马尾松叶生化物质的生物检测与物质鉴定

西北植物学报,2006,26(4):0811-0818Acta Bot. Boreal -Occident. Sin文章编号:1000-4025(2006)04-0811-08马尾松叶生化物质的生物检测与物质鉴定曹光球',林思祖,胡宗庆?,王爱萍l,彭亦如(1福建农林大学林学院,福州350002;2福建林业职业技术学院,福建南平3530003福建师范大学化学与材料学院,福州摘要:马尾松是我国特有的乡土树种,长期林业生产实践表明马尾松纯林连栽会引起马尾松生产量下降。本实验采用超临界萃取技术提取马尾松叶生化物质,并采用马尾松种子发芽试验进行生物检测及物质鉴定。生物检测结果表明,纯CO2提取的马尾松叶生化物质以及乙醇和CO2混和提取的马尾松叶生化物质对马尾松种子的发芽具有不同的效应。总体效果而言,纯CO2提取的马尾松叶生化物质对马尾松种子发芽率、胚根长、鲜重和干重具有不同程度的抑制效应,而对发芽势及胚轴长则具有促进效应;乙醇和CO2混和提取的马尾松叶生化物质对马尾松种子发芽率、胚轴长、鲜重和干重具有不同程度的抑制作用,而对发芽势及胚根长则具有促进作用。物质鉴定结果表明纯CO2提取的马尾松叶生化物质主要是苯甲醛、Cis-2,6-二甲基-2,6-辛二烯等,乙醇和CO2混和提取的马尾松叶生化物质主要是β芳樟醇、苯乙醇等。关键词:马尾松;化感作用;生物检测;GCMS分析;超临界提取中图分类号:Q946-33文献标识码:ABio-detection and ldentification of Biochemical Substancesin Pinus massoniana leavesCAO Guang-qiu, LIN Si-zu', HU Zong-qing WANG Ai-ping, PENG Yi-ru(I Forestry College. Fujian Agriculture and Forestry University, Fuzhou 350002. China: 2 Fujian Forestry Professional andTechnological College, Nanping, Fujian 353000, China: 3 Chemical and Material College, Fujian Normal University Fuzhou350007. ChinaAbstract: Pinus massoniana is a specific landrace species and long- term production practices of forestry indicate that the continuous cropping of pure P. massoniana forests can result in decreased P. massonianayields. This study adopted Supercritical Fluid Extraction to extract biochemical substances from P.masso-nana leaves and germination test to biologically detect and identify these substances. The results of thebio-detection indicated that the substances extracted only with CO, and the substances extracted with themixture of CO2 and ethanol showed different effects on the germination of P. massoniana seeds. as awhole, the substances extracted only with only CO2 appeared to inhibit the germination rate and radiclelength and fresh and dry weight of P. massoniana seeds to a varying extent but to increase the germinationpotential and hypocotyl length of the seeds and the substances extracted with the mixture of co2 andethanol appeared to inhibit the germination rate and hypocotyl length and fresh and dry weights of P. massoniana seeds but to increase the germination potential and radicle length of the seeds. The results of the i-中国煤化工收稿日期:20040927;修改稿收到日期:2006-03-基金项目:国家自然科学基金项目(3027107)福建省自然科学基金项目(BCNMHG作者简介:曹光球(1974-)男,助理研究员,博士生,主要从事化学生态等领域的研究通讯联系人。Correspondenceto:LINSI-zu.E-mail:selin53@126.com西北植物学报26卷dentification revealed that of the substances extracted only with CO2, the major ones were benzaldehydeand cis-2, 6-Dimethyl-2, 6-octadiene and of the substances extracted with the mixture of CO2 and ethanolthe ma jor ones were B-linalool and phenethyl alcoholKey words: Pinus massoniana; allelopathy GC-MS; Supercritical Fluid ExtractionAllelopathy is one of the most common phe- cals against itself, and according to the results ofnomena in nature. Rice gave the following defini- bioassay, allelochemicals were identified, so as totion of allelopathy " any direct or indirect harmful find out the chemical factor which lead to loweror beneficial effect by one plant (including mi- productivity.croorganisms )on another through the production1 Materials and methodsof chemicalat escape into the envi-ronment"n. Putnam and Tang 2 stated that chemi- 1. 1 Collection and treatment of the materialscals with allelopathic potential were present in virP. massoniana leaf was collected from the puretually all plant tissues, including leaves, flowers, P. massoniana stand in the vicinity of Fujian Agri-fruits, stems, roots, rhizomes and seeds. Allelo- culture and Forestry University, Fujian Provincechemicals were released by processes with China. The samples were dried at room temperavolatilization, root exudation, leaching, and decom- ture in a desiccation. P. massoniana seeds were ofposition [31fered by Fujian Forestry Office.Pinus massoniana recommended as one of the 1. 2 Extraction of the allelochemicals of P.masso-most important timber tree species in China is a nana leafkind of native tree species, it spreads through fifAllelochemicals of P. massoniana leaf were ex-een provinces of southern China. Long-term yield- tracted by the method of supercritical CO2 extrac-ing practice suggested that pure forest of P. masso. tion under orthogonal experiment design. Orthogo-nana had many shortcomings, such as simple nal experiment data and supercritical CO2 extrac-structure, bad ecological quality, weak fire guard- tion condition were showed in Table 1. Firstly,alleing ability,et al. With the further study of P. mas- lochemicals were extracted by pure CO2, and thensoniana, more and more researchers motioned that residual allelochemicals were extracted by ethanolP. massoniana would lead to lower productivity mixed with CO,; Supercritical CO2 extraction hadwhen grown after itself' land again 4. 5. In this the function of isolation, in order to use this charstudy,after allelochemicals of P. massoniana leaf acteristic, isolation pressure was set at 2 MPa. Fiwere extracted by supercritical CO, extraction, nally, the allelochemicals were concentrated underbioassay of P. massoniana seed germination was vacuum at room temperature.used to test the allelopathic activity of allelochemiTable 1 Allelochemicals under different conditions of supercritical CO2 extractionFactorTime(kg/h)30±230±345±230±2中国煤化工50士345±2CNMHG30士350士345±24期曹光球,等:马尾松叶生化物质的生物检测与物质鉴定(英)8131.3 Confection of experimental additivesafter keeping at 220C for 2 min, the temperatureAllelochemicals extracted by pure CO2 and was raised again to 270C with the ratio of 15-C/CO2 mixed with ethanol were dissolved by ethanol min and retained this temperature for 2 min. Theto obtain solutions with different concentrations of unknown compound was searched by handwork50,100 and 200 mg. kg, all of the experimental2 Resultsadditives'concentration of ethanol were V(ethanol): V(distilled water)=I: 100 Control was 2. 1 Effects of allelochemicals extracted by pureethanol with the concentration of 1 100CO, on seed germination1. 4 BioassayExperimental results showed that the allelo-Seed germination of P. massoniana was con- chemicals extracted by pure CO2 under different exducted in petri dishes at laboratory temperature traction conditions had different effects on seed(27 C) and relative humidity of 60%. Each treat. germination; Under the same extraction condiment was replicated three times, with 100 seeds per tions, the different concentrations of allelochemireplication on filter paper. Germination experiment cals also had different effects(Table 2). As far aswas lasted for 20 days. The results of seed germi- the different extraction conditions were concernednation bioassay were expressed as germination for condition 1, condition 2 isolation I, conditionrate, germination power, radical length, fresh isolation I, the inhibitory effect of allelochemicalsweight, and dry weightbecame stronger with the increase of concentra1. 5 Data processingtion: Condition 2 isolation I showed that the in-t-test was used to analyze whether the differ- hibitory effect became weaker with the increase ofence of treatments were remarkable. The germina- concentration; Condition 3 isolation Ition rate was calculated as: The germination ratetion 4 showed that 200 mg. kg had the strongestthe total of germination mumber/100 X100%. The inhibitory effect than those of 500 and 100 mggermination power was calculated as: The germina- kg ' The indices of seed germination were differ-tion power the amount of germination on the ently sensitive to the allelochemicals extracted unpeak day of germination/100X100%der different extraction conditions and to different1.6 Identificationconcentrations. For example, concentration of 500GC-MS analysis was performed on the agilent mg.kg extracted by condition 1 isolation I had5973N GC chromatogram instrument which e- stimulatory effect on germination power, but hadquipped with 6890 gas chromatography, automatic inhibitory effect on germination rate, plumular rootimplus implement, and J &. W DB-35MS capillary length, plumular axis length, fresh weight and drychromatograph column (30 m 0. 25 mm X O 25 weight; concentration of 500 mg. kgextractedum). The higher purity He was used as carrier by condition 2 isolation I had stimulatory effect on(content higher than 99. 999%), diffluent ratio of germination rate, but had inhibitory effect on gergas was 50 1. Temperature of feed nozzle was mination power, plumular root length, plumular ax260 C. PFTBA was used to autotune ion selected is length, fresh weight and dry weightdetector. The ionization method was El, energy was 2. 2 Effects of allelochemicals extracted by70 eV. Date was collected by scan method, The ethanol mixed with CO2 on seed germinationtemperature of joint between the gas between MsAllelochemicals obtained by ethanol mixedourceIon and quardrupole werewith中国煤化工 on conditions had230C and 150C respectively. Sequence programme differeCNMHGIOn, and differentof chromatographic column was 100C at which concentratauelocnerncuis extracted undermperature was kept 2 min, then it was the same condition also had different effects (tableraised to 220C in 2 min at the rate of 20 C/min, 3).II, for conditions 1, 2, 4, the low con-814西北植物学报26卷centration of 100 and 200 mg. kg, allelochemi- ferent index of seed germination had different sen-cals showed the stimulatory effect on some indices; sitive to allelochemicals extracted by different con-With the concentration rising, the inhibitory effects ditions and with different concentrations. As fogot stronger; For condition 3 isolation I showed concentration of 500 mg.kg under conditionthat the inhibitory effect got weaker with the in- isolation I the results showed that allelochemicalscrease of concentration: condition 3 isolation Ihad inhibitory effects on absolute germinationshowed that 200 mg. kg i had the strongest in- rate, absolute germination power, plumular roothibitory effect than that of 500 and 100 mg. kg"; length, fresh weight and dry weight, but had stimu-In term of different indices of seed germination, dif- latory effects on plumular axis lengthTable 2 Effect of allelochemical of P. massoniana leaf extracted by pure COon P. massoniana seeds germinationGerminationPlumularPlumulaFreshDryIndexpowerweightRIRIRItRIItI1Aa0.26·5.690.090.650.34·3.040.201.89-0.46··271Ab-0.179.620.53··5.790.41·7.700.211.62-0.50··7.79-0.45·10.97179.830.210.970.23·3.42-0.150.69-0.05650.100.010.040.960.99-0.5IBe0.040.330.150.52-0.21·4.80-0.36··6.98-0.2Aal.120.2548-0.333.630.020.14-0.2757-0,110.672Ab0.040.440.262.570.120.1.440.020.180.493.8823150.120.10-0.18·18.900.070.62-0.2712.20-0.171.68l.130.35·3.170.171.45-0.010.11-0.302Bc0.363.400.071,36-0.091.870,020.34-0.430.771.790.080.35·3.310.171.630.264.25-0.612.050.140.05··5.31-0.40··32.220.00.8.77-0.373.68-0.192.120.481.690.06·40.333.03Bb0.171.150.551.67211.34-0.313Bc0.040.380.481.46-0.302.320.312.06-0.251.390.920.1312-0.26·3.480.44-0.034Ab2.140.31·7.060.040.41-0.365.004Ac-0.020.980.480.61-0.35·*17.41-0.060.68-0.31·14.72-0.1076.97021.070.172.41.880.794BE120.9930.57·16.910.151.250.050.1.80-0.2l2,140.104210.26··10.070.04Sum of riNotes: The results are expressed as the mean value of 3 replicate. Value of RI is the sensitivity index of allelopathy put forward bywilliamson:RI=l-C/T(T>C).RI-TC-I(TsC).C is the Value of control T' is the value of treatment. RI>O indicate stimulation, RI<0 indicate inhibition. The absolute value of RI stands for the intensity of allelopathy[6]. 1,2, 3, 4 which corresponding to Table I represents different extraction conditions. A represents allelochemicals collected from isolation I B represents allelochemicals collected from isolationI:a,band c represents the concentration of 1 100 mg/kg, 200 mg/kg and 500 mg/kg: P<0. 05.*0.01,Tam=4.303,Ta.01=9.925.Thefollowing table is the same.Table 3 Effect of allelochemical of P. massoniana leaf extracted by ethanol mixedwith CO on P. massoniana seed germinationGerminationPlumularpoweyimengroot lengtweightRIRItR0.24·4.29-0.200.23中国煤化工1-0.070.50,210.18·3.35T-0.32*·5.20-0.014.27-0.232.52CNMHG4二023250,500.232.020.232.0029-0.67·12.03-0.657.37-0.62··24,67-0.42··4.770.658.190,67··20.004期曹光球,等:马尾松叶生化物质的生物检测与物质鉴定(英)续表3 Continued of table30.000.0114.050.25…8.820.221.35-0.070.310.640.32·3.130.372.322.94-0.180.405.550.052.540.34·3.69-0.453.03-0.36·5.420.43·3.710.353.130.23·3.88-0.210.322.630.405.270.1721.28-0.42·4.820.434.273Aa0.352.76-0.32·3.59-0.00.352.421.25-0.060.33·5.25-0.18·4.51-0.2.07-0.211.230.320.590.38·5.280.140.940.96·4.490.231.220.400.201.082.26-0.27·4.23-0.111.050.100.91-0.190.740.372.480.23·6.97-0.2.19-0.18·2.914Aa0.17··5.44-0.14··42.890.242.030.3081100.510.100.624Ab0.49-0.173.593.780.324.05-0.492.410.331.85-0.110.76-0.101.20-0.30··6,000.210.62··13.950.200.221.630.313.74-0.393.35-0.010.04-0.l0.140.2513.170.113.001.04-0.501.842.340.42·4.72Sum of rr6.6l3.4l6.562.3 Identification of allelochemicals of P. masso- under condition 1 isolation I extracted by ethanolnana leafmixed with CO, were further identifiedAccording to results of bioassay, allelochemiGC-Ms analysis results showed that allelo-als showed the most inhibited effect on seed ger- chemicals extracted by pure CO2 were B-linaloolmination were be selected to be further identified. propyl benzene-ol, et al(Table 4);AllelochemicalsBased on results of bioassay, allelochemicals of 500 extracted by ethanol mixed with CO2 were benzenemg. kg under condition 2 isolation I extracted formaldehyde, cis-2, 6-dimethyl-2,6-octadiene,et alby pure CO2 and allelochemicals of 500 mg. kg (Table 5)70000006500000600000055000002025450000035000003000002].182000000150000013001000000I5.I25000004.006.008.0010.00120014.00Time(mYH中国煤化工02400CNMHGFig 1 Tatal ion figure of P. massoniana leaves'allelochemicals extracted by pure CO 2816西北26卷Table 4 Allelochemicals of P. massoniana leaf extracted by pure CO2Molecular formula(min)CompoundsCis-2, 6-dimethylC1H8(138)19.51 Phenol. 2-(1-phenyl ethyl)C14H1O(200)Methyl-butanolCH12O(88)19.80Hexadecanoic acidC16H32O2(246)10Benzenic ethanolC,H,O(108)25 Benzene ethylphenoxyC3H12O(184)13.12 Thiophene 2, 5-dihydroC4HS(84)Hexadecen-I-oCrsH32O(228)Geranyl acetoneCH3CO2C1H17(196)21.40R)-phytolC2H42O(312)15.5CsH12O2(1140)22.02Elaidic acidC17H3,H(282)15.90 1-phenylpropane-1 3-diolCgH10O2(138)22.0616.78 Caryophyllene epoxideC1sH21(O(220)22.12 9.12-octadecadienoic acidCisHi O2(280)17.35Actindiolide dihydrCH10O3(130)22.3CIH: O,(299)18.03Tetradecanoic acidC4H2O2(228)23.04CoH1O2(312)18.083.7,11, 15-tetramethylC19H4O(285)3500022.12日250002000015000100008.0010.0012.0014.0016.0018.0020.0022.0024.00Time(min)Fig 2 Total ion figure of P. massoniana leaves allelochemicals extracted by ethanol mixed with CO:Table 5 Allelochemicals of P. massoniana leaf extracted by extracted by ethanol mixed with COzTimeCompoundMolecular formulaCompoundMolecula(min)P-linaloolC1oH18((15416.16(-)-spathulenolCisH2NO?(240)ropyl benzene-olC1nHO(122)CsH2O3(256)10inderalC1H2O(170)7.34Tau-muurololC14H26O3(230)l1.62L inalyl anthranilateC1rH24NO2(274)aucadinol12.45Borny lacetatC1zH20O2(196(-)-8-cadinolCH32O3(256)copanCzoH3o(270)a-cadinolC15H2O2(256)3-bourboneneCH1zO2(152)20.14n-hexadecanoic acidC1H32O2(254)CH24O2(21620.49 Cinnamic acid, (r)-3-hexenylCaHO2(148)13.84C1H28(196)Benzoic acidCH4O2(122)caryC1sH24(204)r-phenylethyl esterCnH1O(122)14.54C1sH24(204)21.12C1a3H2O(196)14.80C1H32O3(270中国煤化工Coha()(312)a-muuroleneC14H26O3(230CNMHG CHa O2(331)C16H32O2(270)22.48C2sH60(408)15.48Butyl-hydroxytolueneC1oH14O)(150)ualeCaH35(416)Eudesma-4(14)-I1-dicneCtH24(204)2- oxomaroyl oxideC2H56O2(424)曹光球,等:马尾松叶生化物质的生物检测与物质鉴定(英)It has been demonstrated that allelopathy3 Discussionplayed an important role in the dominant growth ofMethod of extraction was an important factor some plant species and the formation of plant com-allelopathy research. Water extraction and or- munities. Many tree species has autointoxication.ganic solvet extraction were widely used lately But Aqueous extract of tea plant stem, leaf, root had in-these method of extraction had shortcomings as ex- hibitory effect on the germination and seedlingtracting incompletely and polluting environment. growth of tea plant 2; Exudates and extracts ofSupercritical CO2 extraction was the new extraction continuously cropped soybean had apparently in-method up to date, and it was also widely used to hibitory effect on the growth and physiological ac-extracting the effective components of Chinese tra- tivities of second-batch seedlings), Tomato had anditional medicine. In this paper, this new method autotoxic effect 14. In term of the study of Chinesewas used to extract the allelochemicals of P. masso- fir autointoxication, aqueous extracts of surfacesoil, leaf litter, half decaying leaf litter, fresh leafDe(7(1832)ascribed the problem of branch, bark and root of Chinese fir had inhibitorythe toxic exudates produced by effect on seeds germination of Chinese fir(1s-17Incrop plants. Since then, much effort has been de- this study, under different conditions of supercriti-voted to the evaluation of root exudates as the cal cO, extraction, the allelochemicals of P. masso-source of allelochemicals. McPherson and Thomp- nana extracted by pure CO, had stronger inhibito-son((1972) demonstrated that an upland forest of ry effects on P. massoniana seed germination thanQuercus stellata and Q. marilandica suppressed the those of extracted by ethanol mixed with COgrowth of understory plants, one of the causativeAllelochemicals are mostly secondary metabo-factors might be related to allelochemicals pro- lites. These allelochemicals range from simple gasduced by their root and leaves. Frei et al[9(1972) es, aliphatic compounds, to complex aromaticfound that the bark of Q. peduncularis, Q. scyto- acids, including acetic and but yric acids, long chainphylla and Q. magniliaefolia contained toxic or in- fatty acids, simple phenols, phenolic acids derivedhibitory substances that inhibitory the growth of from cinnamic and benzoic acids-i8J. As far as theorchids. Gliessman[10](1978)reported that the ex- kinds of allelochemicals of P. massoniana were con-tracts of green leaves and freshly fallen leaves of cerned, the allelochemicals of P. massoniana exQ. eugeniaefolia were toxic to cucumber seedlingtracted by pure CO, were identified as benzeneLodhi(1978)reported that Q. alba, Q borealis formaldehyde, cis-2, 6-dimethyl-2, 6-octadiene etand some other species of plants produced allelo- al; the allelochemicals of P. massoniana extractedchemicals in their leaf litter and soil under the by ethanol mixed with CO2 were identified as B-tree. 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