Antioxidant, cyclooxygenase and topoisomerase inhibitory compounds from Apium graveolens Linn. seeds.
Cyclooxygenase inhibitory and antioxidant bioassay-directed extraction and purification of celery seeds yielded sedanolide (1), senkyunolide-N (2), senkyunolide-J (3), 3-hydroxymethyl-6-methoxy-2,3-dihydro-1H-indol-2-ol (4), L-tryptophan (6), and 7-[3-(3,4-dihydroxy-4-hydroxymethyl-tetrahydro-furan-2-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-chromen-4-one (7). The structures of compounds 1-7 were determined using spectroscopic methods. Compound 4 is reported here for the first time. At 250 pg ml(-1), compounds 1-4, 6 and 7 displayed prostaglandin H endoperoxide synthase-I (COX-I) and prostaglandin H endoperoxide synthase-II (COX-II) inhibitory activities at pH 7. The acetylated product (5) of compound 4 also inhibited COX-I and COX-II enzymes when tested at 250 microg ml(-1). Compounds 6 and 7 exhibited good antioxidant activity at concentrations of 125 and 250 microg ml(-1). Only compounds 1-3 exhibited topoisomerase-I and -II enzyme inhibitory activity at concentrations of 100, 200 and 200 microg ml(-1), respectively.
Department of Horticulture and National Food Safety and Toxicology Center, Michigan State University, East Lansing 48824, USA.
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D000975:Antioxidants / Q000008:administration & dosage / Q000737:chemistry*; D000077102:Apium; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000008:administration & dosage / Q000737:chemistry*; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D008565:Membrane Proteins; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry*; D011451:Prostaglandin-Endoperoxide Synthases; D012639:Seeds; D059004:Topoisomerase I Inhibitors; D059005:Topoisomerase II Inhibitors
D000975:Antioxidants; D004791:Enzyme Inhibitors; D007527:Isoenzymes; D008565:Membrane Proteins; D010936:Plant Extracts; D059004:Topoisomerase I Inhibitors; D059005:Topoisomerase II Inhibitors; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C496511:PTGS1 protein, human; C496540:PTGS2 protein, human; D011451:Prostaglandin-Endoperoxide Synthases