Essential Oil Preparation and Volatile Components Analysis in Acanthopanax senticosus Leaves

doi:10.11924/j.issn.1000-6850.casb2023-0777

Abstract

Abstract:

In order to compare the yield of essential oil from Acanthopanax senticosus leaves prepared by different extraction methods and to analyze its quality, Acanthopanax senticosus leaves were used as raw materials, essential oils were prepared using both steam distillation and supercritical CO₂ extraction methods, followed by the analysis of volatile components using GC-MS. Additionally, the prepared oils were analyzed for their antibacterial and antioxidant activities. The yield of essential oil obtained by steam distillation was 0.10%, whereas the yield obtained by supercritical CO₂ extraction was 0.47%. GC-MS analysis identified 35 components out of 57 separated from the essential oil prepared by steam distillation, and 57 components out of 94 separated from the oil prepared by supercritical CO₂ extraction. Antibacterial tests indicated that Acanthopanax senticosus leaf essential oil possessed certain antibacterial activity. Moreover, the essential oil exhibited good antioxidant activity, with a DPPH radical scavenging rate of 30.7% and an IC₅₀ value of 3.510±0.175 μg/mL. The results suggest that Acanthopanax senticosus leaf essential oil contains a variety of aromatic compounds that not only contribute to the oil's fragrance but also possess multiple active properties, providing a reference for the rational use of Acanthopanax senticosus leaves and the preparation of essential oils.

Key words: Acanthopanax senticosus leaves, supercritical CO₂ extraction, essential oil, GC-MS, steam distillation, antibacterial activity, antioxidant activity

LI Wanru, GUAN Xin, QI Kexiang, ZHANG He, ZENG Weimin, ZHENG Chunying. Essential Oil Preparation and Volatile Components Analysis in Acanthopanax senticosus Leaves[J]. Chinese Agricultural Science Bulletin, 2024, 40(18): 157-164.

Figures/Tables 7

References 26

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供试菌种类	供试菌名称
供试细菌	大肠杆菌(Escherichia coli) 金黄色葡萄球菌(Staphylococcus aureus) 单增李斯特菌(Listeria monocytogenes) 铜绿假单胞菌(Pseudomonas aeruginosa)
供试真菌	白假丝酵母(Candida albicans)

供试菌种类	供试菌名称
供试细菌	大肠杆菌(Escherichia coli) 金黄色葡萄球菌(Staphylococcus aureus) 单增李斯特菌(Listeria monocytogenes) 铜绿假单胞菌(Pseudomonas aeruginosa)
供试真菌	白假丝酵母(Candida albicans)

序号	保留时间/min	分子式	化合物名称	相对含量/%
1	6.32	C₆H₁₂O	顺-3-己烯-1-醇	3.17
2	7.01	C₆H₁₂O	4-戊醇-3-甲基	1.04
3	7.47	C₅H₈O₃	1,2-环氧-3-乙酸丙酯	0.11
4	16.29	C₁₀H₁₆O	1,3,4-三甲基-3-环己烯-1-醛	0.06
5	18.85	C₁₀H₁₄	4-异丙基甲苯	0.12
6	21.80	C₉H₁₆O	反式-2-壬烯醛	0.32
7	24.21	C₁₀H₂₀O	薄荷脑	0.09
8	24.85	C₁₁H₂₀O₂	氧杂环十二烷-2-酮	0.09
9	27.01	C₁₀H₁₈O	冰片	0.16
10	28.17	C₁₀H₂₀O	L-薄荷醇	0.06
11	29.01	C₁₁H₁₂	1-亚甲基丁-2-烯基苯	0.13
12	30.09	C₁₂H₃₄O₅Si₄	1,1,3,3,5,5,7,7-八甲基四硅氧烷	0.11
13	31.34	C₁₅H₂₄	4-乙烯基-4-甲基-3-(1-甲基乙烯基)-1-(1-甲基乙基)-环己烯-3R-反式环己烯	2.49
14	32.68	C₁₅H₂₆O	α-红没药醇	8.63
15	32.89	C₁₅H₂₄	环己烷，1-乙烯基-1-甲基-2,4-双(1-甲基烯基)-	1.68
16	33.71	C₁₅H₂₄	石竹烯	9.13
17	34.66	C₁₅H₂₄	δ-榄香烯	11.45
18	35.33	C₁₅H₂₄	γ-蓓草烯	0.58
19	36.00	C₁₆H₂₆O₂	3，7，11-三甲基-1，6，10-十二碳三烯-3-甲酸酯	1.28
20	36.95	C₁₅H₂₂O	6-(1，3-二甲基丁-1，3-二烯基)-1，5，5-三甲基-7-氧杂双环[4.1.0]庚-2-烯	0.14
21	37.49	C₁₅H₂₄O₂	双环[4.4.0]癸-2-烯-4-醇，2-甲基-9-丙烯-3-醇-2-基	3.63
22	37.93	C₁₅H₂₄O	氧化石竹烯	0.73
23	38.71	C₁₅H₂₄O₂	双环[4.4.0]癸-5-烯，1，5-二甲基-3-羟基-8-1-甲基烯-2-羟乙基-1)	0.64
24	39.30	C₁₅H₂₄O	(＋)-匙叶桉油烯醇	2.72
25	40.04	C₁₆H₂₀O₄	5-苯并呋喃乙酸，6-乙烯基-2，4，5，6，7，7a-六氢-3，6-二甲基亚甲基-2-氧代，甲酯	0.56
26	40.43	C₁₅H₂₀	4，5，9，10-脱氢异长叶烯	1.94
27	42.62	C₁₅H₂₂O₂	α-香附酮	0.76
28	46.37	C₁₅H₂₂O₂	诺卡酮-11，12-环氧化物	3.43
29	47.33	C₁₆H₂₆O₂	醋酸1，2，3，4，5，6，7，8-八氢-3，8，8-三甲基萘-2-基)甲酯	2.58
30	47.71	C₁₅H₂₂O₂	6-(1-羟甲基乙烯基)-4，8a-二甲基-3，5，6，7，8，8，8a-六氢-1H-2-萘酮	1.59
31	48.87	C₁₉H₂₆O₆	2-甲基丙酸，(十二氢-6a-羟基-9a-甲基)L-3-亚甲基-2，9-二氧代芜[4，5-b]呋喃-6-基)甲酯	2.76
32	50.00	C₁₅H₂₂O₂	2aS，3aR，5aS，9bR)-2a，5a，9-三甲基-2a，4，5，5a，6，7，8，9b-八氢-2H-萘并[1，2-b]环氧并 [2，3-c]呋喃	3.39
33	51.07	C₁₅H₂₄O₃	螺旋[4.4.0.0(5，9)]癸烷-10，2'-环氧乙烷]，1-甲基-4-异丙基-7，8-二羟基-(8S)-	1.36
34	51.87	C₁₅H₂₂O₂	6-(1-羟甲基乙烯基)-4，8a-二甲基-3，5，6，7，8，8a-六氢-1Hin-2-萘酮	3.48
35	58.10	C₂₃H₃₂O	2-[4-甲基-6-(2，6，6-三甲基环己基-1-烯基)六-1，3，5-三烯基]环己基-1-烯-1-甲醛	0.16

序号	保留时间/min	分子式	化合物名称	相对含量/%
1	6.32	C₆H₁₂O	顺-3-己烯-1-醇	3.17
2	7.01	C₆H₁₂O	4-戊醇-3-甲基	1.04
3	7.47	C₅H₈O₃	1,2-环氧-3-乙酸丙酯	0.11
4	16.29	C₁₀H₁₆O	1,3,4-三甲基-3-环己烯-1-醛	0.06
5	18.85	C₁₀H₁₄	4-异丙基甲苯	0.12
6	21.80	C₉H₁₆O	反式-2-壬烯醛	0.32
7	24.21	C₁₀H₂₀O	薄荷脑	0.09
8	24.85	C₁₁H₂₀O₂	氧杂环十二烷-2-酮	0.09
9	27.01	C₁₀H₁₈O	冰片	0.16
10	28.17	C₁₀H₂₀O	L-薄荷醇	0.06
11	29.01	C₁₁H₁₂	1-亚甲基丁-2-烯基苯	0.13
12	30.09	C₁₂H₃₄O₅Si₄	1,1,3,3,5,5,7,7-八甲基四硅氧烷	0.11
13	31.34	C₁₅H₂₄	4-乙烯基-4-甲基-3-(1-甲基乙烯基)-1-(1-甲基乙基)-环己烯-3R-反式环己烯	2.49
14	32.68	C₁₅H₂₆O	α-红没药醇	8.63
15	32.89	C₁₅H₂₄	环己烷，1-乙烯基-1-甲基-2,4-双(1-甲基烯基)-	1.68
16	33.71	C₁₅H₂₄	石竹烯	9.13
17	34.66	C₁₅H₂₄	δ-榄香烯	11.45
18	35.33	C₁₅H₂₄	γ-蓓草烯	0.58
19	36.00	C₁₆H₂₆O₂	3，7，11-三甲基-1，6，10-十二碳三烯-3-甲酸酯	1.28
20	36.95	C₁₅H₂₂O	6-(1，3-二甲基丁-1，3-二烯基)-1，5，5-三甲基-7-氧杂双环[4.1.0]庚-2-烯	0.14
21	37.49	C₁₅H₂₄O₂	双环[4.4.0]癸-2-烯-4-醇，2-甲基-9-丙烯-3-醇-2-基	3.63
22	37.93	C₁₅H₂₄O	氧化石竹烯	0.73
23	38.71	C₁₅H₂₄O₂	双环[4.4.0]癸-5-烯，1，5-二甲基-3-羟基-8-1-甲基烯-2-羟乙基-1)	0.64
24	39.30	C₁₅H₂₄O	(＋)-匙叶桉油烯醇	2.72
25	40.04	C₁₆H₂₀O₄	5-苯并呋喃乙酸，6-乙烯基-2，4，5，6，7，7a-六氢-3，6-二甲基亚甲基-2-氧代，甲酯	0.56
26	40.43	C₁₅H₂₀	4，5，9，10-脱氢异长叶烯	1.94
27	42.62	C₁₅H₂₂O₂	α-香附酮	0.76
28	46.37	C₁₅H₂₂O₂	诺卡酮-11，12-环氧化物	3.43
29	47.33	C₁₆H₂₆O₂	醋酸1，2，3，4，5，6，7，8-八氢-3，8，8-三甲基萘-2-基)甲酯	2.58
30	47.71	C₁₅H₂₂O₂	6-(1-羟甲基乙烯基)-4，8a-二甲基-3，5，6，7，8，8，8a-六氢-1H-2-萘酮	1.59
31	48.87	C₁₉H₂₆O₆	2-甲基丙酸，(十二氢-6a-羟基-9a-甲基)L-3-亚甲基-2，9-二氧代芜[4，5-b]呋喃-6-基)甲酯	2.76
32	50.00	C₁₅H₂₂O₂	2aS，3aR，5aS，9bR)-2a，5a，9-三甲基-2a，4，5，5a，6，7，8，9b-八氢-2H-萘并[1，2-b]环氧并 [2，3-c]呋喃	3.39
33	51.07	C₁₅H₂₄O₃	螺旋[4.4.0.0(5，9)]癸烷-10，2'-环氧乙烷]，1-甲基-4-异丙基-7，8-二羟基-(8S)-	1.36
34	51.87	C₁₅H₂₂O₂	6-(1-羟甲基乙烯基)-4，8a-二甲基-3，5，6，7，8，8a-六氢-1Hin-2-萘酮	3.48
35	58.10	C₂₃H₃₂O	2-[4-甲基-6-(2，6，6-三甲基环己基-1-烯基)六-1，3，5-三烯基]环己基-1-烯-1-甲醛	0.16

序号	保留时间/min	分子式	化合物名称	相对含量/%
1	4.90	C₃H₁₂O	3甲基-1,3,5-戊三醇	0.06
2	6.84	C₆H₁₂O	3-己烯-1-醇, (Z)-	0.13
3	7.40	C₆H₁₄O	3-甲基-1-戊醇	0.06
4	8.89	C₂₅H₄₄N₂O₅S	2-肉豆蔻酰基脯氨酸	0.02
5	9.59	C₄H₈O₃	4-羟基丁酸	0.05
6	11.38	C₂₅H₄₄N₂O₅S	2-肉豆蔻酰基脯氨酸	0.01
7	11.94	C₆H₁₂O₃	1,3-二氧杂环戊烯-4-乙醇,2,2-二甲基-,(S)-	0.02
8	16.15	C₈H₇N₅O	苯乙烯基醚	0.03
9	17.12	C₁₀H₁₇NO₆S	脱磺酰磷脂	0.04
10	18.97	C₈H₁₅ClO₂	8-氯卡酸	0.12
11	20.11	C₇H₈O	苯甲醇	0.26
12	23.38	C₁₅H₁₃FO₃	3-苄氧基-2-氟-4-甲氧基苯甲醛-	0.21
13	23.90	C₈H₁₀O	苯乙醇	0.39
14	24.87	C₁₀H₁₆O	反式氧化柠檬烯	0.06
15	25.89	C₁₉H₃₄	十九碳三烯	0.01
16	26.62	C₁₀H₁₆O	顺式-薄荷基-2,8-二烯-1-醇	0.03
17	27.09	C₁₀H₁₆	α-松油醇	0.06
18	27.98	C₇H₅NS	苯并噻唑	0.08
19	28.56	C₈H₁₃NO	2-氧-6-氮杂三环[3.3.1.1(3,7)]癸烷	0.03
20	29.12	C₁₅H₂₄	α-依兰油烯	0.07
21	31.30	C₁₅H₂₄	δ-榄香烯	16.82
22	33.06	C₁₅H₂₄	1-甲基-1-2烯基-2,4-二异丙烯基-环己烷	7.05
23	33.84	C₁₅H₂₄	石竹烯	10.68
24	34.82	C₁₅H₂₄	α-蒎烯	1.59
25	35.44	C₁₅H₂₄	大根香叶烯D	6.36
26	36.04	C₁₅H₂₄	异丁香烯	3.09
27	36.49	C₁₅H₂₄	α-愈创烯	1.03
28	38.00	C₁₅H₂₄O	石竹素	3.73
29	38.78	C₁₅H₂₄O	环氧化蛇麻烯Ⅱ	1.29
30	39.43	C₁₅H₂₄O	异匙叶桉油烯醇	5.56
31	40.25	C₁₅H₂₆O	红没药醇氧化物B	1.08
32	41.34	C₁₅H₂₆O	α-红没药醇	9.09
33	41.78	C₁₅H₂₄	β-榄香烯	0.18
34	42.56	C₁₅H₂₄O	α-香根草酮	0.26
35	44.45	C₁₅H₂₄O	(+)匙叶桉油烯醇	0.99
36	45.06	C₁₅H₂₄O	(-)匙叶桉油烯醇	1.42
37	46.61	C₁₅H₂₆O₂	异戊酸香叶酯	0.11
38	47.48	C₂₀H₃₂	樟脑烯	1.25
39	47.74	C₂₆H₄₂O₄	邻苯二甲酸,丁基十四烷基酯	0.1
40	48.69	C₂₀H₃₂	香叶基-α-松油烯	0.13
41	49.16	C₂₀H₃₂	贝壳杉-15-(5α, 9α, 10α)	0.15
42	50.19	C₃₇H₇₆O	1-庚醇	0.11
43	50.92	C₁₆H₃₂O₂	棕榈酸	0.78
44	51.48	C₁₈H₃₆O₂	十六烷酸乙酯	0.17
45	52.53	C₂₀H₃₄O	异瑟模环烯醇	0.11
46	53.30	C₂₀H₃₄O₂	乙基-9,12,15-十八碳三烯	0.04
47	53.58	C₃₇H₇₆O	1-庚醇	0.03
48	54.11	C₂₀H₄₀O	植物醇	0.27
49	54.90	C₁₈H₃₀O₂	9,12,15-十八碳三烯酸,(Z,Z,Z)-	0.67
50	56.36	C₃₀H₅₀O₂	熊果醇	0.32
51	65.78	C₂₁H₃₀O₃	1,6-二苯并呋喃二醇, 5a,6,7,8, 9,9a-六氢-6-甲基-9-(1-甲基乙烯基)-3-戊基-, (5aα,6α,9α,9aα)-	0.54
52	69.35	C₃₀H₄₀O₆	2,4,6-癸三烯酸, 1a,2,5,5a, 6,9,10-八氢-5,5a-二羟基-4-(羟甲基)-1,1,7, 9-四甲基-11-氧代-1H-2,8a-甲基环戊烷[a]环丙基[e]环癸烯-6-基酯, [1aR-(1aα,2α,5á,5aá,6á,8aα,9α,10aα)]-	0.02
53	74.08	C₂₀H₂₈O₅	4a,7a-环氧-5H-环戊二烯[a]环丙基[f]环十一碳烯-4(1H)-酮,1a,6,7, 10,11,11-六氢-7, 10,11-三羟基-1,1,3,6,9-五甲基-	0.02
54	77.94	C₂₁H₂₈O₅	皮质醇	0.01
55	80.68	C₂₆H₅₄	3-乙基-5-(2-乙基丁基)十八烷	0.05
56	88.22	C₃₀H₅₂O	2,2,4-三甲基-3- (3,8,12,16-四甲基-十七碳-3,7,11,15 -四烯基)-环己醇	0.06
57	89.22	C₂₆H₃₂O₇	环[苯并呋喃-3(2H),1'-[2,5]环己二烯]-5-羧酸,6-羟基-2'-甲氧基-2,4'-二氧基-4-戊基-,甲酯	0.02