Planta Med 2003; 69(9): 877-879
DOI: 10.1055/s-2003-43223
Letter
© Georg Thieme Verlag Stuttgart · New York

Iridoid Glucosides from the Flowers of Barleria lupulina

Sunit Suksamrarn1 , Kanjana Wongkrajang2 , Kanyawim Kirtikara3 , Apichart Suksamrarn2
  • 1Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, Thailand
  • 2Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, Thailand
  • 3National Center for Genetic Engineering and Biotechnology, National Science and Technology Development Agency, Pathumthani, Thailand
Further Information

Publication History

Received: January 20, 2003

Accepted: May 3, 2003

Publication Date:
04 November 2003 (online)

Abstract

A new iridoid diglucoside, lupulinoside, and eight known iridoid glucosides, acetylbarlerin, ipolamiidoside (3), 6-O-acetylshanzhiside methyl ester, barlerin, shanzhiside methyl ester, mussaenosidic acid, 8-O-acetylshanzhiside, and shanzhiside have been isolated from the flowers of Barleria lupulina. The structure of the new compound was established as 8-O-acetyl-2′-O-(β-glucopyranosyl)mussaenoside by spectroscopic, especially 2D NMR, techniques. When tested for anti-herpes simplex type 1 activity, only compound 3 exhibited antiviral properties. None of the compounds showed cytotoxic effects to the vero cells and none of them inhibited cyclooxygenase-2 enzyme.

References

  • 1 Bunyapraphatsara N, Chokechaijaroenporn O, editors. Thai Medicinal Plants. Vol. 4 Faculty of Pharmacy, Mahidol University and National Center for Genetic Engineering and Biotechnology Bangkok; 2000: pp. 675-7
  • 2 Yoosook C, Panpisutchai Y, Chaichana S, Santisuk T, Reutrakul V. Evaluation of anti-HSV-2 activities of Barleria lupulina and Clinacanthus nutans .  Journal of Ethnopharmacology. 1999;  67 179-87
  • 3 Suksamrarn A. Iridoid glucosides from Barleria lupulina .  Journal of Natural Products. 1986;  49 179
  • 4 Byrne L T, Sasse J M, Sketon B W, Suksamrarn A, White A H. The minor iridoid glucosides of Barleria lupulina: isolation, crystal structure and plant growth-inhibiting properties of 6-O-acetylshanzhiside methyl ester.  Australian Journal of Chemistry. 1987;  40 785-94
  • 5 Tuntiwachwuttikul P, Pancharoen O, Taylor W C. Iridoid glucosides of Barleria lupulina .  Phytochemistry. 1998;  49 163-6
  • 6 Kanchanapoom T, Kasai R, Yamasaki K. Iridoid glucosides from Barleria lupulina .  Phytochemistry. 2001;  58 337-41
  • 7 Bianco A, Guiso M, Ivarone C, Marini-Bettolo R, Trogolo C. Iridoids. XXI. The stereochemistry of ipolamiide and the structure of its natural 8-O-acetyl derivative, ipolamiidoside.  Gazzetta Chimica Italiana. 1976;  106 947-53
  • 8 Damtoft S, Hansen S B, Jacobsen B, Jensen S R, Nielsen B J. Iridoid glucosides from Melampyrum .  Phytochemistry. 1984;  23 2387-9
  • 9 Ersöz T, Ivancheva S, Akbay P, Sticher O, Calis I. Iridoid and phenylethanoid glycosides from Phlomis tuberosa L.  Zeitschrift für Naturforschung. 2001;  56c 695-8
  • 10 Inouye H, Saito S, Shingu T. Ein weiteres neues Iridoidglucosid aus Gardenia jasminoides: Shanzhisid. Tetrahedron Letters 1970: 3581-4
  • 11 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. New colorimetric cytotoxicity assay for anticancer-drug screening.  Journal of National Cancer Institute. 1990;  82 1107-12
  • 12 Kirtikara K, Morham S G, Raghow R, Laulederkind S J, Kanekura T, Goorha S, Ballou L R. Compensatory prostaglandin E2 biosynthesis in cyclooxygenase 1 or 2 null cells.  Journal of Experimental Medicine. 1998;  187 517-23
  • 13 Damtoft S, Jensen S R, Nielsen B J. Structural revision of barlerin and acetylbarlerin.  Tetrahedron Letters. 1982;  23 4155-6

Assoc. Prof. Dr. Apichart Suksamrarn

Department of Chemistry

Faculty of Science

Ramkhamhaeng University

Bangkok 10240

Thailand

Fax: +662-02-3108381

Email: apichart@ram1.ru.ac.th.

    >