Biphenyls from Berberis koreana

Abstract

Three new biphenyls, berbekorin A (1), 2'-hydroxy-3,4,5-trimethoxybiphenyl (2), and 4,5-dihydroxy-3-methoxybiphenyl (3), together with 11 known biphenyls (4-14), were isolated from the n-hexane-soluble fraction of the MeOH extract of the trunk of Berberis koreana. The structures of 1-3 were determined by spectroscopic methods, including 1D and 2D NMR analysis. Compound 1 exhibited cytotoxic activity against the SK-MEL-2 skin melanoma cell line, in particular. Moreover, compounds 2, 5, 6, and 14 inhibited NO production in LPS-activated BV-2 cells, a microglial cell line.

Cytotoxic Steroids from the Trunk ofBerberis koreana

“…[1][2][3] As part of our efforts to screen the bioactive constituents of Korean medicinal plants with potential anti-tumor activities, we found that an MeOH extract of the trunk of Berberis koreana exhibited considerable cytotoxic activity against cultured human tumor cell lines in vitro. 4,5) B. koreana (Berberidaceae), one of the endemic Korean plants, is used as a traditional Korean medicine for treating fever, gastroenteritis, sore throats, and conjunctivitis. 6) Previous phytochemical investigations have isolated such alkaloids as benzylisoquinoline and protoberberine derivatives from this plant.…”

“…[7][8][9] Our earlier phytochemical investigation of B. koreana by bioassay-guided purification resulted in the isolation of biphenyls and triterpenoids with cytotoxicity. 4,5) Our continuing search for active constituents from the n-hexane soluble fraction led to the isolation of three steroids, including the new 3-O-fatty acid ester of a steroid, itesmol 3-Opalmitate (1) (Fig. 1A).…”

“…5) This fraction (8 g) was subjected to silica gel (230-400 mesh, 250 g) column chromatography, eluting with n-hexane-EtOAc 12) This fatty acid unit after being esterified with methanol was analyzed by GC-MS as a methyl ester and identified as palmitic acid. The sterol moiety was identified as itesmol on the basis of an analysis of its MS and NMR spectra and by comparing with reported spectroscopic data.…”

4-Coumarate:CoA ligase family members from elicitor-treated Sorbus aucuparia cell cultures

“…The Pyrinae is the only taxon that produces biphenyls and dibenzofurans as pathogen-induced antimicrobial phytoalexins (Kokubun and Harborne, 1995). Some other plant families, such as Fabaceae, Alliaceae, and Berberidaceae, contain related compounds as preformed secondary metabolites (Khan and Shoeb, 1984;Carotenuto et al, 1998;Kim et al, 2009).…”

Enhancement of antimicrobial and antimutagenic activities of Korean barberry (Berberis koreana Palib.) by the combined process of high‐pressure extraction with probiotic fermentation

“…Berberis koreana belonging to a family of Berberidaceae has been used as a medicinal plant for the treatment of fever, conjunctivitis, sour throat, diarrhoea, parasite infections, and trachoma infections 6–8. In recent years, Berberis spp., including B. aristata , B. vulgaris , B. asiatica , B. chitria , B. lyceum , B. heterophylla and B. aetnensis , have been well investigated for their potential health benefits such as antimicrobial, anti‐inflammatory, and anti‐cancer properties 8–17. The compounds leading to pharmacological activities of Berberis spp.…”