Heterogeneity Analysis of Volatile Components of Fresh Leaves of Three Perilla Plants

doi:10.3969/j.issn.1000-2561.2020.03.023

Abstract

Abstract:

The leaf Perilla is of specific aroma and of biological activitie. The similarities and differences of the volatile organic compounds in the fresh leaves of P. frutescens (NMZS), P. frutescens var. frutescens (BS) and P. frutescens var. frutescens (ZS) were studied. Solid phase microextraction (SPME) was used to enrich and extract the volatile compounds. The volatile components were isolated and identified by GC-MS. The volatile components were significantly different in three Perilla plants. The three plants could be clustered into a single group by principal component analysis. The high matching (≥90%) and relatively high content (≥2%) volatile componets of three plants were different. The high matching and high content compounds of NMZS were 3,7-dimethyl-2,6-octadienal, (Z)- 3,7- dimethyl-2,6-octadienal, 1-octen-3-ol etc., while those of ZS were α-caryophyllene, β-caryophyllene, apiol etc., and those of BS were β-caryophyllene, 1-octen-3-ol, 3,7-dimethyl-1,6-octadien-3-ol etc. A total of 19 specific volatile components were fould in NMZS (3,7-dimethyl-2,6-octadienal, (Z)-3,7-dimethyl-2,6-Octadienal etc.), eight in BS (Apiol etc.), and six in ZS (3,7-dimethyl-1,6-octadien-3-ol and so on). Common volatiles were also found, which were β-elemene, germacrene D, β-caryophyllene and 1-octen-3-ol. Cluster analysis result showed that BS and ZS could be clustered into one group, while NMZS was clustered into another group. The study would provide a basis for the further development and utilization of Perilla plants.

Key words: Perilla, volatile components, solid-phase microextraction-gas chromatography-mass spectrometry, heterogeneity analysis

CLC Number:

S567.219

LIN Xia,CHEN Zheng,ZHU Yujing,LI Huimin,DENG Wenqiong,LIU Bo. Heterogeneity Analysis of Volatile Components of Fresh Leaves of Three Perilla Plants[J]. Chinese Journal of Tropical Crops, 2020, 41(3): 586-595.

Figures/Tables 9

References 38

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俗名 Common name	分类地位 Classification status	叶片主要特征 Main characteristics of leaves	嗅觉体验 Experience the sense of smell	样品编号 No.	采集地 Source of collection
柠檬紫苏NMZS	Perilla fruteseens 紫苏属	叶正面略带紫色,尤其叶脉周围更显紫色,背面全部为紫色,叶边缘锯齿盾圆形,几乎无毛。	有浓郁柠檬香味	NMZS-1	采集自龙岩山区,移回福建农林大学种植一代
				NMZS-2
				NMZS-3
白苏BS	Perilla fruteseens var. frutescens 紫苏属紫苏	叶正面鲜绿色,背面也是淡绿色,也背面带细绒毛,叶边缘锯齿突尖形。	香气较淡	BS-1	福建农林大学
				BS-2
				BS-3
紫苏ZS	Perilla fruteseens var. frutescens 紫苏属紫苏	叶正面为深绿色,背面除了叶脉都为明显淡紫色,边缘锯齿为宽尖形,两面无毛。	香气浓郁	ZS-1	福建农林大学
				ZS-2
				ZS-3

俗名 Common name	分类地位 Classification status	叶片主要特征 Main characteristics of leaves	嗅觉体验 Experience the sense of smell	样品编号 No.	采集地 Source of collection
柠檬紫苏NMZS	Perilla fruteseens 紫苏属	叶正面略带紫色,尤其叶脉周围更显紫色,背面全部为紫色,叶边缘锯齿盾圆形,几乎无毛。	有浓郁柠檬香味	NMZS-1	采集自龙岩山区,移回福建农林大学种植一代
				NMZS-2
				NMZS-3
白苏BS	Perilla fruteseens var. frutescens 紫苏属紫苏	叶正面鲜绿色,背面也是淡绿色,也背面带细绒毛,叶边缘锯齿突尖形。	香气较淡	BS-1	福建农林大学
				BS-2
				BS-3
紫苏ZS	Perilla fruteseens var. frutescens 紫苏属紫苏	叶正面为深绿色,背面除了叶脉都为明显淡紫色,边缘锯齿为宽尖形,两面无毛。	香气浓郁	ZS-1	福建农林大学
				ZS-2
				ZS-3

序号 No.	中文名 Compound name (in Chinese)		化合物名称 Compound name	CAS号 CAS No.	相对含量/% Relatively content/%
序号 No.	中文名 Compound name (in Chinese)		化合物名称 Compound name	CAS号 CAS No.	柠檬紫苏 NMZS	紫苏 ZS	白苏 BS
1	柠檬醛		3,7-dimethyl-2,6-Octadienal	5392-40-5	22.37	-	-
2	β-石竹烯		β-caryophyllene	87-44-5	19.20	23.77	7.15
3	顺式-柠檬醛		(Z)-3,7-dimethyl-2,6-Octadienal,	106-26-3	14.93	-	-
4	α-石竹烯		α-Caryophyllene	6753-98-6	3.41	3.57	-
5	蘑菇醇		1-Octen-3-ol	3391-86-4	2.30	5.37	5.12
6	大根香叶烯		Germacrene D	23986-74-5	0.73	1.19	0.51
7	β-柠檬醇		(Z)- 3,7-dimethyl-,2,6-Octadien-1-ol	106-25-2	0.53	-	-
8	β-古芸烯		1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-, [1aR-(1aα,7α,7aα,7bα)]-	17334-55-3	0.35	-	-
9	β-榄香烯		β-elemene	515-13-9	0.34	0.47	0.12
10	双环大根香叶烯		Bicyclogermacrene	67650-90-2	0.31	-	-
11	香茅醛		6-Octenal, 3,7-dimethyl-	106-23-0	0.24	-	-
12	1-乙烯基-1-甲基-2-(1-甲基乙烯基)-4-(1-甲基亚乙基)-环己烷		1-ethenyl-1-methyl-2-(1-methylethenyl)-4-(1-methylethylidene)- Cyclohexane	3242-8-8	0.22	-	-
13	壬烷		Humulen-(v1)	1000159-39-4	0.18	-	-
14	γ-榄香烯		γ-Elemene	30824-67-0	0.17	-	-
15	石竹烯氧化物		Caryophyllene oxide	1139-30-6	0.15	1.83	-
16	反式石竹烯		Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-	13877-93-5	0.12	-	-
17	(Z)-3,7-二甲基-1,3,6-十八烷三烯		1,3,6-Octatriene, 3,7-dimethyl-, (Z)-	3338-55-4	0.10	-	-
18	2-甲氧基-5-丙-2-烯基苯酚		3-Allyl-6-methoxyphenol	501-19-9	0.07	-	-
19	δ-杜松烯		Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)-	483-76-1	0.07	-	0.13
20	(1α,4aα,8aα)-1,2,3,4,4a,5,6, 8a-7-甲基-4-甲基-4-甲基-4-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)-, (1α,4aα,8aα)- Naphthalene	30021-74-0	0.05	-	-
21	别香橙烯		allo-aromadendrene	25246-27-9	0.05	-	0.05
22	(+)-双环倍半水芹烯		(+)-Epi-bicyclosesquiphellandrene	54324-03-7	0.05	0.09	-
23	衣兰烯		Ylangene	14912-44-8	0.05	-	-
24	1-甲基-4-(1-甲基乙烯基)苯		1-methyl-4-(1-methylethenyl)- benzene	1195-32-0	0.04	-	-
25	反式-橙花叔醇		(E)- 3,7,11-trimethyl-, 1,6,10-Dodecatrien-3-ol	40716-66-3	0.04	-	-
26	1,2,4a,5,6,8a-六氢-4,7-二甲基-1-(1-甲基乙基)-萘		1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-naphthalene	483-75-0	0.04	-	-
27	古巴烯		Copaene	3856-25-5	0.03	-	0.15
28	乙位紫罗兰酮		4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-Buten-2-one,	14901-07-6	0.03	-	-
29	6-乙酰-6-甲基-1-(1-甲基乙基)-3-(1-甲基亚乙基)-环己烯		6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1-methylethylidene)- Cyclohexene,	5951-67-7	0.03	-	-
30	α-荜澄茄油烯		α-Cubebene	17699-14-8	0.02	0.42	-
31	α-法呢烯		α-Farnesene	502-61-4	-	1.14	0.29
32	香橙烯		Aromandendrene	489-39-4	-	0.2	-
33	2,5,6-三甲基-1,3,6-庚三烯		2,5,6-trimethyl-1,3,6-Heptatriene	42123-66-0	-		0.67
34	2,6-二甲基-6-(4-甲基-3-戊烯基)双环[3.1.1]七碳-2-烯		Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)-	17699-05-7	-	9.51	-
35	(-)-β-波旁烯		(-)-β-Bourbonene	5208-59-3	-	0.03	0.07
36	苯甲醛		Benzaldehyde	100-52-7	-		0.53
序号 No.	中文名 Compound name (in Chinese)	化合物名称 Compound name		CAS号 CAS No.	相对含量/% Relatively content/%
序号 No.	中文名 Compound name (in Chinese)	化合物名称 Compound name		CAS号 CAS No.	柠檬紫苏 NMZS	紫苏 ZS	白苏 BS
37	芳樟醇	3,7-dimethyl-1,6-Octadien-3-ol		78-70-6	-		3.58
38	β-愈创木烯	β-Guaiene		88-84-6	-		0.04
39	肉豆蔻醚	1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)-		607-91-0	-	0.19	-
40	洋芹脑	Apiol		523-80-8	-	6.33	-
41	3,7,11-三甲基-1,3,6,10-十二碳-四烯	3,7,11-trimethyl-1,3,6,10-Dodecatetraene		26560-14-5	-		2.15
42	1,5,9,9-四甲基-1,4,7-环十一碳-三烯	1,5,9,9-tetramethyl-,1,4,7,-cycloundecatriene		1000062-61-9	-	6.59	0.62
43	α-广藿香萜烯	α-Patchoulene		560-32-7	-	0.12	-
44	1a,2,3,3a,4,5,6,7b-八氢-1,1, 3a,7-四甲基-, [1aR-(1aα, 3aα, 7bα)]-1H-环丙烷[a]萘,	1a, 2, 3, 3a, 4, 5, 6, 7b-octahydro-1,1,3a,7-tetramethyl-, [1aR-(1aα, 3aα, 7bα)]-, 1H-cyclopropa[a]naphthalene,		489-29-2	-	0.12	-
45	牦牛儿酸甲酯	2,6-Octadienoic acid, 3,7-dimethyl-, methyl ester		2349-14-6	-		0.11
46	2-异丙基-5-甲基-9-亚甲基- 双环[4.4.0] -1-癸烯,	2-isopropyl-5-methyl-9-methylene-Bicyclo[4.4.0]dec-1-ene,		150320-52-8	-	0.17	-
47	[1R-(1α,4aα,8aα)],1,2,4a,5,6,8a-六氢-4,7-二甲基-1-(1-甲基乙基)-萘	[1R-(1α,4aα,8aα.)]-1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, Naphthalene,		17627-24-6	-	0.12	-
48	橙花叔醇	Nerolidol		1000285-43-6	-	0.05	-
总计					66.34	61.28	21.29

序号 No.	中文名 Compound name (in Chinese)		化合物名称 Compound name	CAS号 CAS No.	相对含量/% Relatively content/%
序号 No.	中文名 Compound name (in Chinese)		化合物名称 Compound name	CAS号 CAS No.	柠檬紫苏 NMZS	紫苏 ZS	白苏 BS
1	柠檬醛		3,7-dimethyl-2,6-Octadienal	5392-40-5	22.37	-	-
2	β-石竹烯		β-caryophyllene	87-44-5	19.20	23.77	7.15
3	顺式-柠檬醛		(Z)-3,7-dimethyl-2,6-Octadienal,	106-26-3	14.93	-	-
4	α-石竹烯		α-Caryophyllene	6753-98-6	3.41	3.57	-
5	蘑菇醇		1-Octen-3-ol	3391-86-4	2.30	5.37	5.12
6	大根香叶烯		Germacrene D	23986-74-5	0.73	1.19	0.51
7	β-柠檬醇		(Z)- 3,7-dimethyl-,2,6-Octadien-1-ol	106-25-2	0.53	-	-
8	β-古芸烯		1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-, [1aR-(1aα,7α,7aα,7bα)]-	17334-55-3	0.35	-	-
9	β-榄香烯		β-elemene	515-13-9	0.34	0.47	0.12
10	双环大根香叶烯		Bicyclogermacrene	67650-90-2	0.31	-	-
11	香茅醛		6-Octenal, 3,7-dimethyl-	106-23-0	0.24	-	-
12	1-乙烯基-1-甲基-2-(1-甲基乙烯基)-4-(1-甲基亚乙基)-环己烷		1-ethenyl-1-methyl-2-(1-methylethenyl)-4-(1-methylethylidene)- Cyclohexane	3242-8-8	0.22	-	-
13	壬烷		Humulen-(v1)	1000159-39-4	0.18	-	-
14	γ-榄香烯		γ-Elemene	30824-67-0	0.17	-	-
15	石竹烯氧化物		Caryophyllene oxide	1139-30-6	0.15	1.83	-
16	反式石竹烯		Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-	13877-93-5	0.12	-	-
17	(Z)-3,7-二甲基-1,3,6-十八烷三烯		1,3,6-Octatriene, 3,7-dimethyl-, (Z)-	3338-55-4	0.10	-	-
18	2-甲氧基-5-丙-2-烯基苯酚		3-Allyl-6-methoxyphenol	501-19-9	0.07	-	-
19	δ-杜松烯		Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)-	483-76-1	0.07	-	0.13
20	(1α,4aα,8aα)-1,2,3,4,4a,5,6, 8a-7-甲基-4-甲基-4-甲基-4-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)-, (1α,4aα,8aα)- Naphthalene	30021-74-0	0.05	-	-
21	别香橙烯		allo-aromadendrene	25246-27-9	0.05	-	0.05
22	(+)-双环倍半水芹烯		(+)-Epi-bicyclosesquiphellandrene	54324-03-7	0.05	0.09	-
23	衣兰烯		Ylangene	14912-44-8	0.05	-	-
24	1-甲基-4-(1-甲基乙烯基)苯		1-methyl-4-(1-methylethenyl)- benzene	1195-32-0	0.04	-	-
25	反式-橙花叔醇		(E)- 3,7,11-trimethyl-, 1,6,10-Dodecatrien-3-ol	40716-66-3	0.04	-	-
26	1,2,4a,5,6,8a-六氢-4,7-二甲基-1-(1-甲基乙基)-萘		1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-naphthalene	483-75-0	0.04	-	-
27	古巴烯		Copaene	3856-25-5	0.03	-	0.15
28	乙位紫罗兰酮		4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-Buten-2-one,	14901-07-6	0.03	-	-
29	6-乙酰-6-甲基-1-(1-甲基乙基)-3-(1-甲基亚乙基)-环己烯		6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1-methylethylidene)- Cyclohexene,	5951-67-7	0.03	-	-
30	α-荜澄茄油烯		α-Cubebene	17699-14-8	0.02	0.42	-
31	α-法呢烯		α-Farnesene	502-61-4	-	1.14	0.29
32	香橙烯		Aromandendrene	489-39-4	-	0.2	-
33	2,5,6-三甲基-1,3,6-庚三烯		2,5,6-trimethyl-1,3,6-Heptatriene	42123-66-0	-		0.67
34	2,6-二甲基-6-(4-甲基-3-戊烯基)双环[3.1.1]七碳-2-烯		Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)-	17699-05-7	-	9.51	-
35	(-)-β-波旁烯		(-)-β-Bourbonene	5208-59-3	-	0.03	0.07
36	苯甲醛		Benzaldehyde	100-52-7	-		0.53
序号 No.	中文名 Compound name (in Chinese)	化合物名称 Compound name		CAS号 CAS No.	相对含量/% Relatively content/%
序号 No.	中文名 Compound name (in Chinese)	化合物名称 Compound name		CAS号 CAS No.	柠檬紫苏 NMZS	紫苏 ZS	白苏 BS
37	芳樟醇	3,7-dimethyl-1,6-Octadien-3-ol		78-70-6	-		3.58
38	β-愈创木烯	β-Guaiene		88-84-6	-		0.04
39	肉豆蔻醚	1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)-		607-91-0	-	0.19	-
40	洋芹脑	Apiol		523-80-8	-	6.33	-
41	3,7,11-三甲基-1,3,6,10-十二碳-四烯	3,7,11-trimethyl-1,3,6,10-Dodecatetraene		26560-14-5	-		2.15
42	1,5,9,9-四甲基-1,4,7-环十一碳-三烯	1,5,9,9-tetramethyl-,1,4,7,-cycloundecatriene		1000062-61-9	-	6.59	0.62
43	α-广藿香萜烯	α-Patchoulene		560-32-7	-	0.12	-
44	1a,2,3,3a,4,5,6,7b-八氢-1,1, 3a,7-四甲基-, [1aR-(1aα, 3aα, 7bα)]-1H-环丙烷[a]萘,	1a, 2, 3, 3a, 4, 5, 6, 7b-octahydro-1,1,3a,7-tetramethyl-, [1aR-(1aα, 3aα, 7bα)]-, 1H-cyclopropa[a]naphthalene,		489-29-2	-	0.12	-
45	牦牛儿酸甲酯	2,6-Octadienoic acid, 3,7-dimethyl-, methyl ester		2349-14-6	-		0.11
46	2-异丙基-5-甲基-9-亚甲基- 双环[4.4.0] -1-癸烯,	2-isopropyl-5-methyl-9-methylene-Bicyclo[4.4.0]dec-1-ene,		150320-52-8	-	0.17	-
47	[1R-(1α,4aα,8aα)],1,2,4a,5,6,8a-六氢-4,7-二甲基-1-(1-甲基乙基)-萘	[1R-(1α,4aα,8aα.)]-1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, Naphthalene,		17627-24-6	-	0.12	-
48	橙花叔醇	Nerolidol		1000285-43-6	-	0.05	-
总计					66.34	61.28	21.29

序号 No.	中文名 Compound name (in Chinese)	相对含量 Relatively content/%
序号 No.	中文名 Compound name (in Chinese)	柠檬紫苏 NMZS	紫苏 ZS	白苏 BS
1	柠檬醛	22.37	-	-
2	β-石竹烯	19.20	23.77	7.15
3	顺式-柠檬醛	14.93	-	-
4	α-石竹烯	3.41	3.57
5	蘑菇醇	2.30	5.37	5.12
6	2,6-二甲基-6-(4-甲基-3-戊烯基)双环[3.1.1]七碳-2-烯	-	9.51	-
7	芳樟醇	-		3.58
8	洋芹脑	-	6.33	-
9	3,7,11-三甲基-1,3,6,10-十二碳-四烯	-		2.15
10	1,5,9,9-四甲基-1,4,7-环十一碳-三烯	-	6.59	-
总计		62.21	55.14	18.00