title: Anti-inflammatory xanthones from the twigs of Hypericum oblongifolium wall.
abstract: Two new xanthonolignoids, hypericorin A (1) and hypericorin B (2), along with five known new source compounds, a xanthonolignoid, kielcorin (3), 4-hydroxy-2,3-dimethoxyxanthone (4), 3,4,5-trihydroxyxanthone (5), 1,3-dihydroxy-5-methoxyxanthone ( 6) and 1,3,7-trihydroxyxanthone (7), were isolated from the stems (twigs) of Hypericum oblongifolium Wall. The structures of the new compounds were deduced on the basis of spectroscopic techniques (EI-MS, HREI-MS, (1)H NMR, (13)C NMR, HMQC, HMBC, and NOESY). We also report herein for the first time the single crystal X-ray structure of compound 6. Compounds 1- 7 were screened for their IN VITRO anti-inflammatory (respiratory burst) inhibiting activities using isolated human neutrophils; compounds 1, 2, 3, 5, and 7 showed significant activities (IC (50) = 816.23 ± 73.30, 985.20 ± 55.80, 965.21 ± 65.80, 907.20 ± 50.80, 975.20 ± 81.10 µM, respectively), compound 6 showed moderate activity (IC (50) = 2500.85 ± 50.50 µM), while compound 4 was totally inactive at 1000 µg/mL as compared to the positive control used, indomethacin (IC (50) = 757.99 ± 5.90 µM), and aspirin (IC (50) = 279.44 ± 4.40 µM). Compound 4 was also inactive in comparison with other tested Hypericum compounds.
authors.affiliation: Department of Chemistry, University of Malakand, Chakdara, Dir (L), KPK, Pakistan. mumtazphd@gmail.com
authors.forename: Mumtaz
authors.initials: M
authors.lastname: Ali
authors.forename: Muhammad
authors.initials: M
authors.lastname: Arfan
authors.forename: Manzoor
authors.initials: M
authors.lastname: Ahmad
authors.forename: Kuldip
authors.initials: K
authors.lastname: Singh
authors.forename: Itrat
authors.initials: I
authors.lastname: Anis
authors.forename: Habib
authors.initials: H
authors.lastname: Ahmad
authors.forename: Muhammad Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.forename: Muhammad Raza
authors.initials: MR
authors.lastname: Shah
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002473:Cell Wall / Q000737:chemistry*; D055598:Chemical Phenomena; D018360:Crystallography, X-Ray; D006801:Humans; D020902:Hypericum / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D009504:Neutrophils / Q000187:drug effects; D018547:Plant Stems / Q000737:chemistry*; D016897:Respiratory Burst / Q000187:drug effects; D044004:Xanthones / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D044004:Xanthones; C571270:hypericorin A; C571271:hypericorin B