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��ࡱ�>��	]_����Z[\�����������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������[�	���bjbj����;ΐΐW�,�������������   8X�4� �B0��n�������?�?�?�?�?�?�?$�D�vGB�?�������?���^B�=�=�=�,���?�=��?�=�=�=��������X�c� �8H�={?tB0�B�=�G:��G�=�=�G�=��"��=�������?�?�<0����B�������������������������������������������������������������������������G�����������:The influence of ripening stage and extraction method on polyphenol composition and antioxidant activity of cumin (Cuminum cyminum L.) seeds

Iness Bettaieb Rebey, Sarra Kefi, Iness Jabri-Karoui, Kamel Msaada, Ferid Limam and Brahim Marzouk
Laboratoire des Substances Bioactives Centre de Biotechnologie � la Technopole de Borj-C�dria (CBBC), BP 901, Hammam-Lif, Tunisia.






*Corresponding author:
Iness Bettaieb Rebey, Tel: +21697547029; Fax: +21679412638 
E-mail addresses: HYPERLINK "mailto:rosainess@yahoo.fr"rosainess@yahoo.fr, HYPERLINK "mailto:bettaiebrebey@yahoo.fr"bettaiebrebey@yahoo.fr




















Abstract
The e�ects of two extraction methods, used at three ripening stage on the total polyphenol contents and the antioxidant activities of Cumin (Cuminum cyminum L.) seed extracts were studied. The harvesting time effect on some physical properties of cumin seed was signi�cant. The increase of dry weight (from 10.3 to 87.5 %) during ripeness was correlated negatively with that of moisture content (from 89.7 to 12.5%). Besides results showed that the mature stage was richer on polyphenols and condensed tannin than immature stage, and consequently exhibited higher antioxidant activities. However, the immature stage had a higher total �avonoid content compared to those of intermediate and mature ones.
The comparison of two extraction methods showed that soxhlet extracts contained the greatest amount of polyphenols and flavonoids, while maceration ones exhibited higher antiradical and bleaching power assay. Total phenolic contents and IC values in cumin seed during their maturation, allowed to conclude that antioxidant activity does not depend on the high content of total phenolics but on the phenolic composition. A total of 19 phenolic compounds were successfully identified by HPLC analysis, during the ripening of cumin seeds. Rosmarinic acid was the major phenolic acid for the immature stage. Furthermore, intermediate and mature stages were dominated by p-coumaric acid. Almost all of the identi�ed compounds were described in the literature as interesting bioactive natural substances that may be used in several �elds, such as nutraceuticals, cosmetics and agro-food industry. 
Keywords
Cuminum cyminum L., seeds, polyphenols, antioxidant, ripening, extraction method



Introduction
Spices are a potent source of antioxidants, some of them being more efficient and safer than the synthetic antioxidants. According to Pietta [1], the antioxidant effect of plant products could be mainly ascribed to phenolic compounds, such as flavonoids, phenolic acids, tannins, and phenolic diterpenes. Phenolics play an important role in human health owing to their anti-inflammatory, antiallergic, antimicrobial, anticarcinogenic, and antiviral activities [2]. In plants, these compounds prevent lipid peroxidation and oxidative modification of low density lipoproteins due to their antioxidant activities [3].
Cumin (Cuminum cyminum L.), is one of the most popular spices belonging to the Apiaceae family, widely distributed in temperate climate regions where they are often used as spices, vegetables or drugs owing to the presence of useful metabolites [4]. It is cultivated in Arabia, India, China and in the countries bordering the Mediterranean Sea [5]. Cumin seeds are used as a spice for their distinctive aroma, popular in Indian, Pakistan, North African, Middle Eastern, Sri Lankan, Cuban, Northern Mexican cuisines, and the Western Chinese cuisines of Sichuan and Xinjiang [6]. Cuminum cyminum seeds have been used for treatment of toothache, dyspepsia, diarrhoea, epilepsy and jaundice [7]. In our previous study, we reported that phenolic contents and antioxidant activity of cumin seed appeared to be accession and solvent dependent and that the extraction with 80% acetone led to the highest yield of these metabolites [8]. In addition, previous studies have shown that plant phenolic contents and their antioxidant activities depend on biological factors (genotype, organ and ontogeny), as well as environmental (temperature, salinity, water stress and light intensity) conditions [8, 9]. Post-harvesting procedures (storage) and extraction conditions (temperature, solvent polarity, extraction method, pH) deeply affect the antioxidant properties of these phyto-antioxidants [9, 10, 11, 12, 8]. However, literature about the most effective methods to extract these compounds is abundant but to some extent contradictory [13]. Considering the structure of these compounds and their physicochemical properties, it would be impossible to propose a universal extraction protocol. Many previous works reported the importance of the extraction procedures and their circumstances on the amount and the quality of the extracted antioxidants [14, 15]. 
Unlike fruits of other species, changes in phenolic composition and antioxidant activity with respect to maturity of Cuminum cyminum L. seed have not yet been undertaken. Hence, this study was undertaken to investigate changes in phenolic components and antioxidant activity at different stages of seed ripening in order to determine the optimal accumulation period of desirable compounds. Finally in order to utilize such source of phenolics, to evaluate it as an ethnic product, and to develop more complete compositional databases, a complementary chemical characterization was performed using RP-HPLC method.
Material and Methods 
Plant material
Cumin seeds were collected from cultivated plants in the region of Menzel Temim (Northwestern Tunisia) during June and July 2010. For collection at the initial stage (5 days after flowering: DAF) of maturity, only full green fruits were harvested. For the second stage, green-brown fruits were picked up. In the third stage, the majority of fruits were brown and a small of them were green-brown. Only brown fruits were chosen at the final stage of maturity.
Preparation of plant extracts
Plant material was dried in the dark for 3 days at room temperature and then reduced to a fine powder. The extraction of phenolic compounds from C. Cyminum seeds was carried out by two different methods.
Maceration
Maceration extracts were obtained by mixing 2.5 g of dry matter powder with 25 ml of 80% aqueous acetone (v/v). Maceration was performed at room temperature in a plug container with frequent agitation for 30 min. The extract was then kept for 24 h at 4 �C, filtered through a Whatman N �4 filter paper, and evaporated under vacuum to dryness. The extract was then stored in the darkness at 4 �C until analysis.
Soxhlet extraction
For the Soxhlet extracts, dry seeds (20 g) were packed into a paper thimble, inserted into a Soxhlet apparatus (type Gerhardt) and subjected to an exhaustive extraction with 200 ml of 80% aqueous acetone (v/v) at 85 �C for 6 h. The totality of the extract was retrieved, filtered through a Whatman N �4 filter paper, and evaporated under vacuum to dryness. The extract was then stored in the darkness at 4 �C until analysis.
Total phenolic content determination
The total phenolic amount of the acetone extracts was determined by using Folin�Ciocalteu reagent (Merck), according to the procedure described by Dewanto [16]. Briefly, 125 �l of sample extract were dissolved in 500 �l of distilled water and 125 �l of Folin�Ciocalteu reagent. The mixture was shaken, before addition of 1.25 mL of 7% Na2CO3, adjusting with distilled water to a final volume of 3 mL, and mixed thoroughly. After incubation in the dark for 90 min, the absorbance at 760 nm was measured versus the prepared blank. Total phenolic amounts were expressed as mg of gallic acid equivalents per gram of dry weight (mg GAE/g DW), through a calibration curve with gallic acid. All samples were analysed in triplicate.
Total flavonoid content
Total flavonoid contents were measured according to Dewanto [16]. An aliquot of diluted sample or standard solution of (+)-catechin was added to a 75 �L of NaNO2 solution, and mixed for 6 min, before adding 0.15 mL AlCl3 (100 g/L). After 5 min, 0.5 mL of NaOH was added. The final volume was adjusted to 2.5 mL with distilled water and thoroughly mixed. Absorbance of the mixture was determined at 510 nm against the same mixture, without the sample, as a blank. Total flavonoid content was expressed as mg catechin/g dry weight (mg CE/g DW), through the calibration curve of (+)-catechin. The calibration curve range was 50 400 �g/mL (R2 = 0.99). All samples were analyzed in three replications.
Assessment of total condensed tannins
Total tannin contents were measured using the modified vanillin assay described by Sun et al. [17]. To 50 �L of properly diluted sample, 3 ml of methanol vanillin solution (4%) and 1.5 mL of H2SO4 were added. The absorption was measured at 500 nm against extract solvent as a blank. The amount of total condensed tannins is expressed as mg (+)-catechin/g DW. The calibration curve range was 50 400 �g/mL (R2 = 0.99). All samples were analyzed in three replications.
Identification of phenolic compound using RP-HPLC
Dried samples of cumin seeds were hydrolysed according to the method of Proestos et al. [18] and slightly modified. 20 ml of acetone 80% containing BHT (1g/l) were added to 0.5g of a dried sample. Then, 10 ml of 1 M HCl were added. The mixture was stirred carefully and sonicated for 15 min and refluxed in a water bath at 90�C for 2 h. The obtained mixture was injected to HPLC. The phenolic compound analysis was carried out using an Agilent Technologies 1100 series liquid chromatography (RP HPLC) coupled with an UV-Vis multiwavelength detector. The separation was carried out on a 250 mm�4.6-mm, 4-�m Hypersil ODS C18 reversed phase column at ambient temperature. The mobile phase consisted of acetonitrile (solvent A) and water with 0.2% sulphuric acid (solvent B). The flow rate was kept at 0.5 mL/min. The gradient programme was as follows: 15% A/ 85% B 0-12 min, 40% A/ 60% B 12-14 min, 60% A/ 40% B 14�18 min, 80% A/ 20% B 18�20 min, 90% A/10% B 20�24 min, 100% A 24�28 min. The injection volume was 20 �l, and peaks were monitored at 280 nm. Samples were filtered through a 0.45 �m membrane filter before injection. Peaks were identified by congruent retention times compared with those of pure standards. Analyses were performed in triplicate.
DPPH radical scavenging assay
Radical-scavenging activity was determined according to Hanato et al. [19] Two millilitres of the extract at different concentrations were added to 0.5 ml of a 0.2 mM DPPH methanolic solution. After shaking, the mixture was incubated at room temperature in the dark for 30 min, and then the absorbance was measured at 517 nm. BHA was used as positive reference while methanol was used as negative reference. DPPH radical-scavenging activity was expressed as the inhibition percentage (I %) and was calculated using the following formula:
I% = 100 x (Ablank - Asample)/Ablank
where Ablank is the absorbance of the control at 30 min reaction (containing all reagents except the test compound), and Asample is the absorbance of the sample at 30 min. Antiradical activity was expressed as IC50, defined as the concentration of the extract generating 50% inhibition.
�-Carotene/linoleic acid bleaching assay
Antioxidant activity was evaluated according to the �-carotene bleaching method described by Tepe et al. [20] with slight modification. A stock solution of �-carotene/linoleic acid mixture was prepared by dissolving 0.5 mg of �-carotene in 1 ml of chloroform and adding 40 mg of linoleic acid together with 400 mg of Tween 40. Chloroform was completely evaporated using a vacuum evaporator. Then 100 ml of oxygenated distilled water were added to the residue; 3 ml of this mixture were dispensed to test tubes and 200 �l of each extract were added. The emulsion system was incubated for 2 h at 50 �C, together with two controls, one containing BHT as a positive control and another with the same volume of distilled water instead of the extracts. In the test tube with BHT, the yellow colour is maintained during the incubation period, and the absorbance was measured at 470 nm.
Statistical analysis
All extractions and determinations were conducted in triplicates. Data are expressed as mean � S.D. The means were compared by using the one-way and multivariate analysis of variance (ANOVA) followed by Duncan�s multiple range tests. The differences between individual means were deemed to be significant at p < 0.05. All analyses were performed by using the �Statistica v 5.1� [21] software.
Results and discussion
Physical characteristics of cumin seed
The cumin seed colour was adopted as a visual ripening criterion. In fact, the seeds turn from green (5 days after ripening, DAR) to green-brown (20 DAR) and �nally to brown (49 DAR) when completely ripe.
On the other hand, the effect of harvesting time on seed dry weight was signi�cant (p < 0.05) as shown in Table 1. The seed weight at 5 DAR (10.3 %) was the lowest because of seed immaturity. Seeds increased progressively in weight as growth progressed to obtain a maximum of 87.5 % at ripe seed (49 DAR). These results were similar to those of Hamrouni et al. [22] and Mhamdi et al. [23] who signaled that there is a strong positive correlation between maturity stage and seed dry matter due to the accumulation of organic matter in the ripe seeds.
Effect of the ripening stage and extraction method on phenolic contents
It is believed that major components of antioxidant activity in edible plants are polyphenolic compounds. Thus, it is necessary to extract polyphenolic compounds effectively when antioxidant activities are measured. In our previous study, we noted that extraction with 80% acetone led the highest polyphenol, flavonoid and tannin contents for cumin seeds [8]. The total polyphenols content (TPC) of cumin (Cuminum cyminum L.) seeds harvested at three ripening stages (immature, intermediate, and mature) and extracted with maceration and soxhlet methods is presented in Table 2.
Polyphenol content varied significantly mainly as function of ripening stage and extraction method. Considering the ripening stage, polyphenol content, in the extracts obtained by the two extraction methods was lower at immature stage as compared to mature one. For example, acetonic extract at immature stage (6.91 and 12.18 mg GAE/g DW) was much lower than at mature one (17.74 and 25.15 mg GAE/g DW), respectively to maceration and Soxhlet methods (Table 2). Accordingly, Bettaieb Rebey et al. [8], reported that the amount of TPC extracted by maceration from Tunisian cumin seed was 18.60 mg GAE /g DW). Whereas, El Ghorab et al. [24] reported that TPC evaluated in cumin methanolic extract was 35.5 mg GAE /g DW. In another study, Shan et al. [25] found a TPC of 2.3 mg GAE/g DW for 80% methanolic extracts of cumin. Such differences with our study could be ascribed to the effect of several factors including origin, climatic conditions and practical conditions as the chosen cultivar and organ [26]. In fact, and independently of the used extraction method, the level of these secondary metabolites exhibited an increase between immature and mature stage. Soxhlet extract of the mature stage showed the highest total phenolic content (25.15 mg GAE /g DW). The increase of total phenolic content observed at the last stage of seed ripening coincided with of the temperature increase in June. Similarly, Toor et al. [28] showed that high temperature had a positive effect on the accumulation of major antioxidant components of tomato. So, the accumulation of phenolic compounds was considered as a protective mechanism of plant against environmental conditions. In this context, previous study reported the periodicity in the production of phenolic compounds in phenol-rich species, with maxima in spring or summer because of its high temperatures, longer photoperiod, the increase of sunstroke intensity and lack in rainfall leading [29]. The extraction method must allow complete extraction of the compounds of interest, and it must avoid their chemical modi�cation [30]. Thus, the comparison of the two extraction methods revealed that total phenolic contents of soxhlet extracts of C. cyminum was higher than those of maceration extracts. Our results are in agreement with those of Hayouni et al. [14] and Hemwimon et al. [15]. This may be explained by the fact that an elevated extraction temperature, as used in the Soxhlet system, may cause thermal decomposition of substances [10], releasing phenolics from associated non-phenolic substances, thus allowing accurate phenolic contents. 
In addition, results displayed that extraction method as well as ripening stage, signi�cantly in�uenced �avonoid content (Table 2). However, extracts with higher phenolic content did not always have higher �avonoid content, as was evident for the maceration and Soxhlet extracts from the immature stage which had a higher total �avonoid content compared with those of intermediate and mature stages (Table 2). With similar tendency to phenolics, �avonoid content was remarkably higher in Soxhlet extracts than in maceration ones. Differences reach 2.5-folds within mature stage.
Furthermore, cumin is known to contain significant amount of tannins [31, 8]. Our findings confirm this since values of condensed tannin contents ranged from 33.50 to 68.72 mg CE/g DW for soxhlet and maceration method, respectively. As found for phenolics and flavonoids, tannins were found to vary depending on the ripening stage. For the two extraction methods, the highest condensed tannin contents were recorded at mature stage (68.72 and 33.50 EC/g DW), followed by intermediate (43.65 and 18.77 EC/g DW in the average) and immature stage (19.33 and 7.14 EC/g DW). Conversely to flavonoids and phenolics, tannin content was significantly higher in maceration extracts than in Soxhlet ones. 
Effect of the ripening stage and extraction method on Cumin antioxidant activities
In light of the differences among the wide number of the systems available, the results of a single method can give only a reductive suggestion of the antioxidant properties of the extracts [32]. For that reason, we combined two complementary techniques, based on the DPPH radical scavenging assay and the �-carotene bleaching method (Table 3).
The DPPH radical scavenging is a commonly used method to evaluate the ability of plant extracts to scavenge free radicals generated from DPPH reagent [33]. The comparison of total phenolic amounts and IC50 (concentration required to cause a 50% DPPH inhibition) values in seed during their maturation, allowed us to conclude that antioxidant activity depends on the content of total phenolic. In fact, statistical analysis showed that there is a positive correlation between IC50 and total phenolic amounts with r = 0.001 (p < 0.05). So, at mature stage where a high content of total phenolics was detected (17.74 and 25.15 mg GAE/g DW), the antioxidant capacity was increased (6.24 and 42.16 �g/ml), respectively for maceration and soxhlet method, in comparison to other stages such as at immature stage (6.91 and 12.18 GAE/g DW) and the values of IC50 (280.77and 325.15 �g/ml), correspondingly for maceration and soxhlet method (Table 3).
Concerning the �-carotene bleaching assay, the oxidation of linoleic acid generates peroxyl-free radicals due to the abstraction of hydrogen atom from diallylic methylene groups of linoleic acid [34]. The free radical then will oxidize the highly unsaturated �-carotene. The presence of antioxidants in the extract will minimize the �-carotene oxidation by hydroperoxides. These will be later neutralized by the antioxidants from the extracts. Thus, the degradation rate of �-carotene depends on the antioxidant activity of the extracts. Results showed (Table 3) that similarly to the DPPH radical�scavenging capacity measurements and independently of extraction method, mature stage extracts displayed significant higher activity as compared to other extracts. In addition, soxhlet extracts at mature stage exhibits the best activity to prevent the decouloration of � -carotene with IC50 value equal to 122.25�g/ml. Hence, it appears that antioxidant activity could be related to the nature of the compounds and not necessarily to the polyphenol contents.
Effect of the ripening stage and extraction method on phenolic composition
Phenolic compounds are naturally present in fruits and vegetables. They are a part of everyday diet and are also used as medicines or supplements. In our previous study, phenolic composition of cumin seeds was investigated according to their provenances and their extraction solvent [8]. Here, polyphenol qualitative determination in cumin seeds, according their ripening stage and extraction method, were performed by RP-HPLC coupled with an UV�visible multi-wavelength detector. A total of 19 phenolic compounds were successfully identified during the ripening of cumin seeds. Rosmarinic acid was the major phenolic acid for the immature stage with 16.98 and 15.2%, respectively for maceration and soxhlet extracts. Furthermore, intermediate and mature stages were dominated by p-coumaric acid.
Table 4 showed that, independently of extraction method, the proportions of phenolic acids increased with the ripening stage. Conversely we noted a remarkable decrease in the flavonoid proportions which was expressed mainly by the reduction of luteolin and quercetin amounts with maturity stage. Results indicated a significant increase of the biosynthesis of syringic and and p-coumaric acids during ripening, which resulted in the enhancement of their proportions by about 1.53 and 2.19 folds; 3.31 and 2.64 folds, respectively, for maceration and soxhlet method, at mature stage, in comparison with the immature one. On the other hand, gallic acid, which is speci�c to soxhlet extract, is considered as a powerful antioxidant phenolic compound disclosing high scavenging activity [35]. Conversely, catechin was represented only in maceration extract and was probably one of the reasons explaining the highest performances of this one, as all the other identi�ed compounds are common to both maceration and Soxhlet extracts. In addition to catechin, gallic and syringic acids, a strong capacity for the scavenging of the free radicals by the rosmarinic acid has been reported, and the antioxidant activity is over three times that of Trolox [36]. Moreover, vanillic acid is well-known potent antioxidants. However, p-coumaric and trans-2-hydroxycinnamic acids are hydroxycinnamic monophenols [37]. Nevertheless, all the monophenols, apart from BHA, are less effective than polyphenols [38]. On another hand, Table 4 showed that the amounts of polyphenols determinate by Folin�Ciocalteu method was highest than those determined by HPLC method (Table 4). Probably the main cause of the difference obtained by the two methods is the fact that the Folin Ciocalteu method does not provide a speci�c assay for phenolic compounds as it reacts positively with many easily oxidizable non-phenolic compounds [39, 40].
The ripening stage as well as the extraction method significantly affected total polyphenol, falvonoids, tannins and antioxidant activities in C. cyminum seeds. Seeds of the three stage of ripening contained high amounts of phenolic compounds and strong antioxidant activities, which is of high economical significance in the perspective of breeding strategies, selecting provenances and solvents with high polyphenols, flavonoids and tannins contents, and high antioxidant potential for producing specific health-promoting antioxidants in the food industry.



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  ' ( c d { � � � � � &"("�"�"�"��䵚̘����������jVjVjV�&h�*PCJOJQJaJmH	nHsH	tH,hMhMCJOJQJaJmH	nHsH	tH,hMh>V�CJOJQJaJmH	nHsH	tHU5h7Xh>V�B*CJOJQJaJmH	nHph�sH	tH,h7Xh>V�CJOJQJaJmH	nHsH	tH/h>V�B*CJOJQJaJmH	nHphsH	tH5h7Xh>V�B*CJOJQJaJmH	nHphsH	tHi YZ, Sun M, Corke H (2005) Antioxidant capacity of 26 spice extracts and characterization of their phenolic constituents. J Agric Food Chem 53: 7749�7759.
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Table 1. Physical characteristics of cumin seed during ripening
Harvest datesDAFFruit colour, state 
of maturityDry weight
(%)Relative moisture
content (%, w/w)14 May 20115Unripe, fully green10.3�0.06c89.7 � 0.9a29 May 201120Half ripe, green-brown56.4�0.2b43.6 �0.7b27 June 201149Fully ripe, brown87.5�0.6a12.5 �0.6cValues followed by different letters share signi�cant differences at 5% (Duncan test).






















Table 2. Phenolic compounds from cumin seed

ImmatureIntermediateMaturePolyphenol
(mg GAE g"1 DW)Maceration 6.91 � 0.03cB13.21 �0.12bAB17.74 �0.01aBSoxhlet12.18 �0.03cA16.57 �0.04bA25.15 �0.02aAFlavonoid 
(mg CE g"1 DW)Maceration17.93 �0.1aA13.12 �0.01bAB5.83 �0.01cBSoxhlet20.76 �0.02aA17.07 �0.02bA12.12 �0.05cATanin 
(mg CE g" 1DW)Maceration19.33 �0.05cA43.65 �0.11bA68.72 �0.22aASoxhlet7.14 �0.01aB18.77 �0.01bB33.50 �0.12cBTotal polyphenol, �avonoid and tannin contents extracts in immature, intermediate and mature stage obtained by two different methods: maceration and Soxhlet apparatus
Values are means of three replications (N=3�S.D); GAE: gallic acid equivalents, CE: catechin equivalents; The data marked with the different small letter, for the ripening stage,and capital letter, for the extraction method, in the table, value share significant differences at P< 0.05 (Duncan test).




















Table 3. Antioxidant activities of cumin seed

ImmatureIntermediateMatureDPPH scavenging activity
(IC50, �g/ml)Maceration280.77�2.34cA89.17�0.34bA6.24�0.03aASoxhlet325.15�1.83cAB150.17�0.3bB42.16�0.06aB�-carotene bleaching
(IC50, �g/ml)Maceration426.77�1.73cA184.17�0.06bA137.17�0.53aASoxhlet465.17�2.97cAB243.15�0.93bB182.25�0.11aBTotal polyphenol, �avonoid and tannin contents extracts in immature, intermediate and mature stage obtained by two different methods: maceration and Soxhlet apparatus.
Values are means of three replications (N=3�S.D); The data marked with the different small letter, for the ripening stage,and capital letter, for the extraction method, in the table, value share significant differences at P< 0.05 (Duncan test).



















Table 4. Phenolic composition (%) of cumin seed.
ImmatureIntermediateMatureMacerationSoxhletMacerationSoxhletMacerationSoxhletPhenolic acids60.84�0.23cA63.40�0.12cA69.72�0.11bA66.23�0.02bA74.53�0.03aA76.18�0.04aAGallic acid-4.55�0.01b-3.21�0.02b-8.03�0.04aCafeic acid 1.55�0.02bA2.20�0.01aA5.27�0.01aA0.90�0.01bcA0.69�0.01bA0.88�0.02bADihydroxyphenolic acid3.90�0.03aA0.93�0.04bB3.30�0.07aA3.70�0.01aA0.45�0.00bA0.83�0.01bADihydroxybenzoic acid0.06�0.00bcB0.25�0.01abA0.93�0.01bA0.99�0.02aA1.77�0.01aA0.01�0.00bBChlorogenic acid8.97�0.02aA9.66�0.03aA4.92�0.01bA5.12�0.02bA0.97�0.01cA1.22�0.03cASyringic acid6.34�0.04bA�"�"�"�#�#�#�#5$6$i$j$�$�$�$�$�$�$%%"%&%)%B%k%l%�%�%�%�%�%�%����縝������h�����Q����������,h�T�h>V�CJOJQJaJmH	nHsH	tH8h�T�h>V�6�B*CJOJQJaJmH	nHphsH	tH/h>V�B*CJOJQJaJmH	nHphsH	tH5h�T�h>V�B*CJOJQJaJmH	nHphsH	tH0hK�h>V�CJOJPJQJaJmH	nHsH	tH*h>V�CJOJPJQJaJmH	nHsH	tH0h�T�h>V�CJOJPJQJaJmH	nHsH	tH�%�%�%�%�%�%�%&&^&n&q&s&{&|&~&�&�����������s�[@5hEh>V�B*CJOJQJaJmH	nHphsH	tH/h�+�B*CJOJQJaJmH	nHphsH	tH5hEh>V�B*CJOJQJaJmH	nHphsH	tH5h�T�h>V�B*CJOJQJaJmH	nHphsH	tH/h>V�B*CJOJQJaJmH	nHphsH	tH0h�T�h>V�B*CJOJQJ]�aJmH	ph�sH	'h�)�h>V�CJOJQJ]�aJmH	sH	!h�+�CJOJQJ]�aJmH	sH	�&�&�&�&�&�&%'&'?'Y']'^'e'f'g'i'j'k'�'�'�'�'�'�'�'�'(	((8(9(y(z(�(�(�(�������������ѽ�����q��[���������q�*h�+�CJOJPJQJaJmH	nHsH	tH3hEh>V�6�CJOJPJQJaJmH	nHsH	tH5hEh>V�B*CJOJQJaJmH	nHph�sH	tH,h�)�h>V�CJOJQJaJmH	nHsH	tH&h�+�CJOJQJaJmH	nHsH	tH0hEh>V�CJOJPJQJaJmH	nHsH	tH*h>V�CJOJPJQJaJmH	nHsH	tH#�(�(�(�(�(�(�(�(5)>)L)i)t)v)�)�)�)�)(*)*.*/*0*2*p*q*�*�*�*�*�*�*,+,x,z,�,�,�,�,�,�,�,�,`-b-�-�-�-�-�-�-�-�-3.4.z.{.�.�.�.�.�.���ѻ������ѻ��������ѻ������ѻ����ѻ����ꢻ��������0h%D0h>V�CJOJPJQJaJmH	nHsH	tH*h�+�CJOJPJQJaJmH	nHsH	tH0hEh>V�CJOJPJQJaJmH	nHsH	tH*h>V�CJOJPJQJaJmH	nHsH	tH>0*�*�,�-�.�.�.�.�.�.�.�.�.//%/1/</@/R/c/��������������������$d��$Ifa$gdIOgd�P$���V�d��7$8$H$^��`�V�a$gd>V�$���V�d��7$8$H$^��`�V�a$gd�)��.�.�.�.�.�.�.�.1/c/d/�/�/�/�/�/�/�/�/�/�/�/�/�/�/�Ӹ���ӌ|q^O?^O?^q^O?^O?h~E�h�PCJH*OJQJaJh~E�h�PCJOJQJaJ$h~E�h�PCJOJQJaJmH	sH	h~E�h�PCJaJh~E�h�P5�CJOJQJaJ'h~E�h�P5�CJOJQJaJmH	sH	/h�PB*CJOJQJaJmH	nHphsH	tH5h�/�h�PB*CJOJQJaJmH	nHphsH	tH'h�/�h�P5�CJOJQJaJmH	sH	0h%D0h�+�CJOJPJQJaJmH	nHsH	tHc/d/p/r/�/�/B1111$d��$Ifa$gdIO�kd$$IfT�l����r������$�~�H	
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