HPLC-Q-TOF-MS在线筛选鉴定牡丹花中的抗氧化成分

doi:10.3976/j.issn.1002-4026.2022.05.002

Abstract

Abstract:

A high performance liquid chromatography-quadrupole time of flight mass spectrometry (HPLC-Q-TOF-MS) combined with on-line removal of 1,1-diphenyl-2-picrylhydrazyl (DPPH) model was established for the rapid screening and identification of antioxidant active ingredients in peony flowers. Waters X-Bridge C₁₈ chromatographic column was used with acetonitrile-water (0.1% formic acid) as the mobile phase. The peony flower samples were analyzed using electrospray positive and negative ion modes. The samples separated using HPLC were mixed with free-radical solution, and the mixture was entered into HPLC-Q-TOF-MS for rapid identification. In total, 15 ingredients and 5 antioxidant compounds were identified in the negative ion mode. This method is a simple method for rapid screening and identification of antioxidant compounds in a complex system of natural products. Furthermore, it can also provide scientific basis for further studies on peony flower.

Key words: peony flower, antioxidant activity, on-line screening, HPLC-Q-TOF-MS

CLC Number:

O657.72

TIAN Xuan, LIU Yu, ZHU Wen-qing, ZHENG Zhen-Jia. Identification of antioxidant components in peony flowers through on-line screening using high performance liquid chromatography-quadrupole time of flight mass spectrometer[J].Shandong Science, 2022, 35(5): 10-15.

Figures/Tables 3

Fig.1

Fig.2

Table 1

References 30

[1]	李凯, 周宁, 李赫宇. 牡丹花、牡丹籽成分与功能研究进展[J]. 食品研究与开发, 2012, 33(3): 228-230. DOI: 10.3969/j.issn.1005-6521.2012.03.066. doi: 10.3969/j.issn.1005-6521.2012.03.066
[2]	闫慧娇, 王志伟, 陈燕平, 等. 凤丹牡丹花瓣化学成分研究[J]. 山东科学, 2017, 30(3): 12-16. DOI: 10.3976/j.issn.1002-4026.2017.03.003. doi: 10.3976/j.issn.1002-4026.2017.03.003
[3]	吴晓莹. 牡丹叶片和花瓣营养成分分析研究[D]. 长沙: 湖南农业大学, 2017.
[4]	SUN G P, WANG H, XU S P, et al. Anti-tumor effects of paeonol in a HepA-hepatoma bearing mouse model via induction of tumor cell apoptosis and stimulation of IL-2 and TNF-α production[J]. European Journal of Pharmacology, 2008, 584(2/3): 246-252. DOI: 10.1016/j.ejphar.2008.02.016. doi: 10.1016/j.ejphar.2008.02.016
[5]	WU S H, WU D G, CHEN Y W. Chemical constituents and bioactivities of plants from the genus Paeonia[J]. Chemistry & Biodiversity, 2010, 7(1). DOI: 10.1002/cbdv.200800148. doi: 10.1002/cbdv.200800148
[6]	ZHAO M, WU S P. A review of the ethnobotany, phytochemistry and pharmacology of tree peony (Sect. Moutan)[J]. South African Journal of Botany, 2019, 124: 556-563. DOI: 10.1016/j.sajb.2019.05.018. doi: 10.1016/j.sajb.2019.05.018
[7]	王晓, 时新刚, 郑成超, 等. 牡丹花提取物清除活性氧及对·OH引发的DNA损伤的保护作用[J]. 食品与发酵工业, 2004, 30(7): 55-58. DOI: 10.3321/j.issn:0253-990X.2004.07.013. doi: 10.3321/j.issn:0253-990X.2004.07.013
[8]	RICE-EVANS C, MILLER N, PAGANGA G. Antioxidant properties of phenolic compounds[J]. Trends in Plant Science, 1997, 2(4): 152-159. DOI: 10.1016/S1360-1385(97)01018-2. doi: 10.1016/S1360-1385(97)01018-2
[9]	ZHOU J R, MUKHERJEE P, GUGGER E T, et al. Inhibition of murine bladder tumorigenesis by soy isoflavones via alterations in the cell cycle, apoptosis, and angiogenesis[J]. Cancer Research, 1998, 58(22): 5231-5238. pmid: 9823337
[10]	FAN J L, ZHU W X, KANG H B, et al. Flavonoid constituents and antioxidant capacity in flowers of different Zhongyuan tree penoy cultivars[J]. Journal of Functional Foods, 2012, 4(1): 147-157. DOI: 10.1016/j.jff.2011.09.006. doi: 10.1016/j.jff.2011.09.006
[11]	高亚辉, 张淑霞, 万珊. 牡丹花中色素的提取及性能研究进展[J]. 食品工业科技, 2012, 33(9): 431-435. DOI: 10.13386/j.issn1002-0306.2012.09.043. doi: 10.13386/j.issn1002-0306.2012.09.043
[12]	XU S J, YANG L, ZENG X, et al. Characterization of compounds in the Chinese herbal drug Mu-Dan-Pi by liquid chromatography coupled to electrospray ionization mass spectrometry[J]. Rapid Communications in Mass Spectrometry, 2006, 20(22): 3275-3288. DOI: 10.1002/rcm.2717. doi: 10.1002/rcm.2717
[13]	FU Z W, LING Y, LI Z X, et al. HPLC-Q-TOF-MS/MS for analysis of major chemical constituents of Yinchen-Zhizi herb pair extract[J]. Biomedical Chromatography, 2014, 28(4): 475-485. DOI: 10.1002/bmc.3057. doi: 10.1002/bmc.3057 pmid: 24122818
[14]	向进乐, 赵胜娟, 马丽苹, 等. 可食牡丹鲜花酶法制汁及主成分HPLC-Q-TOF-MS/MS鉴定[J]. 食品与发酵工业, 2019, 45(18): 137-143. DOI: 10.13995/j.cnki.11-1802/ts.021093. doi: 10.13995/j.cnki.11-1802/ts.021093
[15]	赵康宏, 严思恩, 何英杰, 等. HPLC-Q-TOF-MS法分析百合中酚类化合物[J]. 中成药, 2019, 41(6): 1445-1450. DOI: 10.3969/j.issn.1001-1528.2019.06.051. doi: 10.3969/j.issn.1001-1528.2019.06.051
[16]	耿丹丹, 董琦, 谭亮, 等. HPLC-DAD-ESI/MSⁿ-DPPH在线筛选与鉴别丹参和康定鼠尾草中抗氧化活性成分[J]. 分析测试学报, 2015, 34(3): 314-320. DOI: 10.3969/j.issn.1004-4957.2015.03.010. doi: 10.3969/j.issn.1004-4957.2015.03.010
[17]	邢航, 张媛婷, 鲁雪峰, 等. 高效液相色谱-二苯基三硝基苯肼在线检测葡萄酒中抗氧化活性成分[J]. 中国实验方剂学杂志, 2013, 19(21): 127-131. DOI: 10.11653/syfj2013150127. doi: 10.11653/syfj2013150127
[18]	ZHU J F, YI X J, ZHANG J H, et al. Chemical profiling and antioxidant evaluation of Yangxinshi Tablet by HPLC-ESI-Q-TOF-MS/MS combined with DPPH assay[J]. Journal of Chromatography B, 2017, 1060: 262-271. DOI: 10.1016/j.jchromb.2017.06.022. doi: S1570-0232(17)30225-8 pmid: 28644981
[19]	WANG G, YAO S, ZHANG X X, et al. Rapid screening and structural characterization of antioxidants from the extract of Selaginella doederleinii Hieron with DPPH-UPLC-Q-TOF/MS method[J]. International Journal of Analytical Chemistry, 2015, 2015: 849769. DOI: 10.1155/2015/849769. doi: 10.1155/2015/849769
[20]	郑振佳, 张瑞凌, 张敏敏, 等. HPLC-DAD-Q-TOF-MS在线筛选鉴定牛蒡中的抗氧化成分[J]. 食品科学, 2019, 40(8): 175-179. DOI: 10.7506/spkx1002-6630-20180201-014. doi: 10.7506/spkx1002-6630-20180201-014
[21]	王文祥, 蒋小岗, 顾明, 等. 芍药的化学成分研究[J]. 天然产物研究与开发, 2000, 12(6): 37-39. DOI: 10.16333/j.1001-6880.2000.06.008. doi: 10.16333/j.1001-6880.2000.06.008
[22]	KAMIYA K, YOSHIOKA K, SAIKI Y, et al. Triterpenoids and flavonoids from Paeonia lactiflora[J]. Phytochemistry, 1997, 44(1): 141-144. DOI: 10.1016/S0031-9422(96)00518-3. doi: 10.1016/S0031-9422(96)00518-3
[23]	张友胜, 杨伟丽, 崔春. 显齿蛇葡萄化学成分的研究[J]. 中草药, 2003, 34(5): 21-22.
[24]	NONAKA G, NISHIOKA I. Tannins and related compounds. X. Rhubarb (2): isolation and structures of a glycerol gallate, gallic acid glucoside gallates, galloylglucoses and isolindleyin[J]. Chemical and Pharmaceutical Bulletin, 1983, 31(5): 1652-1658. DOI: 10.1248/cpb.31.1652. doi: 10.1248/cpb.31.1652
[25]	LI C H, DU H, WANG L S, et al. Flavonoid composition and antioxidant activity of tree peony (Paeonia section moutan) yellow flowers[J]. Journal of Agricultural and Food Chemistry, 2009, 57(18): 8496-8503. DOI: 10.1021/jf902103b. doi: 10.1021/jf902103b
[26]	ZERBACK R, BOKEL M, GEIGER H, et al. A kaempferol 3-glucosylgalactoside and further flavonoids from pollen of Petunia hybrida[J]. Phytochemistry, 1989, 28(3): 897-899. DOI: 10.1016/0031- 9422(89)80139-6.
[27]	闫慧娇, 王志伟, 赵恒强, 等. 菏泽牡丹花HPLC特征图谱研究及8种成分的测定[J]. 中草药, 2017, 48(9): 1866-1871. DOI: 10.7501/j.issn.0253-2670.2017.09.026. doi: 10.7501/j.issn.0253-2670.2017.09.026
[28]	MATSUURA N, IINUMA M, TANAKA T. Phylogenetic analysis in genus Euchresta based on secondary metabolites[J]. Biochemical Systemics and Ecology, 1994, 22(6): 621-629. DOI: 10.1016/0305- 1978(94)90075-2.
[29]	陈海生, 徐一新, 廖时萱, 等. 川赤芍化学成分的研究[J]. 第二军医大学学报, 1994, 15(1): 72-73. DOI: 10.16781/j.0258-879x.1994.01.024. doi: 10.16781/j.0258-879x
[30]	LIN H C, DING H Y, WU Y C. Two novel compounds from Paeonia suffruticosa[J]. Journal of Natural Products, 1998, 61(3): 343-346. DOI: 10.1021/np9704258. doi: 10.1021/np9704258

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序号	选择离子	实验值m/z	分子式	化合物推断结果	参考文献
1	[M-H]^-	331.055 4	C₁₃H₁₆O₁₀	1-没食子酸酰葡萄糖或6-没食子酸酰葡萄糖	[23-24]
2	[M-H]^-	169.007 7	C₇H₆O₅	没食子酸	[29]
3	[M-H]^-	495.124 5	C₂₃H₂₈O₁₂	氧化芍药苷	[27]
4	[M-H]^-	609.111 8	C₂₇H₃₀O₁₆	山奈酚-3,7-二-O-葡萄糖苷或山柰酚3-O-β-D-半乳糖(2→1)-β-D-葡萄糖苷	[25-26]
5	[M-H]^-	525.128 5	C₂₄H₃₀O₁₃	牡丹皮苷-E	[30]
6	[M-H]^-	197.033 5	C₉H₁₀O₅	没食子酸乙酯	[21]
7	[M-H]^-	639.115 6	C₂₈H₃₂O₁₇	异鼠李素-3,7-二-O-葡萄糖	[25]
8	[M-H]^-	653.129 3	—	未知
9	[M-H]^-	447.064 3	C₂₁H₂₀O₁₁	木犀草素-7-O-葡萄糖苷	[25]
10	[M-H]^-	469.021 2	C₂₉H₄₂O₅	11α,12α-epoxy-3β,23-dihydroxy-30-norolean-20(29)-en-28,13β-olide	[22]
11	[M-H]^-	447.064 6	C₂₁H₂₀O₁₁	山奈酚-3-O-β-D-吡喃葡萄糖苷	[27]
12	[M-H]^-	577.118 2	C₂₇H₃₀O₁₄	芹菜素-7-O-新橘皮糖苷或芹菜素-7-O-β-D-葡萄糖-4'-O-α-L-鼠李糖苷	[27-28]
13	[M-H]^-	431.070 1	C₂₁H₂₀O₁₀	芹菜素-7-O-β-D-吡喃葡糖苷	[27]
14	[M-H]^-	545.020 0	—	未知
15	[M-H]^-	349.03 26	—	未知

Identification of antioxidant components in peony flowers through on-line screening using high performance liquid chromatography-quadrupole time of flight mass spectrometer

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