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Wolfberry or Goji berry, the fruit of Lycium barbarum, exhibits health-promoting properties that leads to an extensive study of their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized LC-MS/MS and NMR analysis, nine amide compounds were identified from the fruits. Seven of these compounds were identified in this plant for the first time. The amide compounds with a tyramine moiety were the most abundant. In vitro studies indicated that five HCCA compounds showed inhibitory effect on NO production inuded by lipopolysaccharides with IC50 less than 15.08 μM (trans-N-feruloyl dopamine). These findings suggested that wolfberries demonstrated anti-inflammatory properties.

Two new feruloyl amides, N-cis-hibiscusamide (5) and (7′ S)-N-cis-feruloylnormetanephrine (9), and eight known feruloyl amides were isolated from Portulaca oleracea L. and the geometric conversion of the ten isolated feruloyl amides by UV light was verified. The structures of the feruloyl amides were determined based on spectroscopic data and comparison with literature data. The NMR data revealed that the structures of the isolated compounds showed cis/trans-isomerization under normal laboratory light conditions. Therefore, cis and trans-isomers of feruloyl amides were evaluated for their convertibility and stability by UV light of a wavelength of 254 nm. After 96 h of UV light exposure, 23.2%-35.0% of the cis and trans-isomers were converted to trans-isomers. Long-term stability tests did not show any significant changes. Among all compounds and conversion mixtures collected, compound 6 exhibited the strongest inhibition of IL-6-induced STAT3 activation in Hep3B cells, with an IC50 value of 0.2 μM. This study is the first verification of the conversion rates and an equilibrium ratio of feruloyl amides. These results indicate that this natural material might provide useful information for the treatment of various diseases involving IL-6 and STAT3.

A series of 15 phenolic amides (PAs) have been synthesized (PA1-PA15) and examined in vitro by four different tests: (1) prevention of Cu2+-induced human low-density lipoprotein oxidation, (2) scavenging of stable radicals, (3) anti-inflammatory activity, (4) scavenging of superoxide radicals. We used PA1 and α-tocopherol for an in vivo study. The overall potential of the antioxidant system was significantly enhanced by the PA1 and α-tocopherol supplements as the hepatic TBARS levels were lowered while the hepatic SOD activities and GSH concentration were elevated in PA1 fed rats. Our results support that PA1 may exert antioxidant action through inhibiting superoxide generation. PA1 decreased the level of nitric oxide (NO) production, tumor necrosis factor-alpha (TNF-α) and nuclear factor-kappa B (NF-κB). These results show that PA1 can inhibit lipid peroxidation, enhance the activities of antioxidant enzymes, and decrease the TNF-α/NF-κB level and nitric oxide production. Therefore, it was speculated that PA1 acts through its anti-inflammation capacity.

Further examination of Actinodaphne longifolia has led to the isolation of a new phenolic amide, N-trans-feruloyl 3-methyldopamine, along with N-trans-feruloyl tyramine.The structure of this compound was elucidated by spectroscopic and chemical means.Key Word Index - Actinodaphne longifolia; Lauraceae; N-trans-feruloyl 3-methyldopamine; N-trans-feruloyl tyramine; phenolic amide.

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