Planta Med 2011; 77(18): 2013-2018
DOI: 10.1055/s-0031-1280114
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Anti-Inflammatory Xanthones from the Twigs of Hypericum oblongifolium Wall.

Mumtaz Ali1 , 2 , Muhammad Arfan2 , Manzoor Ahmad1 , Kuldip Singh3 , Itrat Anis4 , Habib Ahmad6 , Muhammad Iqbal Choudhary5 , Muhammad Raza Shah5
  • 1Department of Chemistry, University of Malakand, Chakdara, Dir (L), KPK, Pakistan
  • 2Institute of Chemical Sciences, University of Peshawar, Peshawar, KPK, Pakistan
  • 3Department of Chemistry, University of Leicester, Leicester, United Kingdom
  • 4Department of Chemistry, University of Karachi, Karachi, Pakistan
  • 5H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan
  • 6Department of Genetics, University of Hazzara, Mansehra, KPK, Pakistan
Further Information

Publication History

received January 7, 2011 revised June 27, 2011

accepted June 29, 2011

Publication Date:
25 August 2011 (online)

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, 1H NMR, 13C NMR, HMQC, HMBC, and NOESY). We also report herein for the first time the single crystal X-ray structure of compound 6. Compounds 17 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 (IC50 = 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 (IC50 = 2500.85 ± 50.50 µM), while compound 4 was totally inactive at 1000 µg/mL as compared to the positive control used, indomethacin (IC50 = 757.99 ± 5.90 µM), and aspirin (IC50 = 279.44 ± 4.40 µM). Compound 4 was also inactive in comparison with other tested Hypericum compounds.

Supporting Information

References

  • 1 Chopra R N, Chopra I C, Verma B S. Supplement to glossary of Indian medicinal plants. New Delhi: Publication and Information Directorate, CSIR; 1998: 347
  • 2 Rokson N K B, Nasir E, Ali S I. Flora of West Pakistan, Vol. 32. Karachi: Shamim Printing Press; 1973: 1-12
  • 3 Savikin K, Dobric S, Tadic V, Zdunic G. Antiinflammatory activity of ethanol extracts of Hypericum perforatum L., H. barbatum Jacq., H. hirsutum L., H. richeri Vill. and H. androsaemum L. in rats.  Phytother Res. 2007;  21 176-180
  • 4 Ferheen S, Ahmed E, Malik A, Afza N, Lodhi M A, Choudhary M I. Hyperinols A and B, chymotrypsin inhibiting triterpenes from Hypericum oblongifolium.  Chem Pharm Bull. 2006;  54 1088-1090
  • 5 Bennett G J, Lee H H. Xanthones from Guttiferae.  Phytochemistry. 1989;  28 967-998
  • 6 Schmidt W, Abd El-Mawla A M, Wolfender J L, Hostettmann K, Beerhues L. Xanthones in cell cultures of Hypericum androsaemum.  Planta Med. 2000;  66 380-381
  • 7 Oku H, Ueda Y, Iinuma M, Ishiguro K. Inhibitory effects of xanthones from Guttiferae plants on PAF-induced hypotension in mice.  Planta Med. 2005;  71 90-92
  • 8 Rocha L, Marston A, Potterat O, Auxiliadora M, Kaplan C, Stoeckli-Evans H, Hostettmann K. Antibacterial phloroglucinols and flavonoids from Hypericum brasiliense.  Phytochemistry. 1995;  40 1447-1452
  • 9 Jayasuriya H, Clark A M, McChesney J D. New antimicrobial filicinic acid derivatives from Hypericum drummondii.  J Nat Prod. 1991;  54 1314-1320
  • 10 Shiu W K P, Gibbons S. Anti-staphylococcal acylphloroglucinols from Hypericum beanii.  Phytochemistry. 2006;  67 2568-2572
  • 11 Athanasas K, Magiatis P, Fokialakis N, Skaltsounis A L, Pratsinis H, Kletsas D. Hyperjovinols A and B: two new phloroglucinol derivatives from Hypericum jovis with antioxidant activity in cell cultures.  J Nat Prod. 2004;  67 973-977
  • 12 Verotta L. Are acylphloroglucinols lead structures for the treatment of degenerative diseases.  Phytochem Rev. 2002;  1 389-407
  • 13 Albert D, Zündorf I, Dingermann T, Müller W E, Steinhilber D, Werz O. Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase.  Biochem Pharmacol. 2002;  64 1767-1775
  • 14 Matsuhisa M, Shikishima Y, Takaishi Y, Honda G, Ito M, Takeda Y, Shibata H, Higuti T, Kodzhimatov O K, Ashurmetov O. Benzoylphloroglucinol derivatives from Hypericum scabrum.  J Nat Prod. 2002;  65 290-294
  • 15 Zeisser-Labouèbe M, Lange N, Gurny R, Delie F. Hypericin-loaded nanoparticles for the photodynamic treatment of ovarian cancer.  Int J Pharm. 2006;  326 174-181
  • 16 Ferraz A B F, Bordignon S A L, Staats C, Schripsema J, von Poser G L. ChemInform abstract: Benzopyrans from Hypericum polyanthemum.  Phytochemistry. 2001;  57 1227-1230
  • 17 Bernardi A P M, Ferraz A B F, Albring D V, Bordignon S A L, Schripsema J, Bridi R, Dutra-Filho C S, Henriques A T, von Poser G L. Benzophenones from Hypericum carinatum.  J Nat Prod. 2005;  68 784-786
  • 18 Gamiotea-Turro D, Cuesta-Rubio O, Prieto-Gonzalez S, De Simone F, Passi S, Rastrelli L. Antioxidative constituents from the leaves of Hypericum styphelioides.  J Nat Prod. 2004;  67 869-871
  • 19 Cakir A, Mavi A, Yildirim A, Duru M E, Harmandar M, Kazaz C. Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation.  J Ethnopharmacol. 2003;  87 73-83
  • 20 Nahrstedt A, Butterweck V. Lessions learned from herbal medicinal products – the example of St. John's wort.  J Nat Prod. 2010;  73 1015-1021
  • 21 Beretz A, Joly M, Stoclet J C, Anton R. Inhibition of 3,5-AMP phosphodiesterase by biflavonoids and xanthones.  Planta Med. 1979;  36 193-195
  • 22 Suzuki O, Katsumata Y, Oya M, Chari V M, Vermes B, Wagner H, Hostettmann K. Inhibition of type A and type B monoamine oxidases by naturally occurring xanthones.  Planta Med. 1981;  42 17-21
  • 23 Chung M I, Weng J R, Wang J P, Teng C M, Lin C N. Antiplatelet and anti-inflammatory constituents and new oxygenated xanthones from Hypericum geminiflorum.  Planta Med. 2002;  68 25-29
  • 24 Bagchi D, Bagchi M, Stohs S J. Comparative in vitro oxygen radical scavenging ability of zinc methionine and selected zinc salts and antioxidants.  Gen Pharmacol. 1997;  28 85-91
  • 25 Tan A S, Berridge M V. Superoxide produced by activated neutrophils efficiently reduces the tetrazolium salt, WST-1 to produce a soluble formazan: a simple colorimetric assay for measuring respiratory burst activation and for screening anti-inflammatory agents.  J Immunol Methods. 2000;  238 59-68
  • 26 Xiang H, Hu G, Liu P, Chen J, Jia S, Chen Z. Synthesis and antioxidant activity of polyhydroxyxanthones and their derivatives.  Chin J Med Chem. 2005;  15 207-210
  • 27 Siddiqui R A, English D, Harvey K, Cui Y, Martin M I, Wentlands J, Akard L. Phorbal ester-induced priming of superoxide generation by phosphatidic acid-stimulated neutrophils and granule-free neutrophil cytoplasts.  Soc Leukoc Biol. 1995;  58 189-195
  • 28 MacDonald T M, Beard K, Bruppacher R, Hasford J, Lewis M, Logan R F, McNaughton D, Tubert-Bitter P, Van Ganse E, Moore N. The safety of drugs for OTC use: what evidence is required for an NSAID switch?.  Pharmacoepidemiol Drug Saf. 2002;  11 577-584
  • 29 Wu C C, Yen M H, Yang S H, Lin C N. Novel open-chain Cytochalsins from the marine-derived Fungus Spicaria elegans.  J Nat Prod. 2008;  71 1027-1031
  • 30 Cardona M L, Fernández M I, Pedro J R, Seoane E, Vida R. Additional new Xanthones and Xanthonolignoids from Hypericum canariensis.  J Nat Prod. 1986;  49 95-100
  • 31 Hong D, Yin F, Hu L H, Lu P. Sulfonated xanthones from Hypericum sampsonii.  Phytochemistry. 2004;  65 2595-2598
  • 32 Wu Q L, Wang S P, Du L J, Zhang S M, Yang J S, Xiao P G. Xanthones from Hypericum japonicum and H. henryi.  Phytochemistry. 1998;  49 1395-1402
  • 33 Cardona L M, Isabel F, Jose P R, Angel S. Xanthones from Hypericum reflexum.  Phytochemistry. 1990;  29 3003-3006
  • 34 Arfan M, Ali M, Ahmad H, Anis I, Khan A, Choudhary M I, Shah M R. Urease inhibitors from Hypericum oblongifolium Wall.  J Enzyme Inhib Med Chem. 2010;  25 296-299

Assistant Professor Dr. Mumtaz Ali

Department of Chemistry
University of Malakand, Chakdara, Dir (L)

Khyber Pukhtoonkhwa

Pakistan

Phone: +92 3 33 9 48 95 51

Fax: +92 9 45 76 34 91

Email: mumtazphd@gmail.com

Assistant Professor Dr. Manzoor Ahmad

Department of Chemistry
University of Malakand, Chakdara, Dir (L)

Khyber Pukhtoonkhwa

Pakistan

Phone: +92 3 33 3 58 61 44

Fax: +92 9 45 76 34 91

Email: manzoorhej@yahoo.com