Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis

Hao-Chiun Chang; Shih-Wei Wang; Chin-Yen Chen; Tsong-Long Hwang; Ming-Jen Cheng; Ping-Jyun Sung; Kuang-Wen Liao; Jih-Jung Chen

doi:10.3390/molecules25245911

Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis

Hao-Chiun Chang, Shih-Wei Wang, Chin-Yen Chen, Tsong-Long Hwang, Ming-Jen Cheng, Ping-Jyun Sung, Kuang-Wen Liao, Jih-Jung Chen^*

^*Corresponding author for this work

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

Abstract

Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), and 3 '',4 ''-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4-26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), 3 '',4 ''-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50

Original language	English
Article number	5911
Number of pages	19
Journal	Molecules
Volume	25
Issue number	24
DOIs	https://doi.org/10.3390/molecules25245911
State	Published - Dec 2020

Keywords

Fraxinus chinensis
Oleaceae
stem bark
secoiridoid
anti-inflammatory activity
CHEMICAL-CONSTITUENTS
SUPEROXIDE
FLOWERS
FRUITS
ROOTS
CELLS

Access to Document

10.3390/molecules25245911

Cite this

@article{52fd1ec163e540aa9d3fcc7df5a52048,

title = "Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis",

abstract = "Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), and 3 '',4 ''-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4-26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), 3 '',4 ''-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50",

keywords = "Fraxinus chinensis, Oleaceae, stem bark, secoiridoid, anti-inflammatory activity, CHEMICAL-CONSTITUENTS, SUPEROXIDE, FLOWERS, FRUITS, ROOTS, CELLS",

author = "Hao-Chiun Chang and Shih-Wei Wang and Chin-Yen Chen and Tsong-Long Hwang and Ming-Jen Cheng and Ping-Jyun Sung and Kuang-Wen Liao and Jih-Jung Chen",

year = "2020",

month = dec,

doi = "10.3390/molecules25245911",

language = "English",

volume = "25",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "24",

}

TY - JOUR

T1 - Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis

AU - Chang, Hao-Chiun

AU - Wang, Shih-Wei

AU - Chen, Chin-Yen

AU - Hwang, Tsong-Long

AU - Cheng, Ming-Jen

AU - Sung, Ping-Jyun

AU - Liao, Kuang-Wen

AU - Chen, Jih-Jung

PY - 2020/12

Y1 - 2020/12

N2 - Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), and 3 '',4 ''-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4-26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), 3 '',4 ''-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50

AB - Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), and 3 '',4 ''-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4-26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), 3 '',4 ''-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50

KW - Fraxinus chinensis

KW - Oleaceae

KW - stem bark

KW - secoiridoid

KW - anti-inflammatory activity

KW - CHEMICAL-CONSTITUENTS

KW - SUPEROXIDE

KW - FLOWERS

KW - FRUITS

KW - ROOTS

KW - CELLS

U2 - 10.3390/molecules25245911

DO - 10.3390/molecules25245911

M3 - Article

VL - 25

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

M1 - 5911

ER -