavonoids and isoflavonoids (Weisshaar and Jenkins, 1998). These compounds play important roles in many essential physiological processes. For example, lignins are major cell wall components, flavonols are UV protectants, and anthocyanins are the primary attractants for pollinators in many species . In addition, flavonoids and isoflavonoids have direct but complex effects on human health. For example, resveratrol found in red wine has been shown to double the life span of yeast (Saccharomyces cerevisiae; Howitz et al., 2003), the flavonols and tannins found in green tea can drastically reduce the likelihood of stroke and heart disease, and the isoflavones produced by soybean (Glycine max) can prevent many hormone-dependent cancers and improve women's health (Beecher, 2003). Despite being one of the most studied plant secondary-metabolic pathways, surprising new functions and characteristics of these compounds are still be...

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“…Quá trình chuyển hóa tổng hợp isoflavone có nhiều enzyme tham gia, bao gồm phenylalanine ammonia lyase (PAL), chalcone synthase (CHS), chalcone reductase (CHR), chalcone isomerase (CHI) và isoflavone synthase (IFS). Trong đó CHI là enzyme nắm giữ vị trí then chốt trong con đường sản sinh flavonoid và xúc tác chuyển đổi chalcone thành flavanone, là nguyên liệu cho quá trình chuyển hóa flavonoid và isoflavonoid [5]. Các nghiên cứu về enzyme CHI đã được thực hiện trên cây Arabidopsis đã chỉ ra rằng, chỉ khi có mặt của CHI thì Arabidopsis mới hình thành flavonoid; trong vỏ cà chua không có CHI và naringenin, khi làm tăng CHI dẫn đến sự gia tăng lên 78 lần hàm lượng flavonoid [7,8].…”

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The characteristics of gmchi gene isolated from soybean cultivars with different isoflavone content

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Chalcone Isomerase Isozymes with Different Substrate Specificities towards 6′-Hydroxy- and 6′-Deoxychalcones in Cultured Cells of Glycyrrhiza echinata, a Leguminous Plant Producing 5-Deoxyflavonoids

Cited by 43 publications

References 22 publications

A Cluster of Genes Encodes the Two Types of Chalcone Isomerase Involved in the Biosynthesis of General Flavonoids and Legume-Specific 5-Deoxy(iso)flavonoids in Lotus japonicus

A Cluster of Genes Encodes the Two Types of Chalcone Isomerase Involved in the Biosynthesis of General Flavonoids and Legume-Specific 5-Deoxy(iso)flavonoids in Lotus japonicus

Partial Reconstruction of Flavonoid and Isoflavonoid Biosynthesis in Yeast Using Soybean Type I and Type II Chalcone Isomerases

The characteristics of gmchi gene isolated from soybean cultivars with different isoflavone content

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