Advertisement

Journal of Natural Medicines

, Volume 65, Issue 2, pp 391–394 | Cite as

Laevigatbenzoate from Croton laevigatus Vahl.

  • Guo-An Zou
  • Hong-Wu Zhang
  • Haji Akber Aisa
  • Jun-Shan Yang
  • Chao-Zhong Peng
  • Zhong-Mei Zou
Note

Abstract

A new trans-clerodane diterpenoid, laevigatbenzoate (1), was isolated from the leaves of Croton laevigatus Vahl. Its structure was established on the basis of spectroscopic analysis, and the absolute configuration was determined by application of the CD excitation chirality method. This compound showed weak cytotoxicity against HeLa cells, with an IC50 value of 45.4 μM.

Keywords

Croton laevigatus Vahl. Euphorbiaceae Diterpenoid Laevigatbenzoate Cytotoxicity 

Notes

Acknowledgments

We gratefully acknowledge financial support from the Major Project of Chinese National Programs for Severe Infectious Diseases (2008ZX10003-006), National Natural Science Foundation of China (Grant No. 30900124), and the National S&T Major Special Project on Major New Drug Innovation (2009ZX09301-003). We also thank the staff of the Analytical Center, Beijing Institute of Microchemistry, China, for the measurements of NMR and mass spectra.

References

  1. 1.
    Jiangsu New Medical College (1975) Dictionary of Chinese materia medica. Shanghai Science & Technology, Shanghai, p 881Google Scholar
  2. 2.
    Zou GA, Ding G, Su ZH, Yang JS, Zhang HW, Peng CZ, Aisa HA, Zou ZM (2010) Lactonecembranoids from Croton laevigatus. J Nat Prod 73:792–795PubMedCrossRefGoogle Scholar
  3. 3.
    Zou GA, Su ZH, Zhang HW, Wang Y, Yang JS, Zou ZM (2010) Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook. Molecules 15:1097–1102PubMedCrossRefGoogle Scholar
  4. 4.
    Spanevello RA, Vila AJ (1994) 7-α-Acetoxyhardwickiic acid: a furanoid clerodane. Phytochemistry 35:537–538CrossRefGoogle Scholar
  5. 5.
    Heymann H, Tezuka Y, Kikuchi T, Supriyatna S (1994) Constituents of Sindora sumatrana MIQ. III. New trans-clerodane diterpenoids from the dried pods. Chem Pharm Bull 42:1202–1207Google Scholar
  6. 6.
    Anis I, Anis E, Ahmed S, Mustafa G, Malik A, Amtul Z, Atta-ur-Rahman (2001) Thrombin inhibitory constituents from Duranta repens. Helv Chim Acta 84:649–655Google Scholar
  7. 7.
    Harada N, Iwabuchi J, Yokota Y, Uda H, Nakanishi K (1981) A chiroptical method for determining the absolute configuration of allylic alcohols. J Am Chem Soc 103:5590–5591CrossRefGoogle Scholar
  8. 8.
    Morita H, Nakayama M, Kojima H, Takeya K, Itokawa H, Schenkel EP, Motidome M (1991) Structures and cytotoxic activity relationship of casearins, new clerodane diterpenes from Casearia sylvestris Sw. Chem Pharm Bull 39:693–697PubMedGoogle Scholar
  9. 9.
    Shen YC, Wang CH, Cheng YB, Wang LT, Guh JH, Chien CT, Khalil AT (2004) New cytotoxic clerodane diterpenoids from the leaves and twigs of Casearia membranacea. J Nat Prod 67:316–321PubMedCrossRefGoogle Scholar
  10. 10.
    Xie HG, Chen H, Cao B, Zhang HW, Zou ZM (2007) Cytotoxic germacranolide sesquiterpene from Inula cappa. Chem Pharm Bull 55:1258–1260PubMedCrossRefGoogle Scholar
  11. 11.
    Dewick PM (2002) The biosynthesis of C-5–C-25 terpenoid compounds. Nat Prod Rep 19:181–222PubMedCrossRefGoogle Scholar
  12. 12.
    Merritt AT, Ley SV (1992) Clerodane diterpenoids. Nat Prod Rep 9:243–287PubMedCrossRefGoogle Scholar
  13. 13.
    Rodriguez AD, Li YX, Dhasmana H (1993) New marine cembrane diterpenoids isolated from the Caribbean gorgonian Eunicea mammosa. J Nat Prod 56:1101–1113CrossRefGoogle Scholar
  14. 14.
    Shigemori H, Shimamoto S, Sekiguchi M, Ohsaki A, Kobayashi J (2002) Echinodolides A and B, new cembrane diterpenoids with an eight-membered lactone ring from the leaves of Echinodorus macrophyllus. J Nat Prod 65:82–84PubMedCrossRefGoogle Scholar
  15. 15.
    Kobayashi J, Sekiguchi M, Shimamoto S, Shigemori H, Ohsaki A (2000) Echinophyllins C–F, new nitrogen-containing clerodane diterpenoids from Echinodorus macrophyllus. J Nat Prod 63:1576–1579PubMedCrossRefGoogle Scholar
  16. 16.
    Garcez FR, Garcez WS, da Silva AFG, Bazzo RD, Resende UM (2004) Terpenoid constituents from leaves of Guarea kunthiana. J Braz Chem Soc 15:767–772CrossRefGoogle Scholar
  17. 17.
    Pudhom K, Vilaivan T, Ngamrojanavanich N, Dechangvipart S, Sommit D, Petsom A, Roengsumran S (2007) Furanocembranoids from the stem bark of Croton oblongifolius. J Nat Prod 70:659–661PubMedCrossRefGoogle Scholar
  18. 18.
    Youngsa-ad W, Ngamrojanavanich N, Mahidol C, Ruchirawat S, Prawat H, Kittakoop P (2007) Diterpenoids from the roots of Croton oblongifolius. Planta Med 73:1491–1494PubMedCrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer 2011

Authors and Affiliations

  • Guo-An Zou
    • 1
    • 2
  • Hong-Wu Zhang
    • 1
  • Haji Akber Aisa
    • 2
  • Jun-Shan Yang
    • 1
  • Chao-Zhong Peng
    • 1
  • Zhong-Mei Zou
    • 1
  1. 1.Institute of Medicinal Plant DevelopmentChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijingPeople’s Republic of China
  2. 2.Xinjiang Technical Institute of Physics and ChemistryChinese Academy of SciencesÜrümqiPeople’s Republic of China

Personalised recommendations