{"id":44087,"date":"2022-06-30T11:28:34","date_gmt":"2022-06-30T11:28:34","guid":{"rendered":"https:\/\/biomedpharmajournal.org\/?p=44087"},"modified":"2022-07-19T07:59:22","modified_gmt":"2022-07-19T07:59:22","slug":"antioxidant-activity-and-flavonoid-estimation-in-rosa-multiflora-and-rosa-wichuraiana-fruits-and-flowers","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol15no2\/antioxidant-activity-and-flavonoid-estimation-in-rosa-multiflora-and-rosa-wichuraiana-fruits-and-flowers\/","title":{"rendered":"Antioxidant Activity and Flavonoid Estimation in Rosa multiflora and Rosa wichuraiana Fruits and Flowers"},"content":{"rendered":"

Introduction<\/strong><\/p>\n

Species belonging to the genus Rosa<\/em> (Rosaceae) are widely distributed in temperate and subtropical regions of the northern hemisphere. Numerous Rosa<\/em> species are used for medical purposes or ornamentals. In Korea, the fruits of Rosa multiflora<\/em> called Yeongsil are used to treat dropsy, edema, constipation, nocturnal enuresis and the species\u2019 flowers are used to treat malaria and bleeding1-4<\/sup>. Rosa multiflora<\/em> is a perennial shrub with thorny stems and has alternate compound leaves, generally with five to eleven sharply toothed leaflets, and tolerance for a broad range of soil, moisture and light conditions. The principal components of the species\u2019 fruit include quercetin glycosides, kaempferol glycosides, methyl gallate, and lycopene which is red pigment of fruits5-7<\/sup> and several studies have reported that Rosa multiflora<\/em> exhibits antimicrobial, antioxidant, melanogenesis-inhibiting, and anti-inflammatory activities8,9<\/sup>. Meanwhile, the closely related species Rosa wichuraiana<\/em> is native to Japan, Korea, east China and Taiwan, where it grows best in lowland thickets, near ocean. The species can be differentiated from R. multiflora<\/em> by its thicker and more lustrous leaves. Interestingly, the somatic hybridization and propagation of R. wichuraiana <\/em>has been studied to use the species as a novel source of disease resistance in ornamental rose breeding10-12<\/sup>. However, the bioactivity of the species has yet to be investigated.<\/p>\n

The production of free radicals in the human body can induce oxidative stress, which can damage DNA, proteins, and lipids, ultimately causing various chronic illnesses (e.g., \u00a0cancer and cardiovascular disease)13-15<\/sup>. \u00a0However, even though antioxidants can be used to reduce the incidence of reactive oxygen species (ROS; e.g., superoxide anion radicals, hydroxyl radicals, non-freeradical species, and single oxygen)16,17<\/sup>, the use of synthetic antioxidants has been associated with negative side effects18<\/sup>. Thus, the bioactive constituents and antioxidant activities of natural sources have received increasing interest.<\/p>\n

Flavonoids, like kaempferol and quercetin, are plant secondary metabolites with polyphenolic structure and various biological activities19<\/sup>. Furthermore, kaempferol and quercetin have been identified in multiple plant species used in traditional medicine20<\/sup>. The most important characteristic of flavonoid compounds is their antioxidative activity, and many studies have reported linear relationships between flavonoid content and antioxidant activity21-23<\/sup>. This is the first study to compare the antioxidant activities and flavonoid contents of R. <\/em>multiflora <\/em>and R. wichuraiana<\/em>.<\/p>\n

Materials and Methods<\/strong><\/p>\n

Chemicals and solvents used for this study were purchased from Sigma Chemicals (St Louis, MO, USA) and Difco (Detroit, MI, USA).<\/p>\n

Rosa <\/em>multiflora <\/em>fruits and flowers were collected from Suncheon, Korea (34\u00b054\u02b927\u02b9\u02b9N, 127\u00b034\u02b952\u02b9\u02b9E), in September 2015 and May 2016, and R. <\/em>wichuraiana <\/em>fruits and flowers were collected from Goheung, Korea (34\u00b043\u02b965\u02b9\u02b9N, 127\u00b049\u02b947\u02b9\u02b9E), in September 2015 and June 2016. The plant was authenticated by one of the authors (K. W. Yun), and voucher specimens (SCNU 2015 201 and SCNU 2016 53, respectively) were also collected and were deposited in the herbarium of Sunchon National University. The collected flowers and fruits were air-dried for 14 d.<\/p>\n

The air-dried fruit and flower of the two Rosa species was ground into powder. The samples (100 g) were soaked in 1,000 mL of ethanol and kept at room temperature for 24 hr and then filtered through filter paper (Whatman No.2). The crude ethanol extract was fractionized with 500 mL of hexane and then the top layer was concentrated (comprising the hexane fraction). The remaining layer was successively fractionized with 500 mL of diethyl ether and then ethyl acetate (forming the ether and ethyl acetate fraction). The remaining residue was the water fraction. Finally, each fraction was concentrated (in vacuo<\/em>, 30 \u00b0C ) to 30 mL for the subsequent measurement of antioxidant activity and flavonoid contents.<\/p>\n

The 1,1-diphenyl-2-picrylhydrazyl (DPPH)of each fraction was measured using a modified version of the method described by Blois24<\/sup>. Briefly, 140 \u00b5L DPPH (0.075 mM, in methanol) was added to fraction aliquots to reach final concentrations of 3.13\u2013100.00 \u00b5g\/mL, gently mixed, and incubated in the dark at 25 \u00b0C for 30 min. Butylhydroxy toluene (BHT; 100 \u00b5g\/mL) and After incubation, the optical density at 517 nm (OD517<\/sub>) of each reaction mixture was measured using an ELISA Reader (Color techno system Co., Tokyo, Japan), and DPPH free radical scavenging activity was calculated as follows:<\/p>\n

Scavenging activity (%) = (1 \u2013 [absorbance of sample] \/ [absorbance of control]) \u00d7 100%.<\/p>\n

The superoxide anion radical scavenging activity of each fraction was measured according to Fridovich25<\/sup>. Superoxide radicals were generated in 0.4 mL potassium phosphate buffer (0.1M, pH 7.5) that contained 1 mL xanthine (0.4 mM), 1 mL nitro blue tetrazolium chloride (NBT, 0.24 mM) solution, 1 mL xanthine oxidase (0.2 unit\/mL) and 0.1 mL Rosa <\/em>extract fraction. The reaction mixtures were incubated at 37 \u00b0C for 20 min. After incubation, the optical density at 560 nm (OD560<\/sub>) of each reaction mixture was measured using an ELISA Reader. Lower the absorbance value, higher the superoxide radical scavenging activity was observed. The IC50<\/sub> value was inversely correlated with antioxidant activity of the tested fractions; lower IC50<\/sub> value indicated higher antioxidant activity 26<\/sup><\/p>\n

For quantitative estimation of kaempferol and quercetin, each of the four extract fractions of two Rosa<\/em> species\u2019 fruits and flowers was lyophilized using lyophilizer (Ilsin Co, Korea), and the lyophilized powders were stored in airtight bottles at \u22125\u00b0C until used. Kaempferol and quercetin standards (30 \u00b5g\/mL) were prepared using methanol. High- performance liquid chromatographic (HPLC) was performed using Aglient 1200 series system (Agilent Technologies Inc., Santa Clara, CA, USA) that was equipped with a ZORBAX SB-C18<\/sub> column (4.6 mm \u00d7 150 mm, 3.5 \u00b5m; Agilent). Ultra-distilled water and acetonitrile were used as mobile phases A and B, respectively. The flow rate and injection volume were 1.0 mL\/min and the 5 \u00b5L, respectively, and the elution profile was as follows: 15% B for 0\u20131.5 min; 17% B for 3\u20134 min; 20-35% B for 7\u201314 min. The elution was monitored in the UV range, and the data for quantitative analysis were acquired at 360 nm. The retention time of quercetin and kaempferol was 7.63 min and 10.98 min, respectively. The kaempferol and quercetin contents were quantified using the external standard calibration method27<\/sup>.<\/p>\n

Data were expressed as mean \u00b1 standard deviation values (n = 3). Statistical analysis was performed using SPSS software (version 24.0; SPSS Inc., Chicago, IL, USA). The significance of differences between means was evaluated using Duncan\u2019s test.<\/p>\n

Results and Discussion<\/strong>\u00a0<\/em><\/p>\n

Table 1 shows the yield of the four fractions of ethanol extract from R. multiflora<\/em> and R. wichuraiana<\/em>. Solvents of increasing polarity were used to fractionate the crude ethanol extracts. The determination of stable DPPH radicals scavenging is a widely used and common method for the relatively rapid evaluation of antioxidant activity28,29<\/sup>. The DPPH free radical scavenging activity of the two Rosa<\/em> species is shown in Table 2. The DPPH radical scavenging activities of hexane and water fraction of R. multiflora<\/em> fruit extract are 82.93% and 79.10% at 50 \u00b5g\/mL DPPH, whereas that of ether fraction is 69.57% at 12.5 \u00b5g\/mL DPPH. The DPPH radical scavenging activity of the ethyl acetate fraction of R. multiflora<\/em> fruit was greater than that of BHT. The DPPH radical scavenging activities of the hexane, ether, ethyl acetate, and \u00a0water fraction of the R. multiflora<\/em> flower were 70.07%, 79.27%, 82.54%, and 95.28%, respectively, at DPPH concentration of 100 \u00b5g\/mL. The activities of hexane, ether, ethyl acetate, and water fractions of R. wichuraiana <\/em>flower were 37.15%, 47.42%, 83.04%, and 77.58%, respectively, at DPPH concentration of 100 \u00b5g\/mL. The DPPH radical scavenging activity of the ether fraction of the R. wichuraiana<\/em> flower was 69.70% at a DPPH concentration of 50 \u00b5g\/mL, and the DPPH radical scavenging activities of ethyl acetate and water fractions of the R. wichuraiana<\/em> flower were greater than that of BHT, regardless of DPPH concentration. Park et al.4<\/sup> reported that the DPPH radical scavenging activities of ethanol, methanol, and acetone extracts of R. multiflora<\/em> roots were 80% at a DPPH concentration of 100 \u00b5g\/mL and that the scavenging activity of an aqueous extract was 40% at a DPPH concentration of 50 \u00b5g\/mL. The DPPH radical scavenging activities of aqueous and ethanol extracts of Potentilla supina<\/em> (Rosaceae) were 25.2% and 35.97%, respectively, at 25 \u00b5g\/mL DPPH, whereas those of methanol extracts of three Rosa<\/em> species were 64.5%, 51.8%, and 43.6%, respectively, at 100 \u00b5g\/mL DPPH30-32<\/sup>. In the present study, the ethyl acetate and water fractions exhibited greater DPPH free radical scavenging activities than the other two fractions, and the R. multiflora<\/em> extract fractions exhibited greater DPPH free radical scavenging activity than the R. wichuraiana <\/em>extract fractions.<\/em><\/p>\n

Table 1:\u00a0Yield of each fraction from Rosa multiflora<\/em> and R. wichuraiana.<\/em><\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
Plant<\/strong><\/td>\nPlant organ<\/strong><\/td>\nExtract fraction<\/strong><\/td>\nYield (%)<\/strong><\/td>\n<\/tr>\n
Rosa multiflora<\/em><\/td>\nFruit<\/td>\nHexane<\/td>\n0.63\u00b10.12 d<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n1.24\u00b10.22 c<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n2.35\u00b10.26 b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n6.43\u00b10.31 a<\/sup><\/td>\n<\/tr>\n
Flower<\/td>\nHexane<\/td>\n0.94\u00b10.26 d<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n1.87\u00b10.32 c<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n3.91\u00b10.34 b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n10.18\u00b10.69 a<\/sup><\/td>\n<\/tr>\n
Rosa wichuraiana<\/em><\/td>\nFruit<\/td>\nHexane<\/td>\n0.4\u00b10.04 cd<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n0.7\u00b10.07 c<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n1.46\u00b10.18 b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n4.78\u00b10.52 a<\/sup><\/td>\n<\/tr>\n
Flower<\/td>\nHexane<\/td>\n0.78\u00b10.13 d<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n1.71\u00b10.17 c<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n4.01\u00b10.39 b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n9.08\u00b10.72 a<\/sup><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

a <\/sup>Values with different letters in the same column were significantly (p<\/em> < 0.05) different.<\/p>\n

Duncan\u2019s test should be compared within each part of a plant.<\/p>\n\n\n\n
\"Vol15No2_Ant_Hye_tab2\"<\/a><\/td>\nTable 2: DPPH free radical scavenging activity of solvent fractions from two Rosa <\/em>species.<\/strong><\/p>\n

Click here to view table<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n

Superoxides are radicals that contain an oxygen atom with unpaired electrons. \u00a0Despite having low chemical reactivity, superoxides can generate highly reactive species, such as hydroxyl radicals and the protonated form of superoxide. The superoxide anion radical scavenging activity of the two Rosa<\/em> species are shown in Table3. In the present study, IC50 <\/sub>was calculated as the concentration that caused a 50% reduction in the superoxide anion radical concentration. The superoxide anion radical scavenging activities of ether fraction from R. multiflora<\/em> and R. <\/em>wichuraiana<\/em> flower were 0.06 and 0.09 mg\/mL, respectively, whereas those of the ethyl acetate fractions of the R. multiflora<\/em> and R. <\/em>wichuraiana<\/em> fruit extracts were 0.14 and 0.08 mg\/mL.. The superoxide anion radical scavenging activities of the ethyl acetate fractions of the fruit extracts and the ether fractions of flower extracts were greater than those of the other fractions, regardless of species. The superoxide anion radical scavenging activity of ethyl acetate fraction of Sanguisorba officinalis<\/em> (Rosaceae) extract was 40% at a concentration of 1,000 \u00b5g\/mL, and the scavenging activity of water extract of Prunus sargentii<\/em> was 40 % at a concentration of 500 ppm33,34<\/sup>. Superoxide radicals are powerful oxidizing agents that can react with biological membranes and induce tissue damage. Moreover, these radicals decompose to singlet oxygen, hydroxyl radical, or hydrogen peroxide molecules and may be \u00a0associated with the onset of a various pathological conditions, including rheumatoid arthritis and cancer35,36<\/sup>.<\/p>\n

Table 3:\u00a0The superoxide anion radical scavenging activity of solvent fractions from two Rosa<\/em> species.<\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
Plant<\/td>\nPlant organ<\/td>\nExtract fraction<\/td>\nIC50<\/sub> (\u00b1SD, mg\/ml)a<\/sup><\/td>\n<\/tr>\n
Rosa multiflora<\/em><\/td>\nFruit<\/td>\nHexane<\/td>\n0.31\u00b10.05a<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n0.24\u00b10.02b<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n0.14\u00b10.04b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n0.34\u00b10.02a<\/sup><\/td>\n<\/tr>\n
Flower<\/td>\nHexane<\/td>\n0.36\u00b10.01a<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n0.06\u00b10.00c<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n0.20\u00b10.00b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n–<\/td>\n<\/tr>\n
Rosa wichuraiana<\/em><\/td>\nFruit<\/td>\nHexane<\/td>\n0.24\u00b10.01b<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n0.18\u00b10.00c<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n0.08\u00b10.00d<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n0.70\u00b10.00a<\/sup><\/td>\n<\/tr>\n
Flower<\/td>\nHexane<\/td>\n0.16\u00b10.01b<\/sup><\/td>\n<\/tr>\n
Ether<\/td>\n0.09\u00b10.01b<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n0.69\u00b10.04a<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n0.14\u00b10.02b<\/sup><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

a <\/sup>Values with different letters in the same column were significantly (p<\/em> < 0.05) different.<\/p>\n

Duncan\u2019s test should be compared within each part of a plant.<\/p>\n

Kaempferol and quercetin are present in many plant species that are commonly used in traditional medicine20<\/sup>. The compounds have been associated with reduced risk of pancreatic cancer, and quercetin, in particular, is effective against prostate cancer37<\/sup>. Kaempferol is a\u00a0 markedly active inhibitor of COX-2 transcriptional activation and exhibits antimicrobial activity against Propionibacterium acnes<\/em>38,39<\/sup>. One of the goals of the present study was to measure the kaempferol and quercetin contents of fractions of two Rosa<\/em> species fruit and flower extracts (Table 4; Fig. 1; Fig.2). Unlike the observed for extraction yield, the flavonoids content did not show dependence on the yield. The content of kaemferol was 10.35 mg% and 6.21 mg% in ethyl acetate fraction of R. multiflora <\/em>and R. wichuraiana <\/em>flower, these are the highest contents of kaempferol. Among the fruit fractions of the two Rosa<\/em> species, quercetin was detected only in the ether fraction of R. multiflora<\/em>. The water and ethyl acetate fractions of the R. multiflora <\/em>and R. wichuraiana <\/em>flower extracts contained more quercetin than the other two fractions, and no quercetin was detected in fractions of the R. <\/em>wichuraiana<\/em> fruit extract. The ether fractions of both the R. multiflora <\/em>and R. wichuraiana <\/em>fruit extracts contained more quercetin than the other fractions, and more quercetin was detected in the ethyl acetate fractions of the two Rosa <\/em>species flower extracts. In contrast to the previous studies21-23,40<\/sup>, the findings of the present study did not show strong correlation between flavonoid contents and antioxidant activity. Previous studies41,42<\/sup> have reported that the kaempferol and quercetin contents of Rubus idaeus <\/em>(Rosaceae) and Prunus cerasus<\/em> leaves are 2.38 and 5.05 mg\/kg, respectively. Liaudanskas et al.43<\/sup> reported a strong correlation between total phenolic contents and radical scavenging and reducing activities of the Rosa<\/em> fruits grown in Lithuania, and another study44<\/sup> reported that the ethyl acetate fraction of Rosa multiflora <\/em>flower extract had greater phenolic content and antioxidant activity than other tested fractions.<\/p>\n

Table 4:\u00a0The contents of kaempferol and quercetin in solvent fractions from two Rosa <\/em>species.<\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
Plant<\/strong><\/td>\nPlant organ<\/strong><\/td>\nExtract fraction<\/strong><\/td>\nKaempferol<\/strong><\/p>\n

(\u00b1SD, mg%)a<\/sup><\/strong><\/td>\n

Quercetin<\/strong><\/p>\n

(\u00b1SD, mg%)a<\/sup><\/strong><\/td>\n<\/tr>\n

Rosa multiflora<\/em><\/td>\nFruit<\/td>\nHexane<\/td>\n–<\/td>\n–<\/td>\n<\/tr>\n
Ether<\/td>\n0.47\u00b10.03a<\/sup><\/td>\n5.78\u00b10.79a<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n–<\/td>\n0.93\u00b10.14b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n–<\/td>\n0.20\u00b10.14b<\/sup><\/td>\n<\/tr>\n
Flower<\/td>\nHexane<\/td>\n–<\/td>\n–<\/td>\n<\/tr>\n
Ether<\/td>\n1.50\u00b10.41b<\/sup><\/td>\n1.53\u00b10.61b<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n10.35\u00b10.77ab<\/sup><\/td>\n4.53\u00b10.54bc<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n12.13\u00b10.89a<\/sup><\/td>\n9.16\u00b10.82a<\/sup><\/td>\n<\/tr>\n
Rosa wichuraiana<\/em><\/td>\nFruit<\/td>\nHexane<\/td>\n–<\/td>\n–<\/td>\n<\/tr>\n
Ether<\/td>\n–<\/td>\n2.73\u00b10.00a<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n–<\/td>\n0.72\u00b10.35b<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n–<\/td>\n0.82\u00b10.44b<\/sup><\/td>\n<\/tr>\n
Flower<\/td>\nHexane<\/td>\n–<\/td>\n–<\/td>\n<\/tr>\n
Ether<\/td>\n1.73\u00b10.52b<\/sup><\/td>\n2.01\u00b10.69b<\/sup><\/td>\n<\/tr>\n
Ethyl acetate<\/td>\n6.21\u00b10.61a<\/sup><\/td>\n11.69\u00b11.01a<\/sup><\/td>\n<\/tr>\n
Water<\/td>\n1.18\u00b10.46b<\/sup><\/td>\n2.26\u00b10.99b<\/sup><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

a <\/sup>Values with different letters in the same column were significantly (p<\/em> < 0.05) different<\/p>\n\n\n\n
\"Vol15No2_Ant_Hye_fig1\"<\/a><\/td>\nFigure 1:\u00a0 The structure of kaempferol and quercetin.<\/strong><\/p>\n

Click here to view figure<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n\n
\"Vol15No2_Ant_Hye_fig2\"<\/a><\/td>\nFigure 2: The chromatogram of kaempferol and quercetin standard by HPLC\u00a0<\/strong>(A, Quercetin; B, Kaempferol).<\/strong><\/p>\n

Click here to view figure<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n

Conclusion<\/strong>\u00a0<\/strong><\/p>\n

The antioxidant activity and flavonoid contents of various fractions (hexane, ether, ethyl acetate, and water) of ethanol extract from R. multiflora<\/em> and R. wichuraiana <\/em>used complementary in Korea were evaluated. The greater antioxidant activity by DPPH assay exhibited in the ethyl acetate or water fraction of two Rosa<\/em> species extracts, whereas greater superoxide anion radical scavenging activity was shown in the ether or ethyl acetate fraction. The content of flavonoid, such as kaempferol and quercetin in the four fractions is not reflected clearly in the DPPH and superoxide anion radical scavenging activity. However, the findings of the study still suggest that the two Rosa<\/em> species could be useful as natural antioxidants or food additives.<\/p>\n

Acknowledgment<\/strong><\/p>\n

This work was supported by a Research promotion program of SCNU.<\/p>\n

Conflict of Interest<\/strong><\/p>\n

The authors declare that there are no conflicts of interest.<\/p>\n

Funding Sources<\/strong><\/p>\n

There is no funding source.<\/p>\n

References<\/strong><\/p>\n

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