Methylenebissantin: A rare methylene-bridged bisflavonoid from Dodonaea viscosa which inhibits Plasmodium falciparum enoyl-ACP reductase

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 1, 2012, Pages 610-612

  Muhammad, Akhtar ^a   Anis, Itrat ^a   Ali, Zulfiqar ^a,b   Awadelkarim, Sufyan ^c   Khan, Ajmal ^a   Khalid, Asaad ^c   Shah, Muhammad Raza ^a   Galal, M ^c   Khan, Ikhlas A ^b   Iqbal Choudhary, M ^a,d  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c National Center for Research Sudan   (Sudan)

^d KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Dodonaea viscosa; Methylene bridged bisflavonoid; Methylenebissantin; Plasmodium falciparum enoyl ACP reductase inhibition; Sapindaceae

Indexed keywords

(2,3)3,4',5,7 TETRAHYDROXYFLAVANONE; 6BETA HYDROXY 15,16 EPOXY 5BETA,8BETA,9BETA,10ALPHA CLERODA 3,13(16),14 TRIEN 18 OIC ACID; DITERPENOID; DOCOSYL CAFFEATE; DODONAEA VISCOSA EXTRACT; FLAVONOID; HAUTRIWAIC LACTONE; ISOKAEMPFERIDE; METHYLENEBISSANTIN; NEBRODENSIDE A; PHENOL DERIVATIVE; PINOCEMBRINE; PLANT EXTRACT; SANTIN; UNCLASSIFIED DRUG; VANILLIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DODONAEA VISCOSA; DRUG ISOLATION; IC 50; MEDICINAL PLANT; NONHUMAN; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; ENOYL-(ACYL-CARRIER-PROTEIN) REDUCTASE (NADH); ENZYME INHIBITORS; FLAVONES; FLAVONOIDS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; PLANT EXTRACTS; PLANTS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

DODONAEA VISCOSA; PLASMODIUM FALCIPARUM; SAPINDACEAE;

EID: 84655176307     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.10.072     Document Type: Article

References (38)

1. D.A. Fidock, P.J. Rosenthal, S.L. Croft, R. Brun, and S. Nwaka Nat. Rev. Drug Disc. 3 2004 509
2. Y.L. Fong, F.C. Cadigan, and G.R. Coatney Trans. R. Soc. Trop. Med. Hyg. 65 1971 839
3. A. Surolia, T.N.C. Ramya, V. Ramya, and N. Surolia Biochem. J. 383 2004 401
4. R.F. Waller, S.A. Ralph, M.B. Reed, V. Su, J.D. Douglas, D.E. Minnikin, A.F. Cowman, G.S. Besra, and G.I. McFadden Antimicrob. Agents Chemother. 47 2003 297
5. R.J.M. Wilson, P.W. Denny, P.R. Preiser, K. Rangachari, K. Roberts, A. Roy, A. Whyte, M. Strath, D.J. Moore, P.W. Moore, and D.H. Williamson J. Mol. Biol. 261 1996 155
6. J.Z. Lu, P.J. Lee, N.C. Waters, and S.T. Prigge Comb. Chem. High Throughput Screening 8 2005 15
7. R.F. Waller, S.A. Ralph, M.B. Reed, V. Su, J.D. Douglas, D.E. Minnikin, A.F. Cowman, G.S. Besra, and G.I. McFadden Antimicrob. Agents Chemother. 47 2003 297
8. C.O. Rock, and J.E. Cronan Biochim. Biophys. Acta 1302 1996 1
9. K. Magnuson, S. Jackowski, C.O. Rock, and J.E. Cronan Jr. Microbiol. Rev. 57 1993 522
10. J. Wiesner, and F. Seeber Expert Opin. Ther. Targets 9 2005 23
11. R. Perozzo, M. Kuo, A.b.S. Sidhu, J.T. Valiyaveettil, R. Bittman, W.R. Jacobs Jr., D.A. Fidock, and J.C. Sacchettini J. Biol. Chem. 277 2002 13106
12. N. Surolia, and A. Surolia Nat. Med. 7 2001 167
13. P. Abdullah Sapindaceae E. Nasir, S.I. Ali, Flora of West Pakistan Vol. 39 1973 Stewart Herbarium Gordon College, Rawalpindi 1
14. R. Mata, J.L. Contreras, D. Crisanto, R. Pereda-Miranda, P. Castaneda, and R.F. Del J. Nat. Prod. 54 1991 913
15. A.J. Pirzada, W. Shaikh, K. Usmanghani, and E. Mohiuddin Pak. J. Pharm. Sci. 23 2010 337
16. C. Clarkson, V.J. Maharaj, N.R. Crouch, O.M. Grace, P. Pillay, M.G. Matsabisa, N. Bhagwandin, P.J. Smith, and P.I. Folb J. Ethnopharmacol. 92 2004 177
17. H. Ahmad, A. Ahmad, and M.M. Jan J. Biol. Sci. 2 2002 175
18. M. Khurram, M.A. Khan, A. Hameed, N. Abbas, A. Qayum, H. Inayat, and D.G. Haq Molecules 14 2009 1332
19. Y. Deng, J.P. Lee, M. Tianasoa-Ramamonjy, J.K. Snyder, S.A.D. Etages, D. Kanada, M.P. Snyder, and C.J. Turner J. Nat. Prod. 63 2000 1082
20. G. Yao, Y. Ding, J. Zuo, H. Wang, Y. Wang, B. Ding, P. Chiu, and G. Qin J. Nat. Prod. 68 2005 392
21. H. Ito, N. Kasajima, H. Tokuda, H. Nishino, and T. Yoshida J. Nat. Prod. 67 2004 411
22. J.N. Roitman, R.Y. Wong, and E. Wollenweber Phytochemistry 34 1993 297
23. D.B. De Oliveira, A.P. de Almeida, B.A. De, G.L. Simões, C. Auvin, C.R. Kaiser, and S.S. Costa Planta Med. 69 2003 382
24. M. Iinuma, Y. Kakuto, N. Tanida, T. Tanaka, and F.A. Lang Phytochemistry 44 1997 705
25. K. Nakashima, N. Abe, F. Kamiya, T. Ito, M. Oyama, and M. Iinuma Helv. Chim. Acta 92 2009 1999
26. The plant material was collected from the hills of Kurram Agency, Khyber-pakhtoonkhwa, Pakistan. The identification was done by Dr. Ijaz Khan, a plant taxanomist, Department of Botany, Post Graduate College, Kohat, Pakistan.
27. T.G. Payne, and P.R. Jefferies Tetrahedron 29 1973 2575
28. A. Mohammad, I. Anis, V. McKee, J.W.A. Frese, and M.R. Shah Acta Crystallogr., Sect, E 66 2010 2716
29. E. Wollenweber, and J.N. Roitman Nat. Prod. Commun. 2 2007 85
30. D. Ying-Chi, L. An-Shen, W. Chin-Chung, H. Pei-Wen, C. Yung-Husan, C. I-Hsiao, C. Shu-Li, Y. Hsin-Fu, L. Tilo, C. Fang-Rong, and W. Yang-Chang Planta Med. 75 2009 848
31. O. Wakako, O. Seiji, K. Hashida, A. Masakazu, and S. Doi Holzforschung 56 2002 493
32. A.G. Prescott, N.P.J. Stamford, G. Wheeler, and J.L. Firmin Phytochemistry 60 2002 589
33. A. Mohammad, I. Anis, V. McKee, J.W.A. Frese, and M.R. Shah Acta Crystallogr., Sect. E 66 2010 o2529
34. P.R. Jeffries, and T.G. Payne Tetrahedron Lett. 8 1967 4777
35. I. Anis, E. Anis, S. Ahmed, G. Mustafa, A. Malik, Z. Amtul, and Atta-ur-Rahman Helv. Chim. Acta 84 2001 649
36. Z. Haifeng, J. Renji, K. Jie, H. Xiaoling, L. Yan, Z. Changlong, Y. Fang, Z. Lele, F. Xiao, T. Wu, and X. Wu J. Agric. Food Chem. 58 2010 12717
37. F. Cottiglia, L. Bonsignore, L. Casu, D. Deidda, R. Pompei, M. Casu, and C. Floris Nat. Prod. Res. 19 2005 117
38. S. Dey, M. Deepak, M. Seety, P. D'Souza, A. Agarwal, and G.K. Sangli Nat. Prod. Res. 23 2009 1657