Abstract
Phytochemical investigation of 70% EtOH extract of the seeds of Capsella bursa-pastoris led to the isolation of a new cyclobutane organic acid (1), and fourteen known compounds, including two organosulfur compounds (2, 3), two quinonoids (4, 5), five flavonoids (6-10), three sterols (11-13) and two other types (14, 15). The structures of the compounds were elucidated by extensive spectroscopic analyses as well as comparison of their spectroscopic data with those reported in the literature. The antioxidant capacities of all compounds and extractive fractions were evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging test and ferric reducing antioxidant power (FRAP) assay. Then the antioxidative substances were evaluated for their neuroprotective effects against H2O2-induced HT22 cell injury. The results indicated the strong scavenging ability to free radical of the extractive fractions and compounds 1-3, 8-10 and 13, and the ferric reducing antioxidant power of the extractive fractions and compounds 1-3, 8 and 10, which were close to or higher than that of the positive control trolox. The EtOAc fraction, n-BuOH fraction, and compounds 1, 3 and 8 can protect HT-22 cells from oxidative damage.
Graphical abstract
Similar content being viewed by others
Data Availability
All relevant data are within the manuscript and its supplementary material, and are also available from the corresponding author on reasonable request.
References
Rong S, Xu R, Li W (2016) Phytosterols and dementia. Plant Foods Hum Nutr 71(4):347–354. https://doi.org/10.1007/s11130-016-0574-1
Weintraub D, Aarsland D, Chaudhuri KR, Dobkin RD, Leentjens AF, Rodriguez-Violante M, Schrag A (2022) The neuropsychiatry of Parkinson's disease: advances and challenges. Lancet Neurol 21(1):89–102. https://doi.org/10.1016/S1474-4422(21)00330-6
Maldonado J, Huang JH, Childs EW, Tharakan B (2023) Racial/ethnic differences in traumatic brain injury: pathophysiology, outcomes, and future directions. J Neurotrauma 40(5-6):502–513. https://doi.org/10.1089/neu.2021.0455
Levite M (2023) Neuro faces of beneficial T cells: essential in brain, impaired in aging and neurological diseases, and activated functionally by neurotransmitters and neuropeptides. Neural Regen Res 18(6):1165–1178. https://doi.org/10.4103/1673-5374.357903
Ren L, Fang XP, Sun CC, Chen KR, Liu F, Li M, Xu L (2014) First report of Clubroot on Capsella bursa-pastoris caused by Plasmodiophora brassicae in Sichuan Province of China. Plant Dis 98(5):687. https://doi.org/10.1094/PDIS-04-13-0395-PDN
Matthaus B, Özcan MM, Al Juhaimi F (2016) Some rape/canola seed oils: fatty acid composition and tocopherols. Z Naturforsch C J Biosci 71(3-4):73–77. https://doi.org/10.1515/znc-2016-0003
Schepici G, Bramanti P, Mazzon E (2020) Efficacy of sulforaphane in neurodegenerative diseases. Int J Mol Sci 21(22):8637. https://doi.org/10.3390/ijms21228637
Feng WS, Li CG, Zheng XK, Li LL, Chen WJ, Zhang YL, Cao YG, Gong JH, Kuang HX (2016) Three new sulphur glycosides from the seeds of Descurainia sophia. Nat Prod Res 30(15):1675–1681. https://doi.org/10.1080/14786419.2015.1135141
Zhang GJ, Li B, Cui HM, Chen L, Tian Y, Liu SJ, Li BW, Li M, Xia ZM, Chen XX, Hou Y, Dong JX (2018) Orychophragines A-C, three biologically active alkaloids from Orychophragmus violaceus. Org Lett 20(3):656–659. https://doi.org/10.1021/acs.orglett.7b03801
Choi WJ, Kim SK, Park HK, Sohn UD, Kim W (2014) Anti-inflammatory and anti-superbacterial properties of Ssulforaphane from Shepherd's purse. Korean J Physiol Pharmacol 18(1):33–39. https://doi.org/10.4196/kjpp.2014.18.1.33
Park CJ, Park CB, Hong SS, Lee HS, Lee SY, Kim SC (2000) Characterization and cDNA cloning of two glycine- and histidine-rich antimicrobial peptides from the roots of shepherd's purse, Capsella bursa-pastoris. Plant Mol Biol 44(2):187–197. https://doi.org/10.1023/a:1006431320677
Cha JM, Suh WS, Lee TH, Subedi L, Kim SY, Lee KR (2017) Phenolic glycosides from Capsella bursa-pastoris (L.) Medik and their anti-inflammatory activity. Molecules 22(6):1023. https://doi.org/10.3390/molecules22061023
Contestabile A (2001) Oxidative stress in neurodegeneration: mechanisms and therapeutic perspectives. Curr Top Med Chem 1(6):553–568. https://doi.org/10.2174/1568026013394723
Azam F, Prasad MV, Thangavel N (2012) Targeting oxidative stress component in the therapeutics of epilepsy. Curr Top Med Chem 12(9):994–1007. https://doi.org/10.2174/156802612800229224
Nolasco Lugo LM, Nunes NMF, do Nascimento Silva J, da Silva Araûjo L, de Macêdo Gonçalves Frota K (2018) Cruciferous vegetables as antioxidative, chemopreventive and antineoplasic functional foods: preclinical and clinical evidences of sulforaphane against prostate cancers. Curr Pharm Des 24(40):4779–4793. https://doi.org/10.2174/1381612825666190116124233
Wei ZZ, Zhou TQ, Xia ZM, Liu SF, Li M, Zhang GJ, Tian Y, Li B, Wang L (2022) Four organosulfur compounds from the seeds of Capsella bursa-pastoris and their anti-inflammatory activities. Nat Prod Res 6:1–9. https://doi.org/10.1080/14786419.2022.2130307
Harkat H, Haba H, Marcourt L, Long M (2007) An unusual lignan sulfate and aromatic compounds from Frankenia thymifolia Desf. Biochem Syst Ecol 35:176–179
Sun K, Li X, Liu JM, Wang JH, Li W, Sha Y (2005) A novel sulphur glycoside from the seeds of Descurainia sophia (L.). J Asian Nat Prod Res 7(6):853–856. https://doi.org/10.1080/1028602042000204072
Hong YL, Ma L, Wang YF, Sun JF, Hou GG, Zhao F, Han JT, Wang CH (2014) Anthraquinones and triterpenoids from roots of Knoxia roxburghii. Zhongguo Zhong Yao Za Zhi 39(21):4230–4233
Hu J, Zhang WD, Liu RH, Zhang C, Shen YH, Xu XK, Liang MJ, Li HL (2006) Chemical constituents in root of Zanthoxylum nitidum. Zhongguo Zhong Yao Za Zhi 31(20):1689–1691
Zaragozá C, Monserrat J, Mantecón C, Villaescusa L, Álvarez-Mon MÁ, Aragozá F, Álvarez-Mon M (2021) Binding and antiplatelet activity of quercetin, rutin, diosmetin, and diosmin flavonoids. Biomed Pharmacother 141:111867. https://doi.org/10.1016/j.biopha.2021.111867
Wang AQ, Wang XK, Li JL, Cui XY (2004) Isolation and structure identification of chemical constituents from the seeds of Descurainia sophia (L.) Webb ex Prantl. Yao Xue Xue Bao 39(1):46–51
Barreca D, Bellocco E, D'Onofrio G, Nabavi SF, Daglia M, Rastrelli L, Nabavi SM (2016) Neuroprotective effects of quercetin: from chemistry to medicine. CNS Neurol Disord Drug Targets 15(8):964–975. https://doi.org/10.2174/1871527315666160813175406
Shi Q, Chen K, Li L, Chang JJ, Autry C, Kozuka M, Konoshima T, Estes JR, Lin CM, Hamel E (1995) Antitumor agents, 154. Cytotoxic and antimitotic flavonols from Polanisia dodecandra. J Nat Prod 58(4):475–482. https://doi.org/10.1021/np50118a001
Kim BG, Lee Y, Hur HG, Lim Y, Ahn JH (2006) Flavonoid 3'-O-methyltransferase from rice: cDNA cloning, characterization and functional expression. Phytochemistry 67(4):387–394. https://doi.org/10.1016/j.phytochem.2005.11.022
Umlauf D, Zapp J, Becker H, Adam KP (2004) Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). Phytochemistry 65(17):2463–2470. https://doi.org/10.1016/j.phytochem.2004.08.019
Bao Y, Yanase E, Nakatsuka S (2013) Isolation of campesteryl ferulate and epi-campesteryl ferulate, two components of γ-oryzanol from rice bran. Biosci Biotechnol Biochem 77(4):877–879. https://doi.org/10.1271/bbb.120938
Chen L, Liu YJ, Huang FF, Huang SY, Lan MS (2018) Chemical constituents from ethyl acetate extracts of domestic Pfaffia glomerata. Chin Tradit Herb Drugs 49(06):1255–1260. https://doi.org/10.7501/j.issn.0253-2670.2018.06.004
Kobayashi S, Waki T, Nakanishi I, Matsumoto K, Anzai K (2010) Potent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity of novel antioxidants, double-stranded tyrosine residues conjugating pyrocatechol. Chem Pharm Bull (Tokyo) 58(11):1442–1446. https://doi.org/10.1248/cpb.58.1442
Guo J, Zhang Y, Zhang C, Yao C, Zhang J, Jiang X, Zhong Z, Ge J, Zhou T, Bai R (2021) N-propargylamine-hydroxypyridinone hybrids as multitarget agents for the treatment of Alzheimer’s disease. Bioorg Chem 113:105013. https://doi.org/10.1080/14756366.2022.2134358
Lin F, Huang X, Xing F, Xu L, Zhang W, Chen Z, Ke X, Song Y, Zeng Z (2020) Semen Brassicae reduces thoracic aortic remodeling, inflammation, and oxidative amage in spontaneously hypertensive rats. Biomed Pharmacother 129:110400. https://doi.org/10.1016/j.biopha.2020.110400
Author information
Authors and Affiliations
Contributions
Ti-Qiang Zhou and Zhen-Zhen Wei wrote the main manuscript text and prepared Figs. 1, 2, 3, 4 and 5; Jin-Rui Zhang, Jia-Hui Dong, Chun-Ying Liu and Cong-Zhi Jiang taken the formal analysis of the manuscript; Zi-Ming Xia, Si-Fan Liu, Min Li and Guang-jie Zhang curated the related data; and Li Chen, Ying Tian, Bin Li, and Shu-Chen Liu reviewed and edited the manuscript. All authors reviewed the manuscript.
Corresponding authors
Ethics declarations
Ethical Approval and Consent to Participate
Not applicable.
Consent for Publication
Written informed consent for publication was obtained from all authors.
Conflict of Interest
No potential conflict of interest was reported by the authors.
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
ESM 1
(DOCX 4051 kb)
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Zhou, TQ., Wei, ZZ., Zhang, JR. et al. Phytochemical Constituents from the Seeds of Capsella bursa-pastoris and Their Antioxidant Activities. Plant Foods Hum Nutr 78, 776–782 (2023). https://doi.org/10.1007/s11130-023-01097-z
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11130-023-01097-z