Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis

Li, Yuan; Lin, Huixin; Wang, Jian; Yang, Jian; Lai, Chang-Jiang-Sheng; Wang, Xing; Ma, Baowei; Tang, Jian; Li, Yong; Li, Xin-Lin; Guo, Juan; Gao, Wei; Huang, Luqi

doi:10.1021/acs.orglett.8b02146

Cited by 20 publications

(23 citation statements)

References 41 publications

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“…S5A). The previous study also found a similar transcript expression of UGT73AU1 in leaves and roots; however, UGT5 transcript expression in different tissues was not examined before (42)(43). To know whether UGT73AU1 and UGT5 contribute to developmental and tissuespecific C19-O-glucosylation of diterpenes, UGT73AU1 and UGT5 transcript expression was determined by qRT-PCR analysis, and correlated with diterpene accumulation patterns and UGT activity (Fig.…”

Section: Identification Of Candidate Ugt Of the Diterpene Pathwaymentioning

confidence: 83%

“…Overall, these results suggest a major role of ApUGT12 in planta biosynthesis of neoandrographolide. (42)(43). A comparison of amino acid sequences of ApUGT12, UGT73AU1 and UGT5 identified several conserved residues, besides the UDP-sugar binding PSPG motif and the catalytic histidine and aspartate residues, which might determine their substrate specificity (Fig.…”

Section: Virus-induced Gene Silencing Of Apugt12mentioning

confidence: 99%

“…However, UGT involved in developmental and tissue-specific biosynthesis of neoandrographolide was not identified. Previously, two methyl jasmonate (MeJA)–inducible UGTs (UGT73AU1 and UGT5), which catalyzed in vitro C19-O-glucosylation of andrograpanin, were identified, but their involvement in planta biosynthesis of neoandrographolide was not understood ( 42 , 43 ). To investigate the UGT involved in spatiotemporal biosynthesis of neoandrographolide, we have analyzed a large-scale transcriptome data of kalmegh and identified UGTs that preferentially expressed in neoandrographolide-accumulating tissues.…”

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confidence: 99%

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UGT86C11 is a novel plant UDP-glycosyltransferase involved in labdane diterpene biosynthesis

Srivastava

Garg

Misra

et al. 2021

Journal of Biological Chemistry

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Section: Identification Of Candidate Ugt Of the Diterpene Pathwaymentioning

confidence: 83%

Section: Virus-induced Gene Silencing Of Apugt12mentioning

confidence: 99%

mentioning

confidence: 99%

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UGT86C11 is a novel plant UDP-glycosyltransferase involved in labdane diterpene biosynthesis

Srivastava

Garg

Misra

et al. 2021

Journal of Biological Chemistry

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“…The structure of triterpenoid saponins consists of an oleanane-type triterpene skeleton with various sugar moieties (glucose, glucuronic acid, galactose, arabinose and xylose) attached to the hydroxyl and/or carboxyl groups and even other nucleophilic groups (-SH and -NH 2 ) [12]. 18β-GA is one of the most important oleanane-type triterpenoid sapogenins in G. uralensis , and most of the genes involved in its biosynthetic pathway have been successfully cloned and characterized, including β-amyrin synthetase (bAS) [13], cytochrome P450 monooxygenase 88D6 (CYP88D6) [14] and CYP72A154 [15] (figure 1).…”

Section: Introductionmentioning

confidence: 99%

GuUGT, a glycosyltransferase from Glycyrrhiza uralensis , exhibits glycyrrhetinic acid 3- and 30-O-glycosylation

Huang

Wang

et al. 2019

R. Soc. open sci.

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Glycyrrhiza uralensis is a well-known herbal medicine that contains triterpenoid saponins as the predominant bioactive components, and these compounds include glycyrrhetinic acid (GA)-glycoside derivatives. Although two genes encoding UDP-glycosyltransferases (UGTs) that glycosylate these derivates have been functionally characterized in G. uralensis, the mechanisms of glycosylation by other UGTs remain unknown. Based on the available transcriptome data, we isolated a UGT with expression in the roots of G. uralensis. This UGT gene possibly encodes a glucosyltransferase that glycosylates GA derivatives at the 3-OH site. Biochemical analyses revealed that the recombinant UGT enzyme could transfer a glucosyl moiety to the free 3-OH or 30-COOH groups of GA. Furthermore, engineered yeast harbouring genes involved in the biosynthetic pathway for GA-glycoside derivates produced GA-3-O-β-D-glucoside, implying that the enzyme has GA 3-O-glucosyltransferase activity in vivo. Our results could provide a frame for understand the function of the UGT gene family, and also is important for further studies of triterpenoids biosynthesis in G. uralensis.

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“…12 The biosynthesis of neoandrographolide is reported via glucosyltransferase (ApUGT)-catalyzed 19- O -glucosylation of andrograpanin. 13 It is soluble in methanol, ethanol, propanol, acetone, pyridine, and acetic acid. It is reported to be more a potent anti-inflammatory metabolite than andrographolide.…”

Section: Introductionmentioning

confidence: 99%

Carbohydrate Modifications of Neoandrographolide for Improved Reactive Oxygen Species-Mediated Apoptosis through Mitochondrial Pathway in Colon Cancer

et al. 2019

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Modifications at the carbohydrate moiety of neoandrographolide, isolated from the medicinal plant Andrographis paniculata, result in more potent and less toxic derivatives, namely, 4′,6′-benzylidene neoandrographolide (2b) and 4′6′-p-methoxybenzylidene neoandrographolide (2c). These showed improved cytotoxicity against SW-620, PC-3, and A549 cancer cell lines. Nuclear morphology studies were conducted on compound 2b by 4′,6-diamidino-2-phenylidole staining and detection of intracellular reactive oxygen species (ROS) accumulation. It showed an increase in the generation of cellular and mitochondrial ROS level. The probable relation of B-cell lymphoma-2 (Bcl-2, an apoptosis inhibitor) to B-cell lymphoma-2-associated X protein (Bax, an apoptosis promoter) ratio with caspase-3 (apoptosis coordination enzyme) in the colon cancer cell line SW-620 was investigated, and it was discovered that upon 2b treatment, the expression of caspase-3 Bax increased remarkably. However, in 2b-treated cells, the expression of Bcl-2 was downregulated as compared to untreated cells.

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Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis

Cited by 20 publications

References 41 publications

UGT86C11 is a novel plant UDP-glycosyltransferase involved in labdane diterpene biosynthesis

UGT86C11 is a novel plant UDP-glycosyltransferase involved in labdane diterpene biosynthesis

GuUGT, a glycosyltransferase from Glycyrrhiza uralensis , exhibits glycyrrhetinic acid 3- and 30-O-glycosylation

Carbohydrate Modifications of Neoandrographolide for Improved Reactive Oxygen Species-Mediated Apoptosis through Mitochondrial Pathway in Colon Cancer

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