title: Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation.
abstract: 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.
authors.affiliation: Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea. jthwang@kribb.re.kr.
authors.forename: Joo Tae
authors.initials: JT
authors.lastname: Hwang
authors.affiliation: Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea. yesolkim@kribb.re.kr.
authors.forename: Yesol
authors.initials: Y
authors.lastname: Kim
authors.affiliation: Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea. water815@kribb.re.kr.
authors.forename: Hyun-Jae
authors.initials: HJ
authors.lastname: Jang
authors.affiliation: Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea. ohhm@kribb.re.kr.
authors.forename: Hyun-Mee
authors.initials: HM
authors.lastname: Oh
authors.affiliation: College of Agriculture and Life Sciences, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 300-764, Korea. chlim@cnu.ac.kr.
authors.forename: Chi-Hwan
authors.initials: CH
authors.lastname: Lim
authors.affiliation: Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea. lswdoc@kribb.re.kr.
authors.forename: Seung Woong
authors.initials: SW
authors.lastname: Lee
authors.affiliation: Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea. rho-m@kribb.re.kr.
authors.forename: Mun-Chual
authors.initials: MC
authors.lastname: Rho
mesh_terms: D000577:Amides / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D048049:Extracellular Signal-Regulated MAP Kinases / Q000378:metabolism; D006801:Humans; D015850:Interleukin-6 / Q000378:metabolism* / Q000494:pharmacology; D053614:Janus Kinase 2 / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010766:Phosphorylation / Q000187:drug effects; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology*; D031822:Portulaca / Q000737:chemistry*; D050796:STAT3 Transcription Factor / Q000378:metabolism*
chemical_list: D000577:Amides; D015850:Interleukin-6; D010936:Plant Extracts; D050796:STAT3 Transcription Factor; D053614:Janus Kinase 2; D048049:Extracellular Signal-Regulated MAP Kinases
keywords: IL-6; Portulaca oleaceae L; STAT3; conversion study; feruloyl amides