Subscribe to RSS
DOI: 10.1055/s-2008-1081295
© Georg Thieme Verlag KG Stuttgart · New York
(−)-Xanthienopyran, a New Inhibitor of Superoxide Anion Generation by Activated Neutrophils, and Further Constituents of the Seeds of Xanthium strumarium
Publication History
Received: June 14, 2007
Revised: April 21, 2008
Accepted: May 22, 2008
Publication Date:
11 July 2008 (online)
Abstract
The dried seeds of Xanthium strumarium (Asteraceae) are used after thorough stir-frying as an ingredient in traditional Chinese medicines for relieving allergy. Two new compounds, xanthialdehyde (2) and (−)-xanthienopyran (7), as well as 26 known compounds were isolated in the present study. The structures of the isolates were elucidated by spectroscopic methods. Among them, compound 7 exhibited significant selective inhibition of superoxide anion generation by human neutrophils induced by formyl-L-methionyl-L-leucyl-L-phenylalanine, with an IC50 value of 1.72 μg/mL.
Key words
Xanthium strumarium - Asteraceae - Cang-Er Zi - superoxide anion generation inhibitor - neutrophils
References
- 1 Hwang T L, Hung H W, Kao S H, Teng C M, Wu C C, Cheng S J. Soluble guanylyl cyclase activator YC-1 inhibits human neutrophil functions through a cGMP-independent but cAMP-dependent pathway. Mol Pharmacol. 2003; 64 1419-27
- 2 Cronstein B N, Weissmann G. Targets for antiinflammatory drugs. Annu Rev Pharmacol Toxicol. 1995; 35 449-62
- 3 Brinkmann V, Reichard U, Goosmann C, Fauler B, Uhlemann Y, Weiss D S. et al . Neutrophil extracellular traps kill bacteria. Science. 2004; 303 1532-5
- 4 Jiangsu Medical College. Pharmacopoeia of Chinese medicine. Shanghai; Shanghai People Hygiene Publisher 1978
- 5 Han T, Li H L, Zhang Q Y, Han P, Zheng H C, Rahma K. et al . Bioactivity-guided fractionation for anti-inflammatory and analgesic properties and constituents of Xanthium strumarium L. Phytomedicine. 2007; 14 825-9
- 6 Kim I T, Park Y M, Won J H, Jung H J, Park H J, Choi J W. et al . Methanol extract of Xanthium strumarium L. possesses anti-inflammatory and anti-nociceptive activities. Biol Pharm Bull. 2005; 28 94-100
- 7 Ma Y T, Huang M C, Hsu F L, Chang H F. Thiazinedione from Xanthium strumarium. Phytochemistry. 1998; 48 1083-5
- 8 Mahmoud Ahmed A, Ahmed Ahmed A, Al-Shihry Shar S. A new heterocyclic glucoside from the fruits of Xanthium pungens. Nat Prod Res. 2005; 19 585-9
- 9 Marco J A, Sanz-Cervera J F, Corral J, Carda M, Jakupovic J. Xanthanolides from Xanthium strumarium: absolute configuration of xanthanol, isoxanthanol and their C-4 epimers. Phytochemistry. 1993; 34 1569-76
- 10 Bohlmann F, Mahanta P K, Jakupovic J, Rastogi R C, Natu A A. New sesquiterpene lactones from Inula species. Phytochemistry. 1978; 17 1165-72
- 11 Hsieh P W, Hwang T L, Wu C C, Chang F R, Wang T W, Wu Y C. The evaluation of 2,8-substituted benzoxazinone analogues as anti-inflammatory and anti-platelet aggregation agents. Biol Med Chem Lett. 2005; 15 2786-9
Prof. Dr. Yang-Chang Wu
Graduate Institute of Natural Products
Kaohsiung Medical University
Kaohsiung 807
Taiwan
Phone: +886-7-312-1101 ext. 2197
Fax: +886-7-311-4773
Email: yachwu@kmu.edu.tw
Prof. Dr. Fang-Rong Chang
Graduate Institute of Natural Products
Kaohsiung Medical University
Kaohsiung 807
Taiwan
R.O.C.
Phone: +886-7-312-1101 ext. 2197
Fax: +886-7-311-4773
Email: aaronfrc@kmu.edu.tw