PDF herunterladen
Planta Med 2015; 81(07): 594-599
DOI: 10.1055/s-0035-1545841
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antibacterial and Antioxidant Xanthones and Benzophenone from Garcinia smeathmannii

Hugues Fouotsa
1   Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, Yaoundé, Cameroon
2   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Bielefeld, Germany
,
Alain Meli Lannang
2   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Bielefeld, Germany
3   Department of Chemistry, Higher Teachersʼ Training College, University of Maroua, Maroua, Cameroon
,
Jean Paul Dzoyem
4   Department of Biochemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
,
Simplice J. N. Tatsimo
3   Department of Chemistry, Higher Teachersʼ Training College, University of Maroua, Maroua, Cameroon
,
Beate Neumann
5   Department of Chemistry, Inorganic and Structural Chemistry, Bielefeld University, Bielefeld, Germany
,
Celine Djama Mbazoa
1   Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, Yaoundé, Cameroon
,
Andrianambinina Andriamarolahy Razakarivony
2   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Bielefeld, Germany
,
Augustin Ephrem Nkengfack
1   Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, Yaoundé, Cameroon
,
Jacobus N. Eloff
6   Phytomedicine Programme, Department of Paraclinical Sciences, Faculty of Veterinary Science, University of Pretoria, Pretoria, South Africa
,
Norbert Sewald
2   Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Bielefeld, Germany
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 12. November 2014
revised 06. Februar 2015

accepted 08. Februar 2015

Publikationsdatum:
23. März 2015 (online)

Auch verfügbar auf
    Lizenzen und Reprints

Abstract

A new prenylated xanthone, 1,3,5,8-tetrahydroxy-2-(3-methybut-2-enyl)-4-(3,7-dimethylocta-2,6-dienyl) xanthone (1), and a new benzophenone (2), together with four known xanthone derivatives, cheffouxanthone (3), smeathxanthone A (4), smeathxanthone B (5), ananixanthone (6), and two pentacyclic triterpenes, epi-friedelinol (7) and friedelin (8), were isolated from the stem bark of Garcinia smeathmannii. The structures of the compounds were elucidated on the basis of 1D and 2D NMR experiments, and compound 2 was further characterized and confirmed by single X-ray analysis. Compounds 1, 2, and 3 exhibited the most prominent antibacterial activity against gram-positive Enterococcus faecalis with minimal inhibitory concentration values of 8, 8, and 2 µg/mL, respectively, while compounds 1, 3, 4, and 6 showed the capacity to scavenge free radicals.

Key words

Garcinia smeathmannii - Guttiferae - xanthone - benzophenone - antibacterial - antioxidant

Supporting Information

 

  • References

  • 1 Bennett GJ, Lee H. Xanthones from the Guttiferaceae. Phytochemistry 1989; 28: 967-998
    CrossrefPubMedSuche in Google Scholar
  • 2 Waterman PG, Hussain RA. Systematic significance of xanthones, benzophenones and biflavonoids in Garcinia . Biochem Syst Ecol 1983; 11: 21-28
    CrossrefPubMedSuche in Google Scholar
  • 3 Nguyen LH, Harrison LJ. Xanthones and triterpenoids from the bark of Garcinia vilersiana . Phytochemistry 2000; 53: 111-114
    CrossrefPubMedSuche in Google Scholar
  • 4 Permana D, Lajis NH, Mackeen MM, Ali AM, Aimi N, Kitajima M, Takayama H. Isolation and bioactivities of constituents of the roots of Garcinia atroviridis . J Nat Prod 2001; 64: 976-979
    CrossrefPubMedSuche in Google Scholar
  • 5 Suksamrarn S, Suwannapoch N, Phakhodee W, Thanuhiranlert J, Ratananukul P, Chimnoi N, Suksamrarn A. Antimycobacterial activity of prenylated xanthones from the fruits of Garcinia mangostana . Chem Pharm Bull 2003; 51: 857-859
    CrossrefPubMedSuche in Google Scholar
  • 6 Hay AE, Hélesbeux JJH, Duval O, Labaïed M, Grellier P, Richomme P. Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii . Life Sci 2004; 75: 3077-3085
    CrossrefPubMedSuche in Google Scholar
  • 7 Shadid KA, Shaari K, Abas F, Israf DA, Hamzah AS, Syakroni N, Saha K, Lajis NH. Cytotoxic caged-polyprenylated xanthonoids and a xanthone from Garcinia cantleyana . Phytochemistry 2007; 68: 2537-2544
    CrossrefPubMedSuche in Google Scholar
  • 8 Wu CC, Lu YH, Wei BL, Yang SC, Won SJ, Lin CN. Phloroglucinols with prooxidant activity from Garcinia subelliptica . J Nat Prod 2008; 71: 246-250
    CrossrefPubMedSuche in Google Scholar
  • 9 Yu L, Zhao M, Yang B, Bai W. Immunomodulatory and anticancer activities of phenolics from Garcinia mangostana fruit pericarp. Food Chem 2009; 116: 969-973
    CrossrefPubMedSuche in Google Scholar
  • 10 Fouotsa H, Meli Lannang A, Mbazoa CD, Rasheed S, Bishnu PM, Zulfiqar A, Krishna PD, Kengfack AE, Farzana S, Muhammad IC, Sewald N. Xanthones inhibitors of α-glucosidase and glycation from Garcinia nobilis . Phytochem Lett 2012; 5: 236-239
    CrossrefPubMedSuche in Google Scholar
  • 11 Gustafson KR, Blunt JW, Munro MHG, Fuller RW, McKee TC, Cardellina 2nd JH, McMahon JB, Cragg GM, Boyd MR. The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea . Tetrahedron 1992; 48: 10093-10102
    CrossrefPubMedSuche in Google Scholar
  • 12 Ampofo AS, Waterman GP. Xanthones from three Garcinia species. Phytochemistry 1986; 25: 2351-2355
    CrossrefPubMedSuche in Google Scholar
  • 13 Berhaut J. Flore illustrée du Sénégal. Dakar: Ministère du Développement Rural et de LʼHydraulique, Direction des Eaux et Forêts; 1975: 89-90
    Suche in Google Scholar
  • 14 Bouquet A. Féticheurs et Médecines Traditionnelles du Congo (Brazzaville). Paris: O.R.S.T.O.M.; 1969: 133
    Suche in Google Scholar
  • 15 Meli Lannang A, Komguem J, Ngounou NF, Tangmouo JG, Lontsi D, Ajaz A, Iqbal MC, Beiban LS. Atta-ur-Rahman. Antioxidant benzophenones and xanthones from the root bark of Garcinia smeathmannii . Bull Chem Soc Ethiop 2006; 20: 247-252
    PubMedSuche in Google Scholar
  • 16 Komguem J, Meli Lannang A, Manfouo NR, Lontsi D, Ngounou NF, Kuete V, Kamdem WH, Tane P, Ngadjui TB, Sondengam LB, Connelly DJ. Xanthones from Garcinia smeathmannii (Oliver) and their antimicrobial activity. Phytochemistry 2005; 66: 1713-1717
    CrossrefPubMedSuche in Google Scholar
  • 17 Kuete V, Komguem J, Penlap Beng V, Meli Lannang A, Tangmouo JG, Etoa F-X, Lontsi D. Antimicrobial components of the methanolic extract from the stem bark of Garcinia smeathmannii Oliver (Clusiaceae). S Afr J Bot 2007; 73: 347-354
    CrossrefPubMedSuche in Google Scholar
  • 18 Wu YP, Zhao W, Xia ZY, Kong GH, Lu XP, Hu QF, Gao XM. Three novel xanthones from Garcinia paucinervis and their anti-TMV activity. Molecules 2013; 18: 9663-9669
    CrossrefPubMedSuche in Google Scholar
  • 19 Satish K, Kanwal R, Pratibha K. Flavones and acridones from Atalantia wightii . Indian J Chem 2009; 48: 291-294
    PubMedSuche in Google Scholar
  • 20 Hiroyuki M, Emi T, Mitsuaki K, Yoshiyasu F. Three xanthones from Garcinia subelliptica . Phytochemistry 1996; 41: 629-633
    CrossrefPubMedSuche in Google Scholar
  • 21 Nkengfack EA, Mkounga P, Fomum TZ, Meyer M, Bodo B. Globulixanthones A and B, two new cytotoxic xanthones with isoprenoid groups from the root bark of Symphonia globulifera . J Nat Prod 2002; 65: 734-736
    CrossrefPubMedSuche in Google Scholar
  • 22 Ricaldez FT, Vega GRA. Phytochemical study of Rheedia gardneriana . Rev Boliv Quim 2000; 17: 9-14
    PubMedSuche in Google Scholar
  • 23 Nguyen LH, Venkatraman G, Sim KY, Harrison LJ. Xanthones and benzophenones from Garcinia griffithii and Garcinia mangostana . Phytochemistry 2005; 66: 1718-1723
    CrossrefPubMedSuche in Google Scholar
  • 24 Pinto MMM, Sousa ME, Nascimento MSJ. Xanthone derivatives: new insights in biological activities. Curr Med Chem 2005; 12: 2517-2538
    CrossrefPubMedSuche in Google Scholar
  • 25 Chen Y, Fan H, Yang GZ, Jiang Y, Zhong FF, He HW. Prenylated xanthones from the bark of Garcinia xanthochymus and their 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities. Molecules 2010; 15: 7438-7449
    CrossrefPubMedSuche in Google Scholar
  • 26 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H. OLEX2: a complete structure solution, refinement and analysis program. J Appl Cryst 2009; 42: 339-341
    CrossrefPubMedSuche in Google Scholar
  • 27 Sheldrick GM. A short history of SHELX . Acta Cryst 2008; 64: 112-122
    CrossrefPubMedSuche in Google Scholar
  • 28 Eloff JN. A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Med 1998; 64: 711-713
    Thieme ConnectPubMedSuche in Google Scholar
  • 29 Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT Food Sci Technol 1995; 28: 25-30
    CrossrefPubMedSuche in Google Scholar
  • 30 Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 1999; 26: 1231-1237
    CrossrefPubMedSuche in Google Scholar
  • 31 Benzie IF, Strain JJ. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal Biochem 1996; 239: 70-76
    Suche in Google Scholar