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Constituents of the stems of Macrococculus pomiferus and their inhibitory activities against cyclooxygenases-1 and -2.
- Source :
-
Phytochemistry [Phytochemistry] 2004 Nov; Vol. 65 (21), pp. 2861-6. - Publication Year :
- 2004
-
Abstract
- As part of our program directed towards the discovery of new cancer chemopreventive agents from plants, the EtOAc-soluble extract of the stems of M. pomiferus was found to inhibit the enzyme cyclooxygenase-2 (COX-2). Bioassay-directed fractionation of this extract led to the isolation of two dibenzylbutyrolactone lignans, (8R,8'R)-3'-O-demethyl-5-hydroxymatairesinol (1) and (8R,8'R)-3'-O-demethyl-5-methoxymatairesinol (2), as well as seven known compounds, (-)-5'-methoxyyatein (3), blumenol A, (-)-deoxypodophyllotoxin (anthricin), (-)-deoxypodorhizone, 2,6-dimethoxyhydroquinone, 4-hydroxybenzaldehyde, and beta-sitosterol glucoside. The structures of compounds 1 and 2 were determined using spectroscopic data (1D and 2D NMR, and HREIMS), and the 8R and 8'R absolute stereochemistry was established for both 1 and 2 on the basis of their CD spectra. All isolates obtained in the present study were evaluated for their inhibitory effects with both COX-1 and -2. Of these, only 5'-methoxyyatein (3) showed weak activity against COX-2, while all other compounds isolated were inactive. The COX-2 inhibitory activity of the EtOAc extract was also traced to the presence of several common fatty acids by LC-MS.
- Subjects :
- Antineoplastic Agents, Phytogenic chemistry
Antineoplastic Agents, Phytogenic pharmacology
Cyclooxygenase 1
Cyclooxygenase 2
Cyclooxygenase 2 Inhibitors
Cyclooxygenase Inhibitors chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Plant Extracts chemistry
Plant Extracts pharmacology
Prostaglandin-Endoperoxide Synthases
Cyclooxygenase Inhibitors pharmacology
Isoenzymes antagonists & inhibitors
Menispermaceae chemistry
Plant Stems chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 0031-9422
- Volume :
- 65
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Phytochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 15501253
- Full Text :
- https://doi.org/10.1016/j.phytochem.2004.08.007