English

• 人参是多年生五加科草本植物人参(Panax Ginseng C.A. Mey.)的干燥根和根茎，具有生津养血、安神益智和抑制肿瘤等功效^[1]。人参中活性成分主要包括人参皂苷、人参多糖、氨基酸、挥发性成分等^[2]，其中人参皂苷与人参糖类的研究较多^[3-5]。人参挥发性成分气味独特，抗疲劳等功能性产品已上市。人参中的挥发性成分质量分数仅为0.1%~0.5%，但其消炎、镇咳、抗疲劳、使神经中枢兴奋等作用明显，还能够通过抑制癌细胞的核酸代谢、糖代谢达到抑制癌细胞生长的作用^[6]，其中β-榄香烯在抗癌方面得到了较多的研究和关注^[7-8]。人参有生晒参和红参等不同炮制品，功效不同，气味也不同，生晒参中炔醇类物质较蒸制过的炮制品中含量高，其对革兰阳性金黄色葡萄球菌、枯草芽孢杆菌、肺炎双球菌等抑菌作用更强^[9]，同时其抗肿瘤和神经保护等活性更强^[10-11]。气相色谱-质谱联用(GC-MS/MS)技术与NIST MS Spectral Database结合使用，常用作脂肪酸和挥发性成分的测定^[12-13]。本研究采用水蒸气回流提取法结合气相色谱-三重四极杆质谱联用检测技术^[14-15]，建立了GC-MS/MS测定人参挥发性成分的方法，应用于对鲜参、生晒参和红参中挥发性成分的比较，明确鲜参及其炮制品挥发性成分的组成，推断生晒参和红参中的挥发性成分衍生路径，为人参炮制机理的研究提供挥发性成分的化学数据。

  1   实验部分

  1.1   仪器和试剂、药材

  TRACE 1310 GC-Triple Quadrupole MS型气相色谱串联质谱仪(美国Thermo Science公司)。

  正己烷(色谱纯，TEDIA公司)，蒸馏水(实验室自制)。鲜参(5年生)；生晒参(由同批次鲜参人参挖出洗净放置通风阴凉处阴干后的炮制品)；红参(由同批次鲜参经过清洗、分选、蒸制5 h后、50 ℃烘干等工序加工而成)。

  1.2   实验方法

  1.2.1   样品提取

  精密称取粉碎后过150 μm筛的样品100 g，加入600 mL水，水蒸气回流提取8 h，将提取到的挥发性转移至离心管中，并用2 mL正己烷冲洗容器内壁，涡旋3 min，取正己烷层，从中准确吸取20 μL于1 mL容量瓶中，用正己烷稀释并定容，即得供试品溶液。生晒参和红参按照炮制前后重量比例提取制备。

  1.2.2   GC-MS操作条件

  GC条件：TG-5SILMS非极性色谱柱(30 m×0.25 mm×0.25 μm)。进样口温度为250 ℃，初始温度50 ℃，保持3 min；升温程序，从50 ℃开始，先以5 ℃/min升至120 ℃，再以1 ℃/min升至125 ℃，保持3 min，再以1 ℃/min升至130 ℃，保持3 min，再以1 ℃/min升至135 ℃，保持3 min，再以1 ℃/min升至140 ℃，保持3 min，再以1 ℃/min升至145 ℃，保持3 min，再以1 ℃/min升至150 ℃，保持3 min；载气为He，载气流量为1.2 mL/min；分流比为35，进样量为1 μL。

  MS条件：EI离子源，进样口温度270 ℃，离子源温度250 ℃，传输线温度250 ℃，扫描范围50~500m/z。

  2   结果与讨论

  2.1   挥发性成分的定性分析

  从图 1可以看出，鲜参、生晒参和红参中的挥发性成分差异较大，在化合物数量和含量方面，炮制前后及不同方法炮制均对挥发性成分有显著的影响。

  图1 鲜参总离子色谱图(A)、生晒参总离子色谱图(B)和红参总离子色谱图(C) Figure1. The total ion chromatography of the fresh ginseng(A), the sun-dry(B) and the red ginseng(C)

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  GC-MS由于具有恒定的70 eV电离能和标准数据库，因此能够不使用标准对照品，鉴定挥发性成分^[16-17]。本研究通过GC-MS/MS一级质谱图分子量和二级串联质谱子离子信息，与NIST MS Spectral Database数据库比对，鉴定了40个人参中的挥发性化合物，具体如表 1所示。

  表 1  鲜参、生晒参、红参挥发性成分定性分析 Table 1.  The volatile components in qualitative analysis of fresh ginseng, sun-dry ginseng and red ginseng

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  No.	Retention time/min	Compounds	Formula	Molecular mass	Relative peak area
  					Fresh	Sun-Dry	Red
  					ginseng	ginseng	ginseng
  1	6.96	α-Pinene	C10H16	136	1	0.24	0.77
  2	7.43	Camphene	C10H16	136	1	0.17	0.53
  3	8.27	β-Pinene	C10H16	136	1	0.24	0.38
  4	8.66	Ningene	C10H16	136	1	1.98	1.05
  5	9.07	Octanal	C8H10O	128	1	4.90	1.70
  6	15.85	Benzene, 2-methoxy-4-methyl-1-(1-methyl)-	C11H16O	164	1	0.48	-
  7	16.78	Cyclodecanone	C10H18O	154	-	+	+
  8	17.31	6-(5-Methyl-furan-2-yl)-hexan-2-one	C11H16O2	180	-	++	+
  9	18.13	Cedrene	C15H24	204	1	0.51	0.76
  10	18.93	β-Elemene	C15H24	204	1	0.71	0.61
  11	19.14	4, 4, 6-Trimethyl-cyclohex-2-en-1-ol	C9H16O	140	-	+	-
  12	19.52		C14H20O	204	1	0.83	0.56
  13	19.93	2-(3-Isopropyl-4-methyl-pent-3-en-1-ynyl)-2-methyl-cyclobutanone	C14H20O	204	1	1.11	0.72
  14	20.95	Ginsengene	C15H24	204	1	1.29	0.67
  15	21.24	Caryophyllene	C15H24	204	1	0.77	0.70
  16	21.76	Neoclovene	C15H24	204	1	-	0.40
  17	22.22	Aromadendrene	C15H24	204	1	1.15	0.89
  18	22.64	Aristolene	C15H24	204	1	0.90	0.77
  19	23.21	α-Elemene	C15H24	204	1	1.52	0.89
  20	23.65	Farnesene	C15H24	204	-	-	++
  21	24.50	Transcaryophyllene	C15H24	204	1	0.88	0.68
  22	24.76	Ai Li Mo phenol	C15H24	204	1	1.09	1.04
  23	25.22	β-Selinene	C15H24	204	1	0.32	0.49
  24	25.63	δ-Cadinene	C15H24	204	1	1.05	0.58
  25	26.47	á-Guaiene	C15H24	204	-	++	-
  26	26.63	1H-Cycloprop[e]azulene, 1a, 2, 3, 5, 6, 7, 7a, 7b-octahydro-1, 1, 4, 7-tetramethyl-, [1aR-(1aà, 7à, 7aá, 7bà)]-	C15H24	204	1	1.21	2.97
  27	26.87	Azulene, 1, 2, 3, 3a, 4, 5, 6, 7-octathydro-1, 4, dimethyl-7-(1-methylethenyl)-, [1R, (1à, 3aá, 4à, 7á)]-	C15H24	204	1	0.16	0.27
  28	27.56	Naphthalene, 1, 2, 3, 5, 6, 7, 8, 8a-octahydro-1, 8a-dimethyl-7-(1-methylthemyl)-, [1R-(1à, 7á, 8aà)]-	C15H24	204	++	-	-
  29	28.44	1-(1, 5-dimethylhexyl)-4-methylbenzene	C15H24	204	1	0.93	1.10
  30	30.26		C15H26O	222	1	1.86	1.66
  31	32.04	New ginseng terpene alcohols	C15H26O	222	-	-	++
  32	32.61	(-)-Spathulenol	C15H24O	220	1	31.98	5.47
  33	33.24	β-Piperonyl butylene	C15H24	204	1	1.86	-
  34	33.35	Globulol	C15H26O	222	-	-	++
  35	33.94	ξ-EIMACHALENE	C15H26O	222	1	1.42	4.32
  35	34.83	7-epi-cis-Sesquisabinene	C15H26O	222	-	-	++
  37	35.02	à-Acorenol	C15H26O	222	1	-	3.74
  38	35.22	Caryophyllene oxide	C15H24O	220	-	++	-
  39	35.97	4-epi-Cubedol	C15H26O	222	-	++	+
  40	37.42	2H-3, 9a-Methanol-1-benzoxepin, octahydro-2, 2, 5a, 9-tetramethyl-, [3R-(3à, 5aà, 9à, 9aà)]-	C15H26O	222	1	2.10	1.35
  In the table:the peak area of compound in fresh ginseng was 1 and the relationship area of processed ginseng was calculated by ratio between the amount of processed ginseng and fresh ginseng. “-”:none of the components, “+”:indicates the peak area of 106, “++”:peak area is 107, “+++”:peak area of 108.

  由表 1和图 2可知，鲜参、生晒参和红参中共检测出40种挥发性成分，其中烯类22种，醛类1种，酮类3种，醇类8种，杂环类6种。鲜参共中检测出烯类20种挥发性成分，醛类1种，酮类1种，醇类4种，杂环类4种，共30种挥发性成分；生晒参中检测出烯类20种，醛类1种，酮类3种，醇类4种，杂环类5种，共33种挥发性成分；红参中检测出烯类19种，醛类1种，酮类3种，醇类8种，杂环类3种，共34种挥发性成分。

  图2 鲜参、生晒参、红参挥发性成分定性分析比较 Figure2. The comparison of the volatile compounds in fresh ginseng, sun-dry ginseng and red ginseng

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  2.2   炮制过程中挥发性成分的转化

  由图 2中发性成分研究结果可知，生晒参在阴干或晾干过程中挥发性成分有部分损失，使含量降低或挥发性成分种类减少，有少数新挥发性成分生成；红参由于经过高温蒸制及低温烘干等热处理后，一部分挥发性成分含量明显增高，推测是由与其结构相似的挥发性成分转化而来，使其含量增加。推断炮制后部分发现的新挥发性成分的衍生途径如表 2。

  表 2  挥发性成分存在的转化关系 Table 2.  Transformation relationship of volatile components

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  No.	Raw material		Transformation products
  	Structural formula	Compounds	Structural formula	Compounds
  1		α-Pinene		4, 4, 6-Trimethyl-cyclohex-2-en-1-ol
  2		Aromandendrene		(-)-Spathulenol
  3		α-Elemene		Farnesene
  4		Ginsengene		New ginseng terpene alcohols
  5		1H-Cycloprop[e]azulene, 1a, 2, 3, 5, 6, 7, 7a, 7b-octahydro-1, 1, 4, 7-tetramethyl-, [1aR-(1aà, 7à, 7aá, 7bà)]-		Globulol

  炮制过程中，鲜参中具有不饱和双键的挥发性成分，加热条件下，易发生加成反应，生成饱和的或部分饱和的加成产物。人参中化学成分含量较多且相互作用复杂，红参的炮制过程中化学成分之间相互作用，有大量酶参与反应，故一些含量较高的成分不能确定是由结构相似的化合物转化而得，其生成过程有待进一步研究和讨论。

  生晒参中(-)-斯巴醇含量为鲜参含量的31.98倍，为红参含量的5.84倍，是生晒参中检测出最多的挥发性成分。研究表明，(-)-斯巴醇属聚炔醇类化合物，是五加科植物中较常见的成分，具有很强的抗肿瘤活性，可抑制血管紧张素Ⅱ诱导的血管收缩，降低自发性高血压大鼠平均动脉压，同时还具有抗炎及抗血小板凝集活性。人参脂溶性成分(含聚醇类)具明显促进神经细胞生长的活性，可降低血压、降血脂及对冠心病患者有食疗作用^[18-21]。由于鲜参、生晒参和红参中艾里莫酚烯含量均相对较高，且可能转化为(-)-斯巴醇，由此可见鲜参在晾晒成生晒参时，一部分艾里莫酚烯转化为(-)-斯巴醇，使生晒参在抗肿瘤活性、降血压、降血脂方向的作用更加明显。

  红参中金合欢烯是鲜参和生晒参中均不含有的特有成分，有报道^[22]称金合欢醇具有消炎健胃作用，民间将金合欢醇用于治疗风湿扭伤等病，符合无梗五加在《中华本草》中传统药理的记载。由于鲜参中不含该成分，不具有该功效，但由于鲜参中含有的α-榄香烯含量较红参高，且在鲜参炮制成红参的过程中可能转化为金合欢烯，故红参较鲜参增加了消炎健胃的作用。

  3   结论

  本文通过气相色谱-质谱联用方法，检测了鲜参、生晒参、红参中的挥发性成分，并对炮制前后差异较大的化合物进行了衍生规律推测，结合已报道的化合物生物活性，从挥发性成分的角度阐释了人参炮制品的物质基础，为人参的临床应用和规范化炮制质量控制提供了化学数据支持。

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  图 1  鲜参总离子色谱图(A)、生晒参总离子色谱图(B)和红参总离子色谱图(C)

  Figure 1  The total ion chromatography of the fresh ginseng(A), the sun-dry(B) and the red ginseng(C)

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  图 2  鲜参、生晒参、红参挥发性成分定性分析比较

  Figure 2  The comparison of the volatile compounds in fresh ginseng, sun-dry ginseng and red ginseng

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  表 1  鲜参、生晒参、红参挥发性成分定性分析

  Table 1.  The volatile components in qualitative analysis of fresh ginseng, sun-dry ginseng and red ginseng

  No.	Retention time/min	Compounds	Formula	Molecular mass	Relative peak area
  					Fresh	Sun-Dry	Red
  					ginseng	ginseng	ginseng
  1	6.96	α-Pinene	C10H16	136	1	0.24	0.77
  2	7.43	Camphene	C10H16	136	1	0.17	0.53
  3	8.27	β-Pinene	C10H16	136	1	0.24	0.38
  4	8.66	Ningene	C10H16	136	1	1.98	1.05
  5	9.07	Octanal	C8H10O	128	1	4.90	1.70
  6	15.85	Benzene, 2-methoxy-4-methyl-1-(1-methyl)-	C11H16O	164	1	0.48	-
  7	16.78	Cyclodecanone	C10H18O	154	-	+	+
  8	17.31	6-(5-Methyl-furan-2-yl)-hexan-2-one	C11H16O2	180	-	++	+
  9	18.13	Cedrene	C15H24	204	1	0.51	0.76
  10	18.93	β-Elemene	C15H24	204	1	0.71	0.61
  11	19.14	4, 4, 6-Trimethyl-cyclohex-2-en-1-ol	C9H16O	140	-	+	-
  12	19.52		C14H20O	204	1	0.83	0.56
  13	19.93	2-(3-Isopropyl-4-methyl-pent-3-en-1-ynyl)-2-methyl-cyclobutanone	C14H20O	204	1	1.11	0.72
  14	20.95	Ginsengene	C15H24	204	1	1.29	0.67
  15	21.24	Caryophyllene	C15H24	204	1	0.77	0.70
  16	21.76	Neoclovene	C15H24	204	1	-	0.40
  17	22.22	Aromadendrene	C15H24	204	1	1.15	0.89
  18	22.64	Aristolene	C15H24	204	1	0.90	0.77
  19	23.21	α-Elemene	C15H24	204	1	1.52	0.89
  20	23.65	Farnesene	C15H24	204	-	-	++
  21	24.50	Transcaryophyllene	C15H24	204	1	0.88	0.68
  22	24.76	Ai Li Mo phenol	C15H24	204	1	1.09	1.04
  23	25.22	β-Selinene	C15H24	204	1	0.32	0.49
  24	25.63	δ-Cadinene	C15H24	204	1	1.05	0.58
  25	26.47	á-Guaiene	C15H24	204	-	++	-
  26	26.63	1H-Cycloprop[e]azulene, 1a, 2, 3, 5, 6, 7, 7a, 7b-octahydro-1, 1, 4, 7-tetramethyl-, [1aR-(1aà, 7à, 7aá, 7bà)]-	C15H24	204	1	1.21	2.97
  27	26.87	Azulene, 1, 2, 3, 3a, 4, 5, 6, 7-octathydro-1, 4, dimethyl-7-(1-methylethenyl)-, [1R, (1à, 3aá, 4à, 7á)]-	C15H24	204	1	0.16	0.27
  28	27.56	Naphthalene, 1, 2, 3, 5, 6, 7, 8, 8a-octahydro-1, 8a-dimethyl-7-(1-methylthemyl)-, [1R-(1à, 7á, 8aà)]-	C15H24	204	++	-	-
  29	28.44	1-(1, 5-dimethylhexyl)-4-methylbenzene	C15H24	204	1	0.93	1.10
  30	30.26		C15H26O	222	1	1.86	1.66
  31	32.04	New ginseng terpene alcohols	C15H26O	222	-	-	++
  32	32.61	(-)-Spathulenol	C15H24O	220	1	31.98	5.47
  33	33.24	β-Piperonyl butylene	C15H24	204	1	1.86	-
  34	33.35	Globulol	C15H26O	222	-	-	++
  35	33.94	ξ-EIMACHALENE	C15H26O	222	1	1.42	4.32
  35	34.83	7-epi-cis-Sesquisabinene	C15H26O	222	-	-	++
  37	35.02	à-Acorenol	C15H26O	222	1	-	3.74
  38	35.22	Caryophyllene oxide	C15H24O	220	-	++	-
  39	35.97	4-epi-Cubedol	C15H26O	222	-	++	+
  40	37.42	2H-3, 9a-Methanol-1-benzoxepin, octahydro-2, 2, 5a, 9-tetramethyl-, [3R-(3à, 5aà, 9à, 9aà)]-	C15H26O	222	1	2.10	1.35
  In the table:the peak area of compound in fresh ginseng was 1 and the relationship area of processed ginseng was calculated by ratio between the amount of processed ginseng and fresh ginseng. “-”:none of the components, “+”:indicates the peak area of 106, “++”:peak area is 107, “+++”:peak area of 108.

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  表 2  挥发性成分存在的转化关系

  Table 2.  Transformation relationship of volatile components

  No.	Raw material		Transformation products
  	Structural formula	Compounds	Structural formula	Compounds
  1		α-Pinene		4, 4, 6-Trimethyl-cyclohex-2-en-1-ol
  2		Aromandendrene		(-)-Spathulenol
  3		α-Elemene		Farnesene
  4		Ginsengene		New ginseng terpene alcohols
  5		1H-Cycloprop[e]azulene, 1a, 2, 3, 5, 6, 7, 7a, 7b-octahydro-1, 1, 4, 7-tetramethyl-, [1aR-(1aà, 7à, 7aá, 7bà)]-		Globulol

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