Skip to main content
SpringerLink
Log in

Chemical constituents of the plants of the genus Cleistanthus and their biological activity

  • Original Paper
  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

Chemical examinations of Cleistanthus collinus Roxb., a poisonous tree from India, and Cleistanthus patulus Muell. Arg. have resulted in isolation of a number of arylnaphthalide lignans and their glycosides as well as some furofuranoid lignans. While Cleistanthus gracilis Hook. f. from Thailand afforded an unusual glucoside of 2-β-hydroxy-8-azabicyclo-(5,0,2)-4β, 9β-epoxynona-5,7-diene, C. schlechteri from South Africa was the first reported source of the pimarane diterpenes. Cleistanthin A and cleistanthin B, diphyllin glycosides isolated from C. collinus were reported to exhibit cytotoxicity on several cancer cell lines. Cleistanthin A was found to cause DNA strand breaks and induce apoptosis in cultured cells while cleistanthin B caused G1 arrest and induced apoptosis in mammalian cells.

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
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  • Anjaneyulu ASR, Ramaiah PR, Row LR (1975a) The structure of wodeshiol—the first of a new series of lignans. Tetrahedron Lett 34:2961–2964

    Article  Google Scholar 

  • Anjaneyulu ASR, Ramaiah PR, Row LR (1975b) A new diphyllin glycoside from Cleistanthus collinus. Phytochemistry 14:1875–1876

    Article  CAS  Google Scholar 

  • Anjaneyulu ASR, Ramaiah PR, Row LR (1977) Crystalline constituents of Euphorbiaceae: Part XVI—a new diphyllin glycoside from Cleistanthus collinus Roxb. Indian J Chem Section B:10–11

    Google Scholar 

  • Anjaneyulu ASR, Ramaiah PR, Row LR, Venkateswarlu R, Pelter A, Ward RS (1981) New lignan from the heartwood of Cleistanthus collinus. Tetrahedron 37:3641–3652

    Article  CAS  Google Scholar 

  • Candy HA, Pakshong JM, Pegel KH (1970) Pimarane diterpenes from Cleistanthus schlechteri. J Chem Soc (C):2536–2538

  • Govindachari TR, Sathe SS, Viswanathan N, Pai BR, Srinivasan M (1969) Chemical constituents of Cleistanthus collinus (Roxb.). Tetrahedron 25:2815–2821

    Article  CAS  Google Scholar 

  • Kumar CPP, Pande G, Shanmugam G (1998) Cleistanthin B causes G1 arrest and induces apoptosis in mammalian cells. Apoptosis 3:413–419

    Article  PubMed  CAS  Google Scholar 

  • Lakshmi TG, Srimannaryana G, Subbarao HV (1970) Diphyllin O-glycoside from Cleistanthus collinus bark. Curr Sci 39:395

    CAS  Google Scholar 

  • Meenakshi J, Shanmugam G (2000a) Cleistanthin A, a diphyllin glycoside from Cleistanthus collinus, is cytotoxic to PHA-stimulated (proliferating) human lymphocytes. Drug Dev Res 51:187–190

    Article  CAS  Google Scholar 

  • Meenakshi J, Shanmugam G (2000b) Inhibition of matrix metalloproteinase-9 (MMP-9) activity by cleistanthin A, a diphyllin glycoside from Cleistanthus collinus. Drug Dev Res 50:193–194

    Article  CAS  Google Scholar 

  • McGarry EJ, Pegel KH, Phillips L, Waight ES (1969) Cleistanthol, a novel diterpene from Cleistanthus schlechteri (Euphorbiaceae). Chem Comm 1074

  • McGarry EJ, Pegel KH, Phillips L, Waight ES (1971) The constitution of the aromatic Diterpene cleistanthol. J Chem Soc (C):904–909

  • Pinho P, Naengchomnong W, Kijjoa A, Nazareth N, Silva AMS, Eaton G, Herz W (2006) An unusual glucoside from Cleistanthus gracilis. Phytochemistry 67:1789–1792

    Article  PubMed  CAS  Google Scholar 

  • Prabhakaran C, Kumar P, Panneerselvam N, Rajesh S, Shanmugam G (1996) Cytotoxic and genotoxic effects of cleistanthin B in normal and tumour cells. Mutagenesis 11:553–557

    Article  PubMed  CAS  Google Scholar 

  • Pradheepkumar CP, Shanmugam G (1999) Anticancer potential of cleistanthin A isolated from the tropical plant Cleistanthus collinus. Oncol Res 11:225–232

    PubMed  CAS  Google Scholar 

  • Pradheepkumar CP, Pannerselvam N, Shanmugam G (2000) Cleistanthin A causes DNA strand breaks and induces apoptosis in cultured cells. Mutation Res/Genet Toxicol Environ Mutat 464:185–193

    Article  CAS  Google Scholar 

  • Ramesh C, Ravindranath N, Ram TS, Das B (2003) Arylnaphthalide lignans from Cleistanthus collinus. Chem Pharm Bull 51:1299–1300

    Article  PubMed  CAS  Google Scholar 

  • Sastry KV, Rao V (1983) Isolation and structure elucidation of cleistanthoside A. Planta Med 47:227–229

    CAS  Google Scholar 

  • Sastry KV, Rao EV, Buchanan JG, Sturgeon RJ (1987) Cleistanthoside B, a diphyllin glycoside from Cleistanthus patulus heartwood. Phytochemistry 26:1153–1154

    Article  CAS  Google Scholar 

  • Satayanarayana P, Subrahmanyam P, Rao K (1984) Chemical constituents of Cleistanthus collinus roots. Indian J Pharm Sci 46:95–96

    Google Scholar 

Download references

Acknowledgements

We thank Fundação para a Ciência e Tecnologia (FCT) and CIIMAR (Programa Plurianual) for support.

Author information

Authors and Affiliations

  1. CIIMAR—Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, 4099-003, Porto, Portugal

    Paulo M. M. Pinho & Anake Kijjoa

Authors
  1. Paulo M. M. Pinho
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anake Kijjoa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anake Kijjoa.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pinho, P.M.M., Kijjoa, A. Chemical constituents of the plants of the genus Cleistanthus and their biological activity. Phytochem Rev 6, 175–182 (2007). https://doi.org/10.1007/s11101-006-9027-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-006-9027-z

Keywords

Search

Navigation