杨小舟蛾雌蛾性信息素活性成分的鉴定
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摘要
【目的】鉴定杨小舟蛾Micromelalopha sieversi雌蛾性信息素活性成分的结构信息。【方法】采用正己烷浸提的方法提取杨小舟蛾性成熟处女雌蛾性腺中的活性成分;利用气相色谱-触角电位联用(GC-EAD)技术对其活性成分进行定位;性腺提取物与4-甲基-1,2,4-三唑啉-3,5-二酮(MTAD)进行微量化学反应,获得衍生物;利用气相色谱-质谱联用(GC-MS)技术分别对性腺提取物及MTAD衍生物进行质谱特征离子分析。【结果】GC-EAD结果显示,杨小舟蛾雄蛾触角对雌蛾性信息素腺体提取物中的一种成分有较好的反应; GC-MS分析结果表明,能引起雄蛾触角电生理反应的成分为十八碳的不饱和醛; MTAD衍生物的GC-MS结果显示,该活性成分的两个双键分别位于碳链的13和15位。【结论】本研究鉴定出杨小舟蛾雌蛾性信息素活性成分的平面结构为13,15-十八碳二烯醛,但双键的立体构型有待合成标准化合物进一步鉴定。本研究为杨小舟蛾性信息素备选化合物的筛选提供了方向,为信息素的结构确证奠定了基础。
【Aim】This study aims to identify the structure of active components of sex pheromone of female moths of Micromelalopha sieversi. 【Methods】The sex pheromone was extracted from sex glands of virgin female moths of M. sieversi by n-hexane. The active ingredient was located by gas chromatographyelectroantennographic detection( GC-EAD). The additive derivative was obtained by the reaction of the extract from sex glands of virgin female moths with 4-methyl-3 H-1,2,4-triazole-3,5( 4 H)-dione( MTAD). The characteristic ions of the extract and additive derivative were analyzed by gas chromatography-mass spectrometry( GC-MS). 【Results】The GC-EAD results indicated that the antenna of male moth of M. sieversi showed sensitive reaction to one component of the extract from sex glands of virgin female moths. Based on the GC-MS data of the extract and additive derivative,the active component of sex pheromone was identified as 13,15-octadecadienal. 【Conclusion】The identified planar structure of the active component of sex pheromone of female moths of M. sieversi is 13,15-octadecadienal,but the stereoscopic configuration of conjugated double bonds needs to be further identified through synthesizing more standard compounds. This study provides the direction in screening synthetic pheromone candidates and establishes the foundation for determining the sex pheromone structure of female moth of M. sieversi.
【Aim】This study aims to identify the structure of active components of sex pheromone of female moths of Micromelalopha sieversi. 【Methods】The sex pheromone was extracted from sex glands of virgin female moths of M. sieversi by n-hexane. The active ingredient was located by gas chromatographyelectroantennographic detection( GC-EAD). The additive derivative was obtained by the reaction of the extract from sex glands of virgin female moths with 4-methyl-3 H-1,2,4-triazole-3,5( 4 H)-dione( MTAD). The characteristic ions of the extract and additive derivative were analyzed by gas chromatography-mass spectrometry( GC-MS). 【Results】The GC-EAD results indicated that the antenna of male moth of M. sieversi showed sensitive reaction to one component of the extract from sex glands of virgin female moths. Based on the GC-MS data of the extract and additive derivative,the active component of sex pheromone was identified as 13,15-octadecadienal. 【Conclusion】The identified planar structure of the active component of sex pheromone of female moths of M. sieversi is 13,15-octadecadienal,but the stereoscopic configuration of conjugated double bonds needs to be further identified through synthesizing more standard compounds. This study provides the direction in screening synthetic pheromone candidates and establishes the foundation for determining the sex pheromone structure of female moth of M. sieversi.
引文
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Guo TB,Ji BZ,Zhuge Q,Huang MR,2007.Effect of transgenic poplars on the activities of detoxification enzymes in Micromelalopha troglodyta larvae.Sci.Silv.Sin.,43(5):59-63.[郭同斌,嵇保中,诸葛强,黄敏仁,2007.转基因杨树对杨小舟蛾幼虫解毒酶活性的影响.林业科学,43(5):59-63]
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Breuer M,Kontzog HG,Loof AD,2003.The sex attractant pheromone of the oak processionary,Thaumetopoea processionea a field evaluation.Commun.Agric.Appl.Biol.Sci.,68(4 Pt A):203-208.
Buser HR,Arn H,Guerin P,Rauscher S,1983.Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts.Anal.Chem.,55(6):818-822.
Carlson DA,Roan CS,Yost RA,Hector J,1989.Dimethyl disulfide derivatives of long chain alkenes,alkadienes,and alkatrienes for gas chromatography/mass spectrometry.Anal.Chem.,61:1564-1571.
Chen L,Wang GL,Wei HY,2014.Circadian rhythm of emergence and reproduction of Micromelalopha troglodyta(Lepidoptera:Notodontidae).Chin.J.Appl.Ecol.,25(8):2425-2430.[陈琳,王广利,魏洪义,2014.杨小舟蛾的羽化和生殖行为节律.应用生态学报,25(8):2425-2430]
Cheng H,Tang F,Li W,Xu M,2016.Tannic acid induction of a glutathione S-transferase in Micromelalopha troglodyta(Lepidoptera:Notodontidae)larvae.J.Entomol.Sci.,50(4):350-362.
Cook SM,Khan ZR,Pickett JA,2007.The use of push-pull strategies in integrated pest management.Annu.Rev.Entomol.,52:375-400.
Dunkelblum E,Tan SH,Silk PJ,1985.Double-bond location in monounsaturated fatty acids by dimethyl disulfide derivatization and mass spectrometry:application to analysis of fatty acids in pheromone glands of four Lepidoptera.J.Chem.Ecol.,11(3):265-277.
Fan BQ,Lin JH,Hao DJ,Wang Y,Ma FL,2009.Study on biological activity of extracts from female sex pheromone gland of Clostera anachoreta.J.For.Eng.,23(2):64-66.[樊斌琦,林家淮,郝德君,王焱,马凤林,2009.杨扇舟蛾雌蛾性信息素腺体提取物的生物活性.林业工程学报,23(2):64-66]
Fan LP,Huang FQ,Wang HB,Li GH,Kong XB,Zhang SF,2015.Reproductive behavior of Micromelalopha sieversi(Lepidoptera:Notodontidae).Sci.Silv.Sin.,51(8):60-66.[范立鹏,黄范全,王鸿斌,李国宏,孔祥波,张苏芳,2015.杨小舟蛾(鳞翅目:舟蛾科)的生殖行为.林业科学,51(8):60-66]
Fan LP,Zhang Z,Liu YX,Yu ZJ,Kong XB,2014.Factors impacting the emergence rhythm and rate of Micromelalopha sieversi(Lepidoptera:Notodontidae).For.Res.,27(1):53-58.[范立鹏,张真,刘艳侠,于占晶,孔祥波,2014.杨小舟蛾羽化节律及羽化率影响因子分析.林业科学研究,27(1):53-58]
Frérot B,Malosse C,Milat ML,Demolin G,Martin JC,Khemici M,Zamoun M,Gach M,1990.Chemical analysis of the sex pheromone glands of Thaumetopoea bonjeani(Lep.,Thaumetopoeidae).J.Appl.Entomol.,109(1-5):210-212.
Gaston LK,Shorey HH,Saario CA,1967.Insect population control by the use of sex pheromones to inhibit orientation between the sexes.Nature,213(5081):1155.
Guerrero A,Camps F,Coll J,Riba M,Einhorn J,Descoins C,Lallemand JY,1981.Identification of a potential sex pheromone of the processionary moth Thaumetopoea pityocampa(Lepidoptera:Notodontidae).Tetrahedron.Lett.,22(21):2013-2016.
Guo TB,Ji BZ,Zhuge Q,Huang MR,2007.Effect of transgenic poplars on the activities of detoxification enzymes in Micromelalopha troglodyta larvae.Sci.Silv.Sin.,43(5):59-63.[郭同斌,嵇保中,诸葛强,黄敏仁,2007.转基因杨树对杨小舟蛾幼虫解毒酶活性的影响.林业科学,43(5):59-63]
Guo TB,Wang ZY,Liang B,Yang ZL,Qian GZ,Zhou Y,Yu AX,Huang XH,2000.Bionomics of Micromelalopha troglodyta.J.Nanjing For.Univ.(Nat.Sci.Ed.),24(5):56-60.[郭同斌,王振营,梁波,杨中林,钱桂芝,周勇,于爱香,黄秀花,2000.杨小舟蛾的生物学特性.南京林业大学学报(自然科学版),24(5):56-60]
Halperin J,1985.Mating disruption of the pine processionary caterpillar by pityolure.Phytoparasitica,13(3-4):221-224.
Hu M,Xu B,Gao YG,Xue YY,Wang AJ,2016.Control experiment of Bacillus thuringiensis against Micromelalopha troglodyta(Graeser).For.Pest Dis.,(3):45-46.[胡猛,许冰,高玉国,薛玉燕,王安静,2016.苏云金杆菌防治杨小舟蛾试验.中国森林病虫,(3):45-46]
Kong XB,Zhao CH,Zhang Z,Wang HB,2004.Determination of double bond position in conjugated dienes in sex pheromones of Dendrolimus spp.Chin.J.Chrom.,22(2):97-100.[孔祥波,赵成华,张真,王鸿斌,2004.松毛虫性信息素共轭双键定位方法的研究.色谱,22(2):97-100]
Kong XB,Zhao LL,Zhang Z,Wang HB,2010.A simple method to determine the double bond position in monounsaturated insect pheromone compounds.Acta Entomol.Sin.,53(6):634-639.[孔祥波,赵莉蔺,张真,王鸿斌,2010.一种用于昆虫性信息素成分单不饱和双键定位的简便方法.昆虫学报,53(6):634-639]
Liang ZP,Zhang XX,Song AD,Peng HY,2006.Biology of Clostera anachoreta and its control methods.Chin.Bull.Entomol.,43(2):147-152.[梁振普,张小霞,宋安东,彭辉银,2006.杨扇舟蛾的生物学特性及其防治方法.昆虫知识,43(2):147-152]
Ma T,Lin N,Zhou LL,Shi XH,Zhou QH,Wang C,Sun CH,Chen XY,He YR,Wen XJ,2018.Research progress and application prospect of insect sex pheromone mating disruption.For.Res.,31(4):172-182.[马涛,林娜,周丽丽,史先慧,周秋宏,王偲,孙朝辉,陈晓阳,何余容,温秀军,2018.性信息素迷向干扰防控害虫的研究进展及应用前景.林业科学研究,31(4):172-182]
Mc Elfresh JS,Millar JG,1999.Sex pheromone of the common sheep moth,Hemileuca eglanterina,from the San Gabriel Mountains of California.J.Chem.Ecol.,25(4):687-709.
Mori BA,Evenden ML,2015.Challenges of mating disruption using aerosol-emitting pheromone puffers in red clover seed production fields to control Coleophora deauratella(Lepidoptera:Coleophoridae).Environ.Entomol.,44(1):34-43.
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