Feruloyl Sucrose Esters from Oryza sativa Roots and Their Tyrosinase Inhibition Activity

Cho, Jin‐Gyeong; Cha, Byeong-Ju; Seo, Woo-Duck; Jeong, Rak-Hun; Shrestha, Sabina; Kim, Jiyoung; Kang, Hee-Cheol; Baek, Nam‐In

doi:10.1007/s10600-015-1500-8

Cited by 13 publications

(13 citation statements)

References 21 publications

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“…Building on these promising in vitro bioactivities, organic synthesis routes to produce natural phenylpropanoid sucrose esters and structural analogs have been developed (Panda et al ., ,b). More recently, this class of metabolites has been found in rice (Chen et al ., ; Cho et al ., ). In the current study, two acetylated feruloylsucroses, smilaside A and smiglaside C, were shown to be induced by fungal infection in maize (Figs a–c, ).…”

Section: Discussionmentioning

confidence: 97%

“…f). This was perhaps surprising, because phenylpropanoid sucrose esters with higher degrees of acetylation had generally shown stronger in vitro bioactivities, although these two specific compounds had not been compared previously (Panda et al ., ; Cho et al ., ). Our observations suggest a more complex relationship between the degrees of acetylation and bioactivity, which may also be distinct between different structural isomers.…”

Section: Discussionmentioning

confidence: 97%

“…The exact order of feruloyl esterification and acetylation on the sucrose molecule also remains unclear. In rice, nonacetylated 3,6 diferuloylsucrose is detected at a very low concentration in bulk root extract, suggesting that the acetylation occurs after feruloyl esterification (Cho et al ., ). However, we did not detect the same compound in our microliter‐scale LC‐MS analyses of maize roots.…”

Section: Discussionmentioning

confidence: 97%

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Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

et al. 2018

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Summary The production and regulation of defensive specialized metabolites play a central role in pathogen resistance in maize (Zea mays) and other plants. Therefore, identification of genes involved in plant specialized metabolism can contribute to improved disease resistance. We used comparative metabolomics to identify previously unknown antifungal metabolites in maize seedling roots, and investigated the genetic and physiological mechanisms underlying their natural variation using quantitative trait locus mapping and comparative transcriptomics approaches. Two maize metabolites, smilaside A (3,6‐diferuloyl‐3′,6′‐diacetylsucrose) and smiglaside C (3,6‐diferuloyl‐2′,3′,6′‐triacetylsucrose), were identified that could contribute to maize resistance against Fusarium graminearum and other fungal pathogens. Elevated expression of an ethylene signaling gene, ETHYLENE INSENSITIVE 2 (ZmEIN2), co‐segregated with a decreased smilaside A : smiglaside C ratio. Pharmacological and genetic manipulation of ethylene availability and sensitivity in vivo indicated that, whereas ethylene was required for the production of both metabolites, the smilaside A : smiglaside C ratio was negatively regulated by ethylene sensitivity. This ratio, rather than the absolute abundance of these two metabolites, was important for maize seedling root defense against F. graminearum. Ethylene signaling regulates the relative abundance of the two F. graminearum‐resistance‐related metabolites and affects resistance against F. graminearum in maize seedling roots.

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Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 97%

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Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

et al. 2018

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“…3e). These two metabolites were previously identified as smilaside A (3,6 diferuloyl-3′,6′-diacetylsucrose) in Smilax china (Kuo et al , 2005; Cho et al , 2015) and smiglaside C (3,6 - diferuloyl-2′,3′,6′-triacetylsucrose) in Smilax glabra (Chen et al , 2000).…”

Section: Resultsmentioning

confidence: 99%

“…Building on these promising in vitro bioactivities, organic synthesis routes to produce natural phenylpropanoid sucrose esters and structural analogs have been developed with moderate yield and selectivity (Panda et al , 2012a; Panda et al , 2012b). More recently, acetylated feruloylsucroses and other phenylpropanoid sucrose esters were found in rice (Chen et al , 2014; Cho et al , 2015).…”

Section: Discussionmentioning

confidence: 99%

Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

Zhou

Zhang

Kremling

et al. 2018

Preprint

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SummaryThe production and regulation of defensive specialized metabolites plays a central role in pathogen resistance in maize (Zea mays) and other plants. Therefore, identification of genes involved in plant specialized metabolism can contribute to improved disease resistance.We used comparative metabolomics to identify previously unknown antifungal metabolites in maize seedling roots, and investigated the genetic and physiological mechanisms underlying their natural variation using quantitative trait locus (QTL) mapping and comparative transcriptomics approaches.Two maize metabolites, smilaside A (3,6-diferuloyl-3′,6′-diacetylsucrose) and smiglaside C (3,6-diferuloyl-2′,3′,6′-triacetylsucrose), that may contribute to maize resistance against Fusarium graminearum and other fungal pathogens were identified. Elevated expression of an ethylene receptor gene, ETHYLENE INSENSITIVE 2 (ZmEIN2), co-segregated with decreased smilaside A/smiglaside C ratio. Pharmacological and genetic manipulation of ethylene availability and sensitivity in vivo indicated that, whereas ethylene was required for the production of both metabolites, the smilaside A/smiglaside C ratio was negatively regulated by ethylene sensitivity. This ratio, rather than the absolute abundance of these two metabolites, was important for maize seedling root defense against F. graminearum.Ethylene signaling regulates the relative abundance of the two F. graminearum-resistance-related metabolites and affects resistance against F. graminearum in maize seedling roots.

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Isolation of phenylpropanoid sucrose esters from the roots of Persicaria orientalis and their potential as inhibitors of melanogenesis

et al. 2019

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Feruloyl Sucrose Esters from Oryza sativa Roots and Their Tyrosinase Inhibition Activity

Cited by 13 publications

References 21 publications

Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

Isolation of phenylpropanoid sucrose esters from the roots of Persicaria orientalis and their potential as inhibitors of melanogenesis

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