Three new pentacyclic triterpenes and some flavonoids from the fruits of an Indian Ayurvedic plant Dendrophthoe falcata and their estrogen receptor binding activity.
Extensive chromatographic screening of extracts of the fruits of the Indian Ayurvedic plant, Dendrophthoe falcata, resulted in the isolation of three new triterpenes, 3beta-acetoxy-1beta-(2-hydroxy-2-propoxy)-11alpha-hydroxy-olean-12-ene (1), 3beta-acetoxy-11alpha-ethoxy-1beta-hydroxy-olean-12-ene (2) and 3beta-acetoxy-1beta-hydroxy-11alpha-methoxy-olean-12-ene (3) along with nine known compounds, 3beta-acetoxy-1beta,11alpha-dihydroxy-olean-12-ene (4), 3beta-acetoxy-1beta,11alpha-dihydroxy-urs-12-ene (5), 3beta-acetoxy-urs-12-ene-11-one (6), 3beta-acetoxy-lup-20(29)-ene (7), 30-nor-lup-3beta-acetoxy-20-one (8), (20S)-3beta-acetoxy-lupan-29-oic acid (9), kaempferol-3-O-alpha-L-rhamnopyranoside (10), quercetin-3-O-alpha-L-rhamnopyranoside (11), and gallic acid (12). The structures of these compounds were determined using 1D and 2D NMR and high resolution electrospray mass spectrometry. These compounds were assayed for binding to estrogen receptors-alpha and beta and kaempferol-3-O-alpha-L-rhamnopyranoside (10) was found to be a ligand for both receptors with greater affinity for beta. The triterpenes (1-9) are reported for the first time in the genus Dendrophthoe and assumes taxonomic significance.
Mallavadhani
Uppuluri Venkata
UV
Traditional and Herbal Drugs Department, Regional Research Laboratory, Bhubaneswar-751 013, India. uvmavadani@yahoo.com
Narasimhan
Kilambi
K
Sudhakar
Akella Venkata Subrahmanya
AV
Mahapatra
Anita
A
Li
Wenkui
W
van Breemen
Richard Bruce
RB
D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification; D005638:Fruit / Q000737:chemistry*; D007194:India; D028183:Loranthaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008515:Medicine, Ayurvedic; D010936:Plant Extracts / Q000032:analysis; D011960:Receptors, Estrogen / Q000187:drug effects*; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
D005419:Flavonoids; D010936:Plant Extracts; D011960:Receptors, Estrogen; D014315:Triterpenes