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Chemical and Pharmacological Investigations of Metaxya Rostrata

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Chemical and Pharmacological Investigations of Metaxya Rostrata Chemical and Pharmacological Investigations of Metaxya rostrata Judith Virtbauera, Liselotte Krenna,*, Hanspeter Kähligb, Antje Hüfnerc, Oliver Donatha, and Brigitte Mariand a Department of Pharmacognosy, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria. Fax: (+431) 427755259. E-mail: [email protected] b Institute of Organic Chemistry, University of Vienna, Vienna, Austria c Institute of Pharmaceutical Sciences, University of Graz, Graz, Austria d Department of Medicine 1, Institute of Cancer Research, Medical University Vienna, Vienna, Austria * Author for correspondence and reprint requests Z. Naturforsch. 63c, 469Ð475 (2008); received February 11/March 12, 2008 In a bioassay-guided approach the chemical composition of rhizomes of Metaxya rostrata (Kunth C. Presl) was studied for the first time. Investigations of the cytotoxicity of extracts and fractions on SW480 colorectal carcinoma cells resulted in the isolation of two polyphe- nols Ð cinnamtannin B-1 and aesculitannin B. The structures of the compounds were eluci- dated by different NMR experiments. Additionally, sugars, common sterols, such as sitosterol, stigmasterol and campesterol, as well as chlorogenic acid and caffeic acid were identified in Metaxya rostrata. Key words: Metaxya rostrata, Polyphenols, Cytotoxic Effects Introduction ity, the capacity to alter the cell cycle, and the in- duction of apoptosis in SW480 colorectal carci- Metaxya rostrata is a tree fern widespread in noma cells by extracts from the rhizome of lowland rain forests of Central America and the Metaxya rostrata seemed of interest. north-western parts of South America. Within the Metaxyaceae family only two species Ð Metaxya Materials and Methods rostrata (Kunth C. Presl) and Metaxya lanosa A. R. Sm. & H. Tuomisto Ð have been described General until now (Smith et al., 2001). The chemical com- ESI-mass spectra were recorded on a PE Sciex position of both species has not been investi- API 150 EX single quadrupole instrument (Ap- gated before. plied Biosystems, Foster City, CA, USA) configu- From physicians and traditional healers in the rated for negative ionization. Full scan spectra region of Corcovado Parque National in Costa were acquired over the range m/z 150Ð2000; scan Rica informations were obtained that suspensions time was 2 s. NMR spectra were recorded on a of the dried rhizome of Metaxya rostrata in water Bruker Avance DRX 600 NMR spectrometer us- are administered orally in Costa Rican ethnic ing eithera5mmtriple resonance probe (TBI, 1H, medicine in intestinal diseases such as ulcers or 13C, broad band) with triple axis gradients for all tumours. As colorectal carcinomas are among the 1H-detected experiments, or a 5 mm switchable most common cancers causing a large part of can- quadruple probe (QNP, 1H, 13C, 19F, 31P) with z- cer deaths in western industrialized countries and axis gradients and automatic tuning and matching are characterized by high inherent resistance and accessory for direct detected carbon experiments. low response to therapy (Ragnhammar et al., The resonance frequency for 1H NMR was 600.13 2001), the development of new therapeutics for MHz, for 13C NMR 150.92 MHz. All measure- colorectal cancer is an important ongoing task ments were performed for a solution in fully deu- (Kinghorn et al., 2003; Cragg and Newman, 2005). terated methanol at 300 K. Standard 1D and gradi- Tropical plants used in ethnomedicine provide a ent-enhanced (ge) 2D experiments, like double rich source for new cytotoxic compounds (Kim quantum filtered (DQF) COSY, TOCSY, NOESY, and Park, 2002). Thus, a bioassay-guided chemical ROESY, HSQC, and HMBC, were used as sup- investigation based on the antiproliferative activ- plied by the manufacturer. The setup for the diffu- 0939Ð5075/2008/0700Ð0469 $ 06.00 ” 2008 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D 470 J. Virtbauer et al. · Functional Investigations on Metaxya rostrata sion difference experiments was chosen as pub- H2O mixtures of increasing polarity as mobile lished (Kählig et al., 2002). phases. 15 subfractions were obtained. The most TLC was performed on silica gel plates (Merck, active fraction 11 was subjected to column chro- Germany; 0.25 mm); mobile phases for the identi- matography on Sephadex“ LH-20 by gradient elu- fication of phenolic acids: (A) EtOAc/HOAc/ tion with MeOH/H2O mixtures (70% to 100% HCO2H/H2O (100:11:11:26 v/v/v/v); (B) EtOAc/ MeOH). Of 16 subfractions collected fraction butanone/HCOOH/H2O (50:30:10:10); detec- Sx11 (220 mg) was submitted to another separa- tion: Naturstoffreagens A/PEG 400 under UV366 tion step under similar conditions, and from the (Wagner and Bladt, 1996); mobile phases for the resulting fractions Sy3 (25 mg) and Sy4 (81 mg) identification of sugars: (C) n-propanol/acetone/ compound Rx (15 mg) was crystallized. lactic acid (40:40:20); (D) n-butanol/acetic acid/ Extract C (2.6 g) was extracted with hexane re- diethyl ether/H2O (9:6:1:1); naphthoresorcinol/ sulting in 1.46 g hexane fraction and 0.84 g chloro- phosphoric acid (Merck, 1970). form residue. By threefold VLC on silica using methanol/chloroform and hexane/ethylacetate Plant material and extraction mixtures as mobile phases, sitosterol (9 mg), stig- Rhizomes of Metaxya rostrata were collected in masterol (3 mg) and campesterol (1.3 mg) were the surroundings of La Gamba, Costa Rica, in isolated (Rigler, 2005; Metnitzer, 2007). February 2003 (Guaymi Reservation, Cerro Rin- con, La Gamba) and authenticated in the Herba- Determination of cytostatic and cytotoxic activity rium of the Museo National in San Jose. The roots SW480 carcinoma cells obtained from the were sundried for 2 h and exported with permis- American Type Culture Collection and cultivated sion from Ministerio de Ambiente y Energia (Mi- under standard conditions [minimal essential me- nAE) and INBio of Costa Rica. Voucher speci- dium (MEM) containing 10% fetal calf serum mens are deposited in the Herbarium of the (FCS)] were used to assess the cytotoxic capacity Department of Pharmacognosy (University of Vi- of bioactive fractions as described by Hausott et al. enna, Vienna, Austria). (2004). In short, cells were exposed to increasing 800 g dried roots were pulverized, and portions concentrations of bioactive compounds diluted in of 100 g were extracted by sonification with 1 l MEM containing 1 mg/ml bovine serum albumin water at 50 ∞C for 1 h, each. Each extraction was 48 h after plating. repeated 5 times. After lyophilization the yield of Another 48 h later cell viability was determined the combined water (W) extract was 90 g. Com- by neutral red uptake. The presence of apoptotic pounds of medium polarity were extracted under structures in the culture was detected by staining the same conditions with methanol to yield 20 g of with Hoechst 33258 (800 ng/ml) to visualize the MeOH (M) extract. The apolar components were morpholgy of nuclei. Apoptosis was indicated by extracted from 100 g portions of the drug with condensation or fragmentation of chromatin. The 650 ml of chloroform (C), each. These extractions incidence of such structures was counted from were repeated twice and resulted in 2.88 g of ex- 1000 cells each in triplicate cultures. tract C. Unspecific cytotoxicity and cell lysis were deter- mined with the Cytotoxicity Detection Kit from Fractionation Roche Diagnostics (Vienna, Austria), which quan- 80 g of extract W were extracted sequentially tifies the release of lactat dehydrogenase (LDH) with ethylacetate, butanol and methanol to yield into the culture medium. 0.75 g of fraction WE, 26.35 g of fraction WB and Cell cycle analysis was performed on nuclei iso- 18.7 g of fraction WM as well as 33 g residue WW lated from cultures treated with plant extracts after evaporation. 15 g of extract M were parti- (0.5 mg/ml serum-free medium) and fractions at tioned between ethylacetate and water as well as different concentrations as described before (Hau- between butanol and water. The solvents were sott et al., 2004) evaporated or lyophilized to yield fractions ME After identification of apoptotic structures by (4 g), MB (9 g) and MW (1.5 g). The cytotoxic staining with Hoechst 33258 mitochondrial polari- fractions WE, WB, WM, ME and MB were sub- zation was assessed by incubation of the harvested jected to vacuum liquid chromatography (VLC) cells with the mitochondrial tracking dye JC1 fol- on silica (15Ð40 μm, Merck) using EtOAc/MeOH/ lowed by FACS analysis (Hausott et al., 2004). J. Virtbauer et al. · Functional Investigations on Metaxya rostrata 471 Results and Discussion Preliminary phytochemical analyses of the rhi- zome of Metaxya rostrata showed the presence of sterols, phenolic compounds and saccharides. Ad- ditionally the independence of the composition of secondary metabolites of environmental factors was verified by chromatographic comparison of samples from three different collection sites, at Cerro Rincon, La Gamba and in Guaymi Reserva- tion. The initial extraction of the material copied, as far as possible, the preparation for the use in ther- apy, which is one promising strategy in medicinal plant research (Hostettmann et al., 1998). Thus, Fig. 1. Cytotoxicity of frs. 1, 2, 4Ð11 determined by neu- the material was extracted by sonification with hot tral red uptake from serum-free DMEM. Cultures were water. For the isolation of less polar compounds exposed to the fractions obtained by vaccum liquid chro- additional extraction with methanol and chloro- matography diluted in serum-free medium, and viability was determined 48 h later by neutral red uptake. form followed. Fig. 2. Growth effects of fr. 11. (a, b) Cells were exposed to 70 μg/ml of fr. 11 in serum-free medium for 48 h before viability was determined by neutral red uptake to show a loss of viability of about 50% as compared to control. After removal of the neutral red solution cultures were washed with PBS and stained with Hoechst 33258 to visualize the nuclei.
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