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Synthesis 2021; 53(21): 4075-4078
DOI: 10.1055/a-1531-2385
paper

A Practical and Efficient Conversion of Luteolin into Luteoloside

Benedetta Bassetti
a   Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Via S. Agostino n. 1, 62032 Camerino (MC), Italy
,
Roberto Ballini
a   Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Via S. Agostino n. 1, 62032 Camerino (MC), Italy
,
Daniele Ciceri
b   Indena S.p.A., Viale Ortles n. 12, 20139 Milan, Italy
,
Pietro Allegrini
b   Indena S.p.A., Viale Ortles n. 12, 20139 Milan, Italy
,
Alessandro Palmieri  ∗
a   Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Via S. Agostino n. 1, 62032 Camerino (MC), Italy
› Author AffiliationsThis work was supported by the University of Camerino and Indena S.p.a.
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Abstract

A new practical and efficient preparation of the flavonoid luteoloside is reported in an excellent overall yield of 40% via a four-step synthetic approach.

Key words

luteolin - luteoloside - heterocycles - flavonoids - glycosylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1531-2385.
  • Supporting Information


Publication History

Received: 14 May 2021

Accepted after revision: 17 June 2021

Accepted Manuscript online:
17 June 2021

Article published online:
15 July 2021

© 2021. Thieme. All rights reserved

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  • References

    • 1a Seleem D, Pardi V, Murata RM. Arch. Oral Biol. 2017; 76: 76
      CrossrefPubMed
    • 1b Panche AN, Diwan AD, Chandra SR. J. Nutr. Sci. 2016; 5: e47
      CrossrefPubMed
  • 2 Verma AK, Pratap R. Nat. Prod. Rep. 2010; 27: 1571
    CrossrefPubMed
    • 3a Hollman PC. H, Katan MB. Food Chem. Toxicol. 1999; 37: 937
      CrossrefPubMed
    • 3b Cazarolli LH, Zanatta L, Alberton EH, Bonorino Figueiredo MS. R, Folador P, Damazio RG, Pizzolatti MG, Silva FR. M. B. Mini Rev. Med. Chem. 2008; 8: 1429
      CrossrefPubMed
    • 4a Nijveldt RJ, van Nood E, van Hoorn DE, Boelens PG, van Norren K, van Leeuwen PA. Am. J. Clin. Nutr. 2001; 74: 418
      CrossrefPubMed
    • 4b Karak P. Int. J. Pharm. Sci. Res. 2019; 10: 1567
      CrossrefPubMed
  • 5 Imran M, Rauf A, Abu-Izneid T, Nadeem M, Shariati MA, Khan IA, Imran A, Orhan IE, Rizwan M, Atif M, Gondal TA, Mubarak MS. Biomed. Pharmacother. 2019; 112: 108612
    CrossrefPubMed
  • 6 D’Andrea G. Fitoterapia 2015; 106: 256
    CrossrefPubMed
  • 7 Chua LS. J. Ethnopharmacol. 2013; 150: 805
    CrossrefPubMed
  • 8 Hinou J, Harvala C, Philianos S. Ann. Pharm. Fr. 1989; 47: 95
    CrossrefPubMed
  • 9 Villela A, van der Klift EJ. C, Mattheussens ES. G. M, Derksen GC. H, Zuilhof H, van Beek TA. J. Chromatogr. A 2011; 1218: 8544
    CrossrefPubMed
  • 10 Kang O.-H, Choi J.-G, Lee J.-H, Kwon D.-Y. Molecules 2010; 15: 385
    CrossrefPubMed
  • 11 Kim SH, Kumar CN, Kim HJ, Kim DH, Cho J, Jin C, Lee YS. Bioorg. Med. Chem. Lett. 2019; 19: 6009
    CrossrefPubMed
    • 12a Ballini R, Gabrielli S, Palmieri A. Synlett 2009; 965
    • 12b Ballini R, Gabrielli S, Palmieri A. Synlett 2010; 2468
    • 12c Palmieri A, Petrini M. Chem. Rec. 2016; 16: 1353
      CrossrefPubMed
    • 12d Rossi FV, Ballini R, Barboni L, Allegrini P, Palmieri A. Synthesis 2018; 50: 1924
    • 12e Gabrielli S, Chiurchiù E, Palmieri A. Adv. Synth. Catal. 2019; 361: 630
      Crossref
    • 12f Palmieri A. Eur. J. Org. Chem. 2020; 4247
    • 13a Sun D.-Y, Cheng C, Moschke K, Huang J, Fang W.-S. Molecules 2020; 25: 102
    • 13b Wang Q.-Q, Cheng N, Zheng X.-W, Peng S.-M, Zou X.-Q. Bioorg. Med. Chem. 2013; 21: 4301
      CrossrefPubMed
  • 14 Kappe CO, Stadler A, Dallinger D. In Microwaves in Organic and Medicinal Chemistry, 2nd ed., Vol. 52. Mannhold R, Kubinyi H, Folkers G. Wiley-VCH; Weinheim: 2012
    Google Scholar
  • 15 Chatterjee A, Sarkar S, Saha SK. Phytochemistry 1981; 20: 1760
    Crossref
  • 16 Liu J, Chen L, Cai S, Wang Q. Carbohydr. Res. 2012; 357: 41
    CrossrefPubMed
    • 17a Li N.-G, Shi Z.-H, Tang Y.-P, Yang J.-P, Duan J.-A. Beilstein J. Org. Chem. 2009; 5: 60
      PubMed
    • 17b Shi Z.-H, Li N.-G, Tang Y.-P, Li W, Yin L, Yang J.-P, Tang H, Duan J.-A. Eur. J. Med. Chem. 2012; 54: 210
      CrossrefPubMed
    • 17c Xu B, Liang G, Wen Z, Hu Z, Yuan J, Chen H, Zhang L. Heterocycles 2016; 92: 1245
      Crossref
  • 18 Oyama K, Kondo T. Tetrahedron 2004; 60: 2025
    Crossref
  • 19 Zacharia JT, Hayashi M. Carbohydr. Res. 2012; 348: 91
    CrossrefPubMed