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Synthesis and mosquito larvicidal activity of furanochalcones and furanoflavonoids analogous to karanjin

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Abstract

A series of furanoflavonoids analogous to karanjin have been synthesized starting from resacetophenone. Initially, resacetophenone was reacted with bromoacetaldehyde diethylacetal, and the resultant phenoxy acetal, on cyclization, produced linear, 5-acetyl-6-hydroxybenzofuran (3) and angular, 5-acetyl-4-hydroxybenzofuran (4). The linear and angular benzofuran on Claisen–Schmidt condensation with a series of substituted aryl aldehyde produced initially furanochalcones, which on cyclization in presence of alkaline hydrogen peroxide produced the corresponding furanoflavonoids. Synthesized compounds were assayed for mosquito larvicidal activity against Culex quinquefasciatus strain. The results showed enhanced toxic effect of analogues on mosquito larvae compared to karanjin. Angular furanochalcone with no substituent on the aryl moiety and its corresponding angular furanoflavonoid were found to be the most toxic among the studied compounds. Angular furanochalcones showed better activity than their corresponding linear counterparts. An interesting observation is higher toxicity towards the studied larval strain of precursor angular furanochalcones compared to their corresponding furanoflavonoids in most cases.

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References

  • Ahmed G, Mishra PK, Gupta P, Yadav PP, Tiwari P, Tamrakar AK, Srivastava AK, Maurya R (2006) Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1B inhibitors. Bioorg Med Chem Lett 16:2139–2143

    Article  Google Scholar 

  • Akanksha, Yadav PP, Srivastava AK, Maurya R (2011) Synthesis of analogues of antihyperglycemic lead karanjin. Med Chem Res 20:1465–1472

  • Anuradha V, Srinivas PV, Rao RR, Manjulatha K, Purohit MG, Rao JM (2006) Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L. Bioorg Med Chem 14:6820–6826

    Article  CAS  PubMed  Google Scholar 

  • Bringi NV, Mukerjee SK (1987) Karanja seed (Pongamia glabra) oil. In: Bringi NV (ed) Non-traditional oilseeds and oils in India. Oxford and IBH Publishing Co. Pvt. Ltd, New Delhi, pp 143–166

    Google Scholar 

  • Cheng S-S, Huang C-G, Chen W-J, Kuo Y-H, Chang S-T (2008) Larvicidal activity of tectoquinone isolated from red heartwood-type Cryptomeria japonica against two mosquito species. Bioresour Technol 99:3617–3622

    Article  CAS  PubMed  Google Scholar 

  • Dixit M, Sharon A, Maulik PR, Goel A (2006) A controlled synthesis of nature-mimicking benzofurans and their corresponding dimers. Synlett 10:1497–1502

    Google Scholar 

  • Dixit M, Tripathi BK, Tamrakar AK, Srivastava AK, Kumar B, Goel A (2007) Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors. Bioorg Med Chem 15:727–734

    Article  CAS  PubMed  Google Scholar 

  • Finney DJ (1971) Probit analysis, 3rd edn. Cambridge University Press, London

    Google Scholar 

  • Goel A, Dixit M (2004) Amberlyst 15-catalyzed efficient synthesis of 5-acetyl-4-hydroxy-coumarone and 5-acetyl-6-hydroxy-coumarone: crucial precursors for several naturally occurring furanoflavones. Synlett 11:1990–1994

    Article  Google Scholar 

  • James AA (1992) Mosquito molecular genetics: the hands that feed bite back. Science 257:37–38

    Article  CAS  PubMed  Google Scholar 

  • Majumdar D (2002) Suppression of nitrification and N2O emission by karanjin: a nitrification inhibitor prepared from karanja (Pongamia glabra Vent). Chemosphere 47:845–850

    Article  CAS  PubMed  Google Scholar 

  • Mathur YK, Srivastava JP, Nigam SK (1990) Juvenomimetic effects of karanjin on the larval development of flesh fly, Sarcophaga ruficornis Fabr. (Cyclorrhapha: Diptera). J Entomol Res 14:44–51

    CAS  Google Scholar 

  • Meera B, Kumar S, Kalidhar SB (2003) A review of the chemistry and biological activity of Pongamia pinnata. J Med Aromat Plant Sci 25(25):441–465

    CAS  Google Scholar 

  • Murthy USN, Jamil K (1986) Effect of South Indian vetiver oil (Vetivera zizinoides) L. nash against immature of Culex quinquefasciatus Say (Diptera:Culicidae). Int Pest Control 29:8–9

    Google Scholar 

  • Padmaja B, Kulkaeni NV, Maruthi RG (2007) Effects of karanjin, the seed extract of Pongamia pinata L. (Family: Fabaceae) on the yellow fever mosquito, Aedes aegypti L. (Diptera: Cullicidae). Pestology 31:64–68

  • Prakash O, Kumar R, Prakash V (2008) Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromones. Eur J Med Chem 43:435–440

    Article  CAS  PubMed  Google Scholar 

  • Rao RR, Tiwari AK, Reddy PP, Babu KS, Ali AZ, Madhusudhan K, Rao JM (2009) New furanoflavonoids, intestinal α-glucosidase inhibitory and free radical (DPPH) scavenging, activity from antihyperglycemic root extract of Derris indica (Lam.). Bioorg Med Chem Res 17:5170–5175

    Article  Google Scholar 

  • Rao RR, Tiwari AK, Reddy PP, Babu KS, Suresh GA, Ali AZ, Madhusudhan K, Agawane SB, Badrinarayan P, Sastry GN, Rao JM (2012) Synthesis of antihyperglycemic, α-glucosidase inhibitory and DPPH free radical scavenging furanochalcones. Med Chem Res 21:760–774

    Article  Google Scholar 

  • Satyavani SR, Prasad RBN, Murthy USN, Rao MS, Murthy MM, Kanjilal S (2012) Evaluation of karanjin-rich crude extract from expelled cake of Pongamia glabra for mosquito repellant activity. J Lipid Sci Technol 44:54–56

    CAS  Google Scholar 

  • Shanmugasundaram R, Jeyalakshmi T, Sunil Dutt M, Balakrishna Murthy P (2008) Larvicidal activity of neem and karanja oil cakes against mosquito vectors, Culex quinquefasciatus (Say), Aedes aegypti (L.) and Anopheles stephensi (L.). J Environ Biol 29:43–45

    CAS  PubMed  Google Scholar 

  • Sighamony S, Naidu MB, Osmani Z (1983) Karanja oil and its components as synergists to insecticides. Int Pest Control 25:120–121

    CAS  Google Scholar 

  • Susarla RS, Murthy MM, Rao BVSK, Chakrabarti PP, Prasad RBN, Kanjilal S (2012) A method for isolation of karanjin from the expelled cake of Pongamia glabra. Eur J Lipid Sci Technol 114:1097–1101

    Article  CAS  Google Scholar 

  • Tamrakar AK, Yadav PP, Tiwari P, Maurya R, Srivastava AK (2008) Identification of pongamol and karanjin as lead compounds with antihyperglycemic activity from Pongamia pinnata fruits. J Ethnopharmacol 118:435–439

    Article  CAS  PubMed  Google Scholar 

  • WHO (1996) Report of the WHO informal consultation on the evaluation on the testing of insecticides. CTD/WHO PES/IC/96.1, p. 69

  • Yadav PP, Gupta P, Chaturvedi AK, Shukla PK, Maurya R (2005) Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents. Bioorg Med Chem 13:1497–1505

    Article  CAS  PubMed  Google Scholar 

  • Yang YC, Lee SG, Lee HK, Kim MK, Lee SH (2002) A piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae. J Agric Food Chem 50(50):3765–3767

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

Authors gratefully acknowledge the financial grant received from the Department of Science and Technology, Govt. of India under Technology System Development (TSD) Program.

Conflict of interest

The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, India

    Susarla R. Satyavani, Sanjit Kanjilal & Rachapudi B. N. Prasad

  2. Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India

    Muthineni S. Rao & Upadyayula S. N. Murthy

Authors
  1. Susarla R. Satyavani
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  2. Sanjit Kanjilal
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  3. Muthineni S. Rao
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  4. Rachapudi B. N. Prasad
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  5. Upadyayula S. N. Murthy
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Correspondence to Sanjit Kanjilal.

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Satyavani, S.R., Kanjilal, S., Rao, M.S. et al. Synthesis and mosquito larvicidal activity of furanochalcones and furanoflavonoids analogous to karanjin. Med Chem Res 24, 842–850 (2015). https://doi.org/10.1007/s00044-014-1160-4

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  • DOI: https://doi.org/10.1007/s00044-014-1160-4

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