Flavonoid Glucosides from the Hairy Roots of Catharanthus roseus

Four new flavonoid glucosides, 3′,4′-di-O-methylquercetin-7-O-[(4′′→13′′′)-2′′′,6′′′,10′′′,14′′′-tetramethylhexadec-13′′′-ol-14′′′-enyl]-β-d-glucopyranoside (1), 4′-O-methylkaempferol-3-O-[(4′′→13′′′)- 2′′′,6′′′,10′′′,14′′′-tetramethylhexadecan-13′′′-olyl]-β-d-glucopyranoside (2), 3′,4′-di-O-methylb...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2009-04, Vol.72 (4), p.613-620
Main Authors: Chung, Ill-Min, Ahmad, Ateeque, Ali, Mohd, Lee, Oh-Kyu, Kim, Min-Young, Kim, Jung-Hee, Yoon, Do-Young, Peebles, Christie A. M, San, Ka Yiu
Format: Article
Language:English
Subjects:
Animals
anti-inflammatory activity
Biological and medical sciences
Catharanthus - chemistry
Catharanthus roseus
cell lines
chemical structure
cytotoxicity
Dose-Response Relationship, Drug
flavonoids
Flavonoids - chemistry
Flavonoids - isolation & purification
Flavonoids - pharmacology
General pharmacology
glucosides
Glucosides - chemistry
Glucosides - isolation & purification
Glucosides - pharmacology
Humans
isolation
lipopolysaccharides
Lipopolysaccharides - pharmacology
Matrix Metalloproteinase Inhibitors
matrix metalloproteinase-9
Medical sciences
metalloproteinases
Molecular Structure
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
plant extracts
Plant Roots - chemistry
Plants, Medicinal - chemistry
roots
tumor necrosis factor-alpha
Tumor Necrosis Factor-alpha - antagonists & inhibitors
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Summary:Four new flavonoid glucosides, 3′,4′-di-O-methylquercetin-7-O-[(4′′→13′′′)-2′′′,6′′′,10′′′,14′′′-tetramethylhexadec-13′′′-ol-14′′′-enyl]-β-d-glucopyranoside (1), 4′-O-methylkaempferol-3-O-[(4′′→13′′′)- 2′′′,6′′′,10′′′,14′′′-tetramethylhexadecan-13′′′-olyl]-β-d-glucopyranoside (2), 3′,4′-di-O-methylbutin-7-O-[(6′′→1′′′)-3′′′,11′′′-dimethyl-7′′′-methylenedodeca-3′′′,10′′′-dienyl]-β-d-glucopyranoside (3), and 4′-O-methylbutin-7-O-[(6′′→1′′′)-3′′′,11′′′-dimethyl-7′′′-hydroxymethylenedodecanyl]-β-d-glucopyranoside (4), along with the three known compounds were isolated from the methanol extract of Catharanthus roseus hairy roots. Their structures were elucidated spectroscopically. The new flavonoid glucosides inhibited both MMP-9 activity and TNF-α production in THP-1 cells treated with lipopolysaccharide.
ISSN:0163-3864
1520-6025
DOI:10.1021/np800378q