Involvement of three putative glucosyltransferases from the UGT72 family in flavonol glucoside/rhamnoside biosynthesis in<i>Lotus japonicus</i>seeds

Yin, Qinggang; Shen, Guoan; Chang, Zhenzhan; Tang, Yuhong; Gao, Hong‐Wen; Pang, Yongzhen

doi:10.1093/jxb/erw420

Cited by 38 publications

(60 citation statements)

References 63 publications

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“…that are more than 250 amino acids in length) (Table S15). Although this is less than the number of characterized UGT genes in Arabidopsis thaliana (120), Medicago truncatula (187), Cypripedium arietinum (125), Glycine max (242), Gossypium hirsutum (196) and Lotus japonicus (188) (Yonekura‐Sakakibara and Hanada, ; Huang et al ., ; Yin et al ., ), it may reflect less glycoslation in this plant species or the incomplete nature of the draft genome assembly. The full‐length A. paniculata UGT genes were named based on the accepted naming convention for signature PSPG motifs (http://prime.vetmed.wsu.edu/resources/udp-glucuronsyltransferase-homepage) (Mackenzie et al ., ).…”

Section: Resultsmentioning

confidence: 96%

The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide

et al. 2019

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These authors contributed equally to this work. ‡ These authors are corresponding co-authors. SUMMARYAndrographis paniculata is a herbaceous dicot plant widely used for its anti-inflammatory and anti-viral properties across its distribution in China, India and other Southeast Asian countries. A. paniculata was used as a crucial therapeutic treatment during the influenza epidemic of 1919 in India, and is still used for the treatment of infectious disease in China. A. paniculata produces large quantities of the anti-inflammatory diterpenoid lactones andrographolide and neoandrographolide, and their analogs, which are touted to be the next generation of natural anti-inflammatory medicines for lung diseases, hepatitis, neurodegenerative disorders, autoimmune disorders and inflammatory skin diseases. Here, we report a chromosome-scale A. paniculata genome sequence of 269 Mb that was assembled by Illumina short reads, PacBio long reads and high-confidence (Hi-C) data. Gene annotation predicted 25 428 protein-coding genes. In order to decipher the genetic underpinning of diterpenoid biosynthesis, transcriptome data from seedlings elicited with methyl jasmonate were also obtained, which enabled the identification of genes encoding diterpenoid synthases, cytochrome P450 monooxygenases, 2-oxoglutarate-dependent dioxygenases and UDP-dependent glycosyltransferases potentially involved in diterpenoid lactone biosynthesis. We further carried out functional characterization of pairs of class-I and -II diterpene synthases, revealing the ability to produce diversified labdane-related diterpene scaffolds. In addition, a glycosyltransferase able to catalyze O-linked glucosylation of andrograpanin, yielding the major active product neoandrographolide, was also identified. Thus, our results demonstrate the utility of the combined genomic and transcriptomic data set generated here for the investigation of the production of the bioactive diterpenoid lactone constituents of the important medicinal herb A. paniculata.

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Section: Resultsmentioning

confidence: 96%

The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide

et al. 2019

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“…This group includes the ABA glucosyltransferase UGT71B6 (Yonekura‐Sakakibara and Hanada, ) and UGT71G1 from Medicago truncatula , which can glycosylate flavonoids and triterpenoids (medicagenic acid, hederagenin; Shao et al ., ). Similarly, members of the UGT72 subfamily have been shown to function in flavonol (Yin et al ., ), flavanone, anthocyanin (Zhao et al ., ) and monolignol glucosylation (Lim et al ., ; Lanot et al ., ) and are probably involved in lignin biosynthesis (Wang et al ., ). Members of the UGT73 subfamily catalyzed the 3‐ O ‐glucosylation of the sapogenins oleanolic acid and hederagenin (Augustin et al ., ; Erthmann et al ., ) and the modification of the brassinosteroid phytohormones (Poppenberger et al ., ), while UGT73C6 transferred glucose from UDP‐glucose to the 7‐OH position of kaempferol 3‐ O ‐rhamnoside and quercetin 3‐ O ‐rhamnoside, respectively (Jones et al ., ) and UGT73B3 and UGT73B5 are implicated in the modification of salicylic acid and scopoletin (Simon et al ., ).…”

Section: Discussionmentioning

confidence: 99%

Glucosylation of the phytoalexin N‐feruloyl tyramine modulates the levels of pathogen‐responsive metabolites in Nicotiana benthamiana

et al. 2019

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Summary Enzyme promiscuity, a common property of many uridine diphosphate sugar‐dependent glycosyltransferases (UGTs) that convert small molecules, significantly hinders the identification of natural substrates and therefore the characterization of the physiological role of enzymes. In this paper we present a simple but effective strategy to identify endogenous substrates of plant UGTs using LC‐MS‐guided targeted glycoside analysis of transgenic plants. We successfully identified natural substrates of two promiscuous Nicotiana benthamiana UGTs (NbUGT73A24 and NbUGT73A25), orthologues of pathogen‐induced tobacco UGT (TOGT) from Nicotiana tabacum, which is involved in the hypersensitive reaction. While in N. tabacum, TOGT glucosylated scopoletin after treatment with salicylate, fungal elicitors and the tobacco mosaic virus, NbUGT73A24 and NbUGT73A25 produced glucosides of phytoalexin N‐feruloyl tyramine, which may strengthen cell walls to prevent the intrusion of pathogens, and flavonols after agroinfiltration of the corresponding genes in N. benthamiana. Enzymatic glucosylation of fractions of a physiological aglycone library confirmed the biological substrates of UGTs. In addition, overexpression of both genes in N. benthamiana produced clear lesions on the leaves and led to a significantly reduced content of pathogen‐induced plant metabolites such as phenylalanine and tryptophan. Our results revealed some additional biological functions of TOGT enzymes and indicated a multifunctional role of UGTs in plant resistance.

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“…The UGT family of G. max [36,41,46] and L. japonicus [47] has been described previously. We did not go for a detailed comparison with the results of Yin et al [46,47] because of discrepancies in the screening criteria of those studies (e.g., they considered all proteins having PSPG motif as UGTs irrespective of the protein length) with that of the current study. Though Caputi et al [36] and Rehman et al [41] utilized the first genome version of G. max, the former identified 183 UGTs while the latter identified 149 UGTs.…”

Section: Genome-wide Identification Of Ugt Gene Family In Five Papilimentioning

confidence: 99%

Reconstruction of the Evolutionary Histories of UGT Gene Superfamily in Legumes Clarifies the Functional Divergence of Duplicates in Specialized Metabolism

Krishnamurthy

Tsukamoto

Ishimoto

2020

IJMS

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Plant uridine 5′-diphosphate glycosyltransferases (UGTs) influence the physiochemical properties of several classes of specialized metabolites including triterpenoids via glycosylation. To uncover the evolutionary past of UGTs of soyasaponins (a group of beneficial triterpene glycosides widespread among Leguminosae), the UGT gene superfamily in Medicago truncatula, Glycine max, Phaseolus vulgaris, Lotus japonicus, and Trifolium pratense genomes were systematically mined. A total of 834 nonredundant UGTs were identified and categorized into 98 putative orthologous loci (POLs) using tree-based and graph-based methods. Major key findings in this study were of, (i) 17 POLs represent potential catalysts for triterpene glycosylation in legumes, (ii) UGTs responsible for the addition of second (UGT73P2: galactosyltransferase and UGT73P10: arabinosyltransferase) and third (UGT91H4: rhamnosyltransferase and UGT91H9: glucosyltransferase) sugars of the C-3 sugar chain of soyasaponins were resulted from duplication events occurred before and after the hologalegina–millettoid split, respectively, and followed neofunctionalization in species-/ lineage-specific manner, and (iii) UGTs responsible for the C-22-O glycosylation of group A (arabinosyltransferase) and DDMP saponins (DDMPtransferase) and the second sugar of C-22 sugar chain of group A saponins (UGT73F2: glucosyltransferase) may all share a common ancestor. Our findings showed a way to trace the evolutionary history of UGTs involved in specialized metabolism.

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Involvement of three putative glucosyltransferases from the UGT72 family in flavonol glucoside/rhamnoside biosynthesis inLotus japonicusseeds

Abstract: HighlightThe UGT72 family is a major group of UDP-glycosyltransferases with diverse substrates. UGT72AD1, UGT72AH1, and UGT72Z2 may be involved in flavonol rhamnoside biosynthesis in seeds of Lotus japonicus.

Cited by 38 publications

References 63 publications

The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide

The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide

Glucosylation of the phytoalexin N‐feruloyl tyramine modulates the levels of pathogen‐responsive metabolites in Nicotiana benthamiana

Reconstruction of the Evolutionary Histories of UGT Gene Superfamily in Legumes Clarifies the Functional Divergence of Duplicates in Specialized Metabolism

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