Skip to main content
Log in

Sesquiterpenes from Curcuma comosa

  • Natural Medicine Note
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

From the dried rhizomes of Curcuma comosa cultivating in Thailand, 26 known sesquiterpenes were isolated: zederone, zederone epoxide, furanodienone, isofuranodienone, 1(10)Z,4Z-furanodiene-6-one, glechomanolide, dehydrocurdione, neocurdione, curdione, 7α-hydroxyneocurdione, 7β-hydroxycurdione, germacrone-1(10),4-diepoxide, germacrone, 13-hydroxygermacrone, curzerenone, curcolonol, alismol, alismoxide, zedoarondiol, isozedoarondiol, procurcumenol, isoprocurcumenol, aerugidiol, zedoalactone B, curcumenone, and curcumadione. Their structures were elucidated on the basis of physicochemical evidence. Among them, glechomanolide, curzerenone, curcolonol, alismol, alismoxide, and zedoarondiol showed no significant optical activities, so they may be artifact products during the isolation or drying process.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Sodsai A, Piyachaturawat P, Sophasan S, Suksamrarn A, Vongsakul M (2007) Suppression by Curcuma comosa Roxb. of pro-inflammatory cytokine secretion in phorbol-12-myristate-13-acetate stimulated human mononuclear cells. Int Immunopharmacol 7:524–531

    Article  PubMed  CAS  Google Scholar 

  2. Jantaratnotai N, Utaisincharoen P, Piyachaturawat P, Chongthammakun S, Sanvarinda Y (2006) Inhibitory effect of Curcuma comosa on NO production and cytokine expression in LPS-activated microglia. Life Sci 78:571–577

    Article  PubMed  CAS  Google Scholar 

  3. Suksamrarn A, Eiamong S, Piyachaturawat P, Byrne LT (1997) A phloracetophenone glucoside with choleretic activity from Curcuma comosa. Phytochemistry 45:103–105

    Article  Google Scholar 

  4. Yoshikawa M, Morikawa T, Nakano K, Pongpiriyadacha Y, Murakami T, Matsuda H (2002) Characterization of new sweet triterpene saponins from Albizia myriophylla. J Nat Prod 65:1638–1642

    Article  PubMed  CAS  Google Scholar 

  5. Matsuda H, Pongpiriyadacha Y, Morikawa T, Ochi M, Yoshikawa M (2003) Gastroprotective effects of phenylpropanoids from the rhizomers of Alpinia galanga in rats: structural requirements and mode of action. Eur J Pharmacol 471:59–67

    Article  PubMed  CAS  Google Scholar 

  6. Matsuda H, Morikawa T, Managi H, Yoshikawa M (2003) Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-α and IL-4 in RBL-2H3 cells. Bioorg Med Chem Lett 13:3197–3202

    Article  PubMed  CAS  Google Scholar 

  7. Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M (2003) Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis. J Nat Prod 66:1191–1196

    Article  PubMed  CAS  Google Scholar 

  8. Kishi A, Morikawa T, Matsuda H, Yoshikawa M (2003) Structures of new friedelane- and norfriedelane-type triterpenes and polyacylated eudesmane-type sesquiterpene from Salacia chinensis Linn. (S. prinoides DC., Hippocrateaceae) and radical scavenging activities of principal constituents. Chem Pharm Bull 51:1051–1055

    Article  PubMed  CAS  Google Scholar 

  9. Yoshikawa M, Pongpiriyadacha Y, Kishi A, Kageura T, Wang T, Morikawa T, Matsuda H (2003) Biological activities of Salacia chinensis originating in Thailand: the quality evaluation guided by α-glucosidase inhibitory activity. Yakugaku Zasshi 123:871–880

    Article  PubMed  CAS  Google Scholar 

  10. Matsuda H, Tewtrakul S, Morikawa T, Nakamura A, Yoshikawa M (2004) Anti-allergic principles from Thai zedoary: structural requirements of curcuminoids for inhibition of degranulation and effect on the release of TNF-α and IL-4 in RBL-2H3 cells. Bioorg Med Chem 12:5891–5898

    Article  PubMed  CAS  Google Scholar 

  11. Morikawa T, Matsuda H, Yamaguchi I, Pongpiriyadacha Y, Yoshikawa M (2004) New amides and gastroprotective constituents from the fruit of Piper chaba. Planta Med 70:152–159

    Article  PubMed  CAS  Google Scholar 

  12. Matsuda H, Morikawa T, Xu F, Ninomiya K, Yoshikawa M (2004) New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa. Planta Med 70:1201–1209

    Article  PubMed  CAS  Google Scholar 

  13. Matsuda H, Ando S, Morikawa T, Kataoka S, Yoshikawa M (2005) Structure-activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages. Bioorg Med Chem Lett 15:1949–1953

    Article  PubMed  CAS  Google Scholar 

  14. Ando S, Matsuda H, Morikawa T, Yoshikawa M (2005) 1′S-1′-acetoxychavicol acetate as a new type inhibitor of interferon-β production in lipopolysaccharide- activated mouse peritoneal macrophages. Bioorg Med Chem 13:3289–3294

    Article  PubMed  CAS  Google Scholar 

  15. Morikawa T, Xu F, Matsuda H, Yoshikawa M (2006) Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand. Chem Pharm Bull 54:1530–1534

    Article  PubMed  CAS  Google Scholar 

  16. Matsuda H, Yoshida K, Miyagawa K, Asao Y, Takayama S, Nakashima S, Xu F, Yoshikawa M (2007) Rotenoids and flavonoids with anti-invasion of HT1080, anti-proliferation of U937, and differentiation-inducing activity in HL-60 from Erycibe expansa. Bioorg Med Chem 15:1539–1546

    Article  PubMed  CAS  Google Scholar 

  17. Yoshikawa M, Xu F, Morikawa T, Pongpiriyadacha Y, Nakamura S, Asao Y, Kumahara A, Matsuda H (2007) Medicinal flowers. XII. New spirostane-type steroid saponins with antidiabetogenic activity from Borassus flabellifer. Chem Pharm Bull 55:308–316

    Article  PubMed  CAS  Google Scholar 

  18. Matsuda H, Morikawa T, Ninomiya K, Yoshikawa M (2001) Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma. Tetrahedron 57:8443–8453

    Article  CAS  Google Scholar 

  19. Hikino H, Konno C, Agatsuma K, Takemoto T, Horibe I, Tori K, Oeyama M, Takeda K (1975) Sesquiterpenoids. Part XLVII. Structure, configuration, conformation, and thermal rearrangement of furanodienone, isofuranodienone, curzerenone, epicurzerenone, and pyrocurzererenone, sesquiterpenoids of Curcuma zedoaria. J C S, Perkin I:478–484

  20. Brieskorn CH, Noble P (1983) Furanosesquiterpenes from the essential oil of myrrh. Phytochemistry 22:1207–1211

    Article  CAS  Google Scholar 

  21. Yoshikawa M, Matsuda H (2002) Terpenoid constituents of Alismatis Rhizoma—structure, biological activity, and chemical change of terpenoids during processing. J Trad Med 19:119–128

    CAS  Google Scholar 

  22. Hikino H, Takahashi H, Sakurai Y, Takemoto T, Bhacca NS (1966) Structure of zederone. Chem Pharm Bull 14:550–551

    CAS  Google Scholar 

  23. Hano Y, Akiyama A, Nomura T (1997) Stereochemistries and CD spectra of two new sesquiterpenoids from the fresh rhizoma of cultivated Curcuma sp. in Miyakojima island. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 39:511–516

    Google Scholar 

  24. Gao J, Xie J, Iitaka Y, Inayama S (1989) The stereostructure of wenjine and related (1S, 10S), (4S, 5S)-germacrone-1(10), 4-diepoxide isolated from Curcuma wenyujin. Chem Pharm Bull 37:233–236

    CAS  Google Scholar 

  25. Syu W, Shen C, Non M, Ou J, Lee G, Sun C (1998) Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria. J Nat Prod 61:1531–1534

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by the 21st COE Program, Academic Frontier Project, and a Grant-in-Aid for Scientific Research from MEXT (the Ministry of Education, Culture, Sports, Science and Technology of Japan).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Masayuki Yoshikawa.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Qu, Y., Xu, F., Nakamura, S. et al. Sesquiterpenes from Curcuma comosa . J Nat Med 63, 102–104 (2009). https://doi.org/10.1007/s11418-008-0282-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-008-0282-8

Keywords

Navigation