Volatile compounds from bamboo vinegar with HS-SPME and GC-MS

LIU Qing; TONG Senmiao; MA Jianyi

doi:10.11833/j.issn.2095-0756.2014.02.022

Volume 31 Issue 2

Mar. 2014

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LIU Qing, TONG Senmiao, MA Jianyi. Volatile compounds from bamboo vinegar with HS-SPME and GC-MS[J]. Journal of Zhejiang A&F University, 2014, 31(2): 308-314. doi: 10.11833/j.issn.2095-0756.2014.02.022

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LIU Qing, TONG Senmiao, MA Jianyi. Volatile compounds from bamboo vinegar with HS-SPME and GC-MS[J]. Journal of Zhejiang A&F University, 2014, 31(2): 308-314. doi: 10.11833/j.issn.2095-0756.2014.02.022

Volatile compounds from bamboo vinegar with HS-SPME and GC-MS

doi: 10.11833/j.issn.2095-0756.2014.02.022

School of Forestry and Biotechnology, Zhejiang A & F University, Lin'an 311300, Zhejiang, China

Received Date: 2013-04-26
Rev Recd Date: 2013-06-20
Publish Date: 2014-04-20

Abstract

Our former work has discovered that bamboo vinegar may be a new olfactory disturbance agent against mosquitoes. It is necessary that the further work on volatile organic compounds from original and refined bamboo vinegar in order to display effect of mosquito repellent. Original and refined bamboo vinegar VOCs were extracted using two kinds of extraction fiber heads with different polarity and then analyzed by gas chromatography-mass spectrometry (GC-MS) and headspace solid-phase microextraction (HS-SPME). The result showed that extraction of 54 compounds from original bamboo vinegar and 57 compounds from refined bamboo vinegar, respectively. From the original bamboo vinegar, the polydimethylsiloxane (PDMS) fiber extracted 41 compounds:mainly 2-methoxy-phenol (9.0%), 4-ethyl-phenol (8.4%), and phenol (6.5%); and the polyacrylate (PA) fiber extracted 32 compounds:primarily phenol (17.2%), 2-methoxy-phenol (12.7%), and acetic acid (11.8%). From the refined bamboo vinegar, the PDMS fiber extracted 42 compounds:mainly-methoxy-phenol (12.1%), 4-ethyl-phenol (8.9%), and phenol (6.8%) with the PA fiber extracting 35 compounds:mostly phenol (19.7%), 2-methoxy-phenol (14.7%), and acetic acid (6.7%). These results showed that for acids, phenol, and aldehyde from the original and refined bamboo vinegar, extraction with the PA fiber had a stronger adsorptive attraction than the PDMS fiber head. The PA fiber was superior in the adsorption of acids; whereas, the adsorptive attraction of the PDMS textile fiber head on the ketones and alkenes surpassed the PA textile fiber head's. The corresponding fiber may be used to extract the target component owing to improving precision effect on extracting various ingredients of bamboo vinegar.
- bamboo vinegar,
- VOCS,
- HS-SPME,
- GC-MS

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References

[1]	HAN Liang, ZHAO Ting, ZOU Yanmin, et al. Studies on component analysis and antifungal activity of bamboo vinegar[J]. J Jiangsu Univ, 2011, 2(2):167-174.
[2]	ZHANG Wenbiao, LI Wenzhu, FANG Wei, et al. A study on bamboo vinegar components and their formation process at different collection temperature[J]. J Bamboo Res, 2008, 27(4):44-49.
[3]	MU J, UEHARA T, FUMNO T. Effect of bamboo vinegar on regulation of germination and radicle growth of seed plants (Ⅱ)composition of moso bamboo vinegar at different collection temperature and its effects[J]. J Wood Sci, 2005, 50:470-476.
[4]	CUI Yu, WU Liangru. Present situation and prospect of bamboo vinegar study in China[J]. J Bamboo Res, 2010, 29(1):11-16.
[5]	MU J, UEHARA T, FURUNO T. Effect of bamboo vinegar on regulation of germination and radicle growth of seed plants[J]. J Wood Sci, 2003, 49:262-270.
[6]	LIN H C, OHUCHI T, SHIAH T C, et al. Application of bamboo vinegar with vacuum process to evaluate fungi resistance of bamboo materials[J]. J Facul Agric Kyushu Univ, 2006, 53(1):107-113.
[7]	VELMURUGAN N, CHUN S S, HAN S S, et al. Characterization of chikusaku-eki and mokusaku-eki and its inhibitory effect on sapstaining fungal growth in laboratory scale[J]. Int J Environ Sci Tech, 2009, 6(1):13-22.
[8]	WANG Pinwei, TONG Senmiao. Development research for bamboo vinegar as potential plant growth regulator:laboratory test and field investigation[J]. Word Bamboo Rattan, 2008, 6(1):5-9.
[9]	JUN Mu, YU Zhiming, WU Wenqiang, et al. Preliminary study of application effect of bamboo vinegar on vegetable growth[J]. For Stud China, 2006, 8(3):43-47.
[10]	SULAIMAN O, MURPHY R J, HASHIM R, et al. The inhibition of microbial growth by bamboo vinegar[J]. J Bamboo and Rattan, 2005, 4(1):7l-80.
[11]	WANG H F, WANG J L, WANG C, et al. Effect of bamboo vinegar as an antibiotic alternative on growth performance and fecal bacterial communities of weaned piglets[J]. Livestock Sci, 2012, 144(1/2):173-180.
[12]	YAN L, KIM I H, HUH K. Influence of bamboo vinegar supplementation on growth performance, apparent total tract digestibility, blood characteristics, meat quality, fecal noxious gas content, and fecal microbial concentration in finishing pigs[J]. Livestock Sci, 2012, 144(3):240-246.
[13]	KATAOKA H, SAITO K. Recent advances in SPME techniques in biomedical analysis[J]. J Pharm Biomed Anal, 2011, 54(5):926-950.
[14]	OUYANG Gangfeng, PAWLISZYN J. SPME in environmental analysis[J]. Anal Bioanal Chem, 2006, 386:1059-1073.
[15]	AKAKABE Y, TAMURA Y, IWAMOTO S, et al. Volatile organic compounds with characteristic odor in bamboo vinegar[J]. Biosci Biotechnol Biochem, 2006, 70(11):2797-2799.
[16]	WANG Jin, CUI Yu, YUE Yongde, et al. Comparison of two sample pretreatment methods for volatile composition analysis of bamboo vinegar[J]. Food Sci, 2011, 32(18):198-201.

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竹醋液是一种成分相当复杂的混合性溶液,是竹材在热解或干馏过程中产生的一种棕褐色液体,其挥发性物质具有特殊的烟熏味,其主要成分为酸类、酚类、醛类、酮类和酯类化合物^[1-3]。中国从20世纪90年代末开始研究竹醋液,至今为止很多科研工作者和企业对竹醋液的开发应用做了大量研究^[4]。有研究表明,竹醋液在农业上可作为植物生长调节剂使用,如促进植物的发芽及根系的生长等,在养殖业上可作为动物饲料添加剂以调节动物生长,在医药卫生及环境保护上可作为杀菌剂、抑菌剂使用^[5-12]。固相微萃取(SPME)是20世纪90年代初推出的一个新的采样和样品制备方法,一方面减少了样品的分析时间,另一方面节省了溶剂处理成本,属于非溶剂型萃取法^[13],现已被广泛应用到采样和分析环境、食物、香气、法医鉴定和药物样品等方面^[14]。目前,国内外对精制前后竹醋液挥发性有机化合物的研究还比较少^[15-16]。因此,本实验拟在室温条件下采用2种不同极性萃取纤维头的顶空-固相微萃取法(HS-SPME),采集精制前后竹醋液的挥发性有机化合物,并进行气相色谱-质谱(GC-MS)分析比较,以明确精制前后竹醋液挥发性有机化合物的含量、成分及各萃取纤维头对不同化合物的吸附效果,为竹醋液挥发性有机化合物的进一步研究提供一定的依据。

1. 材料与方法

1.1. 材料

竹醋原液为浙江富来森中竹科技股份有限公司生产。精制竹醋液为浙江富来森中竹科技股份有限公司生产的竹醋原液经过浙江农林大学森林保护实验室中旋转蒸发仪制得。

1.2. 样品采集

采用固相微萃取方法,利用2种极性纤维萃取头收集竹醋液的挥发性化合物,这2种萃取纤维头分别为100 μm聚二甲基硅氧烷(PDMS)和聚丙烯酸酯(PA,美国Supelco)。在样品采集前,首先将固相微萃取进样器上的萃取头在气相色谱的进样口活化,活化温度为250 ℃,活化时间为30 min。取适量的竹醋原液置于自制的样品瓶中,打开盖子插入萃取纤维头,于室温(15±5) ℃下顶空取样30 min。然后,在GC-MS(HP7890GC/5975MS,美国Agilent)进样口解吸3 min进行GC-MS分析。在其他条件不变的情况下,依次用另外一种萃取纤维头进行同样操作。

1.3. GC-MS分析

GC条件：色谱柱为HP-5(30 m × 0.25 mm × 0.25 μm),进样口温度250 ℃,初始柱温60 ℃,10 ℃·min^-1升温至230 ℃,保留30 min。载气：氦气,流速1 mL·min^-1,柱前压71 kPa,分流比10:1。

MS条件：EI离子源,电离能源70 eV,四极杆(MS Quard)温度150 ℃,离子源温度(MS Source)230 ℃,调谐方式：标准调谐,质量扫描方式：SCAN,溶剂延迟：1 min,扫描范围30~500,电子倍增器电压：1 635 V。

对萃取出来的挥发性成分用标准质谱数据库NIST 0.8L进行匹配对照解析,选用匹配度85%以上结果,采用峰面积归一化法计算相对相对含量同时根据保留指数和参考文献进行定性。

3. 讨论

本实验中采用2种不同极性纤维头,使用HS-SPME法萃取竹醋原液与精制液挥发性有机化合物并对其进行GC-MS分析。在主要类别上如酸类测得精制前后竹醋液相对含量分别为PDMS得0和 0.41%,而PA测得15.11%和9.14%,可见PA纤维头对酸类有较好的吸附力,并且发现精制后的竹醋液的酸类相对含量呈现下降趋势。酚类是竹醋液的最主要成分,精制前PDMS测得酚类相对含量为56.75%,PA测得酚类相对含量为71.73%,精制后PDMS测得酚类相对含量为65.55%,PA测得酚类相对含量为82.90%。从总离子流色谱图来看,PA纤维头萃取的化合物峰面积要远大于PDMS纤维头。由此可以推出：PA纤维头萃取的化合物的绝对含量要远高于PDMS纤维头。其精制前后种类有明显变化,如：PDMS测得酚类由之前的20种变为24种,PA测得酚类由之前的18种变为28种,对于其种类明显增加的原因有待于进一步研究。酮类在精制前后种类和相对含量均呈现下降的趋势,如：PDMS测得酮类由之前的10种变为6种,相对含量由之前的7.79%变为5.04%,而PA测得酮类由之前的6种变为1种,相对含量由之前的3.32%变为0.20%。醛类在种类上无显著变化但相对含量略有下降如：PDMS测得由1.58%下降为1.50%,PA测得由3.55%下降为2.45%。烯类中PDMS测得由4种6.95%下降为2种0.54%,PA测得由2种0.49%下降为0。

2种纤维头在竹醋原液中共测出54种成分,其中共有成分19种,非共有成分35种。在精制液中2种纤维头共测出57种成分,其中共有成分20种,非共有成分37种。另外,在主要成分上,PA纤维头对精制前后竹醋液中酸类、酚类、醛类的吸附力优于PDMS纤维头,在酮类和烯类上PDMS纤维头的吸附力要优于PA纤维头。在研究其中某一成分时要适当选择样品与纤维头,如：PA纤维头对乙酸的吸附力较好,但精制后的乙酸含量会大幅减少,其对苯酚的吸附力也较好,但精制后苯酚的含量会上升。由此可见,不同极性的纤维头吸附挥发性有机化合物的种类和含量不同,并且对同一共有成分其萃取能力也有所不同。因此仅用1种萃取纤维头很难全面了解精制前后竹醋液的挥发性成分,应该根据不同的成分选择使用不同极性的萃取纤维头进行萃取,才能更加确切地掌握其挥发性成分,从而有效利用资源并为进一步研究指明方向。

Reference (16)

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[2]	张文标, 李文珠, 方伟. 不同收集温度的竹醋液组分及形成过程分析[J]. 竹子研究汇刊, 2008, 27(4): 44-49.	ZHANG Wenbiao, LI Wenzhu, FANG Wei. A study on bamboo vinegar components and their formation process at different collection temperature[J]. J Bamboo Res, 2008, 27(4): 44-49.
[3]	MU J, UEHARA T, FUMNO T. Effect of bamboo vinegar on regulation of germination and radicle growth of seed plants (Ⅱ)composition of moso bamboo vinegar at different collection temperature and its effects[J]. J Wood Sci, 2005, 50(): 470-476.
[4]	崔宇, 吴良如. 我国竹醋液发展现状和展望[J]. 竹子研究汇刊, 2010, 29(1): 11-16.	CUI Yu, WU Liangru. Present situation and prospect of bamboo vinegar study in China[J]. J Bamboo Res, 2010, 29(1): 11-16.
[5]	MU J, UEHARA T, FURUNO T. Effect of bamboo vinegar on regulation of germination and radicle growth of seed plants[J]. J Wood Sci, 2003, 49(): 262-270. doi: 10.1007/s10086-002-0472-z
[6]	LIN H C, OHUCHI T, SHIAH T C. Application of bamboo vinegar with vacuum process to evaluate fungi resistance of bamboo materials[J]. J Facul Agric Kyushu Univ, 2006, 53(1): 107-113.
[7]	VELMURUGAN N, CHUN S S, HAN S S. Characterization of chikusaku-eki and mokusaku-eki and its inhibitory effect on sapstaining fungal growth in laboratory scale[J]. Int J Environ Sci Tech, 2009, 6(1): 13-22. doi: 10.1007/BF03326056
[8]	WANG Pinwei, TONG Senmiao. Development research for bamboo vinegar as potential plant growth regulator:laboratory test and field investigation[J]. Word Bamboo Rattan, 2008, 6(1): 5-9.
[9]	JUN Mu, YU Zhiming, WU Wenqiang. Preliminary study of application effect of bamboo vinegar on vegetable growth[J]. For Stud China, 2006, 8(3): 43-47. doi: 10.1007/s11632-006-0023-6
[10]	SULAIMAN O, MURPHY R J, HASHIM R. The inhibition of microbial growth by bamboo vinegar[J]. J Bamboo and Rattan, 2005, 4(1): 7l-80.
[11]	WANG H F, WANG J L, WANG C. Effect of bamboo vinegar as an antibiotic alternative on growth performance and fecal bacterial communities of weaned piglets[J]. Livestock Sci, 2012, 144(1/2): 173-180.
[12]	YAN L, KIM I H, HUH K. Influence of bamboo vinegar supplementation on growth performance, apparent total tract digestibility, blood characteristics, meat quality, fecal noxious gas content, and fecal microbial concentration in finishing pigs[J]. Livestock Sci, 2012, 144(3): 240-246. doi: 10.1016/j.livsci.2011.11.020
[13]	KATAOKA H, SAITO K. Recent advances in SPME techniques in biomedical analysis[J]. J Pharm Biomed Anal, 2011, 54(5): 926-950. doi: 10.1016/j.jpba.2010.12.010
[14]	OUYANG Gangfeng, PAWLISZYN J. SPME in environmental analysis[J]. Anal Bioanal Chem, 2006, 386(): 1059-1073. doi: 10.1007/s00216-006-0460-z
[15]	AKAKABE Y, TAMURA Y, IWAMOTO S. Volatile organic compounds with characteristic odor in bamboo vinegar[J]. Biosci Biotechnol Biochem, 2006, 70(11): 2797-2799. doi: 10.1271/bbb.60317
[16]	王进, 崔宇, 岳永德. 2种前处理方法分析竹醋液挥发性成分的比较[J]. 食品科学, 2011, 32(18): 198-201.	WANG Jin, CUI Yu, YUE Yongde. Comparison of two sample pretreatment methods for volatile composition analysis of bamboo vinegar[J]. Food Sci, 2011, 32(18): 198-201.

序号	化合物	竹醋原液中相对含量/%		精制液中相对含量/N
序号	化合物	PDMS/匹配度	PA/匹配度	PDMS/匹配度	PA/匹配度
1	乙酸	-	11.8/91	0.41/86	6.65/91
2	丙酸	-	2.23/90	-	1.36/86
3	丁酸	-	1.08/90	-	1.13/90
4	苯酚？	-	-	-	3.27/92
5	苯酚？	-	0.86/94	1.03/90	0.19/87
6	苯酚？	6.48/94	17.23/97	6.80/94	19.66/95
7	2-甲基-苯酚？	4.17/97	8.01/97	5.16/97	9.40/97
8	2-甲基-苯酚？	-	-	0.61/93	0.73/96
9	2-甲基-苯酚？	-	-	-	0.45/94
10	3-甲基-苯酚	0.78/91	-	-	0.65/91
11	4-甲基-苯酚？	5.31/97	7.74/96	6.11/97	9.02/97
12	4-甲基-苯酚？	-	-	0.59/96	-
13	2-甲氧基-苯酚？	9.03/97	-	-	1.57/95
14	2-甲氧基-苯酚？	-	12.73/96	12.09/95	14.72/96
15	2-甲氧基-苯酚？	-	-	1.67/90	-
16	2,6-二甲基-苯酚	1.57/97	1.27/97	2.08/97	1.45/97
17	3,5-二甲基-苯酚？	-	-	-	0.30/90
18	3,5-二甲基-苯酚？	-	2.20/97	3.36/97	2.93/97
19	2-乙基-苯酚	0.97/95	0.78/95	1.27/95	0.98/95
20	2,3-二甲基-苯酚	0.45/96	0.24/96	0.52/96	-
21	2,4-二甲基-苯酚	2.82/97	-	-	-
22	3-乙基-苯酚	-	-	-	0.09/89
23	4-乙基-苯酚？	8.36/95	5.15/95	8.86/95	5.64/95
24	4-乙基-苯酚？	-	-	0.79/92	-
25	2,6-二甲氧基-苯酚	1.90/97	0.71/97	0.21/93	0.06/87
26	2-甲氧基-4-甲基-苯酚？	-	0.57/89	1.23/93	0.43/95
27	2-甲氧基-4-甲基-苯酚？	5.32/95	3.85/97	7.12/97	4.57/95
28	2-甲氧基-3-甲基-苯酚	1.04/94	-	1.42/94	-
29	4-甲氧基-3-甲基-苯酚	-	0.74/93	-	1.00/93
30	2-甲氧基-4-丙基-苯酚	-	-	0.52/96	0.18/91
31	2-甲基-6-丙基-苯酚	0.11/91	-	-	-
32	2,4,6-三甲基-苯酚	0.37/95	0.21/95	0.63/95	0.33/95
33	3,-乙基-5-甲基-苯酚	-	-	-	0.42/90
34	4,-乙基-3-甲基-苯酚	-	-	-	0.70/87
35	2,-乙基-6-甲基-苯酚	1.25/97	-	0.85/87	-
36	4，-乙基-2-甲氧基-苯酚？	-	-	-	0.21/90
37	4，-乙基-2-甲氧基-苯酚？ 2,4-双"1,1-二甲基乙基#-苯	5.18/91	2.52/91	7.41/91	3.00/91
38	酚			0.98/86
39	3-"1-甲基乙基$-苯酚 2-甲氧基-3-%2-丙烯基$-苯	-	0.56/87	-	-
40	酚 2-甲氧基-4-"1-丙烯基$-		0.18/97
41	(M)-苯酚			0.42/95
42	2-甲氧基-5-甲基苯酚	0.88/90	-	-	0.76/93
43	1,2,3-三甲氧基-苯酚	0.32/87	-	-	-
44	丁子香酚	0.44/97	-	-	0.19-96
45	糠醛？	0.83/93	0.39-95	0.41-87	0.74-95
46	糠醛？	0.16/93	2.76-94	0.15-93	1.00-90
47	糠醛？	-	-	0.94-95	-
48	3-糠醛	0.12/87	-	-	-
49	5-甲基-2-呋喃甲醛？	0.47/94	-	-	-
50	5-甲基-2-呋喃甲醛？	-	0.40-97	-	0.71-93
51	二丁基羟基甲苯？	-	-	0.45-99	-
52	二丁基羟基甲苯？	-	-	0.33-96	-
53	二丁基羟基甲苯？	-	-	0.39-98	-
54	二丁基羟基甲苯？	-	-	0.42-91	-
55	1，2,3-三甲氧基-5-甲基苯	-	-	0.12-93	-
56	榄香烯？	0.20/98	0.24-97	-	-
57	榄香烯？	4.20/91	-	-	-
58	石竹烯	0.18/99	-	-	-
59	2,6-二甲基-2,6-辛二烯	2.37/97	0.25-97	-	-
60	1,3-二甲基-1-环己烯	-	-	0.37-90	-
61	2-甲基-1,3-丁二烯	-	-	0.17-91	-
62	2,3-二氢-1H-茚-1-酮	0.55/96	-	0.62-97	0.20-97
63	1-(2-呋喃基5 -乙酮	1.42/91	1.66-86	1.35-86	-
64	2-甲基-2-环戊烯-1-酮	-	0.10-91	1.07-94	-
65	3-甲基-1" 2-二环戊酮	-	0.86-94	-	-
66	2-甲基-2-环戊烯-1-酮	1.15/94	-	-	-
67	3-乙基-2-环戊烯-1-酮	0.44/87	0.16-87	-	-
68	3-乙基-2-羟基-2-环戊烯-1- 酮	0.87/96	0.44-96	-	-
69	3,4-二甲基-2-环戊烯-1-酮	0.30-95	0.10-94	0.32-95	-
70	2,3-二甲基-2-环戊烯-1-酮？	0.85-94	-	1.07-90	-
71	2,3-二甲基-2-环戊烯-1-酮？	1.31-93	-	0.61-87	-
72	2-环戊烯-1-酮	0.60-93	-	-	-
73	环戊酮	0.30-87	-	-	-
74	1,5-二甲基-2,6-双（亚甲基） -环辛烷	0.22-89	-	-	-
75	十四烷	-	-	0.14-95	-
76	柠檬精油	0.59-92	-	-	-
77	1,2,4,5,6,8a-六化氢-4,7-二甲基-1-(1-甲基乙基）-萘	0.29-96	-	-	-
说明 : "一" 表示未检出 ; "?"表示未能判断确切化合物种类。

序号	化合物	竹醋原液中相对含量/%		精制液中相对含量/%
序号	化合物	PDMS	PA	PDMS	PA
1	酸类	-	15.11	0'41	9'14
2	酚类	56.75	65'55	71'73	82'90
3	醛类	1.58	3'55	1'50	2'45
4	烯类	6.95	0'49	0'54	-
5	酮类	7.79	3'32	5'04	0'20
6	其他	1.1	-	0'14	-
7	芳香类	-	-	1'71	-
8	总计	74'17	88'02	81'07	94'69

Volatile compounds from bamboo vinegar with HS-SPME and GC-MS

doi: 10.11833/j.issn.2095-0756.2014.02.022