Mini-Reviews in Medicinal Chemistry

Author(s): Meng Hao, Min Lv* and Hui Xu*

DOI: 10.2174/1389557520666200429100326

Andrographolide: Synthetic Methods and Biological Activities

Page: [1633 - 1652] Pages: 20

  • * (Excluding Mailing and Handling)

Abstract

Andrographolide, a labdane diterpenoid, is extracted and isolated from the plants of Andrographis paniculata. Andrographolide and its derivatives exhibited a wide range of biological properties, including anticancer activity, antibacterial activity, hepatoprotective activity, antiinflammatory activity, antiviral activity, antimalarial activity, antidiabetic activity, insecticidal activity, etc. As a continuation, this review aims at giving an overview of the recent advances (from 2015 to 2018) of andrographolide and its derivatives with regard to bioactivities, mechanisms of action, structural modifications, and structure-activity relationships.

Keywords: Andrographolide, biological activity, mechanism of action, structural modification, structure-activity relationship.

Graphical Abstract

[1]
Subramanian, R.; Zaini Asmawi, M.; Sadikun, A. A bitter plant with a sweet future? A comprehensive review of an oriental medicinal plant: Andrographis paniculata. Phytochem. Rev., 2011, 11, 39-75.
[http://dx.doi.org/10.1007/s11101-011-9219-z]
[2]
Lim, J.C.; Chan, T.K.; Ng, D.S.; Sagineedu, S.R.; Stanslas, J.; Wong, W.S. Andrographolide and its analogues: Versatile bioactive molecules for combating inflammation and cancer. Clin. Exp. Pharmacol. Physiol., 2012, 39(3), 300-310.
[http://dx.doi.org/10.1111/j.1440-1681.2011.05633.x] [PMID: 22017767]
[3]
Sharma, V.; Sharma, T.; Kaul, S.; Kapoor, K.K.; Dhar, M.K. Anticancer potential of labdane diterpenoid lactone “andrographolide” and its derivatives: A semi-synthetic approach. Phytochem. Rev., 2016, 16, 513-526.
[http://dx.doi.org/10.1007/s11101-016-9478-9]
[4]
Matsuda, T.; Kuroyanagi, M.; Sugiyama, S.; Umehara, K.; Ueno, A.; Nishi, K. Cell differentiation-inducing diterpenes from Andrographis paniculata Nees. Chem. Pharm. Bull. (Tokyo), 1994, 42(6), 1216-1225.
[http://dx.doi.org/10.1248/cpb.42.1216] [PMID: 8069972]
[5]
Pholphana, N.; Rangkadilok, N.; Thongnest, S.; Ruchirawat, S.; Ruchirawat, M.; Satayavivad, J. Determination and variation of three active diterpenoids in Andrographis paniculata (Burm.f.). Nees. Phytochem. Anal., 2004, 15(6), 365-371.
[http://dx.doi.org/10.1002/pca.789] [PMID: 15595451]
[6]
Kumar, R.A.; Sridevi, K.; Kumar, N.V.; Nanduri, S.; Rajagopal, S. Anticancer and immunostimulatory compounds from Andrographis paniculata. J. Ethnopharmacol., 2004, 92(2-3), 291-295.
[http://dx.doi.org/10.1016/j.jep.2004.03.004] [PMID: 15138014]
[7]
Rajagopal, S.; Kumar, R.A.; Deevi, D.S.; Satyanarayana, C.; Rajagopalan, R. Andrographolide, a potential cancer therapeutic agent isolated from Andrographis paniculata. J. Exp. Ther. Oncol., 2003, 3(3), 147-158.
[http://dx.doi.org/10.1046/j.1359-4117.2003.01090.x] [PMID: 14641821]
[8]
Das, B.; Chowdhury, C.; Kumar, D.; Sen, R.; Roy, R.; Das, P.; Chatterjee, M. Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent. Bioorg. Med. Chem. Lett., 2010, 20(23), 6947-6950.
[http://dx.doi.org/10.1016/j.bmcl.2010.09.126] [PMID: 20974534]
[9]
Sirion, U.; Kasemsook, S.; Suksen, K.; Piyachaturawat, P.; Suksamrarn, A.; Saeeng, R. New substituted C-19-andrographolide analogues with potent cytotoxic activities. Bioorg. Med. Chem. Lett., 2012, 22(1), 49-52.
[http://dx.doi.org/10.1016/j.bmcl.2011.11.085] [PMID: 22154665]
[10]
Wei, S.; Tang, Y.B.; Hua, H.; Ohkoshi, E.; Goto, M.; Wang, L.T.; Lee, K.H.; Xiao, Z. Discovery of novel andrographolide derivatives as cytotoxic agents. Bioorg. Med. Chem. Lett., 2013, 23(14), 4056-4060.
[http://dx.doi.org/10.1016/j.bmcl.2013.05.061] [PMID: 23768904]
[11]
Wu, Z.W.; Xu, H.W.; Dai, G.F.; Liu, M.J.; Zhu, L.P.; Wu, J.; Wang, Y.N.; Wu, F.J.; Zhao, D.; Gao, M.F.; Nie, S.S.; Han, W.; Song, J.H.; Liu, H.M. Improved inhibitory activities against tumor-cell migration and invasion by 15-benzylidene substitution derivatives of andrographolide. Bioorg. Med. Chem. Lett., 2013, 23(23), 6421-6426.
[http://dx.doi.org/10.1016/j.bmcl.2013.09.049] [PMID: 24120543]
[12]
Chen, D.; Song, Y.; Lu, Y.; Xue, X. Synthesis and in vitro cytotoxicity of andrographolide-19-oic acid analogues as anti-cancer agents. Bioorg. Med. Chem. Lett., 2013, 23(11), 3166-3169.
[http://dx.doi.org/10.1016/j.bmcl.2013.04.010] [PMID: 23628335]
[13]
Wang, J.; Tan, X.F.; Nguyen, V.S.; Yang, P.; Zhou, J.; Gao, M.; Li, Z.; Lim, T.K.; He, Y.; Ong, C.S.; Lay, Y.; Zhang, J.; Zhu, G.; Lai, S.L.; Ghosh, D.; Mok, Y.K.; Shen, H.M.; Lin, Q. A quantitative chemical proteomics approach to profile the specific cellular targets of andrographolide, a promising anticancer agent that suppresses tumor metastasis. Mol. Cell. Proteomics, 2014, 13(3), 876-886.
[http://dx.doi.org/10.1074/mcp.M113.029793] [PMID: 24445406]
[14]
Wang, Z.; Yu, P.; Zhang, G.; Xu, L.; Wang, D.; Wang, L.; Zeng, X.; Wang, Y. Design, synthesis and antibacterial activity of novel andrographolide derivatives. Bioorg. Med. Chem., 2010, 18(12), 4269-4274.
[http://dx.doi.org/10.1016/j.bmc.2010.04.094] [PMID: 20493714]
[15]
Jiang, X.; Yu, P.; Jiang, J.; Zhang, Z.; Wang, Z.; Yang, Z.; Tian, Z.; Wright, S.C.; Larrick, J.W.; Wang, Y. Synthesis and evaluation of antibacterial activities of andrographolide analogues. Eur. J. Med. Chem., 2009, 44(7), 2936-2943.
[http://dx.doi.org/10.1016/j.ejmech.2008.12.014] [PMID: 19152987]
[16]
Shen, T.; Yang, W.S.; Yi, Y.S.; Sung, G.H.; Rhee, M.H.; Poo, H.; Kim, M.Y.; Kim, K.W.; Kim, J.H.; Cho, J.Y. AP-1/IRF-3 targeted anti-inflammatory activity of andrographolide isolated from Andrographis paniculata. Evid. Based Complement. Alternat. Med., 2013.2013210736
[http://dx.doi.org/10.1155/2013/210736] [PMID: 23840248]
[17]
Tang, C.; Gu, G.; Wang, B.; Deng, X.; Zhu, X.; Qian, H.; Huang, W. Design, synthesis, and biological evaluation of andrographolide derivatives as potent hepatoprotective agents. Chem. Biol. Drug Des., 2014, 83(3), 324-333.
[http://dx.doi.org/10.1111/cbdd.12246] [PMID: 24118795]
[18]
Maiti, K.; Mukherjee, K.; Murugan, V.; Saha, B.P.; Mukherjee, P.K. Enhancing bioavailability and hepatoprotective activity of andrographolide from Andrographis paniculata, a well-known medicinal food, through its herbosome. J. Sci. Food Agric., 2010, 90(1), 43-51.
[http://dx.doi.org/10.1002/jsfa.3777] [PMID: 20355010]
[19]
Uttekar, M.M.; Das, T.; Pawar, R.S.; Bhandari, B.; Menon, V. Nutan; Gupta, S.K.; Bhat, S.V. Anti-HIV activity of semisynthetic derivatives of andrographolide and computational study of HIV-1 gp120 protein binding. Eur. J. Med. Chem., 2012, 56, 368-374.
[http://dx.doi.org/10.1016/j.ejmech.2012.07.030] [PMID: 22858223]
[20]
Sheeja, K.; Shihab, P.K.; Kuttan, G. Antioxidant and anti-inflammatory activities of the plant Andrographis paniculata Nees. Immunopharmacol. Immunotoxicol., 2006, 28(1), 129-140.
[http://dx.doi.org/10.1080/08923970600626007] [PMID: 16684672]
[21]
Suebsasana, S.; Pongnaratorn, P.; Sattayasai, J.; Arkaravichien, T.; Tiamkao, S.; Aromdee, C. Analgesic, antipyretic, anti-inflammatory and toxic effects of andrographolide derivatives in experimental animals. Arch. Pharm. Res., 2009, 32(9), 1191-1200.
[http://dx.doi.org/10.1007/s12272-009-1902-x] [PMID: 19784573]
[22]
Xu, H.W.; Dai, G.F.; Liu, G.Z.; Wang, J.F.; Liu, H.M. Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors. Bioorg. Med. Chem., 2007, 15(12), 4247-4255.
[http://dx.doi.org/10.1016/j.bmc.2007.03.063] [PMID: 17428667]
[23]
Liu, Z.; Law, W.K.; Wang, D.; Nie, X.; Sheng, D.; Song, G.; Guo, K.; Wei, P.; Ouyang, P.; Wong, C.W.; Zhou, G.C. Synthesis and discovery of andrographolide derivatives as non-steroidal farnesoid X receptor (FXR) antagonists. RSC Advances, 2014, 4, 13533-13545.
[http://dx.doi.org/10.1039/C3RA46715E]
[24]
Yoopan, N.; Thisoda, P.; Rangkadilok, N.; Sahasitiwat, S.; Pholphana, N.; Ruchirawat, S.; Satayavivad, J. Cardiovascular effects of 14-deoxy-11,12-didehydroandrographolide and Andrographis paniculata extracts. Planta Med., 2007, 73(6), 503-511.
[http://dx.doi.org/10.1055/s-2007-967181] [PMID: 17650544]
[25]
Thakur, A.K.; Chatterjee, S.S.; Kumar, V. Adaptogenic potential of andrographolide: An active principle of the king of bitters (Andrographis paniculata). J. Tradit. Complement. Med., 2014, 5(1), 42-50.
[http://dx.doi.org/10.1016/j.jtcme.2014.10.002] [PMID: 26151008]
[26]
Chan, S.J.; Wong, W.S.F.; Wong, P.T.H.; Bian, J.S. Neuroprotective effects of andrographolide in a rat model of permanent cerebral ischaemia. Br. J. Pharmacol., 2010, 161(3), 668-679.
[http://dx.doi.org/10.1111/j.1476-5381.2010.00906.x] [PMID: 20880404]
[27]
Li, M.L.; Cui, J.; Zhang, Y.B.; Li, F.F. Antifeedant activities of tutin and andrographolide derivatives against Mythimna separata. Heterocycles, 2011, 83, 1129-1137.
[http://dx.doi.org/10.3987/COM-11-12150]
[28]
Pratheeshkumar, P.; Sheeja, K.; Kuttan, G. Andrographolide induces apoptosis in B16F-10 melanoma cells by inhibiting NF-κB-mediated bcl-2 activation and modulating p53-induced caspase-3 gene expression. Immunopharmacol. Immunotoxicol., 2012, 34(1), 143-151.
[http://dx.doi.org/10.3109/08923973.2011.588233] [PMID: 21682651]
[29]
Zhou, J.; Zhang, S.; Ong, C.N.; Shen, H.M. Critical role of pro-apoptotic Bcl-2 family members in andrographolide-induced apoptosis in human cancer cells. Biochem. Pharmacol., 2006, 72(2), 132-144.
[http://dx.doi.org/10.1016/j.bcp.2006.04.019] [PMID: 16740251]
[30]
Zhang, Q.Q.; Zhou, D.L.; Ding, Y.; Liu, H.Y.; Lei, Y.; Fang, H.Y.; Gu, Q.L.; He, X.D.; Qi, C.L.; Yang, Y.; Lan, T.; Li, J.C.; Gong, P.; Wu, X.Y.; Yang, X.; Li, W.D.; Wang, L.J. Andrographolide inhibits melanoma tumor growth by inactivating the TLR4/NF-κB signaling pathway. Melanoma Res., 2014, 24(6), 545-555.
[http://dx.doi.org/10.1097/CMR.0000000000000117] [PMID: 25244079]
[31]
Reabroi, S.; Chairoungdua, A.; Saeeng, R.; Kasemsuk, T.; Saengsawang, W.; Zhu, W.; Piyachaturawat, P. A silyl andrographolide analogue suppresses Wnt/β-catenin signaling pathway in colon cancer. Biomed. Pharmacother., 2018, 101, 414-421.
[http://dx.doi.org/10.1016/j.biopha.2018.02.119] [PMID: 29501763]
[32]
Zhang, R.; Zhao, J.; Xu, J.; Jiao, D.X.; Wang, J.; Gong, Z.Q.; Jia, J.H. Andrographolide suppresses proliferation of human colon cancer SW620 cells through the TLR4/NF-κB/MMP-9 signaling pathway. Oncol. Lett., 2017, 14(4), 4305-4310.
[http://dx.doi.org/10.3892/ol.2017.6669] [PMID: 28943944]
[33]
Su, M.; Qin, B.; Liu, F.; Chen, Y.; Zhang, R. Andrographolide enhanced 5-fluorouracil-induced antitumor effect in colorectal cancer via inhibition of c-MET pathway. Drug Des. Devel. Ther., 2017, 11, 3333-3341.
[http://dx.doi.org/10.2147/DDDT.S140354] [PMID: 29200829]
[34]
Peng, T.; Hu, M.; Wu, T.T.; Zhang, C.; Chen, Z.; Huang, S.; Zhou, X.H. Andrographolide suppresses proliferation of nasopharyngeal carcinoma cells via attenuating NF-κB pathway. BioMed Res. Int., 2015.2015735056
[http://dx.doi.org/10.1155/2015/735056] [PMID: 25861643]
[35]
Lim, S.C.; Jeon, H.J.; Kee, K.H.; Lee, M.J.; Hong, R.; Han, S.I. Andrographolide induces apoptotic and non-apoptotic death and enhances tumor necrosis factor-related apoptosis-inducing ligand-mediated apoptosis in gastric cancer cells. Oncol. Lett., 2017, 13(5), 3837-3844.
[http://dx.doi.org/10.3892/ol.2017.5923] [PMID: 28529596]
[36]
Kang, X.; Zheng, Z.; Liu, Z.; Wang, H.; Zhao, Y.; Zhang, W.; Shi, M.; He, Y.; Cao, Y.; Xu, Q.; Peng, C.; Huang, Y. Liposomal codelivery of doxorubicin and andrographolide inhibits breast cancer growth and metastasis. Mol. Pharm., 2018, 15(4), 1618-1626.
[http://dx.doi.org/10.1021/acs.molpharmaceut.7b01164] [PMID: 29498868]
[37]
Gao, H.; Wang, J. Andrographolide inhibits multiple myeloma cells by inhibiting the TLR4/NF-κB signaling pathway. Mol. Med. Rep., 2016, 13(2), 1827-1832.
[http://dx.doi.org/10.3892/mmr.2015.4703] [PMID: 26707811]
[38]
Ekalaksananan, T.; Sookmai, W.; Fangkham, S.; Pientong, C.; Aromdee, C.; Seubsasana, S.; Kongyingyoes, B. Activity of andrographolide and its derivatives on HPV16 pseudovirus infection and viral oncogene expression in cervical carcinoma cells. Nutr. Cancer, 2015, 67(4), 687-696.
[http://dx.doi.org/10.1080/01635581.2015.1019630] [PMID: 25837567]
[39]
Zhang, C.; Qiu, X. Andrographolide radiosensitizes human ovarian cancer SKOV3 xenografts due to an enhanced apoptosis and autophagy. Tumour Biol., 2015, 36(11), 8359-8365.
[http://dx.doi.org/10.1007/s13277-015-3578-9] [PMID: 26014516]
[40]
Yang, W.; Zhao, J.; Wang, Y.; Xu, H.; Wu, Z.; Hu, Y.; Jiang, K.; Shen, P.; Ma, C.; Guan, Z.; Zhang, Y.; Ma, J.; Shang, N.; Yan, G.; Wang, Z.; Dai, G. In vivo inhibitory activity of andrographolide derivative ADN-9 against liver cancer and its mechanisms involved in inhibition of tumor angiogenesis. Toxicol. Appl. Pharmacol., 2017, 327, 1-12.
[http://dx.doi.org/10.1016/j.taap.2017.04.022] [PMID: 28438631]
[41]
Wei, R.J.; Zhang, X.S.; He, D.L. Andrographolide sensitizes prostate cancer cells to TRAIL-induced apoptosis. Asian J. Androl., 2018, 20(2), 200-204.
[http://dx.doi.org/10.4103/aja.aja_30_17] [PMID: 28869219]
[42]
Wang, Z.M.; Kang, Y.H.; Yang, X.; Wang, J.F.; Zhang, Q.; Yang, B.X.; Zhao, K.L.; Xu, L.P.; Yang, L.P.; Ma, J.X.; Huang, G.H.; Cai, J.; Sun, X.C. Andrographolide radiosensitizes human esophageal cancer cell line ECA109 to radiation in vitro. Dis. Esophagus, 2016, 29(1), 54-61.
[http://dx.doi.org/10.1111/dote.12255] [PMID: 25059546]
[43]
Yang, S.L.; Kuo, F.H.; Chen, P.N.; Hsieh, Y.H.; Yu, N.Y.; Yang, W.E.; Hsieh, M.J.; Yang, S.F. Andrographolide suppresses the migratory ability of human glioblastoma multiforme cells by targeting ERK1/2-mediated matrix metalloproteinase-2 expression. Oncotarget, 2017, 8(62), 105860-105872.
[http://dx.doi.org/10.18632/oncotarget.22407] [PMID: 29285298]
[44]
Zhang, H.T.; Yang, J.; Liang, G.H.; Gao, X.J.; Sang, Y.; Gui, T.; Liang, Z.J.; Tam, M.S.; Zha, Z.G. Andrographolide induces cell cycle arrest and apoptosis of chondrosarcoma by targeting TCF-1/SOX9 axis. J. Cell. Biochem., 2017, 118(12), 4575-4586.
[http://dx.doi.org/10.1002/jcb.26122] [PMID: 28485543]
[45]
Hsieh, M.J.; Chen, J.C.; Yang, W.E.; Chien, S.Y.; Chen, M.K.; Lo, Y.S.; Hsi, Y.T.; Chuang, Y.C.; Lin, C.C.; Yang, S.F. Dehydroandrographolide inhibits oral cancer cell migration and invasion through NF-κB-, AP-1-, and SP-1-modulated matrix metalloproteinase-2 inhibition. Biochem. Pharmacol., 2017, 130, 10-20.
[http://dx.doi.org/10.1016/j.bcp.2017.01.011] [PMID: 28131848]
[46]
Tsai, H.R.; Yang, L.M.; Tsai, W.J.; Chiou, W.F. Andrographolide acts through inhibition of ERK1/2 and Akt phosphorylation to suppress chemotactic migration. Eur. J. Pharmacol., 2004, 498(1-3), 45-52.
[http://dx.doi.org/10.1016/j.ejphar.2004.07.077] [PMID: 15363974]
[47]
Sukumari-Ramesh, S.; Bentley, J.N.; Laird, M.D.; Singh, N.; Vender, J.R.; Dhandapani, K.M. Dietary phytochemicals induce p53- and caspase-independent cell death in human neuroblastoma cells. Int. J. Dev. Neurosci., 2011, 29(7), 701-710.
[http://dx.doi.org/10.1016/j.ijdevneu.2011.06.002] [PMID: 21704149]
[48]
Shi, M.D.; Lin, H.H.; Chiang, T.A.; Tsai, L.Y.; Tsai, S.M.; Lee, Y.C.; Chen, J.H. Andrographolide could inhibit human colorectal carcinoma Lovo cells migration and invasion via down-regulation of MMP-7 expression. Chem. Biol. Interact., 2009, 180(3), 344-352.
[http://dx.doi.org/10.1016/j.cbi.2009.04.011] [PMID: 19426720]
[49]
Suzuki, E.; Daniels, T.R.; Helguera, G.; Penichet, M.L.; Umezawa, K.; Bonavida, B. Inhibition of NF-kappaB and Akt pathways by an antibody-avidin fusion protein sensitizes malignant B-cells to cisplatin-induced apoptosis. Int. J. Oncol., 2010, 36(5), 1299-1307.
[PMID: 20372806]
[50]
Calabrese, C.; Berman, S.H.; Babish, J.G.; Ma, X.; Shinto, L.; Dorr, M.; Wells, K.; Wenner, C.A.; Standish, L.J. A phase I trial of andrographolide in HIV positive patients and normal volunteers. Phytother. Res., 2000, 14(5), 333-338.
[http://dx.doi.org/10.1002/1099-1573(200008)14:5<333:AID-PTR584>3.0.CO;2-D] [PMID: 10925397]
[51]
Manni, S.; Brancalion, A.; Mandato, E.; Tubi, L.Q.; Colpo, A.; Pizzi, M.; Cappellesso, R.; Zaffino, F.; Di Maggio, S.A.; Cabrelle, A.; Marino, F.; Zambello, R.; Trentin, L.; Adami, F.; Gurrieri, C.; Semenzato, G.; Piazza, F. Protein kinase CK2 inhibition down modulates the NF-κB and STAT3 survival pathways, enhances the cellular proteotoxic stress and synergistically boosts the cytotoxic effect of bortezomib on multiple myeloma and mantle cell lymphoma cells. PLoS One, 2013, 8(9)e75280
[http://dx.doi.org/10.1371/journal.pone.0075280] [PMID: 24086494]
[52]
Luo, W.; Liu, Y.; Zhang, J.; Luo, X.; Lin, C.; Guo, J. Andrographolide inhibits the activation of NF-κB and MMP-9 activity in H3255 lung cancer cells. Exp. Ther. Med., 2013, 6(3), 743-746.
[http://dx.doi.org/10.3892/etm.2013.1196] [PMID: 24137258]
[53]
Wang, L.J.; Zhou, X.; Wang, W.; Tang, F.; Qi, C.L.; Yang, X.; Wu, S.; Lin, Y.Q.; Wang, J.T.; Geng, J.G. Andrographolide inhibits oral squamous cell carcinogenesis through NF-κB inactivation. J. Dent. Res., 2011, 90(10), 1246-1252.
[http://dx.doi.org/10.1177/0022034511418341] [PMID: 21841043]
[54]
Yang, S.H.; Wang, S.M.; Syu, J.P.; Chen, Y.; Wang, S.D.; Peng, Y.S.; Kuo, M.F.; Kung, H.N. Andrographolide induces apoptosis of C6 glioma cells via the ERK-p53-caspase 7-PARP pathway. BioMed Res. Int., 2014, 2014312847
[http://dx.doi.org/10.1155/2014/312847] [PMID: 25162007]
[55]
Yang, T.; Yao, S.; Zhang, X.; Guo, Y. Andrographolide inhibits growth of human T-cell acute lymphoblastic leukemia Jurkat cells by downregulation of PI3K/AKT and upregulation of p38 MAPK pathways. Drug Des. Devel. Ther., 2016, 10, 1389-1397.
[http://dx.doi.org/10.2147/DDDT.S94983] [PMID: 27114702]
[56]
Chen, X.; Zhang, J.; Yuan, L.; Lay, Y.; Wong, Y.K.; Lim, T.K.; Ong, C.S.; Lin, Q.; Wang, J.; Hua, Z. Andrographolide Suppresses MV4-11 cell proliferation through the inhibition of FLT3 signaling, fatty acid synthesis and cellular iron uptake. Molecules, 2017, 22(9), 22.
[http://dx.doi.org/10.3390/molecules22091444] [PMID: 28858244]
[57]
Shi, L.; Zhang, G.; Zheng, Z.; Lu, B.; Ji, L. Andrographolide reduced VEGFA expression in hepatoma cancer cells by inactivating HIF-1α: The involvement of JNK and MTA1/HDCA. Chem. Biol. Interact., 2017, 273, 228-236.
[http://dx.doi.org/10.1016/j.cbi.2017.06.024] [PMID: 28651835]
[58]
Chen, S.; Hu, H.; Miao, S.; Zheng, J.; Xie, Z.; Zhao, H. Anti-tumor effect of cisplatin in human oral squamous cell carcinoma was enhanced by andrographolide via upregulation of phospho-p53 in vitro and in vivo. Tumour Biol., 2017, 39(5)1010428317705330
[http://dx.doi.org/10.1177/1010428317705330] [PMID: 28513299]
[59]
Ding, Y.; Chen, L.; Wu, W.; Yang, J.; Yang, Z.; Liu, S. Andrographolide inhibits influenza A virus-induced inflammation in a murine model through NF-κB and JAK-STAT signaling pathway. Microbes Infect., 2017, 19(12), 605-615.
[http://dx.doi.org/10.1016/j.micinf.2017.08.009] [PMID: 28889969]
[60]
Zhan, J.Y.X.; Wang, X.F.; Liu, Y.H.; Zhang, Z.B.; Wang, L.; Chen, J.N.; Huang, S.; Zeng, H.F.; Lai, X.P. Andrographolide sodium bisulfate prevents UV-induced skin photoaging through inhibiting oxidative stress and inflammation. Mediators Inflamm., 2016.20163271451
[http://dx.doi.org/10.1155/2016/3271451] [PMID: 26903706]
[61]
Yen, C.C.; Chen, Y.C.; Wu, M.T.; Wang, C.C.; Wu, Y.T. Nanoemulsion as a strategy for improving the oral bioavailability and anti-inflammatory activity of andrographolide. Int. J. Nanomedicine, 2018, 13, 669-680.
[http://dx.doi.org/10.2147/IJN.S154824] [PMID: 29440893]
[62]
Tan, W.S.D.; Liao, W.; Zhou, S.; Wong, W.S.F. Is there a future for andrographolide to be an anti-inflammatory drug? Deciphering its major mechanisms of action. Biochem. Pharmacol., 2017, 139, 71-81.
[http://dx.doi.org/10.1016/j.bcp.2017.03.024] [PMID: 28377280]
[63]
Li, Y.; He, S.; Tang, J.; Ding, N.; Chu, X.; Cheng, L.; Ding, X.; Liang, T.; Feng, S.; Rahman, S.U.; Wang, X.; Wu, J. Andrographolide Inhibits Inflammatory Cytokines Secretion in LPS-Stimulated RAW264.7 Cells through Suppression of NF-κB/MAPK Signaling Pathway. Evid. Based Complement. Alternat. Med., 2017, 20178248142
[http://dx.doi.org/10.1155/2017/8248142] [PMID: 28676833]
[64]
Fleming, S.B. Viral inhibition of the IFN-induced JAK/STAT signaling pathway: Development of live attenuated vaccines by mutation of viral-encoded IFN-antagonists. Vaccines (Basel), 2016, 4(3), 4.
[http://dx.doi.org/10.3390/vaccines4030023] [PMID: 27367734]
[65]
Wang, Y.J.; Wang, J.T.; Fan, Q.X.; Geng, J.G. Andrographolide inhibits NF-kappaBeta activation and attenuates neointimal hyperplasia in arterial restenosis. Cell Res., 2007, 17(11), 933-941.
[http://dx.doi.org/10.1038/cr.2007.89] [PMID: 17943075]
[66]
Li, Z.Z.; Tan, J.P.; Wang, L.L.; Li, Q.H. Andrographolide benefits rheumatoid arthritis via inhibiting MAPK pathways. Inflammation, 2017, 40(5), 1599-1605.
[http://dx.doi.org/10.1007/s10753-017-0600-y] [PMID: 28584977]
[67]
Neha, T.; Rawal, U.M. Hepatoprotective and toxicological evaluation of Andrographis paniculata on severe liver damage. Indian J. Pharmacol., 2000, 32, 288-293.
[68]
Chua, L.S. Review on liver inflammation and antiinflammatory activity of Andrographis paniculata for hepatoprotection. Phytother. Res., 2014, 28(11), 1589-1598.
[http://dx.doi.org/10.1002/ptr.5193] [PMID: 25043965]
[69]
Jaruchotikamol, A.; Jarukamjorn, K.; Sirisangtrakul, W.; Sakuma, T.; Kawasaki, Y.; Nemoto, N. Strong synergistic induction of CYP1A1 expression by andrographolide plus typical CYP1A inducers in mouse hepatocytes. Toxicol. Appl. Pharmacol., 2007, 224(2), 156-162.
[http://dx.doi.org/10.1016/j.taap.2007.07.008] [PMID: 17825862]
[70]
Akowuah, G.A.; Zhari, I.; Mariam, A.; Yam, M.F. Absorption of andrographolides from Andrographis paniculata and its effect on CCl(4)-induced oxidative stress in rats. Food Chem. Toxicol., 2009, 47(9), 2321-2326.
[http://dx.doi.org/10.1016/j.fct.2009.06.022] [PMID: 19540299]
[71]
Alam, K.; Nagi, M.N.; Badary, O.A.; Al-Shabanah, O.A.; Al-Rikabi, A.C.; Al-Bekairi, A.M. The protective action of thymol against carbon tetrachloride hepatotoxicity in mice. Pharmacol. Res., 1999, 40(2), 159-163.
[http://dx.doi.org/10.1006/phrs.1999.0472] [PMID: 10433875]
[72]
Chen, J.X.; Xue, H.J.; Ye, W.C.; Fang, B.H.; Liu, Y.H.; Yuan, S.H.; Yu, P.; Wang, Y.Q. Activity of andrographolide and its derivatives against influenza virus in vivo and in vitro. Biol. Pharm. Bull., 2009, 32(8), 1385-1391.
[http://dx.doi.org/10.1248/bpb.32.1385] [PMID: 19652378]
[73]
Nanduri, S.; Nyavanandi, V.K.; Thunuguntla, S.S.; Kasu, S.; Pallerla, M.K.; Ram, P.S.; Rajagopal, S.; Kumar, R.A.; Ramanujam, R.; Babu, J.M.; Vyas, K.; Devi, A.S.; Reddy, G.O.; Akella, V. Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents. Bioorg. Med. Chem. Lett., 2004, 14(18), 4711-4717.
[http://dx.doi.org/10.1016/j.bmcl.2004.06.090] [PMID: 15324893]
[74]
Govindachari, T.R.; Suresh, G.; Gopalakrishan, G.; Daniel Wesley, S.; Pradeep Singh, N.D. Antifeedant activity of some diterpenoids. Fitoterapia, 1999, 70, 269-274.
[http://dx.doi.org/10.1016/S0367-326X(99)00033-7]
[75]
Hermawan, W.; Nakajima, S.; Tsukuda, R.; Fujisaki, K.; Nakasuji, F. Isolation of an antifeedant compound from Andrographis paniculata (Acanthaceae) against the Diamondback Moth, Plutella xylostella (Lepidoptera:Yponomeutidae). Appl. Entomol. Zool., 1997, 32, 551-559.
[http://dx.doi.org/10.1303/aez.32.551]
[76]
Hermawan, W.; Tsukuda, R.; Nakajima, S.; Fujisaki, K.; Nakasuji, F. Oviposition deterrent activity of andrographolide against the diamondback moth (DBM), Plutella xylostella(Lepidoptera:Yponomeutidae). Appl. Entomol. Zool., 1998, 33, 239-241.
[http://dx.doi.org/10.1303/aez.33.239]
[77]
Edwin, E.; Vasantha-Srinivasan, P.; Senthil-Nathan, S.; Thanigaivel, A.; Ponsankar, A.; Selin-Rani, S.; Kalaivani, K.; Hunter, W.B.; Duraipandiyan, V.; AlDhabi, N.A. Effect of andrographolide on phosphatases activity and cytotoxicity against Spodoptera litura. Invert. Surviv. J., 2016, 13, 153-163.
[78]
Lee, J.C.; Tseng, C.K.; Young, K.C.; Sun, H.Y.; Wang, S.W.; Chen, W.C.; Lin, C.K.; Wu, Y.H. Andrographolide exerts anti-hepatitis C virus activity by up-regulating haeme oxygenase-1 via the p38 MAPK/Nrf2 pathway in human hepatoma cells. Br. J. Pharmacol., 2014, 171(1), 237-252.
[http://dx.doi.org/10.1111/bph.12440] [PMID: 24117426]
[79]
Banerjee, M.; Parai, D.; Chattopadhyay, S.; Mukherjee, S.K. Andrographolide: Antibacterial activity against common bacteria of human health concern and possible mechanism of action. Folia Microbiol. (Praha), 2017, 62(3), 237-244.
[http://dx.doi.org/10.1007/s12223-017-0496-9] [PMID: 28097636]
[80]
Islam, M.T. Andrographolide, a new hope in the prevention and treatment of metabolic syndrome. Front. Pharmacol., 2017, 8, 571.
[http://dx.doi.org/10.3389/fphar.2017.00571] [PMID: 28878680]
[81]
Das, S.; Mishra, K.P.; Ganju, L.; Singh, S.B. Andrographolide - A promising therapeutic agent, negatively regulates glial cell derived neurodegeneration of prefrontal cortex, hippocampus and working memory impairment. J. Neuroimmunol., 2017, 313, 161-175.
[http://dx.doi.org/10.1016/j.jneuroim.2017.11.003] [PMID: 29146293]
[82]
Ambili, R.; Janam, P. Saneesh Babu, P.S.; Prasad, M.; Vinod, D.; Anil Kumar, P.R.; Kumary, T.V.; Asha Nair, S.; Radhakrishna Pillai, M. An ex vivo evaluation of the efficacy of andrographolide in modulating differential expression of transcription factors and target genes in periodontal cells and its potential role in treating periodontal diseases. J. Ethnopharmacol., 2017, 196, 160-167.
[http://dx.doi.org/10.1016/j.jep.2016.12.029] [PMID: 27993634]
[83]
Ding, Y.; Shi, C.; Chen, L.; Ma, P.; Li, K.; Jin, J.; Zhang, Q.; Li, A. Effects of andrographolide on postoperative cognitive dysfunction and the association with NF-κB/MAPK pathway. Oncol. Lett., 2017, 14(6), 7367-7373.
[http://dx.doi.org/10.3892/ol.2017.7088] [PMID: 29344175]
[84]
Zhao, Y.; Huang, P.; Chen, Z.; Zheng, S.W.; Yu, J.Y.; Shi, C. Clinical application analysis of andrographolide total ester sulfonate injection, a traditional chinese medicine licensed in China. J. Huazhong Univ. Sci. Technolog. Med. Sci., 2017, 37(2), 293-299.
[http://dx.doi.org/10.1007/s11596-017-1730-z] [PMID: 28397057]
[85]
Hsu, Y.H.; Hsu, Y.L.; Liu, S.H.; Liao, H.C.; Lee, P.X.; Lin, C.H.; Lo, L.C.; Fu, S.L. Development of a bifunctional andrographolide-based chemical probe for pharmacological study. PLoS One, 2016, 11(4)e0152770
[http://dx.doi.org/10.1371/journal.pone.0152770] [PMID: 27035713]
[86]
Qiao, Y.; Huang, Y.; Feng, F.; Chen, Z.G. Efficient enzymatic synthesis and antibacterial activity of andrographolide glycoside. Process Biochem., 2016, 51, 675-680.
[http://dx.doi.org/10.1016/j.procbio.2016.02.008]
[87]
Zeng, M.; Jiang, W.; Tian, Y.; Hao, J.; Cao, Z.; Liu, Z.; Fu, C.; Zhang, P.; Ma, J. Andrographolide inhibits arrhythmias and is cardioprotective in rabbits. Oncotarget, 2017, 8(37), 61226-61238.
[http://dx.doi.org/10.18632/oncotarget.18051] [PMID: 28977859]
[88]
Roy, P.; Das, S.; Bera, T.; Mondol, S.; Mukherjee, A. Andrographolide nanoparticles in leishmaniasis: Characterization and in vitro evaluations. Int. J. Nanomedicine, 2010, 5, 1113-1121.
[PMID: 21270962]
[89]
Zhang, C.; Gui, L.; Xu, Y.; Wu, T.; Liu, D. Preventive effects of andrographolide on the development of diabetes in autoimmune diabetic NOD mice by inducing immune tolerance. Int. Immunopharmacol., 2013, 16(4), 451-456.
[http://dx.doi.org/10.1016/j.intimp.2013.05.002] [PMID: 23707775]
[90]
Tan, W.S.D.; Liao, W.; Peh, H.Y.; Vila, M.; Dong, J.; Shen, H.M.; Wong, W.S.F. Andrographolide simultaneously augments Nrf2 antioxidant defense and facilitates autophagic flux blockade in cigarette smoke-exposed human bronchial epithelial cells. Toxicol. Appl. Pharmacol., 2018, 360, 120-130.
[http://dx.doi.org/10.1016/j.taap.2018.10.005] [PMID: 30291937]
[91]
Nguyen, V.S.; Loh, X.Y.; Wijaya, H.; Wang, J.; Lin, Q.; Lam, Y.; Wong, W.S.; Mok, Y.K. Specificity and inhibitory mechanism of andrographolide and its analogues as antiasthma agents on NF-κB p50. J. Nat. Prod., 2015, 78(2), 208-217.
[http://dx.doi.org/10.1021/np5007179] [PMID: 25615020]
[92]
Prabu, A.; Hassan, S. Prabuseenivasan; Shainaba, A.S.; Hanna, L.E.; Kumar, V. Andrographolide: A potent antituberculosis compound that targets Aminoglycoside 2′-N-acetyltransferase in Mycobacterium tuberculosis. J. Mol. Graph. Model., 2015, 61, 133-140.
[http://dx.doi.org/10.1016/j.jmgm.2015.07.001] [PMID: 26245695]
[93]
Nosáľová, G.; Majee, S.K.; Ghosh, K.; Raja, W.; Chatterjee, U.R.; Jureček, L.; Ray, B. Antitussive arabinogalactan of Andrographis paniculata demonstrates synergistic effect with andrographolide. Int. J. Biol. Macromol., 2014, 69, 151-157.
[http://dx.doi.org/10.1016/j.ijbiomac.2014.05.030] [PMID: 24857874]
[94]
Seo, J.Y.; Pyo, E.; An, J.P.; Kim, J.; Sung, S.H.; Oh, W.K. Andrographolide Activates Keap1/Nrf2/ARE/HO-1 Pathway in HT22 Cells and Suppresses Microglial Activation by Aβ42 through Nrf2-Related Inflammatory Response. Mediators Inflamm., 2017, 20175906189
[http://dx.doi.org/10.1155/2017/5906189] [PMID: 28373747]
[95]
Tan, W.S.; Peh, H.Y.; Liao, W.; Pang, C.H.; Chan, T.K.; Lau, S.H.; Chow, V.T.; Wong, W.S. Cigarette Smoke-Induced Lung Disease Predisposes to More Severe Infection with Nontypeable Haemophilus influenzae: Protective effects of andrographolide. J. Nat. Prod., 2016, 79(5), 1308-1315.
[http://dx.doi.org/10.1021/acs.jnatprod.5b01006] [PMID: 27104764]
[96]
Zhu, P.Y.; Yin, W.H.; Wang, M.R.; Dang, Y.Y.; Ye, X.Y. Andrographolide suppresses melanin synthesis through Akt/GSK3β/β-catenin signal pathway. J. Dermatol. Sci., 2015, 79(1), 74-83.
[http://dx.doi.org/10.1016/j.jdermsci.2015.03.013] [PMID: 25869056]
[97]
Xia, B.; Xu, B.; Sun, Y.; Xiao, L.; Pan, J.; Jin, H.; Tong, P. The effects of Liuwei Dihuang on canonical Wnt/β-catenin signaling pathway in osteoporosis. J. Ethnopharmacol., 2014, 153(1), 133-141.
[http://dx.doi.org/10.1016/j.jep.2014.01.040] [PMID: 24530448]
[98]
D’Errico, J.A.; MacNeil, R.L.; Takata, T.; Berry, J.; Strayhorn, C.; Somerman, M.J. Expression of bone associated markers by tooth root lining cells, in situ and in vitro. Bone, 1997, 20(2), 117-126.
[http://dx.doi.org/10.1016/S8756-3282(96)00348-1] [PMID: 9028535]
[99]
Hakki, S.S.; Wang, D.; Franceschi, R.T.; Somerman, M.J. Bone sialoprotein gene transfer to periodontal ligament cells may not be sufficient to promote mineralization in vitro or in vivo. J. Periodontol., 2006, 77(2), 167-173.
[http://dx.doi.org/10.1902/jop.2006.050057] [PMID: 16460240]
[100]
Yu, B.; Chang, J.; Liu, Y.; Li, J.; Kevork, K.; Al-Hezaimi, K.; Graves, D.T.; Park, N.H.; Wang, C.Y. Wnt4 signaling prevents skeletal aging and inflammation by inhibiting nuclear factor-κB. Nat. Med., 2014, 20(9), 1009-1017.
[http://dx.doi.org/10.1038/nm.3586] [PMID: 25108526]
[101]
Jiang, T.; Zhou, B.; Huang, L.; Wu, H.; Huang, J.; Liang, T.; Liu, H.; Zheng, L.; Zhao, J. Andrographolide exerts pro-osteogenic effect by activation of Wnt/β-Catenin signaling pathway in vitro. Cell. Physiol. Biochem., 2015, 36(6), 2327-2339.
[http://dx.doi.org/10.1159/000430196] [PMID: 26279437]
[102]
Li, B.; Hu, R.Y.; Sun, L.; Luo, R.; Lu, K.H.; Tian, X.B. Potential role of andrographolide in the proliferation of osteoblasts mediated by the ERK signaling pathway. Biomed. Pharmacother., 2016, 83, 1335-1344.
[http://dx.doi.org/10.1016/j.biopha.2016.07.033] [PMID: 27571877]
[103]
Agarwal, D. Cytotoxic andrographolide derivatives: Structure activity relationship studies. Int. J. Pharm. Chem. Sci., 2015, 4, 185-190.
[104]
Chinthala, Y.K.M.; Sharma, P.; Kvn, S.S.; Jonnala, K.; Arigari, N.K.; Khan, F.; Oh, S. Synthesis and cytotoxicity evaluation of novel andrographolide-1,2,3-triazole derivatives. J. Heter. Chem., 2016, 53, 1902-1910.
[http://dx.doi.org/10.1002/jhet.2505]
[105]
Song, Y.; Xin, Z.; Wan, Y.; Li, J.; Ye, B.; Xue, X. Synthesis and anticancer activity of some novel indolo3,2-bandrographolide derivatives as apoptosis-inducing agents. Eur. J. Med. Chem., 2015, 90, 695-706.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.017] [PMID: 25506809]
[106]
Duan, H.; Jing, M.; Li, Z.; Zhang, Z.; Wang, Y.; Xu, L.; Yu, P. Synthesis and biological evaluation of andrographolide derivatives as potential anti-inflammatory agents. J. Pharm. Biomed. Sci., 2017, 07, 94-99.
[107]
Liu, Y.; Liang, R.M.; Ma, Q.P.; Xu, K.; Liang, X.Y.; Huang, W.; Sutton, R.; Ding, J.; O’Neil, P.M.; Cheng, C.R. Synthesis of thioether andrographolide derivatives and their inhibitory effect against cancer cells. MedChemComm, 2017, 8(6), 1268-1274.
[http://dx.doi.org/10.1039/C7MD00169J] [PMID: 30108837]
[108]
Devendar, P.; Nayak, V.L.; Yadav, D.K.; Kumar, A.N.; Kumar, J.K.; Satya Srinivas, K.V.N.; Sridhar, B.; Khan, F.; Sastry, K.P.; Ramakrishna, S. Synthesis and evaluation of anticancer activity of novel andrographolide derivatives. MedChemComm, 2015, 6, 898-904.
[http://dx.doi.org/10.1039/C4MD00566J]
[109]
Peng, Y.; Li, J.; Sun, Y.; Chan, J.Y.W.; Sheng, D.; Wang, K.; Wei, P.; Ouyang, P.; Wang, D.; Lee, S.M.Y.; Zhou, G.C. SAR studies of 3,14,19-derivatives of andrographolide on anti-proliferative activity to cancer cells and toxicity to zebrafish: An in vitro and in vivo study. RSC Advances, 2015, 5, 22510-22526.
[http://dx.doi.org/10.1039/C5RA00090D]
[110]
Patil, H.S.; Jadhav, D.D.; Paul, A.; Mulani, F.A.; Karegaonkar, S.J.; Thulasiram, H.V. Regioselective and efficient enzymatic synthesis of antimicrobial andrographolide derivatives. Bioorg. Med. Chem. Lett., 2018, 28(6), 1132-1137.
[http://dx.doi.org/10.1016/j.bmcl.2018.01.007] [PMID: 29475585]
[111]
Nie, X.; Chen, S.R.; Wang, K.; Peng, Y.; Wang, Y.T.; Wang, D.; Wang, Y.; Zhou, G.C. Attenuation of innate immunity by andrographolide derivatives through NF-κB signaling pathway. Sci. Rep., 2017, 7(1), 4738.
[http://dx.doi.org/10.1038/s41598-017-04673-x] [PMID: 28680097]
[112]
Li, F.; Li, X.M.; Sheng, D.; Chen, S.R.; Nie, X.; Liu, Z.; Wang, D.; Zhao, Q.; Wang, Y.; Wang, Y.; Zhou, G.C. Discovery and preliminary SAR of 14-aryloxy-andrographolide derivatives as antibacterial agents with immunosuppressant activity. RSC Advances, 2018, 8, 9440-9456.
[http://dx.doi.org/10.1039/C8RA01063C]
[113]
Kandanur, S.G.; Golakoti, N.R.; Nanduri, S. Synthesis and in vitro cytotoxicity of novel C-12 substituted-14-deoxy-andrographolide derivatives as potent anti-cancer agents. Bioorg. Med. Chem. Lett., 2015, 25(24), 5781-5786.
[http://dx.doi.org/10.1016/j.bmcl.2015.10.053] [PMID: 26561364]
[114]
Kandanur, S.G.S.; Nanduri, S.; Golakoti, N.R. Synthesis and biological evaluation of new C-12(α/β)-(N-) sulfamoyl-phenylamino-14-deoxy-andrographolide derivatives as potent anti-cancer agents. Bioorg. Med. Chem. Lett., 2017, 27(13), 2854-2862.
[http://dx.doi.org/10.1016/j.bmcl.2017.04.033] [PMID: 28527822]
[115]
Siva, S.R.T.; Nyavanandi, V.K.; Nanduri, S. A facile route for the synthesis of limonidilactone analogues from andrographolide. Tetrahedron Lett., 2004, 45, 9357-9360.
[http://dx.doi.org/10.1016/j.tetlet.2004.10.135]
[116]
Sirion, U.; Kasemsuk, T.; Piyachaturawat, P.; Suksen, K.; Suksamrarn, A.; Saeeng, R. Synthesis and cytotoxic activity of 14-deoxy-12-hydroxyandrographolide analogs. Med. Chem. Res., 2017, 26, 1653-1663.
[http://dx.doi.org/10.1007/s00044-017-1881-2]
[117]
Yuan, L.; Zhang, C.; Sun, H.; Liu, Q.; Huang, J.; Sheng, L.; Lin, B.; Wang, J.; Chen, L. The semi-synthesis of novel andrographolide analogues and anti-influenza virus activity evaluation of their derivatives. Bioorg. Med. Chem. Lett., 2016, 26(3), 769-773.
[http://dx.doi.org/10.1016/j.bmcl.2015.12.100] [PMID: 26791013]
[118]
Song, Z.; Huang, S.; He, Y.; Li, J.; Lin, K.; Xue, X. Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives. Eur. J. Med. Chem., 2018, 157, 805-816.
[http://dx.doi.org/10.1016/j.ejmech.2018.08.046] [PMID: 30144698]
[119]
Xu, H.W.; Zhang, J.; Liu, H.M.; Wang, J.F. Synthesis of andrographolide cyclophosphate derivatives and their antitumor activities. Synth. Commun., 2006, 36, 407-414.
[http://dx.doi.org/10.1080/00397910500377594]
[120]
Huang, X.; Zhang, B.; Xu, H. Synthesis of andrographolide-related esters as insecticidal and acaricidal agents. Bioorg. Med. Chem. Lett., 2018, 28(3), 360-364.
[http://dx.doi.org/10.1016/j.bmcl.2017.12.038] [PMID: 29287959]
[121]
Nateewattana, J.; Saeeng, R.; Kasemsook, S.; Suksen, K.; Dutta, S.; Jariyawat, S.; Chairoungdua, A.; Suksamrarn, A.; Piyachaturawat, P. Inhibition of topoisomerase II α activity and induction of apoptosis in mammalian cells by semi-synthetic andrographolide analogues. Invest. New Drugs, 2013, 31(2), 320-332.
[http://dx.doi.org/10.1007/s10637-012-9868-9] [PMID: 22899371]
[122]
Sombut, S.; Bunthawong, R.; Sirion, U.; Kasemsuk, T.; Piyachaturawat, P.; Suksen, K.; Suksamrarn, A.; Saeeng, R. Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma. Bioorg. Med. Chem. Lett., 2017, 27(23), 5139-5143.
[http://dx.doi.org/10.1016/j.bmcl.2017.10.063] [PMID: 29097170]
[123]
Wang, Z.; Chen, Y.; Wu, F. Oligo-polyethene glycol (PEG)-modified 14-deoxy-11,12-didehydroandrographolide derivatives: synthesis, solubility and anti-bacterial activity. Tetrahedron, 2016, 72, 2265-2270.
[http://dx.doi.org/10.1016/j.tet.2016.03.025]
[124]
Wang, Z.; He, R.; Chen, Y.; Wu, F. Regio-selective PEGylation of 14-deoxy-11,12-didehydroandrographolide and their biological evaluation. Tetrahedron, 2016, 72, 5909-5913.
[http://dx.doi.org/10.1016/j.tet.2016.08.024]
[125]
Kasemsuk, T.; Piyachaturawat, P.; Bunthawong, R.; Sirion, U.; Suksen, K.; Suksamrarn, A.; Saeeng, R. One-pot three steps cascade synthesis of novel isoandrographolide analogues and their cytotoxic activity. Eur. J. Med. Chem., 2017, 138, 952-963.
[http://dx.doi.org/10.1016/j.ejmech.2017.07.035] [PMID: 28755636]
[126]
Luo, Y.; Wang, K.; Zhang, M.H.; Zhang, D.Y.; Wu, Y.C.; Wu, X.M.; Hua, W.Y. Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation on cytotoxic activities. Bioorg. Med. Chem. Lett., 2015, 25(11), 2421-2424.
[http://dx.doi.org/10.1016/j.bmcl.2015.03.086] [PMID: 25913115]
[127]
Aromdee, C. Andrographolide: progression in its modifications and applications - a patent review (2012 - 2014). Expert Opin. Ther. Pat., 2014, 24(10), 1129-1138.
[http://dx.doi.org/10.1517/13543776.2014.956084] [PMID: 25231887]
[128]
Aromdee, C. Modifications of andrographolide to increase some biological activities: A patent review (2006 - 2011). Expert Opin. Ther. Pat., 2012, 22(2), 169-180.
[http://dx.doi.org/10.1517/13543776.2012.661718] [PMID: 22329509]
[129]
Chen, H.; Ma, Y.B.; Huang, X.Y.; Geng, C.A.; Zhao, Y.; Wang, L.J.; Guo, R.H.; Liang, W.J.; Zhang, X.M.; Chen, J.J. Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents. Bioorg. Med. Chem. Lett., 2014, 24(10), 2353-2359.
[http://dx.doi.org/10.1016/j.bmcl.2014.03.060] [PMID: 24731274]