几种藓类植物的挥发性化学成分分析
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摘要
五倍子具有重要经济意义,藓类植物作为倍蚜虫的冬寄主,对五倍子的产量有重要的影响。但过去的研究很少涉及倍蚜虫与其冬寄主植物之间相互关系的细节。因此,本研究以冬寄主植物挥发性次生物质与倍蚜虫迁飞行为关系作为研究方向,通过收集、检测和分析寄主植物所产生的植物挥发性次生物质,采用溶媒法、水蒸气蒸馏法和GC/MS等现代研究手段,以寻找对倍蚜虫迁飞和寄主定位具有引导功能的特定化学成分,为我国五倍子人工培植技术革新提供理论依据。
     通过一系列的研究分析,主要结果如下:
     1.本研究运用浸提法和水蒸汽蒸馏法提取并分析了5种五倍子蚜虫冬寄主藓类植物的101种挥发性化学成分,涵盖了醇、醛、烯萜类等七大化合物。其中,湿地匐灯藓(Plagiomnium acutum (Lindb.) T. Kop.)获得了81种化学成分,侧枝匐灯藓(Plagiomnium maximoviczii (Lindb.) T. Kop.)测得55种,二者化学成分中含量较高的是1-辛烯-3醇、β-柏木烯和布黎醇,体现二者作为同属植物具有共同的化学特征。大羽藓(Thuidium cymbifolium (Dozy et Molk.) Dozy et Molk.)40种,含量较高的是庚醛,1-辛烯-3-醇,壬醛等。大灰藓(Hypnum plumaeforme wils.)和褶叶青藓(Brachythecium salebrosum (Web. et Mohr.)B. S. G.)分别测得化学成分37和34种,前者成分中含量较高的是1-辛烯-3醇,棕榈酸甲酯和二十九烷;后者成分中含量较高的主要是1-辛烯-3醇、二十四烷、庚醛等化合物。1-辛烯-3醇是所测藓类植物的共同成分,属于脂肪族不饱和醇,可用于调味香精和昆虫引诱剂。
     2.1-辛烯-3-醇,布黎醇和β-柏木烯是湿地匐灯藓和侧枝提灯藓共同的含量较高的成分。它们还同时含有柠檬烯、菖蒲二烯、大根香叶烯B、α-芹子烯、α-长叶蒎烯和蔚西醇等萜类成分,而萜类成分主要是由植食性昆虫诱导植物产生的。据此,可推断角倍蚜迁飞时,很有可能就是利用这些化合物通过不同浓度配比组成的特定的化学信息来寻找冬寄主植物的。
     3.101种成分中有40种萜类成分,包括9种单萜和32种倍半萜,其中β-elemene,β-H-cedran-8-ol,β-cedren-9-a-ol, Di-epi-α-cedrene, y-elemene和trans-1,10-dimethyl-trans-9-ol等化合物在以往的藓类植物化学成分研究中未有报道,本研究在一定程度上丰富了藓类植物(Musci)萜类化学成分的研究资料。
     4.本研究发现藓类植物较苔类植物具丰富的C23-C33奇数碳正链烷(二十三烷、二十七烷和二十九烷)和C15以上的非正链烃,为藓类植物比苔类植物(Hepaticae)更接近高等植物的理论提供了新的、直接的科学证据。
     5.所测藓类植物中发现了多种脂肪酸成分,包括棕榈酸甲酯,亚麻酸乙酯,亚油酸乙酯和花生四烯酸。其中,花生四烯酸少见于高等植物中,是前列腺素的一种活性前体,这为在藓类植物中寻找活性化合物提供了科学依据。
     6.本研究除发现了常见于高等植物的绿叶性气味物质(己醛、己醇等)之外还发现了大量的醛、醇、酮类化合物及一些呋喃衍生物,极大的丰富了藓类植物挥发性化学成分种类资料。
     7.实验中发现水蒸汽蒸馏法结合正己烷萃取藓类植物挥发性成分,具有萃取时间短,萃取成分全面,实验仪器简单等优点。
Gall is an economical raw material, whose winter host plant are mosses. These plant have an important influence on the quantity production of gall. Previous studies have rarely involved the relationship between aphids and their host plants. So several experiments were adopted to extract the volatile organic compounds from mosses. The compounds in these mosses have been separated and identified by gas chromatography and mass spectrometry. This study focused on finding out the particular chemical compositions which can be used by gall aphids to find their host plants, in order to providing the theory basis for technological innovation of gall's artificially propagated.
     The conclusions are as follows:
     1. A total of 101 essential oil compounds from the five mosses have been identified, including seven categories like ketones、alcohols、aldehydes、esters、alkyls、terpenoid and some other constituents. Among these compositions, there were 81 constituents were observed in P. acutum,55 in P. maximoviczii. And the major components of essential oils in P. acutum and P. maximoviczii were 1-octen-3-ol, bulnesol, andβ-cedrene, which showed the same chemical characters of one genus。40 kinds of chemical compounds in T. cymbifolium, its major components of essential oil were heptana 1-octen-3-ol and nonanal. 37 constituents were observed in H. plumaeforme included the major components like 1-octen-3-ol、palmitic acid, methyl ester and nonacosane.34 compositions in B. salebrosum., and the major components were 1-octen-3-ol、tetracosane and heptanal. We found 1-octen-3-ol was very commom in these five mosses, and this kind of componets can be used as essence and insectival attrahent.
     2. The major components of essential oils in P. acutum and P. maximoviczii were 1-octen-3-ol, bulnesol, andβ-cedrene. Both they also have some other terpenes like (+)-(R)-limonene、acoradiene、germacrene B、α-selinene、(+)-a-longipinene、verticillol and so on. Those compostions were created by plant for insectival sitmulate. So, we concluded that those compounds stand a good chance as the constituents of chemical infromation to help Schlechtendalia chinensis found its food plants.
     3.101 kinds of compounds including 40 terpenes (8 kinds of monoterpenoids and 32 sesquiterpenoids belong to 19 types) (3-elemene,β-H-cedran-8-ol,β-cedren-9-a-ol, Di-epi-a-cedrene, y-elemene and trans-1,10-dimethyl-trans-9-ol haven't been reported ago. So our research enriched the study of terpenes in mosses.
     4. Current research showed that the mainly positive chains were C23-C33 odd chain alkanes in higher plants (including ferns), and we found mosses have more C23-C33 odd number alkanes, so we could see that mosses might be closer than liverworts to ferns and seed plants.
     5. Fatty acids like arachidonate, linoleic acid ethyl ester and linolenic acid ethyl ester and so on. The arachidonate is a kind of long-chain insoluble polymer fatty acid in mosses, which is one of the precursors of prostaglandin with high activity. It is significant to search for this natural ingredient by detecting the chemical composition of bryophytes for this fatty acid which does not exist in higher plants
     6. This study reported a number of common volatile compounds of mosses. Some of them were green leaf volatiles and have been reported in the higher plants widely, such as hexanol and hexanal. And also found considerable ketones、alcohols and adehydes, enriched the research of volatiles organic compounds in mosses.
     7. It is discovered in the experiment that steam-distilled combined n-hexane can got a good extraction effect.
引文
[1]杨子祥.五倍子蚜虫(Homoptera:Aphididae)的系统发育研究[D].北京:中国林业科学研究院,2006:7-8.
    [2]邱建生,漆云庆.五倍子蚜虫又一夏寄主滨盐肤木寄主地位的确定[J].贵州林业科技,1990,18(4):8-13.
    [3]赵拉.五倍子制备没食子酸的研究进展[J].化学与生物工程.Chemistry& Bioengineering,2008,25 (5):5-7.
    [4]季梦成.从寄主种类及分布看江西五倍子生产前景[J].江西林业科技,1995a,5:5-8
    [5]丘凤波.角倍蚜生物学观察[J].广西植保(4),1994,14-17.
    [6]李志国,杨文云,夏定久.中国五倍子研究现状[J].林业科学研究,2003,16(6):760-767.
    [7]陈爱萍,邱建生.倍蛋蚜生活史及生物学习性研究初报[J].贵州林业科技,1987,3:11-14
    [8]漆云庆,邱建生.几种五倍子蚜虫的生活周期型研究[J].贵州林业科技,1990,18(4):1-7.
    [9]田泽君,隆孝雄,谢树明,等.枣铁倍蚜无翅孤雌侨蚜的发现及其经济意义[J].西南农业学报,1992,5(2):74-78.
    [10]张沈龙.福建引种角倍蚜生物学特性研究初报[J].福建林学院学报,1996,16(1):41-44.
    [11]胡福生.五倍子蚜养殖技术[J].中国林副特产,1998,4:24.
    [12]李志国,夏定久,吴昊.肚倍蚜人工培育技术研究[J].特产研究,1998,2:1-5.
    [13]韩学俭.角倍蚜的人工繁殖技术[J].中国农村科技,2002,3:27.
    [14]李勇民,田泽君.国外五倍子研究进展[J].四川林业科技.1993,14(3):35-39.
    [15]唐觉.浙江省五倍子繁殖增产研究[C].浙江:浙江农业大学、浙江农业科学院,植物保护部分,1960:91-93.
    [16]唐觉.五倍子及其繁殖增产的途径[J].昆虫学报,1976,19(3):282-296.
    [17]刘应迪,李菁,石进校.湘西山区五倍子林生态模式[J].吉首大学学报(自然科学),1994,15(6):80-84.
    [18]武显维,康宁,丁朝华.藓类植物对角倍蚜越冬生长的影响[J].中南林学院学报,1996b,16(3):29-33.
    [19]贵州省五倍子研究协作组.新的五倍子蚜虫冬寄主[J].贵州林业科技,1984,2:17-54.
    [20]林余霖,程惠珍,陈君.倍蚜虫冬寄主藓类植物的初步研究[J].中药材,1996,19(9):433-434.
    [21]杨比伦,李永和,李坚强,等.丰都县五倍子自然资源初步调查与研究[J].西南林学院学报,1994,14(2):103-114.
    [22]季梦成,李春鲁.江西五倍子蚜虫冬寄主的初步研究[J].江西农业大学学报,1995b,17(2):215-221.
    [23]刘应迪,李菁.湘西五倍子蚜虫冬寄主藓类植物的种类资源[J]. 吉首大学学报(自然科学),1992,13(6):30-33.
    [24]刘应迪,李菁.湖南枣铁倍蚜和蛋铁倍蚜两种新冬寄主藓研究[J].林业科学研究,1993a,6(3):306-310.
    [25]马沛勤,周玉亭,滕红梅,等.山西省五倍子资源调查研究初报[J].昆虫知识,2001,38(3):205-207.
    [26]王道植,李勇民,朱忠荣,等.五倍子蚜虫冬寄主藓类植物组织培养研究初报[J].贵州农学院学报,1989,1:30-38.
    [27]刘应迪,李菁,石进校.湘西五倍子蚜虫冬寄主藓类植物的筛选与人工培植[J].吉首大学学报(自然科学),1993b,12,14(6):16-21.
    [28]武显维,丁朝华,康宁.湿地匐灯藓切茎繁殖研究[J].武汉植物学研究,1996a,14(1):82-88.
    [29]丁治国,张云松.不同叶面肥对湿地匐灯藓萌发及生长的影响[J].贵州林业科技,1999,27(2):44-47.
    [30]司徒春南,王健,喻理飞.不同环境条件下角倍蚜冬寄主无性繁殖研究[J].贵州科学,2007,25(1):39-42.
    [31]刘应迪,李菁,陈军.两种五倍子蚜虫冬寄主藓类植物的光合特性及其与光照、温度和植物体水分含量变化的关系[J].应用生态学报,2000,11(5):687-692.
    [32]刘应迪,曹同,陈军,等.两种匐灯藓属植物夏季和冬季光合特性的比较研究[J].应用生态学报,2001,12(1):39-42.
    [33]Liu Y. D., Z. Y. Li, T. Cao, J. M. Glime. The influence of high temperature on cell damage and shoot survival rates of Plagiomnium acutum. Journal of Bryology,2004,4(26):265-271.
    [34]Zinsmeister, H. D., H. Becker & T. Eicher. Bryophytes, a source of biologically active, naturally occurring material[J]. Angewandte Chemie International Edition in English,1991,30:130-147.
    [35]Asakawa Y. Recent advances in phytochemistry of bryophytes-acetogenins, terpenoids and bis (bibenzyl) s from selected Japanese, Taiwanese, New Zealand, Argentinean and European liverworts[J]. Phytochemistry,2001,56:297-312.
    [36]沙伟,韩继臣.16种苔藓植物对植物病原菌的抑菌性研究[J].食品科技.2009,34(5):213-217.
    [37]吴昆,肖春旺.贵州4种藓类植物的抑菌作用比较[J].贵州师范大学学报(自然科学版),1998,16(4):25-28.
    [38]衣艳君.苔藓植物的抑菌性研究[J].淄博学院学报(自然科学与工程版),2001,3(3):78-80.
    [39]朱灵红,刘俊华,许杰.4种苔藓植物水提液对玉米种子萌发及幼苗生长的影响[J].种子,2010,29(4):83-86.
    [40]王书平,刘俊华.3种苔藓植物水提液对小麦种子萌发的化感效应[J],2010,38(9):51-53.
    [41]陈圆圆,郭水良,娄玉霞,等.大金发藓和小蛇苔化学他感作用的 生物测定[J].植物研究,2009,29(1):108-112.
    [42]张莉娜,杨好伟,罗丽华,等.5种藓类植物水提液对黄瓜幼苗生长的影响[J].热带作物学报,2010,31(3):485-491.
    [43]Adam KP, Croteau R. Monoterpene biosynthesis in the liverwort Conocephalum conicum:demonstration of sabinene synthase and bornyl diphosphate synthase[J]. Phytochemistry,1998,49:475-480.
    [44]周江煜.苔藓植物的化学活性成分研究概况[J].广西中医学院学报,2002,5:84-87.
    [45]Zinsmeister HD,王洁.苔藓植物是生物活性物质的一个资源吗?[J].国外医药·植物药分册,1994,15:87-92.
    [46]Srikrishna A, Babu NC, Rao MS. A stereoselective total synthesis of (+)-a-herbertenol[J]. Tetrahedron,2004,60:2125-2130.
    [47]Dividson A J, Harboranne J B, Longton R E. Identification of hydroxycinnamic acid in Mnium harmun and Brachythecium rutablum and their possible role in protection against herbivory[J]. Journal of the Hattori Botanical Laboratory,1989,67:415-427.
    [48]赵建成,宋启军,王吉德.几种藓类植物挥发油的初步分析[J].河北师范大学学报(自然科学版),1998,22(2):254-256.
    [49]Saritas Y, Sonwa MM, Iznaguen H,et al. Volatile constituents in moss[J]. Phytochemistry,2001,57:443-457.
    [50]乔菲,马双成,林瑞超,等.暖地大叶藓挥发油成分的GC-MS分析[J].中国药学杂志,2004,39(9):704-705.
    [51]张文,娄红祥,李光耀,等.东亚绢藓化学成分研究[J].中草药,2002,33:581-583.
    [52]刘吉开,张开.网藓Syrrhopoden japonicus化学成分的研究[J].中山大学学报(自然科学版),1996,35:124-126.
    [53]王小宁,娄红祥.扁枝藓化学成分研究[J].中国药学杂志,2005,40(15):1131-1133.
    [54]Nagashima F. Terpenoids and aromatic compounds from the New Zealand liverworts Plagiochila, Schistochila, and Heteroscyphus species. Chem Pharm Bull,2004,52:556-560.
    [55]Bromley A K and M. Anderson. An electrophysiological study of olfaction in the aphid Nasonovia ribis-nigri[J].Ent. Exp. Appl.,1982, 32:101-110.
    [56]Blackman R L. Specificity in aphid-plant genetic interactions:with particular attention to the role of the alatecolonizer[J]. Campbell R. K. and Eikenbary, R.D.eds. Aphid-plant genotype interactions.1990, 251-274.
    [57]阚炜,张峰,张钟宁.一种影响蚜虫行为的植物挥发性此生化合物[J].科学通报,2001,46:1699-1702.
    [58]Pickett J. A., L. J. Wadhams, C. M. Woodcock, et al. The chemical ecology of aphids[J].Annu. Rev. Entomol.,1992,37:67-90.
    [59]周琼,梁广文.植物挥发性物质在蚜虫寄主定位中的作用[J].昆虫知识,2001,38(5):334-336.
    [60]Webster, B., T. Bruce, S. Dufour, C. Birkemeyer, M. Birkett, J. Hardie & J. Pickett. Dentification of volatile compounds used in host location by the black bean aphid, Aphis fabae[J]. Journal of Chemical Ecology, 2008,34:1153-1161.
    [61]Han, B.-Y.& Z.-M. Chen. Behavioral and electrophysiological responses of natural enemies to synomones from tea shoots and kairomones from tea aphids, Toxoptera aurantii[J].ournal of Chemical Ecology,2002,28(11):2203-2219.
    [62]Du, Y.-J., G. M. Poppy, W. Powell, J. A. Pickett, L. J. Wadhams & C. M. Woodcock. Identification of semiochemicals released during aphid feeding that attract parasitoid Aphidius ervi[J]. Journal of Chemical Ecology,1998,24(8):1355-1368.
    [63]Wang Y., Z. He, F. Ge & T.-G. Xiao. Chemical information interactions among host plants, Herbivorous insects and natural enemies[J]. Acta Agriculturae Jiangxi,2008,20(1):26-28.
    [64]陈胜,李明,季祥彪等.大金发藓化学成分的分离鉴定[J].山地农业生物学报,2008,27(3):279-282.
    [65]Song C. F., T. T. Zhu & R. H. Lu. Essential oil composition of Liverwort Lophozia ventricosa [J]. Chin J Appl Environ Biol,2007, 13 (4):458-460.
    [66]郑浩,杨长举,华红霞等.与昆虫有关的植物挥发性次生物质的研究方法[J].昆虫知识,2002,39(1):9-13.
    [67]温悦.挥发油提取方法研究概况[J].中国药业.2010,19(12):84-85.
    [68]Jirovetz, L., G. Buchbauer, P. M. Shafi, M. K. Rosammaet & M.Geissler. Analysis of the composition and aroma of the essential leaf oil of Syzygium travancoricum from South India by GC-FID, GC-MS, and olfactometry. Seasonal changes of composition[J]. Chromatographia Supplement,2001,53:372-373.
    [69]Lou, Y.-G.& J.-A. Chen. Herbivore-induced plant volatiles:primary characteristics, ecological functions and its release mechanism[J]. Acta Ecologica Sinica,2000,20(6):591-595.
    [70]Ping, L.-Y., Y.-B. Shen, Y.-J. Jin & J.-H. He. Leaf volatiles induced by mechanical damage from diverse taxonomic tree species[J]. Acta Botanica Sinica,2001,43(3):261-266.
    [71]Shen, Y.-B.& H.-B. Gao. Wounding signal transduction in interplant signal and perception[J]. Journal of Fu jian College of Forestry,2006, 26(1):92-96.
    [72]Dong, W.-X., F. Zhang, Y.-L. Fang & Z.-L. Zhang. Electroantennogram responses of aphid parasitoid Aphidius gifuensis to aphid pheromones and host-plant volatiles[J]. Chinese Journal of Ecology,2008,27(4):591-595.
    [73]李涛,张浩.GC-MS分析两种提取方法对川产大花红景天挥发油的影响[J].华西药学杂志,2010,25(4):389-391.
    [74]Wang, Q.& X. Luo. The application of bryophytes in plant prevention[J]. Gui Zhou Science,2001,4:93-100.
    [75]Anderson, W. H. Fatty acid composition as criterion in taxonomy of mosses[J]. Journal of the Hattori Botanical Laboratory,1974,38: 99-103.
    [76]娄红祥.苔藓植物化学与生物学[M].北京市:北京科学技术出版社,2005,8:21-22.
    [77]Toyota M, Asakawa Y. Volatile constituents of the liverwort Chiloscyphus pallidus(Mitt.)Engel&Schuster. Flacour and Fragrance Jouranl.1994,9:237-240.
    [78]Toyota M, koyama H, Asakawa Y. Volatile components of the liverworts Archilejeunea olivacea, Cheilolejeunea imbricate and Leptolejeunea elliptica. Phytochemistry,1997,44:1261-1264.
    [79]Toyota, M., K. Kimura & Y. Asakawa. Occurrence of ent-sesquiterpene in the Japanese moss-Plagiomnium acutum:first isolation and identification of the ent-sesqui-and dolabellane-type diterpenoids from the Musci[J]. Chemical & Pharmaceutical Bulletin, 1998,46:1488-1489.
    [80]Warmers, U & W. A. Koenig. Sesquiterpene constituents of the liverwort Bazzania trilobata[J]. Phytochemistry,1999,52:99-104.
    [81]Scher, J. M, J. B. Speakman & J. Zapp. Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.)S. F. Gray[J]. Phytochemistry,2004,65:2583-2588.
    [82]Toyota, M., E. Nakaishi & Y. Asakawa. Eudesmane-type sesquiterpenoids from the liverwort Lepidozia vitrea[J]. Phytochemistry,1996,41:833-836.
    [83]Nagashima, F., S. Takaoka, S. Huneck, Y. Asakawa & S. Takaoka. Sesqui-and diterpenoids from Ptilidium ciliare and Barbilophozia species (liverworts)[J]. Phytochemistry,1999,51:563-566.
    [84]Francis, F., G. Log nay & E. Haubruge.2004. Olfactory responses to aphid and host plant volatile releases:(E)-Farnesene an effective kairomone for the predator Adalia bipunctata[J]. Journal of Chemical Ecology,2004,4:741-755.
    [85]Micha, S.G.& U. Wyss. Aphid alarm pheromone (E)-β-farmese:a host finding kairomone for the aphid primary parasitoid Aphidius uzbekistanicus (Hymenoptera:Aphidiinae)[J]. Chemoecology,1996,7: 132-139.
    [86]Rostelien T, Borgkarlson AK, Mustaparta H. Selective receptor neurone responses to E-beta-ocimene, beta-myrcene, E,E-alpha-farnesene and homo-farnesene in the moth Heliothis virescens, identified by gas chromatography linked to electrophysiology[J].J Comp Physiol,2000,186(9):833-847.
    [87]Yi, Y.-J. The exploitation and utilization of Bryophyta resources[J]. Territory & Natural Resources Study,1999,3:73-75.
    [88]Du, Y.-J., F.-S. Yan, X.-L. Han & G.-X. Zhang. Olfaction in host plant selection of the soybean aphid Aphis glycines[J]. Acta Entomologica Sinica,1994,4:385-392.
    [89]Nottingham, S. F., J. Hardie, G. W. Dawson, A. J. Hick, J. A. Pickett, L. J. Wadhams & C. M. Woodcock. Behavioral and electrophysiological responses of aphids to host and nonhost plant volatiles[J]. Journal of Chemical Ecology,1991,17:1231-1242.
    [90]Yan, F.-S., Y. J.Du & X.-L.Han. A comparative study on the electroantenogram response of three aphid species to plant volatiles[J]. Entomologia Sinica,1994,1:53-66.
    [91]Gouinguene,S., J. A. Pickett, L. J. Wadhams, M. A. Birkett & T. C. J. Turlings. Antennal electrophysiological responses of three parasitic wasps to caterpillar-induced volatiles from maize (Zea mays mays), cotton (Gossypium herbaceum), and cowpea (Vigna unguiculata)[J]. Journal of Chemical Ecology,2005,5:1023-1038.
    [92]Hiltpold, I.& T. C. J. Turlings.2008. Belowground chemical signaling in maize:When simplicity rhymes with efficiency [J]. Journal of Chemical Ecology,2008,34:628-635.
    [93]Birkett, M. A., K. Chamberlain, J. A. Pickett, L. J. Wadhams & E. Guerrieri. Volatiles from whitefly-infested plants elicit a host-locating response in the parasitoid, Encarsia formosa[J].Journal of Chemical Ecology,2003,7:1589-1600.

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