Shizukaol D, a dimeric sesquiterpene isolated from Chloranthus serratus, represses the growth of human liver cancer cells by modulating Wnt signalling pathway

PLoS ONE

Volumn 11, Issue 3, 2016, Pages

  Tang, Lisha ^a   Zhu, Hengrui ^a,b   Yang, Xianmei ^a   Xie, Fang ^a,c   Peng, Jingtao ^d   Jiang, Deke ^a,e   Xie, Jun ^a   Qi, Meiyan ^a,f   Yu, Long ^a  

^a FUDAN UNIVERSITY   (China)

^b WISTAR INSTITUTE   (United States)

^c MAYO CLINIC   (United States)

^d SHANGHAI JIAO TONG UNIVERSITY   (China)

^e NORTHSHORE UNIVERSITY HEALTHSYSTEM   (United States)

^f Shanghai Jiao Tong University Affiliated Sixth People s Hospital   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BETA CATENIN; DOXORUBICIN; FLUOROURACIL; PLANT MEDICINAL PRODUCT; SESQUITERPENE DERIVATIVE; SHIZUKAOL D; UNCLASSIFIED DRUG; WNT PROTEIN; TRITERPENE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; ATTENUATION; CANCER CELL; CELL CYCLE G1 PHASE; CHLORANTHUS SERRATUS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE TIME EFFECT RELATION; DRUG MECHANISM; FOCUS CELL LINE; GENE EXPRESSION; GROWTH INHIBITION; HEK293 CELL LINE; HEPG2 CELL LINE; HERB; HUMAN; HUMAN CELL; IC50; LIVER CANCER CELL; LIVER CANCER CELL LINE; PROTEIN EXPRESSION; QGY 7703 CELL LINE; SK HEP1 CELL LINE; SMMC 7721 CELL LINE; WNT SIGNALING PATHWAY; ANGIOSPERM; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; LIVER; LIVER NEOPLASMS; METABOLISM; PATHOLOGY; TUMOR CELL LINE;

ANGIOSPERMS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; LIVER; LIVER NEOPLASMS; TRITERPENES; WNT SIGNALING PATHWAY;

EID: 84962127797     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0152012     Document Type: Article

References (37)

1. Ferlay J, Shin HR, Bray F, Forman D, Mathers C, Parkin DM. Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008. International journal of cancer Journal international du cancer. 2010;127(12):2893-917. doi: 10.1002/ijc.25516 PMID: 21351269.
2. Bruix J, Sherman M, American Association for the Study of Liver D. Management of hepatocellular carcinoma: an update. Hepatology. 2011;53(3):1020-2. doi: 10.1002/hep. 24199 PMID: 21374666; PubMed Central PMCID: PMC3084991.
3. Abrams P, Marsh JW. Current approach to hepatocellular carcinoma. The Surgical clinics of North America. 2010;90(4):803-16. doi: 10.1016/j.suc.2010.04.010 PMID: 20637949.
4. Llovet JM, Di Bisceglie AM, Bruix J, Kramer BS, Lencioni R, Zhu AX, et al. Design and endpoints of clinical trials in hepatocellular carcinoma. Journal of the National Cancer Institute. 2008;100(10):698-711. doi: 10.1093/jnci/djn134 PMID: 18477802.
5. El-Serag HB. Hepatocellular carcinoma. The New England journal of medicine. 2011;365(12):1118-27. doi: 10.1056/NEJMra1001683 PMID: 21992124.
6. Yuan T, Zhang CR, Yang SP, Yin S, Wu WB, Dong L, et al. Sesquiterpenoids and phenylpropanoids from Chloranthus serratus. J Nat Prod. 2008;71(12):2021-5. doi: 10.1021/np800543f PMID: 19053511.
7. Zhang M, Wang J, Luo J, Wang P, Guo C, Kong L. Labdane diterpenes from Chloranthus serratus. Fitoterapia. 2013;91:95-9. doi: 10.1016/j.fitote.2013.08.015 PMID: 23994232.
8. Yuan T, Zhu RX, Yang SP, Zhang H, Zhang CR, Yue JM. Serratustones A and B representing a new dimerization pattern of two types of sesquiterpenoids from Chloranthus serratus. Organic letters. 2012;14(12):3198-201. doi: 10.1021/ol301306e PMID: 22651226.
9. Xu YJ, Tang CP, Ke CQ, Zhang JB, Weiss HC, Gesing ER, et al. Mono- and Di-sesquiterpenoids from Chloranthus spicatus. Journal of natural products. 2007;70(12):1987-90. doi: 10.1021/np070433g PMID: 18044839.
10. Kwon OE, Lee HS, Lee SW, Bae K, Kim K, Hayashi M, et al. Dimeric sesquiterpenoids isolated from Chloranthus japonicus inhibited the expression of cell adhesion molecules. Journal of ethnopharmacology. 2006;104(1-2):270-7. doi: 10.1016/j.jep. 2005.09.018 PMID: 16229979.
11. Chiu KY, Wu CC, Chia CH, Hsu SL, Tzeng YM. Inhibition of growth, migration and invasion of human bladder cancer cells by antrocin, a sesquiterpene lactone isolated from Antrodia cinnamomea, and its molecular mechanisms. Cancer letters. 2015. doi: 10.1016/j.canlet.2015.11.046 PMID: 26679052.
12. Kang YJ, Park KK, Chung WY, Hwang JK, Lee SK. Xanthorrhizol, a natural sesquiterpenoid, induces apoptosis and growth arrest in HCT116 human colon cancer cells. Journal of pharmacological sciences. 2009;111(3):276-84. PMID: 19926935.
13. Kawabata J, Fukushi Y, Tahara S, Mizutani J. Shizukaol a, a sesquiterpene dimer from Chloranthus japonicus Phytochemistry. 1990;29(7):2332-4.
14. Kawabata J, Mizutani J. Dimeric sesquiterpenoid esters from Chloranthus serratus. Phytochemistry. 1992;31(4):1293-6.
15. Zhang M, Iinuma M, Wang JS, Oyama M, Ito T, Kong LY. Terpenoids from Chloranthus serratus and their anti-inflammatory activities. J Nat Prod. 2012;75(4):694-8. doi: 10.1021/np200968p PMID: 22372956.
16. Hu R, Yan H, Hao X, Liu H, Wu J. Shizukaol D isolated from Chloranthus japonicas inhibits AMPKdependent lipid content in hepatic cells by inducing mitochondrial dysfunction. PloS one. 2013;8(8):e73527. doi: 10.1371/journal.pone.0073527 PMID: 23967345; PubMed Central PMCID: PMC3743771.
17. Liu H, Li L, Chen C, Sun L, Teng F, Huang N, et al., inventors Lindenane type sesquiterpenoids, and the preparation method and pharmaceutical application thereof.. China 2009 20091013.
18. Ford CE, Jary E, Ma SS, Nixdorf S, Heinzelmann-Schwarz VA, Ward RL. The Wnt gatekeeper SFRP4 modulates EMT, cell migration and downstream Wnt signalling in serous ovarian cancer cells. PloS one. 2013;8(1):e54362. doi: 10.1371/journal.pone.0054362 PMID: 23326605; PubMed Central PMCID: PMC3543420.
19. Heidelberger C, Chaudhuri NK, Danneberg P, Mooren D, Griesbach L, Duschinsky R, et al. Fluorinated Pyrimidines, a New Class Of Tumour-Inhibitory Compounds. Nature. 1957;179(4561):663-6. doi: 10. 1038/179663a0 PMID: WOS:A1957ZP96600022.
20. Evason KJ, Francisco MT, Juric V, Balakrishnan S, Lopez Pazmino Mdel P, Gordan JD, et al. Identification of Chemical Inhibitors of beta-Catenin-Driven Liver Tumorigenesis in Zebrafish. PLoS genetics. 2015;11(7):e1005305. doi: 10.1371/journal.pgen. 1005305 PMID: 26134322; PubMed Central PMCID: PMC4489858.
21. Sangkhathat S, Kusafuka T, Miao J, Yoneda A, Nara K, Yamamoto S, et al. In vitro RNA interference against beta-catenin inhibits the proliferation of pediatric hepatic tumors. International journal of oncology. 2006;28(3):715-22. PMID: 16465377.
22. Cragg GM, Newman DJ. Natural products: a continuing source of novel drug leads. Biochimica et biophysica acta. 2013;1830(6):3670-95. doi: 10.1016/j.bbagen. 2013.02.008 PMID: 23428572; PubMed Central PMCID: PMC3672862.
23. Newman DJ, Cragg GM. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod. 2012;75(3):311-35. doi: 10.1021/np200906s PMID: 22316239; PubMed Central PMCID: PMC3721181.
24. Zhang M, Wang JS, Wang PR, Oyama M, Luo J, Ito T, et al. Sesquiterpenes from the aerial part of Chloranthus japonicus and their cytotoxicities. Fitoterapia. 2012;83(8):1604-9. doi: 10.1016/j.fitote. 2012.09.009 PMID: 22986292.
25. Tian XH, Hou WJ, Fang Y, Fan J, Tong H, Bai SL, et al. XAV939, a tankyrase 1 inhibitior, promotes cell apoptosis in neuroblastoma cell lines by inhibiting Wnt/beta-catenin signaling pathway. Journal of experimental & clinical cancer research: CR. 2013;32:100. doi: 10.1186/1756-9966-32-100 PMID: 24308762; PubMed Central PMCID: PMC3866601.
26. Clevers H. Wnt/beta-catenin signaling in development and disease. Cell. 2006;127(3):469-80. doi: 10. 1016/j.cell.2006.10.018 PMID: 17081971.
27. Filmus J, Capurro M. Glypican-3: a marker and a therapeutic target in hepatocellular carcinoma. The FEBS journal. 2013;280(10):2471-6. doi: 10.1111/febs.12126 PMID: 23305321.
28. Li S, Mao M. Next generation sequencing reveals genetic landscape of hepatocellular carcinomas. Cancer letters. 2013;340(2):247-53. doi: 10.1016/j.canlet.2012.09.027 PMID: 23063663.
29. Parody JP, Alvarez ML, Quiroga AD, Ceballos MP, Frances DE, Pisani GB, et al. Attenuation of the Wnt/beta-catenin/TCF pathway by in vivo interferon-alpha2b (IFN-alpha2b) treatment in preneoplastic rat livers. Growth factors. 2010;28(3):166-77. doi: 10.3109/08977190903547863 PMID: 20109105.
30. Shin HW, Park SY, Lee KB, Jang JJ. Down-regulation of Wnt signaling during apoptosis of human hepatic stellate cells. Hepato-gastroenterology. 2009;56(89):208-12. PMID: 19453059.
31. Krupinski J, Ferrer I, Barrachina M, Secades JJ, Mercadal J, Lozano R. CDP-choline reduces pro-caspase and cleaved caspase-3 expression, nuclear DNA fragmentation, and specific PARP-cleaved products of caspase activation following middle cerebral artery occlusion in the rat. Neuropharmacology. 2002;42(6):846-54. PMID: 12015211.
32. MacDonald BT, Tamai K, He X. Wnt/beta-catenin signaling: components, mechanisms, and diseases. Developmental cell. 2009;17(1):9-26. doi: 10.1016/j.devcel.2009.06.016 PMID: 19619488; PubMed Central PMCID: PMC2861485.
33. Ripple MJ, Parker Struckhoff A, Trillo-Tinoco J, Li L, Margolin DA, McGoey R, et al. Activation of c-Myc and Cyclin D1 by JCV T-Antigen and beta-catenin in colon cancer. PloS one. 2014;9(9):e106257. doi: 10.1371/journal.pone.0106257 PMID: 25229241; PubMed Central PMCID: PMC4167695.
34. Koehler A, Schlupf J, Schneider M, Kraft B, Winter C, Kashef J. Loss of Xenopus cadherin-11 leads to increased Wnt/beta-catenin signaling and up-regulation of target genes c-myc and cyclin D1 in neural crest. Developmental biology. 2013;383(1):132-45. doi: 10.1016/j.ydbio.2013.08.007 PMID: 23958437.
35. Formosa R, Gruppetta M, Falzon S, Santillo G, De Gaetano J, Xuereb-Anastasi A, et al. Expression and clinical significance of Wnt players and survivin in pituitary tumours. Endocrine pathology. 2012;23(2):123-31. doi: 10.1007/s12022-012-9197-8 PMID: 22327960.
36. Maher MT, Mo R, Flozak AS, Peled ON, Gottardi CJ. Beta-catenin phosphorylated at serine 45 is spatially uncoupled from beta-catenin phosphorylated in the GSK3 domain: implications for signaling. PloS one. 2010;5(4):e10184. doi: 10.1371/journal.pone.0010184 PMID: 20419129; PubMed Central PMCID: PMC2855705.
37. Ichikawa H, Nakamura Y, Kashiwada Y, Aggarwal BB. Anticancer drugs designed by mother nature: ancient drugs but modern targets. Current pharmaceutical design. 2007;13(33):3400-16. PMID: 18045194.