新木脂素、香豆素木脂素、木脂素衍生物及色烯：来自鹰爪花椒的抗炎成分。

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

作者信息

Chen Jih-Jung, Wang Tzu-Ying, Hwang Tsong-Long

机构信息

Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan, Republic of China.

出版信息

J Nat Prod. 2008 Feb;71(2):212-7. doi: 10.1021/np070594k. Epub 2008 Jan 23.

DOI:10.1021/np070594k

PMID:18211005

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.

摘要

从两面针茎木中分离出8个新化合物，包括4个新的新木脂素，即(7'S,8'S)-荜拔新素(1)、(7'S,8'S)-5-去甲氧基荜拔新素(2)、(7'S,8'S)-5-O-去甲基-4'-O-甲基荜拔新素(3)和(7'S,8'S)-诺可他尔(4)，1个新的香豆素木脂素(7'S,8'S)-4'-O-甲基臭荠辛素D(5)，2个新的木脂素衍生物，即(+)-9'-O-(Z)-阿魏酰基-5,5'-二甲氧基落叶松脂醇(6)和(+)-9'-O-(E)-阿魏酰基-5,5'-二甲氧基落叶松脂醇(7)，以及1个新的色烯，即(E)-3-(2,2-二甲基-2H-色烯-6-基)丙-2-烯醛(8)，同时还分离出18个已知化合物(9 - 26)。通过光谱和质谱分析确定了这些新化合物的结构。(7'S,8'S)-臭荠辛素D(5)、臭荠辛素D(9)、茵芋碱(18)、罗勃碱(19)和异叶茴芹素(23)对人中性粒细胞在甲酰基-L-甲硫氨酰-L-亮氨酰-L-苯丙氨酸/细胞松弛素B(FMLP/CB)刺激下产生超氧阴离子具有抑制作用(IC50≤18.19 μM)。此外，茵芋碱(18)抑制FMLP/CB诱导的弹性蛋白酶释放，IC值为19.15±0.66 μM。