Planta Med 2015; 81 - PM_72
DOI: 10.1055/s-0035-1565449

Metabolomic variation in Senecio graveolens (Asteraceae) in altitudinal populations

N Lopez 1, A Booker 2, M Simirgiotis 3, G León 4, S Alfaro-Lira 1, CO Salas 5, J Santander 6, M Heinrich 2, C Echiburú-Chau 1, 7
  • 1Laboratory for Research and Biomedical Innovation (LIIB), Research Center for the Man in the Desert (CIHDE), Arica, Chile
  • 2Centre for Pharmacognosy and Phytotherapy, UCL School of Pharmacy, University of London, London, United Kingdom
  • 3Laboratorio de Productos Naturales, Facultad de Ciencias Básicas, Departamento de Química, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta, Chile
  • 4Departamento de Química, Facultad de Ciencias, Universidad de Tarapacá, Arica, Chile
  • 5Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, 6094411, Santiago, Chile
  • 6Nucleus for Microbiology and Immunity, Faculty of Sciences, Universidad Mayor, 8580745, Santiago, Chile
  • 7Facultad de Ciencias de la Salud, Universidad de Tarapacá, Arica, Chile

S. graveolens Wedd (Chachacoma; Asteraceae) is an altiplanic plant that grows above 3500 masl in Chile, Peru, Argentina and Bolivia, and is highly used by the Aimaras to ameliorate high-altitude sickness. Although the genus Senecio is reported as rich in pyrrolizidine alkaloids, exhibiting several activities, they are not present in S. graveolens.

We have reported the cytotoxic properties of the S. graveolens ethanolic extract and the identification of 4-hydroxy-3-(3-methyl-2-butenyl)acetophenone with antibacterial activity. Here, we used a metabolomic approach to investigate potential chemical differences based on altitude. We also isolated and characterized the activity of a new S. graveolens compound.

Samples were collected from 4116 – 4611 masl (XV region, Chile). Metabolomic profiling was conducted using 1 H NMR spectroscopy with principal component analysis (PCA) and high performance thin layer chromatography (HPTLC). Furthermore, the new S. graveolens compound was isolated by high-speed countercurrent chromatography and its structure elucidated by NMR and mass spectrometry. Compound's cytotoxic activity was evaluated by MTT in MCF7 cells and the antibacterial activities by the minimum inhibitory concentration.

The PCA analysis of the 1 H NMR spectroscopy fingerprints of S. graveolens clustered samples from the same altitude, establishing a relationship between altitude and principal component 1. In concordance, HPTLC analysis revealed a change in the metabolomic pattern with altitude. The new compound isolated from S. graveolens was identified as 2-hydroxy-5-(3-methylbut-2-enyl)acetophenone, an isomer of the acetophenone previously described by us, with cytotoxic activity on MCF-7 cells (IC50 139 µM) but no antibacterial properties. This compound has been described to exert a wide range of biological activities and this is the first time that it is isolated from a natural source.

Acknowledgement: CONICYT Support of International Networking Between Research Centres REDES140002.