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N-Alkylresorcinol Occurrence in Mercurialis Perennis L. (Euphorbiaceae) Peter Lorenz, Matthias Knödler, Julia Bertrams, Melanie Berger, Ulrich Meyer, and Florian C

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N-Alkylresorcinol Occurrence in Mercurialis Perennis L. (Euphorbiaceae) Peter Lorenz, Matthias Knödler, Julia Bertrams, Melanie Berger, Ulrich Meyer, and Florian C n-Alkylresorcinol Occurrence in Mercurialis perennis L. (Euphorbiaceae) Peter Lorenz, Matthias Knödler, Julia Bertrams, Melanie Berger, Ulrich Meyer, and Florian C. Stintzing* WALA Heilmittel GmbH, Department of Research & Development, Dorfstraße 1, D-73087 Bad Boll/Eckwälden, Germany. E-mail: fl [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 65 c, 174 – 179 (2010); received November 9/December 10, 2009 Investigation of the dichloromethane extracts from herbal and root parts of Mercurialis perennis L. afforded a mixture of 11 homologous n-alkylresorcinols (ARs) with saturat- ed odd-numbered alkyl side chains (C15:0–C27:0). In addition to three predominant ARs (C19:0, C21:0 and C23:0), a number of minor ARs were identifi ed by use of LC-MS/MS and GC-MS techniques. Among the compounds detected, four uncommon ARs with even- numbered alkyl side chain lengths were also determined. The overall AR concentration in herbal parts was 7 to 9 times higher compared to that of the roots. The results presented may open a new view on the phytochemistry and pharmacognosy of M. perennis and other members of the Euphorbiaceae family. Key words: Mercurialis, Euphorbiaceae, Acalypheae, n-Alkylresorcinols Introduction (Lorenz et al., 2009). However, constituents from dog’s mercury are still poorly known. The herbal parts of dog’s mercury (Mercuria- In continuation of our studies on the spectrum lis perennis L., Euphorbiaceae, subfamily Aca- of bioactive metabolites from medicinal plants, lypheae) are used in remedies effective for topi- dichloromethane (DCM) extracts of the herbal cal treatment of infl ammation, poorly healing and root parts of M. perennis were investigated. wounds, sore or dry and infl amed eyes (Madaus, As a previous study on the lipid constituents of 1979). Applied orally the fresh herb or root are M. perennis (Lorenz et al., 2010) afforded a minor faintly poisonous and show a strong laxative and fraction that has not been characterized yet, the diurectic effect (Madaus, 1979; Blaschek et al., present work reports on the closer inspection of 2008). In the European ethnomedicine M. peren- this fraction. Most unexpectedly, a complex mix- ture of n-alkylresorcinols (ARs) was found. Us- nis is administered for the treatment of various ing LC-MS/MS and GC-MS techniques as well as affections such as eczema, dropsy, and tumours chemical derivatization methods these compounds (Blaschek et al., 2008). were identifi ed as a homologous series of side Previous phytochemical studies on M. perennis chain-saturated ARs (C15:0–C27:0, see Fig. 1). led to the identifi cation of piperidine alkaloids ARs are a subclass of phenolic lipids which till (Swan, 1984, 1985; Lorenz et al., 2009), fl avonoid now have been found in members from only a glycosides (Dumkow, 1969), simple phenolics, few plant families and display a multitude of bio- terpenes, triacylglycerols, tocopherols and sterols logical activities (Kozubek and Tyman, 1999). Materials and Methods HO (CH ) 2 n Extraction of the plant material Herbal and root parts of Mercurialis peren- OH nis were collected in the mountain forest close n = 1, 3 – 11, 13 to Bad Boll/Eckwälden (Baden-Württemberg, Fig. 1. Chemical structures of n-alkylresorcinols identi- Germany) in April 2009 and identifi ed by Prof. fi ed in M. perennis. Otto Spring, Department of Botany, Hohenheim 0939 – 5075/2010/0300 – 0174 $ 06.00 © 2010 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D P. Lorenz et al. · Alkylresorcinols from Mercurialis perennis 175 University, Stuttgart, Germany. Voucher speci- ear gradient was followed to 100% B at 60 min, mens (HOH-006229-HOH-006232) are deposited kept for 5 min before re-equilibrating to starting at this department. The fresh plant material was conditions. kept at – 80 ºC until investigation. Herbal parts of A purifi ed AR fraction (23 mg, obtained via M. perennis (100.4 g) yielded 0.7 g crude DCM a procedure described above) was dissolved in extract after repeated extraction (2 × 500 mL) methanol (10 mL). The resulting clear solution at room temperature under nitrogen atmos- was fi ltered through a 0.45-μm GHP Acrodisc® phere. The crude DCM extract (0.7 g dissolved membrane (PALL Life Sciences, Dreieich, Ger- in 30 mL DCM) was loaded on a polyamide col- many) before use. The injection volume of each umn (11 × 2 cm; particle size, 0.05 – 0.16 mm; Carl sample was 20 μL. The HPLC system was coupled Roth, Karlsruhe, Germany) preconditioned with to a HCT ultraion trap (Bruker Daltonik, Bremen, DCM (50 mL). Thereafter the column was washed Germany) fi tted with an APCI source operating in with DCM (150 mL, fraction discharged) fol- the positive mode with the following parameters: lowed by methanol (200 mL). The yielded metha- HV voltage, – 4000 V; dry gas, N2; fl ow rate, 5.0 L/ nol fraction (70.0 mg) was chromatographed via min; with a dry temperature set at 300 ºC; neb- vacuum liquid chromatography (VLC) on TLC ulizer, 2.72 atm; vaporizer temperature, 400 °C. grade silica gel (Merck) with a DCM/methanol Full scan mass spectra of the HPLC eluates were mixture (49:1 – 48:2) yielding two AR-enriched recorded during the chromatographic separation fractions (23.0 + 3.0 mg) which were unifi ed. For yielding [M+H]+ ions. To obtain further structural quantitative GC-MS analysis herbal or root parts information, these ions were trapped and frag- (22.0 – 25.0 g) were immersed in DCM (250 mL). mented to yield the precursor product patterns Subsequently, the plant material was minced by a of the analytes. The mass range was recorded Ultra-Turrax® (21,000 rpm; IKA-Werke, Staufen, from m/z 50 – 1000 with a compound stability and Germany). A stream of nitrogen was bubbled trap-drive level of 100%. MSn data were acquired through the extraction mixture for 5 min before in the auto-MS/MS mode. The instruments were and after Ultra-Turrax® treatment. The slurry was controlled by an Agilent Chemstation and an Es- allowed to stand for 24 h. Afterwards the sediment quireControl Software. was recovered by vacuum fi ltration over Celite and the fi lter cake re-extracted in the same man- Derivatization of the ARs for GC-MS analyses ner again and fi nally washed with DCM (50 mL). Remaining water was removed from the combined To gain further structural information, the fi ltrates by sodium sulfate and the DCM fraction ARs were silylated or methoxylated and the so- evaporated to dryness under vacuum rotovapo- obtained products were analyzed by GC-MS. The ration. For GC-MS measurements the residues silylation of the analytes was implemented by were dissolved in chloroform (20 mL) containing treatment of the AR fraction (26 mg) with 0.5 mL the internal reference compound eicosane. chloroform and 0.2 mL silylating mixture Fluka I by Sweeley (45 min at 105 ºC) according to a pre- HPLC-DAD-MS/MS analyses viously reported procedure (Lorenz et al., 2010). Chromatographic analyses were carried out with The methoxylation was performed by treatment an Agilent 1200 HPLC system (Agilent Technolo- of the AR fraction [5.0 mg, dissolved in 10 mL gies Inc., Palo Alto, USA), equipped with a binary methanol/water (9:1, v/v)] with a diazomethane/ pump, a microvacuum degasser, an autosampler, a diethyl ether solution. The latter was prepared thermostatic column compartment and a UV-VIS from N-nitrosomethyl urea (4.0 g in 48 mL di- diode array detector (DAD). The UV detection ethyl ether) and an ice-cold aqueous potassium of the ARs was performed at 275 nm. A Syner- hydroxide solution (40%, 10 mL) by a literature gy Hydro-RP column (4 μm, 2.0 × 150 mm i. d.; procedure (Beckert et al., 2009). After stirring Phenomenex, Torrance, CA, USA) was used for (3 h) at room temperature the reaction mixture chromatographic separation at 25 °C. The mobile was purged with a vigorous stream of nitrogen phase consisted of water (mobile phase A) and to remove unreacted diazomethane and diethyl methanol (mobile phase B) with a fl ow rate of ether. Before GC-MS analyses the residual prod- 0.30 mL/min. Starting with 83% B at 0 min, a lin- uct was dissolved in methanol (1 mL). 176 P. Lorenz et al. · Alkylresorcinols from Mercurialis perennis GC-MS analyses in the range 0.003 – 0.113 mg/mL (r2 = 0.997). The GC-MS was performed with a Perkin Elmer area percentages of the main ARs (C19:0, C21:0, and C23:0) were determined and calculated as Clarus 500 gas chromatograph with split injection C19:0 assuming equal peak sensitivities. AR con- (split ratio, 30:1; injection volume, 1.0 μL) coupled centrations were calculated on the dry matter ba- to a mass detector. The column used was a Ze- sis of the plant material. bron ZB-5 ms capillary column (60 m × 0.25 mm i. d. × 0.25 μm fi lm thickness, 5% phenylpolysi- Results and Discussion loxane and 95% dimethylpolysiloxane coating; Phenomenex). Helium was the carrier gas at a A purifi ed AR fraction (see Materials and fl ow rate of 1 mL/min. The injector used was a PSS Methods) was analyzed by HPLC/DAD, using an (programmed-temperature split/splitless injector; APCI source in the MS/MS-mode according to temperature, 250 ºC). The temperature program Knödler et al. (2007, 2009). The HPLC chromato- o for the column oven was 100 to 320 ºC at 4 C/ grams recorded at 275 nm showed several peaks min with a fi nal hold time of 30 min. The mass whose UV spectra concordantly exhibited two spectrometer was run in the electron ionization specifi c maxima at 276 and 280 nm, characteristic mode (70 eV).
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