New Feruloyl Tyramine Glycosides from Stephania hispidula YAMAMOTO

Yahagi, Tadahiro; Yamashita, Yumiko; Daikonnya, Akihiro; Wu, Jin‐Bin; Kitanaka, Susumu

doi:10.1248/cpb.58.415

Cited by 11 publications

(12 citation statements)

References 7 publications

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“…The majority of known phenylpropanoic acids has been described having trans configuration, although there are examples of cis configurated compounds. [38]…”

Section: Resultsmentioning

confidence: 99%

“…To the best of our knowledge, there has been only one other report describing identification of N -feruloyl tyramine glucosides from the unrelated plant, Stephania hispidula [38], from which both 4’- O and 4”’- O - glucosides of N -feruloyl tyramine were described. In the case of N -feruloyl methoxytyramine, a 4’-O-glucoside as well as a 4’-O-galactoside have been identified.…”

Section: Resultsmentioning

confidence: 99%

“…In the case of N -feruloyl methoxytyramine, a 4’-O-glucoside as well as a 4’-O-galactoside have been identified. [38, 39] The galactoside analog, known as cimicifugamide, was identified in a related plant Cimicifuga dahurica [39], making it likely that 69 is a galactoside based on chemotaxonomic considerations. However, the position of glycosidation for these compounds is different from the proposed structure of 69 .…”

Section: Resultsmentioning

confidence: 99%

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Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

et al. 2012

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Black cohosh preparations are popular dietary supplements among women seeking alternative treatments for menopausal complaints. For decades, triterpene glycosides and phenolic acids have dominated the phytochemical and biomedical research on this plant. In this study, we provide evidence that black cohosh contains an unexpected and highly diverse group of secondary nitrogenous metabolites previously unknown to exist in this plant. Using a dereplication approach that combines accurate mass measurements, database searches and general knowledge of biosynthetic pathways of natural products, we identified or tentatively identified 73 nitrogen-containing metabolites, many of which are new natural products. The identified compounds belong to several structural groups including alkaloids, amides or esters of hydroxycinnamic acids and betains. Among the alkaloids, several classes such as guanidino alkaloids, isoquinolines and β-carbolines were identified. Fragmentation patterns for major compound classes are discussed, which provides a framework for the discovery of these compounds from other sources. Identification of alkaloids as a well-known group of bioactive natural products represents an important advance in better understanding of the pharmacological profile of black cohosh.

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“…The majority of known phenylpropanoic acids has been described having trans configuration, although there are examples of cis configurated compounds. [38]…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

et al. 2012

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“…It is assumed that its main function in plants is to strengthen the cell walls and therefore prevent the entry of pathogens into suberizing tissue. The biosynthesis of hydroxycinnamoyl amides has been well studied, but a UGT capable of glucosylating phytoalexins has not been reported to date, although glucosides of the amides have been frequently found (Yahagi et al, 2010;Bolleddula et al, 2012;Nikoli c et al, 2012Nikoli c et al, , 2015Yang et al, 2012;Yim et al, 2012;Zhang et al, 2013;Pei et al, 2015;Geng et al, 2017;Oliveira de Silva and Batista, 2017;Wang et al, 2017). The biological function of glucosides of hydroxycinnamoyl amides is unclear but they might play a similar role like monolignol glucosides in plant defence (Le Roy et al, 2016).…”

Section: Accumulation Of N-feruloyl Tyramine Glucoside After Agroinfimentioning

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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“…However, the determination of the glycosidation position is a very challenging task. Although the isolated hexosides of HCAA from Actaea plants were found to be 4- O -hexosides exclusively, both 4- O and 4′- O -hexosides have been described in other plants [37]. The hexosylated acylium ion of ferulic acid at m/z 339 and its water-loss ion at m/z 321 of V9b and V9c are evidence of 4- O -hexosides; but their lack of presence can not be the proof of 4′- O -hexosides in V9.…”

Section: Resultsmentioning

confidence: 99%

Feruloyl dopamine-O-hexosides are efficient marker compounds as orthogonal validation for authentication of black cohosh (Actaea racemosa)—an UHPLC-HRAM-MS chemometrics study

et al. 2017

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Due to the complexity and variation of the chemical constituents in authentic black cohosh (Actaea racemosa) and its potential adulterant species, an accurate and feasible method for black cohosh authentication is not easy. A high resolution accurate mass (HRAM) LC-MS fingerprinting method combined with chemometric approach was employed to discover new marker compounds. Seven hydroxycinnamic acid amide (HCAA) glycosides are proposed as potential marker compounds for differentiation of black cohosh from related species, including two Asian species (A. foetida, A. dahurica) and two American species (A. pachypoda, A. podocarpa). These markers were putatively identified by comparing their mass spectral fragmentation behavior with those of their authentic aglycone compounds and phytochemistry reports. Two isomers of feruloyl methyldopamine 4-O-hexoside ([M+H]+ 506) and one feruloyl tyramine 4-O-hexoside ([M+H]+ 476) contributed significantly to the separation of Asian species in principle component analysis (PCA) score plot. The efficacy of the models built on four reasonable combinations of these markers in differentiating black cohosh and its adulterants were evaluated and validated by partial least-square discriminant analysis (PLS-DA). Two models based on these reduced dataset achieved 100% accuracy based on the current sample collection, including the model that used only three feruloyl dopamine-O-hexoside isomers ([M+H]+ 492) and one feruloyl dopamine-O-dihexoside ([M+H-hexosyl]+ at m/z 492).

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New Feruloyl Tyramine Glycosides from Stephania hispidula YAMAMOTO

Cited by 11 publications

References 7 publications

Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

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

Feruloyl dopamine-O-hexosides are efficient marker compounds as orthogonal validation for authentication of black cohosh (Actaea racemosa)—an UHPLC-HRAM-MS chemometrics study

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