Skip to main content
SpringerLink
Log in

Anti-inflammatory activity of diterpenes from Croton stellatopilosus on LPS-induced RAW264.7 cells

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

Abstract

An acyclic diterpene (plaunotol; 1) and two furanoditerpenes (plaunolide, 2 and plaunol E, 3), were isolated from Croton stellatopilosus leaves, and assessed for their inhibitory activity on nitric oxide (NO) production by lipopolysaccharide (LPS)-induced RAW264.7 cells. Plaunotol, plaunolide and plaunol E exhibited inhibitory activity with IC50 values of 3.41, 17.09 and 2.79 μM, respectively. Cytotoxic effects were observed at concentrations of ≥100 μM for plaunotol and ≥10 μM for plaunol E. In order to understand the mechanism of this anti-inflammatory activity, transcription profiles of the COX-1, COX-2 and iNOS genes were measured using a quantitative RT-PCR technique. The level of gene expression was expressed as a relative quantitation according to the comparative C T method. The results indicated that plaunotol stimulated the COX-1 and COX-2 genes, and suppressed expression of the iNOS gene. Treatment of cells with plaunolide caused a downregulation of the expressions of the COX-1, COX-2 and iNOS genes. In contrast, plaunol E inhibited the expression of the COX-2, stimulated COX-1 and iNOS expressions. In summary, the present study shows that different diterpenes from C. stellatopilosus leaves exhibit anti-inflammatory activity towards LPS-activated RAW264.7 cells by different mechanisms. Our results provide data to support further investigations into the possibility that these diterpenes could be alternatives to act as anti-inflammatory agents.

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

Similar content being viewed by others

References

  1. Esser HJ, Chayamarit K (2001) Two new species and a new name in Thai Croton (Euphorbiaceae). Thai For Bull 29:51–57

    Google Scholar 

  2. Ponglux D, Wongseripipatana S, Phadungcharoen T, Ruangrungsri N, Likhitwitayawuid K (1987) Medicinal Plants. The First Princess Chulabhorn Science Congress Bangkok, Thailand

    Google Scholar 

  3. Ogiso A, Kitazawa E, Kurabayashi M, Sato A, Takahashi S, Noguchi H, Kuwano H, Kobayashi S, Mishima H (1978) Isolation and structure of antipeptic ulcer diterpene from Thai medicinal plant. Chem Pharm Bull 26(10):3117–3123

    Article  PubMed  CAS  Google Scholar 

  4. Kitazawa E, Ogiso A, Takahashi S, Sato A, Kurabayashi M, Kuwano H, Hata T, Tamura C (1979) Plaunol A and B, new anti-ulcer diterpenelactones from Croton sublyratus. Tetrahedron Lett 13:1117–1120

    Article  Google Scholar 

  5. Kitazawa E, Sato A, Takahashi S, Kuwano H, Ogiso A (1980) Novel diterpenelactones with anti-peptic ulcer activity from Croton sublyratus. Chem Pharm Bull 28(1):227–234

    Article  PubMed  CAS  Google Scholar 

  6. Takahashi S, Kurabayashi M, Kitazawa E, Haruyama H, Ogiso A (1983) Plaunolide, a furanoid diterpene from Croton sublyratus. Phytochemistry 22:302–303

    Article  CAS  Google Scholar 

  7. Kitazawa E, Ogiso A (1981) Two diterpene alcohols from Croton sublyratus. Phytochemistry 20:287–289

    Article  CAS  Google Scholar 

  8. Kitazawa E, Kurabayashi M, Kasuga S, Oda O, Ogiso A (1982) New esters of diterpene alcohol from Croton sublyratus. Annu Rep Sankyo Res Lab 34:39–41

    CAS  Google Scholar 

  9. Ushiyama S, Matsuda K, Asai F, Yamazaki M (1987) Stimulation of prostaglandin production by (2E,6Z,10E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol (plaunotol), a new anti-ulcer drug, in vitro and in vivo. Biochem Pharmacol 36(3):369–375

    Article  PubMed  CAS  Google Scholar 

  10. Shiratori K, Watanabe S, Takeuchi T (1993) Role of endogenous prostaglandins in secretin- and plaunotol-induced inhibition of gastric acid secretion in rat. Am J Gastroenterol 88(1):84–89

    PubMed  CAS  Google Scholar 

  11. Murakami K, Okajima K, Harada N, Isobe H, Liu W, Johno M, Okabe H (1999) Plaunotol prevents indomethacin-induced gastric mucosal injury in rats by inhibiting neutrophil activation. Aliment Pharmacol Ther 13(4):521–530

    Article  PubMed  CAS  Google Scholar 

  12. Takagi A, Koga Y, Aiba Y, Kabir AM, Watanabe S, Ohta-Tada U, Osaki T, Kamiya S, Miwa T (2000) Plaunotol suppresses interleukin-8 secretion induced by Helicobacter pylori: therapeutic effect of plaunotol on H. pylori infection. J Gastroenterol Hepatol 15(4):374–380

    Article  PubMed  CAS  Google Scholar 

  13. Ohta Y, Kamiya Y, Arisawa T, Nakano H (2005) Plaunotol prevents the progression of acute gastric mucosal induced by compound 48/80, a mast cell degranulator, in rats. Pharmacology 74(4):182–192

    Article  PubMed  CAS  Google Scholar 

  14. Makino M, Inomata Y, Ito K, Tabata K (1998) Effect of plaunotol on trinitrobenzene sulfonic acid and acetic acid induced colonic lesions in rats. Nippon Yakurigaku Zasshi 112(2):97–106

    Article  PubMed  CAS  Google Scholar 

  15. Augusto AC, Miguel F, Mendonça S, Pedrazzoli J, Gurgueira SA (2007) Oxidative stress expression status associated to Helicobacter pylori virulence in gastric diseases. Clin Biochem 40:615–622

    Article  PubMed  CAS  Google Scholar 

  16. Fu HY, Yabe Y, Asahi K, Hayashi Y, Murata H, Eguchi H, Tsuji M, Tsuji S, Kawano S (2005) (2E,6Z,10E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol (plaunotol) increases cyclooxygenase-2 expression via nuclear factor κB and cyclic AMP response element in rat gastric epithelial cells. Eur J Pharmacol 524:38–43

    Article  PubMed  CAS  Google Scholar 

  17. Sae-wong C, Tansakul P, Tewtrakul S (2009) Anti-inflammatory mechanism of Kaempferia parviflora in murine macrophage cells (RAW 264.7) and in experimental animals. J Ethnopharmacol 124:576–580

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

We thank Mr. Anan Chaikitwattana from Tipco Foods (Thailand) Public Co., Ltd., for providing Plaunoi leaf powder and Assistant Prof. Dr. Boonchoo Sritularak for his guidance on optical rotation measurement. Grants from the Prince of Songkla University (no. 530220S) and the Graduate School are also acknowledged. We would like to thank Dr. Brian Hodgson for assistance with the English.

Author information

Authors and Affiliations

  1. Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, 90112, Thailand

    Charoenwong Premprasert, Supinya Tewtrakul, Anuchit Plubrukarn & Juraithip Wungsintaweekul

Authors
  1. Charoenwong Premprasert
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Supinya Tewtrakul
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anuchit Plubrukarn
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Juraithip Wungsintaweekul
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Juraithip Wungsintaweekul.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Premprasert, C., Tewtrakul, S., Plubrukarn, A. et al. Anti-inflammatory activity of diterpenes from Croton stellatopilosus on LPS-induced RAW264.7 cells. J Nat Med 67, 174–181 (2013). https://doi.org/10.1007/s11418-012-0668-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-012-0668-5

Keywords

Search

Navigation