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Planta Med 2016; 82(08): 729-733
DOI: 10.1055/s-0042-102539
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Cytotoxic Tigliane Diterpenoids from Croton caudatus

Ying-Ying Chen   *
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
2   University of Chinese Academy of Science, Beijing, Peopleʼs Republic of China
,
Kun-Xian Yang   *
3   First People Hospital of Yunnan Province, Kunming, Peopleʼs Republic of China
,
Xing-Wei Yang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
,
Afsar Khan
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
4   Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, Pakistan
,
Lu Liu
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
2   University of Chinese Academy of Science, Beijing, Peopleʼs Republic of China
,
Bei Wang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
2   University of Chinese Academy of Science, Beijing, Peopleʼs Republic of China
,
Yun-Li Zhao
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
,
Ya-Ping Liu
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
,
Yan Li
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
,
Xiao-Dong Luo
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 11 September 2015
revised 06 January 2016

accepted 29 January 2016

Publication Date:
22 March 2016 (online)

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Abstract

Three new tigliane-type diterpenoids were isolated from the methanolic extract of the twigs and leaves of Croton caudatus, trivially named crotusins A–C (1–3). The structures of compounds 1–3 were elucidated on the basis of extensive spectral methods. These new compounds were highly oxygenated and heavily substituted. Cytotoxic activity against five human tumor cell lines was assessed for compounds 1–3 of which compound 3 showed significant inhibitory activity with IC50 values ranging from 0.49 to 4.19 µM against these cells, while crotusins A and B exhibited moderate activity.

Key words

Croton caudatus - Euphorbiaceae - tigliane diterpenoid - cytotoxic activity

* These authors contributed equally to this work.


Supporting Information

 

  • References

  • 1 Salatino A, Salatino MLF, Negri G. Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae). J Braz Chem Soc 2007; 18: 11-33
    CrossrefPubMedSearch in Google Scholar
  • 2 Liu CP, Xu JB, Zhao JX, Xu CH, Dong L, Ding J, Yue JM. Diterpenoids from Croton laui and their cytotoxic and antimicrobial activities. J Nat Prod 2014; 77: 1013-1020
    CrossrefPubMedSearch in Google Scholar
  • 3 Wang GC, Li JG, Li GQ, Xu JJ, Wu X, Ye WC, Li YL. Clerodane diterpenoids from Croton crassifolius . J Nat Prod 2012; 75: 2188-2192
    CrossrefPubMedSearch in Google Scholar
  • 4 Merrit AT, Ley SV. Clerodane diterpenoids. Nat Prod Rep 1992; 9: 243-287
    CrossrefPubMedSearch in Google Scholar
  • 5 Ratnayake Bandara BM, Wimalasiri WR. Diterpene alcohols from Croton lacciferus . Phytochemistry 1988; 27: 225-226
    CrossrefPubMedSearch in Google Scholar
  • 6 Zhang XL, Wang L, Li F, Yu K, Wang MK. Cytotoxic phorbol esters of Croton tiglium . J Nat Prod 2013; 76: 858-864
    CrossrefPubMedSearch in Google Scholar
  • 7 Hayes PY, Chow S, Somerville MJ, Fletcher MT, Voss JJD. Daphnane- and tigliane-type diterpenoid esters and orthoester from Pimela elongate . J Nat Prod 2010; 73: 1907-1913
    CrossrefPubMedSearch in Google Scholar
  • 8 Pan LL, Fang PL, Zhang XJ, Ni W, Li L, Yang LM, Chen CX, Zheng YT, Li CT, Hao XJ, Liu HY. Tigliane-type diterpenoid glycosides from Euphorbia fischeriana . J Nat Prod 2011; 74: 1508-1512
    CrossrefPubMedSearch in Google Scholar
  • 9 Bourjot M, Delang L, Nguyen VH, Neyts J, Gueritte F, Leyssen P, Litaudon M. Prostratin and 12-o-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication. J Nat Prod 2012; 75: 2183-2187
    CrossrefPubMedSearch in Google Scholar
  • 10 Van Duuren BL, Orris L. The tumor-enhancing principles of Croton tiglium L. Cancer Res 1965; 25: 1871-1875
    PubMedSearch in Google Scholar
  • 11 Hecker E, Kubinyi H, Szczepanski CV, Härle E, Bresch H. [Phorbol, a new tetracyclic diterpene from croton oil]. Tetrahedron Lett 1965; 6: 1837-1842
    CrossrefPubMedSearch in Google Scholar
  • 12 Neeman M, Simmons OD. Carbon-13 nuclear magnetic resonance spectroscopy of phorbol. Can J Chem 1979; 57: 2071-2072
    CrossrefPubMedSearch in Google Scholar
  • 13 Colburn NH, Gindhart TD, Hegamyer GA, Blumberg PM, Delclos KB, Magun BE, Lockyer J. Phorbol diester and epidermal growth factor receptors in 12-O-tetradecanoylphorbol 13-acetate-resistant and -sensitive mouse epidermal cells. Cancer Res 1982; 42: 3093-3097
    PubMedSearch in Google Scholar
  • 14 zur Hausen H, OʼNeill FJ, Freese UK, Hecker E. Persisting oncogenic herpes virus induced by the tumor promoter TPA. Nature 1978; 272: 373-375
    CrossrefPubMedSearch in Google Scholar
  • 15 Brune K, Kalin H, Schmidt R, Hecker E. Inflammatory, tumor initiating and promoting activities of polycyclic aromatic hydrocarbons and diterpene esters in mouse skin as compared with their prostaglandin releasing potency in vitro . Cancer Lett 1978; 4: 333-342
    CrossrefPubMedSearch in Google Scholar
  • 16 Korin YD, Brooks DG, Brown S, Korotzer A, Zack JA. Effects of prostratin on T-cell activation and human immunodeficiency virus latency. J Virol 2002; 76: 8118-8123
    CrossrefPubMedSearch in Google Scholar
  • 17 Bocklandt S, Blumberg PM, Hamer DH. Activation of latent HIV-1 expression by the potent anti-tumor promoter 12-deoxyphorbol 13-phenylacetate. Antivir Res 2003; 59: 89-98
    CrossrefPubMedSearch in Google Scholar
  • 18 Gustafson KR, Cardellina JH, McMahon JB, Gulakowski RJ, Ishitoya J, Szallasi Z, Lewin NE, Blumberg PM, Weislow OS, Beutler JA, Buckheit RW, Cragg GM, Cox PA, Bader JP, Boyd MR. A nonpromoting phorbol from the Samoan medicinal plant Homalanthus nutans inhibits cell killing by HIV-1. J Med Chem 1992; 35: 1978-1986
    CrossrefPubMedSearch in Google Scholar
  • 19 McKerrall SJ, Jørgensen L, Kuttruff CA, Ungeheuer F, Baran PS. Development of a concise synthesis of (+)-ingenol. J Am Chem Soc 2014; 136: 5799-5810
    Search in Google Scholar
  • 20 U.S. Food and Drug Administration. 2012 Novel New Drugs Summary. Washington, DC: FDA; 2013 Available at http://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DrugInnovation/UCM337830.pdf Accessed August 25, 2015
    PubMedSearch in Google Scholar
  • 21 Jiangsu New Medical College. [Dictionary of Traditional Chinese Medicine]. Shanghai: Shanghai Science and Technology Press; 1975: 447-448
    Search in Google Scholar
  • 22 Chatterjee A, Banerjee A, Bohlmann F. Crotocaudin, a rearranged labdane type norditerpene from Croton caudatus Geisel. Tetrahedron 1977; 33: 2407-2411
    CrossrefPubMedSearch in Google Scholar
  • 23 Chatterjee A, Banerjee A, Bohlmann F. Isocrotocaudin, a new norclerodane-type diterpene from Croton caudatus . Phytochemistry 1978; 17: 1777-1779
    CrossrefPubMedSearch in Google Scholar
  • 24 Hecker E, Bartscch H, Bresch H, Gschwendt M, Härle E, Kreibich G. Structure and stereochemistry of the tetracyclic diterpene phorbol from Croton tiglium L. Tetrahedron Lett 1967; 8: 3165-3170
    CrossrefPubMedSearch in Google Scholar
  • 25 Pei YH, Kim JW, Kang HB, Lee HK, Kim CS, Song HH, Chin YW, Oh SR. Tigliane diterpene esters with IFN γ-inducing activity from the leaves of Aleurites fordii . Bioorg Med Chem Lett 2012; 22: 2318-2320
    CrossrefPubMedSearch in Google Scholar
  • 26 Forgo P, Rédei D, Zsanett H, Szabó P, Szabó L, Hohmann J. Unusual tigliane diterpenes from Euphorbia grandicornis . J Nat Prod 2011; 74: 639-643
    CrossrefPubMedSearch in Google Scholar
  • 27 Corlay N, Delang L, Girard-Valenciennes E, Neyts J, Clerc P, Smadja J, Guéritte F, Leyssen P, Litaudon M. Tigliane diterpenes from Croton mauritianus as inhibitors of chikungunya virus replication. Fitoterapia 2014; 97: 87-91
    CrossrefPubMedSearch in Google Scholar
  • 28 Ren FX, Ren FZ, Yang Y, Yu NJ, Zhang Y, Zhao YM. Tigliane diterpene esters from the leaves of Croton tiglium . Helv Chim Acta 2014; 97: 1014-1019
    CrossrefPubMedSearch in Google Scholar
  • 29 Coordinating Research Group for the Structure of Artemisinin. [A new type of sesquiterpene lactone – arteannuin]. Chin Sci Bull 1977; 22: 142
    PubMedSearch in Google Scholar
  • 30 Silbert LS. Peroxides. Part 11. Iodimetric analysis of dialkyl and dicumenyl peroxides. Analyst 1992; 117: 745-749
    CrossrefPubMedSearch in Google Scholar
  • 31 Malich G, Markovic B, Winder C. The sensitivity and specificity of the MTS tetrazolium assay for detecting the in vitro cytotoxicity of 20 chemicals using human cell lines. Toxicology 1997; 124: 179-192
    CrossrefPubMedSearch in Google Scholar
  • 32 Zamoiskii EA. [Evaluation of Reed-Muench method in determination of activity of biological preparations]. Zh Mikrobiol Epidemiol Immunobiol 1956; 27: 77-83
    PubMedSearch in Google Scholar
  • 33 Stanic MA. Simplification of the estimation of the 50 percent endpoints according to the Reed and Muench method. Pathol Microbiol 1963; 26: 298-302
    PubMedSearch in Google Scholar