Extraction， Component Identification and Fumigant Activity of Lemongrass Essential Oil Against Red Imported Fire Ants

doi:10.13304/j.nykjdb.2024.0697

Abstract

Abstract:

To investigate the fumigant activity of Cymbopogon citratus （lemongrass） essential oil （EO） on Solenopsis invicta （red imported fire ants， RIFA）， the lemongrass essential oil was extracted and purified using hydrodistillation and column chromatography. Gas chromatography-mass spectrometry （GC-MS） was applied to analyze and identify the chemical components of lemongrass essential oil and its different fractions. Then fumigant activities of different fractions in EO and monomers against RIFA were determined. The results showed that the light yellow lemongrass EO was extracted by water distillation with the rate of 1.02%. The fumigant activity of lemongrass EO against RIFA increased as the increase of treatment dosage. At 400 μL·L^-1， the LT₅₀ （lethal time of 50%） was 0.197 h with obvious sublethal effect. 2 fractions A1 and A2 from lemongrass EO were obtained by column chromatography. GS-MS analysis showed that the dominant component of lemongrass EO and A1 fractions was citronellal with the relative contents of 24.72% and 31.75%， respectively， and geranol was the main component of A2 fraction with the relative contents of 23.54%. Under the same dosage treatment， the fumigation activity of A1 fraction was highest， and the lemongrass EO was second. After treatment with 25.0 and 12.5 μL·L^-1 for 0.5 and 1.0 h， both citronellal and D-limonene showed 100% fumigant activity against RIFA， indicating that citronellal and D-limonene were the main active substances. Above results provided new ideas for the prevention and control of RIFA.

Key words: lemongrass, red imported fire ants, essential oil, component identification, fumigant activity

摘要：

为探究柠檬草精油对红火蚁的熏蒸活性，通过水蒸馏提取法+柱层析法对柠檬草精油进行提取和纯化，应用气相色谱仪-质谱联用仪（gas chromatography-mass spectrometry，GC-MS）对柠檬草精油及其不同馏分化学成分进行分析和鉴定，分别测定精油不同馏分及单体对红火蚁的熏蒸活性。结果表明，在100 ℃下，采用水蒸馏提取法提取2.0 h后从柠檬草中提取出了淡黄色柠檬草精油，提取率为1.02%。生测结果表明，柠檬草精油对红火蚁的熏蒸活性随着处理剂量的增加而增加，在400 μL·L^-1时，LT₅₀（lethal time of 50%）最小为0.197 h，且存在明显的亚致死效应。用柱层析法获得2个柠檬草精油馏分A1、A2。GC-MS分析发现，柠檬草精油和A1馏分中相对含量最高的成分均为香茅醛，分别为24.72%和31.75%；A2馏分的主要成分为香叶醇，其相对含量为23.54%。在相同剂量处理下，A1馏分的熏蒸活性最高，柠檬草精油次之。采用25.0和12.5 μL·L^-1分别处理0.5和1.0 h后，香茅醛和D-柠檬烯对红火蚁的熏蒸活性均为100%，表明香茅醛、D-柠檬烯为主要活性物质。以上研究结果为防治红火蚁提供新的思路。

关键词: 柠檬草, 红火蚁, 精油, 成分鉴定, 熏蒸活性

CLC Number:

S436.6

Fan KUANG, Mingkun XIAO, Yuhan HUANG, Hongmin JIANG, Lei HU, Ying WEI, Wei HU. Extraction， Component Identification and Fumigant Activity of Lemongrass Essential Oil Against Red Imported Fire Ants[J]. Journal of Agricultural Science and Technology, 2025, 27(9): 155-164.

邝凡, 肖明昆, 黄钰涵, 江洪敏, 胡磊, 魏英, 胡威. 柠檬草精油的提取、成分鉴定及对红火蚁的熏蒸活性研究[J]. 中国农业科技导报, 2025, 27(9): 155-164.

Figures/Tables 9

References 34

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序号 NO.	保留时间 Retain time/min	化合物名称 Compound name	化学分子式Chemical formula	相对分子量 Relative molecular mass	相对含量 Relative content/%
1	9.518	D-柠檬烯D-limonene	C₁₀H₁₆	136.24	5.34
2	10.926	丁酸芳樟酯1，5-dimethyl-1-vinyl-4-hexenyl butyrate	C₁₄H₂₄O₂	224.35	1.35
3	12.047	香茅醛 Citronellal	C₁₀H₁₈O	154.24	24.72
4	13.278	3，7-二甲基辛烯醇3，7-dimethyl-2-octen-1-ol	C₁₀H₂₀O	156.26	12.76
5	13.793	香叶醇Geraniol	C₁₀H₁₈O	154.25	15.06
6	14.874	—	—	—	3.24
7	15.080	丁香酚 Eugenol	C₁₀H₁₂O₂	164.20	2.54
8	15.303	牛儿酸乙酯（E）-3，7-dimethylocta-2，6-dienyl ethyl carbonate	C₁₂H₂₀O₂	196.29	2.88
9	15.469	1-乙烯基-1-甲基-2，4-双（1-甲基乙烯基）-环己烷1-ethenyl-1-methyl-2，4-bis（1-methylethenyl）-，［1S-（1.alpha.，2.beta.，4.beta.）］-cyclohexane	C₁₅H₂₄	204.35	3.33
10	16.562	丙位依兰烯Gamma.-muurolene	C₁₅H₂₄	204.35	0.94
11	16.676	毕澄茄烯［1，3］cyclopropa［1‑2］benzene， octahydro-7-methyl-3-methylene-4-（1-methylethyl）-，［3aS-（3a.alpha.，3b.beta.，4.beta.，7.alpha.，7aS*）］-1h-cyclopenta	C₁₅H₂₄	204.35	4.33
12	16.779	二环［4.4.0］癸-1-烯，2-异丙基-5-甲基-9-亚甲基Bicyclo［4.4.0］dec-1-ene， 2-isopropyl-5-methyl-9-methylene	C₁₅H₂₄	204.35	0.33
13	16.848	α-衣兰油烯Alpha.-Muurolene	C₁₅H₂₄	204.35	2.12
14	17.037	1，2，3，4，4a，5，6，8a-八氢-7-甲基-4-亚甲基-1-（1-甲基乙基）-萘- 1，2，3，4，4a，5，6，8a-octahydro-7-methyl-4-methylene-1-（1-methylethyl）-，（1.alpha.，4a.beta.，8a.alpha.）-naphthalene	C₁₅H₂₄	204.35	1.36
15	17.163	（+）-delta-杜松烯1，2，3，5，6，8a-hexahydro-4，7-dimethyl-1-（1-methylethyl）-，（1S-cis）-naphthalene	C₁₅H₂₄	204.35	4.12
16	17.535	欖醇4-ethenyl-.alpha.，.alpha.，4-trimethyl-3-（1-methylethenyl）-，［1R-（1.alpha.，3.alpha.，4.beta.）］-cyclohexanemethanol	C₁₅H₂₆O	222.37	6.41
17	17.821	1-羟基-1，7二甲基-4-异丙基-2，7-环癸二烯1-hydroxy-1， 7-dimethyl-4-isopropyl-2，7-cyclodecadiene	C₁₅H₂₆O	222.37	1.14
18	18.467	γ-桉叶醇1，2，3，4，4a，5，6，7-octahydro-.alpha.，.alpha.， 4a，8-tetramethyl-，（2R-cis）-2-naphthalenemethanol	C₁₅H₂₆O	222.37	5.15
19	18.588	α-毕橙茄醇Tau.-cadinol	C₁₅H₂₆O	222.37	2.49
20	22.267	反式-香叶基香叶醇Trans-geranylgeranio	C₁₀H₁₈O	154.25	0.39

序号 NO.	保留时间 Retain time/min	化合物名称 Compound name	化学分子式Chemical formula	相对分子量 Relative molecular mass	相对含量 Relative content/%
1	9.518	D-柠檬烯D-limonene	C₁₀H₁₆	136.24	5.34
2	10.926	丁酸芳樟酯1，5-dimethyl-1-vinyl-4-hexenyl butyrate	C₁₄H₂₄O₂	224.35	1.35
3	12.047	香茅醛 Citronellal	C₁₀H₁₈O	154.24	24.72
4	13.278	3，7-二甲基辛烯醇3，7-dimethyl-2-octen-1-ol	C₁₀H₂₀O	156.26	12.76
5	13.793	香叶醇Geraniol	C₁₀H₁₈O	154.25	15.06
6	14.874	—	—	—	3.24
7	15.080	丁香酚 Eugenol	C₁₀H₁₂O₂	164.20	2.54
8	15.303	牛儿酸乙酯（E）-3，7-dimethylocta-2，6-dienyl ethyl carbonate	C₁₂H₂₀O₂	196.29	2.88
9	15.469	1-乙烯基-1-甲基-2，4-双（1-甲基乙烯基）-环己烷1-ethenyl-1-methyl-2，4-bis（1-methylethenyl）-，［1S-（1.alpha.，2.beta.，4.beta.）］-cyclohexane	C₁₅H₂₄	204.35	3.33
10	16.562	丙位依兰烯Gamma.-muurolene	C₁₅H₂₄	204.35	0.94
11	16.676	毕澄茄烯［1，3］cyclopropa［1‑2］benzene， octahydro-7-methyl-3-methylene-4-（1-methylethyl）-，［3aS-（3a.alpha.，3b.beta.，4.beta.，7.alpha.，7aS*）］-1h-cyclopenta	C₁₅H₂₄	204.35	4.33
12	16.779	二环［4.4.0］癸-1-烯，2-异丙基-5-甲基-9-亚甲基Bicyclo［4.4.0］dec-1-ene， 2-isopropyl-5-methyl-9-methylene	C₁₅H₂₄	204.35	0.33
13	16.848	α-衣兰油烯Alpha.-Muurolene	C₁₅H₂₄	204.35	2.12
14	17.037	1，2，3，4，4a，5，6，8a-八氢-7-甲基-4-亚甲基-1-（1-甲基乙基）-萘- 1，2，3，4，4a，5，6，8a-octahydro-7-methyl-4-methylene-1-（1-methylethyl）-，（1.alpha.，4a.beta.，8a.alpha.）-naphthalene	C₁₅H₂₄	204.35	1.36
15	17.163	（+）-delta-杜松烯1，2，3，5，6，8a-hexahydro-4，7-dimethyl-1-（1-methylethyl）-，（1S-cis）-naphthalene	C₁₅H₂₄	204.35	4.12
16	17.535	欖醇4-ethenyl-.alpha.，.alpha.，4-trimethyl-3-（1-methylethenyl）-，［1R-（1.alpha.，3.alpha.，4.beta.）］-cyclohexanemethanol	C₁₅H₂₆O	222.37	6.41
17	17.821	1-羟基-1，7二甲基-4-异丙基-2，7-环癸二烯1-hydroxy-1， 7-dimethyl-4-isopropyl-2，7-cyclodecadiene	C₁₅H₂₆O	222.37	1.14
18	18.467	γ-桉叶醇1，2，3，4，4a，5，6，7-octahydro-.alpha.，.alpha.， 4a，8-tetramethyl-，（2R-cis）-2-naphthalenemethanol	C₁₅H₂₆O	222.37	5.15
19	18.588	α-毕橙茄醇Tau.-cadinol	C₁₅H₂₆O	222.37	2.49
20	22.267	反式-香叶基香叶醇Trans-geranylgeranio	C₁₀H₁₈O	154.25	0.39

序号 No.	保留时间 Retain Time/min	化合物名称 Compound name	化学分子式Chemical formula	相对分子量Relative molecular mass	相对含量 Relative content/%
1	5.181	1-甲基-3-异丙基环戊烷1-methyl-3-（1-methylethyl）-cyclopentane	C₉H₁₈	126.34	1.64
2	9.570	D-柠檬烯D-limonene	C₁₀H₁₆	136.24	11.02
3	9.999	2，6-二甲基-5-庚烯醛2，6-dimethyl-5-heptenal	C₉H₁₆O	140.22	0.74
4	12.036	香茅醛Citronellal	C₁₀H₁₈O	154.25	31.75
5	12.929	1，2-二乙基-3-甲基-环己烷1，2-diethyl-3-methyl-cyclohexane	C₁₁H₂₂	154.25	3.04
6	13.564	2-甲基-6-亚甲基-2-辛醇2-methyl-6-methylene-2-octanol	C₁₀H₂₀O	154.25	5.19
7	14.886	乙酸香茅酯6-octen-1-ol，3，7-dimethyl-， acetate	C₁₂H₂₂O₂	198.30	9.09
8	15.326	牛儿酸乙酯（E）-3，7-dimethylocta-2，6-dienyl ethyl carbonate	C₁₂H₂₀O₂	196.29	4.56
9	15.509	β-榄香烯1-ethenyl-1-methyl-2，4-bis（1-methylethenyl）-，［1S-（1.alpha.，2.beta.，4.beta.）］-cyclohexane	C₁₅H₂₄	204.35	7.23
10	16.270	欖醇Cyclohexanemethanol，4-ethenyl-.alpha.，.alpha.，4-trimethyl-3-（1-methylethenyl）-，［1R-（1.alpha.，3.alpha.，4.beta.）］	C₁₅H₂₆O	222.36	0.65
11	16.551	γ-依兰油烯Gamma.-muurolene	C₁₅H₂₄	204.35	1.73
12	16.636	β-古巴烯Beta-copaene	C₁₅H₂₄	204.35	1.93
13	16.705	γ-古芸烯1，2，3，3a，4，5，6，7-octahydro-1，4-dimethyl-7-（1-methylethenyl）-，（1R，3aR，4R，7R）-azulene	C₁₅H₂₄	204.35	0.46
14	16.860	α-依兰油烯α-muurolene	C₁₅H₂₄	204.35	4.19
15	17.060	杜松烯1，2，3，4，4a，5，6，8a-octahydro-7-methyl-4-methylene-1-（1-methylethyl）-，（1.alpha.，4a.beta.，8a.alpha.）-naphthalene	C₁₅H₂₄	204.35	3.07
16	17.192	δ-杜松烯1，2，3，5，6，8a-hexahydro-4，7-dimethyl-1-（1-methylethyl）-，（1S-cis）-naphthalene	C₁₅H₂₄	204.35	6.75
17	17.718	—	—	—	1.11
18	18.170	金合欢醇3，7，11-trimethyl-2，6，10-dodecatrien-1-ol	C₁₅H₂₆O	222.37	0.77
19	18.736	—	—	—	1.69
20	19.326	反式-长叶松香芹醇Trans-longipinocarveol	C₁₅H₂₄O	222.37	0.75
21	19.852	—	—	—	0.86
22	20.590	—	—	—	0.80
23	22.284	反式-香叶基香叶醇Trans-geranylgeraniol	C₂₀H₃₄O	290.48	0.98

序号 No.	保留时间 Retain Time/min	化合物名称 Compound name	化学分子式Chemical formula	相对分子量Relative molecular mass	相对含量 Relative content/%
1	5.181	1-甲基-3-异丙基环戊烷1-methyl-3-（1-methylethyl）-cyclopentane	C₉H₁₈	126.34	1.64
2	9.570	D-柠檬烯D-limonene	C₁₀H₁₆	136.24	11.02
3	9.999	2，6-二甲基-5-庚烯醛2，6-dimethyl-5-heptenal	C₉H₁₆O	140.22	0.74
4	12.036	香茅醛Citronellal	C₁₀H₁₈O	154.25	31.75
5	12.929	1，2-二乙基-3-甲基-环己烷1，2-diethyl-3-methyl-cyclohexane	C₁₁H₂₂	154.25	3.04
6	13.564	2-甲基-6-亚甲基-2-辛醇2-methyl-6-methylene-2-octanol	C₁₀H₂₀O	154.25	5.19
7	14.886	乙酸香茅酯6-octen-1-ol，3，7-dimethyl-， acetate	C₁₂H₂₂O₂	198.30	9.09
8	15.326	牛儿酸乙酯（E）-3，7-dimethylocta-2，6-dienyl ethyl carbonate	C₁₂H₂₀O₂	196.29	4.56
9	15.509	β-榄香烯1-ethenyl-1-methyl-2，4-bis（1-methylethenyl）-，［1S-（1.alpha.，2.beta.，4.beta.）］-cyclohexane	C₁₅H₂₄	204.35	7.23
10	16.270	欖醇Cyclohexanemethanol，4-ethenyl-.alpha.，.alpha.，4-trimethyl-3-（1-methylethenyl）-，［1R-（1.alpha.，3.alpha.，4.beta.）］	C₁₅H₂₆O	222.36	0.65
11	16.551	γ-依兰油烯Gamma.-muurolene	C₁₅H₂₄	204.35	1.73
12	16.636	β-古巴烯Beta-copaene	C₁₅H₂₄	204.35	1.93
13	16.705	γ-古芸烯1，2，3，3a，4，5，6，7-octahydro-1，4-dimethyl-7-（1-methylethenyl）-，（1R，3aR，4R，7R）-azulene	C₁₅H₂₄	204.35	0.46
14	16.860	α-依兰油烯α-muurolene	C₁₅H₂₄	204.35	4.19
15	17.060	杜松烯1，2，3，4，4a，5，6，8a-octahydro-7-methyl-4-methylene-1-（1-methylethyl）-，（1.alpha.，4a.beta.，8a.alpha.）-naphthalene	C₁₅H₂₄	204.35	3.07
16	17.192	δ-杜松烯1，2，3，5，6，8a-hexahydro-4，7-dimethyl-1-（1-methylethyl）-，（1S-cis）-naphthalene	C₁₅H₂₄	204.35	6.75
17	17.718	—	—	—	1.11
18	18.170	金合欢醇3，7，11-trimethyl-2，6，10-dodecatrien-1-ol	C₁₅H₂₆O	222.37	0.77
19	18.736	—	—	—	1.69
20	19.326	反式-长叶松香芹醇Trans-longipinocarveol	C₁₅H₂₄O	222.37	0.75
21	19.852	—	—	—	0.86
22	20.590	—	—	—	0.80
23	22.284	反式-香叶基香叶醇Trans-geranylgeraniol	C₂₀H₃₄O	290.48	0.98

序号 NO.	保留时间 Retain Time/min	化合物名称 Compound name	化学分子式Chemical formula	相对分子量 Relative molecular mass	相对含量 Relative content/%
1	10.937	丁酸芳樟醇脂1，5-dimethyl-1-vinyl-4-hexenyl butyrate	C₁₄H₂₄O₂	224.34	3.20
2	11.801	（+）-异胡薄荷醇D-isopulegol	C₁₀H₁₈O	154.14	9.68
3	13.283	3，7-二甲基-2-辛烯-1-醇3，7-dimethyl-2-octen-1-ol	C₁₀H₂₀O	156.15	23.53
4	13.787	香叶醇Geraniol	C₁₀H₁₈O	154.25	23.54
5	15.080	丁香酚Eugenol	C₁₀H₁₂O₂	164.20	5.70
6	17.048	3，5-二叔丁基苯酚3，5-bis（1，1-dimethylethyl）-phenol	C₁₄H₂₂O	206.32	0.78
7	17.569	榄醇4-ethenyl-.alpha.，.alpha.，4-trimethyl-3-（1-methylethenyl）-，［1R-（1.alpha.，3.alpha.，4.beta.）］-cyclohexanemethanol	C₁₅H₂₆O	222.37	14.26
8	18.490	γ-桉叶烯Decahydro-4a-methyl-1-methylene-7-（1-methylethylidene）-，（4aR-trans）-naphthalene	C₁₅H₂₄	204.35	3.93
9	18.599	T-荜澄茄醇T-cadinol	C₁₅H₂₆O	222.37	5.10
10	18.805	表桉叶油醇1，2，3，4，4a，5，6，7-octahydro-α，α，4a，8-tetramethyl-，（2R，4aS）-2-naphthalenemethanol	C₁₅H₂₆O	222.37	10.27