HPLC-MS/MS Analysis of Water-Extracted Components of Loquat Leaves and Structural Identification of Terpenoids

LI Jiamei; XU Wei; ZHANG Xue; SHAO Baiqi; XIE Hongyao; WU Fan; MA Zhiyu; CHEN Hua

doi:10.13386/j.issn1002-0306.2021040180

Volume 43 Issue 1

Dec. 2021

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Science and Technology of Food Industry > 2022 > 43(1): 295-303. > DOI: 10.13386/j.issn1002-0306.2021040180

LI Jiamei, XU Wei, ZHANG Xue, et al. HPLC-MS/MS Analysis of Water-Extracted Components of Loquat Leaves and Structural Identification of Terpenoids[J]. Science and Technology of Food Industry, 2022, 43(1): 295−303. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021040180.

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HPLC-MS/MS Analysis of Water-Extracted Components of Loquat Leaves and Structural Identification of Terpenoids

1.
School of Food Engineering, Harbin University of Commerce, Harbin 150076, China
2.
Nantong Tianlai Village Agricultural Science and Technology Development Co., Ltd., Haimen 226100, China

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Received Date: April 25, 2021
Available Online: November 02, 2021

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Abstract

Abstract

Using high performance liquid chromatography-mass spectrometry(HPLC-MS/MS) technology, the components in the water extract of loquat leaves were analyzed, and the terpenoids were analyzed. Using a C₁₈ column (2.1 mm×100 mm, 1.8 μm), using water +0.1% formic acid solution as mobile phase gradient elution, using ESI ion source, collecting mass spectrometry data in positive and negative ion modes, a total of 120 compounds were detected ; Including 18 kinds of terpenoids with a total relative content of 1452.693 μg/mL; 24 kinds of flavonoids with a total relative content of 10378.081 μg/mL; 18 kinds of phenolic compounds with a total relative content of 36967.955 μg/mL; 5 kinds of coumarins compounds with a total relative content of 214.778 μg/mL; The structures of 18 terpenoids were further identified, including 6 ursane type, 7 oleanane type, 3 sesquiterpenes, and 1 diterpenoid. And a special iridoid glycosides; Roburic acid, ginkgolide B, prespatane, shanzhiside methyl ester, icariside B_5, quillaic acid, asiatic acid, 18β-glycyrrhetinic acid were no report in the previous active substances of loquat leaves. This article provides a reference for the research on the water-extracted components of loquat leaves.
- loquat leaves,
- water-extracted components,
- HPLC-MS/MS,
- terpenoids,
- structure identification

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References

[1]	魏鑫. 枇杷叶的三萜酸类化学成分研究[D]. 昆明: 云南中医学院, 2014. WEI X. The study on chemical constituents of triterpene acids in loquat leaves[D]. Kunming: Yunnan College of Traditional Chinese Medicine, 2014.
[2]	孙燕丽, 胡巧云, 谢茹胜. 枇杷叶的化学成分及药理作用研究进展[J]. 海峡药学,2019,31(8):57−59. [SUN Y L, HU Q Y, XIE R S. Research progress on chemical constituents and pharmacological action of loquat leaves[J]. Strait Pharmaceutical Journal,2019,31(8):57−59. doi: 10.3969/j.issn.1006-3765.2019.08.019
[3]	ASHOUR M, WINK M, GERSHENZON J. Biochemistryofterpenoids: Monoterpenes, sesquiterpenes and diterpenes[M]//Wink M. Biochemistry of Plant Secondary Metabolism. 2rd ed. Wiley Blackwell, 2010: 258-303.
[4]	陈欢, 陈光, 任红梅, 等. 枇杷叶中三萜类成分的研究[J]. 北京化工大学学报(自然科学版),2012,39(3):40−45. [CHEN H, CHEN G, REN H M, et al. Isolation of the triterpenes from Eriobotrya japonica leaves[J]. Journal of Beijing University of Chemical Technology (Natural Science Edition),2012,39(3):40−45.
[5]	吕寒, 陈剑, 李维林, 等. 枇杷叶中三萜类化学成分的研究[J]. 中药材,2008,295(9):1351−1354. [LV H, CHEN J, LI W L, et al. Studies on the triterpenes from loquat leaf (Eriobotrya japonica)[J]. Journal of Chinese Medicinal Materials,2008,295(9):1351−1354. doi: 10.3321/j.issn:1001-4454.2008.09.020
[6]	国家药典委员会. 中华人民共和国药典[M]. 北京: 化学工业出版社, 2015. National Pharmacopoeia Commission. The Pharmacopoeia of the People’s Republic of China[M]. Beijing: Chemical Industry Press, 2015.
[7]	叶广亿, 李书渊, 陈艳芬, 等. 枇杷叶不同提取物的止咳化痰平喘作用比较研究[J]. 中药药理与临床,2013,29(2):100−102. [YE G Y, LI S Y, CHEN Y F, et al. Comparative study of different extracts of loquat leaf in antitussive an expectorant and antiasthmatic effects[J]. Pharmacology and Clinics of Chinese Materia Medica,2013,29(2):100−102.
[8]	张娜, 吴绍康, 沈先荣, 等. 枇杷叶水提物祛痰止咳及抗炎作用研究[J]. 中华中医药学刊,2014,32(9):2175−2177. [ZHANG N, WU S K, SHEN X R, et al. Study on expectorant, antitussive and anti-inflammatory effects of aque extract of eriobotrya japonica leaves[J]. Chinese Archives of Traditional Chinese Medicine,2014,32(9):2175−2177.
[9]	WU Y X, JIAN T Y, LV H , et al. Antitussive and expectorant properties of growing and fallen leaves of loquat (Eriobotrya japonica)[J]. Revista Brasileira De Farmacognosia, 2018: S0102695X17305264.
[10]	黄家晋, 黄智霖, 陈鸿庚, 等. UPLC-Q-TOF-MS/MS分析凉粉草多酚组分的化学成分[J/OL]. 天然产物研究与开发: 1−18 [2021-04-15]. http://kns.cnki.net/kcms/detail/51.1335.Q.20210318.1727.009.html. HUANG J J, HUANG Z L, CHEN H G, et al. Analysis of polyphenols from Mesona chinensis by UPLC-Q-TOF-MS/MS[J/OL]. Natural Product Research and Development: 1−18 [2021-04-15]. http://kns.cnki.net/kcms/detail/51.1335.Q.20210318.1727.009.html.
[11]	徐伟, 李佳美, 马智宇, 等. 微波耦合漆酶法水提枇杷叶浸膏工艺的响应面优化[J]. 食品工业科技,2021,42(6):208−213,240. [XU W, LI J M, MA Z Y, et al. Response surface optimization of water extraction technology of loquat leaves extract by microwave-coupled laccase[J]. Food Industry Technology,2021,42(6):208−213,240.
[12]	霍宇航, 李檐堂, 刘丽丽, 等. 基于主要功能成分的6个品种枇杷叶分析评价[J]. 食品科学,2019,40(24):234−240. [HUO Y H, LI Z T, LIU L L, et al. Analysis and evaluation of main functional components of loquat leave different positions from 6 varieties[J]. Food Science,2019,40(24):234−240. doi: 10.7506/spkx1002-6630-20190109-116
[13]	袁园, 张燕军, 张孝琴. 白芷中香豆素类成分的提取工艺研究[J]. 山东化工,2016,45(10):29−31. [YUAN Y, ZHANG Y J, ZHANG X Q. Study on extraction and stability of coumarins in angelica dahurica[J]. Shandong Chemical Industry,2016,45(10):29−31. doi: 10.3969/j.issn.1008-021X.2016.10.009
[14]	王婷婷, 安叡, 梁琨, 等. 基于UPLC-LTQ-Orbitrap高分辨质谱的葛根芩连汤的化学成分分析[J]. 中草药,2020,51(6):1498−1507. [WANG T T, AN R, LIANG K, et al. Chemical constituent analysis of Gegen Qinlian decoction based on UPLC-LTQ-Orbitrap-MS[J]. Chinese Traditional and Herbal Drugs,2020,51(6):1498−1507.
[15]	BUCKOW R, KASTELL A, TEREFE N S, et al. Pressure and temperature effects on degradation kinetics and storage stability of total anthocyanins in blueberryjuice[J]. Journal of Agriculture and Food Chemistry,2010,58(18):10076−10084. doi: 10.1021/jf1015347
[16]	YANG L, LIU R H, HE J W. Rapid analysis of the chemical compositions in Semiliquidambar cathayensis roots by ultra high-performance liquid chromatography and quadrupole time-of-flight tandem mass spectrometry[J]. Molecules,2019,24(22):4098. doi: 10.3390/molecules24224098
[17]	张聪, 刘建勋, 孙明谦, 等. 3种银杏内酯成分的质谱裂解途径研究[J]. 中国中药杂志,2018,43(20):4093−4096. [ZHANG C, LIU J X, SUN M Q, et al. Study on fragmentation pathways of three ginkgolides by mass spectrometry[J]. China Journal of Chinese Materia Medica,2018,43(20):4093−4096.
[18]	李泮霖, 黄昕, 云莎, 等. 基于UFLC-Triple TOF-MS/MS技术的银杏叶提取物注射液化学物质基础研究[J]. 中南药学,2017,15(5):573−579. [LI P L, HUANG X, YUN S, et al. Chemical material basis of extract of Ginkgo biloba leaves injection by ultrafast liquid chromatography/triple time-of-flight tandem mass spectrometry[J]. Central South Pharmacy,2017,15(5):573−579.
[19]	NABETA K, YAMAMOTO M, KOSHINO H, et al. Absolute configuration of kelsoene and prepatane[J]. Bioence Biotechnology and Biochemistry, 1999, 63(10): 1772−1776.
[20]	陈方超, 高守红, 王志鹏, 等. 基于UHPLC-Q-TOF-MS/MS技术鉴定藤梨根的化学成分[J]. 中国药房,2020,31(14):1725−1731. [CHEN F C, GAO S H, WANG Z P, et al. Identification of chemical components in Actinidia chinensis root by UHPLC-Q-TOF-MS/MS[J]. China Pharmacy,2020,31(14):1725−1731. doi: 10.6039/j.issn.1001-0408.2020.14.12
[21]	莫颖华, 冯白茹, 刘道军. 枇杷叶中熊果酸和齐墩果酸的提取工艺研究[J]. 汕头大学医学院学报,2017,30(3):137−138,171. [MO Y H, FENG B R, LIU D J. The study on the extraction process of ursolic acid and oleanolic acid in loquat leaves[J]. Journal of Shantou University Medical College,2017,30(3):137−138,171.
[22]	李伊莎, 夏彬彬, 徐唯哲, 等. 积雪草酸提取工艺及其在70种中药中质量分数的测定[J]. 首都医科大学学报,2013,34(5):766−769. [LI Y S, XIA B B, XU W Z, et al. The extraction process of asiatic acid and the determination of its mass fraction in 70 kinds of traditional chinese medicine[J]. Journal of Capital Medical University,2013,34(5):766−769. doi: 10.3969/j.issn.1006-7795.2013.05.026
[23]	李季, 崔兵兵, 曲远均. 积雪草药理活性及新制剂研究进展[J]. 辽宁中医药大学学报,2020,22(12):200−204. [LI J, CUI B B, QU Y J. Research progress in chemical constituents, pharmacological activities a new preparations of Centella asiatica[J]. Journal of Liaoning University of Traditional Chinese Medicine,2020,22(12):200−204.
[24]	PELLATI D, FIORE C, ARMANINI D, et al. In vitro effects of glycyrrhetinic acid on the growth of clinical isolates of Candida albicans[J]. Phytotherapy Research,2010,23(4):572−574.
[25]	LI Z, DU Y, YUAN Y, et al. Integrated quality evaluation strategy for multi-species resourced herb medicine of Qinjiao by metabolomics analysis and genetic comparation[J]. Chinese Medicine,2020:15.
[26]	WANG C C, CAI Z C, SHI J J, et al. Comparative metabolite profiling of wild and cultivated licorice based on ultra-fast liquid chromatography coupled with triple quadrupole-time of flight tandem mass spectrometry[J]. Chemical and Pharmaceutical Bulletin,2019,67(10):1104−1115. doi: 10.1248/cpb.c19-00423
[27]	聂安政, 林志健, 王雨, 等. 秦艽化学成分及药理作用研究进展[J]. 中草药,2017,48(3):597−608. [NIE A Z, LIN Z J, WANG Y, et al. Advance in studies on chemical constituents of Gentianae macrophylla Radix and their pharmacological effects[J]. Chinese Traditional and Herbal Drugs,2017,48(3):597−608.
[28]	陈玉芬. 栎瘿酸的抗炎作用及机制研究[D]. 天津: 天津医科大学, 2017. CHEN Y F. The anti-inflammatory effect of roburic acid and the related mechanism [D]. Tianjin: Tianjin Medical University, 2017.
[29]	SELEMANI M A, KAZINGIZI L F, MANZOMBE E, et al. Phytochemical characterization and in vitro antibacterial activity of Xeroderris stuhlmannii(Taub.) Mendonca & EP Sousa bark extracts[J]. South African Journal of Botany,2021,142:344−351. doi: 10.1016/j.sajb.2021.07.006

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