Constituents from the leaves of Clausena lansium and their anti-inflammatory activity
- 500 Downloads
Five new acyclic amides, clausenalansamides C-G (1–5), clausenaline G (6) and (±)-5-(4-methylphenyl)-γ-valerolactone (7) reported from the natural source for the first time, were characterized from the leaves of Clausena lansium. Their structures were established by spectroscopic and spectrometric methods, and the absolute configurations of new compounds 1–5 were determined by electronic circular dichroism and single-crystal X-ray diffraction analyses. Eighteen compounds were evaluated for their anti-inflammatory activity and only imperatorin (11) and wampetin (12) displayed significant inhibition of fMLP/CB-induced superoxide anion generation with IC50 values of 1.7 ± 0.3 and 6.8 ± 1.1 μM, respectively.
KeywordsClausenalansamide Electronic circular dichroism Single-crystal X-ray diffraction analysis Anti-inflammatory Superoxide anion generation
This study was sponsored by the Ministry of Science and Technology, Taiwan, ROC granted to T.-S. Wu, and supported in part by the Vietnam National Foundation for Science and Technology Development (Nr. 104.01-2010.27), and Chang Gung Memorial Hospital (CMRPD1B0481~3, CMRPD1D0281~3, and BMRP450 to H-L Hwang). We also thank Associate Prof. Dr. Tran Huy Thai (Institute of Ecology and Biological Resources, Vietnamese Academy of Science and Technology, Vietnam) for the identification of the plant materials.
Compliance with ethical standards
Conflict of interest
The authors declare no conflict of interest.
- 1.Huang CC (1959) Preliminary Study on Chinese Rutaceae (3). Acta Phytotax Sin 8:69–124Google Scholar
- 2.Yang MH, Cao YH, Li WX, Yang YQ, Cheng YY, Huang L (1987) Isolation and structural elucidation of clausenamide from the leaves of Clausena lansium (Lour.) Skeels. Acta Pharm Sin B 22:33–40Google Scholar
- 3.Yang MH, Chen YY, Huang L (1987) Studies on the chemical constituents of Clausena lansium (Lour.) Skeels II: The isolation and structural elucidation of neoclausenamide and cycloclausenamide. Acta Chin Sin 45:1170–1174Google Scholar
- 5.Lakshmi V, Raj K, Kapil RS (1998) Chemical constituents of Clausena lansium: Part III. Structure of lansamide-3 and 4. Indian J Chem Sect B Org Chem Incl Med Chem 37B:422–424Google Scholar
- 9.Adebajo AC, Iwalewa EO, Obuotor EM, Ibikunle GF, Omisore NO, Adewunmi CO, Obaparusi OO, Klaes M, Adetogun GE, Schmidt TJ, Verspohl EJ (2009) Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects. J Ethnopharmacol 122:10–19CrossRefPubMedGoogle Scholar
- 13.Yang SC, Chung PJ, Ho CM, Kuo CY, Hung MF, Huang YT, Chang WY, Chang YW, Chan KH, Hwang TL (2013) Propofol inhibits superoxide production, elastase release, and chemotaxis in formyl peptide-activated human neutrophils by blocking formyl peptide receptor 1. J Immunol 190:6511–6519CrossRefPubMedGoogle Scholar
- 15.Scott AI (1964) Interpretation ultraviolet spectra of natural products, 2nd edn. Pergamon Press, New YorkGoogle Scholar
- 16.Maneerat W, Tha-in S, Cheenpracha S, Prawat U, Laphookhieo S (2011) New amides from the seeds of Clausana lansium. J Med Plant Res 5:2812–2815Google Scholar
- 23.Yang MH, Chen YY, Huang L (1991) Studies on the chemical constituents of Clausena lansium (Lour.) Skeels. III. The structural elucidation of homo- and ζ- clausenamide. Chin Chem Lett 2:291–292Google Scholar
- 32.Vasskog T, Andersen JH, Hansen E, Svenson J (2012) Characterization and cytotoxicity studies of the rare 21:4 n-7 acid and other polyunsaturated fatty acids from the marine opisthobranch Scaphander lignarius, isolated using bioassay guided fractionation. Mar Drugs 10:2676–2690CrossRefPubMedPubMedCentralGoogle Scholar
- 41.Chen YR, Yang MH, Liu GT, Huang L (1989) 2,3-Dihydroxy-3-phenyl-N-(2-phenylethyl)- propionic acid amides derivatives thereof. US Patent 04826873Google Scholar