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Efficient synthesis of lactonic and thionolactoniclignans and evaluation of their anti-oxidant, anti-inflammatory and cytotoxic activities

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Abstract

A short and versatile synthesis of α,β-dibenzyl-γ-butyrolactones has been developed starting from inexpensive materials by applying Stobbe condensation and following the novel reductive cyclisation with sodiumborohydride. Natural products Suchilactone (5a), Kaerophyllin (5b), savinin (5d) and anhydropodorhizol (5f) were prepared in racemic form. New thionolactones (6a–6e) were prepared by treating these lignans with Lawesson’s reagent. For all the prepared compounds the antioxidant, anti-inflammatory (5-lipoxygenase inhibition) and cytotoxic (Brine shrimp lethality test) activities were tested. The compounds 5a, 5b, 5c, 5d, 5e and 5f showed good 5-lipoxygenase inhibition activity. The thiono lignan 6d showed impressive cytotoxic activity.

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References

  • Ayres DC, Loike JD (1990) Lignans: chemical, biological and clinical properties. Cambridge University Press, Cambridge

    Book  Google Scholar 

  • Bella M, Piancatelli G, Pigro MC (1999) 3-Phenylselanyl furan-2(SH)-one: a versatile building block in the synthesis of lignans. a new approach towards 3,4-dibenzyl γ-butyrolactones. Tetrahedron 55:12387–12398

    Article  CAS  Google Scholar 

  • Chung LY (2009) Lipoxygenase inhibiting activity of some Malaysian plants. Pharm Biol 47(12):1142–1148

    Article  Google Scholar 

  • Das B, Padma RS, Srinivas KVNS, Das R (1996) Jatrodien, A lignan from stems of Jatrophagossypifolia. Phytochemistry 41(3):985

    Article  CAS  Google Scholar 

  • Feringa BL, Jansen JFGA, Oeveren AV (1994) Enantioselective synthesis of natural dibenzylbutyrolactone lignans. J Org Chem 59:5999–6007

    Article  Google Scholar 

  • Jae YC, Jisoo P, Pyoung SK, Eun SY, Kyong UB, Myung HP (2001) Savinin, a lignan from pterocarpus santalinus inhibits tumor necrosis factor-α production and T cell proliferation. Biol Pharm Bull 24:167–171

    Article  Google Scholar 

  • Jhonson WS, Daub GH (1951) Stobbe condensation. Org React 6:1

    Google Scholar 

  • Kumada M, Minato A, Tamao A, Suzuki K (1980) Synthesis of a lignan skeleton via nickel-and palladium-phosphine complex catalyzed Grignard coupling reaction of halothiophenes. Tetrahedron Lett 21:4017–4020

    Article  Google Scholar 

  • Meyer (1982) A convenient general bioassay for active plant constituents. Planta Med 45:31–34

    Article  CAS  Google Scholar 

  • Middel O, Woerdenbag HJ, Uden WV, Oeveren A, Johan F, Jansen GA, Feringa BL, Konings AWT, Pras N, Kellogg RM (1995) Synthesis and cytotoxicity of novel lignans. J Med chem 38:2112–2118

    Article  CAS  PubMed  Google Scholar 

  • Moritani Y, Fukushima C, Ukita T, Miyagishima T, Ohmizu H, Iwasaki (1996) Stereoselective synthesis of cis and trans isomers of α-hydroxy-α, β-dibenzyl-γ-butyro lactone lignans: new synthesis of Trachelogenin and Guayadequiol. J Org Chem 61:6922–6930

    Article  CAS  PubMed  Google Scholar 

  • Muhammad S, Hyoung JK, Muhammad SA, Yong SL (2005) An update on bioactive plant lignans. Nat Prod Rep 22:696–716

    Article  Google Scholar 

  • Ozturk T, Ertas E, Mert O (2007) Use of Lawesson’s reagent in organic synthesis. Chem Rev 107:5210–5278

    Article  CAS  PubMed  Google Scholar 

  • Pater Rajesh M, Patel Natver J (2011) In vitro antioxidant activity of coumarin compounds by DPPH, super oxide and nitric oxide free radical scavenging methods. J Adv Pharm Educ Res 1:52–68

    Google Scholar 

  • Robert SW (2003) Different strategies for the chemical synthesis of lignans. Phytochem Rev 2:391–400

    Article  Google Scholar 

  • Tomioka K, Ishiguro T, Koga K (1985) Total synthesis of optically pure antitumor lignan, Bursera. Chem Pharm Bull 33:4333–4337

    Article  CAS  Google Scholar 

  • Xia YM, Bi WH, Zhang YY (2009) Synthesis of dibenzyl butane diol lignans and their anti-HIV, anti-HSV, anti-tumar activities. J Chil Chem Soc 54:428–431

    CAS  Google Scholar 

  • Xia YM, Zhang YY, Wang W, Ding Y, He R (2010) Synthesis and bioactivity of erythro-nordihydro guaiaretic acid, threo-(-)-saurunin and their analogues. J Serb Chem Soc 75:1325

    Article  CAS  Google Scholar 

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Acknowledgments

We express our sincere thanks to Gokaraju Gangaraju (Chairman), Gokaraju Ramaraju (Managing Director) and KiranBhupatiraju (CEO) for their continuous support for our work.

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Authors and Affiliations

  1. Laila Impex R&D Centre, Unit-I, Phase-III, Jawaharautonagar, Vijayawada, Andhra Pradesh, 520007, India

    Trimurtulu Golakoti, Hari Krishna Kancharla & Bharani Meka

  2. Andhra University, Visakhapatnam, Andhra Pradesh, 530003, India

    Y. L. N. Murthy

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  1. Trimurtulu Golakoti
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  2. Hari Krishna Kancharla
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  3. Bharani Meka
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  4. Y. L. N. Murthy
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Correspondence to Trimurtulu Golakoti.

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Golakoti, T., Kancharla, H.K., Meka, B. et al. Efficient synthesis of lactonic and thionolactoniclignans and evaluation of their anti-oxidant, anti-inflammatory and cytotoxic activities. Med Chem Res 25, 2906–2915 (2016). https://doi.org/10.1007/s00044-016-1709-5

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  • DOI: https://doi.org/10.1007/s00044-016-1709-5

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