Structural elucidation of two new chromones isolated from glasswort (Salicornia europaea L.).

Abstract

Twochromones isolated from the methanol extract of glasswort (Salicornia europaea L.) were elucidated to be 7-hydroxy-6-methoxychromoneand 7 O>-/?-D-glucopyranosyl-6-methoxychromone on the basis of chemical and spectral analyses and synthetic studies. These two are natural products hitherto unknown.In a previous paper,1} we have reported that four compounds were isolated from the reddish leaves and stems of glasswort and CompoundsI, II and III were determined to be 2'-hydroxy-6,7-methylenedioxyisoflavone, ( -)-(2S)-2' -hydroxy-6,7-methylenedioxyflavanone and 2/,7-dihydroxy-6-methoxyisoflavone, respectively.

Activity of ethanolic extracts of salt marsh plants from the Lower Saxonian Wadden Sea Coast against microorganisms

“…BHOS~E et al (1999 found significant antifungal activity in Salicornia brachiata. Flavonoid compounds, which have been shown to be responsible for the antimicrobial activity in A. maritima (MITsCHER et al 1972), are also present in S. europaea (ARAKaWA et al 1982;GESLIN & VERBIST 1985;LELLAU & LmBEZEIT 2001). Alkaloids (BoRKOWSKI & DROST 1965) and chromones (CHuI et al 1978;A~q et al 1983) complete the spectrum of secondary metabolites found in glasswort.…”

Salicornia L. (Salicornia pusilla J. Woods, S. ramosissima J. Woods, S. europaea L., S. obscura P.W. Ball & Tutin, S. nitens P.W. Ball & Tutin, S. fragilis P.W. Ball & Tutin and S. dolichostachya Moss)

“…The reddish stems of S. europaea also contain two 2,3‐unsubstituted chromones, identified as 6,7‐methylenedioxychromone and 6,7‐dimethoxychromone, respectively (Chiji et al . 1978; Arakawa et al . 1983).…”

“…1983). Arakawa et al . (1982) determined the structure of two new isoflavones (2′‐hydroxy‐6, 7‐methylenedioxyisoflavone and 2′, 7‐dihydroxy‐6‐methoxyisoflavone) and one flavanone (—)‐(2 S )‐2′‐hydroxy‐6, 7‐methylenedioxyflavanone, from S. europaea in Japan.…”

A new triterpenoid saponin and other saponins from Salicornia europaea

“…Previous researches of chemical constituents of this plant resulted in the isolation of nine flavonoid compounds and four chromone compounds [2][3][4][5]. In the current research, a new triterpenoid saponin, namely 3E,29-dihydroxy-olean-12-en-28-oic acid 28-O-E-D-glucopyranosyl ester, was isolated from Salicornia europaea Linn., together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-E-D-glucopyranoside (2), 3-O-(methyl-E-D-glucuronopyranosiduronoate)-28-O-E-D-glucopyranosyl oleanolate (chikusetsusaponin IVa methyl ester) (3), 3-O-E-D-glucuronopyranosyl oleanolic acid (calenduloside E) (4), and oleanolic acid 3-O-6c-O-methyl-E-D-glucuronopyranoside (calenduloside E 6c-methyl ester) (5).…”

“…Previous researches of chemical constituents of this plant resulted in the isolation of nine flavonoid compounds and four chromone compounds [2][3][4][5]. In the current research, a new triterpenoid saponin, namely 3E,29-dihydroxy-olean-12-en-28-oic acid 28-O-E-D-glucopyranosyl ester, was isolated from Salicornia europaea Linn., together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-E-D-glucopyranoside (2) The 13 C NMR spectrum ( Table 1) displayed signals of one hydroxyl-bearing carbon at G 78.1 (3-EOH) and one hydroxymethylene at G 73.7, which gave a correlation in the HSQC spectrum with a 2H-singlet at G H 3.54.…”