Expanded investigations of the aglycon promiscuity and catalysis characteristic of flavonol 3-O-rhamnosyltransferase AtUGT78D1 from Arabidopsis thaliana

Mo, Ting; Liu, Xiao; Liu, Yuyu; Wang, Xiaohui; Zhang, Le; Wang, Juan; Zhang, Zhongxiu; Shi, She‐Po; Tu, Pengfei

doi:10.1039/c6ra16251g

Cited by 14 publications

(12 citation statements)

References 37 publications

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“…A cross peak is observed at 157.30 ppm, and belongs to C-7. The OCH 2 protons of the aliphatic chain were correlated with C-7 as shown in Figure 4 indicated that the aliphatic chain is bonded to the C-7 position [ 16 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Scutellarein Derivatives with a Long Aliphatic Chain and Their Biological Evaluation against Human Cancer Cells

Tang

et al. 2018

Molecules

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Scutellarin is the major active flavonoid extracted from the traditional Chinese herbal medicine Erigeron breviscapus (Vant.) Hand-Mazz., which is widely used in China. Recently, accumulating evidence has highlighted the potential role of scutellarin and its main metabolite scutellarein in the treatment of cancer. To explore novel anticancer agents with high efficiency, a series of new scutellarein derivatives with a long aliphatic chain were synthesized, and the antiproliferative activities against Jurkat, HCT-116 and MDA-MB-231 cancer cell lines were assessed. Among them, compound 6a exhibited the strongest antiproliferative effects on Jurkat (IC50 = 1.80 μM), HCT-116 (IC50 = 11.50 μM) and MDA-MB-231 (IC50 = 53.91 μM). In particular, 6a even showed stronger antiproliferative effects than the positive control NaAsO2 on Jurkat and HCT-116 cell lines. The results showed that a proper long aliphatic chain enhanced the antiproliferative activity of scutellarein.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Scutellarein Derivatives with a Long Aliphatic Chain and Their Biological Evaluation against Human Cancer Cells

Tang

et al. 2018

Molecules

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“…However, the enzymatic characterization of UDP-rhamnosyltransferases is still thwarted by the high costs of UDP-rhamnose (UDP-Rha). Despite important efforts in the establishment of efficient UDP-Rha production systems (Irmisch et al, 2018), only a few UDPrhamnosyltransferases have been functionally characterized, and enzymatic assays remain challenging (Mo et al, 2016, Irmisch et al, 2018. Here, we show that UGT91T1 shares a high degree of sequence similarity with functionally characterized rhamnosyltransferases for flavonoids and anthocyanins (CmF7G12RT, GmF3G6R, and PhA3ART-Supplemental Figure 6), is tightly and tissue-specifically co-regulated with the accumulation patterns of rhamnosylated HGL-DTGs, and exhibits strong co-expression with GLS, GGPPS, and UGT74P3.…”

Section: -Hgl-dtg Rhamnosyltransferase Activity Of Ugt91t1mentioning

confidence: 99%

Specific decorations of 17-hydroxygeranyllinalool diterpene glycosides solve the autotoxicity problem of chemical defense inNicotiana attenuata

Heiling

Llorca

et al. 2021

The Plant Cell

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The native diploid tobacco Nicotiana attenuata produces abundant, potent anti-herbivore defense metabolites known as 17-hydroxygeranyllinalool diterpene glycosides (HGL-DTGs) whose glycosylation and malonylation biosynthetic steps are regulated by jasmonate signaling. To characterize the biosynthetic pathway of HGL-DTGs, we conducted a genome-wide analysis of uridine diphosphate glycosyltransferases (UGTs) and identified 107 family-1 UGT members. The transcript levels of three UGTs were highly correlated with the transcript levels two key HGL-DTG biosynthetic genes: geranylgeranyl diphosphate synthase (NaGGPPS) and geranyllinalool synthase (NaGLS). NaGLS’s role in HGL-DTG biosynthesis was confirmed by virus-induced gene silencing. Silencing the UDP-rhamnosyltransferase gene UGT91T1 demonstrated its role in the rhamnosylation of HGL-DTGs. In vitro enzyme assays revealed that UGT74P3 and UGT74P4 use UDP-glucose for the glucosylation of 17-hydroxygeranyllinalool (17-HGL) to lyciumoside I. Plants with stable silencing of UGT74P3 and UGT74P5 were severely developmentally deformed, pointing to a phytotoxic effect of the aglycone. The application of synthetic 17-HGL and silencing of the UGTs in HGL-DTG-free plants confirmed this phytotoxic effect. Feeding assays with tobacco hornworm (Manduca sexta) larvae revealed the defensive functions of the glucosylation and rhamnosylation steps in HGL-DTG biosynthesis. Glucosylation of 17-HGL is therefore a critical step that contributes to the resulting metabolites’ defensive function and solves the autotoxicity problem of this potent chemical defense.

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“…Identifying and biochemically characterising some GT genes has helped in studying mechanism of glycosylation in planta . 21 Biochemical data on substrate preferences has been relied on for prediction of substrate specificity based on phylogeny. Till date, most of Arabidopsis thaliana UGTs substrates remain unknown.…”

Section: Introductionmentioning

confidence: 99%

High throughput mass spectrometry-based characterisation of Arabidopsis thaliana group H glycosyltransferases

Akere

Liu

et al. 2018

RSC Adv.

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Expanded investigations of the aglycon promiscuity and catalysis characteristic of flavonol 3-O-rhamnosyltransferase AtUGT78D1 from Arabidopsis thaliana

Abstract: Rhamnosides usually possess better bioavailabilities and improved solubilities compared with their aglycons and are a major source of bioactive natural products.

Cited by 14 publications

References 37 publications

Synthesis of Scutellarein Derivatives with a Long Aliphatic Chain and Their Biological Evaluation against Human Cancer Cells

Synthesis of Scutellarein Derivatives with a Long Aliphatic Chain and Their Biological Evaluation against Human Cancer Cells

Specific decorations of 17-hydroxygeranyllinalool diterpene glycosides solve the autotoxicity problem of chemical defense inNicotiana attenuata

High throughput mass spectrometry-based characterisation of Arabidopsis thaliana group H glycosyltransferases

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