Antibacterial benzofuran neolignans and benzophenanthridine alkaloids from the roots of Zanthoxylum capense

Planta Medica

Volumn 78, Issue 2, 2012, Pages 148-153

  Luo, Xuan ^a   Pedro, Liliana ^a   Milic, Vladimir ^a,b   Mulhovo, Silva ^c   Duarte, Aida ^a   Duarte, Noélia ^a   Ferreira, Maria José U ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b UNIVERSITY OF LONDON   (United Kingdom)

^c Universidade Pedagógica Campus de Lhanguene   (Mozambique)

Author keywords

2 arylbenzofuran neolignans; antibacterial activity; benzophenanthridine alkaloids; Rutaceae; Staphylococcus aureus; Zanthoxylum capense (Thunb.) Harv.

Indexed keywords

6 ACETONYLDIHYDROCHELERYTHRINE; 6 ACETONYLDIHYDRONITIDINE; ALKALOID; ANTIBIOTIC AGENT; DECARINE; DIHYDROCHELERYTHRINE; GENTAMICIN; KANAMYCIN; NEOLIGNAN; NORCHELERYTHRINE; TRIDECANONCHELERYTHRINE; UNCLASSIFIED DRUG; ZANTHOCAPENSATE; ZANTHOCAPENSINE; ZANTHOCAPENSOL;

ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; HETERONUCLEAR MULTIPLE BOND CORRELATION; IN VITRO STUDY; INFRARED SPECTROSCOPY; MEDICINAL PLANT; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; ZANTHOXYLUM CAPENSE;

ALKALOIDS; ANTI-BACTERIAL AGENTS; BACTERIA; BENZOPHENANTHRIDINES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT ROOTS; STAPHYLOCOCCUS AUREUS; ZANTHOXYLUM;

NEGIBACTERIA; POSIBACTERIA; RUTACEAE; STAPHYLOCOCCUS AUREUS; ZANTHOXYLUM;

EID: 84856270569     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0031-1280289     Document Type: Article

References (30)

1. Sun X W., Duan Z X. Progress in the studies on medicinal plants of the genus Zanthoxylum Linn. Acta Pharm Sin 1996 31 231-240
2. Yang C H., Cheng M J., Chiang M Y., Kuo Y H., Wang C J., Chen I S. Dihydrobenzo[c]phenanthridine alkaloids from stem bark of Zanthoxylum nitidum. J Nat Prod 2008 71 669-673 (Pubitemid 351656203)
3. Calaerwood J M., Finkelstein N, Fish F. Constituents of the stem and root barks of Fagara capensis (Thunb.). Phytochemistry 1970 9 675
4. He W, Van Puyvelde L, Kimpe N D., Verbruggen L, Anthonissen K, Van der Flaas M, Bosselaers J, Mathenge S G., Mudida F P. Chemical constituents and biological activities of Zanthoxylum usambarense. Phytother Res 2002 16 66-70 (Pubitemid 34116699)
5. Ross S A., Al-Azeib M A., Krishnaveni K S., Fronczek F R., Burandt C L. Alkamides from the leaves of Zanthoxylum syncarpum. J Nat Prod 2005 68 1297-1299 (Pubitemid 41291286)
6. Chen I S., Lin Y C., Tsai I L., Teng C M., Ko F N., Ishikawa T, Ishii H. Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium. Phytochemistry 1995 39 1091-1097
7. Fish F, Waterman P G., Finkelstein N. Sesamin from the bark of two African Zanthoxylum species. Phytochemistry 1973 12 2553-2554
8. Chen J J., Wang T Y., Hwang T L. Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae. J Nat Prod 2008 71 212-217
9. Schmidt E, Lötter M, McCleland W. Trees and shrubs of Mpumalanga and Kruger National Park. Johannesburg Jacana 2002 238
10. Steyn P S., Van Den Heever J P., Vosloo H C. M., Ackerman L G. J. Biologically active substances from Zanthoxylum capense (thunb.) Harv. S Afr J Sci 1998 94 391-393 (Pubitemid 28539972)
11. Ward R S. Lignans, neolignans and related compounds. Nat Prod Rep 1999 16 75-96 (Pubitemid 29092071)
12. Sheen W S., Tsai I L., Teng C M., Chen I S. Nor-neolignan and phenyl propanoid from Zanthoxylum ailanthoides. Phytochemistry 1994 36 213-215
13. Rao M L. N., Awasthi D K., Banerjee D. An expeditious and convergent synthesis of ailanthoidol. Tetrahedron Lett 2010 51 1979-1981
14. Segal R, Milo-Goldzweig I, Sokoloff S, Zitscek D V. A new benzofuran from the seeds of Styrax officinalis L. J Chem Soc C 1967 2402-2404
15. Zhang J, Zhang Y, Zhang Y, Herndon J W. Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: total synthesis of egonol. Tetrahedron 2003 59 5609-5616 (Pubitemid 36792235)
16. Gonzaga W A., Weber A D., Giacomelli S R., Dalcol I I., Hoelzel S C. S., Morel A F. Antibacterial alkaloids from Zanthoxylum rhoifolium. Planta Med 2003 69 371-374 (Pubitemid 36578007)
17. Krane B D., Fabule M O., Shamma M. The benzophenanthridine alkaloids. J Nat Prod 1984 47 1-43 (Pubitemid 14167998)
18. Ramalhete C, Lopes D, Molnár J, Mulhovo S, Rosário V E., Ferreira M J. U. Karavilagenin C derivatives as antimalarials. Bioorg Med Chem 2011 19 330-338
19. Ramalhete C, Lopes D, Mulhovo S, Molnár J, Rosário V E., Ferreira M J. U. New antimalarials with a triterpenic scaffold from Momordica balsamina. Bioorg Med Chem 2010 18 5254-5260
20. Mansoor T A., Ramalho R M., Mulhovo S, Rodrigues C M., Ferreira M J. U. Induction of apoptosis in HuH-7 cancer cells by monoterpene and -carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans. Bioorg Med Chem Lett 2009 19 4255-4258
21. Mansoor T A., Ramalhete C, Molnár J, Mulhovo S, Ferreira M J. U. Tabernines AC, -carbolines from the leaves of Tabernaemontana elegans. J Nat Prod 2009 72 1147-1150
22. Duarte N, Jardanhazy A, Molnár J, Hilgeroth A, Ferreira M J. U. Synergistic interaction between p-glycoprotein modulators and epirubicin on resistant cancer cells. Bioorg Med Chem 2008 16 9323-9330
23. Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard, 8th edition. Wayne CLSI Publication 2008 M07-A8
24. Jen C M., Tsai I L., Horng D J., Chen I S. Isolation and structure determination of two new compounds from Zanthoxylum integrifoliolum. J Nat Prod 1993 56 2019-2021 (Pubitemid 23348584)
25. Martin M T., Rasoanaivo L H., Raharisololalao A. Phenanthridine alkaloids from Zanthoxylum madagascariense. Fitoterapia 2005 76 590-593 (Pubitemid 41749751)
26. Choi D H., Hwang J W., Lee H S., Yang D M., Jun J G. Highly effective total synthesis of benzofuran natural product egonol. Bull Korean Chem Soc 2008 29 1594-1596
27. Hwang J W., Choi D H., Jeon J H., Kim J K., Jun J G. Facile preparation of 2-arylbenzo[ b ]furan molecules and their anti-inflammatory effects. Bull Korean Chem Soc 2010 31 965-970
28. Fotie J, Bohle D S., Olivier M, Adelaida Gomez M, Nzimiro S. Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida. J Nat Prod 2007 70 1650-1653 (Pubitemid 350155422)
29. Pereda-Miranda R, Kaatz G W., Gibbons S. Polyacylated oligosaccharides from medicinal Mexican morning glory species as antibacterials and inhibitors of multidrug resistance in Staphylococcus aureus. J Nat Prod 2006 69 406-409
30. Rauckman B S., Tidwell M Y., Johnson J V., Roth B. 2,4-Diamino-5- benzylpyrimidines and analogs as antibacterial agents. 10. 2,4-Diamino-5-(6- quinolylmethyl)- and -[(tetrahydro-6-quinolyl)methyl] pyrimidine derivatives. Further specificity studies. J Med Chem 1989 32 1927-1935 (Pubitemid 19204382)