Erythro-Guaiacylglycerol-beta-coniferyl aldehyde ether

Stereoisomeric guaiacylglycerol-beta-coniferyl aldehyde ether induces distinctive apoptosis by downregulation of MEK/ERK pathway in hepatocellular carcinoma cells.[Pubmed:30196208]

Bioorg Chem. 2018 Dec;81:382-388.

Two 8-O-4'-type neolignan epimers Erythro-Guaiacylglycerol-beta-coniferyl aldehyde ether (1) and threo-guaiacylglycerol-beta-coniferyl aldehyde ether (2) were isolated from the stems of Picrasma quassioides. Further chiral separation gave two pairs of enantiomers 1a/1b and 2a/2b. The cytotoxicity assay against hepatocellular carcinoma Hep3B and HepG2 cells was evaluated by MTT assay. The results showed that 1b (IC50=45.56muM) and 2b (IC50=39.02muM) had more cytotoxic effect than its enantiomers 1a (IC50=82.66muM) and 2a (IC50=67.97muM) in Hep3B cells, respectively. Moreover, 1b and 2b could induce more apoptotic cells as well as higher reactive oxygen species (ROS) generation than 1a and 2a at 50muM. In addition, a further study on the phosphoinositide 3-kinase (PI3K)/AKT and mitogen-activated protein kinase kinase (MEK)/extracellular signal-regulated kinase (ERK) signaling pathways was investigated. The results revealed that all compounds had no significant effect on PI3K/AKT pathway, however, 1b and 2b attenuated the relative levels of p-MEK and p-ERK when compared with 1a and 2a. Taken together, the absolute configurations of guaiacylglycerol-beta-coniferyl aldehyde ether had an impact on the inhibitory effect on Hep3B cells. The inactivation of MEK/ERK signaling pathway might contribute to apoptosis induction and ROS generation in 1b- and 2b-treated cells.

Isolation of cytotoxic compounds from the seeds of Crataegus pinnatifida.[Pubmed:23845552]

Chin J Nat Med. 2013 Jul;11(4):411-4.

AIM: To study the chemical constituents and bioactivity of the seeds of Crataegus pinnatifida. METHODS: The chemical constituents were isolated and purified by macroporous adsorptive resin D101, silica gel, and ODS column chromatography, and preparative HPLC. Their structures were elucidated on the basis of spectroscopic methods. In addition, the cytotoxic activities of compounds 1-4 were investigated on OPM2 and RPMI-8226 cells. RESULTS: Four compounds were obtained and their structures were identified as (7S, 8S)-4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3, 5-dimethoxybenzaldehyde (1), (+)-balanophonin (2), Erythro-Guaiacylglycerol-beta-coniferyl aldehyde ether (3), buddlenol A (4). CONCLUSION: Compound 1 is a novel norlignan, while compounds 1-4 exhibited marginal inhibition on the proliferation of OPM2 and RPMI-8226 cells.

Lignans from the fruits of Cornus kousa Burg. and their cytotoxic effects on human cancer cell lines.[Pubmed:17489353]

Arch Pharm Res. 2007 Apr;30(4):402-7.

The fruits of Cornus kousa Burg. were extracted with 80% aqueous MeOH, and the concentrated extract partitioned with EtOAc, n-BuOH and H2O. Six lignans were isolated from the EtOAc fraction through repeated silica gel, ODS and Sephadex LH-20 column chromatographies. From the physico-chemical data, including NMR, MS and IR, the chemical structures of the compounds were determined to be (+)-pinoresinol (1), (-)-balanophonin (2), (+)-laricresinol (3), Erythro-Guaiacylglycerol-beta-coniferyl aldehyde ether (4), threo-guaiacylglycerol-beta-coniferyl aldehyde ether (5) and dihydrodehydrodiconiferyl alcohol (6), which were isolated for the first time from this plant. Most of these compounds showed cytotoxicity against human colon carcinoma (HCT-116) and human hepatocellular carcinoma (HepG2) cell lines in vitro, with IC50 values ranging from 19.1 to 71.3 microg/mL.