Structural elucidation and total assignment of the ¹H and ¹³C NMR spectra of new chalcone dimers

Abstract

Conventional 1D NMR methods and 2D shift-correlated NMR experiments (COSY, HMQC, HMBC) were used for the structural elucidation and 1 H and 13 C chemical shifts assignments of four new types of chalcone dimers isolated from Myracrodruon urundeuva.

Gastroprotective and anti-inflammatory activities integrated to chemical composition of Myracrodruon urundeuva Allemão - A conservationist proposal for the species

“…These studies demonstrated that the cultivated species (shoots of height 40 cm) maintains its genetic characteristics regarding the pharmacological activity and produces qualitatively the same pharmacologically active constituents of the inner bark, the dimeric chalcones urundeuvines A, B, and C ( Fig. 1) (Bandeira et al, 2003) and tannins (Souza et al, 2007).…”

“…The dimeric chalcones urundeuvines A (26), B (31) and C (23) were observed at RT 6.12, 6.74 and 5.84 min in the UPLC-MS chromatogram of the inner bark extract, respectively. These substances were isolated earlier from the M. urundeuva inner bark by Bandeira et al (2003) and employed as analytical standards to confirm their presence. Furthermore, two novel urudeuvine A isomers were identified in the inner bark, with their peaks were observed at different RTs (6.29 and 6.62 min).…”

“…1. Chemical structures of dimeric chalcones isolated from M. urundeuva Allemão -Urundeuvines A, B and C. Source: Bandeira et al, 2003. diameter) at 40°C. The sample (5.0 µL) was eluted with a mobile phase composed of water (A) and acetonitrile (B), both acidified with 0.1% of formic acid, with the following elution gradient: 2-95% of B (0-15 min), 100% of B (15.1-17 min), and equilibrating with 2% of B (17.1-19.1 min) at a flow rate of 0.4 mL min −1 .…”

“…Furthermore, the compounds were assigned by comparison with authentic standards (when available) and public MS database (ChemSpider, PubChem, and MassBank and KNapsack). Urundeuvine standards were previously isolated by Bandeira et al (2003). Swiss albino mice (20-25 g) from the experimental animal facility at the University of Fortaleza (UNIFOR) were kept in a controlled environment (circadian cycle, 22°C) with free access to water and standard pellet diet (Purina, São Paulo, Brazil).…”

A New C-Glucosylflavone from Sorindeia juglandifolia

“…Earlier chemical reports from the family showed phenolic compounds as major constituents: mangiferin from the root bark of Mangifera; quercetin, myricetin, and apigenin glycosides from the leaves of Rhus spp., robustafl avone from seeds of Rhus , bifl avones and bichalcones from Rhus (Chen and Lin, 1975;Masesane et al, 2000;Mdee et al, 2003), Myracrodruon (Bandeira et al, 2003) and Semecarpus (Rao et al, 1973;Murthy, 1992), fustin and fi setin from heartwood of Rhus spp. , and 2,3,6-trihydroxy benzoic acid and 2,3,6-trihydroxy (methyl) benzoate from Sorindeia (Kamkumo et al, 2012).…”