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The antiprotozoal activity of sixteen asteraceae species native to Sudan and bioactivity-guided isolation of xanthanolides from Xanthium brasilicum.
Planta Med. 2009 Oct; 75(12):1363-8.PM

Abstract

In vitro screening of the dichloromethane extracts of 16 Asteraceae species native to Sudan for activity against major protozoan pathogens revealed that a Xanthium brasilicum Vell. [syn. X. strumarium var. brasilicum (Vell.) Baker in Mart.] extract was the most active against Trypanosoma brucei rhodesiense, the etiological agent of East African human trypanosomiasis (IC(50) = 0.1 microg/mL). This plant extract also exhibited noticeable activities against T. cruzi (Chagas disease), Leishmania donovani (Kala-Azar) as well as Plasmodium falciparum (Malaria tropica). Bioactivity-guided fractionation resulted in the isolation of four bioactive sesquiterpene lactones (STL) of the xanthanolide series (4,5-seco-guaianolide-type). They were identified by spectroscopic means as 8-epixanthatin (1), 8-epixanthatin 1beta,5beta-epoxide (2), and as the dimers pungiolide A (4) as well as pungiolide B (5). Two further modified xanthanolide sesquiterpene lactones, xanthipungolide (3) and 4,15-dinor-1,11(13)-xanthadiene-3,5beta:12,8beta-diolide (6) were isolated. While xanthipungolide turned out to be inactive against the tested parasites, the dinor-xanthanlide showed significant activity against T. brucei rhodesiense and L. donovani. All isolated compounds were previously known from other Xanthium species but this is the first report on their occurrence in X. brasilicum, and, most notably, on their antiprotozoal activity. As the most active single compound from this extract, 8-epixanthatin 1beta,5beta-epoxide showed IC(50) values of 0.09, 2.95, 0.16 and 1.71 microg/mL (0.33, 11.3, 0.6 and 6.5 microM) against T. brucei rhodesiense, T. cruzi, L. donovani and P. falciparum, respectively, while its cytotoxicity against rat myoblast cells used as control was determined at 5.8 microg/mL (22.1 microM). Besides assessment of their antiprotozoal activity, the structural assignments for the dimeric xanthanolides pungiolide A and B were reinvestigated and fully established.

Authors+Show Affiliations

Institut für Pharmazeutische Biologie und Phytochemie IPBP, Westfälische Wilhelms-Universität Münster, Münster, Germany.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19431098

Citation

Nour, Amal M M., et al. "The Antiprotozoal Activity of Sixteen Asteraceae Species Native to Sudan and Bioactivity-guided Isolation of Xanthanolides From Xanthium Brasilicum." Planta Medica, vol. 75, no. 12, 2009, pp. 1363-8.
Nour AM, Khalid SA, Kaiser M, et al. The antiprotozoal activity of sixteen asteraceae species native to Sudan and bioactivity-guided isolation of xanthanolides from Xanthium brasilicum. Planta Med. 2009;75(12):1363-8.
Nour, A. M., Khalid, S. A., Kaiser, M., Brun, R., Abdallah, W. E., & Schmidt, T. J. (2009). The antiprotozoal activity of sixteen asteraceae species native to Sudan and bioactivity-guided isolation of xanthanolides from Xanthium brasilicum. Planta Medica, 75(12), 1363-8. https://doi.org/10.1055/s-0029-1185676
Nour AM, et al. The Antiprotozoal Activity of Sixteen Asteraceae Species Native to Sudan and Bioactivity-guided Isolation of Xanthanolides From Xanthium Brasilicum. Planta Med. 2009;75(12):1363-8. PubMed PMID: 19431098.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The antiprotozoal activity of sixteen asteraceae species native to Sudan and bioactivity-guided isolation of xanthanolides from Xanthium brasilicum. AU - Nour,Amal M M, AU - Khalid,Sami A, AU - Kaiser,Marcel, AU - Brun,Reto, AU - Abdallah,Wai'l E, AU - Schmidt,Thomas J, Y1 - 2009/05/08/ PY - 2009/5/12/entrez PY - 2009/5/12/pubmed PY - 2010/2/17/medline SP - 1363 EP - 8 JF - Planta medica JO - Planta Med. VL - 75 IS - 12 N2 - In vitro screening of the dichloromethane extracts of 16 Asteraceae species native to Sudan for activity against major protozoan pathogens revealed that a Xanthium brasilicum Vell. [syn. X. strumarium var. brasilicum (Vell.) Baker in Mart.] extract was the most active against Trypanosoma brucei rhodesiense, the etiological agent of East African human trypanosomiasis (IC(50) = 0.1 microg/mL). This plant extract also exhibited noticeable activities against T. cruzi (Chagas disease), Leishmania donovani (Kala-Azar) as well as Plasmodium falciparum (Malaria tropica). Bioactivity-guided fractionation resulted in the isolation of four bioactive sesquiterpene lactones (STL) of the xanthanolide series (4,5-seco-guaianolide-type). They were identified by spectroscopic means as 8-epixanthatin (1), 8-epixanthatin 1beta,5beta-epoxide (2), and as the dimers pungiolide A (4) as well as pungiolide B (5). Two further modified xanthanolide sesquiterpene lactones, xanthipungolide (3) and 4,15-dinor-1,11(13)-xanthadiene-3,5beta:12,8beta-diolide (6) were isolated. While xanthipungolide turned out to be inactive against the tested parasites, the dinor-xanthanlide showed significant activity against T. brucei rhodesiense and L. donovani. All isolated compounds were previously known from other Xanthium species but this is the first report on their occurrence in X. brasilicum, and, most notably, on their antiprotozoal activity. As the most active single compound from this extract, 8-epixanthatin 1beta,5beta-epoxide showed IC(50) values of 0.09, 2.95, 0.16 and 1.71 microg/mL (0.33, 11.3, 0.6 and 6.5 microM) against T. brucei rhodesiense, T. cruzi, L. donovani and P. falciparum, respectively, while its cytotoxicity against rat myoblast cells used as control was determined at 5.8 microg/mL (22.1 microM). Besides assessment of their antiprotozoal activity, the structural assignments for the dimeric xanthanolides pungiolide A and B were reinvestigated and fully established. SN - 1439-0221 UR - https://www.unboundmedicine.com/medline/citation/19431098/The_antiprotozoal_activity_of_sixteen_asteraceae_species_native_to_Sudan_and_bioactivity_guided_isolation_of_xanthanolides_from_Xanthium_brasilicum_ L2 - http://www.thieme-connect.com/DOI/DOI?10.1055/s-0029-1185676 DB - PRIME DP - Unbound Medicine ER -