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4 Originalarbeiten 4.1 Phenolic Composition of Rhubarb Krafczyk, N.; Kötke, M.; Lehnert, N

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4 Originalarbeiten 4.1 Phenolic Composition of Rhubarb Krafczyk, N.; Kötke, M.; Lehnert, N Originalarbeiten 43 4 Originalarbeiten 4.1 Phenolic Composition of Rhubarb Krafczyk, N.; Kötke, M.; Lehnert, N. and Glomb, M.A. Phenolic Composition of Rhubarb. European Food Research and Technology 2008, angenommen am 01.07.2008. Eur Food Res Technol DOI 10.1007/s00217-008-0922-y ORIGINAL PAPER Phenolic composition of rhubarb Nicole Krafczyk · Matthias Kötke · Nicole Lehnert · Marcus A. Glomb Received: 29 April 2008 / Revised: 25 June 2008 / Accepted: 1 July 2008 © Springer-Verlag 2008 Abstract Extracts of diVerent parts (leaves, petioles and Introduction rhizomes) of domestic garden rhubarb (hybrids of Rheum rhabarbarum L. and Rheum rhaponticum L.) were investi- Rhubarb belongs to the family of Polygonaceae. It is gated for their content of phenolic ingredients. Two stilb- widely used as a traditional Chinese medicinal herb. There enes (trans-rhapontigenin, trans-desoxyrhapontigenin), are approximately 50 various kinds of rhubarb (Rheum spe- Wve stilbene glycosides (trans-rhaponticin, cis- and trans- cies), e.g., R. palmatum L., R. rhaponticum L., R. oYcinale desoxyrhaponticin, trans-resveratrol-4Ј-O--D-glucopyran- L., R. undulatum L. (syn. R. rhabarbarum L.), R. emodi L. oside, trans-piceatannol-3Ј-O--D-glucopyranoside) and and R. ribesformicum L. [1]. Botanically, it is diYcult to seven Xavonoids [rutin, quercetin-3-O-glucuronide, isovit- distinguish between the various Rheum species. Recent exin, 6,8-di-C--D-glucosylapigenin, 6-C--D-glucosyl-8- studies on the constituents of rhubarb (leaves and rhizoms) C--D-arabinosylapigenin (schaftoside), 6-C--D-arabino- have revealed the occurrence of a variety of phenolic com- syl-8-C--D-glycosylapigenin (isoschaftoside), (+)-cate- pounds, i.e., anthracene derivatives (which are the active chin] were unequivocally established. Separation was done principles of the purgative eVect) [2, 3], naphthalene deriv- in two steps. Multilayer countercurrent chromatography atives [4], stilbene glycosides [5, 6], tannin-related com- was applied to separate diVerent extracts of plant material. pounds such as galloyl esters of glucose [7], Xavonols [8], Preparative HPLC was then used to obtain pure substances. catechine derivatives [5, 9] and anthocyanins [10]. The var- The purity and identity of isolated compounds was ious kinds of rhubarb contain diVerent types of phenolic conWrmed by diVerent NMR experiments, HR-MS and ingredients. R. palmatum L. and R. oYcinale L. have HPLC-DAD analysis. anthraquinones and anthraquinone-glycosides. R. rhaponti- cum L. and R. ribesformicum L. possess stilbenes, such as Keywords Rhubarb · Multilayer countercurrent rhaponticosides, which induce phytoestrogenic eVects [11]. chromatography (MLCCC) · Phenolic compounds · Most botanical gardens in Europe cultivate species of the NMR · HPLC-DAD · HR-MS section rhaponticum. The species of this section hybridize with great ease, thus, nowadays there are no pure species of this section in cultivation in Europe [12]. The commercial garden rhubarb is a crossbreed between R. rhabarbarum L. and R. rhaponticum L. [13]. Ingredients of traditional Chinese rhubarb (R. oYcinale) were studied in-depth. In contrast, the polyphenolic ingre- dients of garden rhubarb, cultivated in Europe, were char- acterized very scarcely. Therefore, the aim of this study N. Krafczyk · M. Kötke · N. Lehnert · M. A. Glomb (&) was to isolate polyphenols from the rhizome, petioles and Institute of Chemistry, Food Chemistry, leaves of garden rhubarb by MLCCC and preparative Martin Luther University Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120 Halle, Germany HPLC. MLCCC has been successfully applied to analysis e-mail: [email protected] and separation of various natural products [14]. 123 Eur Food Res Technol Materials and methods Analytical HPLC-DAD Chemicals A Jasco (Gross-Umstadt, Germany) quaternary gradient unit PU 2080, with degasser DG 2080-54, autosampler AS Chemicals of highest quality available were obtained from 2055, column oven (Jasco Jetstream II) and multiwave- Roth (Karlsruhe, Germany) unless otherwise indicated. length detector MD 2015 was used. Chromatographic sepa- Methanol was HPLC-grade from Merck (Darmstadt, rations were performed on stainless steel columns Germany). HeptaXuorobutyric acid and (+)-catechin were (VYDAC CRT. #218TP54, 250 £ 4.0 mm, RP 18, 5 m, purchased from Fluka (Taufkirchen, Germany). Dimethyl- Hesperia, CA) using a Xow rate of 1.0 mL min¡1. The sulfoxide (DMSO-d6) was obtained from Chemotrade mobile phase used was water (solvent A) and MeOH/water (Leipzig, Germany). (7:3 v/v, solvent B). To both solvents (A and B), 0.6 mL L¡1 heptaXuorobutyric acid (HFBA) was added. Extraction of plant material Samples were injected at 10% B, the gradient then changed linear to 30% B in 30 min, to 65% B in 40 min, to 100% B Rhubarb rhizomes, leaves and petioles were obtained in 2 min, and held at 100% B for 8 min. The column tem- from local gardens in Germany (Sachsen-Anhalt and perature was 25 °C. The eZuent was monitored at 280 nm, Brandenburg). Hundred grams of freeze-dried and 350 nm. material was extracted with acetone/water (7:3 v/v) at 5 °C for 24 h under argon atmosphere, and decanted. Preparative HPLC-UV Acetone was removed under reduced pressure. The residual H2O phase was successively extracted A Besta HD 2–200 pump (Wilhelmsfeld, Germany) was with diethyl ether (2 £ 200 mL), ethyl acetate (2 £ used at a Xow rate of 8 mL min¡1. Elution of material was 200 mL) and n-butanol (2 £ 200 mL). From the individ- monitored by a UV-detector (Jasco UV-2075, Gross-Ums- ual extracts solvents were removed under reduced tadt, Germany). Chromatographic separations were per- pressure. formed on stainless steel columns (VYDAC CRT. #218TP1022, 250 £ 23 mm, RP18, 10 m, Hesperia, CA). Multilayer countercurrent chromatography The mobile phase used was solvent A and B identical to the analytical HPLC-DAD system. From the individual chro- The Multilayer countercurrent chromatography matographic fractions solvents were removed under (MLCCC) system (Ito, Multilayer Separator–Extractor reduced pressure. After addition of water solutions of poly- Modell, P·C. Inc., Potomac) was equipped with a Waters phenols were freeze-dried. constant Xow pump (model 6000 A), a Zeiss Spectralpho- tometer PM2D operating at 280 nm, a sample injection Accurate mass determination (HR-MS) valve with a 10-mL sample loop. Eluted liquids were col- lected in fractions of 8 mL with a fraction collector (LKB The high resolution positive and negative ion ESI mass Ultrorac 7000). Chromatograms were recorded on a plot- spectra were obtained from a Bruker Apex III Fourier trans- ter (Servogor 200). The multilayer coil was prepared form ion cyclotron resonance (FT-ICR) mass spectrometer from 1.6 mm ID PTFE tubing. The total capacity was (Bruker Daltonics, Billerica, USA) equipped with an InWn- 300 mL. The MLCCC was run at a revolution speed of ity™ cell, a 7.0 Tesla superconducting magnet (Bruker, 800 rpm and a Xow rate of 2 mL min¡1 in head to tail Karlsruhe, Germany), an RF-only hexapole ion guide and modus. an external electrospray ion source (APOLLO; Agilent, oV Samples of 1 g were dissolved in a 1:1 mixture (10 mL) axis spray). Nitrogen was used as drying gas at 150 °C. The of light and heavy phase and injected into the system. Sol- samples were dissolved in methanol and the solutions were vent system A for separation of diethyl ether extract con- introduced continuously via a syringe pump at a Xow rate sisted of water/ethyl acetate (2:1 v/v). Ethyl acetate of 120 Lh¡1. The data were acquired with 256 k data extracts were separated by using ethyl acetate/n-butanol/ points and zero Wlled to 1,024 k by averaging 32 scans. water (2:1:4 v/v) (solvent system C). Then, structures of the residual stationary phase of both mentioned extracts Magnetic resonance spectroscopy (NMR) were isolated by chloroform/methanol/water (4:3:2 v/v) (solvent system B). n-Butanol extracts were separated by NMR spectra were recorded on a Varian Unity Inova 500 using ethyl acetate/n-butanol/water (3:1:4 v/v) (solvent instrument (Darmstadt, Germany). Chemical shifts are system D). given relative to external Me4Si. 123 Eur Food Res Technol Results and discussion Isolation and elucidation of phenolic ingredients from rhizome Diethyl ether, ethyl acetate and n-butanol extract from rhi- zome (Rhei radix) were screened for Xavonoids by analyti- cal HPLC-DAD. Basically, the ethyl acetate and n-butanol extracts revealed the same ingredients. Therefore, diethyl ether and ethyl acetate extract were used for isolation of substances. Final structural evidence was achieved by 1H- and 13C-nuclear magnetic resonance (NMR), as well as het- eronuclear multiple quantum coherence (HMQC) and het- eronuclear multiple bond correlation (HMBC) NMR experiments. Diethyl ether extract HPLC-DAD chromatogram of diethyl ether extract is shown in Fig. 1. First step of puriWcation was separation by MLCCC (system A) (Fig. 2a). Stationary phase retention was between 65–70%. The residual stationary phase was further processed by a second MLCCC-step (system B, retention: 80%) (Fig. 2b). Afterwards, fractions A–C were separated by preparative HPLC to isolate pure substances. The following structures were veriWed: trans-rhapontigenin 1 (C) ( max =318nm), cis-desoxyrhaponticin 2 (A) ( = 314 nm) and trans-desoxyrhapontigenin 3 (B) max Fig. 2 I 1 3 Separation of diethyl ether extract ( , solvent system A) and the ( max = 311 nm) (Figs. 2, 3). and have been isolated residual stationary phase (II, solvent system B) from rhubarb rhizome from rhubarb rhizome before (R. undulatum, R. oYcinale). by MLCCC. A, cis-desoxyrhaponticin 2; B, trans-desoxyrhapontigenin NMR-data of 1 was in line with Kashiwada et al. [15], 3; C, trans-rhapontigenin 1 NMR-data of 3 in good agreement with Choi et al. [16]. HR-MS gave a pseudo-molecular mass of m/z 257.1 for trans-rhapontigenin 1 [m/z 257.0821 (found); m/z 257.0819 ¡ calculated for C15H13O4 [M–H] ] and a pseudo-molecular mass of m/z 241.1 for trans-desoxyrhapontigenin 3 [m/z 241.0873 (found); m/z 241.0870 calculated for C15H13O3 [M–H]¡].
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