Guaianolide sesquiterpene lactones and aporphine alkaloids from the stem bark of Guatteria friesiana

Emmanoel V Costa; Liviane N Soares; Maria L B Pinheiro; Beatriz H L N S Maia; Francisco A Marques; Andersson Barison; Jackson R G S Almeida; Iran L Sousa; Renan S Galaverna; Gabriel Heerdt; Nelson H Morgon; Leonard D R Acho; Emerson S Lima; Felipe M A da Silva; Hector H F Koolen

doi:10.1016/j.phytochem.2017.10.003

Guaianolide sesquiterpene lactones and aporphine alkaloids from the stem bark of Guatteria friesiana

Phytochemistry. 2018 Jan:145:18-25. doi: 10.1016/j.phytochem.2017.10.003. Epub 2017 Oct 20.

Authors

Affiliations

¹ Department of Chemistry, Federal University of Amazonas - UFAM, 69080-900, Manaus, AM, Brazil. Electronic address: emmanoelvc@gmail.com.
² Department of Chemistry, Federal University of Amazonas - UFAM, 69080-900, Manaus, AM, Brazil.
³ Department of Chemistry, Federal University of Paraná - UFPR, 80060-000, Curitiba, PR, Brazil.
⁴ Center for Study and Research of Medicinal Plants, Federal University of Vale do São Francisco - UNIVASF, 56304-205, Petrolina, PE, Brazil.
⁵ Institute of Chemistry, University of Campinas - UNICAMP, 13083-970, Campinas, SP, Brazil.
⁶ Faculty of Pharmacy, Federal University of Amazonas - UFAM, 69077-000, Manaus, AM, Brazil.
⁷ Metabolomics and Mass Spectrometry Research Group, Amazonas State University - UEA, 690065-130, Manaus, AM, Brazil.

PMID: 29059536
DOI: 10.1016/j.phytochem.2017.10.003

Abstract

Three guaianolide sesquiterpenes, denoted guatterfriesols A-C, and four aporphine alkaloid derivatives were isolated from the stem bark of the Amazonian plant Guatteria friesiana. Thus far, sesquiterpene lactones have not been described in Annonaceae. Structures of the previously undescribed compounds were established by using 1D and 2D NMR spectroscopy in combination with MS. The absolute stereochemistry was assigned via NOE NMR experiments, ECD spectroscopy, and theoretical calculations using the TDDFT approach. Among the isolated compounds, the alkaloid guatterfriesidine showed anti-glycation activity by inhibiting the formation of advanced glycation end-products (AGEs) through the prevention of oxidation in both BSA/methylglyoxal and BSA/fructose systems.

Keywords: Alkaloids; Annonaceae; Anti-glycation activity; Guaianolides; Guatteria friesiana.

MeSH terms

Aporphines / chemistry
Aporphines / isolation & purification
Aporphines / pharmacology*
Dose-Response Relationship, Drug
Glycation End Products, Advanced / antagonists & inhibitors*
Glycation End Products, Advanced / metabolism
Glycosylation / drug effects
Guatteria / chemistry*
Lactones / chemistry
Lactones / isolation & purification
Lactones / pharmacology*
Molecular Structure
Plant Bark / chemistry
Plant Stems / chemistry
Quantum Theory
Sesquiterpenes, Guaiane / chemistry
Sesquiterpenes, Guaiane / isolation & purification
Sesquiterpenes, Guaiane / pharmacology*
Structure-Activity Relationship

Substances

Aporphines
Glycation End Products, Advanced
Lactones
Sesquiterpenes, Guaiane