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

doi:10.5246/jcps.2022.07.044

Abstract

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:

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.

Figures/Tables 6

References 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.