Ethnopharmacology, chemodiversity, and bioactivity of Cephalotaxus medicinal plants

Chinese Journal of Natural Medicines - Tập 19 - Trang 321-338 - 2021
Da-Cheng HAO1, Xu-Dong HOU2, Xiao-Jie GU1, Pei-Gen XIAO3, Guang-Bo GE2
1Biotechnology Institute, School of Environment and Chemical Engineering, Dalian Jiaotong University, Dalian 116028, China
2Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
3Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Beijing 100193, China

Tài liệu tham khảo

Hao, 2008, Interspecific relationships and origins of Taxaceae and Cephalotaxaceae revealed by partitioned Bayesian analyses of chloroplast and nuclear DNA sequences, Plant Syst Evol, 276, 89, 10.1007/s00606-008-0069-0 Ni, 2016, Five new alkaloids from Cephalotaxus lanceolata and C. fortunei var. alpina, Nat Prod Bioprospect, 6, 149, 10.1007/s13659-016-0093-7 Ni, 2018, Bioactive norditerpenoids from Cephalotaxus fortunei var. alpina and C. lanceolata, Phytochemistry, 151, 50, 10.1016/j.phytochem.2018.04.007 Ge, 2019, 17-nor-Cephalotane-type diterpenoids from Cephalotaxus fortunei, J Nat Prod, 82, 1565, 10.1021/acs.jnatprod.9b00059 Fan, 2017, Cephanolides A−J, cephalotane-type diterpenoids from Cephalotaxus sinensis, J Nat Prod, 80, 3159, 10.1021/acs.jnatprod.7b00412 Sun, 2018, Analysis of Cephalotaxus alkaloids in Cephalotaxus hainanensis by GC-MS, J Chin Med Mater, 41, 2392 Sun, 2018, Simultaneous determination of three Cephalotaxus alkaloids in Cephalotaxus hainanensis by UPLC, Chin J Exp Tradit Med Form, 24, 47 Zhao, 2017, Diterpenoids and lignans from Cephalotaxus fortunei, J Nat Prod, 80, 356, 10.1021/acs.jnatprod.6b00802 Feng, 2019, Isolation and identification of two new compounds from the twigs and leaves of Cephalotaxus fortunei, J Nat Med, 73, 653, 10.1007/s11418-019-01308-5 Xiao, 2019, Three new biflavonoids from the branches and leaves of Cephalotaxus oliveri and their antioxidant activity, Nat Prod Res, 33, 321, 10.1080/14786419.2018.1448817 Ye, 2015, Biflavone ginkgetin, a novel Wnt inhibitor, suppresses the growth of medulloblastoma, Nat Prod Bioprospect, 5, 91, 10.1007/s13659-015-0056-4 Lai, 2020, Cephalotaxine inhibits Zika infection by impeding viral replication and stability, Biochem Biophys Res Comm, 522, 1052, 10.1016/j.bbrc.2019.12.012 Hao, 2012, Biological, chemical, and omics research of Taxus medicinal resources, Drug Develop Res, 73, 477, 10.1002/ddr.21040 Hao, 2018, Impact of drug metabolism/pharmacokinetics and their relevance upon Taxus-based drug development, Curr Drug Metab, 19, 930, 10.2174/1389200219666180523094635 Wang, 2014 Nanjing University of Chinese Medicine, 2014 Editorial board of Chinese Materia Medica, 2018 Abdelkafi, 2012, Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects, Nat Prod Rep, 29, 845, 10.1039/c2np20037f Pérard-Viret, 2017, Cephalotaxus alkaloids, The Alkaloids Chem Biol, 78, 205, 10.1016/bs.alkal.2017.07.001 Pongkitwitoon, 2018, A monoclonal antibody-based enzyme-linked immunosorbent assay for determination of homoharringtonine, Planta Med, 84, 1038, 10.1055/a-0578-8689 He, 2013, Alkaloids from Cephalotaxus lanceolata and their cytotoxicities, Chem Biodivers, 10, 584, 10.1002/cbdv.201200105 Moirangthem, 2014, HPLC analysis of harringtonine and homoharringtonine in the needles of Cephalotaxus griffithii alkaloid fraction and cytotoxic activity on chronic myelogenous leukaemia K562 cell, Nat Prod Res, 28, 1503, 10.1080/14786419.2014.913241 Yu, 2019, Chemical constituents of alkaloids part of Cephalotaxus hainanensis, Chin Tradit Herb Drugs, 50, 1541 Zhang, 2014 Sakamoto, 2018, Sodium-periodate-mediated harringtonine derivatives and their antiproliferative activity against HL-60 acute leukemia cells, J Nat Prod, 81, 34, 10.1021/acs.jnatprod.7b00541 Sakamoto, 2017, Sodium periodate-mediated conjugation of harringtonine enabling the production of a highly specific monoclonal antibody, and the development of a sensitive quantitative analysis method, Analyst, 142, 1140, 10.1039/C6AN02751B Sakamoto, 2017, Development of an indirect competitive immunochromatographic strip test for rapid detection and determination of anticancer drug, harringtonine, J Chromatogr B Analyt Technol Biomed Life Sci, 1048, 150, 10.1016/j.jchromb.2017.01.032 Li, 2007, Chromatographic fingerprint analysis of Cephalotaxus sinensis from various sources by high-performance liquid chromatography-diodearray detection-electrospray ionization-tandem mass spectrometry, J Pharm Biomed Anal, 45, 38, 10.1016/j.jpba.2007.05.027 Wu, 2016, SPE-HPLC determination of harringtonine and homoharringtonine in Cephalotaxus, Chin Tradit Patent Med, 38, 1070 Wang, 2017, Determination of total alkaloids in Cephalotaxus hainanensis by improved chromotropic acid spectrophotometry, Jiangsu Agri Sci, 45, 146 Liu, 2009, Completed preparative separation of alkaloids from Cephaltaxus fortunine by step-pH-gradient high-speed counter-current chromatography, J Chromatogr A, 1216, 4663, 10.1016/j.chroma.2009.03.083 Lin, 2018, Preparation of high purity harringtonine and taxol by high speed countercurrent chromatography and recrystallization, Anal Instrument, 184 Jiang, 2009 Chen, 2017, Abietane diterpenoids from Cephalotaxus lanceolata, Nat Prod Res, 31, 2473, 10.1080/14786419.2017.1314280 Ni, 2016, Mannolides A−C with an intact diterpenoid skeleton providing insights on the biosynthesis of antitumor Cephalotaxus troponoids, Org Lett, 18, 1880, 10.1021/acs.orglett.6b00653 Xu, 2016, Cephalotanins A−D, four norditerpenoids represent three highly rigid carbon skeletons from Cephalotaxus sinensis, Chemistry, 22, 14648, 10.1002/chem.201603373 Huang, 2020, Diterpenoids and flavonoids from the twigs of Cephalotaxus fortunei var. alpina, Chem. Biodivers, 10.1002/cbdv.202000210 Chao, 2016, Terpenoids from Flueggea virosa and their anti-hepatitis C virus activity, Phytochemistry, 128, 60, 10.1016/j.phytochem.2016.04.003 Zeng, 2015, Sesquiterpenoids from branches and leaves of Cephalotaxus lanceolata, Chin Trad Herb Drugs, 46, 320 Ahmed, 2018, A new bisabolane sesquiterpenoid and a new abietane diterpenoid from Cephalotaxus sinensis, Nat Prod Res, 32, 175, 10.1080/14786419.2017.1343323 Komoto, 2015, Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana, J Nat Med, 69, 479, 10.1007/s11418-015-0912-x Wang, 2020, Lignans from stems and leaves of Cephalotaxus fortunei, Chin Trad Herb Drugs, 51, 36 Xu, 2011, Quantitative analysis of hinokiol from cell suspension cultures of Cephalotaxus fortunei, Se Pu, 29, 567 Cisowski, 2005, Investigation of the essential oils from three Cephalotaxus species, Acta Pol Pharm, 62, 461 Liang, 2014, Physicochemical property and fatty acid profile of Cephalotaxus fortunei nut oils, J Am Oil Chem Soc, 91, 1121, 10.1007/s11746-014-2460-z Zhang, 2017, Process optimization of microwave extraction of Cephalotaxus fortunei seed oil and fatty acid composition analysis, J. Chin Cereals Oils Asso, 32, 94 Xie, 2013, Chemical components and bioactivity of volatiles from kernels of Cephalotaxus fortunei, Chin J Expt Tradit Med Form, 19, 76 Li, 2008, Determination of six trace elements in Cephalotaxus fortunei by FAAS, Lishizhen Med Mater Med Res, 19, 84 McAdam, 2018, Mesophyll cells are the main site of abscisic acid biosynthesis in water-stressed leaves, Plant Physiol, 177, 911, 10.1104/pp.17.01829 Zhang, 2001, Simultaneous multi-parameter observation of Harringtonine-treating HL-60 cells with both two-photon and confocal laser scanning microscopy, Sci China C Life Sci, 44, 383, 10.1007/BF02879605 Chen, 2019, Homoharringtonine is a safe and effective substitute for anthracyclines in children younger than 2 years old with acute myeloid leukemia, Front Med, 13, 378, 10.1007/s11684-018-0658-4 Chen, 2017, Homoharringtonine targets Smad3 and TGF-β pathway to inhibit the proliferation of acute myeloid leukemia cells, Oncotarget, 8, 40318, 10.18632/oncotarget.16956 Chen, 2019, Homoharringtonine deregulates MYC transcriptional expression by directly binding NF-κB repressing factor, Proc Natl Acad Sci U S A, 116, 2220, 10.1073/pnas.1818539116 Zhang, 2016, Homoharringtonine binds to and increases myosin-9 in myeloid leukaemia, Br J Pharmacol, 173, 212, 10.1111/bph.13359 Xie, 2006, Homoharringtonine-induced apoptosis of human leukemia HL-60 cells is associated with down-regulation of telomerase, Am J Chin Med, 34, 233, 10.1142/S0192415X06003795 Wang, 2017, Homoharringtonine suppresses imatinib resistancevia the Bcl-6/p53 pathway in chronic myeloid leukemia cell lines, Oncotarget, 8, 37594, 10.18632/oncotarget.16731 Zhou, 2013, MiR-370 sensitizes chronic myeloid leukemia K562 cells to homoharringtonine by targeting Forkhead box M1, J Transl Med, 11, 265, 10.1186/1479-5876-11-265 Meng, 2008, Homoharringtonine inhibits the AKT pathway and induces in vitro and in vivo cytotoxicity in human multiple myeloma cells, Leuk Lymphoma, 49, 1954, 10.1080/10428190802320368 Kuroda, 2008, Anti-myeloma effect of homoharringtonine with concomitant targeting of the myeloma-promoting molecules, Mcl-1, XIAP, and beta-catenin, Inter J Hematol, 87, 507, 10.1007/s12185-008-0081-8 Li, 2016, Homoharringtonine delivered by high proportion PEG of long-circulating liposomes inhibits RPMI8226 multiple myeloma cells in vitro and in vivo, Am J Transl Res, 8, 1355 Geng, 2016, Effects of the combination of decitabine and homoharringtonine in SKM-1 and Kg-1a cells, Leuk Res, 44, 17, 10.1016/j.leukres.2016.02.002 Cao, 2016, Homoharringtonine combined with aclarubicin and cytarabine synergistically induces apoptosis in t(8;21) leukemia cells and triggers caspase-3-mediated cleavage of the AML1-ETO oncoprotein, Cancer Med, 5, 3205, 10.1002/cam4.913 Chen, 2018, PI3K/Akt inhibitor LY294002 potentiates homoharringtonine antimyeloma activity in myeloma cells adhered to stromal cells and in SCID mouse xenograft, Ann Hematol, 97, 865, 10.1007/s00277-018-3247-3 Nguyen, 2018, Homoharringtonine interacts synergistically with bortezomib in NHL cells through MCL-1 and NOXA-dependent mechanisms, BMC Cancer, 18, 10.1186/s12885-018-5018-x Cao, 2015, Homoharringtonine induces apoptosis and inhibits STAT3 via IL-6/JAK1/STAT3 signal pathway in Gefitinib-resistant lung cancer cells, Sci Rep, 5, 10.1038/srep08477 Sun, 2018, Homoharringtonine regulates the alternative splicing of Bcl-x and caspase 9 through a protein phosphatase 1-dependent mechanism, BMC Comp Alter Med, 18, 164, 10.1186/s12906-018-2233-6 Yakhni, 2019, Homoharringtonine, an approved anti-leukemia drug, suppresses triple negative breast cancer growth through a rapid reduction of anti-apoptotic protein abundance, Am J Cancer Res, 9, 1043 Wang, 2018, Homoharringtonine could induce quick protein synthesis of PSMD11 through activating MEK1/ERK1/2 signaling pathway in pancreatic cancer cells, J Cell Biochem, 119, 6644, 10.1002/jcb.26847 Beranova, 2013, The plant alkaloid and anti-leukemia drug homoharringtonine sensitizes resistant human colorectal carcinoma cells to TRAIL-induced apoptosis via multiple mechanisms, Apoptosis, 18, 739, 10.1007/s10495-013-0823-9 Wang, 2019, In vitro wound healing of tumor cells: inhibition of cell migration by selected cytotoxic alkaloids, BMC Pharmacol Toxicol, 20, 4, 10.1186/s40360-018-0284-4 Quintás-Cardama, 2009, Homoharringtonine, omacetaxine mepesuccinate, and chronic myeloid leukemia circa 2009, Cancer, 115, 5382, 10.1002/cncr.24601 Al Ustwani, 2014, Omacetaxine mepesuccinate in chronic myeloid leukemia, Expert Opin Pharmacother, 15, 2397, 10.1517/14656566.2014.964642 Heiblig, 2014, Subcutaneous omacetaxine mepesuccinate in patients with chronic myeloid leukemia in tyrosine kinase inhibitor-resistant patients: review and perspectives, Leuk Res, 38, 1145, 10.1016/j.leukres.2014.05.007 Mazumder, 2018, Hydroxycoumarin OT-55 kills CML cells alone or in synergy with imatinib or Synribo: involvement of ER stress and DAMP release, Cancer Lett, 438, 197, 10.1016/j.canlet.2018.07.041 Lam, 2016, Homoharringtonine (omacetaxine mepesuccinate) as an adjunct for FLT3-ITD acute myeloid leukemia, Sci Transl Med, 8, 10.1126/scitranslmed.aaf3735 Chung, 2014, Omacetaxine for treatment-resistant or treatment-intolerant adult chronic myeloid leukemia, Am J Health Syst Pharm, 71, 279, 10.2146/ajhp130506 Eckelbarger, 2008, Synthesis of antiproliferative Cephalotaxus esters and their evaluation against several human hematopoietic and solid tumor cell lines: uncovering differential susceptibilities to multidrug resistance, Chemistry, 14, 4293, 10.1002/chem.200701998 Chen, 2018, Isoharringtonine inhibits breast cancer stem-like properties and STAT3 signaling, Biomed Pharmacother, 103, 435, 10.1016/j.biopha.2018.04.076 Ye, 2003, Synthesis and antitumor activity of the derivatives of cephalotaxine and drupacine, Acta Pharm Sin, 38, 919 Gong, 2018, Autophagy in liver carcinoma cell line HepG2 induced by cephalotaxine, J Guangdong Med Univ, 36, 351 Wang, 2004, New alkaloids and a tetraflavonoid from Cephalotaxus wilsoniana, J Nat Prod, 67, 1182, 10.1021/np0498657 Moirangthem, 2014, Cephalotaxus griffithii Hook. f. needle extract induces cell cycle arrest, apoptosis and suppression of hTERT and hTR expression on human breast cancer cells, BMC Comp Alter Med, 14, 305, 10.1186/1472-6882-14-305 Moirangthem, 2015, Essential oil of Cephalotaxus griffithii needle inhibits proliferation and migration of human cervical cancer cells: involvement of mitochondria-initiated and death receptor-mediated apoptosis pathways, Nat Prod Res, 29, 1161, 10.1080/14786419.2014.981540 Li, 2017, Homoharringtonine prevents surgery-induced epidural fibrosis through endoplasmic reticulum stress signaling pathway, Eur J Pharmacol, 815, 437, 10.1016/j.ejphar.2017.09.027 Bae, 2007, A new flavonoid glycoside from the leaf of Cephalotaxus koreana, Fitoterapia, 78, 409, 10.1016/j.fitote.2007.02.008 Moirangthem, 2012, Antioxidant, antibacterial, cytotoxic, and apoptotic activity of stem bark extracts of Cephalotaxus griffithii Hook. f, BMC Comp Alter Med, 12, 30, 10.1186/1472-6882-12-30 Park, 2017, Ester alkaloids from Cephalotaxus interfere with the 2′3′-cGAMP-induced type I interferon pathway in vitro, PLoS ONE, 12, 10.1371/journal.pone.0182701 Kim, 2019, Anti-varicella-zoster virus activity of cephalotaxine estersin vitro, J Microbiol, 57, 74, 10.1007/s12275-019-8514-z Romero, 2007, Effect of cantharidin, cephalotaxine and homoharringtonine on “in vitro” models of hepatitis B virus (HBV) and bovine viral diarrhoea virus (BVDV) replication, Planta Med, 73, 552, 10.1055/s-2007-967184 Dong, 2018, The natural compound homoharringtonine presents broad antiviral activity in vitro and in vivo, Viruses, 10, E601, 10.3390/v10110601 Wen, 2013, Nematotoxicity of drupacine and a Cephalotaxus alkaloid preparation against the plant-parasitic nematodes Meloidogyne incognita and Bursaphelenchus xylophilus, Pest Manag Sci, 69, 1026, 10.1002/ps.3548 Evanno, 2008, Further studies of the norditerpene (+)-harringtonolide isolated from Cephalotaxus harringtonia var. drupacea: absolute configuration, cytotoxic and antifungal activities, Planta Med, 74, 870, 10.1055/s-2008-1074546 Krstin, 2016, How do the alkaloids emetine and homoharringtonine kill trypanosomes? An insight into their molecular modes of action, Phytomedicine, 23, 1771, 10.1016/j.phymed.2016.10.008 Argüelles, 2016, Molecular docking and binding mode analysis of plant alkaloids as in vitro and in silico inhibitors of trypanothione reductase from Trypanosoma cruzi, Nat Prod Comm, 11, 57 Saeed, 2008, Attenuation of biochemical parameters in streptozotocin-induced diabetic rats by oral administration of extracts and fractions of Cephalotaxus sinensis, J Clin Biochem Nutr, 42, 21, 10.3164/jcbn.2008004 Li, 2007, Antihyperglycemic effect of Cephalotaxus sinensis leaves and GLUT-4 translocation facilitating activity of its flavonoid constituents, Biol Pharm Bull, 30, 1123, 10.1248/bpb.30.1123 Lee, 2006, Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana, Bioorg Med Chem Lett, 16, 2850, 10.1016/j.bmcl.2006.03.018 Yoon, 2007, Inhibitors of osteoclast differentiation from Cephalotaxus koreana, J Nat Prod, 70, 2029, 10.1021/np070327e Ma, 2015 Ma, 2020, Insecticidal activity of essential oil from Cephalotaxus sinensis and its main components against various agricultural pests, Indus Crop Prod, 150 Li, 2013, Homoharringtonine is an effective therapy for patients with polycythemia vera or essential thrombocythemia who have failed or were intolerant to hydroxycarbamide or interferon-α therapy, Int J Clin Oncol, 18, 922, 10.1007/s10147-012-0453-1 Konarev, 2008, Serine proteinase inhibitors in seeds of Cycas siamensis and other gymnosperms, Phytochemistry, 69, 2482, 10.1016/j.phytochem.2008.07.001 Watari, 2015, Homoharringtonine increases intestinal epithelial permeability by modulating specific claudin isoforms in Caco-2 cell monolayers, Eur J Pharm Biopharm, 89, 232, 10.1016/j.ejpb.2014.12.012 Liu, 2017, Preparation and in vivo safety evaluations of antileukemic homoharringtonine-loaded PEGylated liposomes, Drug Dev Ind Pharm, 43, 652, 10.1080/03639045.2016.1275670 Hao, 2017 Alasvand, 2019, Antiangiogenic effect of alkaloids, Oxid Med Cell Longev, 2019, 10.1155/2019/9475908 Li, 2007 Li, 2014 Hao, 2015