Subditine, a new monoterpenoid indole alkaloid from bark of Nauclea subdita (Korth.) Steud. Induces apoptosis in human prostate cancer cells

PLoS ONE

Volumn 9, Issue 2, 2014, Pages

  Liew, Sook Yee ^a   Looi, Chung Yeng ^a   Paydar, Mohammadjavad ^a   Cheah, Foo Kit ^a   Leong, Kok Hoong ^a   Wong, Won Fen ^a   Mustafa, Mohd Rais ^a   Litaudon, Marc ^b   Awang, Khalijah ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ANGUSTIDINE; ANGUSTINE; ANGUSTOLINE; CASPASE 3; CASPASE 7; CASPASE 9; CYTOCHROME C; GLUTATHIONE REDUCTASE; NAUCLEFINE; PROTEIN BCL 2; PROTEIN BCL XL; PROTEIN P53; REACTIVE OXYGEN METABOLITE; SUBDITINE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BARK; CANCER CELL; CANCER CELL CULTURE; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION ASSAY; CELL STRAIN LNCAP; CELL STRAIN PC 3; CONTROLLED STUDY; CYTOSKELETON; DOWN REGULATION; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG PURIFICATION; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVATION; EPITHELIUM CELL; GENE EXPRESSION PROFILING; HUMAN; HUMAN CELL; IC 50; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MEDICINAL PLANT; MITOCHONDRIAL MEMBRANE POTENTIAL; NAUCLEA SUBDITA; PROSTATE CANCER; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; REAL TIME POLYMERASE CHAIN REACTION; ULTRAVIOLET SPECTROSCOPY; UPREGULATION; WESTERN BLOTTING; WILD TYPE;

ALKALOIDS; APOPTOSIS; BLOTTING, WESTERN; CASPASES; CELL LINE, TUMOR; CELL NUCLEUS; CYTOCHROMES C; CYTOSKELETON; DNA FRAGMENTATION; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME ACTIVATION; GENE EXPRESSION REGULATION, NEOPLASTIC; GLUTATHIONE REDUCTASE; HUMANS; INDOLE ALKALOIDS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MEMBRANE POTENTIAL, MITOCHONDRIAL; MODELS, BIOLOGICAL; PLANT BARK; PROSTATIC NEOPLASMS; QUINOLIZIDINES; REACTIVE OXYGEN SPECIES; TERPENES;

EID: 84895898066     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0087286     Document Type: Article

References (47)

1. Ahmad R, Mahbob ENM, Noor ZM, Ismail NH, Lajis NH, et al. (2010) Evaluation of antioxidant potential of medicinal plants from Malaysian Rubiaceae (subfamily Rubioideae). Afr J Biotechnol 9: 7948-7954.
2. Sichaem J, Surapinit S, Siripong P, Khumkratok S, Jong-aramruang J, et al. (2010) Two new cytotoxic isomeric indole alkaloids from the roots of Nauclea orientalis. Fitoterapia 81: 830-833.
3. Ng FSP, Whitmore TC (1989) Tree flora of Malaya: a manual for foresters: Longman Malaysia.
4. Fatin RJ, Wahab R, Daud JM, Sudin M, Rasat MS, et al. (2012) Study on Methanolic Extracts of Nauclea subdita (Korth) Steud. Heartwood Parts for the Total Phenolic Contents and Free Radical Scavenging Activities. Current Research Journal of Biological Sciences 4: 600-607.
5. Liew SY, Mukhtar MR, Hadi AHA, Awang K, Mustafa MR, et al. (2012) Naucline, a New Indole Alkaloid from the Bark of Nauclea officinalis. Molecules 17: 4028-4036.
6. Zhang Z, ElSohly HN, Jacob MR, Pasco DS, Walker LA, et al. (2001) New Indole Alkaloids from the Bark of Nauclea orientalis. J Nat Prod 64: 1001-1005. (Pubitemid 32800326)
7. Zeches M, Richard B, Gueye-M'Bahia L, Men-Olivier LL, Delaude C (1985) Constituents of root bark of Nauclea pobeguinii. J Nat Prod 48: 42-46.
8. Ngo Bum E, Taiwe GS, Moto FCO, Ngoupaye GT, Nkantchoua GCN, et al. (2009) Anticonvulsant, anxiolytic, and sedative properties of the roots of Nauclea latifolia Smith in mice. Epilepsy Behav 15: 434-440.
9. Erdelmeier CAJ, Regenass U, Rali T, Sticher O (1992) Indole Alkaloids with in vitro Antiproliferative Activity from the Ammoniacal Extract of Nauclea orientalis. Planta Med 58: 43-48.
10. Costello LC, Franklin RB (2000) The intermediary metabolism of the prostate: a key to understanding the pathogenesis and progression of prostate malignancy. Oncology 59: 269-282.
11. Liew SY, Mukhtar MR, Awang K, Mustafa MR, Ng SW (2011) 1-(1-Hydroxyethyl)-7,8-dihydroindolo[2,3-a]pyridine[3,4-g]quinolizin-5(13H)-one (angustoline) monohydrate from Nauclea subdita (Rubiaceae). Acta Crystallogr Sect E Struct Rep Online 67: o1727-o1728.
12. Mukhtar MR, Osman N, Awang K, Hazni H, Qureshi AK, et al. (2011) Neonaucline, a New Indole Alkaloid from the Leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae). Molecules 17: 267-274.
13. Qureshi AK, Mukhtar MR, Hirasawa Y, Hosoya T, Nugroho AE, et al. (2011) Neolamarckines A and B, New Indole Alkaloids from Neolamarckia cadamba. Chem Pharm Bull 59: 291-293.
14. Awang K, Lim CS, Mohamad K, Morita H, Hirasawa Y, et al. (2007) Erythrocarpines A-E, new cytotoxic limonoids from Chisocheton erythrocarpus. Bioorg Med Chem 15: 5997-6002. (Pubitemid 47043463)
15. Awang K, Chan G, Litaudon M, Ismail NH, Martin MT, et al. (2010) 4-Phenylcoumarins from Mesua elegans with acetylcholinesterase inhibitory activity. Bioorg Med Chem 18: 7873-7877.
16. Hotellier F, Delaveau P, Pousset JL (1975) Nauclefine et naucletine deux nouveaux alcaloides de type indoloquinolizidine isoles du Nauclea latifolia. Phytochemistry 14: 1407-1409.
17. Fan L, Fan C, Wang Y, Zhang X, Zhang Q, et al. (2010) Alkaloids from the leaves of Nauclea officinalis. Yao Xue Xue Bao 45: 747-751.
18. Abreu P, Pereira A (1998) A New Indole Alkaloid from Sarcocephalus latifolius. Heterocycles 48: 885-891. (Pubitemid 128657504)
19. Au TY, Cheung HT, Sternhell S (1973) New corynanthe alkaloids from Strychnos angustiflora. J Chem Soc Perkin 1: 13-16.
20. Batchily F, Mehri H, Plat M, Sevenet T (1986) Alkaloids from Neisosperma kilneri (F.V. Mueller) Fosberg et Sachet. Ann Pharm Fr 43: 513-520. (Pubitemid 16109797)
21. Phillipson JD, Hemingway SR, Bisset NG, Houghton PJ, Shellard EJ (1974) Angustine and related alkaloids from species of Mitragyna, nauclea, uncaria, and Strychnos. Phytochemistry 13: 973-978.
22. Sainsbury M, Uttley NL (1976) Synthesis of the indolo[2′,2′: 3,4]pyrido[1,2-b] [2,7]naphthyridinone alkaloid nauclefine and its ring-E isomers. J Chem Soc Perkin 1: 2416-2418.
23. Sainsbury M, Webb B (1975) Parvine, a new angustine-type alkaloid from Nauclea parva. Phytochemistry 14: 2691-2693.
24. Gummadi VR, Rajagopalan S, Looi CY, Paydar M, Renukappa GA, et al. (2013) Discovery of 7- azaindole based anaplastic lymphoma kinase (ALK) inhibitors: Wild type and mutant (L1196M) active compounds with unique binding mode. Bioorg Med Chem Lett 23: 4911-4918.
25. Looi CY, Moharram B, Paydar M, Wong YL, Leong KH, et al. (2013) Induction of apoptosis in melanoma A375 cells by a chloroform fraction of Centratherum anthelminticum (L.) seeds involves NF-kappaB, p53 and Bcl-2-controlled mitochondrial signaling pathways. BMC Comp Alt Med 13: 166.
26. Looi CY, Arya A, Cheah FK, Muharram B, Leong KH, et al. (2013) Induction of Apoptosis in Human Breast Cancer Cells via Caspase Pathway by Vernodalin Isolated from Centratherum anthelminticum (L.) Seeds. PLoS ONE 8: e56643.
27. Arbab IA, Looi CY, Abdul AB, Cheah FK, Wong WF, et al. (2012) Dentatin Induces Apoptosis in Prostate Cancer Cells via Bcl-2, Bcl-xL, Survivin Downregulation, Caspase-9, -3/7 Activation, and NF-kB Inhibition. Evid Based Complement Alternat Med: 856029.
28. Looi CY, Imanishi M, Takaki S, Sato M, Chiba N, et al. (2011) Octa-Arginine Mediated Delivery of Wild-Type Lnk Protein Inhibits TPO-Induced M-MOK Megakaryoblastic Leukemic Cell Growth by Promoting Apoptosis. PLoS ONE 6: e23640.
29. Sun J, Lou H, Dai S, Xu H, Zhao F, et al. (2008) Indole alkoloids from Nauclea officinalis with weak antimalarial activity. Phytochemistry 69: 1405-1410.
30. Atta-Ur-Rahman, Basha A (1982) Biosynthesis of Indole Alkaloids.
31. Cryns V, Yuan J (1998) Proteases to die for. Genes Dev 12: 1551-1570. (Pubitemid 28299508)
32. Pop C, Salvesen GS (2009) Human Caspases: Activation, Specificity, and Regulation. J Biol Chem 284: 21777-21781.
33. Li QQ, Wang G, Huang F, Banda M, Reed E (2010) Antineoplastic effect of β-elemene on prostate cancer cells and other types of solid tumour cells. J Pharm Pharmacol 62: 1018-1027.
34. Kim JY, Chung JY, Lee SG, Kim YJ, Park JE, et al. (2013) p53 interferes with microtubule-stabilizing agent-induced apoptosis in prostate and colorectal cancer cells. Int J Mol Med 31: 1388-1394.
35. Placzek WJ, Wei J, Kitada S, Zhai D, Reed JC, et al. (2010) A survey of the anti-apoptotic Bcl-2 subfamily expression in cancer types provides a platform to predict the efficacy of Bcl-2 antagonists in cancer therapy. Cell Death and Dis 1: e40.
36. Krajewska M, Krajewski S, Epstein JI, Shabaik A, Sauvageot J, et al. (1996) Immunohistochemical analysis of bcl-2, bax, bcl-X, and mcl-1 expression in prostate cancers. Am J Pathol 148: 1567-1576. (Pubitemid 26135897)
37. Gross A, McDonnell JM, Korsmeyer SJ (1999) BCL-2 family members and the mitochondria in apoptosis. Genes Dev 13: 1899-1911. (Pubitemid 29407357)
38. Gottlieb E, Vander Heiden MG, Thompson CB (2000) Bcl-xL Prevents the Initial Decrease in Mitochondrial Membrane Potential and Subsequent Reactive Oxygen Species Production during Tumor Necrosis Factor Alpha-Induced Apoptosis. Mol Cell Biol 20: 5680-5689. (Pubitemid 30482901)
39. Hu Y, Benedict MA, Wu D, Inohara N, Nunez G (1998) Bcl-XL interacts with Apaf-1 and inhibits Apaf-1-dependent caspase-9 activation. Proc Natl Acad Sci USA 95: 4386-4391.
40. Catz SD, Johnson JL (2003) BCL-2 in prostate cancer: a minireview. Apoptosis 8: 29-37. (Pubitemid 36133135)
41. Lebedeva I, Rando R, Ojwang J, Cossum P, Stein CA (2000) Bcl-xL in Prostate Cancer Cells: Effects of Overexpression and Down-Regulation on Chemosensitivity. Cancer Res 60: 6052-6060.
42. Raffo AJ, Perlman H, Chen MW, Day ML, Streitman JS, et al. (1995) Overexpression of bcl-2 Protects Prostate Cancer Cells from Apoptosis in Vitro and Confers Resistance to Androgen Depletion in Vivo. Cancer Res 55: 4438-4445.
43. Lebedeva IV, Sarkar D, Su ZZ, Kitada S, Dent P, et al. (2003) Bcl-2 and Bcl-xL differentially protect human prostate cancer cells from induction of apoptosis by melanoma differentiation associated gene-7, mda-7/IL-24. Oncogene 22: 8758-8773. (Pubitemid 38010500)
44. Fritsche M, Haessler C, Brandner G (1993) Induction of nuclear accumulation of the tumor-suppressor protein p53 by DNA-damaging agents. Oncogene 8: 307-318. (Pubitemid 23073746)
45. Smith ML, Fornace AJ Jr (1996) Mammalian DNA damage-inducible genes associated with growth arrest and apoptosis. Mutat Res 340: 109-124. (Pubitemid 126657371)
46. Rokhlin OW, Gudkov AV, Kwek S, Glover RA, Gewies AS, et al. (2000) p53 is involved in tumor necrosis factor-alpha-induced apoptosis in the human prostatic carcinoma cell line LNCaP. Oncogene 19: 1959-1968. (Pubitemid 30219039)
47. Meulmeester E, Jochemsen AG (2008) p53: a guide to apoptosis. Curr Cancer Drug Targets 8: 87-97. (Pubitemid 351347244)