UPLC-Q-TOF-MS/MS分析海南竹叶蒲桃的化学成分

doi:10.5246/jcps.2022.07.044

中国药学(英文版) ›› 2022, Vol. 31 ›› Issue (7): 507-516.DOI: 10.5246/jcps.2022.07.044

UPLC-Q-TOF-MS/MS分析海南竹叶蒲桃的化学成分

庞朝海¹^,²^,³^,⁴^,^*(), 许园⁵^,^*(), 马雄辉¹^,²^,³^,⁴, 吴雨薇¹^,²^,³^,⁴, 黎舒怀¹^,²^,³^,⁴^,^*(), 李萍萍¹^,²^,³^,⁴, 张振山¹^,²^,³^,⁴

1. 中国热带农业科学院分析测试中心, 海南海口 571101
2. 农业农村部亚热带果品蔬菜质量安全控制重点实验室, 海南海口 571101
3. 海南省热带果蔬产品质量安全重点实验室, 海南海口 571101
4. 国家市场监管重点实验室(热带果蔬质量与安全), 海南海口 571101
5. 海南医科大学药学院热带转化医学教育部重点实验室, 海南海口 571199

收稿日期:2022-03-17 修回日期:2022-04-21 接受日期:2022-05-13 出版日期:2022-07-31 发布日期:2022-07-31
通讯作者: 庞朝海, 许园, 黎舒怀
作者简介:
+ Tel.: +86-898-66895008, E-mail: 18389859589@163.com
+ E-mail: xuyuangdpu@163.com
+ E-mail: happylishuhuai@163.com
基金资助:
Natural Science Foundation of Hainan Province (Grant No. 320QN302), the Central Public-interest Scientific Institution Basal Research Fund for the Chinese Academy of Tropical Agricultural Sciences (Grant No. 1251632022005), the Key Laboratory of Tropical Fruits and Vegetables Quality and Safety for State Market Regulation (Grant No. ZX-2022002) and Open Fund of Hainan Provincial Key Laboratory of Quality and Safety for Tropical Fruits and Vegetables (Grant No. KFKT2021002).

Chemical constituents of Hainan Syzygium myrsinifolium (Hance) Merr. et Perry based on ultra-high performance liquid chromatography-time-of-flight tandem mass spectrometry

Chaohai Pang¹^,²^,³^,⁴^,^*(), Yuan Xu⁵^,^*(), Xionghui Ma¹^,²^,³^,⁴, Yuwei Wu¹^,²^,³^,⁴, Shuhuai Li¹^,²^,³^,⁴^,^*(), Pingping Li¹^,²^,³^,⁴, Zhenshan Zhang¹^,²^,³^,⁴

1 Analysis and Test Center, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
2 Key Laboratory of Quality and Safety Control for Subtropical Fruit and Vegetable, Ministry of Agriculture and Rural Affairs, Haikou 571101, China
3 Hainan Provincial Key Laboratory of Quality and Safety for Tropical Fruits and Vegetables, Haikou 571101, China
4 Key Laboratory of Tropical Fruits and Vegetables Quality and Safety for State Market Regulation, Haikou 571101, China
5 Key Laboratory of Tropical Translational Medicine of Ministry of Education, School of Pharmacy, Hainan Medical University, Haikou 571199, China

Received:2022-03-17 Revised:2022-04-21 Accepted:2022-05-13 Online:2022-07-31 Published:2022-07-31
Contact: Chaohai Pang, Yuan Xu, Shuhuai Li

摘要/Abstract

摘要：

竹叶蒲桃是海南岛特有的植物资源, 目前关于它化学成分的研究报道很少。本研究采用超高效液相色谱-四极杆-飞行时间串联质谱联用技术(UPLC-Q-TOF-MS/MS)鉴定竹叶蒲桃叶片中的主要化学成分。通过高分辨质谱数据分析、参考文献数据及对照品确认, 对竹叶蒲桃的化学成分进行快速的定性分析, 鉴定并推断出包括有机酸、酚酸、黄酮和香豆素在内的20种化合物, 并对其裂解规律进行分析。其中4个有机酸、8个酚酸、7个黄酮和1个香豆素类化合物首次在竹叶蒲桃叶片中报道。本研究建立的方法能快速、准确地对竹叶蒲桃叶片中部分成分进行鉴定解析, 为竹叶蒲桃植物资源的成分研究和开发利用提供了实验依据。

关键词: 竹叶蒲桃, UPLC-Q-TOF-MS/MS, 鉴定

Abstract:

Syzygium myrsinifolium (Hance) Merr. et Perry is a unique plant resource on Hainan Island, and there are few reports on its chemical constituents. In the present study, we identified the major chemical constituents in the leaves of Syzygium myrsinifolium (Hance) Merr. et Perry using ultra-high performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-Q-TOF-MS/MS). The chemical constituents in Syzygium myrsinifolium (Hance) Merr. et Perry were identified rapidly based on the accurate relative molecular mass and combined with literature data and reference substances. A total of 20 compounds, including organic acids, phenolic acids, and flavonoids, were identified. Among these 20 compounds, four organic acids, eight phenolic acids, seven flavonoids, and one coumarin were reported from the leaves of Syzygium myrsinifolium (Hance) Merr. et Perry for the first time. The established method was rapid and accurate, and some chemical constituents in the leaves of Syzygium myrsinifolium (Hance) Merr. et Perry have been identified. This research provided an experimental reference for the study of the constituents and utilization of Syzygium myrsinifolium (Hance) Merr. et Perry.

Key words: Syzygium myrsinifolium (Hance) Merr. et Perry, UPLC-Q-TOF-MS/MS, Identification

Supporting:

庞朝海, 许园, 马雄辉, 吴雨薇, 黎舒怀, 李萍萍, 张振山. UPLC-Q-TOF-MS/MS分析海南竹叶蒲桃的化学成分[J]. 中国药学(英文版), 2022, 31(7): 507-516.

Chaohai Pang, Yuan Xu, Xionghui Ma, Yuwei Wu, Shuhuai Li, Pingping Li, Zhenshan Zhang. Chemical constituents of Hainan Syzygium myrsinifolium (Hance) Merr. et Perry based on ultra-high performance liquid chromatography-time-of-flight tandem mass spectrometry[J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(7): 507-516.

图/表 6

Figure 1. TIC chromatograms of Syzygium myrsinifolium (Hance) Merr. et Perry extract in negative ion mode.

Figure 2. TIC chromatograms of 14 reference compounds in negative ion mode.

Table 1. Compounds identified in Syzygium myrsinifolium (Hance) Merr. et Perry by UPLC-ESI-Q-TOF-MS.

Figure 3. Fragmentation pathways of catechin.

Figure 4. Primary fragmentation pathways of quercetin.

Figure 5. Primary fragmentation pathways of quercetin-3-O-rhamnopyranoside.

参考文献 29

[1]	Chang, C.W.; Wu, T.S.; Hsieh, Y.S.; Kuo, S.C.; Chao, P.D.L. Terpenoids of syzygium formosanum. J. Nat. Prod. 1999, 62, 327–328
[2]	Benherlal, P.S.; Arumughan, C. Chemical composition and in vitro antioxidant studies on Syzygium cumini fruit. J. Sci. Food Agric. 2007, 87, 2560–2569.
[3]	Jain, A.; Sharma, S.; Goyal, M.; Dubey, S.; Jain, S.; Sahu, J.; Sharma, A.; Kaushik, A. Anti-inflammatory activity of Syzygium cumini leaves. Int. J. Phytomedicine. 2010, 2, 124–126.
[4]	Lee, H.S.; Hwang, I.H.; Kim, J.A.; Choi, J.Y.; Jang, T.S.; Osada, H.; Ahn, J.S.; Na, M.; Lee, S.H. ChemInform abstract: isolation of protein tyrosine phosphatase 1B inhibitory constituents from the sclerotia of polyporus umbellatus fries. ChemInform. 2011, 42.
[5]	Djoukeng, J.D.; Abou-Mansour, E.; Tabacchi, R.; Tapondjou, A.L.; Bouda, H.; Lontsi, D. Antibacterial triterpenes from syzygium guineense (Myrtaceae). J. Ethnopharmacol. 2005, 101, 283–286.
[6]	Li, G.Q.; Zhang, Y.B.; Wu, P.; Chen, N.H.; Wu, Z.N.; Yang, L.; Qiu, R.X.; Wang, G.C.; Li, Y.L. New phloroglucinol derivatives from the fruit tree syzygium jambos and their cytotoxic and antioxidant activities. J. Agric. Food Chem. 2015, 63, 10257–10262.
[7]	Subarnas, A.; Diantini, A.; Abdulah, R.; Zuhrotun, A.; Hadisaputri, Y.E.; Puspitasari, I.M.; Yamazaki, C.; Kuwano, H.; Koyama, H. Apoptosis induced in MCF-7 human breast cancer cells by 2',4'-dihydroxy-6-methoxy-3,5-dimethylchalcone isolated from Eugenia aquea Burm f. leaves. Oncol. Lett. 2015, 9, 2303–2306.
[8]	Nguyen, T.L.; Rusten, A.; Bugge, M.S.; Malterud, K.E.; Diallo, D.; Paulsen, B.S.; Wangensteen, H. Flavonoids, gallotannins and ellagitannins in Syzygium guineense and the traditional use among Malian healers. J. Ethnopharmacol. 2016, 192, 450–458.
[9]	Hu, Y.K.; Wang, L.; Li, Y.Y.; Li, M.J.; Xu, W.; Zhao, Y.; Li, F.; Zhao, Y. Five new triterpenoids from syzygium samarangense (bl.) merr. et perry. Phytochem. Lett. 2018, 25, 147–151.
[10]	Yang, J.; Su, J.C.; Lei, X.P.; Huang, X.J.; Zhang, D.M.; Ye, W.C.; Wang, Y. Acylphloroglucinol derivatives from the leaves of Syzygium samarangense and their cytotoxic activities. Fitoterapia. 2018, 129, 1–6.
[11]	Sobeh, M.; Petruk, G.; Osman, S.; El Raey, M.A.; Imbimbo, P.; Monti, D.M.; Wink, M. Isolation of myricitrin and 3,5-di-O-methyl gossypetin from syzygium samarangense and evaluation of their involvement in protecting keratinocytes against oxidative stress via activation of the nrf-2 pathway. Molecules. 2019, 24, 1839.
[12]	Ling, Y.; Zhang, Q.; Zhong, W.J.; Chen, M.P.; Gong, H.N.; He, S.S.; Liang, R.; Lv, J.; Song, L.Y. Rapid identification and analysis of the major chemical constituents from the fruits of Sapindus mukorossi by HPLC-ESI-QTOF-MS/MS. Nat. Prod. Res. 2019, 34, 2144–2150.
[13]	Shen, B.B.; Zhou, R.R.; Yang, Y.P.; Li, J.Y.; Liang, X.J.; Chen, L.; Huang, L.Q.; Zhang, S.H. Antimicrobial activity-guided identification of compounds from the deciduous leaves of Malus doumeri by HPLC-ESI-QTOF-MS/MS. Nat. Prod. Res. 2019, 33, 2515–2520.
[14]	Sahu, N.; Meena, S.; Shukla, V.; Chaturvedi, P.; Kumar, B.; Datta, D.; Arya, K.R. Extraction, fractionation and re-fractionation of Artemisia nilagirica for anticancer activity and HPLC-ESI-QTOF-MS/MS determination. J. Ethnopharmacol. 2018, 213, 72–80.
[15]	Zhang, J.N.; Zhao, M.M.; Su, G.W.; Lin, L.Z. Identification and taste characteristics of novel umami and umami-enhancing peptides separated from peanut protein isolate hydrolysate by consecutive chromatography and UPLC-ESI-QTOF-MS/MS. Food Chem. 2019, 278, 674–682.
[16]	Guo, R.Z.; Liu, X.G.; Gao, W.; Dong, X.; Fanali, S.; Li, P.; Yang, H. A strategy for screening antioxidants in Ginkgo biloba extract by comprehensive two-dimensional ultra high performance liquid chromatography. J. Chromatogr. A. 2015, 1422, 147–154.
[17]	Bylund, D.; Norström, S.H.; Essén, S.A.; Lundström, U.S. Analysis of low molecular mass organic acids in natural waters by ion exclusion chromatography tandem mass spectrometry. J. Chromatogr. A. 2007, 1176, 89–93.
[18]	Han, J.; Ye, M.; Xu, M.; Qiao, X.; Chen, H.B.; Wang, B.R.; Zheng, J.H.; Guo, D.A. Comparison of phenolic compounds of rhubarbs in the section deserticola with Rheum palmatum by HPLC-DAD-ESI-MSn. Planta Med. 2008, 74, 873–879.
[19]	Zhuang, B.; Bi, Z.M.; Wang, Z.Y.; Duan, L.; Lai, C.J.S.; Liu, E.H. Chemical profiling and quantitation of bioactive compounds in platycladi cacumen by UPLC-Q-TOF-MS/MS and UPLC-DAD. J. Pharm. Biomed. Anal. 2018, 154, 207–215.
[20]	Fischer, U.A.; Carle, R.; Kammerer, D.R. Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD-ESI/MSn. Food Chem. 2011, 127, 807–821.
[21]	Ky, I.; Le Floch, A.; Zeng, L.; Pechamat, L.; Jourdes, M.; Teissedre, P.L. Tannins. Encyclopedia of Food and Health. Elsevier Reference Collection in Food Science. 2016, 247–255.
[22]	Miketova, P.; Schram, K.H.; Whitney, J.; Li, M.; Huang, R.; Kerns, E.; Valcic, S.; Timmermann, B.N.; Rourick, R.; Klohr, S. Tandem mass spectrometry studies of green tea catechins. Identification of three minor components in the polyphenolic extract of green tea. J. Mass Spectrom. 2000, 35, 860–869.
[23]	Liu, G.Q.; Dong, J.; Wang, H.; Wan, L.R.; Duan, Y.S.; Chen, S.Z. ESI fragmentation studies of four tea catechins. Chem. J. Chin. Univ. 2009, 30, 1566–1570.
[24]	Pilepić, K.H.; Yang, Z.L.; Chen, J.; Chen, X.Q.; Wang, Y.; Zhao, J.; Mihaljević, S.; Li, S.P. Flavonoids in natural and tissue cultured materials of Epimedium alpinum identified by using UHPLC-Q-TOF-MS/MS. Int. J. Mass Spectrom. 2018, 434, 222–232.
[25]	Ji, Z.C.; Jiang, Y.; Lin, H.; Ren, W.B.; Lin, L.; Guo, H.Y.; Huang, J.; Li, Y.Y. Global identification and quantitative analysis of representative components of Xin-Nao-Kang Capsule, a traditional Chinese medicinal formula, by UHPLC-Q-TOF-MS and UHPLC-TQ-MS. J. Pharm. Biomed. Anal. 2021, 198, 114002.
[26]	Yong, L.; Lin, Y.X.; Zhou, Y.Y.; Xie, J. Analysis active ingredients in Chinese waxberry by UPLC-ESI-Q-TOF/MS. Food Res. Dev. 2018, 39, 123–127, 148.
[27]	Zheng, Y.Y.; Zeng, X.; Guan, M.Y.; Xie, S.T.; Peng, W.; Su, W.W. UHPLC-Q-TOF-MS/MS-based metabolite profiling of ganpu tea in rat urine and feces. Nat. Prod. Commun. 2022, 17, 1934578X2210846.
[28]	Diwu, W.B.; Tan, N.N.; Wang, X.L.; Wang, L. Analysis of flavonoids from Acer truncatum Bunge leaves and study on the fragmentation patterns in electrospray ionization mass spectrometry. J. Baoji Univ. Arts Sci. Nat. Sci. Ed. 2020, 40, 25–33.
[29]	Yang, L.R.; Meng, X.; Yu, X.J.; Kuang, H.X. Simultaneous determination of anemoside B4, phellodendrine, berberine, palmatine, obakunone, esculin, esculetin in rat plasma by UPLC-ESI-MS/MS and its application to a comparative pharmacokinetic study in normal and ulcerative colitis rats. J. Pharm. Biomed. Anal. 2017, 134, 43–52.

UPLC-Q-TOF-MS/MS分析海南竹叶蒲桃的化学成分

Chemical constituents of Hainan Syzygium myrsinifolium (Hance) Merr. et Perry based on ultra-high performance liquid chromatography-time-of-flight tandem mass spectrometry

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

图/表 6

参考文献 29

相关文章 15

编辑推荐

Metrics

本文评价

[1]	谭静玲, 陆娟, 郑国华. 酸藤子化学成分的研究[J]. 中国药学(英文版), 2022, 31(4): 264-269.
[2]	金祥飞, 程闽玥, 钟斯卉, 徐云根, 沈卫阳. 棕榈酸曲安奈德中未知杂质的鉴定[J]. 中国药学(英文版), 2022, 31(4): 270-278.
[3]	吴桐, 杜肖, 王建农, 刘良裕, 杨宇珂. 白英中两个新糖苷生物碱[J]. 中国药学(英文版), 2021, 30(6): 518-523.
[4]	席彩彩, 徐云玲, 冯康, 吴人照, 骆世洪. 马槟榔种子的化学成分研究[J]. 中国药学(英文版), 2021, 30(11): 924-931.
[5]	徐云玲, 王昱霁, 江石平, 蔡婷婷, 王楠楠, 刘霞, 朱婉萍. 北五味子化学成分的研究[J]. 中国药学(英文版), 2020, 29(7): 480-486.
[6]	赵中振, 陈虎彪, 郭平, 梁之桃, 白效龙, 黄丽丽, 刘靖. 中药传统鉴定技术的传承与本草文化推广[J]. 中国药学(英文版), 2020, 29(12): 908-914.
[7]	李倩, 孙淑仃, 王梅英, 李彩凤, 袁丹, 付宏征. 草乌的化学成分及镇痛活性研究[J]. 中国药学(英文版), 2018, 27(12): 855-863.
[8]	程丽, 陈静, 谭艳, 王富乾, 汪选斌, 薛永波, 郝新才, 张勇慧. 血见愁植物化学成分研究[J]. 中国药学(英文版), 2018, 27(10): 719-723.
[9]	陈新涛, 兰鸿, 郑涛, 董永成, 梁俊, 陈黎. 植物内生真菌团青霉的化学成分研究[J]. 中国药学(英文版), 2017, 26(2): 156-160.
[10]	陈晨, 罗观堤, 胡荣, 付宏征. 马甲子的化学成分研究[J]. 中国药学(英文版), 2016, 25(2): 111-115.
[11]	刘俊丽, 郝艳平, 王建斌, 窦文彤, 陈晨, 郭妍, 袁丹, 付宏征. 鸡骨香的化学成分研究[J]. 中国药学(英文版), 2016, 25(11): 826-831.
[12]	彭希凤, 吴琼, 高纯, 盖春艳, 袁丹, 付宏征. 酸浆果实和宿萼的化学成分研究[J]. 中国药学(英文版), 2015, 24(9): 600-606.
[13]	谢雁景, 刘子光, 高雅宁, 王秀伶, 郝庆红, 于秀梅. 一株新分离鸡肠道厌氧细菌将染料木素转化为左旋-5羟基-雌马酚[J]. 中国药学(英文版), 2015, 24(7): 442-448.
[14]	孟作环, 乔莉, 王宗权, 马振嗣, 贾继明, 常青鲜, 李文列. 南葶苈子化学成分的UPLC/Q-TOF-MS/MS分析[J]. 中国药学(英文版), 2015, 24(5): 303-309.
[15]	胡艳维, 王璇, 谢可辉, 涂光忠, 袁丹, 付宏征. 吉祥草中一个新的呋甾皂苷[J]. 中国药学(英文版), 2014, 23(3): 177-181.