Skip to main content

Advertisement

SpringerLink
Log in

Constituents from the leaves of Clausena lansium and their anti-inflammatory activity

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Huang CC (1959) Preliminary Study on Chinese Rutaceae (3). Acta Phytotax Sin 8:69–124

    Google 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 22:33–40

    CAS  Google 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 45:1170–1174

    CAS  Google Scholar 

  4. Yang MH, Chen YY, Huang L (1988) Three novel cyclic amides from Clausena lansium. Phytochemistry 27:445–450

    Article  CAS  Google 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:422–424

    CAS  Google Scholar 

  6. Ji X, van der Helm D, Lakshmi V, Agarwal SK, Kapil RS (1992) Structure of lansimide 2, a product from Clausena lansium. Acta Crystallogr Sect C Cryst Struct Commun 48:1082–1085

    Article  Google Scholar 

  7. Chokeprasert P, Charles AL, Sue KH, Huang TC (2007) Volatile components of the leaves, fruits and seeds of wampee [Clausena lansium (Lour.) Skeels]. J Food Compos Anal 20:52–56

    Article  CAS  Google Scholar 

  8. Wong KC, Wong SN, Sam TW, Chee SG (1998) Volatile constituents of Clausena lansium (Lour.) Skeels fruit. J Essent Oil Res 10:700–702

    Article  CAS  Google 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 122:10–19

    Article  CAS  PubMed  Google Scholar 

  10. Shen DY, Chao CH, Chan HH, Huang GJ, Hwang TL, Lai CY, Lee KH, Thang TD, Wu TS (2012) Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers. Phytochemistry 82:110–117

    Article  CAS  PubMed  Google Scholar 

  11. Shen DY, Chan YY, Hwang TL, Juang SH, Huang SC, Kuo PC, Thang TD, Lee EJ, Damu AG, Wu TS (2014) Constituents of the roots of Clausena lansium and their potential anti-inflammatory activity. J Nat Prod 77:1215–1223

    Article  CAS  PubMed  Google Scholar 

  12. Shen DY, Nguyen TN, Wu SJ, Shiao YJ, Hung HY, Kuo PC, Kuo DH, Thang TD, Wu TS (2014) γ- and δ-Lactams from the leaves of Clausena lansium. J Nat Prod 78:2521–2530

    Article  Google 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 190:6511–6519

    Article  CAS  PubMed  Google Scholar 

  14. Yu HP, Hsieh PW, Chang YJ, Chung PJ, Kuo LM, Hwang TL (2011) 2-(2-Fluorobenzamido)benzoate ethyl ester (EFB-1) inhibits superoxide production by human neutrophils and attenuates hemorrhagic shock-induced organ dysfunction in rats. Free Radic Biol Med 50:1737–1748

    Article  CAS  PubMed  Google Scholar 

  15. Scott AI (1964) Interpretation ultraviolet spectra of natural products, 2nd edn. Pergamon Press, New York

    Google 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 5:2812–2815

    CAS  Google Scholar 

  17. Song WW, Zeng GZ, Peng WW, Chen KX, Tan NH (2014) Cytotoxic amides and quinolones from Clausena lansium. Helv Chim Acta 97:298–305

    Article  CAS  Google Scholar 

  18. Milner PH, Coates NJ, Gilpin ML, Spear SR, Eggleston DS (1996) SB-204900, a novel oxirane carboxamide from Clausena lansium. J Nat Prod 59:400–402

    Article  CAS  Google Scholar 

  19. Teshima KI, Kaneko T, Ohtani K, Kasai R, Lhieochaiphant S, Picheansoonthon C, Yamasak K (1998) Sulfur-containing glucosides from Clinacanthus nutans. Phytochemistry 48:831–835

    Article  CAS  Google Scholar 

  20. Liu GT, Li WX, Chen YY, Wei HL (1996) Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice. Drug Dev Res 39:174–178

    Article  CAS  Google Scholar 

  21. Sowmithran D, Prasad KJR (1986) Heterocycles 2: synthesis of 1-hydroxycarbazoles and mukonine isomers. Heterocycles 24:711–717

    Article  CAS  Google Scholar 

  22. Wang B, Shen YM, Shi Y (2006) Enantioselective synthesis of γ-aryl-γ-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer−Villiger oxidation. J Org Chem 71:9519–9521

    Article  CAS  PubMed  Google 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 2:291–292

    CAS  Google Scholar 

  24. Yang L, Deng G, Wang DX, Huang ZT, Zhu JP, Wang MX (2007) Highly efficient and stereoselective N-vinylation of oxiranecarboxamides and unprecedented 8- endo-epoxy-arene cyclization: expedient and biomimetic synthesis of some Clausena alkaloids. Org Lett 9:1387–1390

    Article  CAS  PubMed  Google Scholar 

  25. Shen DY, Juang SH, Kuo PC, Huang GJ, Chan YY, Damu AG, Wu TS (2013) Chemical constituents from Andrographis echioides and their anti-inflammatory activity. Int J Mol Sci 14:496–514

    Article  CAS  Google Scholar 

  26. Lin J (1989) Cinnamamide derivatives from Clausena lansium. Phytochemistry 28:621–622

    Article  CAS  Google Scholar 

  27. Maneerat W, Ritthiwigrom T, Cheenpracha S, Laphookhieo S (2012) Carbazole alkaloids and coumarins from Clausena lansium roots. Phytochem Lett 5:26–28

    Article  CAS  Google Scholar 

  28. Kofinas C, Chinou I, Loukis A, Harvala C, Maillard M, Hostettmann K (1998) Flavonoids and bioactive coumarins of Tordilium apulum. Phytochemistry 48:637–641

    Article  CAS  Google Scholar 

  29. Wu TS, Chan YY, Leu YL (1998) Sesquiterpenes from the root and stem of Aristolochia cucurbitafolia. J Nat Prod 61:511–514

    Article  CAS  Google Scholar 

  30. Ariza MR, Larsen TO, Petersen BO, Duus JØ, Barrero AF (2002) Penicillium digitatum metabolites on synthetic media and Citrus fruits. J Agric Food Chem 50:6361–6365

    Article  CAS  PubMed  Google Scholar 

  31. Wu TS, Huang SC, Wu PL, Teng CM (1996) Carbazole alkaloids from Clausena excavata and their biological activity. Phytochemistry 43:133–140

    Article  CAS  PubMed  Google 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 10:2676–2690

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Kuo PC, Yang ML, Hwang TL, Lai YY, Li YC, Thang TD, Wu TS (2013) Anti-inflammatory diterpenoids from Croton tonkinensis. J Nat Prod 76:230–236

    Article  CAS  PubMed  Google Scholar 

  34. Wu TS, Huang SC, Wu PL (1996) Carbazole alkaloids from stem bark of Clausena excavata. Phytochemistry 43:1427–1429

    Article  CAS  Google Scholar 

  35. Hargus JA, Fronczek FR, Vicente MGH, Smith KM (2007) Mono-(L)-aspartylchlorine-6. Photochem Photobiol 83:1006–1015

    Article  CAS  PubMed  Google Scholar 

  36. Cheng HH, Wang HK, Ito J, Bastow KF, Tachibana Y, Nakanishi Y, Xu Z, Luo TY, Lee KH (2001) Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum. J Nat Prod 64:915–919

    Article  CAS  PubMed  Google Scholar 

  37. Wu PL, Lin FW, Wu TS, Kuoh CS, Lee KH, Lee SJ (2004) Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. Chem Pharm Bull 52:345–349

    Article  CAS  PubMed  Google Scholar 

  38. Machida K, Kikuchi M (1996) Norisoprenoids from Viburnum dilatatum. Phytochemistry 41:1333–1336

    Article  CAS  Google Scholar 

  39. Macías FA, Lacret R, Varela RM, Nogueiras C, Molinillo JMG (2008) Bioactive apocarotenoids from Tectona grandis. Phytochemistry 69:2708–2715

    Article  PubMed  Google Scholar 

  40. Adam W, Zhang A (2004) High π-facial selectivity through chelation of magnesium ions in the DMD epoxidation of α, β-unsaturated imides with chiral pyrrolidinone auxiliaries. Eur J Org Chem 2004:147–152

    Article  Google 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 04826873

Download references

Acknowledgments

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.

Author information

Author notes

    Authors and Affiliations

    1. School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan, 701, Taiwan, ROC

      De-Yang Shen, Ping-Chung Kuo & Tian-Shung Wu

    2. Department of Pharmacy, Chia-Nan University of Pharmacy and Science, Tainan, 71710, Taiwan, ROC

      Shiow-Chyn Huang

    3. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, 333, Taiwan, ROC

      Tsong-Long Hwang

    4. Research Center for Industry of Human Ecology, Research Center for Chinese Herbal Medicine, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, 333, Taiwan, ROC

      Tsong-Long Hwang

    5. Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, 333, Taiwan, ROC

      Tsong-Long Hwang

    6. Department of Biotechnology, Southern Taiwan University of Science and Technology, Tainan, 71005, Taiwan

      Yu-Yi Chan

    7. Department of Pharmacy, Tajen University, Pingtung, 90741, Taiwan, ROC

      Po-Chuen Shieh & Tian-Shung Wu

    8. Department of Chemistry, Vinh University, Vinh City, Vietnam

      Nguyen Thi Ngan & Tran Dinh Thang

    Authors
    1. De-Yang Shen
      View author publications

      You can also search for this author in PubMed Google Scholar

    2. Ping-Chung Kuo
      View author publications

      You can also search for this author in PubMed Google Scholar

    3. Shiow-Chyn Huang
      View author publications

      You can also search for this author in PubMed Google Scholar

    4. Tsong-Long Hwang
      View author publications

      You can also search for this author in PubMed Google Scholar

    5. Yu-Yi Chan
      View author publications

      You can also search for this author in PubMed Google Scholar

    6. Po-Chuen Shieh
      View author publications

      You can also search for this author in PubMed Google Scholar

    7. Nguyen Thi Ngan
      View author publications

      You can also search for this author in PubMed Google Scholar

    8. Tran Dinh Thang
      View author publications

      You can also search for this author in PubMed Google Scholar

    9. Tian-Shung Wu
      View author publications

      You can also search for this author in PubMed Google Scholar

    Corresponding author

    Correspondence to Tian-Shung Wu.

    Ethics declarations

    Conflict of interest

    The authors declare no conflict of interest.

    Additional information

    D.-Y. Shen and P.-C. Kuo contributed equally to this work.

    Electronic supplementary material

    Below is the link to the electronic supplementary material.

    Supplementary material 1 (PDF 2175 kb)

    Rights and permissions

    Reprints and permissions

    About this article

    Check for updates. Verify currency and authenticity via CrossMark

    Cite this article

    Shen, DY., Kuo, PC., Huang, SC. et al. Constituents from the leaves of Clausena lansium and their anti-inflammatory activity. J Nat Med 71, 96–104 (2017). https://doi.org/10.1007/s11418-016-1033-x

    Download citation

    • Received:

    • Accepted:

    • Published:

    • Issue Date:

    • DOI: https://doi.org/10.1007/s11418-016-1033-x

    Keywords

    Search

    Navigation