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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)

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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 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 (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.

Key words

Hypericum oblongifolium Wall. - Clusiaceae - xanthonolignoids - hypericorin A - hypericorin B - anti-inflammatory (respiratory burst)

Supporting Information

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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