Inhibitory Activity against Helicobacter pylori of Isolated Compounds from Pinus koraiensis Siebold et Zucc Leaves

Abstract

A phenol substance was extracted from Pinus koraiensis Siebold et Zucc leaf extracts and its biological efficacy was measured. The highest content of the phenol substance contained in Pinus koraiensis Siebold et Zucc leaves was 13.5 mg/g, which was obtained when it was extracted with 80% ethanol. At a concentration of 200 mg/mL, the phenolic substances extracted with 80% ethanol and water showed antimicrobial activities against Helicobacter pylori, producing clear zones of 10 and 12 mm diameter, respectively. Pinus koraiensis Siebold et Zucc. leaf extracts were separated using a Sephadex LH-20 column and 4 fractions were obtained (fractions A-D). Fractions C and D showed the greatest inhibitory activity against Helicobacter pylori producing 10.1 and 12.3 mm clear zones, respectively. These two fractions were purified using a Sephadex LH-20 and MCI-gel column (H 2 O→100% ethanol). Purified compounds A and B were identified as syringic acid and compound C was identified as p-coumaric acid based on 1 H-nuclear magnetic resonance (NMR), 13 C-NMR, and fast atom bombardment mass spectrometry spectra. When two or more purified compounds were mixed, a synergistic effect of anti-Helicobacter pylori activity was evident. This result indicates that extracts of Pinus koraiensis Siebold et Zucc leaves could be considered a functional food because of their high antimicrobial properties.

HPLC–ESI/MS profiling, phytoconstituent isolation and evaluation of renal function, oxidative stress and inflammation in gentamicin‐induced nephrotoxicity in rats of Ficus spragueana Mildbr. & Burret

“…Fractionation of the hydroalcoholic extract of F. spragueana leaf using a combination of column chromatography on polyamide gel, Sephadex LH‐20 and preparative paper chromatography resulted in the isolation of five phenolic compounds. The isolated compounds were identified as syringic acid ( 1 ) (Jo & Cho, 2016), p‐ coumaric acid ( 2 ) (Jo & Cho, 2016), 3′,5′ O‐ dicaffeoylquinic acid ( 3 ) (Arbiser et al, 2005; Tolonen, Joutsamo, Mattlla, Kämäräinen, & Jalonen, 2002), luteolin‐8‐C‐β‐D glucopyranoside (orientin) ( 4 ) (de Oliveira, Siqueira, Nunes, & Cota, 2013) and 8‐methoxy kaempferol‐3‐ O‐ [ α ‐L‐rhamnopyranosyl (1→2) β‐D‐glucopyranoside] ( 5 ) (Rychlińska & Gudej, 2002), conclusively by comprehensive spectroscopic data analysis and comparison with previous reported data.…”

“…Compound 1 . Syringic acid, obtained as faint yellow powder, 1 H NMR (400 MHz, MeOD): 7.30 (1H, s , H‐2), 7.13 (1H, s , H‐6), 3.63 (3H, s , OCH 3 ) (Jo & Cho, 2016).…”

“…Compound 2 . p‐ Coumaric acid, obtained as faint yellow powder, 1 H NMR (400 MHz, MeOD): 7.61 (1H, d , J = 16, H‐7), 7.35 (2H, d , J = 8, H‐2,6), 6.76 (2H, d , J = 8, H‐3,5), 6.39 (1H, d , J = 16, H‐8) (Jo & Cho, 2016).…”