Abstract
Pristimerin is a naturally occurring triterpenoid originally isolated from plant members of the genus Pristimera Miers, Celastraceae, and can be also isolated from the species of the Hippocrateaceae. The experimental outcomes in its phytochemical and pharmacological aspects are abundant, but an insight overview is not sufficient. The goal of the present review is to deeply describe natural sources, structural analysis, biosynthesis, pharmacology, and pharmacokinetics for this bioactive triterpenoid. Pristimerin showed various in vitro and in vivo pharmacological properties, such as a cytotoxic, antitumor, anti-inflammation, antibacterial, or antiviral agent. Its underlying mechanisms in anticancer include apoptosis, autophagy, anti-inflammatory cytokine inhibition, migration and invasion, vasculogenesis, and inhibition of drug resistance. Pristimerin is much better than the standard compound ampicillin against methicillin-resistant strains Staphylococcus aureus. Studies on the synthesis, structure–activity relationships, toxicology, and clinical application are needed. Solutions to improve the low bioavailability are expected.
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The data presented in this study are available in article and Supplementary Material.
References
Al-Tamimi M, Khan AQ, Anver R (2022) Pristimerin mediated anticancer effects and sensitization of human skin cancer cells through modulation of MAPK signaling pathways. Biomed Pharmacother 156:113950. https://doi.org/10.1016/j.biopha.2022.113950
Ankli A, Heilmann J, Heinrich M, Sticher O (2000) Cytotoxic cardenolides and antibacterial terpenoids from Crossopetalum gaumeri. Phytochemistry 54:531–537. https://doi.org/10.1016/S0031-9422(00)00144-8
Araujo-Leon JA, Cantillo-Ciau Z, Ruiz-Ciau DV, Coral-Martinez TI (2019) HPLC profile and simultaneous quantitative analysis of tingenone and pristimerin in four Celastraceae species using HPLC-DAD-MS. Rev Bras Farmacogn 29:171–176. https://doi.org/10.1016/j.bjp.2018.12.009
Avilla J, Teixido A, Velazquez C, Alvarenga N, Ferro E, Canela R (2000) Insecticidal activity of maytenus species (Celastraceae) nortriterpene quinone methides against codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae). J Agric Food Chem 48:88–92. https://doi.org/10.1021/jf990008w
Bai S, Gao W, Deng Q, Lin X, Zheng J, Chen Y, Tong L (2020) Pristimerin inhibits adjuvant arthritis fibroblast like synoviocytes cell proliferation through cell cycle arrest and induction of apoptosis. Indian J Pharm Sci 82:809–817
Bi J, Areecheewakul S, Li Y, Yang S, Zhang Y, Ebeid K, Li L, Thiel KW, Zhang J, Dai D, Salem AK, Leslie KK, Meng X (2019) MTDH/AEG-1 downregulation using pristimerin-loaded nanoparticles inhibits Fanconi anemia proteins and increases sensitivity to platinum-based chemotherapy. Gynecol Oncol 155:349–358. https://doi.org/10.1016/j.ygyno.2019.08.014
Bicalho KU, Santoni MM, Arendt P, Zanelli CF, Furlan M, Goossens A, Pollier J (2019) CYP712K4 catalyzes the c-29 oxidation of friedelin in the Maytenus ilicifolia quinone methide triterpenoid biosynthesis pathway. Plant Cell Physiol 60:2510–2522. https://doi.org/10.1093/pcp/pcz144
Carvalho PRF, Silva DHS, Bolzani VS, Furlan M (2005) Antioxidant quinonemethide triterpenes from Salacia campestris. Chem Biodiver 2:367–372. https://doi.org/10.1002/cbdv.200590016
Cevatemre B, Erkisa M, Aztopal N, Karakas D, Alper P, Tsimplouli C, Sereti E, Dimas K, Armutak EII, Gurevin EG, Uvez A, Mori M, Berardozzi S, Ingallina C, D’Acquarica I, Botta B, Ozpolat B, Ulukaya E (2018) A promising natural product, pristimerin, results in cytotoxicity against breast cancer stem cells in vitro and xenografts in vivo through apoptosis and an incomplete autopaghy in breast cancer. Pharmacol Res 129:500–514. https://doi.org/10.1016/j.phrs.2017.11.027
Chang FR, Hayashi KI, Chen IH (2003) Antitumor agents. 228. Five new agarofurans, reissantins A-E, and cytotoxic principles from Reissantia buchananii. J Nat Prod 66:1416–1420. https://doi.org/10.1021/np030241
Chauhan K, Tripathi YC, Varshney VK (2023) Prinsepia utilis Royle: a review on its traditional uses, phytochemistry, and biological activities. Phytochem Lett 55:44–55. https://doi.org/10.1016/j.phytol.2023.03.009
Cheng S, Zhang Z, Xing N, Xia Y, Pang B (2020) Pristimerin suppressed breast cancer progression via miR-542-5p/DUB3 axis. Oncotargets Ther 13:6651–6660. https://doi.org/10.2147/OTT.S257329
Costa PMD, Ferreira PMP, Bolzani VDS (2008) Antiproliferative activity of pristimerin isolated from Maytenus ilicifolia (Celastraceae) in human HL-60 cells. Toxicol in Vitro 22:854–863. https://doi.org/10.1016/j.tiv.2008.01.003
Deeb D, Gao X, Liu YB, Pindolia K, Gautam SC (2014) Pristimerin, a quinonemethide triterpenoid, induces apoptosis in pancreatic cancer cells through the inhibition of pro-survival Akt/NF-κB/mTOR signaling proteins and anti-apoptotic Bcl-2. Int J Oncol 44:1707–1715. https://doi.org/10.3892/ijo.2014.2325
Deng Q, Bai S, Gao W, Tong L (2015) Pristimerin inhibits angiogenesis in adjuvant-induced arthritic rats by suppressing VEGFR2 signaling pathways. Int Immunopharmacol 29:302–313. https://doi.org/10.1016/j.intimp.2015.11.001
Dong C, Xu C, Liu H, Xu S, Gao Y, Peng J (2015) Absorption and metabolism characterisitics of pristimerin as determined by a sensitive and reliable LC-MS/MS method. Fitoterpia 106:62–67. https://doi.org/10.1016/j.fitote.2015.08.006
Edwards JM, Schwarting AE (1973) Isolation of pristimerin from Pachystima canbyi. Phytochemistry 12:945. https://doi.org/10.1016/0031-9422(73)80712-5
El-Agamy DS, Shaaban MA, Almaramhy HH, Elkablawy S, Elkablawy MA (2018) Pristimerin as a novel hepatoprotective agent against experimental autoimmune hepatitis. Front Pharmacol 9:292. https://doi.org/10.3389/fphar.2018.00292
El-Agamy DS, El-Harbi KM, Khoshhal S, Ahmed N, Elkablawy MA, Shaaban AA, Abo-Haded HM (2019) Pristimerin protects against doxorubicin-induced cardiotoxicity and fibrosis through modulation of Nrf2 and MAPK/NF-κB signaling pathways. Cancer Manag Res 11:47–61. https://doi.org/10.2147/CMAR.S186696
Gamlath CB, Leslie Gunatilaka AA, Tezuka Y, Kikuchi T, Balasubramaniam S (1990) Quinone-methide, phenolic and related triterpenoids of plants of Celastraceae: further evidence for the structure of celastranhydride. Phytochemistry 29:3189–3192. https://doi.org/10.1016/0031-9422(90)80182-G
Gao X, Liu Y, Deeb D, Arbab AS, Gautam SC (2014) Anticancer activity of pristimerin in ovarian carcinoma cells is mediated through the inhibition of prosurvival Akt/NF-κB/mTOR signaling. J Exp Ther Oncol 10:275–283
Gao X, Zhang Y, Wang Y, Zhang Y, Wang Y, Liu S, Gao X (2016) Influence of verapamil on pharmacokinetics of pristimerin in rats. Biomed Chromatograph 30:802–809. https://doi.org/10.1002/bmc.3611
Gomes JPM, Cardoso CRP, Varanda EA, Molina JM, Fernandez MF, Olea N, Carlos IZ, Vilegas W (2011) Antitumoral, mutagenic and (anti)estrogenic activities of tingenone and pristimerin. Rev Bras Farmacogn 21:963–971. https://doi.org/10.1590/S0102-695X2011005000153
Gonzalez AG, Alvarenga NL, Rodriguez F, Ravelo AG, Jimenez IA, Bazzochi IL, Gupta MP (1995) New phenolic and quinone-methide triterpenes from Maytenus species (Celastraceae). Nat Prod Lett 7:209–218. https://doi.org/10.1080/10575639508043213
González-Félix MA, Mejía-Manzano LA, Barba-Dávila BA, Serna-Saldívar SO, González-Valdez J (2021) Optimized and scalable green extraction of pristimerin, an anticancerigen from Mortonia greggii, by ethanol-phosphate aqueous two-phase systems. Ind Eng Chem Res 60:5403–5410. https://doi.org/10.1021/acs.iecr.1c00473
Gullo FP, Sardi JCO, Santos VAFFM, Leite FS, Pitangui NS, Rossi SA, Paula Silva ACA, Soares LA, Silva JF, Oliveira HC, Furlan M, Silva DHS, Bolzani VS, Mendes-Giannini MJS, Fusco-Almeida A (2012) Antifungal activity of maytenin and pristimerin. Evid-Based Compl Alt Med 2012:340787. https://doi.org/10.1155/2012/340787
Gunatilaka AAL (1996) Triterpenoid quinonemethides and related compounds (celastroloids). Prog Chem Org Nat Prod vol 67. Springer, Vienna. https://doi.org/10.1007/978-3-7091-9406-5_1
Hao X, Yuan J, Xu Y, Wang Z, Hou J, Hu T (2018) In vitro inhibitory effects of pristimerin on human liver cytochrome P450 enzymes. Xenobiotica 48:1185–1191. https://doi.org/10.1080/00498254.2017.1316886
Happi GM, Ntabo VK, Tcho AT, Wansi JD (2022) Naturally occurring dimeric triterpenoids: occurrence, chemistry and bioactivities. Phytochemistry 200:113242. https://doi.org/10.1016/j.phytochem.2022.113242
Harada R, Kakisawa H, Kobayashi S, Musya M, Nakanishi K, Takahashi Y (1962) Structure of pristimerin, a quinonoid triterpene. Tetrahedron Lett 14:603–607. https://doi.org/10.1016/S0040-4039(00)70915-4
Hayashi D, Shirai T, Terauchi R, Tsuchida S, Mizoshiri N, Mori Y, Mazda O, Kubo T (2020) Pristimerin inhibits the proliferation of HT1080 fibrosarcoma cells by inducing apoptosis. Oncol Lett 19:2963–2970. https://doi.org/10.3892/ol.2020.11405
Hop NQ, Son NT (2022) Botanical description, traditional uses, phytochemistry, and pharmacology of the genus Artabotrys: a review. Chem Biodiver 19:e202200725. https://doi.org/10.1002/cbdv.202200725
Huan DQ, Hop NQ, Son NT (2023) Oxymatrine: a current overview of its health benefits. Fitoterapia 168:105565. https://doi.org/10.1016/j.fitote.2023.105565
Huang S, He P, Peng X, Li J, Xu D, Tang Y (2015) Pristimerin inhibits prostate cancer bone metastasis by targeting PC-3 stem cell characteristics and VEGF-induced vasculogenesis of BM-EPCs. Cell Physiol Biochem 37:253–268. https://doi.org/10.1159/000430350
Huang D, Su L, He C, Chen L, Huang D, Peng J, Yang F, Cao Y, Luo X (2022) Pristimerin alleviates cigarette smoke-induced inflammation in chronic obstructive pulmonary disease via inhibiting NF-κB pathway. Biochem Cell Biol 100:223–235. https://doi.org/10.1139/bcb-2021-0251
Hui B, Zhang L, Zhou Q, Hui L (2018) Pristimerin inhibits lps-triggered neurotoxicity in bv-2 microglia cells through modulating IRAK1/TRAF6/TAK1-Mediated NF-κB and AP-1 signaling pathways in vitro. Neurotox Res 33:268–283. https://doi.org/10.1007/s12640-017-9837-3
Huong NT, Son NT (2023) Icaritin: a phytomolecule with enormous pharmacological values. Phytochemistry 213:113772. https://doi.org/10.1016/j.phytochem.2023.113772
Itokawa H, Shirota O, Ikuta H, Morita H, Takeya K, Itaka Y (1991) Triterpenes from Maytenus ilicifolia. Phytochemistry 30:3713–3716. https://doi.org/10.1016/0031-9422(91)80096-J
Jiang Z, Zhao Y, Zhao Y, Liu Y, Tao L (2021) Pristimerin synergizes with gemcitabine through abrogating Chk1/53BP1-mediated DNA repair in pancreatic cancer cells. Food Chem Toxicol 147:111919. https://doi.org/10.1016/j.fct.2020.111919
Kamal GM, Gunaherath B, Leslie Gunatilaka AA (1983) Studies on terpenoids and steroids. Part 3. ’ structure and synthesis of a new phenolic D:A-friedo-24-noroieanane triterpenoid, zeyiasterone, from Kokoona zeylanica. J Chem Soc Perkin Trans I 1:2845–2850. https://doi.org/10.1039/P19830002845
Kennedy ML, Lianos GG, Castanys S, Gamarro F, Bazzocchi IL, Jimenez IA (2011) Terpenoids from Maytenus species and assessment of their reversal activity against a multidrug-resistant Leishmania tropica Line. Chem Biodiver 8:2291–2298. https://doi.org/10.1002/cbdv.201000356
Khalid SA, Fridrichsen GM, Christensen SB, Tahir AE, Satti GM (2007) Isolation and characterization of pristimerin as the antiplasmodial and antileishmanial agent of Maytenus senegalensis (Lam.) Exell. ARKIVOC 9:129–134
Kim HJ, Park GM, Kim JK (2013) Anti-inflammatory effect of pristimerin on lipopolysaccharide induced inflammatory responses in murine macrophages. Arch Pharm Res 36:495–500. https://doi.org/10.1007/s12272-013-0054-1
Kulkarni AB, Shah RC (1954) Structure of pristimerin. Nature 173:1237–1238. https://doi.org/10.1038/1731237b
Lee JS, Yoon IS, Lee MS, Cha EY, Thuong PT, Diep TT, Kim JR (2013) Anticancer activity of pristimerin in epidermal growth factor receptor 2-positive skbr3 human breast cancer cells. Biol Pharm Bul 36:316–325. https://doi.org/10.1248/bpb.b12-00685
Lee SO, Kim JS, Lee MS, Lee HJ (2016) Anti-cancer effect of pristimerin by inhibition of HIF-1α involves the SPHK-1 pathway in hypoxic prostate cancer cells. BMC Cancer 16:701. https://doi.org/10.1186/s12885-016-2730-2
Lee Y, Na J, Lee MS (2018) Combination of pristimerin and paclitaxel additively induces autophagy in human breast cancer cells via ERK1/2 regulation. Mol Med Rep 18:4281–4288. https://doi.org/10.3892/mmr.2018.9488
Li Z, Hu C, Zhen Y, Pang B, Yi H, Chen X (2019) Pristimerin inhibits glioma progression by targeting AGO2 and PTPN1 expression via miR-542-5p. Bio Rep 39:BSR182389. https://doi.org/10.1042/BSR20182389
Li J, Guo Q, Lei X, Zhang L, Su C, Liu Y, Zhou W, Chen H, Wang H, Wang F, Yan Y, Zhang J (2020) Pristimerin induces apoptosis and inhibits proliferation, migration in H1299 lung cancer cells. J Cancer 11:6348–6355. https://doi.org/10.7150/jca.44431
Liang J, Yuan S, Wang X, Lei Y, Zhang X, Huang M, Ouyang H (2020) Attenuation of pristimerin on TNF-α-induced endothelial inflammation. Int Immunopharmacol 82:106326. https://doi.org/10.1016/j.intimp.2020.106326
Liu YB, Gao X, Deeb D, Arbab AS, Gau SC (2013) Pristimerin induces apoptosis in prostate cancer cells by downregulating Bcl-2 through ROS-dependent ubiquitin-proteasomal degradation pathway. J Carcinogene Mutagene S 6:005. https://doi.org/10.4172/2157-2518.S6-005
Liu Y, Ren Z, Li X (2019) Pristimerin induces autophagy-mediated cell death in K562 cells through the ROS/JNK signaling pathway. Chem Biodiver 16:e1900325. https://doi.org/10.1002/cbdv.201900325
Liu S, Dong Y, Wang Y, Hu P, Wang J, Wang RYL (2021) Pristimerin exerts antitumor activity against MDA-MB-231 triple-negative breast cancer cells by reversing of epithelial-mesenchymal transition via downregulation of integrin β3. Biomed J 44:S84–S92. https://doi.org/10.1016/j.bj.2020.07.004
Lu Z, Jin Y, Chen C, Li J, Cao Q, Pan J (2010) Pristimerin induces apoptosis in imatinib-resistant chronic myelogenous leukemia cells harboring T315I mutation by blocking NF-κB signaling and depleting Bcr-Abl. Mol Cancer 9:112. https://doi.org/10.1186/1476-4598-9-112
Lu Y, Zeng Z, Bao X, Wu M, Jing Z, Feng J (2023) Pristimerin protects against pathological cardiac hypertrophy through improvement of PPARα pathway. Toxicol Appl Pharmacol 473:116572. https://doi.org/10.1016/j.taap.2023.116572
Luan X, Guan YY, Liu YR, Wang C, Zhao M, Lu Q, Tang YB, Wang XL, Fang C, Chen HZ (2013) Development and validation of a quantitative liquid chromatography tandem mass spectrometry assay for pristimerin in rat plasma. J Chromatograph B 941:25–30. https://doi.org/10.1016/j.jchromb.2013.09.038
Luo DQ, Wang H, Tian X, Shao HJ, Liu JK (2005) Antifungal properties of pristimerin and celastrol isolated from Celastrus hypoleucus. Pest Manag Sci 61:85–90. https://doi.org/10.1002/ps.953
Mannowetz N, Mundt N, Lishko PV (2018) The plant triterpenoid pristimerin inhibits calcium influx into human spermatozoa via CatSper. Proc Natl Acad Sci 115:E347–E348. https://doi.org/10.1073/pnas.1719673115
Mejía-Manzano LA, Barba-Dávila BA, Gutierrez-Uribe JA, Escalante-Vázquez EJ, Serna-Saldívar SO (2015) Extraction and isolation of antineoplastic pristimerin from Mortonia greggii (Celastraceae). Nat Prod Commun 10:1923–1928. https://doi.org/10.1177/1934578X1501001130
Mejía-Manzano LA, Barba-Dávila VV, Saldívar SO, Gonzalez-Valdez J (2019) Improved extraction of the natural anticancerigen pristimerin from Mortonia greggii root bark using green solvents and aqueous two-phase systems. Sep Purif Technol 211:667–672. https://doi.org/10.1016/j.seppur.2018.08.056
Mengying L, Liang Q, Luo Z, Han B, Ni T, Wang Y, Tao L, Lyu W, Xiang J, Liu Y (2002) UPLC-LTQ-orbitrap-base cell metabolomics and network pharmacology analysis to reveal the potential antiarthritic effcts of pristimerin: in vitro, in silico and in vivo study. Metabolites 12:839. https://doi.org/10.3390/metabo12090839
Mori Y, Shirai T, Terauchi R, Tsuchida S, Mizoshiri N, Hayashi D, Arai Y, Kishida T, Mazda O, Kubo T (2017) Antitumor effects of pristimerin on human osteosarcoma cells in vitro and in vivo. Oncotargets Ther 10:5703–5710. https://doi.org/10.2147/OTT.S150071
Morita H, Hirasawa Y, Muto A, Yoshida T, Sekita S, Shirota O (2008) Antimitotic quinoid triterpenes from Maytenus chuchuhuasca. Bioorg Med Chem Lett 18:1050–1052. https://doi.org/10.1016/j.bmcl.2007.12.016
Mu X, Shi W, Sun L, Li H, Jiang Z, Zhang L (2012a) Pristimerin, a triterpenoid, inhibits tumor angiogenesis by targeting VEGFR2 activation. Molecules 17:6854–6868. https://doi.org/10.3390/molecules17066854
Mu XM, Shi W, Sun LX, Li H, Wang YR, Jiang ZZ, Zhang LY (2012b) Pristimerin inhibits breast cancer cell migration by upregulating regulator of g protein signaling 4 expression. Asian Pac J Cancer Prev 13:1097–1104. https://doi.org/10.7314/APJCP.2012.13.4.1097
Munoz O, Gonzalez A, Ravelo A, Estevez A (1999) Triterpenoid and phenolic compounds from two Chilean Celastraceae. Z Naturforsch C 54c:144–145. https://doi.org/10.1016/10.1515/znc-1999-1-223
Murayama T, Eizuru Y, Yamada R (2007) Anticytomegalovirus activity of pristimerin, a triterpenoid quinone methide isolated from Maytenus heterophylla (Eckl. & Zeyh.). Antivir Chem Chemother 18:133–139. https://doi.org/10.1177/095632020701800303
Ndako M, Jigam AA, Kabiru AY, Umar SI (2021) Polar extracts from Gymnosporia senegalensis (syn. Maytenus senegalensis) root bark, its effects on nociception, edema, and malarial infection. Phytomed Plus 1:100113. https://doi.org/10.1016/j.phyplu.2021.100113
Núñez MJ, Martínez ML, López-Arencibia A (2021) In vitro susceptibility of kinetoplastids to celastroloids from Maytenus chiapensis. Antimicrob Agents Chemother 65:e02236-e2320. https://doi.org/10.1128/aac.02236-20
Ochieng CO, Opiyo SA, Mureka EW, Ishola IO (2017) Cyclooxygenase inhibitory compounds from Gymnosporia heterophylla aerial parts. Fitoterapia 119:168–174. https://doi.org/10.1016/j.fitote.2017.04.015
Pal R, Kumar L, Anand S, Bharadvaja N (2023) Role of natural flavonoid products in managing osteoarthritis. Rev Bras Farmacogn 33:663–675. https://doi.org/10.1007/s43450-023-00387-6
Park JH, Kim JK (2018) Pristimerin, a naturally occurring triterpenoid, attenuates tumorigenesis in experimental colitis-associated colon cancer. Phytomedicine 42:164–171. https://doi.org/10.1016/j.phymed.2018.03.033
Qi D, Liu H, Sun X, Luo D, Zhu M, Tao T, Gao C, Zhou C, Zhou C, Zhou W, Xiao J (2021) Pristimerin suppresses RANKL-Induced osteoclastogenesis and ameliorates ovariectomy-induced bone loss. Front Pharmacol 11:621110. https://doi.org/10.3389/fphar.2020.621110
Rodrigues ACBDC, Oliveira FPD, Dias RB, Sales CB, Rocha CAG, Soares MBP, Costa EV, Silva FMAD, Rocha WC, Koolen HHF, Bezerra DP (2019) In vitro and in vivo anti-leukemia activity of the stem bark of Salacia impressifolia (Miers) A. C. Smith (Celastraceae). J Ethnopharmacol 231:516–524. https://doi.org/10.1016/j.jep.2018.11.008
Ryu YB, Park SJ, Kim YM, Lee JY, Seo WD, Chang JS, Park KH, Rho MC, Lee WS (2010) SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii. Bioorg Med Chem Lett 20:1873–1876. https://doi.org/10.1016/j.bmcl.2010.01.152
Santos VAFFMD, Leite KM, Siqueira MDC, Regasini LO, Martinez I, Nogueira CT, Galuppo MK, Stolf BS, Pereira AMS, Cicarelli RMB, Furlan M, Graminha MAS (2013) Antiprotozoal activity of quinonemethide triterpenes from Maytenus ilicifolia (Celastraceae). Molecules 18:1053–1062. https://doi.org/10.3390/molecules18011053
Seo HW, Park JH, Lee JY, Park HJ, Kim JK (2018) Pristimerin, a naturally occurring triterpenoid, exerts potent anticancer effect in colon cancer cells. Biomed Sci Lett 24:15–22. https://doi.org/10.15616/BSL.2018.24.1.15
Shaaban AA, El-Kashef DH, Hamed MF, El-Agamy DS (2018) Protective effect of pristimerin against LPS-induced acute lung injury in mice. Int Immunopharmacol 59:31–39. https://doi.org/10.1016/j.intimp.2018.03.033
Shu C, Yu X, Cheng S, Jing J, Hu C, Pang B (2020) Pristimerin suppresses trophoblast cell epithelial–mesenchymal transition via miR-542-5p/EGFR axis. Drug Des Devel Ther 14:4659–4670. https://doi.org/10.2147/DDDT.S274595
Silva FMAD, Paz WHP, Vasconcelos LSF, Silva ALBD, Silva-Filho FAD, Almeida RAD, Souza ADL, Pinheiro MLB, Koolen HHF (2016) Chemical constituents from Salacia impressifolia (Miers) A.C. Smith collected at the Amazon rainforest. Biochem System Ecol 68:77–80. https://doi.org/10.1016/j.bse.2016.07.004
Sun JM, Xu HT, Zhao L, Zhang YB, Kang PC, Song ZF, Liu HS, Cui YF (2018) Induction of cell-cycle arrest and apoptosis in human cholangiocarcinoma cells by pristimerin. J Cell Biochem 120:12002–12009. https://doi.org/10.1002/jcb.28485
Tang WH, Bai ST, Tong L, Duan WJ, Su JW, Chen JX, Xie Y (2014) Chemical constituents from Celastrus aculeatus Merr. Biochem System Ecol 54:78–82. https://doi.org/10.1016/j.bse.2014.01.001
Tang Y, Lei Y, Huang S, Li Z, Chen X, Luo H, Cheng C, Chen J, Zou X, Chen X (2020) Pristimerin exacerbates cellular injury in conditionally reprogrammed patient-derived lung adenocarcinoma cells by aggravating mitochondrial impairment and endoplasmic reticulum stress through EphB4/CDC42/N-WASP signaling. Oxid Med Cell Longev 2020:7409853. https://doi.org/10.1155/2020/7409853
Tang Y, Chen J, Li J, Zheng Y, Zhong Z, Huang S, Chen B, Peng B, Zou X, Chen X (2021) Pristimerin synergistically sensitizes conditionally reprogrammed patient derived-primary hepatocellular carcinoma cells to sorafenib through endoplasmic reticulum stress and ROS generation by modulating Akt/FoxO1/p27kip1 signaling pathway. Phytomedicine 85:153563. https://doi.org/10.1016/j.phymed.2021.153563
Tian M, Peng S, Wang S, Li X, Li L, Shen L (2021) Pristimerin reduces dextran sulfate sodium-induced colitis in mice by inhibiting microRNA-155. Int Immunopharmacol 94:107491. https://doi.org/10.1016/j.intimp.2021.107491
Tong L, Nanjundaiah SM, Venkatesha SH, Astry B, Yu H, Moudgil KD (2014) Pristimerin, a naturally occurring triterpenoid, protects against autoimmune arthritis by modulating the cellular and soluble immune mediators of inflammation and tissue damage. Clin Immunol 155:220–230. https://doi.org/10.1016/j.clim.2014.09.014
Tu Y, Tan F, Zhou J, Pan J (2018) Pristimerin targeting NF-kB pathway inhibits proliferation, migration, and invasion in esophageal squamous cell carcinoma cells. Cell Biochem Funct 36:228–240. https://doi.org/10.1002/cbf.3335
Wang Y, Zhou Y, Zhou H, Jia G, Liu J, Han B, Cheng Z, Jiang H, Pan S, Sun B (2012) Pristimerin causes G1 arrest, induces apoptosis, and enhances the chemosensitivity to gemcitabine in pancreatic cancer cells. PLoS ONE 7:e43826. https://doi.org/10.1371/journal.pone.0043826
Wang L, Wang Y, Lu Y, Yin ZF, Zhang YH, Aslanidi GV, Srivastava A, Ling CQ, Ling C (2014) Pristimerin enhances recombinant adeno-associated virus vector-mediated transgene expression in human cell line in vitro and murine hepatocytes in vivo. J Inter Med 12:20–34. https://doi.org/10.1016/S2095-4964(14)60003-0
Wang X, Huang L, Li P (2020) Pristimerin attenuates sepsis-induced lung injury by regulating nuclear factor kappaB/high-mobility group box 1 pathway. Trop J Pharm Res 19:1167–1171. https://doi.org/10.4314/tjpr.v19i6.7
Xiao-Mei C, Jin-Yu Z, Yang-Lang Y, Yu-Wei W, Yuan-Yuan Y, Hai-Hong X (2021) Pristimerin improve renal fibrosis by regulating miRNA-145-5p in vitro and in vivo study. Food Sci Technol 42:e79021. https://doi.org/10.1590/fst.79021
Xie Y, Ding Z, Duan W, Ye Q (2012) Isolation and purification of terpenoids from Celastrus aculeatus Merr. by high-speed counter-current chromatography. J Med Plants Res 6:2520–2525
Xu W, Zhu X, Chen C, Hu R, Li Y, Xu R, Li Z (2022) Beneficial effect of pristimerin against the development of osteoporosis in ovariectomy-induced osteoporosis rats by the RANKL/TRAF6/NF-κB pathway. Arch Med Sci 18:1650–1658. https://doi.org/10.5114/aoms.2019.86816
Xue W, Li Y, Zhang M (2021) Pristimerin inhibits neuronal inflammation and protects cognitive function in mice with sepsis-induced brain injuries by regulating PI3K/Akt signaling. Pharm Biol 59:1349–1356. https://doi.org/10.1080/13880209.2021.1981399
Yang H, Landis-Piwowar KR, Lu D, Yuan P, Li L, Prem-Veer Reddy G, Yuan X, Pind Dou Q (2008) Pristimerin induces apoptosis by targeting the proteasome in prostate cancer cells. J Cell Biochem 103:234–244. https://doi.org/10.1002/jcb.21399
Yang CC, Hsiao LD, Tseng HC, Kuo CM, Yang CM (2020) Pristimerin inhibits mmp-9 expression and cell migration through attenuating NOX/ROS-dependent NF-kB activation in rat brain astrocytes challenged with LPS. J Inflam Res 12:325–341. https://doi.org/10.2147/JIR.S252659
Yousef BA, Hassan HM, Guerram M, Hamdi AM, Wang B, Zhang LY, Jiang ZZ (2016) Pristimerin inhibits proliferatio, migration and invasion, and induces apoptosis in HCT-16 colorectal cancer cells. Biomed Pharmacol 79:112–119. https://doi.org/10.1016/j.biopha.2016.02.003
Yousef BA, Hassan HM, Zhang LY, Jiang ZZ (2018) Pristimerin exhibits in vitro and in vivo anticancer activities through inhibition of nuclear factor-кB signaling pathway in colorectal cancer cells. Phytomedicine 40:140–147. https://doi.org/10.1016/j.phymed.2018.01.008
Yousef BA, Hassan HM, Elhafiz M, Zhang L, Jiang Z (2020) Synergistic anti-cancer effect of pristimerin and docetaxel on human colorectal HCT-116 cells. Synergy 11:100068. https://doi.org/10.1016/j.synres.2020.100068
Yum S, Kwon JH, Lee KT, Park JT, Jeong HG (2022) Efficacy of pristimerin against Staphylococcus aureus planktonic cultures and biofilms. LWT 164:113627. https://doi.org/10.1016/j.lwt.2022.113627
Zhao H, Wang C, Lu B, Zhou Z, Jin Y, Wang Z, Zheng L, Liu K, Luo T, Zhu D, Chi G, Luo Y, Ge P (2016) Pristimerin triggers AIF-dependent programmed necrosis in glioma cells via activation of JNK. Cancer Lett 374:136–148. https://doi.org/10.1016/j.canlet.2016.01.055
Zhao X, Wu Y, Wang D (2018) Effects of glycyrrhizic acid on the pharmacokinetics of pristimerin in rats and its potential mechanism. Eur J Drug Met Ph 43:63–68. https://doi.org/10.1007/s13318-017-0423-0
Zhao Q, Liu Y, Zhong J, Bi Y, Liu Y, Ren Z, Li X, Jia J, Yu M, Yu X (2019) Pristimerin induces apoptosis and autophagy via activation of ROS/ASK1/JNK pathway in human breast cancer in vitro and in vivo. Cell Death Discov 5:125. https://doi.org/10.1038/s41420-019-0208-0
Zhao Q, Bi Y, Zhong J, Ren Z, Liu Y, Jia J, Yu M, Tan Y, Zhang Q, Yu X (2020) Pristimerin suppresses colorectal cancer through inhibiting inflammatory responses and Wnt/β-catenin signaling. Toxicol Appl Pharmacol 386:114813. https://doi.org/10.1016/j.taap.2019.114813
Zhao Q, Cheng X, Yu W, Bi Y, Guo J, Ma Q, Gong Y, He L, Yu X (2021a) Pristimerin induces apoptosis and tumor inhibition of oral squamous cell carcinoma through activating ROS-dependent ER stress/Noxa pathway. Phytomedicine 92:153723. https://doi.org/10.1016/j.phymed.2021.153723
Zhao Q, Bi Y, Guo J, Liu Y, Zhong J, Liu Y, Pan L, Guo Y, Tan Y, Yu X (2021b) Effect of pristimerin on apoptosis through activation of ROS/endoplasmic reticulum (ER) stress-mediated Noxa in colorectal cancer. Phytomedicine 80:153399. https://doi.org/10.1016/j.phymed.2020.153399
Zhao WB, Zhao ZM, Ma Y, Li AP, Zhang ZJ, Hu YM, Zhou Y, Wang R, Luo XF, Zhang BQ, Wang YL, Hu GF, Liu YQ (2022) Antifungal activity and preliminary mechanism of pristimerin against Sclerotinia sclerotiorum. Ind Crop Prod 185:115124. https://doi.org/10.1016/j.indcrop.2022.115124
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Huong, D.T.L., Son, N.T. Pristimerin: Natural Occurrence, Biosynthesis, Pharmacology, and Pharmacokinetics. Rev. Bras. Farmacogn. 34, 467–480 (2024). https://doi.org/10.1007/s43450-024-00520-z
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DOI: https://doi.org/10.1007/s43450-024-00520-z