Andrographolide and its analogues: Versatile bioactive molecules for combating inflammation and cancer

Clinical and Experimental Pharmacology and Physiology

Volumn 39, Issue 3, 2012, Pages 300-310

  Lim, Jonathan Chee Woei ^a,b   Chan, Tze Khee ^a   Ng, David Sw ^a   Sagineedu, Sreenivasa R ^b   Stanslas, Johnson ^b   Wong, Ws Fred ^a,c  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^c NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Andrographis paniculata; Apoptosis; Cell cycle; Cytokines; Nuclear factor B; Signal transducer and activator of transcription 3

Indexed keywords

11,12 DIDEHYDRO 14 DEOXYANDROGRAPHOLIDE; 19 O ACETYLANHYDROANDROGRAPHOLIDE; 3,19 BENZYLIDENEANDROGRAPHOLIDE; 3,19 O DIACETYLANDROGRAPHOLIDE; 8,17 EPOXYANDROGRAPHOLIDE; ANDROGRAPHIS PANICULATA EXTRACT; ANDROGRAPHOLIDE; ANDROGRAPHOLIDE COMPLEX; ANDROGRAPHOLIDE DERIVATIVE; ANTIDIABETIC AGENT; ANTIINFLAMMATORY AGENT; BISANDROGRAPHOLIDE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYTOTOXIC AGENT; DEHYDROANDROGRAPHOLIDE; ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERCELLULAR ADHESION MOLECULE 1; ISOANDROGRAPHOLIDE; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE KINASE 2; NEOANDROGRAPHOLIDE; PARACETAMOL; PROTEIN KINASE B; STAT3 PROTEIN; SUPPRESSOR OF CYTOKINE SIGNALING 3; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ABSENCE OF SIDE EFFECTS; ALLERGIC ASTHMA; ANDROGRAPHIS PANICULATA; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BRAIN ISCHEMIA; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CHEMOTAXIS; DOWN REGULATION; DRUG MEGADOSE; DRUG POTENCY; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; FEVER; HISTORY OF MEDICINE; HUMAN; INTRACELLULAR SIGNALING; LIPID PEROXIDATION; MACROPHAGE; NEUROPROTECTION; NONHUMAN; OXIDATIVE STRESS; PERITONITIS; PHARYNGITIS; PHARYNGOTONSILITIS; PROTEIN EXPRESSION; RHEUMATOID ARTHRITIS; SEPTIC SHOCK; SORE THROAT; STRUCTURE ACTIVITY RELATION; TONSILLITIS; TUMOR VASCULARIZATION; UPPER RESPIRATORY TRACT INFECTION;

ANDROGRAPHIS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIOLOGICAL AGENTS; DITERPENES; HUMANS; INFLAMMATION MEDIATORS; NEOPLASMS; PLANT EXTRACTS;

EID: 84857381831     PISSN: 03051870     EISSN: 14401681     Source Type: Journal    
DOI: 10.1111/j.1440-1681.2011.05633.x     Document Type: Article

References (94)

1. Ajaya K, Sridevi K, Vijaya K, Nanduri S, Rajagopal S. Anticancer and immunostimulatory compounds from Andrographis paniculata. J. Ethnopharmacol. 2004; 92: 291-5.
2. Kleipool RJC. Constituents of Andrographis paniculata Nees. Nature 1952; 169: 33-4.
3. Chan WR, Taylor DR, Willis CR, Bodden RL, Fehlhaber HW. The structure and stereochemistry of neoandrographolide, a diterpene glucoside from Andrographis paniculata Nees. Tetrahedron 1971; 27: 5081-91.
4. Balmain A, Connolly JD. Minor diterpenoid constituents of Andrographis paniculata Nees. J. Chem. Soc. Perkin Trans. 1974; 1: 1247-51.
5. Reddy MK, Reddy MVB, Gunasekar D, Murthy MM, Caux C, Bodo B. A flavone and an unusual 23-carbon terpenoid from Andrographis paniculata. Phytochemistry 2004; 62: 1271-5.
6. Matsuda T, Kuroyanagi M, Sugiyama S, Umehara K, Ueno A, Nishi K. Cell differentiation-inducing diterpenes from Andrographis paniculata Nees. Chem. Pharm. Bull. 1994; 42: 1216-25.
7. Siripong P, Kongkathip B, Preechanukool K, Picha P, Tunsuwan K, Taylor WC. Cytotoxic diterpenoid constituents from A. paniculata Nees leaves. J. Sci. Soc. Thai. 1992; 18: 187-94.
8. Dua VK, Ojha VP, Roy R. et al. Anti-malarial activity of some xanthones isolated from the roots of Andrographis paniculata. J. Ethnopharmacol. 2004; 95: 247-51.
9. Smith AB, Toder BH, Carroll PJ, Donohue J. Andrographolide: An X-ray crystallographic analysis. J. Chem. Crystallogr. 1982; 12: 309-19.
10. Shen YH, Li RT, Xiao WLet al.ent-Labdane diterpenoids from Andrographis paniculata. J. Nat. Prod. 2005; 69: 319-22.
11. Pramanick S, Banerjee S, Achari B et al. Andropanolide and isoandrographolide, minor diterpenoids from Andrographis paniculata: Structure and X-ray crystallographic analysis. J. Nat. Prod. 2005; 69: 403-5.
12. Bhaskar RMV, Kishore PH, Rao CV, Gunasekar D, Caux C, Bodo B. New 2′-oxygenated flavonoids from Andrographis affinis. J. Nat. Prod. 2004; 66: 295-7.
13. Jalal MAF, Overton KH, Rycroft DS. Formation of three new flavones by differentiating callus cultures of Andrographis paniculata. Phytochemistry 1979; 18: 149-51.
14. World Health Organization. Herba andrographidis. In World Health Organization: (eds). WHO Monographs on Selected Medicinal Plants, Vol. 2. World Health Organization, Geneva. 2002; 12-25.
15. Handa SS. Indian Herbal Pharmacopoeia, Vol. 1. IDMA, Mumbai. 1998.
16. Chao WW, Lin BF. Isolation and identification of bioactive compounds in Andrographis paniculata (Chuanxinlian). Chin. Med. 2010; 5: 17.
17. Abeysekera AM, De Silva KTD, Silva WSJ, Ratnayake S, Labadie RP. Proton and carbon-13 NMR spectral analysis of andrographolide. Fitoterapia 1988; 59: 501-5.
18. Nanduri S, Nyavanandi VK, Sanjeeva RTS et al. Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents. Bioorg. Med. Chem. Lett. 2004; 14: 4711-7.
19. Xu HW, Zhang J, Liu HM, Wang JF. Synthesis of andrographolide cyclophosphate derivatives and their antitumor activities. Cheminformatics 2006; 37: 407-14.
20. Siva SRT, Vijay KN, Srinivas N. A facile route for the synthesis of limonidilactone analogues from andrographolide. Tetrahedron Lett. 2004; 45: 9357-60.
21. Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM. Synthesis of andrographolide derivatives. A new family of alpha-glucosidase inhibitors. Bioorg. Med. Chem. 2007; 15: 4247-55.
22. Jada SR, Hamzah AS, Lajis NH, Saad MS, Stevens MFG, Stanslas J. Semisynthesis and cytotoxic activities of andrographolide analogues. J. Enzyme Inhib. Med. Chem. 2006; 21: 145-55.
23. Jada SR, Subur GS, Matthews C et al. Semisynthesis and in vitro anticancer activities of andrographolide analogues. Phytochemistry 2007; 68: 904-12.
24. 1 arrest and apoptosis. Br. J. Pharmacol. 2008; 155: 641-54.
25. Das B, Chowdhury C, Kumar D et al. Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent. Bioorg. Med. Chem. Lett. 2010; 20: 6947-50.
26. He XJ, Wang YH, Hu H, Wu YX, Zeng XB. Novel bioconversion products of andrographolide by Aspergillus ochraceus and their cytotoxic activities against human tumor cell lines. J. Mol. Catal. B Enzym. 2011; 68: 89-93.
27. Jiang X, Yu P, Jiang J et al. Synthesis and evaluation of antibacterial activities of andrographolide analogues. Eur. J. Med. Chem. 2009; 44: 2936-43.
28. Nathan C. Points of control in inflammation. Nature 2002; 420: 846-52.
29. Medzhitov R. Origin and physiological roles of inflammation. Nature 2008; 454: 428-35.
30. Nakanishi C, Toi M. Nuclear factor-κB inhibitors as sensitizers to anticancer drugs. Nat. Rev. Cancer 2005; 5: 297-309.
31. Tsai HR, Yang LM, Tsai WJ, Chiou WF. Andrographolide acts through inhibition of ERK1/2 and Akt phosphorylation to suppress chemotactic migration. Eur. J. Pharmacol. 2004; 498: 45-52.
32. Abu-Ghefreh AA, Canatan H, Ezeamuzie CI. In vitro and in vivo anti-inflammatory effects of andrographolide. Int. Immunopharmacol. 2009; 9: 313-8.
33. Chandrasekaran CV, Thiyagarajan P, Deepak HB, Agarwal A. In vitro modulation of LPS/calcimycin induced inflammatory and allergiic mediators by pure compounds of Andrographis paniculata (king of bitters) extract. Int. Immunopharmacol. 2011; 11: 79-84.
34. Lee KC, Chang HH, Chung YH, Lee TY. Andrographolide acts as an anti-inflammatory agent in LPS-stimulated RAW264.7 macrophages by inhibiting STAT3-mediated suppression of the NF-κB pathway. J. Ethnopharmacol. 2011; 135: 678-84.
35. Ley K, Laudanna C, Cybulsky MI, Nourshargh S. Getting to the site of inflammation: The leukocyte adhesion cascade updated. Nat. Rev. Immunol. 2007; 7: 678-89.
36. Habtemariam S. Andrographolide inhibits the TNF-α-induced upregulation of ICAM-1 expression and endothelial-monocyte adhesion. Phytother. Res. 1998; 12: 37-40.
37. Chao CY, Lii CK, Tsai IT et al. Andrographolide inhibits ICAM-1 expression and NF-κB activation in TNF-α-treated EA.hy926 cells. J. Agric. Food. Chem. 2011; 59: 5263-71.
38. Shen YC, Chen CF, Chiou WF. Andrographolide prevents oxygen radical production by human neutrophils: Possible mechanism (s) involved in its anti-inflammatory effect. Br. J. Pharmacol. 2002; 135: 399-406.
39. Shen YC, Chen CF, Chiou WF. Suppression of rat neutrophil reactive oxygen species production and adhesion by the diterpenoid lactone andrographolide. Planta Med. 2000; 66: 314-7.
40. Chiou WF, Chen CF, Lin JJ. Mechanisms of suppression of inducible nitric oxide synthase (iNOS) expression in RAW 264.7 cells by andrographolide. Br. J. Pharmacol. 2000; 129: 1553-60.
41. Ying L, Hofseth LJ. An emerging role for endothelial nitric oxide synthase in chronic inflammation and cancer. Cancer Res. 2007; 67: 1407-10.
42. Hussain SP, He P, Subleski J et al. Nitric oxide is a key component in inflammation-accelerated tumorigenesis. Cancer Res. 2008; 68: 7130-6.
43. Parichatikanond W, Suthisisang C, Dhepakson P, Herunsalee A. Study of anti-inflammatory activities of the pure compounds from Andrographis paniculata (burm.f.) Nees and their effects on gene expression. Int. Immunopharmacol. 2010; 10: 1361-74.
44. Bao Z, Guan S, Cheng Cet al.A novel antiinflammatory role for andrographolide in asthma via inhibition of the nuclear factor-κB pathway. Am. J. Respir. Crit. Care Med. 2009; 179: 657-65.
45. Guan SP, Kong LR, Cheng C, Lim JCW, Wong WSF. Protective role of 14-deoxy-11, 12-didehydroandrographolide, a noncytotoxic analogue of andrographolide, in allergic airway inflammation. J. Nat. Prod. 2011; 74: 1484-90.
46. Lin FL, Wu SJ, Lee SC, Ng LT. Antioxidant, antioedema and analgesic activities of Andrographis paniculata extracts and their active constituent andrographolide. Phytother. Res. 2009; 23: 958-64.
47. 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. Pharmacol. Res. 2009; 32: 1191-200.
48. Chan SJ, Wong WSF, Wong PTH, Bian JS. Neuroprotective effects of andrographolide in a rat model of permanent cerebral ischaemia. Br. J. Pharmacol. 2010; 161: 668-79.
49. Chao WW, Kuo YH, Lin BF. Anti-inflammatory activity of new compounds from Andrographis paniculata by NF-κB transactivation inhibition. J. Agric. Food. Chem. 2010; 58: 2505-12.
50. Cho ML, Moon YM, Heo YJet al.NF-κB inhibition leads to increased synthesis and secretion of MIF in human CD4+ T cells. Immunol. Lett. 2009; 123: 21-30.
51. Xia YF, Ye BQ, Li YD et al. Andrographolide attenuates inflammation by inhibition of NF-κB activation through covalent modification of reduced cysteine 62 of p50. J. Immunol. 2004; 173: 4207-17.
52. Hsieh CY, Hsu MJ, Hsiao G et al. Andrographolide enhances NF-κB subunit p65 ser (536) dephosphorylation through activation of protein phosphatase 2A in vascular smooth muscle cells. J. Biol. Chem. 2011; 286: 5942-55.
53. Hidalgo MA, Romero A, Figueroa J et al. Andrographolide interferes with binding of NF-κB to DNA in HL-60-derived neutrophilic cells. Br. J. Pharmacol. 2005; 144: 680-6.
54. Jin L, Shi G, Ning G, Li X, Zhang Z. Andrographolide attenuates tumor necrosis factor-α-induced insulin resistance in 3T3-L1 adipocytes. Mol. Cell. Endocrinol. 2011; 332: 134-9.
55. Zhang Z, Jiang J, Yu P, Zeng X, Larrick J, Wang Y. Hypoglycemic and beta cell protective effects of andrographolide analogue for diabetes treatment. J. Transl. Med. 2009; 7: 62.
56. Balkwill F, Charles KA, Mantovani A. Smoldering and polarized inflammation in the initiation and promotion of malignant disease. Cancer Cell 2005; 7: 211-7.
57. Zhou BS, Zhang H, Damelin M, Geles KG, Grindley JC, Dirks PB. Tumour-initiating cells: Challenges and opportunities for anticancer drug discovery. Nat. Rev. Drug. Discov. 2009; 8: 806-23.
58. Harvey K, Tapon N. The Salvador-Warts-Hippo pathway: An emerging tumour-suppressor network. Nat. Rev. Cancer 2007; 7: 182-91.
59. Rajagopal S, Kumar RA, Deevi DS, Satyanarayana C, Rajagopalan R. Andrographolide, a potential cancer therapeutic agent isolated from Andrographis paniculata. J. Exp. Ther. Oncol. 2004; 3: 147-58.
60. Shi MD, Lin HH, Lee YC, Chao JK, Lin RA, Chen JH. Inhibition of cell-cycle progression in human colorectal carcinoma Lovo cells by andrographolide. Chem. Biol. Interact. 2008; 174: 201-10.
61. Manikam SD, Stanslas J. Andrographolide inhibits growth of acute promyelocytic leukaemia cells by inducing retinoic acid receptor-independent cell differentiation and apoptosis. J. Pharm. Pharmacol. 2009; 61: 69-78.
62. Cheung HY, Cheung SH, Li J et al. Andrographolide isolated from Andrographis paniculata induces cell cycle arrest and mitochondrial-mediated apoptosis in human leukemic HL-60 cells. Planta Med. 2005; 71: 1106-11.
63. Shen KK, Liu TY, Xu C, Ji LL, Wang ZT. Andrographolide inhibits hepatoma cells growth and affects the expression of cell cycle related proteins. Yao Xue Xue Bao 2009; 44: 973-9.
64. 2/M phase and cell death in HepG2 cells via alteration of reactive oxygen species. Eur. J. Pharmacol. 2007; 568: 31-44.
65. Stanslas J, Liew PS, Iftikhar N et al. Potential of AG in the treatment of breast cancer. Eur. J. Cancer 2001; 37(Suppl.): S169. (Abstract).
66. Astha V, Harish P, Neeta S. Andrographolide: A new plant-derived antineoplastic entity on horizon. Evid. Based Complement. Alternat. Med. 2009; 2011: 1-9.
67. Hung SK, Hung LC, Kuo CD et al. Andrographolide sensitizes Ras-transformed cells to radiation in vitro and in vivo. Int. J. Radiat. Oncol. Biol. Phys. 2010; 77: 1232-9.
68. Sheeja K, Kuttan G. Activation of cytotoxic T lymphocyte responses and attenuation of tumor growth in vivo by Andrographis paniculata extract and andrographolide. Immunopharmacol. Immunotoxicol. 2007; 29: 81-93.
69. Satyanarayana C, Deevi D, Rajagopalan R, Srinivas N, Rajagopal S. DRF3188 a novel semi-synthetic analog of andrographolide: Cellular response to MCF 7 breast cancer cells. BMC Cancer 2004; 4: 26.
70. Zhou J, Zhang S, Ong CN, Shen HM. Critical role of pro-apoptotic Bcl-2 family members in andrographolide-induced apoptosis in human cancer cells. Biochem. Pharmacol. 2006; 72: 132-44.
71. Li J, Huang W, Zhang H, Wang X, Zhou H. Synthesis of andrographolide derivatives and their TNF-α and IL-6 expression inhibitory activities. Bioorg. Med. Chem. Lett. 2007; 17: 6891-4.
72. Kuwana T, Bouchier-Hayes L, Chipuk JEet al.BH3 domains of BH3-only proteins differentially regulate Bax-mediated mitochondrial membrane permeabilization both directly and indirectly. Mol. Cell 2005; 17: 525-35.
73. Zhou J, Lu GD, Ong CS, Ong CN, Shen HM. Andrographolide sensitizes cancer cells to TRAIL-induced apoptosis via p53-mediated death receptor 4 up-regulation. Mol. Cancer Ther. 2008; 7: 2170-80.
74. Ji L, Liu T, Liu J, Chen Y, Wang Z. Andrographolide inhibits human hepatoma-derived Hep3B cell growth through the activation of c-Jun N-terminal kinase. Planta Med. 2007; 73: 1397-401.
75. Ji L, Shen K, Jiang P, Morahan G, Wang Z. Critical roles of cellular glutathione homeostasis and JNK activation in andrographolide-mediated apoptotic cell death in human hepatoma cells. Mol. Carcinog. 2011; 50: 580-91.
76. Zhou J, Ong CN, Hur GM, Shen HM. Inhibition of the JAK-STAT3 pathway by andrographolide enhances chemosensitivity of cancer cells to doxorubicin. Biochem. Pharmacol. 2010; 79: 1242-50.
77. Chun JY, Tummala R, Nadiminty N et al. Andrographolide, an herbal medicine, inhibits interleukin-6 expression and suppresses prostate cancer cell growth. Genes Cancer 2010; 1: 868-76.
78. Liu C, Nadiminty N, Tummala R et al. Andrographolide targets androgen receptor pathway in castration-resistant prostate cancer. Genes Cancer 2011; 2: 151-9.
79. Rao JS. Molecular mechanisms of glioma invasiveness. The role of proteases. Nat. Rev. Cancer 2004; 3: 489-501.
80. Lee YC, Lin HH, Hsu CH, Wang CJ, Chiang TA, Chen JH. Inhibitory effects of andrographolide on migration and invasion in human non-small cell lung cancer A549 cells via down-regulation of PI3K/Akt signaling pathway. Eur. J. Pharmacol. 2010; 632: 23-32.
81. Chao HP, Kuo CD, Chiu JH, Fu SL. Andrographolide exhibits anti-invasive activity against colon cancer cells via inhibition of MMP2 activity. Planta Med. 2010; 76: 1827-34.
82. Pratheeshkumar P, Kuttan G. Andrographolide inhibits human umbilical vein endothelial cell invasion and migration by regulating MMP-2 and MMP-9 during angiogenesis. J. Environ. Pathol. Toxicol. Oncol. 2011; 30: 33-41.
83. Sauer H, Wartenberg M, Hescheler J. Reactive oxygen species as intracellular messengers during cell growth and differentiation. Cell. Physiol. Biochem. 2001; 11: 173-86.
84. Baud V, Karin M. Is NF-κB a good target for cancer therapy? Hopes and pitfallsNat. Rev. Drug Discov. 2009; 8: 33-40.
85. Liang FP, Lin CH, Kuo CD, Chao HP, Fu SL. Suppression of v-Src transformation by andrographolide via degradation of the v-Src protein and attenuation of the Erk signaling pathway. J. Biol. Chem. 2008; 283: 5023-33.
86. Lin HH, Tsai CW, Chou FP et al. Andrographolide down-regulates hypoxia-inducible factor-1alpha in human non-small cell lung cancer A549 cells. Toxicol. Appl. Pharmacol. 2011; 250: 336-45.
87. Lepelletier Y, Camara-Clayette V, Jin H et al. Prevention of mantle lymphoma tumor establishment by routing transferrin receptor toward lysosomal compartments. Cancer Res. 2007; 67: 1145-54.
88. Capdevila J, Elez E, Macarulla T, Ramos FJ, Ruiz-Echarri M, Tabernero J. Anti-epidermal growth factor receptor monoclonal antibodies in cancer treatment. Cancer Treat. Rev. 2009; 35: 354-63.
89. Tan Y, Chiow KH, Huang D, Wong SH. Andrographolide regulates epidermal growth factor receptor and transferrin receptor trafficking in epidermoid carcinoma (A-431) cells. Br. J. Pharmacol. 2010; 159: 1497-510.
90. Burgos R, Hancke J, Bertoglio J et al. Efficacy of an Andrographis paniculata composition for the relief of rheumatoid arthritis symptoms: A prospective randomized placebo-controlled trial. Clin. Rheumatol. 2009; 28: 931-46.
91. Coon JT, Ernst E. Andrographis paniculata in the treatment of upper respiratory tract infections: A systematic review of safety and efficacy. Planta Med. 2004; 70: 293-8.
92. Poolsup N, Suthisisang C, Prathanturarug S, Asawamekin A, Chanchareon U. Andrographis paniculata in the symptomatic treatment of uncomplicated upper respiratory tract infection: Systematic review of randomized controlled trials. J. Clin. Pharm. Ther. 2004; 29: 37-45.
93. Thamlikitkul V, Dechatiwongse T, Theerapong S et al. Efficacy of Andrographis paniculata, Nees for pharyngotonsillitis in adults. J. Med. Assoc. Thai. 1991; 74: 437-42.
94. Chang J, Zhang RM, Zhang Y et al. Andrographolide drop-pill in treatment of acute upper respiratory tract infection with external wind-heat syndrome: A multicenter and randomized controlled trial. J. Chin. Integr. Med. 2008; 6: 1239-45. (in Chinese).