Antioxidant, cyclooxygenase and topoisomerase inhibitory compounds from Apium graveolens Linn. seeds

• Published in: Phytomedicine (Stuttgart) Vol. 9; no. 4; pp. 312 - 318
• Main Authors: Momin, R.A., Nair, M.G.
• Format: Journal Article
• Language: English
• Published: Germany Elsevier GmbH 01.05.2002; Urban & Fischer Verlag; Elsevier Science Ltd
• Subjects: antioxidant; Antioxidants - administration & dosage; Antioxidants - chemistry; Apiaceae; Apium graveolens; cyclooxygenase; Cyclooxygenase 1; Cyclooxygenase 2; Dose-Response Relationship, Drug; Enzyme Inhibitors - administration & dosage; Enzyme Inhibitors - chemistry; Humans; Isoenzymes - antagonists & inhibitors; Membrane Proteins; Phytotherapy; Plant Extracts - chemistry; Prostaglandin-Endoperoxide Synthases; Seeds; topoisomerase; Topoisomerase I Inhibitors; Topoisomerase II Inhibitors; cyclooxygenase; topoisomerase; antioxidant; Apium graveolens; Apiaceae
• ISSN: 0944-7113; 1618-095X
• DOI: 10.1078/0944-7113-00131

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 μg 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 μg ml —1. Compounds 6 and 7 exhibited good antioxidant activity at concentrations of 125 and 250 μg ml —1. Only compounds 1–3 exhibited topoisomerase-I and -II enzyme inhibitory activity at concentrations of 100, 200 and 200 μg ml —1, respectively.