Two new tryptophan derivatives from the seed kernels of Entada rheedei: Effects on cell viability and HIV infectivity

Fitoterapia

Volumn 87, Issue 1, 2013, Pages 37-42

  Nzowa, L K ^a   Teponno, R B ^a   Tapondjou, L A ^a   Verotta, L ^b   Liao, Z ^c   Graham, D ^c   Zink, M C ^c   Barboni, L ^d  

^a UNIVERSITY OF DSCHANG   (Cameroon)

^b UNIVERSITY OF MILAN   (Italy)

^c JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Entada rheedei; HIV infection; Mimosaceae; Tryptophan derivatives

Indexed keywords

1 O METHYLGLUCOPYRANOSIDE; 3 O BETA D GLUCOPYRANOSYL BETA SITOSTEROL; 5 O BETA D GLUCOPYRANOSYL 2 HYDROXYPHENYLACETIC ACID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ENTADAMIDE A; HOMOGENTISIC ACID; MELATONIN; PLANT EXTRACT; SEROTONIN; TRYPTOPHAN DERIVATIVE; TRYPTORHEEDEI A; TRYPTORHEEDEI B; UNCLASSIFIED DRUG;

ARTICLE; CELL VIABILITY; DRUG ISOLATION; DRUG STRUCTURE; ENTADA RHEEDEI; ENZYME ACTIVATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MASS SPECTROMETRY; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PERIPHERAL BLOOD MONONUCLEAR CELL; PLANT SEED; PRIORITY JOURNAL; VIRUS REPLICATION;

ACQUIRED IMMUNODEFICIENCY SYNDROME; BRAIN; CELL LINE; CELL SURVIVAL; DOPAMINE; FABACEAE; GLUTAMIC ACID; HIV; HIV INFECTIONS; HUMANS; INDOLEAMINE-PYRROLE 2,3,-DIOXYGENASE; KYNURENINE; LEUKOCYTES, MONONUCLEAR; MELATONIN; MOLECULAR STRUCTURE; PLANT EXTRACTS; PSYCHOTROPIC DRUGS; SEEDS; SEROTONIN; TRYPTOPHAN; VIRUS REPLICATION;

EID: 84878103106     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2013.03.017     Document Type: Article

References (37)

1. L.A. Tapondjou, L.B.T. Nyaa, P. Tane, M. Ricciutelli, L. Quassinti, and M. Bramucci Cytotoxic and antioxidant triterpene saponins from Butyrospermum parkii (Sapotaceae) Carbohydr Res 346 2011 2699 2704
2. The International Plant Names Index Published on the Internet http://www.ipni.org 2008 [accessed 25 June 2012]
3. S.K. Dash, and S. Padhy Review on ethnomedicines for diarrhoea diseases from Orissa: prevalence versus culture J Hum Ecol 20 2006 59 64
4. Y. Uprety, H. Asselin, E.K. Boon, S. Yadav, and K.K.J. Shrestha Indigenous uses and bio-efficacy of medicinal plants in Rasuwa district, Central Nepal Ethnobiol Ethnomed 6 2010 3
5. M.B. Shivanna, and N. Rajakumar Traditional medico-botanical knowledge of local communities in Hosanagara Taluk of Shimoga District in Karnataka, India J Herbs Spices Med Plants 17 2001 291 317
6. A.L. Tapondjou, T. Miyamoto, J.-F. Mirjolet, N. Guilbaud, and M.-A. Lacaille-Dubois Pursaethosides A-E, triterpene saponins from Entada pursaetha J Nat Prod 68 2005 1185 1190
7. G. Cioffi, P.F. Dal, P. De Caprariis, R. Sanego, S. Marzocco, and G. Autore Antiproliferative triterpene saponins from Entada africana J Nat Prod 69 2006 1323 1329
8. F. Ikegami, I. Shibasaki, S. Ohmiya, N. Ruangrungsi, and I. Murakoshi Entadamide A, a new sulphur-containing amide from Entada phaseoloides seeds Chem Pharm Bull 33 1985 5153 5154
9. F. Ikegami, S. Ohmiya, N. Ruangrungsi, S.-I. Sakai, and I. Murakoshi Entadamide B, a second new sulphur-containing amide from Entada phaseoloides Phytochemistry 26 1987 1525 1526
10. F. Ikegami, T. Sekine, S. Duangteraprecha, N. Matsushita, N. Matsuda, and N. Ruangrungsi Entadamide C, a sulphur-containing amid from Entada phaseoloides Phytochemistry 28 1989 881 882
11. A.K. Barua, M. Chakrabarty, P.K. Datta, and S. Ray Phaseoloidin, a homogentisic acid glucoside from Entada phaseoloides Phytochemistry 27 1988 3259 3261
12. J. Dai, L.B.S. Kardono, S. Tsauri, K. Padmawinata, J.M. Pezzuto, and A.D. Kinghorn Phenylacetic acid derivatives and a thioamide glycoside from Entada phaseoloides Phytochemistry 30 1991 3749 3752
13. S. Sugimoto, K. Matsunami, and H. Otsuka Medicinal plants of Thailand. I: structures of rheedeiosides A-D and cis-entadamide A β-D-glucopyranoside from the seed kernels of Entada rheedei Chem Pharm Bull 59 2011 466 471
14. S. Sugimoto, K. Matsunami, and H. Otsuka Medicinal plants of Thailand. II: chemical studies on the seed kernels of Entada rheedei Sprengel J Nat Med 66 2012 552 557
15. K.L. Nzowa, L. Barboni, R.B. Teponno, M. Ricciutelli, G. Lupidi, and L. Quassinti Rheediinosides A and B, two antoproliferative and antioxidant triterpene saponins from Entada rheedii Phytochemistry 71 2010 254 261
16. A. Boasso, C.M. Royle, S. Doumazos, V.N. Aquino, M. Biasin, and L. Piacentini Overactivation of plasmacytoid dendritic cells inhibits antiviral T-cell responses: a model for HIV immunopathogenesis Blood 118 2011 5152 5162
17. R. Schwarcz, J.P. Bruno, P.J. Muchowski, and H.Q. Wu Kynurenines in the mammalian brain: when physiology meets pathology Nat Rev Neurosci 13 2012 465 477
18. A. Boasso, J.P. Herbeuval, A.W. Hardy, S.A. Anderson, M.J. Dolan, and D. Fuch HIV inhibits CD4 + T-cell proliferation by inducing indoleamine 2,3-dioxygenase in plasmacytoid dendritic cells Blood 109 2007 3351 3359
19. M. Elbandy, T. Miyamoto, C. Delaude, and M.-A. Lacaille-Dubois Acylated preatroxigenin glycosides from Atroxima congolana J Nat Prod 66 2003 1154 1158
20. J.W. Roos, M.F. Maughan, Z. Liao, J.E. Hildreth, and J.E. Clements LuSIV cells: a reporter cell line for the detection and quantitation of a single cycle of HIV and SIV replication Virology 273 2000 307 315
21. Y. Matsumura, Y. Shibata, and T. Mimura The isolation of homogentisic glucoside from bamboo shoot Wakayama Igaku 13 1962 71 76
22. P.K. Agrawal NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides Phytochemistry 31 1992 3307 3330
23. R.B. Teponno, A.L. Tapondjou, D. Gatsing, J.D. Djoukeng, E. Abou-Mansour, and R. Tabacchi Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa Phytochemistry 67 2006 1957 1963
24. E. Fattorusso, V. Lanzotti, S. Magno, and E. Novellino Trytophan derivatives from a Mediterranean anthozoan Astroides calycularis J Nat Prod 48 1985 924 927
25. A.F. Carey Organic Chemistry 6th ed. 2006 McGraw-Hill New York
26. M. Schnabel, B. Rompp, D. Ruckdeschel, and C. Unverzagt Synthesis of trytophan N-glucoside Tetrahedron Lett 45 2004 295 297
27. S. Diem, J. Bergmann, and M. Herderch Tryptophan-N-glucoside in fruits and fruit juices J Agr Food Chem 48 2000 4913 4917
28. P.O. Larsen, E. Pedersen, H. Sorensen, and P. Sorup Tyrosine O-glucoside and dopamine 3-0-glucoside in seeds of Entada pursaetha Phytochemistry 12 1973 2243 2247
29. S. Carteau, J.F. Mouscadet, H. Goulaouic, F. Subra, and C. Auclair Inhibitory effect of the polyanionic drug suramin on the in vitro HIV DNA integration reaction Arch Biochem Biophys 305 1993 606 610
30. D.J. Hazuda, A.L. Wolfe, P.J. Felock, J.C. Hastings, B.C. Uncapher, and W.A. Schleif Inhibition of HIV-1 integrase by small molecular weight sulfonates 3rd Conference on Retroviruses and Opportunistic Infections, Washington DC 1996
31. D. Favre, J. Mold, P.W. Hunt, B. Kanwar, P. Loke, and L. Seu Tryptophan catabolism by indoleamine 2,2-dioxygenase 1 alters the balance of TH17 to regulatory T cells in HIV disease Sci Transl Med 2 2010 1 12
32. N.W.S. Davies, G. Guillemin, and B.J. Brew Tryptophan, neurodegeneration and HIV-associated neurocognitive disorder Int J Trypt Res 3 2010 121 140
33. X.W. Zeng, N. Huang, H. Xu, W.B. Yang, L.M. Yang, and H. Qu Anti human immunodeficiency virus type 1 (HIV-1) agents 4. Discovery of 5,5′-(p-phenylenebisazo)-8-hydroxyquinoline sulfonates as new HIV-1 inhibitors in vitro Chem Pharm Bull 58 2010 976 979
34. L.M. Rudensey, M.D. Papenhausen, and J. Overbaugh Replication and persistence of simian immunodeficiency virus variants after passage in macaque lymphocytes and established human cell lines J Virol 67 1993 1727 1733
35. L. Capece, A. Lewis-Ballester, M.A. Marti, D.A. Estrin, and S.R. Yeh Molecular basis for the substrate stereoselectivity in tryptophan dioxygenase Biochemistry 50 2011 10910 10918
36. M. Zamanakou, A.E. Germenis, and V. Karanikas Tumor immune escape mediated by indoleamine 2,3-dioxygenase Immunol Lett 111 2007 69 75
37. M. Vaccari, A. Boasso, C. Fenizia, D. Fuchs, A. Hryniewicz, and T. Morgan Fatal pancreatitis in simian immunodeficiency virus SIV(mac251)-infected macaques treated with 2′,3′-dideoxyinosine and stavudine following cytotoxic-T-lymphocyte-associated antigen 4 and indoleamine 2,3-dioxygenase blockade J Virol 86 2012 108 113