Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae

Journal of Natural Products
Jih-Jung ChenTsong-Long Hwang

Abstract

Eight new compounds, including four new neolignans, (7' S,8' S)-bilagrewin ( 1), (7' S,8' S)-5-demethoxybilagrewin ( 2), (7' S,8' S)-5- O-demethyl-4'- O-methylbilagrewin ( 3), and (7' S,8' S)-nocomtal ( 4), a new coumarinolignan, (7' S,8' S)-4'- O-methylcleomiscosin D ( 5), two new lignan derivatives, (+)-9'- O-( Z)-feruloyl-5,5'-dimethoxylariciresinol ( 6) and (+)-9'- O-( E)-feruloyl-5,5'-dimethoxylariciresinol ( 7), and a new chromene, ( E)-3-(2,2-dimethyl-2 H-chromen-6-yl)prop-2-enal ( 8), have been isolated from the stem wood of Zanthoxylum avicennae, together with 18 known compounds ( 9- 26). The structures of these new compounds were determined through spectroscopic and MS analyses. (7' S,8' S)-4'- O-Methylcleomiscosin D ( 5), cleomiscosin D ( 9), skimmianine ( 18), robustine ( 19), and integrifoliolin ( 23) exhibited inhibition (IC 50 < or = 18.19 microM) of superoxide anion generation by human neutrophils in response to formyl- l-methionyl- l-leucyl- l-phenylalanine/cytochalasin B (FMLP/CB). In addition, skimmianine ( 18) inhibited FMLP/CB-induced elastase release with an IC 50 value of 19.15 +/- 0.66 microM.

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Citations

Jan 25, 2013·Inflammation Research : Official Journal of the European Histamine Research Society ... [et Al.]·M RatheeshAntony Helen
Aug 17, 2010·Journal of Natural Medicines·Minpei KurodaYoshihiro Mimaki
Feb 26, 2010·Journal of Asian Natural Products Research·Yan ZhengChifu Brad Huang
Mar 12, 2013·Acta Crystallographica. Section E, Structure Reports Online·Dongsoo Koh
Apr 23, 2010·Chemical & Pharmaceutical Bulletin·Yukiko Matsuo, Yoshihiro Mimaki
Jan 5, 2016·Journal of Asian Natural Products Research·Hong-Bing LiuJian-Min Yue
Sep 19, 2015·International Immunopharmacology·Igor A SchepetkinMark T Quinn
Apr 16, 2016·Journal of Natural Products·Pâmela J Dos S BeirigoVirgínia C da Silva
Mar 24, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aihua HuangChaoquan Luo
Jun 15, 2017·Phytochemistry·Tanize S FernandesAdemir F Morel
Aug 3, 2018·Topics in Current Chemistry·A Sajeli Begum, S Santhosh Kumar
Sep 26, 2009·Natural Product Reports·Jian-Yu PanKun Zou
Nov 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yongtong XiongJunkai Li
Nov 5, 2014·Chemical & Pharmaceutical Bulletin·Ki Hyun KimKang Ro Lee
Jan 19, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiuting LiSheng Lin
Jul 1, 2017·Comprehensive Reviews in Food Science and Food Safety·Eliane de Oliveira Silva, Ronan Batista
Feb 11, 2009·Journal of Natural Products·Jih-Jung ChenIh-Sheng Chen

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