基于SPME-GC/MS法研究干燥方式对迷迭香叶挥发性成分的影响

doi:10.3969/j.issn.1673-5854.2023.04.006

Abstract

Abstract:

Headspace solid-phase microextraction combined with gas chromatography-mass spectrometry was used to analyze and identify the volatile components of rosemary leaves and fresh rosemary leaves with five different drying treatments: natural drying, freeze drying, drying at 40, 60 and 80 ℃. The results showed that the main volatile components of dried rosemary leaves included terpinone, 4,6,6-trimethyl-bis[3.1.1] hept-3-ene-2-one, cineole, camphor, linalool, α-pinene, α-terpinol, bornyl acetate, pinocarvone, camphene and caryophyllene. Among them, the GC content of 4,6,6-trimethyl-bis[3.1.1] hept-3-ene-2-one and cineole reached 54.94%-60.09%. The main volatile components of rosemary leaves were alcohols, terpenes, aldehydes, alkanes, benzenes and esters. Freeze drying rosemary leaves had the most volatile components, with 44 identified, accounting for 99.61% of the total volatile substances. By analyzing the differences in the composition and content of volatile substances in rosemary leaves with five different drying methods, it was found that freeze drying could retain volatile components to the greatest extent.

Key words: headspace solid phase microextraction, gas chromatography-mass spectrometry, volatile components, rosemary

CLC Number:

TQ35

Pengfei GUO, Aihua ZHANG, Yinghui PENG, Hong WU, Desheng KANG, Zhihong XIAO. Effects of Drying Methods on Volatile Components of Rosemary Leaves Based on SPME-GC/MS Method[J]. Biomass Chemical Engineering, 2023, 57(4): 47-52.

Figures/Tables 3

Fig.1

Table 1

GC-MS identification results of volatile compounds in rosemary leaves under 5 drying treatments"

保留时间/min retaining time	化合物名称 compounds name	分子式 molecular fomula	GC含量 GC content /%
保留时间/min retaining time	化合物名称 compounds name	分子式 molecular fomula	F	ND	FD	HD-40	HD-60	HD-80
3.16/4.06	α-蒎烯 alpha-pinene	C₁₀H₁₆	22.22	1.52	1.75	0.86	0.59	1.60
4.39	2-甲基-5-(1-甲基乙基)-(1α, 2α, 5α)-双环[3.1.0]-3烯-2醇bicyclo[3.1.0]hex-3-en-2-ol, 2-methyl-5-(1-methylethyl)-, (1α, 2α, 5α)-	C₁₀H₁₆O	0.59	0.19	—	0.15	0.14	0.11
4.60	莰烯 camphene	C₁₀H₁₆	4.32	0.19	0.29	0.14	0.09	0.25
4.85	3-侧柏烯-2-醇 3-thujen-2-ol	C₁₀H₁₆O	—	0.21	0.28	0.15	0.10	0.15
5.36	2-甲基壬烷 nonane, 2-methyl-	C₁₀H₂₂	—	0.21	0.12	0.10	0.06	0.12
5.71	β-蒎烯 beta-pinene	C₁₀H₁₆	2.00	0.07	0.20	0.08	0.05	0.06
5.85	2,2,3,3,5,6,6-七甲基庚烷 heptane, 2,2,2,2,3,3,5,6,6-heptamethyl-	C₁₄H₃₀	*	0.10	—	—	—	—
6.01	β-月桂烯 beta-myrcene	C₁₀H₁₆	3.00	—	—	—	—	—
6.51	1,2,3-三甲基苯 benzene, 1,2,3-trimethyl-	C₉H₁₂	—	0.25	0.19	0.17	0.13	0.18
6.90	α-水芹烯 alpha-phellandrene	C₁₀H₁₆	0.19	—	0.09	0.05	0.07	0.05
7.27	对伞花烃 p-cymene	C₁₀H₁₄	6.04	—	—	—	—	—
7.39	1-甲基-4-(1-甲基乙基)-1,3-环己二烯 1,3-cyclohexadiene, 1-methyl-4-(1-methylethyl)-	C₁₀H₁₆	0.33	0.46	0.26	0.18	0.14	0.25
7.61	2,5-二甲基壬烷 nonane, 2,5-dimethyl-	C₁₁H₂₄	—	0.21	0.08	—	0.06	0.10
7.72	4-甲基癸烷 decane, 4-methyl-	C₁₁H₂₄	—	0.91	0.40	0.38	0.32	0.51
8.01	桉树醇 eucalyptol	C₁₀H₁₈O	31.33	24.96	24.31	20.26	19.12	18.76
8.69	γ-松油烯 gamma-terpinene	C₁₀H₁₆	0.72	—	—	—	—	—
8.95	3,3-二甲基己烷 hexane, 3,3-dimethyl-	C₈H₁₈	*	0.10	—	—	—	—
9.11	4-乙基癸烷 decane, 4-ethyl-	C₁₂H₂₆	—	0.07	0.64	0.11	0.20	0.07
9.12	4-甲基-3-庚酮 3-heptanone, 4-methyl-	C₈H₁₆O	—	0.54	1.00	0.77	*	0.64
9.12	5,7-二甲基十一烷 undecane, 5,7-dimethyl-	C₁₃H₂₈	—	1.73	—	—	—	—
9.32	十二烷 dodecane	C₁₂H₂₆	*	0.46	0.07	0.10	0.11	0.19
9.52	对薄荷-8-烯-1-醇 p-menth-8-en-1-ol	C₁₀H₁₈O	—	—	0.19	—	—	—
10.19	1,2-二甲基-4乙基-苯 benzene, 4-ethyl-1,2-dimethyl-	C₁₀H₁₄	—	0.14	*	*	*	*
10.27	1-甲基-3-(1-甲基乙基)-苯 benzene, 1-methyl-3-(1-methylethyl)-	C₁₀H₁₄	—	0.11	—	—	—	—
10.28	1-甲基-4-(1-甲基亚乙基)-环己烯 cyclohexene, 1-methyl-4-(1-methylethylidene)-	C₁₀H₁₆	—	—	0.11	0.10	*	*
10.44	2,3-二甲基环己基-1,3-二烯 2,3-dimethyl-cyclohexa-1,3-diene	C₈H₁₂	0.56	*	0.06	—	—	—
10.72	对甲基苯甲醇 benzenemethanol, 4-methyl-	C₈H₁₀O	0.75	—	—	—	—	—
10.92	芳樟醇1,6-octadien-3-ol, 3,7-dimethyl-	C₁₀H₁₈O	1.36	5.46	8.59	9.26	8.53	7.15
11.48	1,3,8-对薄荷三烯 1,3,8-p-menthatriene	C₁₀H₁₄	—	0.34	0.20	—	—	—
11.49	1,2,3,5-四甲基苯 benzene, 1,2,3,5-tetramethyl-	C₁₀H₁₄	*	0.55	*	0.21	0.29	0.31
11.73	5-(1,1-二甲基乙基)-1,3-环戊二烯 1,3-cyclopentadiene, 5-(1,1-dimethylethyl)-	C₉H₁₄	*	0.74	0.82	0.67	0.70	0.69
12.40	樟脑camphor	C₁₀H₁₆O	5.03	6.65	6.53	6.63	6.88	6.60
12.54	1,7,7-三甲基庚烷-双环[2.2.1]庚-2-酮 bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S)-	C₁₀H₁₆O	—	—	0.09	*	0.12	0.11
12.69	1-乙基-2,3-二甲基苯 benzene, 1-ethyl-2,3-dimethyl-	C₁₀H₁₄	—	0.12	—	0.05	*	0.07
13.02	3-松酮 trans-3-pinanone	C₁₀H₁₆O	0.55	0.62	0.62	0.80	0.87	0.11
13.11	松香芹酮 pinocarvone	C₁₀H₁₄O	—	1.14	1.11	1.20	1.30	1.47
13.25	(1,3-二甲基-2-亚甲基环戊基)-甲醇 (1,3-dimethyl-2-methylene-cyclopentyl)-methanol	C₉H₁₆O	*	0.54	0.55	0.50	*	0.48
13.41	乙酸丙烯酯 bornyl acetate	C₁₂H₂₀O₂	—	—	0.49	—	—	—
13.53	(1α, 2α, 5α)-2,6,6-三甲基-双环[3.1.1]庚-3-酮 bicyclo[3.1.1] heptan-3-one, 2,6,6-trimethyl-, (1 alpha, 2 alpha, 5 alpha)-	C₁₀H₁₆O	1.26	1.83	2.09	1.98	1.69	1.65
13.71	(R)-4-甲基-1-(1-甲基乙基)-3-环己烯-1-醇 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)-	C₁₀H₁₈O	*	1.36	2.57	2.04	1.78	1.69
14.35	α-松油醇 alpha-terpineol	C₁₀H₁₈O	0.40	3.07	3.97	3.73	3.91	3.58
14.74	异龙脑isoborneol	C₁₀H₁₈O	0.40	0.22	0.18	0.16	0.15	0.13
15.05	4,6,6-三甲基-双环[3.1.1]庚-3-烯-2-酮 bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-	C₁₀H₁₄O	5.03	35.13	31.40	34.68	37.32	37.85
15.12	1,3,3-三甲基-2-氧杂双环[2.2.2]辛-6-酮 2-oxabicyclo[2.2.2]octan-6-one, 1,3,3-trimethyl-	C₁₀H₁₆O₂	—	—	0.63	—	—	—
15.36	2-茨醇 endo-borneol	C₁₀H₁₈O	0.26	—	0.14	0.11	0.10	0.10
16.14	1,7,7-三甲基-双环[2.2.1]庚-2-醇 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol	C₁₀H₁₈O	—	0.10	—	0.22	0.20	0.19
16.53	4,6-二甲基十二烷 dodecane, 4,6-dimethyl-	C₁₄H₃₀	—	0.20	—	—	—	—
16.84	4,4-二甲基十一烷 undecane, 4,4-dimethyl-	C₁₃H₂₈	—	0.29	0.07	*	0.14	0.16
17.40	5-乙基-2-甲基辛烷 octane, 5-ethyl-2-methyl-	C₁₁H₂₄	—	0.46	0.31	0.25	0.25	0.24
17.59	乙酸龙脑酯 bornyl acetate	C₁₂H₂₀O₂	4.04	3.93	4.21	5.84	5.46	5.29
17.88	(Z)3,7-二甲基-2,6-辛二烯-1-醇 2,6-octadien-1-ol, 3,7-dimethyl-, (Z)-	C₁₀H₁₈O	*	0.19	0.07	0.14	0.20	0.25
17.97	β-月桂烯 beta-myrcene	C₁₀H₁₆	*	—	0.15	—	—	—
18.11	3,7-二甲基-2,6-辛二烯-1-醇 2,6-octadien-1-ol, 3,7-dimethyl-	C₁₀H₁₈O	—	—	0.12	0.08	0.10	0.25
18.38	香叶醇 geraniol	C₁₀H₁₈O	*	*	0.18	0.15	0.14	0.13
20.21	7-(1-甲基亚乙基)-双环[4.1.0]-庚烷 bicyclo[4.1.0]heptane, 7-(1-methylethylidene)-	C₁₀H₁₆	—	—	0.07	—	—	—
21.05	乙酸香叶酯 geranyl acetate	C₁₂H₂₀O₂	—	—	0.19	0.24	0.18	0.17
21.91	石竹烯 caryophyllene	C₁₅H₂₄	0.81	1.28	3.48	3.00	2.51	2.27
22.96	草烯 humulene	C₁₅H₂₄	0.09	0.16	0.43	0.37	0.32	0.29

Table 1

Table 2

References 16

1	COLER, 毕良武, 赵振东. 欧洲迷迭香的研究状况[J]. 生物质化学工程, 2006, 40 (2): 41- 44.
2	许鹏翔, 贾卫民, 毕良武, 等. 不同产地的迷迭香精油成分分析及品质研究[J]. 分析科学学报, 2003, (4): 361- 363.
3	张保顺, 袁吕江, 冯敏, 等. 迷迭香天然抗氧化剂的研究及其应用[J]. 江苏食品与发酵, 2006, (1): 20- 22.
4	中华人民共和国国家卫生和计划生育委员会. 食品安全国家标准食品添加剂迷迭香提取物: GB 1886.172—2016[S]. 北京: 中国标准出版社, 2017.
5	李玉邯. 天然香料迷迭香及其提取物开发应用的研究进展[J]. 中国调味品, 2017, 42 (12): 178- 180.
6	王强, 王玉荣, 陈世凡, 等. 迷迭香提取物对鲊广椒肉丸储藏过程中品质变化的影响[J]. 中国食品添加剂, 2020, 31 (3): 101- 107.
7	吴蒙, 徐晓军. 迷迭香化学成分及药理作用最新研究进展[J]. 生物质化学工程, 2016, 50 (3): 51- 57.
8	梁正敏. 迷迭香酸对哮喘小鼠气道炎症和氧化性肺损伤的影响及相关机制研究[D]. 南宁: 广西大学, 2017.
9	汪镇朝, 张海燕, 邓锦松, 等. 迷迭香的化学成分及其药理作用研究进展[J]. 中国实验方剂学杂志, 2019, 25 (24): 211- 218.
10	李大伟, 毕良武, 赵振东, 等. 迷迭香提取物检测方法研究进展[J]. 林产化学与工业, 2011, 31 (2): 119- 126.
11	李璇, 潘婷敏, 耿媛霄, 等. α-萜品烯酰基农用杀菌活性物的合成及活性研究[J]. 林产化学与工业, 2022, 42 (6): 39- 46.
12	宋述芹. 迷迭香挥发性成分GC/MS分析[J]. 赤峰学院学报(自然科学版), 2012, 28 (24): 6- 9.
13	JEMIA M B , TUNDIS R , PUGLIESE A , et al. Effect of bioclimatic area on the composition and bioactivity of Tunisian Rosmarinus officinalis essential oils[J]. Natural Product Research, 2015, 29 (3): 213- 222.
14	樊红日, 张立颖, 陈宝, 等. 广西巴马迷迭香精油化学成分分析[J]. 湖北农业科学, 2012, 51 (12): 2582- 2585.
15	熊俊君, 谢桂容, 代秀秀, 等. 迷迭香干燥前后挥发油化学成分GC-MS分析[J]. 食品工程, 2020, (4): 47- 51.
16	陈亮, 胡雅宁, 吴志明, 等. 迷迭香叶片干燥前后精油成分GC-MS分析[J]. 江苏农业科学, 2019, 47 (24): 171- 176.

干燥方式 drying method	烯萜 dilute terpene		醇 alcohol		醛酮 aldehyde and ketone		烷烃 alkanes		苯 benzene		酯 ester
干燥方式 drying method	种类/个 species	GC/%	种类/个 species	GC/%	种类/个 species	GC/%	种类/个 speices	GC/%	种类/个 species	GC/%	种类/个 species	GC/%
F	11	39.27	7	35.09	3	6.84	0	0	1	6.04	1	4.04
ND	9	11.41	10	36.30	4	39.26	10	4.74	5	1.17	1	3.93
FD	12	14.37	12	41.15	6	36.94	9	1.86	2	0.22	3	4.79
HD-40	10	12.08	12	36.80	6	39.43	5	0.94	3	0.43	2	6.08
HD-60	9	11.35	13	34.13	5	41.30	6	1.46	2	0.42	2	5.64
HD-80	9	12.06	13	32.97	6	41.83	7	1.39	3	0.56	2	5.46

[1]	GAO Xinyan, WANG Haiying, LIU Zhiming, DUAN Xiaoling, FENG Xinhui. Analysis of Volatile Components and Antibacterial Activity of Lonicera maackii(Rupr.) Maxim. Extracts [J]. bce, 2018, 52(1): 10-16.
[2]	WU Meng, XU Xiao-jun. New Progress on Chemical Composition and Pharmacological Effects of Rosmarinus officinalis L. [J]. bce, 2016, 50(3): 51-57.
[3]	LIU Zhi-ming;WANG Hai-ying;WANG Fang;PAN Xiao-xing;TIAN Bu. Antibacterial Activity Analysis of Essential Oil from Chamaecyparis pisifera Heartwood [J]. , 2011, 45(4): 27-31.
[4]	LIU Zhi-ming;REN Hai-qing;WANG Fang;TIAN Bu;PAN Xiao-xing. Comparison of Chemical Composition of Essential Oils of Phyllostachys heterocycla 'Pubescens' and Chamaecyparis pisifera [J]. , 2011, 45(3): 31-34.
[5]	BI Liang-wu;LI Da-wei;ZHAO Zhen-dong;LI Dong-mei. Review on Development and Comprehensive Utilization of Rosemary Resources [J]. , 2011, 45(3): 53-56.
[6]	LIU Zhi- ming;WANG Hai-ying;LIU Shan-shan;JIANG Nai-xiang;LI Ling. Analysis of Active Components of Essential Oil from Conyza canadensis [J]. , 2010, 44(1): 22-26.
[7]	GAO Hong;SONG Zhan-qian;YE Bo-hui;SHANG Shi-bin. Analysis of Chemical Components of Pinus elliottii Engelm. Oleoresin from Brazil [J]. , 2007, 41(5): 18-20.
[8]	Rosemary Cole;BI Liang-wu;ZHAO Zhen-dong. Research Progress of Rosemary in Europe [J]. , 2006, 40(2): 41-44.

Effects of Drying Methods on Volatile Components of Rosemary Leaves Based on SPME-GC/MS Method

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 3

References 16

Related Articles 8

Recommended Articles

Metrics

Comments