Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity.
A triterpenoid, 3beta-cis-p-coumaroyloxy-2alpha,23-dihydroxyolean-12-en-28-oic acid (1), and two natural products, 3beta-trans-p-coumaroyloxy-2alpha,23-dihydroxyolean-12-en-28-oic acid (2) and 23-trans-p-coumaroyloxy-2alpha,3beta-dihydroxyolean-12-en-28-oic acid (3), were isolated from a chloroform-soluble extract of the stems of Eugenia sandwicensis, along with 10 known compounds. Of these compounds, 2 showed significant inhibitory activity (79.2% at 4 microg/ml) in a 7,12-dimethylbenz[a]anthracene-induced mouse mammary organ culture assay system of relevance to cancer chemoprevention. Gallic acid was isolated as an antioxidative constituent of an ethyl acetate-soluble extract of E. sandwicensis stems. Isolates 1-3 were characterized on the basis of spectral and chemical evidence.
Gu
J Q
JQ
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, USA.
Park
E J
EJ
Luyengi
L
L
Hawthorne
M E
ME
Mehta
R G
RG
Farnsworth
N R
NR
Pezzuto
J M
JM
Kinghorn
A D
AD
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000633:toxicity; D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001685:Biological Factors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D028082:Boraginaceae / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry / Q000302:isolation & purification; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D008321:Mammary Glands, Animal / Q000187:drug effects / Q000473:pathology; D051379:Mice; D008807:Mice, Inbred BALB C; D008958:Models, Molecular; D008968:Molecular Conformation; D009924:Organ Culture Techniques; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment
D016588:Anticarcinogenic Agents; D001685:Biological Factors; D003373:Coumaric Acids; D015127:9,10-Dimethyl-1,2-benzanthracene