Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family?

Baumert, A.; Milkowski, Carsten; Schmidt, Jürgen; Nimtz, Manfred; Wray, Victor; Strack, Dieter

doi:10.1016/j.phytochem.2005.02.031

Cited by 99 publications

(119 citation statements)

References 33 publications

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“…Next, dihexoside moiety (2 9 162 amu = 324 amu) is lost which gives rise to a deprotonated kaempferol ion (m/z 285.0403) as a base peak. This kind of fragmentation indicates the occurrence of glycosylation in accordance with literature data which show that in Brassica species, only sugar moieties such as glucose and rhamnose are predominantly bound in positions -7 [19,32,33,35,36]. In the disaccharide moieties present in analyzed compounds [2,3,5, and 6 (Table 1)] after fragmentation, the loss of 324 amu and low abundance of 162 amu selon occur, which, according to Ferreres et al [31], corresponds to a diglucoside with a 1-6 linkage, that is, gentiobioside.…”

Section: Resultssupporting

confidence: 90%

Application of ultra performance liquid chromatography-photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS) method for the characterization of phenolic compounds of Lepidium sativum L. sprouts

Oszmiański

Kolniak‐Ostek

2013

Eur Food Res Technol

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Some of health-protecting phytochemicals can be found in the sprouts in a much higher concentration than in the developed plants. However, the polyphenol composition of Lepidium sativum L. sprouts is still unresolved, especially with regard to flavonoids and phenolic acids. To develop a rapid and reliable UPLC-PDA-Q/TOF-MS method for the identification and quantification of main flavonoids and phenolic acids from L. sativum sprouts, the samples of L. sativum sprouts were grown with and without the exposition to light. Ten phenolic compounds were identified on the basis of their mass spectra in MS mode, MS/MS spectra, PDA spectrum, and retention times as compared with available reference substances. The major compounds were found to be sinapic acid derivatives. Acylated flavonoids in L. sativum sprouts were identified as kaempferol and quercetin with the same glycosidic substitution pattern as the major compounds, and varying degrees of acylation with sinapic and ferulic acids. Total content of phenolics in both samples was similar, but the content of flavonoids was higher and sinapine was lower in the sample of sprouts germinated in light. The determination and the evaluation of L. sativum extracts is very effective while using the UPLC-PDA-Q/TOF-MS. Even though the substances only occur in low concentrations, the combination of the retention time and the accurate molecular mass allows for their fast qualification.

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Section: Resultssupporting

confidence: 90%

Application of ultra performance liquid chromatography-photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS) method for the characterization of phenolic compounds of Lepidium sativum L. sprouts

Oszmiański

Kolniak‐Ostek

2013

Eur Food Res Technol

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“…Replicate blots probed with pre-immune sera did not result in the detection of any bands. substrate, as has been shown for other plant SCPL acyltransferase enzymes (Shirley and Chapple, 2003;Baumert et al, 2005;Stehle et al, 2008). We further show by functional analysis that SCPL1 is able to catalyze the formation of avenacin A-1 from des-acyl avenacin A and N-methyl anthraniloyl-O-glucose.…”

Section: Discussionsupporting

confidence: 80%

“…The levels of this compound were clearly elevated in sad7 root extracts compared with extracts from roots of the wild type and sad1 mutants ( Figure 6B). These results suggest that SCPL1, like the other characterized dicot SCPL acyltransferases (Shirley and Chapple, 2003;Baumert et al, 2005;Stehle et al, 2008), uses an O-glucose ester as the acyl donor substrate.…”

Section: Scpl1 Is Synonymous With Sad7mentioning

confidence: 71%

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A Serine Carboxypeptidase-Like Acyltransferase Is Required for Synthesis of Antimicrobial Compounds and Disease Resistance in Oats

et al. 2009

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Serine carboxypeptidase-like (SCPL) proteins have recently emerged as a new group of plant acyltransferases. These enzymes share homology with peptidases but lack protease activity and instead are able to acylate natural products. Several SCPL acyltransferases have been characterized to date from dicots, including an enzyme required for the synthesis of glucose polyesters that may contribute to insect resistance in wild tomato (Solanum pennellii) and enzymes required for the synthesis of sinapate esters associated with UV protection in Arabidopsis thaliana. In our earlier genetic analysis, we identified the Saponin-deficient 7 (Sad7) locus as being required for the synthesis of antimicrobial triterpene glycosides (avenacins) and for broad-spectrum disease resistance in diploid oat (Avena strigosa). Here, we report on the cloning of Sad7 and show that this gene encodes a functional SCPL acyltransferase, SCPL1, that is able to catalyze the synthesis of both N-methyl anthraniloyl-and benzoyl-derivatized forms of avenacin. Sad7 forms part of an operon-like gene cluster for avenacin synthesis. Oat SCPL1 (SAD7) is the founder member of a subfamily of monocot-specific SCPL proteins that includes predicted proteins from rice (Oryza sativa) and other grasses with potential roles in secondary metabolism and plant defense.

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“…However, nothing has been reported about tronchuda cabbage seeds. In fact, several studies with other Brassica species have reported the existence of phenolics in the seeds, namely phenolic acids and their derivatives (Baumert et al, 2005;Bouchereau, Hamelin, Lamour, Renard, and Larher, 1991;Li and El Rassi, 2002;Naczk, Amarowicz, Sullivan, and Shahidi, 1998), flavonoid glycosides (Baumert et al, 2005) and tannins (Naczk et al, 1998). These compounds have been considered as UV screens in young seedlings (Gitz, Liu, and McClure, 1998) and have been associated with seedling vigour, height and weight (Randhir and Shetty, 2003;Randhir and Shetty, 2005).…”

Section: Introductionmentioning

confidence: 99%

Tronchuda cabbage (Brassica oleracea L. var. costata DC) seeds: Phytochemical characterization and antioxidant potential

et al. 2007

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Tronchuda cabbage (Brassica oleracea L. var. costata DC) seeds were studied for their chemical composition and antioxidant capacity. Thirteen phenolic compounds were characterized and quantified by reversed-phase HPLC-DAD-MS/MS-ESI and HPLC-DAD, respectively: two sinapoylgentiobiose isomers, three sinapoylglucose isomers, kaempferol-3-(sinapoyl)sophorotrioside-7-glucoside, sinapoylcholine, kaempferol-3,7-diglucoside-4 0 -(sinapoyl)glucoside, three disinapoylgentiobiose isomers, 1,2,2 0 -trisinapoylgentiobiose and 1,2-disinapoylglucose. Seven organic acids (aconitic, citric, ascorbic, malic, quinic, shikimic and fumaric acids) were also identified and quantified by HPLC-UV. The aqueous extract of tronchuda cabbage seeds was investigated for its capacity to act as a scavenger of DPPH Å radical and reactive oxygen species (superoxide radical, hydroxyl radical and hypochlorous acid), exhibiting antioxidant capacity in a concentration-dependent manner against all radicals. These results may be attributed to the high content of hydroxycinnamic derivatives and ascorbic acid.

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Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family?

Cited by 99 publications

References 33 publications

Application of ultra performance liquid chromatography-photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS) method for the characterization of phenolic compounds of Lepidium sativum L. sprouts

Application of ultra performance liquid chromatography-photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS) method for the characterization of phenolic compounds of Lepidium sativum L. sprouts

A Serine Carboxypeptidase-Like Acyltransferase Is Required for Synthesis of Antimicrobial Compounds and Disease Resistance in Oats

Tronchuda cabbage (Brassica oleracea L. var. costata DC) seeds: Phytochemical characterization and antioxidant potential

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