Planta Med 2011; 77(14): 1651-1654
DOI: 10.1055/s-0030-1271027
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

New Antimycobacterial Triterpenoids from Rhus taitensis

Raquel C. Jadulco1 , Michael Koch1 , Ryan M. Van Wagoner2 , Christopher Pond1 , Osia G. Gideon3 , Teatulohi Matainaho3 , Pius Piskaut4 , Louis R. Barrows1
  • 1Department of Pharmacology and Toxicology, University of Utah, Salt Lake City, Utah, USA
  • 2Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah, USA
  • 3School of Medicine and Health Sciences, University of Papua New Guinea, Boroko, NCD, Papua New Guinea
  • 4School of Natural and Physical Sciences, University of Papua New Guinea, Boroko, NCD, Papua New Guinea
Further Information

Publication History

received February 2, 2011 revised March 24, 2011

accepted March 29, 2011

Publication Date:
03 May 2011 (online)

Abstract

Two new triterpenoids were isolated from the leaves and twigs of Rhus taitensis. Their structures were elucidated by 1D and 2D NMR spectroscopic studies as 1,10,24,25,30-pentahydroxysqualene (1) and dammar-20(22),24-diene-3β,26,27−triol (2). Both compounds exhibited moderate antimycobacterial activities with an MIC of 45 µg/mL.

References

  • 1 Noro J C, Barrows L R, Gideon O G, Ireland C M, Koch M, Matainaho T, Piskaut P, Pond C D, Bugni T S. Tetrahydroxysqualene from Rhus taitensis shows antimicrobacterial activity against Mycobacterium tuberculosis.  J Nat Prod. 2008;  1 1623-1624
  • 2 Akihisa T, Franzblau S G, Tokuda H, Tagata M, Ukiya M, Matsuzawa T, Metori K, Kimura Y, Suzuki T, Yasukawa K. Antitubercular activity and inhibitory effects on Epstein-Barr virus activation of sterols and polyisoprenepolyols from an edible mushroom, Hypsizigus marmoreus.  Biol Pharm Bull. 2005;  28 1117-1119
  • 3 Cantrell C L, Franzblau S G, Fischer N H. Antimycobacterial plant terpenoids.  Planta Med. 2001;  6 685-694
  • 4 Vik A, James A, Gundersen L L. Screening of terpenes and derivatives of antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.  Planta Med. 2007;  3 1410-1412
  • 5 Rajab M S, Cantrell C L, Franzblau S G, Fischer N H. Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study.  Planta Med. 1998;  64 2-4
  • 6 Asakawa J, Kasai R, Yamasaki K, Tanaka O. 13C NMR study of ginseng sapogenins and their related dammarane type triterpenes.  Tetrahedron. 1977;  33 1935-1939
  • 7 Torpocco V, Chavez H, Esteves-Braun A, Ravelo A G. New dammarane triterpenes from Maytenus macrocarpa.  Chem Pharm Bull (Tokyo). 2007;  55 812-814
  • 8 Yoshikawa M, Zhang Y, Wang T, Nakamura S, Matsuda H. New triterpene constituents, folisalacins A(1)-A(4), B(1)-B(3), and C, from the leaves of Salacia chinensis.  Chem Pharm Bull (Tokyo). 2008;  56 915-920
  • 9 Zhang Q, Yang X, Zhu H, Yao Y, Hao X, Song B. Triterpenoids of Glechoma longituba (Nakai) Kupr.  Zhongcaoyao. 2006;  37 1780-1781
  • 10 Akihisa T, Franzblau S G, Ukiya M, Okuda H, Zhang F, Yasukawa K, Suzuki T, Kimura Y. Antitubercular activity of triterpenoids from Asteraceae flowers.  Biol Pharm Bull. 2005;  28 158-160
  • 11 Suksamrarn S, Panseeta P, Kunchnawatta S, Distaporn T, Ruktasing S, Suksamrarn A. Ceanothane- and lupane-type triterpenes with antiplasmodial and antimycobacterial activities from Ziziphus cambodiana.  Chem Pharm Bull (Tokyo). 2006;  54 535-537
  • 12 Park I H, Piao L Z, Kwon S W, Lee Y J, Cho S Y, Park M K, Park J H. Cytotoxic dammarane glycosides from processed ginseng.  Chem Pharm Bull (Tokyo). 2002;  50 538-540
  • 13 Yürüker A, Orjala J, Sticher O, Rali T. Triterpenes from Rhus taitensis.  Phytochemistry. 1998;  48 863-866
  • 14 Bugni T S, Harper M K, McCulloch M W B, Reppart J, Ireland C M. Fractionated marine invertebrate extract libraries for drug discovery.  Molecules. 2008;  13 1372-1383
  • 15 Franzblau S G, Witzig R S, McLaughlin J C, Torres P, Madico G, Hernandez A, Degnan M T, Cook M B, Quenzer V K, Ferguson R M, Gilman R H. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay.  J Clin Microbiol. 1998;  36 362-366
  • 16 Foongladda S, Roengsanthia D, Arjrattanakool W, Chuchottaworn C, Chaiprasert A, Franzblau S G. Rapid and simple MTT method for rifampicin and isoniazid susceptibility testing of Mycobacterium tuberculosis.  Int J Tuberc Lung Dis. 2002;  6 1118-1122
  • 17 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
  • 18 Marshall K M, Matsumoto S S, Holden J A, Concepcion G P, Tasdemir D, Ireland C M, Barrows L R. The anti-neoplastic and novel topoisomerase II-mediated cytotoxicity of neoamphimedine, a marine pyridoacridine.  Biochem Pharmacol. 2003;  66 447-458

Prof. Dr. Louis R. Barrows

Department of Pharmacology and Toxicology
University of Utah

30 S. 2000 E.

Salt Lake City, Utah 84112

USA

Phone: +1 80 15 82 45 47

Fax: +1 80 15 85 51 11

Email: lbarrows@pharm.utah.edu

>