Skip to main content
SpringerLink
Log in

A New Homoisoflavonoid from Caesalpinia bahamensis

  • Short Communication
  • Published:
Revista Brasileira de Farmacognosia Aims and scope Submit manuscript

Abstract

Homoisoflavonoids constitute a rare subclass of flavonoids restricted to only some plant species, including members of the genus Caesalpinia. This research focused on homoisoflavonoids from Caesalpinia bahamensis Lam., Fabaceae, a medicinal plant used in Cuban traditional medicine and known as “brasilete.” An hydroalcoholic extract was prepared from the stem, followed by liquid-liquid partition and further chromatographic separations, resulting in the isolation and structure elucidation by nuclear magnetic resonance spectroscopy and mass spectrometry of an undescribed 3-(2-hydroxy-4-methoxybenzyl)chromane-4,7-diol, for which the name metasappanin was proposed.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

References

  • Abegaz BM, Kinfe HH (2019) Naturally occurring homoisoflavonoids: phytochemistry, biological activities, and synthesis (part II). Nat Prod Commun 14:1934578X1984581. https://doi.org/10.1177/1934578X19845813

    Article  Google Scholar 

  • Abreu OA, Sánchez I, Barreto G, Campal AC (2017) Poor antimicrobial activity on seven Cuban plants. J Pharm Negative Results 8:11–14

    Article  Google Scholar 

  • Baldim JL, Rosa W, Santos MFC, Chagas-Paula DA, Lago JHG, Soares MG (2017) Homoisoflavonoids from Caesalpinia spp.: a closer look at chemical and biological aspects. In: Justino G (ed) Flavonoids: from biosynthesis to human health, IntechOpen. https://doi.org/10.5772/67723

    Chapter  Google Scholar 

  • Felipe A, Gastón G, Scull R, Herrera Y, Fernández Y (2011) Actividad diurética de extractos acuosos y secos de Caesalpinia bahamensis Lam (brasilete) en ratas Wistar. Rev Colombiana Cien Anim 3:300–308

    Article  Google Scholar 

  • Felipe A, Marrero D, Scull R, Cuéllar A, Gutiérrez YI (2017) Composición química de una fracción apolar del extracto metanólico de la madera de Caesalpinia bahamensis Lam. Rev Cien Farm Aliment 3:1–8

    Google Scholar 

  • Felipe A, Hernández I, Gutiérrez YI, Scull R, Carmenate LM, Pieters L, Rodeiro I, Delgado R (2019) Phytochemical study and antioxidant capacity of three fractions from the stem of Caesalpinia bahamensis Lam. J Pharm Pharmacogn Res 7:12–20

    Google Scholar 

  • He DY, Li YP, Tang HB, Luo L, Ma RJ, Wang JH, Wang LQ (2016) Phenolic compounds from the twigs and leaves of tara (Caesalpinia spinosa). J Asian Nat Prod Res 18:334–338. https://doi.org/10.1080/10286020.2015.1096269

    Article  CAS  PubMed  Google Scholar 

  • Namikoshi M, Saitoh T (1987) Homoisoflavonoids and related compounds. IV. Absolute configurations of homoisoflavonoids from Caesalpinia sappan L. Chem Pharm Bull 35:3597–3602. https://doi.org/10.1248/cpb.35.3597

    Article  CAS  Google Scholar 

  • Namikoshi M, Nakata H, Nuno M, Ozawa T, Saitoh T (1987) Homoisoflavonoids and related compounds. III. Phenolic constituents of Caesalpinia japonica Siebold & Zucc. Chem Pharm Bull 35:3568–3575. https://doi.org/10.1248/cpb.35.3568

    Article  CAS  Google Scholar 

  • Pérez CS, Ortiz PJ (2015) Espectroscopía, vol II. Félix Varela, La Habana

    Google Scholar 

  • Roig JT (2012) Plantas medicinales, aromáticas o venenosas de Cuba, 2nd edn. Vol. I. Ciencia y Técnica, Cuba

    Google Scholar 

  • Setzer MC, Schmidt J, Moriarity DM, Setzer WM (2015) A phytopharmaceutical survey of Abaco Island, Bahamas. Am J Essent Oil Nat Prod 3:10–17

    Google Scholar 

  • Zanin JLB, Carvalho BA, Martineli PS, Santos MH, Lago JHG, Sartorelli P, Viegas C, Soares MG (2012) The genus Caesalpinia L. (Caesalpiniaceae): phytochemical and pharmacological characteristics. Molecules 17:7887–7902. https://doi.org/10.3390/molecules17077887

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhao H, Wang X, Li W, Koike K, Bai H (2014) A new minor homoisoflavonoid from Caesalpinia sappan. Nat Prod Res 28:102–105. https://doi.org/10.1080/14786419.2013.847439

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This work was supported by Vlaamse Interuniversitaire Raad - Universitaire Ontwikkelingssamenwerking (VLIR-UOS) Project No. ZEIN2016PR418 – 75155 between the University of Antwerp (Belgium) and the University of Havana (Cuba).

Author information

Authors and Affiliations

  1. Departamento de Farmacia, Instituto de Farmacia y Alimentos, Universidad de la Habana, Havana, Cuba

    Alejandro Felipe González, Yamilet I. Gutiérrez Gaitén & Ramón Scull Lizama

  2. Natural Products & Food Research and Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium

    Kenn Foubert & Luc Pieters

  3. Centro de Investigaciones y Evaluaciones Biológicas, Instituto de Farmacia y Alimentos, Universidad de la Habana, Havana, Cuba

    René Delgado Hernández

  4. Facultad de Ciencias Exactas, Naturales y Agrarias, Universidad de Santander, Santander, Colombia

    René Delgado Hernández

Authors
  1. Alejandro Felipe González
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yamilet I. Gutiérrez Gaitén
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ramón Scull Lizama
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kenn Foubert
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Luc Pieters
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. René Delgado Hernández
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

AFG: concepts or idea, design, definition of the intellectual content, literature search, experimental studies, data acquisition and analysis, statistical analysis, manuscript preparation, and review; YIGG: literature search, experimental studies, data analysis, manuscript editing, and review; RSL: literature search, experimental studies, data analysis, and manuscript review; KF: design, definition or the intellectual content, experimental studies, data acquisition and analysis, and manuscript review; LP: concepts or idea, design, definition of the intellectual content, manuscript editing and review, and headed the project; RDH: concepts or idea, definition of the intellectual content, manuscript editing and review, and headed the project.

Corresponding author

Correspondence to Luc Pieters.

Ethics declarations

Conflict of Interest

The authors declare that they have no conflict of interest.

Electronic Supplementary Material

ESM 1

(DOCX 385 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Felipe González, A., Gutiérrez Gaitén, Y.I., Scull Lizama, R. et al. A New Homoisoflavonoid from Caesalpinia bahamensis. Rev. Bras. Farmacogn. 30, 733–736 (2020). https://doi.org/10.1007/s43450-020-00108-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s43450-020-00108-3

Keywords

Search

Navigation