Biosynthesis of homoeriodictyol from eriodictyol by flavone 3′-O-methyltransferase from recombinant Yarrowia lioplytica: Heterologous expression, biochemical characterization, and optimal transformation

Liu, Qingtao; Liu, Long; Zhou, Jingwen; Shin, Hyun‐Dong; Chen, Rachel R.; Madzak, Catherine; Li, Jianghua; Du, Guocheng; Chen, Jian

doi:10.1016/j.jbiotec.2013.07.025

Cited by 19 publications

(15 citation statements)

References 22 publications

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“…The highest K M value was obtained for luteolin. The K M values of PfOMT3 toward flavonoids are comparable to those of other FOMTs [ 20 , 21 , 22 , 33 , 34 ]. Although PfOMT3 only had moderate affinity for naringenin, it had the highest V max value for this substrate.…”

Section: Resultssupporting

confidence: 62%

Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production

Park

Lee

et al. 2020

Molecules

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Methylation is a common structural modification that can alter and improve the biological activities of natural compounds. O-Methyltransferases (OMTs) catalyze the methylation of a wide array of secondary metabolites, including flavonoids, and are potentially useful tools for the biotechnological production of valuable natural products. An OMT gene (PfOMT3) was isolated from perilla leaves as a putative flavonoid OMT (FOMT). Phylogenetic analysis and sequence comparisons showed that PfOMT3 is a class II OMT. Recombinant PfOMT3 catalyzed the methylation of flavonoid substrates, whereas no methylated product was detected in PfOMT3 reactions with phenylpropanoid substrates. Structural analyses of the methylation products revealed that PfOMT3 regiospecifically transfers a methyl group to the 7-OH of flavonoids. These results indicate that PfOMT3 is an FOMT that catalyzes the 7-O-methylation of flavonoids. PfOMT3 methylated diverse flavonoids regardless of their backbone structure. Chrysin, naringenin and apigenin were found to be the preferred substrates of PfOMT3. Recombinant PfOMT3 showed moderate OMT activity toward eriodictyol, luteolin and kaempferol. To assess the biotechnological potential of PfOMT3, the biotransformation of flavonoids was performed using PfOMT3-transformed Escherichia coli. Naringenin and kaempferol were successfully bioconverted to the 7-methylated products sakuranetin and rhamnocitrin, respectively, by E. coli harboring PfOMT3.

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Section: Resultssupporting

confidence: 62%

Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production

Park

Lee

et al. 2020

Molecules

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“…However, it has neve been isolate in fresh-cut CWC before. As a flavonoids, eriodictyol has multiple chemical and biological properties, including antioxidant (Rossato et al, 2011), anti-inflammatory (Lee, 2011), antibacterial (Martins et al, 2015) and anticancer (Doostdar, Burke, & Mayer, 2000) activities, and thus it is a good candidate for a variety of applications for the food and pharmaceutical industry (Liu et al, 2013).…”

Section: Eriodictyol (Compound 1) C 15 H 12 Omentioning

confidence: 99%

Isolation, purification and identification of etiolation substrate from fresh-cut Chinese water-chestnut (Eleocharis tuberosa)

2015

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“…The fact that sterubin was only detected in a subset of the extracts that have eriodictyol and homoeriodictyol, confirms the possible involvement of a distinct 7-O-methyltransferase ( Figure 2J), whose expression may thus be susceptible to external conditions. The existence of specific OMTs for these flavanones has been previously documented (Kim et al, 2006;Shimizu et al, 2012;Liu et al, 2013;Lee et al, 2017).…”

Section: Flavonoid Measurementmentioning

confidence: 83%

“…In fact, several reports have identified the existence of regiospecific OMTs for these flavanones. This is the case of ROMT-9, an OMT from rice that can methylate the 3 -OH group of eriodictyol to generate homoeriodictyol (Kim et al, 2006;Liu et al, 2013), and of OsNOMT, another OMT from rice that can methylate the 7-OH group of eriodictyol to generate sterubin (Shimizu et al, 2012;Lee et al, 2017). The existence of a distinct 7OMT could explain why sterubin is only detected in some specimens within the same Eriodictyon species.…”

Section: Discussionmentioning

confidence: 99%

The Value of Herbarium Collections to the Discovery of Novel Treatments for Alzheimer’s Disease, a Case Made With the Genus Eriodictyon

et al. 2020

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Plants, in particular those with a history in traditional medicine, hold enormous potential as sources of new therapies for dementias such as Alzheimer's disease (AD). The largest collections of plants can be found in herbaria all over the world, but the value of these collections to AD drug discovery has been significantly neglected. As a proof of principle, we investigated the neuroprotective activity of herbarium specimens of Eriodictyon (yerba santa), a genus with a long history of usage by the indigenous tribes in California to treat respiratory and age-related complications. Dichloromethane extracts were prepared from leaves of 14 Eriodictyon taxa preserved in the SD Herbarium located at the San Diego Natural History Museum. The extracts were tested for neuroprotection in nerve cells against oxytosis and ferroptosis and for anti-inflammatory activity in brain microglial cells exposed to bacterial lipopolysaccharide. In parallel, the levels of the flavanones sterubin, eriodictyol and homoeriodictyol were measured by mass spectrometry. Several Eriodictyon species presented strong neuroprotective and antiinflammatory activities. The protective properties of the extracts correlated with the amount of sterubin, but not with eriodictyol or homoeriodictyol, indicating that sterubin is the major active compound in these species. The occurrence of eriodictyol and homoeriodictyol may be predictive of the phylogenetic relationship between members in the genus Eriodictyon. The data offer insight into the traditional use of yerba santa across indigenous tribes in California, while demonstrating the value of herbarium collections for the discovery of novel therapeutic compounds for the treatment of neurodegenerative diseases.

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Biosynthesis of homoeriodictyol from eriodictyol by flavone 3′-O-methyltransferase from recombinant Yarrowia lioplytica: Heterologous expression, biochemical characterization, and optimal transformation

Cited by 19 publications

References 22 publications

Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production

Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production

Isolation, purification and identification of etiolation substrate from fresh-cut Chinese water-chestnut (Eleocharis tuberosa)

The Value of Herbarium Collections to the Discovery of Novel Treatments for Alzheimer’s Disease, a Case Made With the Genus Eriodictyon

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