Planta Medica Letters 2015; 2(01): e73-e77
DOI: 10.1055/s-0035-1558261
Letter
Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Norhopene Triterpenoids from the Bark of Exothea paniculata from Abaco Island, Bahamas

Bhuwan K. Chhetri
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, USA
,
Noura S. Dosoky
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, USA
,
William N. Setzer
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, USA
› Author Affiliations
Further Information

Publication History

received 25 September 2015
revised 25 September 2015

accepted 21 October 2015

Publication Date:
21 December 2015 (online)

Abstract

Bioactivity-directed preparative chromatography of the cytotoxic crude dichloromethane bark extract of Exothea paniculata has yielded two new cytotoxic norhopene triterpenoids, exotheol A and exotheol B. The structures were determined by nuclear magnetic resonance and high-resolution mass spectrometry and were found to be potently cytotoxic to MCF-7 and 5637 cells in vitro.

 
  • References

  • 1 Nickrent DL, Eshbaugh WH, Wilson TK. The vascular flora of Andros Island, Bahamas. Oxford, Ohio: Willard Sherman Turrell Herbarium, Miami University; 1991: 145-147
  • 2 Tropicos.org. Missouri botanical garden. Available at. http://www.tropicos.org/Name/28600911 Accessed September 6, 2015
  • 3 Mutchnick PA, McCarthy BC. An ethnobotanical analysis of the tree species common to the subtropical most forests of the Petén, Guatemala. Econ Bot 1997; 51: 158-183
  • 4 Schmidt JM, Noletto JA, Vogler B, Setzer WN. Abaco bush medicine: chemical composition of the essential oils of four aromatic medicinal plants from Abaco Island, Bahamas. J Herbs Spices Med Plants 2007; 12: 43-65
  • 5 Monzote L, Piñón A, Setzer WN. Antileishmanial potential of tropical rainforest plant extracts. Medicines 2014; 1: 32-55
  • 6 Setzer MC, Newby JS, Moriarity DM, Setzer WN. A phytopharmaceutical survey of Abaco, Island, Bahamas. Am J Essent Oils Nat Prod 2015; 2: 10-17
  • 7 Dictionary of Natural Products on DVD, v. 23: 2. Boca Raton, Florida: CRC Press; 2015
  • 8 Cheng L, Shen LM, Zhang M, Li N, Li X, Ma ZJ, Qu HB. Eleven new triterpenes from Eurycorymbus cavaleriei . Helv Chim Acta 2010; 93: 2263-2275
  • 9 Chávez JP, David JM, Yang SW, Cordell GA. 24-Norhopene derivatives from Diatenopteryx sorbifolia . J Nat Prod 1997; 60: 909-911
  • 10 Setzer WN, Setzer MC. Plant-derived triterpenoids as potential antineoplastic agents. Mini Rev Med Chem 2003; 3: 540-556
  • 11 Moriarity DM, Huang J, Yancey CA, Zhang P, Setzer WN, Lawton RO, Bates RB, Caldera S. Lupeol is the cytotoxic principle in the leaf extract of Dendropanax cf. querceti . Planta Med 1998; 64: 370-372
  • 12 Wada SI, Iida A, Tanaka R. Triterpene constituents from the stem bark of Pinus luchuensis and their DNA topoisomerase II inhibitory effect. Planta Med 2001; 67: 659-664
  • 13 Sturm S, Gil RR, Chai HB, Ngassapa OD, Santisuk T, Reutrakul V, Howe A, Moss M, Besterman JM, Yang SL, Farthing JE, Tait RM, Lewis JA, OʼNeill MJ, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD. Lupane derivatives from Lophopetalum wallichii with farnesyl protein transferase inhibitory activity. J Nat Prod 1996; 59: 658-663
  • 14 Chaturvedula VSP, Zhou BN, Gao Z, Thomas SJ, Hecht SM, Kingston DGI. New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase β . Bioorg Med Chem 2004; 12: 6271-6275
  • 15 Simon A, Najid A, Chulia AJ, Delage C, Rigaud M. Inhibition of lipoxygenase activity and HL60 leukemic cell proliferation by ursolic acid isolated from heather flowers (Calluna vulgaris). Biochim Biophys Acta 1992; 1125: 68-72
  • 16 Molegro Virtual Docker v 6.0.0. Aarhus, Denmark: Molegro ApS; 2013
  • 17 Thomsen R, Christensen MH. MolDock: a new technique for high-accuracy molecular docking. J Med Chem 2006; 49: 3315-3321
  • 18 Setzer MC, Setzer WN, Jackes BR, Gentry GA, Moriarity DM. The medicinal value of tropical rainforest plants from Paluma, North Queensland, Australia. Pharmaceut Biol 2001; 39: 67-78
  • 19 Classen S, Olland S, Berger JM. Structure of the topoisomerase II ATPase region and its mechanism of inhibition by the chemotherapeutic agent ICRF-187. Proc Natl Acad Sci U S A 2003; 100: 10629-10634
  • 20 Dong KC, Berger JM. Structural basis for gate-DNA recognition and bending by type IIA topoisomerases. Nature 2007; 450: 1201-1205
  • 21 Sawaya MR, Pelletier H, Kumar A, Wilson SH, Kraut J. Crystal structure of rat DNA polymerase beta: evidence for a common polymerase mechanism. Science 1994; 264: 1930-1935
  • 22 Gridley CL, Rangarajan S, Firbank S, Dalal S, Sweasy JB, Jaeger J. Structural changes in the hydrophobic hinge region adversely affect the activity and fidelity of the I260Q mutator DNA polymerase β . Biochemistry 2013; 52: 4422-4432
  • 23 Gilbert NC, Rui Z, Neau DB, Waight MT, Bartlett SG, Boeglin WE, Brash AR, Newcomer ME. Conversion of human 5-lipoxygenase to a 15-lipoxygenase by a point mutation to mimic phosphorylation at Serine-663. FASEB J 2012; 26: 3222-3229
  • 24 Long SB, Hancock PJ, Kral AM, Hellinga HW, Beese LS. The crystal structure of human protein farnesyltransferase reveals the basis for inhibition by CaaX tetrapeptides and their mimetics. Proc Natl Acad Sci U S A 2001; 98: 12948-12953
  • 25 Spartanʼ14 for Windows, v 1.1.8. Irvine, California: Wavefunction, Inc.; 2014
  • 26 Halgren TA. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF 94. J Comput Chem 1996; 17: 490-519