Skip to main content
SpringerLink
Log in

Triterpenic and monoterpenic esters from stems of Ichnocarpus frutescens and their drug likeness potential

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

Phytochemical studies of ethanolic extract of stems of Ichnocarpus frutescens resulted in the isolation of tetracyclic triterpenic ester lanosteryl oleate (6), two new monoterpenic esters, menth-1(7)-en-9-olyl dodecanoate (7), and 2-(4-methylcyclohex-3-enyl)propyl dodecanoate (8). Their structures were established on the basis of extensive spectral data analysis and chemical methods. From the literature survey, it was revealed that none of these three compounds have been reported earlier from any other parts of I. fructescens. Using StarDrop, drug metabolism and pharmacokinetic parameters have been studied, while data of toxicological endpoints were generated using Derek Nexus. 7 is metabolically stable as compared to 6 and 8. All three molecules are highly lipophilic so tendency to get distributed in brain and adipose tissue is more. Based on the current knowledge database, Derek Nexus predicted that these molecules are not mutagenic, carcinogenic, genotoxic, hepatotoxic, hERG channel inhibitor, nephrotoxic, neurotoxic but StarDrop found them as probable developmental toxic. So in a word, these phytoconstituents have drug-likeness potential and can be evaluated for possible targets.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  • Aggarwal B, Ali M, Singh V, Singla RK (2010) Isolation & characterization of phytoconstituents from the stems of Ichnocarpus frutescens. Chin J Nat Med 8(6):401–404

    Article  CAS  Google Scholar 

  • Bhaveshkumar Dhorajiya D, Jigarkumar Patel R, Mahesh Malani H, Dholakiya Bharatkumar Z (2012) Plant product (R): roscovitine valuable inhibitor of CDKs as An anti-cancer agent. Der Pharmacia Sinica 3(1):131–143

    Google Scholar 

  • Chattejee A, Pakrashi S (2003) The treatise of Indian medicinal plants, 4th edn. NISCAIR, New Delhi

    Google Scholar 

  • Daniel M, Sabnis SD (1978) Chemotaxonomical studies on Apocyanaceae. Indian J Exp Biol 16:512–513

    CAS  Google Scholar 

  • Deepak Dash K, Veerendra Yeligar C, Siva Nayak S, Gosh Tirtha, Rajalingam D, Sengupta Pinaki, Bhim Maiti C, Rapan Maity K (2007) Evaluation of hepatoprotective and antioxidant activity of Ichnocarpus frutescens (Linn.) R.Br. on paracetamol-induced hepatotoxicity in rats. Trop J Pharm Res 6(3):755–765

    Google Scholar 

  • Dhorajiya B, Malani M, Dholakiya B (2011) Extraction and preservation protocol of anti-cancer agents from Marine World. Chem Sci J CSJ-38 (accepted version):1–25.

  • Hou T, Wang J, Zhang W, Xu X (2007) ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? J Chem Inf Model 47:460–463

    Article  CAS  PubMed  Google Scholar 

  • Khan MSY, Javed K, Khan MH (1995) Chemical constituents of the leaves of Ichnocarpus frutescens R. Br J Chem Soc 72:65–66

    CAS  Google Scholar 

  • Kumarappan CT, Mandal SC (2007) Antitumor activity of polyphenolic extract of Ichnocarpus frutescens. Exp Oncol 29(2):94–101

    CAS  PubMed  Google Scholar 

  • Kumarappan CT, Thilagam E, Subhash Mandal C (2012) Antioxidant activity of polyphenolic extracts of Ichnocarpus frutescens. Saudi J Bio Sci 19:349–355

    Article  CAS  Google Scholar 

  • Lakshmi DKM, Rao EV, Rao DV (1985) Triterpenoid constituents of Ichnocarpus frutescens. Indian Drugs 22(10):552–553

    CAS  Google Scholar 

  • LHASA Ltd. Url: http://www.lhasalimited.org/

  • Malathy NS, Sini S (2009) Antimicrobial activities of Ichnocarpus frutescens (L.) R.Br. and Hemidesmus indicus R.Br. Roots. Anc Sci Life 2(4):13–15

    Google Scholar 

  • Minchona PK, Tandon RN (1980) A new triterpenoid glycoside from the stem of Ichnocarpus frutescens. Phytochemistry 19:2053–2055

    Article  Google Scholar 

  • Optibrium Ltd. Url: http://www.optibrium.com/stardrop/

  • Segall MD, Barber C (2014) Addressing toxicity risk when designing and selecting compounds in early drug discovery. Drug Discov Today. doi:10.1016/j.drudis.2014.01.006

    Google Scholar 

  • Sharma SK, Ali M (1996) New lanostane-type triterpenic acid and 13, 14-seco-steroidal esters from the roots of Artemisia schloria. J Nat Prod 59:181–184

    Article  CAS  Google Scholar 

  • Singh RP, Singh RP (1987) Flavanoids of the flowers of Ichnocarpus frutescens. J Indian Chem Soc 64(11):715–716

    CAS  Google Scholar 

Download references

Acknowledgments

The authors owe their gratitude to Ramesh Group of institutions for providing platform to perform this research work. RK Singla is thankful to Science & Engineering Research Board for providing young scientist fellowship vide project notification SR/FT/LS-149/2011. Authors are thankful to Optibrium Ltd and LHASA Ltd for providing StarDrop and Derek Nexus package, respectively.

Conflict of interest

The authors declare no conflict of interest.

Author information

Authors and Affiliations

  1. Department of Pharmacognosy, HR Institute of Pharmacy, Ghaziabad, Uttar Pradesh, India

    Babita Aggarwal

  2. Division of Biotechnology, Netaji Subhas Institute of Technology, University of Delhi, Azad Hind Fauz Marg, Sector-3, Dwarka, 110078, New Delhi, India

    Rajeev K. Singla

  3. Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Hamdard University, Hamdard Nagar, 110062, New Delhi, India

    Mohd. Ali

  4. Department of Pharmacy, Ram-Eesh Institute of Vocational & Technical Education, 3, Knowledge Park I, Greater Noida, Uttar Pradesh, India

    Vijender Singh

  5. Natural Product Laboratories, SIPBS, University of Strathclyde, 161 Cathedral Street, Glasgow, G4 0RE, Scotland, UK

    John O. Igoli

  6. Faculty of Medicine, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Rohit Gundamaraju & Kah Hwi Kim

Authors
  1. Babita Aggarwal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rajeev K. Singla
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohd. Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Vijender Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. John O. Igoli
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Rohit Gundamaraju
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Kah Hwi Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rajeev K. Singla.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aggarwal, B., Singla, R.K., Ali, M. et al. Triterpenic and monoterpenic esters from stems of Ichnocarpus frutescens and their drug likeness potential. Med Chem Res 24, 1427–1437 (2015). https://doi.org/10.1007/s00044-014-1227-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-014-1227-2

Keywords

Search

Navigation