Chemical characterization and bioactive properties of Geranium molle L . : from the plant to the most active extract and its phytochemicals

After a period of indifference, in which synthetic compounds were favored, there is an increasing interest in the study of the biological properties of plants and the active principles responsible for their therapeutic properties. Geranium molle L. has been used in the Portuguese folk medicine for the treatment of various ailments including cancer but, unlike many of the species from the Geranium genus, its phytochemical characterization and biological activity are virtually unexplored. In this study a G. molle sample from Trásos-Montes, north-eastern Portugal, was chemically characterized regarding nutritional value, free sugars, organic acids, fatty acids and tocopherols, and several aqueous (decoction, infusion) and organic (n-hexane, dichloromethane, ethyl acetate, acetone, methanol) extracts of the plant were assessed for their bioactive properties. The antioxidant activity was evaluated by means of the free radicals scavenging activity, reducing power and inhibition of lipid peroxidation. The cytotoxicity of the different extracts was assessed in vitro against several human cancer cell lines (breast, lung, cervical and hepatocellular carcinomas) and, additionally, their hepatotoxicity was evaluated using a porcine liver primary cell culture. G. molle was shown to be rich in carbohydrates and proteins, providing tocopherols and essential fatty acids. Amongst the various extracts, the acetone extract was found to have the highest content of phenolic compounds (mainly ellagitannins, but also some flavone and flavonol glycosides) as well as the highest antioxidant and cytotoxic activities. To the best of our knowledge, this is the first report on the chemical composition and bioactive properties of G. molle.


Introduction
The use of medicinal plants to improve health was highly valued in ancient civilizations.Until the mid-nineteenth century, plants were the main therapeutic agents used by humans. 1,2After a period of indifference, in which synthetic compounds were favored, in recent years increasing interest of researchers has been observed in the study of the biological activity of plants and the active principles responsible for their therapeutic properties. 3,4he most studied classes of compounds being tannins, flavonoids and phenolic acids.The phenolic compounds, especially the flavonoids, have been cited as the main biologically active components among those found in Geranium species. 11This class of compounds from Geranium spp.][13] Although the Geranium genus phytochemistry is relatively well-known, reports on the chemical composition and biological properties of Geranium molle L. cannot be found in the literature.Therefore, in the present study, a wild sample of Geranium molle L. was analysed for its nutritional composition ( proteins, fat, carbohydrates and ash) and chemically characterized regarding hydrophilic (sugars, organic acids) and lipophilic (fatty acids and tocopherols) molecules.An infusion and a decoction (common forms of consumption) and different organic extracts were evaluated for their bioactive properties, namely the antioxidant and antitumor properties, being the most active extract characterized in terms of phenolic compounds.

Plant material
Geranium molle L. specimens in blossom (including thin roots, basal leaves, ascending stems, upper hairy leaves and flowers) were collected in Serra da Nogueira, Bragança, north-eastern Portugal, in March 2015, and subsequently, all dirt and dried parts were cleaned out.The amount of plant material collected was around 780 g.Voucher specimens are deposited at the herbarium of the Escola Superior Agrária de Bragança (BRESA).The botanical identification was confirmed by the agronomist Dra.Ana Maria Carvalho of the School of Agriculture, Polytechnic Institute of Bragança (Trás-os-Montes, Portugal).The sample was lyophilized, reduced to a fine dried powder (∼20 mesh), mixed to obtain a homogeneous sample and stored in a refrigerator at −20 °C, protected from light.
2.3.Chemical characterization 2.3.1.Macronutrient composition of the crude plant material.The sample was analysed for its nutritional chemical composition ( proteins, fat, carbohydrates and ash) through standard procedures. 14The crude protein content (N × 6.25) of the sample was estimated by the macro-Kjeldahl method.The crude fat was determined by extracting a known weight of powdered sample with petroleum ether, using a Soxhlet apparatus.The ash content was determined by incineration at 600 ± 15 °C.Total carbohydrates were calculated by difference.Energy was calculated according to the following equation: energy (kcal) = 4 × (g protein + g carbohydrate) + 9 × (g fat).

Hydrophilic compounds
Free sugars.Free sugars were determined via high performance liquid chromatography coupled to a refraction index detector (HPLC-RI), after an extraction procedure previously described by the authors 15 using melezitose as internal standard (IS).The equipment consisted of an integrated system with a pump (Knauer, Smartline system 1000, Berlin, Germany), a degasser system (Smart line manager 5000) and an auto-sampler (AS-2057 Jasco, Easton, MD, USA) coupled to a refraction index (RI) detector (Knauer Smartline 2300).The chromatographic separation was achieved with a Eurospher 100-5 NH 2 column (5 µm, 4.6 × 250 mm, Knauer) operating at 30 °C (7971 R Grace oven).The mobile phase was acetonitrile/ deionized water, 70 : 30 (v/v), at a flow rate of 1 mL min −1 .Sugar identification was performed by comparing the relative retention times of sample peaks with standards.Data were analyzed using Clarity 2.4 Software (DataApex, Podohradska, Czech Republic).Quantification was based on the RI signal response of each standard, using the IS (melezitose) method and by using the calibration curves obtained for the commercial standards of each compound.The results were expressed in g per 100 g of dry weight.
Organic acids.Organic acids were determined following a procedure previously optimized and described by the authors. 16The analysis was performed using a Shimadzu 20A series ultra-fast liquid chromatograph (UFLC) (Shimadzu Corporation, Kyoto, Japan).Separation was achieved on a SphereClone (Phenomenex, Torrance, CA, USA) reverse phase C 18 column (5 μm, 4.6 × 250 mm) thermostatted at 35 °C.The elution was performed with 3.6 mM sulphuric acid using a flow rate of 0.8 mL min −1 .Detection was carried out with a diode array detector (DAD), using 215 nm and 245 nm (for ascorbic acid) as the preferred wavelengths.The organic acids found were quantified by comparison of the area of their peaks, recorded at 215 or 245 nm, with the calibration curves obtained for commercial standards of each compound.The results were expressed in g per 100 g of dry weight.

Lipophilic compounds
Fatty acids.Fatty acids were determined after transesterification according to the procedure previously described by the authors. 15The fatty acid profile was analyzed with a DANI 1000 gas chromatograph (GC) equipped with a split/splitless injector, a flame ionization detector (FID) and a Macherey-Nagel (Düren, Germany) column (50% cyanopropyl-methyl-50% phenylmethylpolysiloxane, 30 m × 0.32 mm i.d.× 0.25 µm d f ).The oven temperature program was as follows: the initial temperature of the column was 50 °C, held for 2 min, then a 30 °C per min ramp to 125 °C, 5 °C per min ramp to 160 °C, 20 °C per min ramp to 180 °C, 3 °C per min ramp to 200 °C, 20 °C per min ramp to 220 °C and held for 15 min.The carrier gas (hydrogen) flow-rate was 4.0 mL min −1 (0.61 bar), measured at 50 °C.Split injection (1 : 40) was carried out at 250 °C.Fatty acid identification was performed by comparing the relative retention times of the sample's FAME peaks with standards.The results were recorded and processed using Clarity 4.0.1.7Software (DataApex, Podohradska, Czech Republic) and expressed as a relative percentage of each fatty acid.
Tocopherols.Tocopherols were determined following a procedure previously described by the authors. 15The analysis was performed by HPLC (equipment described in Section 2.3.2,sub section Free sugars), using a fluorescence detector (FP-2020; Jasco, Easton, MD, USA) programmed for excitation at 290 nm and emission at 330 nm.The chromatographic separation was achieved with a Polyamide II (YMC Waters, Milford, MA, USA) normal-phase column (5 μm, 4.6 mm × 250 mm), operating at 35 °C.The mobile phase used was a mixture of n-hexane and ethyl acetate (70 : 30, v/v) at a flow rate of 1 mL min −1 .The compounds were identified by chromatographic comparison with authentic standards.Quantification was based on the fluorescence signal response of each standard, using the IS (tocol) method, and the calibration curves obtained for commercial standards of each compound.The results were expressed in mg per 100 g of dry weight.

Preparation of organic and aqueous extracts
The organic (hexane, dichloromethane, ethyl acetate, acetone and methanol) and aqueous (obtained by infusion and decoction) extracts were prepared from the lyophilized plant.
For the preparation of the organic extracts a sample (100 g) was extracted with 500 mL of n-hexane and the mixture was stirred vigorously at room temperature, 150 rpm, for 48 h, and then filtered under reduced pressure successively through a Whatman No. 541 paper and a sintered glass funnel.The solid residue was extracted with an additional 500 mL of n-hexane under the same conditions.The combined extracts were evaporated to dryness at 40 °C under reduced pressure.The resulting residue was further extracted sequentially with dichloromethane, ethyl acetate, acetone and finally methanol, according to the procedure described above.
The infusions were prepared by adding the sample (1 g) to 100 mL of boiling distilled water, left to stand at room temperature for 5 min, and then filtered under reduced pressure successively through a Whatman No. 541 paper and a sintered glass funnel.The obtained infusions were frozen and lyophilized.
The decoctions were also prepared by adding the sample (1 g) to 100 mL of distilled water and boiled for 5 min.The mixture was left to stand for 5 min at room temperature and then filtered under reduced pressure successively through a Whatman No. 541 paper and a sintered glass funnel.The obtained decoctions were frozen and lyophilized.

Bioactive compounds in the extracts
For total phenolics determination, an aliquot of the different extracts (1 mL, 78-625 μg mL −1 ) were mixed separately, with Folin-Ciocalteu reagent (5 mL, previously diluted with water 1 : 10 v/v) and sodium carbonate (75 g L −1 , 4 mL).The tubes were vortexed for 15 s and allowed to stand for 30 min at 40 °C for color development.Absorbance was then measured at 765 nm. 17Gallic acid was used to calculate the standard curve (0.1-1 mM) and the results were expressed as mg of gallic acid equivalents (GAE) per g of extract.
For total flavonoids determination, an aliquot of the different extracts (0.5 mL, 313-625 μg mL −1 ) were mixed separately, with distilled water (2 mL) and subsequently with NaNO 2 solution (5%, 0.15 mL).After 6 min, AlCl 3 solution (10%, 0.15 mL) was added and allowed to stand further 6 min, thereafter, NaOH solution (4%, 2 mL) was added to the mixture.Immediately, distilled water was added to bring the final volume to 5 mL.Then the mixture was mixed properly and allowed to stand for 15 min.The intensity of the pink color was measured at 510 nm. 18Catechin was used to calculate the standard curve (0.3-1 mM) and the results were expressed as mg of catechin equivalents (CE) per g of extract.
2.6.Evaluation of bioactive properties of the extracts 2.6.1.Antioxidant activity assays.The organic extracts were redissolved in methanol (final concentration 10 mg mL −1 ).The aqueous extracts were redissolved in water (final concentration 10 mg mL −1 ).The final solutions obtained were further diluted to different concentrations to be subjected to distinct evaluation assays of the antioxidant activity.
DPPH radical-scavenging activity was evaluated by using an ELX800 microplate reader (Bio-Tek Instruments, Inc.; Winooski, VT, USA), and calculated as a percentage of DPPH discoloration using the formula: [(A DPPH − A S )/A DPPH ] × 100, where A S and A DPPH are, respectively, the absorbance of the sample solution and that of the DPPH solution at 515 nm.Reducing power was evaluated by the capacity to convert Fe 3+ into Fe 2+ , measuring the absorbance at 690 nm in the microplate reader mentioned above.Inhibition of β-carotene bleaching was evaluated through the β-carotene/linoleate assay; the neutralization of linoleate free radicals avoids β-carotene bleaching, which is measured by the formula: (β-carotene absorbance after 2 h of assay/initial absorbance) × 100.Lipid peroxidation inhibition in porcine (Sus scrofa) brain homogenates was evaluated by the decrease in thiobarbituric acid reactive substances (TBARS); the color intensity of the malondialdehyde-thiobarbituric acid (MDA-TBA) was measured by its absorbance at 532 nm; the inhibition ratio (%) was calculated using the following formula: [(A − B)/A] × 100%, where A and B are the absorbance of the control and the sample solution, respectively. 16,19he results were expressed in EC 50 values (sample concentration providing 50% of antioxidant activity or 0.5 of absorbance in the reducing power assay).Trolox was used as positive control.
2.6.2.Cytotoxicity in human tumor cell lines.The aqueous and organic extracts were redissolved in water and ethanol 20%, respectively, in order to obtain a final concentration of 8 mg mL −1 .The final solution was further diluted to different concentrations (400 to 1.5 µg mL −1 ) to be subjected to in vitro cytotoxicity evaluation.Four human tumor cell lines were used: MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), HeLa (cervical carcinoma) and HepG2 (hepatocellular carcinoma).The cells were routinely maintained as adherent cell cultures in RPMI-1640 medium containing 10% heat-inactivated FBS (MCF-7 and NCI-H460) and 2 mM glutamine or in DMEM supplemented with 10% FBS, 2 mM glutamine, 100 U per mL penicillin and 100 mg per mL streptomycin (HeLa and HepG2 cells), at 37 °C, in a humidified air incubator containing 5% CO 2 .Each cell line was plated at an appropriate density (7.5 × 10 3 cells per well for MCF-7 and NCI-H460 or 1.0 × 10 4 cells per well for HeLa and HepG2) in 96-well plates and allowed to attach for 24 h.The cells were then treated for 48 h with the different diluted sample solutions.Following this incubation period, the adherent cells were fixed by adding cold 10% TCA (100 μL) and incubated for 60 min at 4 °C.Plates were then washed with deionized water and dried; SRB solution (0.1% in 1% acetic acid, 100 μL) was then added to each plate-well and incubated for 30 min at room temperature.Unbound SRB was removed by washing with 1% acetic acid.Plates were air-dried, the bound SRB was solubilised with 10 mM Tris (200 μL, pH 7.4) and the absorbance was measured at 540 nm in the microplate reader mentioned above. 16The results were expressed in GI 50 values (sample concentration that inhibited 50% of the net cell growth).Ellipticine was used as positive control.
2.6.3.Hepatotoxicity in non-tumor cells.A cell culture was prepared from a freshly harvested porcine liver obtained from a local slaughter house, and it was designed as PLP2.Briefly, the liver tissues were rinsed in Hank's balanced salt solution containing 100 U per mL penicillin, 100 µg per mL streptomycin and divided into 1 × 1 mm 3 explants.Some of these explants were placed in 25 cm 2 tissue flasks in DMEM medium supplemented with 10% fetal bovine serum, 2 mM nonessential amino acids and 100 U per mL penicillin, 100 mg per mL streptomycin and incubated at 37 °C under a humidified atmosphere containing 5% CO 2 .The medium was changed every two days.Cultivation of the cells was continued with direct monitoring every two to three days using a phase contrast microscope.Before confluence was reached, cells were subcultured and plated in 96-well plates at a density of 1.0 × 10 4 cells per well, and cultivated in DMEM medium with 10% FBS, 100 U per mL penicillin and 100 µg per mL streptomycin. 15,16Cells were treated for 48 h with the different diluted sample solutions and the same procedure described in the previous section for the SRB assay was followed.The results were expressed in GI 50 values (sample concentration that inhibited 50% of the net cell growth).Ellipticine was used as positive control.

Phenolic composition of the acetone extract
The acetone extract was redissolved in water/methanol 80 : 20 (v/v) (final concentration 5 mg mL −1 ).Phenolic compounds were determined by HPLC (Hewlett-Packard 1100 chromatographer, Agilent Technologies, Santa Clara, CA, USA) as previously described by the authors. 16,19Double online detection was carried out with a DAD using 280 nm and 370 nm as preferred wavelengths and with a mass spectrometer (MS) connected to the HPLC system via the DAD cell outlet.The phenolic compounds were identified by comparing their retention time, UVvis and mass spectra with those obtained from standard compounds, when available.Otherwise, peaks were tentatively identified comparing the obtained information with the available data reported in the literature.For quantitative analysis, a calibration curve for each available phenolic standard was constructed based on the UV signal.For the identified phenolic compounds for which a commercial standard was not available, the quantification was performed through the calibration curve of other compound from the same phenolic group.The results were expressed in mg per g of extract.

Statistical analysis
For all the experiments, three samples were analyzed and all the assays were carried out in triplicate.The results are expressed as mean values ± standard deviation (SD).The differences between the different samples were analyzed using oneway analysis of variance (ANOVA) followed by Tukey's honestly significant difference post hoc test with α = 0.05, coupled with Welch's statistic.This treatment was carried out using the SPSS v. 22.0 program.

Chemical characterization of Geranium molle L.
The results of the nutritional characterization of G. molle, namely, macronutrients, sugars, organic acids and fatty acids, are presented in Table 1.Carbohydrates were the most abundant macronutrients found in the studied sample, followed by proteins, fat and ash.This plant showed 72.2% of moisture and the energetic contribution was ∼436 kcal per 100 g dw.
Fructose, glucose and sucrose were the free sugars detected in this sample.The total sugar content was ∼9 g per 100 g dw, glucose being present in a much larger amount (∼6 g per 100 g dw) than the two other sugars.
A total of six different organic acids were detected in the plant, namely, oxalic, quinic, malic, ascorbic, citric and fumaric acids (Table 1).Malic acid was the most abundant (∼2.8 g per 100 g dw), followed by quinic acid (∼2.6 g per 100 g dw).
Regarding tocopherols, α-tocopherol (18.9 mg per 100 g dw) was the most abundant isoform present in G. molle.β-Tocopherol and γ-tocopherol were present but in very small amounts.δ-Tocopherol was not detected in this plant.

Bioactive compounds in different Geranium molle L. extracts
Concentrations of total polyphenols and total flavonoids, as determined by photometrical methods in different G. molle extracts are presented in Table 2.The acetone extract displayed the highest content of both total polyphenols (497 mg GAE per g extract) and total flavonoids (112 mg CE per g extract).Acetone has been reported as a good solvent for the extraction of phenolic compounds and flavonoids. 20,21The infusion and the decoction presented similar concentrations of total flavo-noids but somewhat different content of total polyphenols, the extract resulting from the infusion being richer in this group of compounds.The dichloromethane and the n-hexane extracts showed very low concentrations of both total polyphenols and total flavonoids.

Bioactive properties of different Geranium molle L. extracts
The in vitro antioxidant and cytotoxic properties of different extracts of G. molle were evaluated, and the results are presented in Table 3.The antioxidant activity was determined by free radical (DPPH) scavenging activity, reducing power, inhibition of lipid peroxidation in brain cell homogenates, and TBARS assays.The cytotoxicity was tested against human tumor cell lines (breast, lung, cervical and hepatocellular carcinomas) and the hepatotoxicity was evaluated using a porcine liver primary cell culture.
In general, all the extracts revealed antioxidant potential.The acetone extract displayed the highest antioxidant activity in all the assays.This was probably related to the higher content of total phenols and total flavonoids found in this extract, compared to the other prepared extracts (Table 2).The  antioxidant properties of many plants are closely related to the presence of phenolic compounds, which constitute the most abundant secondary metabolites of plants. 22egarding the cytotoxic properties, almost all of the extracts showed activity.The aqueous extract obtained by infusion, and methanol and ethyl acetate extracts showed similar cytotoxic effects against MCF-7, NCI-H460 and HeLa cells.The dichloromethane extract was ineffective against the HepG2 cell line even at the maximum concentration assayed (400 µg mL −1 ).The n-hexane extract showed activity only against HeLa cells.The acetone extract displayed the highest cytotoxic effect, being significantly more potent than the remaining extracts (GI 50 values approximately four times lower) against all cell lines.Unfortunately, this extract also presented the highest toxicity against normal primary cells from the porcine liver (PLP2) (GI 50 ∼ 190 μg mL −1 ).However, the concentration required to reach 50% of growth inhibition of PLP2 is about 3-4 times higher than the concentration required to achieve 50% of growth inhibition of the human tumor cell lines tested.Therefore, a dosage of 85 µg mL −1 of the G. molle acetone extract would be recommended to guarantee 50% of growth inhibition of the human tumor cell lines tested, without presenting toxicity effects for non-tumor cells.
The aqueous, dichloromethane and n-hexane extracts did not show hepatotoxicity against PLP2 cells up to the maximal tested concentration (GI 50 > 400 μg mL −1 ).The methanol and ethyl acetate extracts presented similar hepatotoxicity against this cell line (GI 50 ∼ 330 μg mL −1 ).
Trolox and ellipticine were used as positive controls in the antioxidant and cytotoxic activity assays, respectively.However, as these are individual compounds, they should not be considered as standards and comparison with the results obtained for the extracts/oral preparations should be avoided since an eventual synergistic effect of the mixtures cannot be precluded.

Analysis of phenolic compounds in the acetone extract
Amongst the several G. molle extracts prepared, the acetone extract was found to exhibit the highest amount of total phenolic compounds, as well as the highest antioxidant and cytotoxic activity, so that its detailed phenolic composition was also analysed.The HPLC phenolic profile of that extract recorded at 280 and 370 nm is shown in Fig. 1.The peak characteristics and tentative identities are presented in Table 4. Sixteen phenolic compounds were detected, five of which were ellagitannins, one phenolic acid and ten flavonoids.The antioxidant activity was expressed as EC 50 values, which means that higher values correspond to lower reducing power or antioxidant potential.EC 50 : extract concentration corresponding to 50% of antioxidant activity or 0.5 of absorbance in reducing power assay.Trolox EC 50 values: 41 µg mL −1 (reducing power), 42 µg mL −1 (DPPH scavenging activity), 18 µg mL −1 (β-carotene bleaching inhibition) and 23 µg mL −1 (TBARS inhibition).GI 50 values correspond to the sample concentration achieving 50% of growth inhibition in human tumour cell lines or in liver primary culture PLP2.Ellipticine GI 50 values: 1.21 µg mL −1 (MCF-7), 1.03 µg mL −1 (NCI-H460), 0.91 µg mL −1 (HeLa), 1.10 µg mL −1 (HepG2) and 2.29 µg mL −1 (PLP2).In each row different letters mean significant differences (p < 0.05).
The remaining compounds would correspond to flavonoids.447) were associated to quercetin glycosides based on their absorption spectra and the production of an ion fragment at m/z 301.Their molecular weights pointed to a quercetin-Opentoside ( peak 15) and a quercetin derivative bearing two deoxyhexosyl and one hexosyl residues ( peak 8).In the latter derivative, the fact that only one MS 2 fragment was released corresponding to the aglycone suggests that the three sugars constituted a trisaccharide.Flavonol derivatives have been previously described in other Geranium sp.][36][37][38][39][40] Finally compound 11 ([M − H] − at m/z 563) was tentatively assigned as apigenin 2″-O-pentosyl-6-C-hexoside according to its pseudomolecular ion and fragmentation pattern.A compound with the same characteristics had been previously found by our group in Arenaria montana 41 and identified based on the fragmentation patterns described by Ferreres et al. 42 and Ferreres et al. 43 for O,C-glycosyl flavones.As far as we know this type of compound is reported herein for the first time in Geranium species, although some flavone O-glycosides and aglycones, i.e., luteolin and apigenin, have been reported in Geranium sp.][40] Digalloyl-HHDP-glucoside (compound 5) was the most abundant ellagitannin present, while luteolin-6-C-glucoside (compound 9) was the best represented flavonoid.Chlorogenic acid (i.e., 5-O-caffeoylquinic acid) was the only hydroxycinnamoyl derivative found in the analysed sample.

Conclusions
Geranium molle L. is rich in carbohydrates and proteins, providing tocopherols and essential fatty acids.In general, the various aqueous and organic extracts showed antioxidant activity and cytotoxicity against the different human tumour cell lines tested.The acetone extract presented the highest antioxidant potential in the different assays, which is most probably related to its higher content of polyphenols and flavonoids compared with the other prepared extracts.The acetone extract also displayed the highest cytotoxic effect, being significantly more potent than the remaining extracts against all cell lines (GI 50 values approximately four times lower).Although this extract also presented the highest toxicity against porcine liver primary cells (PLP2), the GI 50 value for PLP2 was about 3-4 times higher than those for the tumor cell lines tested.The decoction and the infusion of the plant, which are the common forms of folk consumption, did not show hepatotoxicity against PLP2 cells up to the maximal tested concentration (400 µg mL −1 ), but presented GI 50 for the tumor cells 3-4 times higher than the acetone extract.The phenolic profile of the acetone extract was determined by HPLC-MS and shown to be constituted mainly by ellagitannins, as well as some flavone and flavonol glycosides.All in all, the obtained results support the folk medicinal use of G. molle, and its interest as a source of phytochemicals with bioactive properties to be explored in the medicine and food industries.

Table 4
Retention time (R t ), wavelengths of maximum absorption in the visible region (λ max ), mass spectral data, identification and quantification of phenolic compounds of the acetone extract of Geranium molle L.

Table 1
Chemical characterization of Geranium molle L. in terms of macronutrients, and hydrophilic and lipophilic compounds

Table 2
Bioactive compounds in different Geranium molle L. extracts