Caffeic acid derivatives and further compounds from Espeletia barclayana Cuatrec. (Asteraceae, Espeletiinae). (February 2017)

• Record Type: Journal Article
• Authors: Padilla-Gonzalez, Guillermo F.; Diazgranados, Mauricio; Ccana-Ccapatinta, Gari; Casoti, Rosana; Da Costa, Fernando B.
• Is Part Of: Biochemical systematics and ecology. Volume 70(2017)
• Page Start: 291
• Page End: 293
• Publication Date: 2017-02
• Subjects: Asteraceae -- Caffeoylquinic acids -- Espeletiinae -- Espeletia barclayana -- Flavonoids; YDDUMTOHNYZQPO-FCXRPNKRSA-N -- CWVRJTMFETXNAD-DUXPYHPUSA-N -- UFCLZKMFXSILNL-FCXRPNKRSA-N -- WEPBGSIAWZTEJR-UHFFFAOYSA-N -- YDDUMTOHNYZQPO-FCXRPNKRSA-N -- REFJWTPEDVJJIY-UHFFFAOYSA-N -- LKXBGSZMRNJAST-UKWZQOBBSA-N; Chemotaxonomy -- Periodicals; Biochemical variation -- Periodicals; Ecology -- Periodicals; Biochemistry -- Periodicals; Ecology -- Periodicals; Chimiotaxinomie -- Périodiques; Variation biochimique -- Périodiques; Écologie -- Périodiques; 578.012
• DOI: 10.1016/j.bse.2016.12.016
• Languages: English
• ISSNs: 0305-1978

Abstract

Abstract: This work describes the isolation of seven (1 –7 ) secondary metabolites from Espeletia barclayana (Asteraceae, Espeletiinae) and their identification by spectroscopic (NMR) and spectrometric (MS) techniques. Ten (8 –17 ) additional compounds were identified based on their retention times, high-resolution mass spectrometry data, and comparison with reference substances or data from literature. The systematic significance of some of the identified substances – the sesquiterpene lactone longipilin acetate, four caffeoylquinic acids and two tri-caffeoylaltraric acids – is discussed with the aim of providing insights into the complex relationships among Espeletiinae taxa and its closest relatives. Five of the isolated metabolites [5- O -( E )-caffeoylquinic acid (1 ), 1, 3-di- O -( E )-caffeoylquinic acid (2 ), 1, 5-di- O -( E )-caffeoylquinic acid (3 ), 3, 4-di- O -( E )-caffeoylquinic acid (4 ) and 3- O -methylquercetin 7- O - β -glucopyranoside (7 )] constitute new reports for the genus Espeletia and for the subtribe Espeletiinae. Chemical data suggest that Espeletiinae might have a closer relationship with Smallanthus than with Ichthyothere, i.e., the two genera suggested to be the sister groups of Espeletiinae based on molecular markers. Graphical abstract: Highlights: Seven secondary metabolites were isolated from E. barclayana leaves. Five metabolites are reported for the first time in a Espeletiinae species. The systematic significance of the identified compounds is discussed.