New phenol derivatives from Ligularia stenocephala

Abstract

The C–3 2-methyl-but-2-enoic acid ester of 2-(1-1-acetoxyisopropenyl)-5-acetyl-3,6-dihydroxy-2,3-dihydro-benzofuran (1) and 6-acetyl-7-hydroxy-2-isopropylidene-benzo[1,4]dioxin-3-one (2), together with nine known compounds (3–11) were isolated from the roots of Ligularia stenocephala. Their structures were elucidated by spectroscopic methods (IR, MS, 1H, 13C and 2D NMR).

Anti-Inflammatory Potential of Complex Extracts of Ligularia stenocephala Matsum. & Koidz. and Secale cereale L. Sprout in Chronic Gingivitis: In Vitro Investigation and Randomized Clinical Trial

“…It might be regarded that high concentration of TEES-10 ® facilitates complete resolution of LPS induced inflammation in cellular level (Figure 6). Extracts of L. stenocephala contains phenolic substance represented by flavonoid [13,24]. S. cereale sprout also contains phenolic substance and it has been reported that antioxidant effects increase in proportion to the content of phenolic substance [14].…”

“…Future studies for host modulation against chronic gingivitis can be conducted with those plants. Extracts of L. stenocephala contains phenolic substance represented by flavonoid [13,24]. S. cereale sprout also contains phenolic substance and it has been reported that antioxidant effects increase in proportion to the content of phenolic substance [14].…”

Phytochemicals and biological activities of Ligularia species

“…Compounds 3-7 and 3-8 are norursane-type triterpenoids and were isolated from L. tongolensis 47 . Table 4 4, 6,39,66,80,83,89,[105][106][107][108][109][110][111][112][113][114][115][116][117][118][119][120] . Among these structures, 4-49 and 4-50, 4-51 and 4-52, 4-53 and 4-54 were isolated as racemates from L. stenocephala, which were further comfirmed by the chiral HPLC analysis 120 .…”

Constituents of the leaves and roots of Ligularia stenocephala MATSUM. et KOIDZ.

“…The Et 2 O extract (6.4 g) was subjected to silica gel column chromatography (n-hexane-EtOAc, EtOAc and MeOH) and subsequent preparative HPLC (TSKgel ODS-120 T, MeOH and MeOH-H 2 O) to afford (4) (0.4 mg), (5) (0.1 mg), (6) (0.2 mg), (7) (0.2 mg), (8) (0.2 mg) and (9) (0.3 mg). The structures of 1-9 were identified as (-tetracosahexaen-2-ol [4], neophytadiene [5], 5-acetyl-6-hydroxy-2a-isopropenyl-3b-methoxy-2, 3H-benzofuran [6], 3b-acetoxy-6-acetyl-5-hydroxy2a-isopropenyl-2,3H-benzofuran [7], p-hydroxybenzaldehyde, vanillin, 4-hydroxyacetophenone and 4-hydroxy-3-methoxyacetophenone [8], respectively, by comparison of their spectral data with those in the literature (1)(2)(3)(4)(5) 9) or by direct comparison with respective authentic samples (6-8). Compounds 1 and 2 have already been synthesized [3, 4] but have not been isolated from a natural source before.…”