Prenylated flavonoids of the leaves of Macaranga conifera with inhibitory activity against cyclooxygenase-2

• Published in: Phytochemistry (Oxford) 2002-12, Vol.61 (7), p.867-872
• Main Authors: Jang, Dae Sik, Cuendet, Muriel, Hawthorne, Michael E., Kardono, Leonardus B.S., Kawanishi, Kazuko, Fong, Harry H.S., Mehta, Rajendra G., Pezzuto, John M., Kinghorn, A.Douglas
• Format: Article
• Language: English
• Subjects: 5,4′-Dihydroxy-[2″-(1-hydroxy-1-methylethyl)dihydrofurano]-(7,8:5″,4″)flavanone; 5-Hydroxy-4′-methoxy-2″,2″-dimethylpyrano-(7,8:6″,5″)flavanone; Animals; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Biological and medical sciences; Chemical constitution; Chemical Fractionation - methods; Cyclooxygenase 1; Cyclooxygenase 2; Cyclooxygenase 2 Inhibitors; Cyclooxygenase Inhibitors - chemistry; Cyclooxygenase Inhibitors - isolation & purification; Cyclooxygenase Inhibitors - pharmacology; Cyclooxygenase-1 and -2; Euphorbiaceae; Euphorbiaceae - chemistry; Favonoids; Flavonoids - chemistry; Flavonoids - isolation & purification; Flavonoids - pharmacology; Fundamental and applied biological sciences. Psychology; General pharmacology; Inhibitory Concentration 50; Isoenzymes - antagonists & inhibitors; Lonchocarpol A; Macaranga conifera; Mammary Neoplasms, Experimental - drug therapy; Mammary Neoplasms, Experimental - enzymology; Medical sciences; Membrane Proteins; Mice; Mice, Inbred BALB C; Mouse mammary organ culture assay; Nuclear Magnetic Resonance, Biomolecular; Organ Culture Techniques; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Plant Leaves - chemistry; Plant physiology and development; Prostaglandin-Endoperoxide Synthases; Protein Prenylation; Tomentosanol D
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(02)00378-3

Two prenylated flavonoid derivatives, 5-hydroxy-4′-methoxy-2″,2″-dimethylpyrano-(7,8:6″,5″)flavanone ( 1) and 5,4′-dihydroxy-[2″-(1-hydroxy-1-methylethyl)dihydrofurano]-(7,8:5″,4″)flavanone ( 2), were isolated from an ethyl acetate-soluble extract of the leaves of Macaranga conifera using an in vitro activity-guided fractionation procedure based on the inhibition of cyclooxygenase-2. Also obtained were eight known compounds, 5,7-dihydroxy-4′-methoxy-8-(3-methylbut-2-enyl)flavanone ( 3), lonchocarpol A ( 4), sophoraflavanone B ( 5), 5,7-dihydroxy-4′-methoxy-8-(2-hydroxy-3-methylbut-3-enyl)flavanone ( 6), tomentosanol D ( 7), lupinifolinol ( 8), isolicoflavonol ( 9), and 20-epibryonolic acid ( 10). The structures of compounds 1 and 2 were determined using spectroscopic methods. All isolates were tested for their inhibitory effects against both cyclooxygenases-1 and -2, and selected compounds were evaluated in a mouse mammary organ culture assay. Two prenylated flavonoids, 5-hydroxy-4′-methoxy-2″,2″-dimethylpyrano-(7,8:6″,5″)flavanone ( 1) and 5,4′-dihydroxy-[2″-(1-hydroxy-1-methylethyl)dihydrofurano]-(7,8:5″,4″)flavanone ( 2), together with eight known compounds, were isolated from the leaves of Macaranga conifera by bioassay-guided fractionation.