Separation and isolation of saturated and unsaturated 5-n-alk(en)ylresorcinols from rye bran

Patzke, Hannes; Schulze-Kaysers, Nadine; Schieber, Andreas

doi:10.1016/j.chroma.2016.01.057

Cited by 8 publications

(5 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Interestingly, the AR-C17 contents in TB and WB were marked higher, which were quite different from the contents of polyphenols and flavonoids in the four grain bran extracts. Since our results were consistent with those already reported, 9 AR-C17 extracted from TB and WB were used for the followup test.…”

Section: Pharmacokinetic Study In Mice Plasma and Excretionsupporting

confidence: 91%

“…ARs are abundantly present in various higher plants of different families, with an especially higher proportion observed in cereal crops, and are typically saturated in the range of 17–25 carbon atoms (Table ). − It is reported that ARs were mainly observed in triticale and wheat while presenting a relatively low level in barley and oat . Notably, a number of previous reports have concluded that ARs in grains are predominantly present in the bran rather than in embryos and endosperms.…”

Section: Introductionmentioning

confidence: 97%

“…6−8 It is reported that ARs were mainly observed in triticale and wheat while presenting a relatively low level in barley and oat. 9 Notably, a number of previous reports have concluded that ARs in grains are predominantly present in the bran rather than in embryos and endosperms. Moreover, ARs have been seen as a biomarker for whole grain consumption, and in the bran-free diet, AR typical metabolites such as 3,5-dihydroxybenzoic acid (DHBA) and 3-(3,5-dihydroxyphenyl) propanoic acid (DHPPA) were measured.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Quercetin Enhances the Availability of 5-Heptadecylresorcinol by Inhibiting the Expression of P-gp

Jiang,

Zhang,

Fan

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

5-Heptadecylresorcinol (AR-C17), as the most important active monomer, is found in large quantities in wheat and triticale and plays a variety of health benefits, such as antidiabetic, anti-inflammatory, and antitumor. However, the low bioavailability of AR-C17 due to its low water solubility restricts its application. Moreover, the transport mechanism of AR-C17 is not fully understood. Here, we showed that the transport of AR-C17 in vitro was time- and concentration-dependent, and relatively higher temperature and lower pH obviously promoted the transport of AR-C17. Besides, transporters, especially P-glycoprotein (P-gp), markedly affected the transport of AR-C17 as well. Quercetin, a natural synergist in triticale bran (TB), was confirmed as an inhibitor of P-gp to promote the transport of AR-C17 in this study, and the bioavailability of AR-C17 reached the highest when the concentration ratio of quercetin to AR-C17 was 1:1.

show abstract

Section: Pharmacokinetic Study In Mice Plasma and Excretionsupporting

confidence: 91%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Quercetin Enhances the Availability of 5-Heptadecylresorcinol by Inhibiting the Expression of P-gp

Jiang,

Zhang,

Fan

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The aim of our study was the isolation of the most relevant saturated ARs (AR17:0-AR25:0) from rye in high purity. Previous studies on the isolation of ARs were based on semi-preparative HPLC after low-temperature fractionation at −80 • C [14] or TLC using argentation chromatography followed by HPLC [8,15,16]. While several ARs can be commercially ordered (>300 €/10 mg; November 2020), purities are only ∼95%.…”

Section: Introductionmentioning

confidence: 99%

Isolation of saturated alkylresorcinols from rye grains by countercurrent chromatography

Hammerschick

Wagner

Vetter

2021

J of Separation Science

View full text Add to dashboard Cite

Alkylresorcinols (5-alkyl-1,3-dihydroxybenzenes) are amphiphilic phenolic lipid compounds that are abundant in cereals with highest contents in rye. Alkylresorcinols are suspected to show a wide range of favourable biological activities.For such and further testing, highly pure alkylresorcinol standards are required. Especially, purities >> 98% were partly difficult to obtain in the past. Here, we aimed to isolate the most abundant (saturated) alkylresorcinols from rye using countercurrent chromatography. To achieve very high purity, alkylresorcinolcontaining extract (∼7.14 g) of rye grains (cold extracts with cyclohexane/ethyl acetate (46/54, w/w)) were preparatively transesterified followed by a preparative hydrogenation. Countercurrent chromatography separation of ∼1 g hydrogenated and transesterified rye grain extract using the solvent system n-hexaneethyl acetate-methanol-water (9:1:9:1, v/v/v/v) yielded 51.8 mg AR17:0, 77.4 mg AR19:0, 57.2 mg AR21:0, 28.8 mg AR23:0 and 11.5 mg AR25:0 with purities >99% in either case. The isolated alkylresorcinol homologues can be used for subsequent bioassays.

show abstract

“…Aktivität, weshalb von einer Detoxifizierung der phenolischen Säuren ausgegangen werden kann [2]. Aus Getreidekleie isolierte Alk(en)ylresorcine zeigen antifungale Eigenschaften gegen mehrere Fusarien-Spezies [3,4].…”

unclassified

Verwertung von Nebenströmen als Beitrag zu nachhaltiger Lebensmittelproduktion: Auf dem Weg vom Reststoff zum natürlichen Zusatzstoff

Schieber

2023

Lebensmittelchemie

View full text Add to dashboard Cite

Separation and isolation of saturated and unsaturated 5-n-alk(en)ylresorcinols from rye bran

Cited by 8 publications

References 19 publications

Quercetin Enhances the Availability of 5-Heptadecylresorcinol by Inhibiting the Expression of P-gp

Quercetin Enhances the Availability of 5-Heptadecylresorcinol by Inhibiting the Expression of P-gp

Isolation of saturated alkylresorcinols from rye grains by countercurrent chromatography

Verwertung von Nebenströmen als Beitrag zu nachhaltiger Lebensmittelproduktion: Auf dem Weg vom Reststoff zum natürlichen Zusatzstoff

Contact Info

Product

Resources

About