基质固相分散和HPLC-IT-TOF/MS联用研究漆树木材中多酚成分

doi:10.3969/j.issn.0253-2417.2022.01.002

Abstract

Abstract:

Matrix solid-phase dispersion was proposed to extract polyphenols in Toxicodendron vernicifluum (Stokes) F. A. Barkl. (Shaanxi lacquer tree). The MSPD conditions to extract polyphenols established by the single factor test were ZSM-22 as the adsorbent, adsorbent/sample ratio of 2:1 (g: g), grinding for 2 min, and use of 8 mL of 70% methanol as the elution solvent. Under these conditions, the polyphenols content of MSPD extraction was (466 ±2. 05)mg/g(calculated by gallic acid). An efficient and accurate method for identification of polyphenols in Shaanxi lacquer tree was established by HPLC-IT-TOF/MS. According to mass spectrometry, fragmentation pathway combined with published reports, total of 10 components were identified, including 3 gallic acid derivatives and 7 flavonoids as follows: gallic acid, methyl gallate, ethyl gallate, fustin, taxifolin, garbanzol, isorhamnetin, quercitrin, fisetin, sulfuretin. It was beneficial to the discovery and identification of compounds in Shaanxi lacquer tree by matrix solid-phase dispersion coupled with HPLC-IT-TOF/MS, and it could be significance for the analysis and quantification of extracts from Shaanxi lacquer tree samples.

Key words: matrix solid-phase dispersion, lacquer tree, polyphenols, HPLC-ESI-TOF-MS

CLC Number:

TQ351

Hongxia CHEN, Hao ZHOU, Ran TAO, Zhiwen QI, Wenjun LI, Chengzhang WANG. Study on Polyphenols in Lacquer Tree by Matrix Solid-phase Dispersion and HPLC-IT-TOF/MS[J]. Chemistry and Industry of Forest Products, 2022, 42(1): 10-20.

Figures/Tables 12

Fig.1

Fig.2

Table 1

Fig.3

Fig.4

Fig.5

Fig.6

Fig.7

Fig.8

Fig.9

Fig.10

Table 2

References 22

1	郑勉, 闵天禄. 中国植物志45(1): 漆树科[M]. 北京: 科学出版社, 1980: 111- 113.
	ZHENG M , MIN T L . Flora of China 45(1): Anacardiaceae[M]. Beijing: Science Press, 1980: 111- 113.
2	KIM J S , KWON Y S , CHUN W J , et al. Rhus verniciflua Stokes flavonoid extracts have anti-oxidant, anti-microbial and α-glucosidase inhibitory effect[J]. Food Chemistry, 2010, 120, 539- 543. doi: 10.1016/j.foodchem.2009.10.051
3	KANG Y , YOON S W , PARK B , et al. Allergen-removed Rhus verniciflua Stokes suppresses invasion and migration of pancreatic cancer cells through downregulation of the JAK/STAT and Src/FAK signaling pathways[J]. Oncology Reports, 2018, 40, 3060- 3068.
4	NAM T G , LEE B H , CHOI H K , et al. Rhus verniciflua Stokes extract and its flavonoids protect PC-12 cells against H₂O₂-induced cytotoxicity[J]. Journal of Microbiology and Biotechnology, 2017, 27 (6): 1090- 1097. doi: 10.4014/jmb.1612.12018
5	LEE H Y, LEE G H, YOON Y, et al. R.verniciflua and E.ulmoides extract(ILF-RE) protects against chronic CCl₄-induced liver damage by enhancing antioxidation[J/OL]. Nutrients, 2019, 11(2): 1-17[2020-10-10]. https://doi.org/10.3390/nu11020382.
6	LIM J W , SHIN S M , JUNG S J , et al. Optimization of antibacterial extract from lacquer tree(Rhus vernici ƒƖua Stokes) using response surface methodology and its efficacy in controlling edwardsiellosis of olive flounder(Paralichthys olivaceus)[J]. Aquaculture, 2019, 502, 40- 47. doi: 10.1016/j.aquaculture.2018.12.008
7	陈虹霞, 王成章, 叶建中, 等. 漆树多酚的负压提取工艺及其抑制酪氨酸酶活性的研究[J]. 林产化学与工业, 2015, 35 (2): 47- 54.
	CHEN H X , WANG C Z , YE J Z , et al. Phenolic extracts from Rhus verniciflua Stokes woods by vacuum extraction and their anti-tyrosinase activities[J]. Chemistry and Industry of Forest Products, 2015, 35 (2): 47- 54.
8	GHOLAMI H , ARABI M , GHAEDI M , et al. Column packing elimination in matrix solid phase dispersion by using water compatible magnetic molecularly imprinted polymer for recognition of melamine from milk samples[J]. Journal of Chromatography A, 2019, 1594, 13- 22. doi: 10.1016/j.chroma.2019.02.015
9	ŚMIEłOWSKA M , ZABIEGAłA B . Matrix solid-phase dispersion(MSPD) as simple and useful sample preparation technique for determination of polybrominated diphenyl ethers(PBDEs) in dust[J]. Analytica Chimica Acta, 2019, 1084, 33- 42. doi: 10.1016/j.aca.2019.08.001
10	WU X , ZHANG X X , YANG Y Q , et al. Development of a deep eutectic solvent-based matrix solid phase dispersion methodology for the determination of aflatoxins in crops[J]. Food Chemistry, 2019, 291, 239- 244. doi: 10.1016/j.foodchem.2019.04.030
11	GOMEZMEJIA E , ROSALESCONRADO N , LEONGONZALEZ M E , et al. Determination of phenolic compounds in residual brewing yeast using matrix solid-phase dispersion extraction assisted by titanium dioxide nanoparticles[J]. Journal of Chromatography A, 2019, 1601, 255- 265. doi: 10.1016/j.chroma.2019.05.009
12	OYEDEJI A O , MSAGATI T A M , WILLIAMS A B , et al. Determination of antibiotic residues in frozen poultry by a solid-phase dispersion method using liquid chromatography-triple quadrupole mass spectrometry[J]. Toxicology Reports, 2019, 6, 951- 956. doi: 10.1016/j.toxrep.2019.09.005
13	KAPSIMALI D , ROSENBERG E , ZACHARIADIS G A . Investigation of the HPLC-IT-TOF-MS technique with atmospheric pressure chemical ionization for speciation of selenoaminoacids, dimethyldiselenide, and diphenyldiselenide[J]. Analytical Letters, 2012, 45 (5/6): 642- 650.
14	SUN J , SONG Y L , ZHANG J , et al. Characterization and quantitative analysis of phenylpropanoid amides in eggplant(Solanum melongena L.) by high performance liquid chromatography coupled with diode array detection and hybrid ion trap time-of-flight mass spectrometry[J]. Journal of Agricultural and Food Chemistry, 2015, 63 (13): 3426- 3436. doi: 10.1021/acs.jafc.5b00023
15	KIM S K , KIM S H , KIM I S , et al. Simultaneous determination of bioactive phenolic compounds in the stem extract of Rhus verniciflua stokes by high performance liquid chromatography[J]. Food Chemistry, 2013, 141, 3813- 3819. doi: 10.1016/j.foodchem.2013.06.068
16	YANG C J, WANG Z B, MI Y Y, et al.UHPLC-MS/MS determination, pharmacokinetic, and bioavailability study of taxifolin in rat plasma after oral administration of its nanodispersion[J/OL]. Molecules, 2016, 21: 1-11[2020-10-10]. https://doi.org/10.3390/molecules21040494.
17	JANG J Y, SHIN H, LIM J W, et al.Comparison of antibacterial activity and phenolic constituents of bark, lignum, leaves and fruit of Rhus verniciflua[J/OL]. PLoS ONE, 2018, 13(7): 1-13[2020-10-10]. https://doi.org/10.1371/journal.pone.0200257.
18	SCHIEBER A , KELLER P , STREKER P , et al. Detection of isorhamnetin glycosides in extracts of apples(Malus domestica cv."Brettacher") by HPLC-PDA and HPLC-APCI-MS/MS[J]. Phytochemical Analysi, 2002, 13, 87- 94. doi: 10.1002/pca.630
19	第五文博, 谈娜娜, 王晓玲, 等. 元宝枫叶中的黄酮类成分分析与电喷雾质谱裂解规律研究[J]. 宝鸡文理学院学报(自然科学版), 2020, 40 (3): 25- 33.
	DIWU W B , TAN N N , WANG X L , et al. Analysis of flavonoids from Acer truncatum bunge leaves and study on the fragmentation patterns in electrospray ionization mass spectrometry[J]. Journal of Baoji University of Arts and Sciences(Natural Science), 2020, 40 (3): 25- 33.
20	SOKOLOVÁ R , RAMEŠOVÁ Š , KOCÁBOVÁ J , et al. On the difference in decomposition of taxifolin and luteolin vs.fisetin and quercetin in aqueous media[J]. Monatshefte Fuer Chemie/Chemical Monthly, 2016, 147, 1375- 1383. doi: 10.1007/s00706-016-1737-3
21	LIU C S , NAM T G , HAN M W , et al. Protective effect of detoxified Rhus verniciflua stokes on human keratinocytes and dermal fibroblasts against oxidative stress and identification of the bioactive phenolics[J]. Journal of the Agricultural Chemical Society of Japan, 2013, 77 (8): 1682- 1688.
22	JEONG H J , PARK J H , KIM M J , et al. Optimization of the extraction process for fermented Rhus verniciflua Stokes using response surface methodology[J]. Food Science and Biotechnology, 2016, 25, 179- 184. doi: 10.1007/s10068-016-0027-5

峰号 No.	t/min	准分子离子峰 quasi-molecular ion peak	负离子模式下碎片峰 fragment peak in negative ion mode	分子式 molecular formula	鉴定结果 appraisal result
1	1.133	169.0173[M-H]^-	125.0277	C₇H₆O₅	没食子酸 gallic acid
2	3.187	183.0321[M-H]^-	125.0192	C₈H₈O₅	没食子酸甲酯 methyl gallate
3	6.200	197.0482[M-H]^-	169.0171, 124.9759	C₉H₁₀O₅	没食子酸乙酯 ethyl gallate
4	7.400	287.0564[M-H]^- 289.0703[M+H]⁺	269.0497, 254.9302, 226.9803, 150.9935	C₁₅H₁₂O₆	黄颜木素 fustin
5	9.587	303.0521[M-H]^- 305.0668[M+H]⁺	275.0532, 271.0604, 242.9193, 179.0254, 150.9933	C₁₅H₁₂O₇	花旗松素 taxifolin
6	10.760	271.0631[M-H]^- 273.0755[M+H]⁺	243.0669, 238.9312, 226.9801, 162.9949	C₁₅H₁₂O₅	3, 4′, 7-三羟基黄烷酮 garbanzol
7	11.933	315.0512[M-H]^- 317.0651[M+H]⁺	301.0479, 255.0420, 178.9299, 150.9933	C₁₆H₁₂O₇	异鼠李素 isorhamnetin
8	13.453	447.0941[M-H]^- 449.1070[M+H]⁺	300.0273, 271.2206, 255.0471, 242.9359	C₂₁H₂₀O₁₁	槲皮苷 quercitrin
9	14.720	285.0405[M-H]^- 287.0552[M+H]⁺	257.0923, 228.9805, 162.9942	C₁₅H₁₀O₆	漆黄素 fisetin
10	17.920	269.0454[M-H]^- 271.0597[M+H]⁺	240.9241, 222.9809, 136.9943	C₁₅H₁₀O₅	硫黄菊素 sulfuretin

提取方法 extraction method	分析方法 analysis method	分析物¹⁾ analyte	样品量/g sample dose	溶剂solvent		条件condition		参考文献 reference
提取方法 extraction method	分析方法 analysis method	分析物¹⁾ analyte	样品量/g sample dose	种类 type	用量 dose/mL	时间/min time	温度/℃ temp.	参考文献 reference
热回流提取 heat reflux extraction	UV	总多酚 total polyphenols	1	水 water	25	555	89.95	[22]
热回流提取 heat reflux extraction	LC-MS/MS	主要化学成分 main chemical	3	60%乙醇水溶液alcohol solution	90	600	85	[6]
热回流提取 heat reflux extraction	LC-MS/MS	主要化学成分 main chemical	100	水water	1000	180	100	[15]
负压提取 vacuum extraction	UV	总多酚 total polyphenols	5	83%乙醇水溶液 alcohol solution	100	90	—	[7]
MSPD	UV+ HPLC-IT-TOF/MS	总多酚，主要化学成分 total polyphenols, main chemical	0.2	70%甲醇水溶液 methanol solution	8	30	常温 room temp.	本研究 this study

[1]	Hongxia CHEN, Hao ZHOU, Jianzhong YE, Ran TAO, Wenjun LI, Chengzhang WANG. Matrix Solid-phase Dispersion Combined with GC-MS for Determination of Chemical Constituents of Essential Oil in Agarwood [J]. Chemistry and Industry of Forest Products, 2021, 41(3): 47-54.
[2]	Xiaojie WANG,Lixin HUANG,Caihong ZHANG,Pujun XIE,Yejun DENG,Lujie LIU. Preparation and Physicochemical Properties of Olive Leaf Extract [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 83-90.
[3]	Yan PENG,Kehua TANG,Aiwen DONG. Purification of Bletilla striata Polyphenols by Macroporous Resin and Its Antioxidant Activities in Vitro [J]. Chemistry and Industry of Forest Products, 2019, 39(4): 91-99.
[4]	Huifang ZHANG,Ye WANG,Weichao HU,Shu YUAN,Ming YUAN. Purification and Antioxidation Activity of Polyphenol from Cyrtomium fortune [J]. Chemistry and Industry of Forest Products, 2019, 39(2): 81-88.
[5]	WANG Xiang, PENG Sheng, PENG Mijun. Extraction of Total Polyphenols from Eucommia ulmoides Oliver Leaves Assisted by Ultrasound-microwave and Their Antioxidant Activity [J]. Chemistry and Industry of Forest Products, 2018, 38(5): 85-92.
[6]	YAO Fengqi, TAO Junjun, WANG Haihui, HU Guoqing, CHEN Shuai, TAHIR Mudassir Hussian. Study of Pyrolysis Behavior and Reaction Mechanism of Tea Polyphenols [J]. Chemistry and Industry of Forest Products, 2017, 37(5): 19-27.
[7]	HUANG Yong-lin, CHEN Yue-yuan, YAN Xiao-jie, LIU Jin-lei, WANG Ya-feng, HE Rui-jie, LI Dian-peng. Composition of Polyphenols in Bark of Castanopsis fargesii Franch. [J]. Chemistry and Industry of Forest Products, 2016, 36(4): 135-139.
[8]	ZHOU Hao, LI Wen-jun, ZHANG Jun, ZHANG Yu-si, YAN Xin-pei, WANG Cheng-zhang. Screening, Separation and Purification of Mulberry Leaf Polyphenols [J]. Chemistry and Industry of Forest Products, 2015, 35(6): 133-140.
[9]	FENG Jun-feng, JIANG Jian-chun, XU Jun-ming, HE Xiao-liang, YANG Zhong-zhi, XU Le. Separation and Utilization of Classification Products in Liquefied Oil of Biomass [J]. Chemistry and Industry of Forest Products, 2014, 34(6): 61-68.
[10]	YOU Feng, HUANG Lin-xin, ZHANG Cai-hong, XIE Pu-jun, ZHANG Yao-lei. Ultrasound-assisted Vacuum Extraction of Polyphenols from Jujube Peel [J]. Chemistry and Industry of Forest Products, 2014, 34(1): 107-112.
[11]	QIU Zhen-yu;TANG Ming-li;ZHANG Xuan;ZHANG Ping-ping;WU Li-fang. Extraction of Polyphenols from Leaves of Rhus chinensis Mill and Its Antioxidant Activity [J]. , 2013, 33(1): 107-112.
[12]	CHEN Hong-xia;WANG Cheng-zhang;ZHOU Hao;YE Jian-zhong. Research Progress of Phenolic Compounds from Wanlnut(Juglans regia L.) [J]. , 2013, 33(1): 130-134.
[13]	DONG Yan-he;WANG Cheng-zhang;YE Jian-zhong;YUAN Jiao-jiao;ZHOU Yan;HE Yuan-feng. Physicochemical Properties of Lacquer Oils [J]. , 2012, 32(4): 28-32.
[14]	DONG Yan-he;WANG Cheng-zhang;GONG Kun;ZHANG Fei-long. Research Progress on Chemical Constituents and Comprehensive Application of Lacquer Trees [J]. , 2009, 29(S1): 225-232.
[15]	WANG Chang-lu;REN Lu;CHEN Zhi-qiang;JIANG Shen-hua;LIU Chang-jin;XIA Lian-fa. Study on Antioxidant Effects of Polyphenols from Old Leaves of Toona sinensis (A. Juss) Roem [J]. , 2008, 28(5): 89-92.

Study on Polyphenols in Lacquer Tree by Matrix Solid-phase Dispersion and HPLC-IT-TOF/MS

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 12

References 22

Related Articles 15

Recommended Articles

Metrics

Comments