The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins

Journal of Ethnopharmacology

Volumn 147, Issue 1, 2013, Pages 232-237

  ONeill, Taryn ^a   Johnson, John A ^a   Webster, Duncan ^b   Gray, Christopher A ^a  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

^b SAINT JOHN REGIONAL HOSPITAL   (Canada)

Author keywords

(3R8S) falcarindiol; Antimycobacterial activity; C 17 diynes; Furanocoumarins; Heracleum maximum; Mycobacterium tuberculosis

Indexed keywords

6 ISOPENTENYLOXYISOBERGAPTEN; ALKYNE DERIVATIVE; ANGELICIN; ANTIMYCOBACTERIAL AGENT; BERGAPTEN; FALCARINDIOL; FUROCOUMARIN DERIVATIVE; HERACLEUM MAXIMUM EXTRACT; ISOBERGAPTEN; ISOPIMPINELLIN; PIMPINELLIN; RIFAMPICIN; SPHONDIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; FRACTIONATION; HERACLEUM; HERACLEUM MAXIMUM; IC 50; MASS SPECTROMETRY; MEDICINAL PLANT; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; POLARIMETRY;

ANTITUBERCULAR AGENTS; BIOLOGICAL ASSAY; CANADA; CHEMICAL FRACTIONATION; DIYNES; FLUOROMETRY; HERACLEUM; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; MICROBIAL SENSITIVITY TESTS; MICROSPECTROPHOTOMETRY; MYCOBACTERIUM TUBERCULOSIS; PHYTOTHERAPY; PLANT EXTRACTS; PLANT ROOTS; PLANTS, MEDICINAL; PSORALENS; SOLVENTS;

HERACLEUM MAXIMUM; MYCOBACTERIUM TUBERCULOSIS;

EID: 84876041960     PISSN: 03788741     EISSN: 18727573     Source Type: Journal    
DOI: 10.1016/j.jep.2013.03.009     Document Type: Article

References (49)

1. T.J. Batterham, and J.A. Lamberton Nuclear magnetic resonance spectra of angelicin and related compounds Australian Journal of Chemistry 17 1964 1305 1308
2. R.K. Bentley, D. Bhattach, E.R.H. Jones, and V. Thaller Natural acetylenes. Part XXVIII. C17-polyacetylenic alcohols from Umbellifer Daucus carota L. (Carrot): alkylation of benzene by acetylenyl(vinyl)carbinols in the presence of toluene-p-sulphonic acid Journal of the Chemical Society C: Organic 1969 685 688
3. D. Bergenthal, Z. Rozsa, I. Mester, and J. Reisch C-13 NMR spectroscopy of coumarins from Rutaceae Archiv der Pharmazie 311 1978 1026 1029 (Pubitemid 9072093)
4. F. Bohlmann, U. Niedball, and K.M. Rode Polyacetylenverbindungen, CXVIII. Uber neue polyine Mit C17-kette Chemische Berichte Recueil 99 1966 3552 3554
5. C.D. Carpenter, T. O'Neill, N. Picot, J.A. Johnson, G.A. Robichaud, D. Webster, and C.A. Gray Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis Journal of Ethnopharmacology 143 2012 695 700
6. L.A. Collins, and S.G. Franzblau Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium Antimicrobial Agents and Chemotherapy 41 1997 1004 1009 (Pubitemid 27194176)
7. S. Deng, Y. Wang, T. Inui, S.N. Chen, N.R. Farnsworth, S. Cho, S.G. Franzblau, and G.F. Pauli Anti-TB polyynes from the roots of Angelica sinensis Phytotherapy Research 22 2008 878 882
8. D.L. Dreyer Extractives of Angelica genuflexa Nutt Journal of Organic Chemistry 35 1970 2294 2297
9. D.J. Finney Probit Analysis 3rd ed. 1971 Cambridge University Press Cambridge 333 pp
10. J. Herzog, and V. Hâncu Zur kenntnis des pimpinellins Archiv der Pharmazie 246 1908 402 414
11. H.R. Hinds Flora of New Brunswick 2nd ed. 2000 University of New Brunswick Fredericton 695 pp
12. T. Inui, Y. Wang, D. Nikolic, D.C. Smith, S.G. Franzblau, and G.F. Pauli Sesquiterpenes from Oplopanax horridus Journal of Natural Products 73 2010 563 567
13. N.P. Jones, J.T. Arnason, M. Abou-Zaid, K. Akpagana, P. Sanchez-Vindas, and M.L. Smith Antifungal activity of extracts from medicinal plants used by First Nations peoples of eastern Canada Journal of Ethnopharmacology 73 2000 191 198
14. J.R. Kern, and J.H. Cardellina Native American medicinal plants. Falcarindiol and 3-O-methylfalcarindiol from Osmorhiza occidentalis Journal of Natural Products 45 1982 774 776 (Pubitemid 13180964)
15. M. Kobaisy, Z. Abramowski, L. Lermer, G. Saxena, R.E.W. Hancock, G.H.N. Towers, D. Doxsee, and R.W. Stokes Antimycobacterial polyynes of Devil's Club (Oplopanax horridus), a North American native medicinal plant Journal of Natural Products 60 1997 1210 1213 (Pubitemid 27516227)
16. A. Koul, E. Arnoult, N. Lounis, J. Guillemont, and K. Andries The challenge of new drug discovery for tuberculosis Nature 469 2011 483 490
17. L. Lacey MicMac Medicines 1993 Nimbus Publishing Limited Halifax 125 pp
18. D. Lechner, M. Stavri, M. Oluwatuyi, R. Pereda-Miranda, and S. Gibbons The anti-staphylococcal activity of Angelica dahurica (Bai Zhi) Phytochemistry 65 2004 331 335 (Pubitemid 38147346)
19. H. Li, T. O'Neill, D. Webster, J.A. Johnson, and C.A. Gray Anti-mycobacterial diynes from the Canadian medicinal plant Aralia nudicaulis Journal of Ethnopharmacology 140 2012 141 144
20. N. Mantel, K.C. Smith, J.L. Robertson, and N.E. Savin Maximum-likelihood vs minimum chi-square Biometrics 41 1985 777 781
21. H. Matsuda, T. Murakami, T. Kageura, K. Ninomiya, I. Toguchida, N. Nishida, and M. Yoshikawa Hepatoprotective and nitric oxide production inhibitory activities of coumarin and polyacetylene constituents from the roots of Angelica furcijuga Bioorganic & Medicinal Chemistry Letters 8 1998 2191 2196 (Pubitemid 28561604)
22. A.R. McCutcheon, S.M. Ellis, R.E.W. Hancock, and G.H.N. Towers Antibiotic screening of medicinal plants of the British Columbian native peoples Journal of Ethnopharmacology 37 1992 213 223
23. A.R. McCutcheon, S.M. Ellis, R.E.W. Hancock, and G.H.N. Towers Antifungal screening of medicinal plants of British Columbian native peoples Journal of Ethnopharmacology 44 1994 157 169
24. A.R. McCutcheon, T.E. Roberts, E. Gibbons, S.M. Ellis, L.A. Babiuk, R.E.W. Hancock, and G.H.N. Towers Antiviral screening of British Columbian medicinal plants Journal of Ethnopharmacology 49 1995 101 110 (Pubitemid 26010743)
25. A.R. McCutcheon, R.W. Stokes, L.M. Thorson, S.M. Ellis, R.E.W. Hancock, and G.H.N. Towers Anti-mycobacterial screening of British Columbian medicinal plants International Journal of Pharmacognosy 35 1997 77 83
26. W.H. Mechling The Malecite Indians with notes on the Micmacs Anthropologica 8 1959 239 263
27. D.E. Moerman Native American Ethnobotany 1998 Timber Press Portland 927 pp
28. B.J.T. Morgan Analysis of Quantal Response Data 1992 Chapman & Hall London 512 pp
29. T. Ohnuma, E. Anan, R. Hoashi, Y. Takeda, T. Nishiyama, K. Ogura, and A. Hiratsuka Dietary diacetylene falcarindiol induces phase 2 drug-metabolizing enzymes and blocks carbon tetrachloride-induced hepatotoxicity in mice through suppression of lipid peroxidation Biological & Pharmaceutical Bulletin 34 2011 371 378
30. C. Pomeranz Uber das Bergapten Monatshefte für Chemie - Chemical Monthly 12 1891 379 392
31. G.X. Rao, Y. Wu, W.S. Dai, Z.W. Lin, and H.D. Sun Coumarins of Heracleum yungningense Hand Mass Zhongguo Zhongyao Zazhi 18 1993 736 763
32. L. Santana, E. Uriarte, F. Roleira, N. Milhazes, and F. Borges Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity Current Medicinal Chemistry 11 2004 3239 3261 (Pubitemid 39534749)
33. A. Schinkovitz, M. Stavri, S. Gibbons, and F. Bucar Antimycobacterial polyacetylenes from Levisticum officinale Phytotherapy Research 22 2008 681 684 (Pubitemid 351716559)
34. J.L. Sebaugh Guidelines for accurate EC50/IC50 estimation Pharmaceutical Statistics 10 2011 128 134
35. J.M. Seco, E. Quinoa, and R. Riguera The assignment of absolute configuration by NMR Chemical Reviews 104 2004 17 117
36. N.M.M. Shalaby, H.I. Abd-Alla, H.H. Ahmed, and N. Basoudan Protective effect of Citrus sinensis and Citrus aurantifolia against osteoporosis and their phytochemical constituents Journal of Medicinal Plants Research 5 2011 579 588
37. Y.N. Sheinker, M.E. Perelson, and G.Y. Pek Nuclear magnetic resonance spectra of natural coumarins and furocoumarins Doklady Akademii Nauk SSSR 158 1964 1382 1385
38. E. Souri, H. Farsam, P. Sarkheil, and F. Ebadi Antioxidant activity of some furanocoumarins isolated from Heracleum persicum Pharmaceutical Biology 42 2004 396 399 (Pubitemid 40066055)
39. E. Spath, and M. Pailer The natural cumarine, XIII. Announcement. Synthesis of angelicin (from Angelica archangelica) Berichte der Deutschen Chemischen Gesellschaft 67 1934 1212 1213
40. E. Spath, and S. Raschka Concerning Heracline (IX Report on natural coumarines) Berichte der Deutschen Chemischen Gesellschaft 67 1934 62 63
41. M. Stavri, and S. Gibbons The antimycobacterial constituents of dill (Anethum graveolens) Phytotherapy Research 19 2005 938 941 (Pubitemid 41820231)
42. W. Steck, and B.K. Bailey Characterization of plant coumarins by combined gas chromatography ultraviolet absorption spectroscopy, and nuclear magnetic resonance analysis Canadian Journal of Chemistry 47 1969 3577 3583
43. S. Tamura, T. Ohno, Y. Hattori, and N. Murakami Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma Tetrahedron Letters 51 2010 1523 1525
44. M. Walker Wild Plants of Eastern Canada: Identifying, Harvesting and Using 2008 Nimbus Publishing, Halifax 203 pp
45. D. Webster, T.D.G. Lee, J. Moore, T. Manning, D. Kunimoto, D. LeBlanc, J.A. Johnson, and C.A. Gray Antimycobacterial screening of traditional medicinal plants using the microplate resazurin assay Canadian Journal of Microbiology 56 2010 487 494
46. D. Webster, P. Taschereau, T.D.G. Lee, and T. Jurgens Immunostimulant properties of Heracleum maximum Bartr Journal of Ethnopharmacology 106 2006 360 363
47. F. Wessely, and E. Nadler Uber die inhaltsstoffe der wurzel von Pimpinella saxifraga II Monatshefte für Chemie 60 1932 141 144
48. WHO, 2012. Global Tuberculosis Report 2012, pp. 1-272.
49. W.D. Wulff, J.S. Mccallum, and F.A. Kunng Two regiocomplementary approaches to angular furanocoumarins with chromium carbene complexes - synthesis of sphondin, thiosphondin, heratomin, and angelicin Journal of the American Chemical Society 110 1988 7419 7434 (Pubitemid 18260550)