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Planta Med 2013; 79(08): 661-665
DOI: 10.1055/s-0032-1328482
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Sesquiterpene Lactones from Aerial Parts of Xanthium sibiricum

Lun Wang
1   Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
2   Graduate University of Chinese Academy of Sciences, Beijing, China
,
Jing Wang
1   Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
2   Graduate University of Chinese Academy of Sciences, Beijing, China
,
Fu Li
1   Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
,
Xin Liu
3   Beijing Entry-Exit Inspection and Quarantine Bureau, Beijing, China
,
Bin Chen
1   Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
,
Ya-Xiong Tang
1   Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
,
Ming-Kui Wang
1   Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
› Author Affiliations
Further Information

Publication History

received 12 December 2012
revised 12 March 2013

accepted 21 March 2013

Publication Date:
23 May 2013 (online)

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Abstract

Chemical investigation of the aerial parts of Xanthium sibiricum led to the isolation of four new xanthanolide-type sesquiterpene lactones, including two xanthanolide dimers, pungiolide D (1) and pungiolide E (2), and two xanthanolide monomers, 8-epi-xanthatin-1α,5α-epoxide (3) and 1β-hydroxyl-5α-chloro-8-epi-xanthatin (4), together with four known compounds, pungiolide A (5), 8-epi-xanthatin-1β,5β-epoxide (6), xanthatin (7), and 11α,13-dihydro-8-epi-xanthatin (8). The structures of these compounds were elucidated on the basis of spectroscopic data analysis. Pungiolide D (1) displayed an unusual structure featuring a 5/5/6-fused tricyclic system in the unit B. Compound 4 was shown to be a rare sesquiterpene lactone containing halogen, and its absolute configuration was determined by X-ray crystallographic analysis. The evaluation of the cytotoxic activities of the isolated new compounds against the SNU387 liver and A-549 lung human cancer cell lines showed that compound 4 possessed significant in vitro cytotoxicity with an IC50 value of 5.1 µM against SNU387 liver cells.

Key words

Xanthium sibiricum - Compositae - sesquiterpene lactones - xanthanolides - cytotoxicity

Supporting Information

 

  • References

  • 1 Chen YL. Xanthium L. Flora Reipublicae Popularis Sinicae, Vol. 75. Beijing: Science Press; 1979
    Google Scholar
  • 2 Chinese Pharmacopoeia Committee. Pharmacopoeia of China, Part 1. Beijing: Chemical Industry Press; 2005: 111-112
    Google Scholar
  • 3 Winters TE, Geissmen TA, Safir D. Sesquiterpene lactones of Xanthium species. Xanthanol and isoxanthanol, and correlation of xanthinin with ivalbin. J Org Chem 1969; 34: 153-155
    CrossrefPubMedGoogle Scholar
  • 4 Mahmoud AA. Xanthanolides and xanthane epoxide derivatives from Xanthium strumarium . Planta Med 1998; 64: 724-727
    Article in Thieme ConnectPubMedGoogle Scholar
  • 5 Bui VB, Liu ST, Zhu JJ, Xiong J, Zhao Y, Yang GX, Xia G. Sesquiterpene lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines. Phytochem Lett 2012; 5: 685-689
    CrossrefPubMedGoogle Scholar
  • 6 Macleod JK, Moeller PD, Franke FP. Two toxic kaurene glycosides from the burrs of Xanthium pungens . J Nat Prod 1990; 53: 451-455
    CrossrefPubMedGoogle Scholar
  • 7 Ma YT, Huang MC, Hsu FL, Chang HF. Thiazinedione from Xanthium strumarium . Phytochemistry 1998; 48: 1083-1085
    CrossrefPubMedGoogle Scholar
  • 8 Qin LP, Han T, Li HL, Zhang QY, Zheng HC. A new thiazinedione from Xanthium strumarium . Fitoterapia 2006; 77: 245-246
    CrossrefPubMedGoogle Scholar
  • 9 Han T, Li HL, Zhang QY, Zheng HC, Qin LP. New thiazinediones and other components from Xanthium strumarium . Chem Nat Compd 2006; 42: 567-570
    CrossrefPubMedGoogle Scholar
  • 10 Dai YH, Cui Z, Li JL, Wang D. A new thiaziedione from the fruits of Xanthium sibiricum . J Asian Nat Prod Res 2008; 10: 303-305
    CrossrefPubMedGoogle Scholar
  • 11 Agata I, Goto S, Hatano T, Nishibe S, Okuda T. 1,3,5-Tri-O-caffeoylquinic acid from Xanthium strumarium . Phytochemistry 1993; 33: 508-509
    CrossrefPubMedGoogle Scholar
  • 12 Roussakis C, Chinou I, Vayas C, Harvala C, Verbist JF. Cytotoxic activity of xanthatin and the crude extracts of Xanthium strumarium . Planta Med 1994; 60: 473-474
    Article in Thieme ConnectPubMedGoogle Scholar
  • 13 Nour AMM, Khalid SA, Kaiser M, Brun R, Abdallah WE, Schmidt TJ. The antiprotozoal activity of sixteen Asteraceae species native to Sudan and bioactivity guided isolation of xanthanolides from Xanthium brasilicum . Planta Med 2009; 75: 1363-1368
    Article in Thieme ConnectPubMedGoogle Scholar
  • 14 Vasas A, Hohmann J. Xanthane sesquiterpenoids: structure, synthesis and biological activity. Nat Prod Rep 2011; 28: 824-842
    CrossrefPubMedGoogle Scholar
  • 15 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
    CrossrefPubMedGoogle Scholar
  • 16 Reed LJ, Muench H. A simple method of estimating fifty percent endpoints. Am J Hyg 1938; 27: 493-497
    PubMedGoogle Scholar
  • 17 Cumanda J, Marinoni G, Debernardi M, Vidari G, Finzi PV. New Sesquiterpenes from Xanthium catharticum . J Nat Prod 1991; 54: 460-465
    CrossrefPubMedGoogle Scholar
  • 18 Ahmed AA, Mahmoud AA, El-Gamal AA. A xanthanolide diol and a dimeric xanthanolide from Xanthium species. Planta Med 1999; 65: 470-472
    Article in Thieme ConnectPubMedGoogle Scholar
  • 19 Ahmed AA, Jakupovic J, Bohlmann F, Regaila HA, Ahmed AM. Sesquiterpene lactones from Xanthium pungens . Phytochemistry 1990; 29: 2211-2215
    CrossrefPubMedGoogle Scholar
  • 20 Omar AA, Elrashidy EM, Ghazy NA, Metwally AM, Ziesche J, Bohlmann F. Xanthanolides from Xanthium spinosum . Phytochemistry 1984; 23: 915-916
    CrossrefPubMedGoogle Scholar
  • 21 Bohlmann F, Singh P, Joshi KC, Singh CL. Xanthanolides from Xanthium indicum . Phytochemistry 1982; 21: 1441-1443
    CrossrefPubMedGoogle Scholar
  • 22 Deuel PG, Geissman TA. Xanthinin. II. The structures of xanthinin and xanthatin. J Am Chem Soc 1957; 79: 3778-3783
    CrossrefPubMedGoogle Scholar