New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum

Jih Jung Chen; Yu Hsien Lin; Shiow Hwa Day; Tsong Long Hwang; Ih Sheng Chen

doi:10.1016/j.foodchem.2010.09.069

New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum

Jih Jung Chen^*, Yu Hsien Lin, Shiow Hwa Day, Tsong Long Hwang, Ih Sheng Chen

^*Corresponding author for this work

School of Traditional Chinese Medicine

Research output: Contribution to journal › Journal Article › peer-review

62 Scopus citations

Abstract

Zanthoxylum nitidum is commercially used in healthcare products for the improvement of tooth condition. Its fruit is also used as a spice. Three new benzenoids, (E)-4-(4-hydroxy-3-methylbut-2-enyloxy)benzaldehyde (1), (E)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (2), and (Z)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (3), have been isolated from the stem wood of Z. nitidum, together with 17 known compounds (4-20). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 8-10, 13, 14, 17, and 18 exhibited inhibition (IC₅₀≤7.95μg/ml) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7-9, 13, 14, and 17 inhibited fMLP/CB-induced elastase release with IC₅₀ values ≤7.45μg/ml.

Original language	English
Pages (from-to)	282-287
Number of pages	6
Journal	Food Chemistry
Volume	125
Issue number	2
DOIs	https://doi.org/10.1016/j.foodchem.2010.09.069
State	Published - 15 03 2011

Keywords

Anti-inflammatory activity
Benzenoids
Rutaceae
Structure elucidation
Zanthoxylum nitidum

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10.1016/j.foodchem.2010.09.069

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title = "New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum",

abstract = "Zanthoxylum nitidum is commercially used in healthcare products for the improvement of tooth condition. Its fruit is also used as a spice. Three new benzenoids, (E)-4-(4-hydroxy-3-methylbut-2-enyloxy)benzaldehyde (1), (E)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (2), and (Z)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (3), have been isolated from the stem wood of Z. nitidum, together with 17 known compounds (4-20). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 8-10, 13, 14, 17, and 18 exhibited inhibition (IC50≤7.95μg/ml) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7-9, 13, 14, and 17 inhibited fMLP/CB-induced elastase release with IC50 values ≤7.45μg/ml.",

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AU - Chen, Ih Sheng

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AB - Zanthoxylum nitidum is commercially used in healthcare products for the improvement of tooth condition. Its fruit is also used as a spice. Three new benzenoids, (E)-4-(4-hydroxy-3-methylbut-2-enyloxy)benzaldehyde (1), (E)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (2), and (Z)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (3), have been isolated from the stem wood of Z. nitidum, together with 17 known compounds (4-20). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 8-10, 13, 14, 17, and 18 exhibited inhibition (IC50≤7.95μg/ml) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7-9, 13, 14, and 17 inhibited fMLP/CB-induced elastase release with IC50 values ≤7.45μg/ml.

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New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum

Abstract

Keywords

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