Skip to main content
Log in

UV–VIS spectral and GC–MS characterization of Handroanthus serratifolius (Vahl.) Grose (a.k.a. Tabebuia serratifolia (Vahl.) Nichols/Lapacho) heartwood main extractives: a comparison of protocols aimed at a practical evaluation of Lapachol and Dehydro-α-Lapachone content

  • Original
  • Published:
European Journal of Wood and Wood Products Aims and scope Submit manuscript

Abstract

In this work, colorimetric and GC–MS analysis methods of Handroanthus serratifolius (Vahl.) Grose (a.k.a. Tabebuia serratifolia (Vahl.) Nichols) heartwood extracts were applied and compared in order to implement reliable, cheap and affordable industrial routine procedures aimed at the practical quantitative evaluation of the main compounds which characterize the extractives from this wood. Lapachol (2-hydroxy-3-(3-methyl-2-butenyl)-1,4-Naphtalenedione), the characteristic extractive of the Handroanthus/Tabebuia genus which along with Dehydro-α-Lapachone (2,2-dimethyl-2H-Naphtho[2,3-b]pyran-5,10-dione) are the two predominant compounds in the Handroanthus serratifolius heartwood, were quantitatively evaluated. For the first one, comparison between colorimetric and GC–MS analyses (based on internal and external standard) allowed the implementation of a quantitative evaluation protocol of practical relevance. Moreover, in the light of its importance in relation to the colorimetric and mechanical features of Lapacho wood (i.e. influence on gluing), a reliable evaluation of the Lapachol dissociation constant in aqueous environment was achieved, and the data obtained also allowed for ascertaining the two main precipitation mechanisms. Dehydro-α-Lapachone content was evaluated by GC–MS analyses based on the internal and external standard methods.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  • Algranti E, Mendonça EM, Ali SA, Kokron CM, Raile V (2005) Occupational asthma caused by Ipe (Tabebuia ssp.) dust. J Investig Allergol Clin Immunol 15(1):81–83

    PubMed  CAS  Google Scholar 

  • Aucélio RQ, Peréz-Cordovés AI, Xavier Lima JL, Ferreir ABB, Esteva Guas AM, da Silva AR (2013) Determination of lapachol in the presence of other naphthoquinones using 3MPA-CdTe quantum dots fluorescent probe. Spectrochim Acta A 100:155–160

    Article  CAS  Google Scholar 

  • Awang DVC, Kindack D, Dawson BA (1986) Tandem HPLC methods for resolution of Lapachol and related naphthoquinones. J Chromatogr 368:439–443

    Article  CAS  Google Scholar 

  • Bonnet M, Coumans M, Hofinger M, Ramaut JL, Gaspar T (1984) High-performance gas chromatography of 1,4-naphthoquinones from Droseraceae Chromatographia 18(11):621–622

    Article  CAS  Google Scholar 

  • Burnett AR, Thomson RH (1967) Part X. The quinoid constituents of Tabebuia avellanedae (Bignoniaceae). J Chem Soc C:2100–2104

    Google Scholar 

  • Burnett AR, Thomson RH (1968) Part XII. Extractives from Tabebuia chrysantha Nichols and other Bignoniaceae. J Chem Soc C:850–853

    Google Scholar 

  • dos Santos AF, Ferraz PAL, Abreu FC, Chiari E, Goulart MOF, Sant’Ana AEG (2001) Molluscicidal and trypanocidal activities of lapachol derivatives. Planta Med 67(1):92–93

    Article  PubMed  CAS  Google Scholar 

  • Epifano F, Genovese S, Fiorito S, Mathieu V, Kiss R (2014) Lapachol and its congeners as anticancer agents: a review. Phytochem Rev 13:37–49

    Article  Google Scholar 

  • Fernandes-de-Oliveira M (2000) Contribuição ao Conhecimento Químico das Espécies Tabebuia serratifolia Nichols e Tabebuia rosea Bertol (Contribution to the chemical knowledge of the species Tabebuia serratifolia Nichols e Tabebuia rosea Bertol) (In Portuguese) Phd Thesis, Curso de Pós-graduação em Química Orgânica, Universidade Federal do Ceará, Fortaleza, Ceará, Brasil

  • Frihart CR, Hunt CG (2010) Adhesives with wood materials bond formation and performance. In: Wood handbook. Vol. 10, USDA, Madison. pp 1–24

    Google Scholar 

  • Girard M, Ethier J-C, Kindack D, Dawson BA, Awang DVC (1987) Mass spectral characterization of naphthoquinones related to lapachol. J Nat Prod 50(6):1149–1151

    Article  CAS  Google Scholar 

  • Girard M, Kindack D, Dawson BA, Ethier JC, Awang DVC, Gentry AH (1988) Naphthoquinone constituents of Tabebuia spp. J Nat Prod 51(5):1023–1024

    Article  PubMed  CAS  Google Scholar 

  • Gonçalves da Cruz Fonseca S, Carvalho Braga RM, Pereira de Santana D (2003) Lapachol chemistry, pharmacology and assay methods. Rev Bras Farm (Portuguese) 84(1): 9–16

    Google Scholar 

  • Grose SO, Olmstead RG (2007) Taxonomic revisions in the polyphyletic genus Tabebuia s. l. (Bignoniaceae). Syst Bot 32(3):660–670

    Article  Google Scholar 

  • Harborne JP (1998) Phytochemical methods, 3rd edn. Chapman & Hall, Boca Raton

    Google Scholar 

  • Hse CY, Kuo ML (1988) Influence of extractives on wood gluing and finishing-a review. For Prod J 38(1):52–56

    CAS  Google Scholar 

  • Hussain H, Krohn K, Ahmad VU, Miana GA, Green IR (2007) Lapachol: an overview. Arkivoc Vol 2007 Part (ii), 4: 145–171

  • Lemos TLG, Monte FJQ, Santos AKL, Santos AKL, Fonseca AM, Santos HS, Oliveira MF, Costa SMO, Pessoa ODL, Braz-Filho R (2007) Quinones from plants of north-eastern Brazil: structural diversity, chemical transformation, NMR data and biological activities. Nat Prod Res 21(6):529–550

    Article  PubMed  CAS  Google Scholar 

  • Lima NMF, dos Santos AF, Porfírio Z, Goulart MOF, Sant’ Ana AEG (2002) Toxicity of lapachol and isolapachol and their potassium salts against Biomphalaria glabrata, Schistosoma mansoni cercariae, Artemia salina and Tilapia nilotica. Acta Trop 83(1):43–47

    Article  PubMed  CAS  Google Scholar 

  • Maciel Tabosa MA, Souto de Melo EK, Belém Seixas K,, Bastos Leal L (2015) Moura Fittipaldi de Souza Dantas I, Pereira de Santana D. Physicochemical characterization of lapachol. Afr J Pharm Pharmaco 9(5):131–138

    Google Scholar 

  • Maeda M, Murakami M, Takegami T et al (2008) Promotion or suppression of experimental metastasis of B16 melanoma cells after oral administration of lapachol. Toxicol Appl Pharmacol 229:232–238

    Article  PubMed  CAS  Google Scholar 

  • Ossowski T, Goulart MOF, de Abreu FC, SantAna AEG, Miranda PRB, de Oliveira Costa C, Liwo A, Falkowski P, Zarzeczanska D (2008) Determination of the pKa values of some biologically active and inactive hydroxyquinones. J Braz Chem Soc 19(1):175–183. https://doi.org/10.1590/S0103-50532008000100025

    Article  CAS  Google Scholar 

  • Rodrigues de Almeida E, Santos Lucena FR, Vila Nova Soares Silva C, da Silva Costa W-jr, Cavalcanti B, Bosco Lindoso Couto J, de Sousa Filho SDG, Soares da Silva LL, da Mota DL, da Silveira AB, da Passilongo Silva AC (2009) Toxicological assessment of beta-lapachone on organs from pregnant and non-pregnant rats. Phytother Res 23(9):1276–1280

    Article  CAS  Google Scholar 

  • Romagnoli M, Segoloni E, Luna M, Margaritelli A, Gatti M, Santamaria U, Vinciguerra V (2013) Wood color in Lapacho (Tabebuia serratifolia): chemical composition and industrial implications. Wood Sci Technol 47:701–716

    Article  CAS  Google Scholar 

  • Steinert J, Khalaf H, Rimpler M (1995) HPLC separation and determination of naphtho[2,3-b]furan-4,9-diones and related compounds in extracts of Tabebuia avellanedae (Bignoniaceae). J Chromatogr A 693:281–287

    Article  CAS  Google Scholar 

  • Steinert J, Khalaf H, Rimpler M (1996) HPLC separation of some naturally occurring naphthoquinones and anthraquinones. J Chrom A 723:206–209

    Article  CAS  Google Scholar 

  • Subramanian S, Ferreira MMC, Trsic M (1998) A structure-activity relationship studyof lapachol and some derivatives of 1,4-naphthoquinones against carcinosarcoma. Struct Chem 9:47–57

    Article  CAS  Google Scholar 

  • Thomson RH (1987) Naturally occurring quinones, 3rd edn. Chapman & Hall, London

    Google Scholar 

  • Vidal-Tessier AM, Delaveau P, Champion B, Jacquemin H (1988) Lipophilic quinones of Tabebuia serratifolia (Vahl.) Nichols trunk wood. Ann Pharmaceutiques francaises (French) 46(1):55–57

    CAS  Google Scholar 

  • Wang X, Chen Y, Rok Lee Y (2011) Concise synthesis of (±)-rhinacanthin A, dehydro α-lapachone, and β-lapachone, and pyranonaphthoquinone derivatives. Bull Korean Chem Soc 32(1):153–156

    Article  CAS  Google Scholar 

  • Windeisen E, Klassen A, Wegener G (2003) On the chemical characterization of plantation teakwood from Panama. Holz Roh Werkst 61:416–418

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We wish to thank Dr. Moreno Gatti of Margaritelli s.p.a. firm for the kind supply of the wood samples.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Enrico Segoloni.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Segoloni, E., Di Maria, F. UV–VIS spectral and GC–MS characterization of Handroanthus serratifolius (Vahl.) Grose (a.k.a. Tabebuia serratifolia (Vahl.) Nichols/Lapacho) heartwood main extractives: a comparison of protocols aimed at a practical evaluation of Lapachol and Dehydro-α-Lapachone content. Eur. J. Wood Prod. 76, 1547–1561 (2018). https://doi.org/10.1007/s00107-018-1331-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00107-018-1331-y

Navigation