8-Dimethylallylnaringenin 2′-hydroxylase, the crucial cytochrome P450 mono-oxygenase for lavandulylated flavanone formation in Sophora flavescens cultured cells

Yamamoto, Haruhiko; Yatou, Atsushi; Inoue, Ken‐ichiro

doi:10.1016/s0031-9422(01)00270-9

Cited by 12 publications

(11 citation statements)

References 33 publications

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“…Moreover, 4-dimethylallylglycinol, the product of G4DT, is cyclized by another cytochrome P450 localized at the ER (Welle and Grisebach 1988). These different localizations of successive biosynthetic enzymes suggest possible intracellular movement of intermediates between the ER and plastids (Figure 3), a movement that may also occur during the synthesis of sophoraflavanone G in S. flavescens (Sasaki et al 2008;Yamamoto et al 2000Yamamoto et al , 2001. Recently, using mutants in tocopherol biosynthesis and the transorganellar complementation approach, in which plastid-localized enzymes were retargeted to the ER, nonpolar substrates in plastids were found to be accessed by ER-localized enzymes (Mehrshahi et al 2013).…”

Section: Interactions With Pathogensmentioning

confidence: 99%

Flavonoids in plant rhizospheres: secretion, fate and their effects on biological communication

Sugiyama

Yazaki

2014

Plant Biotechnology

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Flavonoids, one of the most-described group of plant "specialized metabolites", consist of more than 10,000 structurally diverse compounds. Most flavonoids accumulate in plant vacuoles as glycosides, with some released by the roots into rhizospheres. These flavonoids are involved in biological communications with rhizobia, arbuscular mycorrhizal fungi, plant growth promoting rhizobacteria, pathogens, nematodes, and other plant species. Both aglycones and glycosides of flavonoids are found in root exudates and in soils. This review describes researches on the mechanisms of flavonoid secretion and the fate of flavonoids released into rhizospheres. This review also discusses the direction of future research that may elucidate the specific roles of flavonoids in biological communications in rhizospheres, enabling the utilization of flavonoid activities and functions in agricultural practice.

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Section: Interactions With Pathogensmentioning

confidence: 99%

Flavonoids in plant rhizospheres: secretion, fate and their effects on biological communication

Sugiyama

Yazaki

2014

Plant Biotechnology

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“…1). This intermediate, 8-dimethylallyl naringenin (8DN), is further hydroxylated to form leachianone G (LG) by 8DN 2#-hydroxylase (Yamamoto et al, 2001), and the second prenylation takes place at the prenyl side chain of LG catalyzed by LG 2$-dimethylallyltransferase (Zhao et al, 2003). Both prenylation reactions are Mg 21 dependent, plastid localized, and involve membranebound proteins.…”

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Cloning and Characterization of Naringenin 8-Prenyltransferase, a Flavonoid-Specific Prenyltransferase of Sophora flavescens

et al. 2008

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Prenylated flavonoids are natural compounds that often represent the active components in various medicinal plants and exhibit beneficial effects on human health. Prenylated flavonoids are hybrid products composed of a flavonoid core mainly attached to either 5-carbon (dimethylallyl) or 10-carbon (geranyl) prenyl groups derived from isoprenoid (terpenoid) metabolism, and the prenyl groups are crucial for their biological activity. Prenylation reactions in vivo are crucial coupling processes of two major metabolic pathways, the shikimate-acetate and isoprenoid pathways, in which these reactions are also known as a rate-limiting step. However, none of the genes responsible for the prenylation of flavonoids has been identified despite more than 30 years of research in this field. We have isolated a prenyltransferase gene from Sophora flavescens, SfN8DT-1, responsible for the prenylation of the flavonoid naringenin at the 8-position, which is specific for flavanones and dimethylallyl diphosphate as substrates. Phylogenetic analysis shows that SfN8DT-1 has the same evolutionary origin as prenyltransferases for vitamin E and plastoquinone. The gene expression of SfN8DT-1 is strictly limited to the root bark where prenylated flavonoids are solely accumulated in planta. The ectopic expression of SfN8DT-1 in Arabidopsis thaliana resulted in the formation of prenylated apigenin, quercetin, and kaempferol, as well as 8-prenylnaringenin. SfN8DT-1 represents the first flavonoid-specific prenyltransferase identified in plants and paves the way for the identification and characterization of further genes responsible for the production of this large and important class of secondary metabolites.The prenylation of aromatic compounds is a major contributor to the diversity of plant secondary metabolites due to differences in prenylation position on the aromatic ring, various lengths of prenyl chain, and further modifications of the prenyl moiety, e.g. cyclization and hydroxylation, resulting in the occurrence of more than 1,000 prenylated compounds in plants (Tahara and Ibrahim, 1995;Barron and Ibrahim, 1996). In particular, prenylated flavonoids in higher plants protect them by exhibiting strong antibacterial and antifungal activities (Sohn et al., 2004). Many prenylated flavonoids have been identified as active components in medicinal plants with biological activities, such as anticancer, anti-androgen, anti-leishmania, and anti-nitric oxide production (De Naeyer et al., 2004;Ahmed-Belkacem et al., 2005;Han et al., 2006). Due to the beneficial effects for human health, prenylated flavonoids are of particular interest as lead compounds for producing new drugs and functional foods. The prenylation of the flavonoid core increases the lipophilicity and the membrane permeability, which is one of the proposed reasons for the enhanced biological activities of prenylated flavonoids (Wang et al., 1997;Maitrejean et al., 2000;Murakami et al., 2000). However, none of the genes responsible for the prenylation reactions has been identified d...

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“…LGDT activity was assayed as described above by using 50 L of each gradient fraction, whereas the activities of N8DT and 2ЈOH were measured as described by Yamamoto et al (2000Yamamoto et al ( , 2001. The C4H assay was initiated by adding NADPH at a final concentration of 1 mm to a reaction mixture (150 L) containing 100 mm Tris-HCl buffer (pH 7.5), 1 mm trans-cinnamic acid, and 100 L of each gradient fraction.…”

Section: Assays Of Lgdt N8dt 2oh and C4h By Hplcmentioning

confidence: 99%

“…That is, the first dimethylallylation occurs on the flavanone nucleus catalyzed by naringenin 8-dimethylallyltransferase (N8DT) that does not accept lavandulyl diphosphate as the prenyl donor to afford 8-dimethylallylnaringenin (Yamamoto et al, 2000). This intermediate is further hydroxylated to form leachianone G (LG) by 8-dimethylallylnaringenin 2Ј-hydroxylase (2ЈOH; Yamamoto et al, 2001), and the second dimethylallylation takes place on the prenyl side chain of LG catalyzed by an uncharacterized dimethylallyltransferase to give SFG. More recently, we revealed that two isoprene units in the lavandulyl group of SFG were generated via the 1-deoxy-d-xylulose-5-phosphate (DXP) pathway (Yamamoto et al, 2002), which is an alternative route for IPP biosynthesis in the plastids (Eisenreich et al, 1998), suggesting that lavandulyl group formation involves two discontinuous dimethylallylation steps that take place in the plastids.…”

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confidence: 99%

Characterization of Leachianone G 2″ -Dimethylallyltransferase, a Novel Prenyl Side-Chain Elongation Enzyme for the Formation of the Lavandulyl Group of Sophoraflavanone G in Sophora flavescens Ait. Cell Suspension Cultures

et al. 2003

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Leachianone G (LG) 2ЈЈ-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme, was identified in Sophora flavescens Ait. cultured cells. The enzyme transfers a dimethylallyl group to the 2ЈЈ position of another dimethylallyl group attached at position 8 of LG to form sophoraflavanone G, a branched monoterpenoid-conjugated flavanone characteristic to this plant. This membrane-bound dimethylallyltransferase required Mg 2ϩ (optimum concentration was 10 mm) for the reaction and had an optimum pH of 8.8. It utilized dimethylallyl diphosphate as the sole prenyl donor, and the 2Ј-hydroxy function in LG was indispensable to the activity. The apparent K m values for dimethylallyl diphosphate and LG were 59 and 2.3 m, respectively. Subcellular localization of three enzymes that participated in the formation of the lavandulyl group was also investigated by sucrose density gradient centrifugation. Two prenyltransferases, naringenin 8-dimethylallyltransferase and LG 2ЈЈ-dimethylallyltransferase, were localized in the plastids, whereas 8-dimethylallylnaringenin 2Ј-hydroxylase, which catalyzes the crucial step in the lavandulyl-group formation, was associated with the endoplasmic reticulum. These results suggest the close cooperation between the plastids and the endoplasmic reticulum in the formation of lavandulyl groups.More than 30,000 isoprenoid compounds-the most chemically diverse family of metabolites-are found in nature (Eisenreich et al., 1998). The vast majority of these compounds have "regular" 1Ј-4 (head-to-tail) linkages between isoprenoid units formed by isoprenyl diphosphate synthases, which are types of prenyltransferase. These enzymes catalyze the prenyl diphosphate elongation reaction that results in the consecutive 1Ј-4 condensations of isopentenyl diphosphate (IPP), the five-carbon building unit, with allylic isoprenyl diphosphates such as dimethylallyl diphosphate (DMAPP) and geranyl diphosphate (GPP; Ogura and Koyama, 1998; Liang et al., 2002). "Irregular" (non-head-to-tail) isoprenoids are also found, of which the most prominent examples are the 1Ј-1 (tail-to-tail) condensed isoprenoids such as squalene and phytoene, which are important precursors of sterols and carotenoids, respectively (Poulter, 1990). The biosyntheses of these tail-to-tail condensed terpenoids have been well characterized, but little is known about other nonhead-to-tail condensed terpenoids except for chrysanthemyl diphosphate synthase, which catalyzes the condensation of two molecules of DMAPP to produce chrysanthemyl diphosphate, a branched monoterpene with a c1Ј-2-3 linkage between two isoprenoid units (Poulter, 1990;Rivera et al., 2001). A lavandulyl group, another example of the branched monoterpenoid unit, is found in labiataeous and compositaeous plants as essential oils (de Lampasona et al., 1997;Tsuro et al., 2001; Gunawardena et al., 2002), and in leguminous and moraceous plants as diverse prenylated flavonoids (Barron and Ibrahim, 1996). Epstein and Poulter (1973) suggested very early that chrysanthemyl d...

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8-Dimethylallylnaringenin 2′-hydroxylase, the crucial cytochrome P450 mono-oxygenase for lavandulylated flavanone formation in Sophora flavescens cultured cells

Cited by 12 publications

References 33 publications

Flavonoids in plant rhizospheres: secretion, fate and their effects on biological communication

Flavonoids in plant rhizospheres: secretion, fate and their effects on biological communication

Cloning and Characterization of Naringenin 8-Prenyltransferase, a Flavonoid-Specific Prenyltransferase of Sophora flavescens

Characterization of Leachianone G 2″ -Dimethylallyltransferase, a Novel Prenyl Side-Chain Elongation Enzyme for the Formation of the Lavandulyl Group of Sophoraflavanone G in Sophora flavescens Ait. Cell Suspension Cultures

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