Perspectives on medicinal properties of plumbagin and its analogs

Medicinal Research Reviews

Volumn 32, Issue 6, 2012, Pages 1131-1158

  Padhye, Subhash ^a,b   Dandawate, Prasad ^c   Yusufi, Mujahid ^c   Ahmad, Aamir ^a   Sarkar, Fazlul H ^a  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b DR DY PATIL UNIVERSITY   (India)

^c MCE Society's Abeda Inamdar Senior   (India)

Author keywords

Anticancer; Drug resistance; NF B; Plumbagin; Reactive oxygen species

Indexed keywords

ESTROGEN RECEPTOR ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; METAL COMPLEX; PLANT EXTRACT; PLUMBAGIN; PLUMBAGIN DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ACINETOBACTER BAUMANNII; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CANDIDA ALBICANS; CANDIDA KRUSEI; CANDIDA TROPICALIS; CELL CYCLE ARREST; CLADOSPORIUM; CRYPTOCOCCUS NEOFORMANS; DROSERA; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; FUSARIUM; GALACTOMYCES GEOTRICHUM; HUMAN; KIDNEY CANCER; LEUKEMIA; LIVER CANCER; LUNG CANCER; LUNG NON SMALL CELL CANCER; MAXIMUM PLASMA CONCENTRATION; MEDICINAL PLANT; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; MYELOMA; NONHUMAN; OVARY CANCER; PANCREAS CANCER; PENICILLIUM; PHYSICAL CHEMISTRY; PLUMBAGINACEAE; PROSTATE CANCER; SKIN CARCINOMA; SPODOPTERA LITURA; UTERINE CERVIX CANCER;

ANIMALS; BIOLOGICAL AVAILABILITY; ELECTROCHEMICAL TECHNIQUES; HUMANS; METALS; NAPHTHOQUINONES; PLANTS, MEDICINAL; SPECTRUM ANALYSIS;

EID: 84867407020     PISSN: 01986325     EISSN: 10981128     Source Type: Journal    
DOI: 10.1002/med.20235     Document Type: Article

References (132)

1. Bertin C, Yang X, Weston LA. The role of root exudates and allelochemicals in the rhizosphere. Plant Soil. 2003;256:67-83.
2. Gu XD, Sun MY, Zhang L, Fu HW, Cui L, Chen RZ, Zhang DW, Tian JK. UV-B induced changes in the secondary metabolites of Morus alba L. Leaves Molecules. 2010;15:2980-2993.
3. Babula P, Mikelova R, Adam V, Kizek R, Havel L, Sladky Z. Naphthoquinones-Biosynthesis, occurrence and metabolism in plants. Ceska Slov Farm. 2006;55:151-159.
4. Babula P, Adam V, Havel L, Kizek R. Naphthoquinones and their pharmacological properties. Ceska Slov Farm. 2007;56:114-120.
5. Krolicka A, Szpitter A, Maciag M, Biskup E, Gilgenast E, Romanik G, Kaminski M, Wegrzyn G, Lojkowska E. Antibacterial and antioxidant activity of the secondary metabolites from in vitro cultures of Drosera aliciae. Biotechnol Appl Biochem. 2009;53:175-184.
6. Weissenberg M, Meisner J, Klein M, Schaeffler I, Eliyahu M, Schmutterer H, Ascher KRS. Effect of substituent and ring changes in naturally occurring naphthoquinones on the feeding response of larvae of the Mexican bean beetle, Epilachna varivestis. J Chem Ecol. 1997;23:3-18.
7. Duroux L, Delmotte FM, Lancelin JM, Keravis G, Jay-Allemand C. Insight into naphthoquinone metabolism: Beta-glucosidase-catalysed hydrolysis of hydrojuglone beta-D-glucopyranoside. Biochem J. 1998;333:275-283.
8. Talcott RE, Smith MT, Giannini DD. Inhibition of microsomal lipid peroxidation by naphthoquinones: Structure-activity relationships and possible mechanisms of action. Arch Biochem Biophys. 1985;241:88-94.
9. Reese S, Vidyasagar A, Jacobson L, Acun Z, Esnault S, Hullett D, Malter JS, Djamali A. The Pin 1 inhibitor juglone attenuates kidney fibrogenesis via Pin 1-independent mechanisms in the unilateral ureteral occlusion model. Fibrog Tissue Rep. 2010;3:1-
10. Marchionatti AM, Picotto G, Narvaez CJ, Welsh J, Tolosa de Talamoni NG. Antiproliferative action of menadione and 1, 25(OH)2D3 on breast cancer cells. J Steroid Biochem Mol Biol. 2009;113:227-232.
11. Sharma S, Sharma BK, Prabhakar YS. Juglone derivatives as antitubercular agents: A rationale for the activity profile. Eur J Med Chem. 2009;44:2847-2853.
12. Nadkarni KM. Indian materia medica. Bombay, India: Popular Book Depot; 1954.
13. Chopra RN, Nayar SL, Chopra IC. Glossary of Indian medicinal plants. New Delhi, India: CSIR; 1956.
14. Dutt UC. The materia medica of the Hindus. Calcutta, India: Thacker, Spink & Co; 1877.
15. Hisar RS, Wolff RE. Sur l'identification de cristaux vesicants extraits des racines de Babink. Bull Soc Chim France. 1954;33:507-
16. Yoganarasimhan SN. Medicinal plants of India. Bangalore, India: Regional Research Institute; 2000. pp 425-426.
17. Kirtikar KR, Basu BD. Indian medicinal plant. Dehradun: International book distributors; 1975. pp 1465-1470.
18. Lawrence GHM. Taxonomy of vascular plants. New York: The Macmillan Company; 1965. pp 660-662.
19. Veluri R, Diwan PV. Phytochemical and pharmacological aspects of Plumbago zeylanica. Indian Drug. 1999;36:724-730.
20. de P, Figueiredo MR, Aragao TV, Kaplan MA. Antimicrobial activity in vitro of plumbagin isolated from Plumbago species. Mem Inst Oswaldo Cruz. 2003;98:959-961.
21. Madhavan V, Basnett H, Kumar A, Yoganarasimhan S. Fingerprinting of plumbagin in Drosera burmannii vahl using high performance thin layer chromatography. Indian J Pharm Sci. 2008;70:798-800.
22. Aryanathan S. Chemical examination of three Plumbago species. Thanjavur, India: Ph.D. Thesis, Sastra University; 2009.
23. Mallavadhani UV, Sahu G, Muralidhar J. Screening of Plumbago species for the bio-active marker plumbagin. Pharm Biol. 2002;40:508-511.
24. Padhye SB, Kulkarni BA. Studies on the root constituents of Plumbago zeylanica. J Univ Poona Sci Technol. 1973;44:27-29.
25. Budzianowski J. Naphthoquinone glucosides of Drosera gigantea from in vitro cultures. Planta Med. 2000;66:667-669.
26. Wang Q, Shu J, Zeng L. Chemical constituents of Drosera peltata Smith var. lunata (Buch.-Ham.) C.B. clarke collected in Tibet. Zhongguo Zhong Yao Za Zhi. 1998;23:683-704.
27. Aung HH, Chia LS, Goh NK, Chia TF, Ahmed AA, Pare PW, Mabry TJ. Phenolic constituents from the leaves of the carnivorous plant Nepenthes gracilis. Fitoterapia. 2002;73:445-447.
28. Marczak L, Kawiak A, Lojkowska E, Stobiecki M. Secondary metabolites in in vitro cultured plants of the genus Drosera. Phytochem Anal. 2005;16:143-149.
29. Kamal GM, Gunaherath B, Gunatilaka AAL, Thomson RH. Structure of plumbazeylanone: A novel trimer of plumbagin from Plumbago zeylanica. Tetrahedron Lett. 1984;25:4801-4804.
30. Babula P, Adam V, Kizek R, Sladk Z, Havel L. Naphthoquinones as allelochemical triggers of programmed cell death. Environ Exp Bot. 2009;65:330-337.
31. Komaraiah P, Ramakrishna SV, Reddanna P, Kavi Kishor PB. Enhanced production of plumbagin in immobilized cells of Plumbago rosea by elicitation and in situ adsorption. J Biotechnol. 2003;101:181-187.
32. Satheeshkumar K, Seeni S. In vitro mass multiplication and production of roots in Plumbago rosea. Planta Med. 2003;69:83-86.
33. de P, Figueiredo MR, Kaplan MA. Isolation of secondary metabolites from roots of Plumbago auriculata Lam. by countercurrent chromatography. Phytochem Anal. 2005;16:278-281.
34. Rodrigues SV, Viana LM, Baumann W. UV/Vis spectra and solubility of some naphthoquinones, and the extraction behavior of plumbagin from Plumbago scandens roots in supercritical CO2. Anal Bioanal Chem. 2006;385:895-900.
35. Babula P, Mikelova R, Adam V, Kizek R, Havel L, Sladky Z. Using of liquid chromatography coupled with diode array detector for determination of naphthoquinones in plants and for investigation of influence of pH of cultivation medium on content of plumbagin in Dionaea muscipula. J Chromatogr B Analyt Technol Biomed Life Sci. 2006;842:28-35.
36. Hsieh YJ, Lin LC, Tsai TH. Measurement and pharmacokinetic study of plumbagin in a conscious freely moving rat using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006;844:1-5.
37. Mandala Rayabandla SK, Aithal K, Anandam A, Shavi G, Nayanabhirama U, Arumugam K, Musmade P, Bhat K, Bola S. Preparation, in vitro characterization, pharmacokinetic, and pharmacodynamic evaluation of chitosan-based plumbagin microspheres in mice bearing B16F1 melanoma. Drug Deliv. 2010;17:103-113.
38. Chandrasekaran B, Nagarajan B. Metabolism of echitamine and plumbagin in rats. J Biosci. 1981;3:395-400.
39. Padhye SB, Kulkarni BA. Near-infrared evidence for H-bonding in phthiocol and plumbagin. J Univ Poona Sci Technol. 1974;46:93-95.
40. Padhye SB, Kulkarni BA. Evidence for the hydrogen bonding in some hydroxylated naphthaquinones by adsorption chromatography. Chromatographia. 1975;8:352-353.
41. Padhye SB, Kulkarni BA. Hydrogen bonding interaction of some naturally occurring isomeric juglones with dioxane. J Phys Chem. 1975;79:927-928.
42. Ahmed IM, Hudson A, Alberti A. ESR studies of free radicals derived from hydroxyquinones: I. Group 14 adducts of hydroxynaphthoquinones. J Organomet Chem. 1987;333:9-16.
43. Sajan D, Laladhas KP, Hubert J, Jayakumar VS. Vibrational spectra and density functional theoretical calculations on the antitumor drug, plumbagin. J Raman Spectrosc. 2005;36:1001-1011.
44. Hernandez-Munoz LS, Gomez M, Gonzalez FJ, Gonzalez I, Frontana C. Towards a molecular-level understanding of the reactivity differences for radical anions of juglone and plumbagin: An electrochemical and spectroelectrochemical approach. Org Biomol Chem. 2009;7:1896-1903.
45. Raouf J, Golabi SM. Electrochemical behaviour of plumbagin at solid electrodes in non-aqueous media. Bull Electrochem. 1997;13:311-316.
46. Sreelatha T, Hymavathi A, Babu KS, Murthy JM, Pathipati UR, Rao JM. Synthesis and insect antifeedant activity of plumbagin derivatives with the amino acid moiety. J Agric Food Chem. 2009;57:6090-6094.
47. Hazra B, Sarkar R, Bhattacharyya S, Ghosh PK, Chel G, Dinda B. Synthesis of plumbagin derivatives and their inhibitory activities against Ehrlich ascites carcinoma in vivo and Leishmania donovani Promastigotes in vitro. Phytother Res. 2002;16:133-137.
48. Salmon-Chemin L, Lemaire A, De FS, Deprez B, Sergheraert C, Vioud-Charvet E. Parallel synthesis of a library of 1, 4-naphthoquinones and automated screening of potential inhibitors of trypanothione reductase from Trypanosoma cruzi. Bioorg Med Chem Lett. 2000;10:631-635.
49. Salmon-Chemin L, Buisine E, Yardley V, Kohler S, Debreu MA, Landry V, Sergheraert C, Croft SL, Krauth-Siegel RL, vioud-Charvet E. 2- and 3-substituted 1, 4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: Synthesis and correlation between redox cycling activities and in vitro cytotoxicity. J Med Chem. 2001;44:548-565.
50. Wurm G, Baumann J, Geres U, Schmidt H. Lipophilic naphthols and 1, 4-naphthoquinones as inhibitors of prostaglandin synthesis. 6. Study of 1, 4-naphthoquinones. Arzneimittelforschung. 1984;34:652-658.
51. Ogihara K, Yamashiro R, Higa M, Yogi S. Preparation of naphthoquinone derivatives from plumbagin and their ichthyotoxicity. Chem Pharm Bull. 1997;45:437-445.
52. Gammon DW, Steenkamp DJ, Mavumengwana V, Marakalala MJ, Mudzunga TT, Hunter R, Munyololo M. Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol. Bioorg Med Chem. 2010;18:2501-2514.
53. Adikaram NKB, Karunaratne V, Bandara BMR, Hewage CM, Abayasekara C, Mendis BSS. Antifungal properties of plumbagin. J Natl Sci Foundation Sri Lanka. 2002;30:89-95.
54. Joshi CR, Jagtap GS, Chalgeri SV. Antimicrobial properties of metal chelates of plumbagin. Ind J Pharm Sci. 1988;50:107-108.
55. Rane SY. Studies in metal chelates of methylated isomeric juglones. Pune, India: Ph.D. Thesis, University of Pune, 1978.
56. Padhye SB, Joshi CR, Kulkarni BA. Studies of some rare earth chelates of naphthoquinone antibacterials. J Inorg Nucl Chem. 1977;39:1289-1292.
57. Dangalla ACM, Ileperuma OA. Preparation and properties of some metal complexes of plumbagin. J Nat Sci Coan Sri Lanka. 1985;13:141-146.
58. Chen ZF, Tan MX, Liu LM, Liu YC, Wang HS, Yang B, Peng Y, Liu HG, Liang H, Orvig C. Cytotoxicity of the traditional chinese medicine (TCM) plumbagin in its copper chemistry. Dalton Trans. 2009;10824-10833.
59. Kunte DP, Kumbhar AS, Padhye SB, Chopade BA. Curing of R-plasmids in Escherichia coli by plant antibiotic juglone and its metal complexes. In: Einhorn J, Nord C, Norrby SR, editors. Recent advances in chemotherapy. Washington, DC: American Society for Microbiology; 1994. pp 502-503.
60. Klaus V, Hartmann T, Gambini J, Graf P, Stahl W, Hartwig A, Klotz LO. 1, 4-Naphthoquinones as inducers of oxidative damage and stress signaling in HaCaT human keratinocytes. Arch Biochem Biophys. 2010;496:93-100.
61. Tilak JC, Adhikari S, Devasagayam TP. Antioxidant properties of Plumbago zeylanica, an Indian medicinal plant and its active ingredient, plumbagin. Redox Rep. 2004;9:219-227.
62. Demma J, Hallberg K, Hellman B. Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells. Toxicol In Vitro. 2009;23:266-271.
63. Sankar R, Devamanoharan P, Raghupathi G, Krishnasamy M, Devi C. Lipid peroxidation in plumbagin administered rats. J Biosci. 1987;12:267-271.
64. Ahmad A, Farhan AS, Singh S, Hadi SM. DNA breakage by resveratrol and Cu(II): Reaction mechanism and bacteriophage inactivation. Cancer Lett. 2000;154:29-37.
65. Hadi SM, Asad SF, Singh S, Ahmad A. Putative mechanism for anticancer and apoptosis-inducing properties of plant-derived polyphenolic compounds. IUBMB Life. 2000;50:167-171.
66. Khan NS, Ahmad A, Hadi SM. Anti-oxidant, pro-oxidant properties of tannic acid and its binding to DNA. Chem Biol Interact. 2000;125:177-189.
67. Singh S, Asad SF, Ahmad A, Khan NU, Hadi SM. Oxidative DNA damage by capsaicin and dihydrocapsaicin in the presence of Cu(II). Cancer Lett. 2001;169:139-146.
68. Ahmad A, Syed FA, Singh S, Hadi SM. Prooxidant activity of resveratrol in the presence of copper ions: Mutagenicity in plasmid DNA. Toxicol Lett. 2005;159:1-12.
69. Checker R, Sharma D, Sandur SK, Khanam S, Poduval TB. Anti-inflammatory effects of plumbagin are mediated by inhibition of NF-kappaB activation in lymphocytes. Int Immunopharmacol. 2009;9:949-958.
70. Ahmad A, Banerjee S, Wang Z, Kong D, Sarkar FH. Plumbagin-induced apoptosis of human breast cancer cells is mediated by inactivation of NF-kappaB and Bcl-2. J Cell Biochem. 2008;105:1461-1471.
71. Jackson JK, Higo T, Hunter WL, Burt HM. Topoisomerase inhibitors as anti-arthritic agents. Inflamm Res. 2008;57:126-134.
72. Kuo PL, Hsu YL, Cho CY. Plumbagin induces G2-M arrest and autophagy by inhibiting the AKT/mammalian target of rapamycin pathway in breast cancer cells. Mol Cancer Ther. 2006;5:3209-3221.
73. Aziz MH, Dreckschmidt NE, Verma AK. Plumbagin, a medicinal plant-derived naphthoquinone, is a novel inhibitor of the growth and invasion of hormone-refractory prostate cancer. Cancer Res. 2008;68:9024-9032.
74. Powolny AA, Singh SV. Plumbagin-induced apoptosis in human prostate cancer cells is associated with modulation of cellular redox status and generation of reactive oxygen species. Pharm Res. 2008;25:2171-2180.
75. Thasni KA, Rakesh S, Rojini G, Ratheeshkumar T, Srinivas G, Priya S. Estrogen-dependent cell signaling and apoptosis in BRCA1-blocked BG1 ovarian cancer cells in response to plumbagin and other chemotherapeutic agents. Ann Oncol. 2008;19:696-705.
76. Srinivas G, Annab LA, Gopinath G, Banerji A, Srinivas P. Antisense blocking of BRCA1 enhances sensitivity to plumbagin but not tamoxifen in BG-1 ovarian cancer cells. Mol Carcinog. 2004;39:15-25.
77. Chen CA, Chang HH, Kao CY, Tsai TH, Chen YJ. Plumbagin, isolated from Plumbago zeylanica, induces cell death through apoptosis in human pancreatic cancer cells. Pancreatology. 2009;9:797-809.
78. Sandur SK, Pandey MK, Sung B, Aggarwal BB. 5-Hydroxy-2-methyl-1, 4-naphthoquinone, a vitamin K3 analogue, suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase, SHP-1: Potential role in chemosensitization. Mol Cancer Res. 2010;8:107-118.
79. Bringmann G, Rudenauer S, Irmer A, Bruhn T, Brun R, Heimberger T, Stuhmer T, Bargou R, Chatterjee M. Antitumoral and antileishmanial dioncoquinones and ancistroquinones from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and Ancistrocladus abbreviatus (Ancistrocladaceae). Phytochemistry. 2008;69:2501-2509.
80. Gomathinayagam R, Sowmyalakshmi S, Mardhatillah F, Kumar R, Akbarsha MA, Damodaran C. Anticancer mechanism of plumbagin, a natural compound, on non-small cell lung cancer cells. Anticancer Res. 2008;28:785-792.
81. Hsu YL, Cho CY, Kuo PL, Huang YT, Lin CC. Plumbagin (5-hydroxy-2-methyl-1, 4-naphthoquinone) induces apoptosis and cell cycle arrest in A549 cells through p53 accumulation via c-Jun NH2-terminal kinase-mediated phosphorylation at serine 15 in vitro and in vivo. J Pharmacol Exp Ther. 2006;318:484-494.
82. Acharya BR, Bhattacharyya B, Chakrabarti G. The natural naphthoquinone plumbagin exhibits antiproliferative activity and disrupts the microtubule network through tubulin binding. Biochemistry. 2008;47:7838-7845.
83. Shieh JM, Chiang TA, Chang WT, Chao CH, Lee YC, Huang GY, Shih YX, Shih YW. Plumbagin inhibits TPA-induced MMP-2 and u-PA expressions by reducing binding activities of NF-kappaB and AP-1 via ERK signaling pathway in A549 human lung cancer cells. Mol Cell Biochem. 2010;335:181-193.
84. Wang CC, Chiang YM, Sung SC, Hsu YL, Chang JK, Kuo PL. Plumbagin induces cell cycle arrest and apoptosis through reactive oxygen species/c-Jun N-terminal kinase pathways in human melanoma A375.S2 cells. Cancer Lett. 2008;259:82-98.
85. Nazeem S, Azmi AS, Hanif S, Ahmad A, Mohammad RM, Hadi SM, Kumar KS. Plumbagin induces cell death through a copper-redox cycle mechanism in human cancer cells. Mutagenesis. 2009;24:413-418.
86. Prasad VS, Devi PU, Rao BS, Kamath R. Radiosensitizing effect of plumbagin on mouse melanoma cells grown in vitro. Indian J Exp Biol. 1996;34:857-858.
87. Kawiak A, Piosik J, Stasilojc G, Gwizdek-Wisniewska A, Marczak L, Stobiecki M, Bigda J, Lojkowska E. Induction of apoptosis by plumbagin through reactive oxygen species-mediated inhibition of topoisomerase II. Toxicol Appl Pharmacol. 2007;223:267-276.
88. Fujii N, Yamashita Y, Arima Y, Nagashima M, Nakano H. Induction of topoisomerase II-mediated DNA cleavage by the plant naphthoquinones plumbagin and shikonin. Antimicrob Agents Chemother. 1992;36:2589-2594.
89. Xu KH, Lu DP. Plumbagin induces ROS-mediated apoptosis in human promyelocytic leukemia cells in vivo. Leuk Res. 2010;34:658-665.
90. Zhao YL, Lu DP. Effects of plumbagin on the human acute promyelocytic leukemia cells in vitro. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2006;14:208-211.
91. Jaiswal AS, Bloom LB, Narayan S. Long-patch base excision repair of apurinic/apyrimidinic site DNA is decreased in mouse embryonic fibroblast cell lines treated with plumbagin: Involvement of cyclin-dependent kinase inhibitor p21Waf-1/Cip-1. Oncogene. 2002;21:5912-5922.
92. Shih YW, Lee YC, Wu PF, Lee YB, Chiang TA. Plumbagin inhibits invasion and migration of liver cancer HepG2 cells by decreasing productions of matrix metalloproteinase-2 and urokinase- plasminogen activator. Hepatol Res. 2009;39:998-1009.
93. Ravindra KC, Selvi BR, Arif M, Reddy BA, Thanuja GR, Agrawal S, Pradhan SK, Nagashayana N, Dasgupta D, Kundu TK. Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin. J Biol Chem. 2009;284:24453-24464.
94. Parimala R, Sachdanandam P. Effect of plumbagin on some glucose metabolising enzymes studied in rats in experimental hepatoma. Mol Cell Biochem. 1993;125:59-63.
95. Kuo YH, Chang CI, Li SY, Chou CJ, Chen CF, Kuo YH, Lee KH. Cytotoxic constituents from the stems of Diospyros maritima. Planta Med. 1997;63:363-365.
96. Ding Y, Chen ZJ, Liu S, Che D, Vetter M, Chang CH. Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone. J Pharm Pharmacol. 2005;57:111-116.
97. Srinivas P, Gopinath G, Banerji A, Dinakar A, Srinivas G. Plumbagin induces reactive oxygen species, which mediate apoptosis in human cervical cancer cells. Mol Carcinog. 2004;40:201-211.
98. Montoya J, Varela-Ramirez A, Estrada A, Martinez LE, Garza K, Aguilera RJ. A fluorescence-based rapid screening assay for cytotoxic compounds. Biochem Biophys Res Commun. 2004;325:1517-1523.
99. Nair S, Nair RR, Srinivas P, Srinivas G, Pillai MR. Radiosensitizing effects of plumbagin in cervical cancer cells is through modulation of apoptotic pathway. Mol Carcinog. 2008;47:22-33.
100. Sandur SK, Ichikawa H, Sethi G, Ahn KS, Aggarwal BB. Plumbagin (5-hydroxy-2-methyl-1, 4-naphthoquinone) suppresses NF-kappaB activation and NF-kappaB-regulated gene products through modulation of p65 and IkappaBalpha kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents. J Biol Chem. 2006;281:17023-17033.
101. Buchholz TA, Garg AK, Chakravarti N, Aggarwal BB, Esteva FJ, Kuerer HM, Singletary SE, Hortobagyi GN, Pusztai L, Cristofanilli M, Sahin AA. The nuclear transcription factor kappaB/bcl-2 pathway correlates with pathologic complete response to doxorubicin-based neoadjuvant chemotherapy in human breast cancer. Clin Cancer Res. 2005;11:8398-8402.
102. Ganasoundari A, Zare SM, Devi PU. Modification of bone marrow radiosensensitivity by medicinal plant extracts. Br J Radiol. 1997;70:599-602.
103. Devi PU, Rao BS, Solomon FE. Effect of plumbagin on the radiation induced cytogenetic and cell cycle changes in mouse Ehrlich ascites carcinoma in vivo. Indian J Exp Biol. 1998;36:891-895.
104. Wang JY, Burger RM, Drlica K. Role of superoxide in catalase-peroxidase-mediated isoniazid action against mycobacteria. Antimicrob Agents Chemother. 1998;42:709-711.
105. Mossa JS, El-Feraly FS, Muhammad I. Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide. Phytother Res. 2004;18:934-937.
106. Bulatovic VM, Wengenack NL, Uhl JR, Hall L, Roberts GD, Cockerill FR, Rusnak F. Oxidative stress increases susceptibility of Mycobacterium tuberculosis to isoniazid. Antimicrob Agents Chemother. 2002;46:2765-2771.
107. Borges-Argaez R, Canche-Chay CI, Pena-Rodriguez LM, Said-Fernandez S, Molina-Salinas GM. Antimicrobial activity of Diospyros anisandra. Fitoterapia. 2007;78:370-372.
108. Kuete V, Tangmouo JG, Meyer JJ, Lall N. Diospyrone, crassiflorone and plumbagin: Three antimycobacterial and antigonorrhoeal naphthoquinones from two Diospyros spp. Int J Antimicrob Agents. 2009;34:322-325.
109. Garbe TR. Co-induction of methyltransferase Rv0560c by naphthoquinones and fibric acids suggests attenuation of isoprenoid quinone action in Mycobacterium tuberculosis. Can J Microbiol. 2004;50:771-778.
110. Didry N, Dubreuil L, Pinkas M. Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Pharmazie. 1994;49:681-683.
111. Abdul KM, Ramchender RP. Modulatory effect of plumbagin (5-hydroxy-2-methyl-1, 4-naphthoquinone) on macrophage functions in BALB/c mice. I. Potentiation of macrophage bactericidal activity. Immunopharmacology. 1995;30:231-236.
112. Park BS, Lee HK, Lee SE, Piao XL, Takeoka GR, Wong RY, Ahn YJ, Kim JH. Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori. J Ethnopharmacol. 2006;105:255-262.
113. Gu JQ, Graf TN, Lee D, Chai HB, Mi Q, Kardono LB, Setyowati FM, Ismail R, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kroll DJ, Falkinham JO, Wall ME, Wani MC, Kinghorn AD, Oberlies NH. Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. J Nat Prod. 2004;67:1156-1161.
114. Chen JW, Sun CM, Sheng WL, Wang YC, Syu WJ. Expression analysis of up-regulated genes responding to plumbagin in Escherichia coli. J Bacteriol. 2006;188:456-463.
115. Lakhmi VV, Padma S, Polasa H. Elimination of multidrug-resistant plasmid in bacteria by plumbagin, a compound derived from a plant. Curr Microbiol. 1987;16:159-161.
116. Patil A, Mukherjee A, Balu C, Kumbhar A, Padhye SB. DNA strand scission and plasmid curing activity of an Indian folk medicine constituent-Chitrak. In: Einhorn J, Nord C, Norrby SR, editors. Recent advances in chemotherapy. Washington, DC: American Society forMicrobiology; 1994. pp 504.
117. Padhye SB, Kumbhar AS, Chopade BA. Reversal of drug resistance by plumbagin (5-hydroxy-2 methyl, 1-4 naphthoquinone) in microorganisms. Indo-French Symposium on Apoptosis and Multiple Drug Resistance, Goa, India; 1997. pp 45-46.
118. Kunte DP, Dhakephalkar PK, Mukerjee A, Patil A, Kumbhar A, Padhye SB, Chopade BA. Elimination of plasmid mediated antibiotic and metal resistance in Acinetobacter baumannii C11 by naturally occurring quinones and their metal complexes. J Inorg Biochem. 1993;51:387-
119. Durga R, Sridhar P, Polasa H. Effects of plumbagin on antibiotic resistance in bacteria. Indian J Med Res. 1990;91:18-20.
120. Shukla S, Wu CP, Nandigama K, Ambudkar SV. The naphthoquinones, vitamin K3 and its structural analogue plumbagin, are substrates of the multidrug resistance linked ATP binding cassette drug transporter ABCG2. Mol Cancer Ther. 2007;6:3279-3286.
121. Farr SB, Natvig DO, Kogoma T. Toxicity and mutagenicity of plumbagin and the induction of a possible new DNA repair pathway in Escherichia coli. J Bacteriol. 1985;164:1309-1316.
122. Dzoyem JP, Tangmouo JG, Lontsi D, Etoa FX, Lohoue PJ. In vitro antifungal activity of extract and plumbagin from the stem bark of Diospyros crassiflora Hiern (Ebenaceae). Phytother Res. 2007;21:671-674.
123. Mahoney N, Molyneux RJ, Campbell BC. Regulation of aflatoxin production by naphthoquinones of walnut (Juglans regia). J Agric Food Chem. 2000;48:4418-4421.
124. Curreli N, Sollai F, Massa L, Comandini O, Rufo A, Sanjust E, Rinaldi A, Rinaldi AC. Effects of plant-derived naphthoquinones on the growth of Pleurotus sajor-caju and degradation of the compounds by fungal cultures. J Basic Microbiol. 2001;41:253-259.
125. Singh UV, Udupa N. Reduced toxicity and enhanced antitumor efficacy of betacyclodextrin plumbagin inclusion complex in mice bearing Ehrlich ascites carcinoma. Indian J Physiol Pharmacol. 1997;41:171-175.
126. Santhakumari G, Saralamma PG, Radhakrishnan N. Effect of plumbagin on cell growth & mitosis. Indian J Exp Biol. 1980;18:215-218.
127. Edenharder R, Tang X. Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by flavonoids, coumarins, quinones and other phenolic compounds. Food Chem Toxicol. 1997;35:357-372.
128. Singh UV, Bisht KS, Rao S, Uma Devi P, Udupa N. Reduced toxicity and enhanced antitumor efficacy of plumbagin using poly (Lactic-co-glycolic) biodegradable injectable implant. Indian J Pharmacol. 1997;29:168-172.
129. Kini DP, Pandey S, Shenoy BD, Singh UV, Udupa N, Umadevi P, Kamath R, Nagarajkumari, Ramanarayan K. Antitumor and antifertility activities of plumbagin controlled release formulations. Indian J Exp Biol. 1997;35:374-379.
130. Naresh RA, Udupa N, Devi PU. Niosomal plumbagin with reduced toxicity and improved anticancer activity in BALB/C mice. J Pharm Pharmacol. 1996;48:1128-1132.
131. Tiwari SB, Pai RM, Udupa N. Temperature sensitive liposomes of plumbagin: Characterization and in vivo evaluation in mice bearing melanoma B16F1. J Drug Target. 2002;10:585-591.
132. Inbaraj JJ, Chignell CF. Cytotoxic action of juglone and plumbagin: A mechanistic study using HaCaT keratinocytes. Chem Res Toxicol. 2004;17:55-62.