Nitrogen-Containing Phorbol Esters from Croton ciliatoglandulifer and Their Effects on Cyclooxygenases-1 and -2

Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-06, Vol.69 (6), p.887-890
Main Authors: Rios, M.Y, Aguilar-Guadarrama, A.B
Format: Article
Language:English
Subjects:
Animals
anti-inflammatory activity
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - isolation & purification
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Biological and medical sciences
chemical constituents of plants
chemical structure
Croton
Croton - chemistry
Cyclooxygenase 1 - drug effects
Cyclooxygenase 2 - drug effects
Cyclooxygenase 2 Inhibitors - chemistry
Cyclooxygenase 2 Inhibitors - isolation & purification
Cyclooxygenase 2 Inhibitors - pharmacology
Disease Models, Animal
diterpenoids
Ear
Edema - chemically induced
Edema - drug therapy
enzyme inhibition
esters
Euphorbiaceae
General pharmacology
Medical sciences
medicinal plants
Mexico
Mice
nitrogen
Nitrogen - chemistry
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
phorbol
Phorbol Esters - chemistry
Phorbol Esters - isolation & purification
Phorbol Esters - pharmacology
phytochemicals
plant extracts
Plants, Medicinal - chemistry
prostaglandin synthase
spectral analysis
Tetradecanoylphorbol Acetate - pharmacology
traditional medicine
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Summary:Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4), along with six known compounds, were isolated from the aerial parts of Croton ciliatoglandulifer. An anti-inflammatory activity of a hexane extract of this plant was demonstrated against ear edema in mice produced by 12-O-tetradecanoylphorbol 13-acetate, and compounds 1, 4, and 3beta-O-acetyloleanolic acid (5) were active when evaluated against cyclooxygenases-1 and -2.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0504311