Food and Fermentation Industries >

2024 , Vol. 50 >Issue 12: 299 - 307

DOI: https://doi.org/10.13995/j.cnki.11-1802/ts.037257

Differences analysis of terpenoid metabolites in different organs of Hemerocallis citrina based on ultra performance liquid chromatography-tandem mass spectrometry

  • LYU Hongrui ,
  • WU Zhenzhen ,
  • HONG Shasha ,
  • JIA Huimin ,
  • GUO Shang
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  • (Shanxi Institute for Functional Food, Shanxi Agricultural University, Taiyuan 030031, China)

Received date: 2023-09-04

  Revised date: 2023-10-27

  Online published: 2024-07-11

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Abstract

Hemerocallis citrina is an edible and medicinal homologous plant, which is rich in many nutrients and bioactive components.Terpenoids are a kind of important bioactive component in H.citrina.To understand the dominant terpenoid metabolites in H.citrina roots, stems, leaves, and flowers, respectively, this study analyzed the terpenoid metabolites in these 4 organs based on the ultra performance liquid chromatography-tandem mass spectrometry technology of widely targeted metabolomics.A total of 43 terpenoids were identified, including 7 kinds of monoterpenoids (16.2%), 18 kinds of ditepenoids (41.9%), 16 kinds of triterpene (37.2%), and 2 kinds of triterpene saponin (4.7%).Principal component analysis and clustering analysis indicated that the mass spectrometry data were reliable, and the accumulation of terpenoids in different organs was significantly different.The dominant terpenoid metabolites in roots included isopimaradieneone, pimaradienone, abietic acid, scutebarbolide C, and isopimaric acid.The dominant terpenoid metabolites in stems included 3,9-dihydroxy-13(14)-labden-16,15-olide and 9,19-cyclolanost-24-en-3-ol (cycloartenol).The dominant terpenoid metabolites in leaves included viteagnusin A and ent-3β-acetoxyisopimar-15-8β-ol.The dominant terpenoid metabolites in flowers included vitexilactone and 7-O-coumaroyl-loganic acid.This study listed the relative contents of all terpenoids in roots, stems, leaves, and flowers of H.citrina in detail, which provided the foundation for further investigation of the different usages of various plant organs of H.citrina, and the information is important for the food industry and medical treatment.

Key words： Hemerocallis citrina; organs; terpenoid; ultra performance liquid chromatography-tandem mass spectrometry; widely targeted metabolomics

Cite this article

LYU Hongrui , WU Zhenzhen , HONG Shasha , JIA Huimin , GUO Shang . Differences analysis of terpenoid metabolites in different organs of Hemerocallis citrina based on ultra performance liquid chromatography-tandem mass spectrometry[J]. Food and Fermentation Industries, 2024 , 50(12) : 299 -307 . DOI: 10.13995/j.cnki.11-1802/ts.037257

References

[1] 刘佩冶, 李可昕, 张超凡, 等.黄花菜生物活性成分及功能研究进展[J].食品与发酵工业, 2022, 48(12):330-336.
LIU P Y, LI K X, ZHANG C F, et al.Research progress on bioactive components and functions of daylily[J].Food and Fermentation Industries, 2022, 48(12):330-336.
[2] 张玉梅. 黄花菜的栽培技术与采收加工[J].现代农业, 2015,(5):61.
ZHANG Y M.Cultivation techniques and harvesting and processing of daylily[J].Modern Agriculture, 2015, (5):61.
[3] 赵瑛瑛. 不同产地黄花菜中的营养成分的差别及不同加工过程的影响[J].现代养生(下半月版), 2019(7):38-39.
ZHAO Y Y.Difference of nutritional components in daylily from different producing areas and the influence of different processing processes[J].Health Protection and Promotion, 2019(7):38-39.
[4] 李明玥, 刘宏艳, 肖静, 等.黄花菜的活性成分、生物活性及加工技术研究进展[J].食品工业科技, 2022, 43(19):427-435.
LI M Y, LIU H Y, XIAO J, et al.Research progress on bioactive components, biological activities, and processing technology of daylily (Hemerocallis citrina baroni)[J].Science and Technology of Food Industry, 2022, 43(19):427-435.
[5] 李佳美, 徐伟, 张雪, 等.基于HPLC-MS/MS对枇杷叶水提组分分析及萜类物质的结构鉴定[J].食品工业科技, 2022, 43(1):295-303.
LI J M, XU W, ZHANG X, 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.
[6] NAGEGOWDA D A, GUPTA P.Advances in biosynthesis, regulation, and metabolic engineering of plant specialized terpenoids[J].Plant Science, 2020, 294:110457.
[7] TAI C Y, CHEN B H.Analysis and stability of carotenoids in the flowers of daylily (Hemerocallis disticha) as affected by various treatments[J].Journal of Agricultural and Food Chemistry, 2000, 48(12):5962-5968.
[8] YANG Z D, CHEN H, LI Y C.A new glycoside and a novel-type diterpene from Hemerocallis fulva (L.)[J].Helvetica Chimica Acta, 2003, 86(10):3305-3309.
[9] SZEWCZYK K, KALEMBA D, MIAZGA-KARSKA M, et al.The essential oil composition of selected Hemerocallis cultivars and their biological activity[J].Open Chemistry, 2019, 17(1):1412-1422.
[10] 陈秀萍, 苏文炳, 蒋际谋, 等.基于UPLC-MS/MS的枇杷不同组织萜类代谢物鉴定[J].果树学报, 2022, 39(11):2099-2112.
CHEN X P, SU W B, JIANG J M, et al.UPLC-MS/MS identification of terpenoid metabolites in different organs of Eriobotrya japonica[J].Journal of Fruit Science, 2022, 39(11):2099-2112.
[11] 丁亚丽. 基于非靶代谢组学多刺绿绒蒿不同器官代谢物差异分析[J].生物资源, 2022, 44(5):476-483.
DING Y L.Analysis of metabolites in different organs of Meconopsis horridula based on untargeted metabolomics[J].Biotic Resources, 2022, 44(5):476-483.
[12] 陈卓, 胡芯, 唐洪玉.黑藻(Hydrilla verticillat)在铅、锌胁迫下的代谢组学研究[J].生态毒理学报, 2022, 17(4):405-416.
CHEN Z, HU X, TANG H Y.Metabolomics study of Hydrilla verticillata under heavy metal stress of lead and zinc[J].Asian Journal of Ecotoxicology, 2022, 17(4):405-416.
[13] SEGLA KOFFI DOSSOU S, XU F T, YOU J, et al.Widely targeted metabolome profiling of different colored sesame (Sesamum indicum L.) seeds provides new insight into their antioxidant activities[J].Food Research International, 2022, 151:110850.
[14] WANG L, ZHANG T, SHEN T, et al.Serum metabolomics for early diagnosis of esophageal squamous cell carcinoma by UHPLC-QTOF/MS[J].Metabolomics, 2016, 12(7):116.
[15] THÉVENOT E A, ROUX A, XU Y, et al.Analysis of the human adult urinary metabolome variations with age, body mass index, and gender by implementing a comprehensive workflow for univariate and OPLS statistical analyses[J].Journal of Proteome Research, 2015, 14(8):3322-3335.
[16] 武珍珍, 洪沙沙, 吕虹瑞, 等.黄花菜保鲜贮藏及后处理加工技术研究进展[J].食品与发酵工业, 2022, 49(22):334-340.
WU Z Z, HONG S S, LYU H R, et al.Research progress in fresh-keeping, storage and post-processing technology of daylily[J].Food and Fermentation Industries, 2023, 49(22):334-340.
[17] SINGH B, SHARMA R A.Plant terpenes:Defense responses, phylogenetic analysis, regulation and clinical applications[J].3 Biotech, 2015, 5(2):129-151.
[18] RADHAKRISHNA S, KUMARI P S.GCMS analysis of total terpenoids from Baliospermum montanum and its antimicrobial activity[J].Iaetsd Journal for Advanced Research in Applied Sciences, 2021, 5(3):94-101.
[19] 吴德虎, 唐慧莉, 陈慧.松香酸通过上调miR-30a-3p表达增强缺氧诱导的HUVECs血管生成[J].浙江中西医结合杂志, 2022, 32(8):710-715.
WU D H, TANG H L, CHEN H.Abietic acid enhances hypoxia-induced angiogenesis in human umbilical vein endothelial cells (HUVECs) by upregulating miR-30a-3p expression[J].Zhejiang Journal of Integrated Traditional Chinese and Western Medicine, 2022, 32(8):710-715.
[20] 刘勇, 闫小宁.基于网络药理学的松香酸治疗银屑病的作用机制研究[J].世界临床药物, 2022, 43(1):19-25.
LIU Y, YAN X N.Mechanism of anti-psoriasis of abietic acid based on network pharmacology[J].World Clinical Drugs, 2022, 43(1):19-25.
[21] TAKAHASHI N, KAWADA T, GOTO T, et al. Abietic acid activates peroxisome proliferator-activated receptor-γ (PPARγ) in RAW264.7 macrophages and 3T3-L1 adipocytes to regulate gene expression involved in inflammation and lipid metabolism. FEBS Letters, 2003, 550(1-3):190-194.
[22] 程立方, 崔秀君.抗痨胶囊中异海松酸的含量测定[J].中国医院药学杂志, 2007, 27(5):702-703.
CHENG L F, CUI X J.Determination of isopimaric acid in antituberculosis capsules[J].Chinese Journal of Hospital Pharmacy, 2007, 27(5):702-703.
[23] SALARI S, SILVERÅ EJNEBY M, BRASK J, et al.Isopimaric acid-a multi-targeting ion channel modulator reducing excitability and arrhythmicity in a spontaneously beating mouse atrial cell line[J].Acta Physiologica, 2018, 222(1):10.1111/apha.
[24] 魏希颖, 张延妮, 白玲玲, 等.泡桐花油的GC-MS分析及抑菌作用研究[J].天然产物研究与开发, 2008, 20(1):87-90.
WEI X Y, ZHANG Y N, BAI L L, et al.Analysis of oil in the Flos paulowniae by GC-MS and study on antibacterial function[J].Natural Product Research and Development, 2008, 20(1):87-90.
[25] 范铮, 宋庆宝, 强根荣, 等.荞麦籽粒石油醚萃取物化学成分的研究[J].林产化工通讯, 2003, 37(5):17-20.
FAN Z, SONG Q B, QIANG G R, et al.Study on chemical constituents of petroleum ether extract from the seed of Fagopyrum esculentum[J].Journal of Chemical Industry of Forest Products (Bimonthly), 2003, 37(5):17-20.
[26] 张倩, 唐娜娜, 于海林, 等.广玉兰果实脂肪酸成分的GC-MS分析[J].河南大学学报(医学版), 2009, 28(2):101-103.
ZHANG Q, TANG N N, YU H L, et al.Analysis of fatty acids from fruit of Magnolia grandifore by GC-MS[J].Journal of Henan University (Medical Science), 2009, 28(2):101-103.
[27] KIM J S, JUN D Y, WOO M H, et al.Chemical composition and antitumor apoptogenic activity of methylene chloride extracts from the leaves of Zanthoxylum schinifolium[J].Journal of Life Science, 2006, 16(3):546-554.
[28] HASAN A E Z, ARTIKA I M, KUSWANDI, et al.Analysis of active components of Trigona spp propolis from pandeglang indonesia[J].Global Journal of Biology, Agriculture & Health Sciences, 2014, 3(1):215-219.
[29] ONO M, YAMASAKI T, KONOSHITA M, et al.Five new diterpenoids, Viteagnusins A:E, from the fruit of Vitex agnus-castus[J].Chemical and Pharmaceutical Bulletin, 2008, 56(11):1621-1624.
[30] ONO M, YAMAMOTO M, YANAKA T, et al.Ten new labdane-type diterpenes from the fruit of Vitex rotundifolia[J].Chemical and Pharmaceutical Bulletin, 2001, 49(1):82-86.
[31] 闫利华, 张启伟, 王智民, 等.三叶蔓荆化学成分研究(Ⅱ)[J].中草药, 2010, 41(10):1622-1624.
YAN L H, ZHANG Q W, WANG Z M, et al. Studies on chemical constituents of Vitex trifoliata (Ⅱ). Chinese Traditional and Herbal Drugs, 2010, 41(10):1622-1624.
[32] IBRAHIM N A, SHALABY A S, FARAG R S, et al.Phytochemical investigation and hormonal activity of Vitex agnus-castus L.fruits growing in Egypt[J].Jasmr, 2008, 1(1):63-74.
[33] DENIZ G Y, LALOGLU E, ALTUN S, et al.Antioxidant and anti-apoptotic effects of vitexilactone on cisplatin-induced nephrotoxicity in rats[J].Biotechnic & Histochemistry: Official Publication of the Biological Stain Commission, 2020, 95(5):381-388.
[34] HAJDÚ Z, HOHMANN J, FORGO P, et al.Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents[J].Phytotherapy Research:PTR, 2007, 21(4):391-394.
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