Biodiversity Literature Repository

Submit to community
Liberated Data
Published March 31, 2020 | Version v1
Journal article Restricted

Triterpenoids from Liquidambar Fructus induced cell apoptosis via a PI3KAKT related signal pathway in SMMC7721 cancer cells

Authors/Creators

  • 1. ∗ & School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Wenhua Road 103, Shenyang, 110016, China

Description

Zhang, Hui-xing, Kang, You, Li, Ning, Wang, Hai-feng, Bao, Yong-rui, Li, Yan-wu, Li, Xue-zheng, Jiang, Zhe, Chen, Gang (2020): Triterpenoids from Liquidambar Fructus induced cell apoptosis via a PI3KAKT related signal pathway in SMMC7721 cancer cells. Phytochemistry (112228) 171: 1-9, DOI: 10.1016/j.phytochem.2019.112228, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112228

Files

Restricted

The record is publicly accessible, but files are restricted. Log in to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFC1FF956A28895F7530FFCBFF84FFC6

Has part
Figure: 10.5281/zenodo.8293989 (DOI)
Figure: 10.5281/zenodo.8293991 (DOI)
Figure: 10.5281/zenodo.8293993 (DOI)
Figure: 10.5281/zenodo.8293995 (DOI)
Figure: 10.5281/zenodo.8293997 (DOI)
Figure: 10.5281/zenodo.8294000 (DOI)
Figure: 10.5281/zenodo.8294002 (DOI)
Figure: 10.5281/zenodo.8294004 (DOI)
Figure: 10.5281/zenodo.8294008 (DOI)

References

  • Begum, S., Zehra, S.Q., Siddiqui, B.S., 2008. Two new pentacyclic triterpenoids from Lantana camara LINN. Chem. Pharm. Bull. (Tokyo). 56, 1317-1320.
  • Benyahia, S., Benayache, S., Benayache, F., Leon, F., Quintana, J., Lopez, M., Hernandez, J.C., Estevez, F., Bermejo, J., 2005. Cladocalol, a pentacyclic 28-nor-triterpene from Eucalyptus cladocalyx with cytotoxic activity. Phytochemistry 66, 627-632.
  • Caldwell, C.G., Franzblau, S.G., Suarez, E., Timmermann, B.N., 2000. Oleanane triterpenes from Junellia tridens. J. Nat. Prod. 63, 1611-1614.
  • Canavese, M., Ngo, D.T.M., Maddern, G.J., Hardingham, J.E., Price, T.J., Hauben, E., 2017. Biology and therapeutic implications of VEGF- A splice isoforms and single-- nucleotide polymorphisms in colorectal cancer. Int. J. Cancer 140, 2183-2191.
  • Castellano, L., de Correa, R.S., Martinez, E., 2002. Oleanane triterpenoids from cedrela Montana (meliaceae). Z. Naturforschung 57c, 575-578.
  • Chatterjee, P., Pezzuto, J.M., Kouzi, S.A., 1999. Glucosidation of betulinic acid by Cunninghamella species. J. Nat. Prod. 62, 761-763.
  • Chen, X.Q., Li, Y., He, J., Cheng, X., Wang, K., Li, M.M., Pan, Z.H., Peng, L.Y., Zhao, Q.S., 2011a. Triterpenoids and diterpenoids from Viburnum chingii. Chem. Pharm. Bull. 59, 496-498.
  • Chen, Y.C., Chen, C.H., Hsu, Y.H., Chen, T.H., Sue, Y.M., Cheng, C.Y., Chen, T.W., 2011b. Leptin reduces gentamicin-induced apoptosis in rat renal tubular cells via the PI3KAkt signaling pathway. Eur. J. Pharmacol. 658, 213-218.
  • Chun, L., Youfu, S., Yuru, S., 2002. A new triterpene from the fruits of Liquidambar formosana Hance-Lulutong. J. Chin. Pharm. Sci. 11, 1-4.
  • Deng, Y., Jiang, T.Y., Sheng, S., Tianasoa-Ramamonjy, M., Snyder, J.K., 1999. Remangilones A-C, new cytotoxic triterpenes from Physena madagascariensis. J. Nat. Prod. 62, 471-476.
  • Dongdong, S., Feng, Z., Jie, Q., Weixing, S., Huisen, F., Jiani, T., Liu, L., Changliang, X., Ye, Y., Haibo, C., 2018. 4'-hydroxywogonin inhibits colorectal cancer angiogenesis by disrupting PI3K/AKT signaling. Chem. Biol. Interact. 296, 26-33.
  • Evan, G.I., Vousden, K.H., 2001. Proliferation, cell cycle and apoptosis in cancer. Nature 411, 342-348.
  • Fidler, I.J., 2002. The organ microenvironment and cancer metastasis. Mol. Cells 70, 93-98.
  • Finlay, H.J., Honda, T., Gribble, G.W., Danielpour, D., Benoit, N.E., Suh, N., Williams, C., Sporn, M.B., 1997. Novel A-ring cleaved analogs of oleanolic and ursolic acids which affect growth regulation in NRP. 152 prostate cells. Bioorg. Med. Chem. Lett 7, 1769-1772.
  • Fukuyama, Y., Minami, H., Fujii, H., Tajima, M., 2002. Triterpenoids from viburnum suspensum. Phytochemistry 60, 765-768.
  • Fulda, S., 2013. Modulation of mitochondrial apoptosis by PI3K inhibitors. Mitochondrion 13, 195-198.
  • Gossan, D.P.A., Magid, A.A., Yao-Kouassi, P.A., Josse, J., Gangloff, S.C., Morjani, H., Voutquenne-Nazabadioko, L., 2016. Antibacterial and cytotoxic triterpenoids from the roots of Combretum racemosum. Fitoterapia 110, 89-95.
  • Gu, J.-Q., Park, E.J., Luyengi, L., Hawthorne, M.E., Mehta, R.G., Farnsworth, N.R., Pezzuto, J.M., Kinghorn, A.D., 2001. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity. Phytochemistry 58, 121-127.
  • He, H., Shang, X.Y., Liu, W.W., Zhang, Y., Song, S.J., 2018. Triterpenes from the fruit of Camptotheca acuminata suppress human hepatocellular carcinoma cell proliferation through apoptosis induction. Nat. Prod. Res. 1-6.
  • Ikuta, A., Kamiya, K., Satake, T., Saiki, Y., 1995. Triterpenoids from callus tissue cultures of Paeonia species. Phytochemistry 38, 1203-1207.
  • Ikuta, A., Morikawa, A., 1992. Triterpenes from Stauntonia hexaphylla callus tissues. J. Nat. Prod. 55, 1230-1233.
  • Ito, J., Chang, F.-R., Wang, H.-K., Park, Y.K., Ikegaki, M., Kilgore, N., Lee, K.-H., 2001. Anti-AIDS agents. 48. Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. J. Nat. Prod. 64, 1278-1281.
  • Janku, F., Kaseb, A.O., Tsimberidou, A.M., Wolff, R.A., Kurzrock, R., 2014. Identification of novel therapeutic targets in the PI3K/AKT/mTOR pathway in hepatocellular carcinoma using targeted next generation sequencing. Oncotarget 5, 3012-3022.
  • Jie, S.H., Jing, W.W., Yi, L.D., Ming, H.H., Lin, L.Z., 2014. A new triterpenoid isolated from fruits of Liquidambaris Fructus. Chin. Tradit. Herb. Drugs 45, 1207-1210.
  • Johnstone, R.W., Ruefli, A.A., Lowe, S.W., 2002. Apoptosis: a link between cancer genetics and chemotherapy. Cell 108, 153-164.
  • Julien, O., Wells, J.A., 2017. Caspases and their substrates. Cell Death Differ. 24, 1380-1389.
  • Kamiya, K., Yoshioka, K., Saiki, Y., Ikuta, A., Satake, T., 1997. Triterpenoids and flavonoids from Paeonia lactiflora. Phytochemistry 44, 141-144.
  • Kennedy, S.G., Kandel, E.S., Cross, T.K., Hay, N., 1999. Akt/protein kinase B inhibits cell death by preventing the release of cytochrome c from mitochondria. Mol. Cell. Biol. 19, 5800-5810.
  • Kim, R.H., Mak, T.W., 2006. Tumours and tremors: how PTEN regulation underlies both. Br. J. Canc. 94, 620-624.
  • Konno, C., Oshima, Y., Hikino, H., Yang, L.L., Yen, K.Y., 1988. Antihepatotoxic principles of Liquidambar formosana fruits. Planta Med. 54, 417-419.
  • Kuroyanagi, M., Shiotsu, M., Ebihara, T., Kawai, H., Ueno, A., Fukushima, S., 1986. Chemical studies on Viburnum awabuki K. Koch. Chem. Pharm. Bull. (Tokyo). 34, 4012-4017.
  • Lehbili, M., Alabdul, M.A., Kabouche, A., Voutquenne-Nazabadioko, L., Abedini, A., Morjani, H., Gangloff, S.C., Kabouche, Z., 2018. Antibacterial, antioxidant and cytotoxic activities of triterpenes and flavonoids from the aerial parts of Salvia barrelieri Etl. Nat. Prod. Res. 32, 2683-2691.
  • Li, C., Sun, Y.S.Y., 2002. A new triterpene from the fruits of liquidambar formosana hance-lulu-tong. J. Chin. Pharm. Sci. 11, 1-4.
  • Lin, C.-N., Tu, H.-Y., Huang, A.-M., Wei, B.-L., Gan, K.-H., Hour, T.-C., Yang, S.-C., Pu, Y.- S., Won, S.-J., 2014. Ursolic Acid Derivative and Pharmaceutical Composition Thereof. Google Patents.
  • Lin, D., Wu, J., 2015. Hypoxia inducible factor in hepatocellular carcinoma: a therapeutic target. World J. Gastroenterol. 21, 12171-12178.
  • Liu, Y.M., Liu, Y.M., Chang-Xiao, L.I., Peng-Xia, L.I., 2010. Chemical composition and antibacterial activity of volatile oil from Fructus liquidambaris. Food Sci. (N. Y.) 31, 90-93.
  • Lou, L.L., Guo, R., Cheng, Z.Y., Zhao, P., Yao, G.D., Wang, X.B., Huang, X.X., Song, S.J., 2018. Coumarins from Juglans Mandshurica Maxim and their apoptosis-inducing activities in hepatocarcinoma cells. Phytochem. Lett. 24, 15-20.
  • Ma, H., Wang, F., Jiang, J., Cheng, L., Zhang, H., Zhang, G., 2017. In vivo anti-inflammatory activity of Liquidambar formosana Hance infructescence extract. Trop. J. Pharm. Res. 16, 2403-2410.
  • Macfarlane, M., Williams, A.C., 2004. Apoptosis and disease: a life or death decision. EMBO Rep. 5, 674-678.
  • Martinez, A., Perojil, A., Rivas, F., Medina-O'Donnell, M., Parra, A., 2015. Semi-synthesis of taraxerane triterpenoids from oleanolic acid. Tetrahedron 71, 792-800.
  • Min, B.S., Kim, Y.H., Lee, S.M., Jung, H.J., Lee, J.S., Na, M.K., Lee, C.O., Lee, J.P., Bae, K., 2000. Cytotoxic triterpenes from Crataegus pinnatifida. Arch Pharm. Res. (Seoul) 23, 155-158.
  • Scalarone, D., van der Horst, J., Boon, J.J., Chiantore, O., 2003. Direct- temperature mass spectrometric detection of volatile terpenoids and natural terpenoid polymersin fresh and artificially aged resins. J. Mass Spectrom. 38, 607-617.
  • Ting, C.T., Li, W.C., Chen, C.Y., Tsai, T.H., 2015. Preventive and therapeutic role of traditional Chinese herbal medicine in hepatocellular carcinoma. J. Chin. Med. Assoc. 78, 139-144.
  • Tommasi, S., Pinto, R., Pilato, B., Paradiso, A., 2007. Molecular pathways and related target therapies in liver carcinoma. Curr. Pharmaceut. Des. 13, 3279-3287.
  • Torre, L., Bray, F., Siegel, R., Ferlay, J., Lortettieulent, J., Jemal, A., 2015. Global cancer statistics, 2012: global cancer statistics, 2012. Ca - Cancer J. Clin. 65, 87-108.
  • Vivanco, I., Sawyers, C.L., 2002. The phosphatidylinositol 3-Kinase AKT pathway in human cancer. Nat. Rev. Cancer 2, 489-501.
  • Wang, Q., Yang, H.S., 2018. The role of Pdcd4 in tumour suppression and protein translation. Biol. Cell 110, 169-177.
  • Wu, H.-R., He, X.-F., Jin, X.-J., Pan, H., Shi, Z.-N., Xu, D.-D., Yao, X.-J., Zhu, Y., 2015a. New nor-ursane type triterpenoids from Gelsemium elegans. Fitoterapia 106, 175-183.
  • Wu, X., Chung, V.C., Hui, E.P., Ziea, E.T., Ng, B.F., Ho, R.S., Tsoi, K.K., Wong, S.Y., Wu, J.C., 2015b. Effectiveness of acupuncture and related therapies for palliative care of cancer: overview of systematic reviews. Sci. Rep. 5, 28-29.
  • Yan, W., Zhang, C., Li, B., Xu, X., Liang, M., Gu, S., Chu, F., Xu, B., Ren, J., Wang, P., 2016. A Series of oleanolic acid derivatives as anti-hepatitis B virus agents: design, synthesis, and in vitro and in vivo biological evaluation. Molecules 21, 402.
  • Yang, N.-Y., Chen, J.-H., Zhou, G.-S., Tang, Y.-P., Duan, J.-A., Tian, L.-J., Liu, X.-H., 2011. Pentacyclic triterpenes from the resin of Liquidambar formosana. Fitoterapia 82, 927-931.
  • Young, L.S., Kyung, K.H., Ro, L.K., 2013. Four new triterpenes from Ilex cornuta Lindley. Can. J. Chem. 91, 382-386.
  • Zhong, Y.T., Wang, X.L., Xie, Q.J., Zhang, Y.N., 2016. Effect of the extract from leaves of Liquidambar formosana Hance on S180 cells. Gen. Mol. Res. Gmr 15, 1-8.
  • Zhou, Q., Lui, V.W., Yeo, W., 2011. Targeting the PI3K/Akt/mTOR pathway in hepatocellular carcinoma. Future Oncol. 7, 1149-1167.