Download PDF
Planta Med 2016; 82(01/02): 131-137
DOI: 10.1055/s-0035-1557875
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antimicrobial and Antileishmanial Activities of Diterpenoids Isolated from the Roots of Salvia deserta

Jennifer Búfalo
1   Institute of Biosciences (IB), UNESP – Univ. Estadual Paulista, Botucatu, São Paulo, Brazil
2   United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, Mississippi, U. S. A.
,
Charles L. Cantrell
2   United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, Mississippi, U. S. A.
,
Melissa R. Jacob
3   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi, U. S. A.
,
Kevin K. Schrader
2   United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, Mississippi, U. S. A.
,
Babu L. Tekwani
3   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi, U. S. A.
4   Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, Mississippi, U. S. A.
,
Tatyana S. Kustova
5   Institute of Plant Biology and Biotechnology, Timiriazeva, Republic of Kazakhstan
,
Abbas Ali
3   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi, U. S. A.
,
Carmen S. F. Boaro
1   Institute of Biosciences (IB), UNESP – Univ. Estadual Paulista, Botucatu, São Paulo, Brazil
› Author Affiliations
Further Information

Publication History

received 09 February 2015
revised 16 July 2015

accepted 19 July 2015

Publication Date:
26 August 2015 (online)

    Permissions and Reprints

Abstract

Four diterpenes with biological activity were isolated from Salvia deserta roots. Taxodione was considered leishmanicidal with an IC50 value of 1.46 µM (0.46 mg/L) against Leishmania donovani and also exhibited antifungal and antimicrobial activities. Ferruginol displayed the greatest activity [24-h IC50 of 4.5 µM (1.29 mg/L)] against the fish pathogenic bacteria Streptococcus iniae. The crude extract fraction that contained the isolated compounds 7-O-acetylhorminone and horminone showed stronger in vitro antibacterial activity (1.3 mg/L for Staphylococcus aureus and 1.1 mg/L for methicillin-resistant S. aureus) than the compounds tested alone. 7-O-Acetylhorminone and horminone exhibited a synergistic effect against methicillin-resistant S. aureus (FIC of 0.2), and horminone had better activity against S. aureus with respect to other compounds isolated from S. deserta roots. In larvicidal bioassays, these extracts and isolated pure compounds did not show any activity at the highest dose of 125 mg/L against 1-d-old Aedes aegypti larvae.

Key words

Salvia deserta - Lamiaceae - diterpenoid - leishmania - antimicrobial activity - Staphylococcus aureus - Streptococcus iniae

Supporting Information

 

  • References

  • 1 Mabberley DJ. The plant book. 3rd. edition. Cambridge: Cambridge University Press; 2008: 1040
    Google Scholar
  • 2 Standley P, Williams L. Flora of Guatemala. Fieldiana Bot 1973; 24: 237-317
    PubMedGoogle Scholar
  • 3 Topçu G. Bioactive triterpenoids from Salvia species. J Nat Prod 2006; 69: 482-487
    CrossrefPubMedGoogle Scholar
  • 4 Ulubelen A, Oksuz S, Topcu G, Goren AC, Voelter W. Antibacterial diterpenes from the roots of Salvia blepharochlaena . J Nat Prod 2001; 64: 549-551
    CrossrefPubMedGoogle Scholar
  • 5 Najaran ZT, Mousavi SH, Tajfard F, Asili J, Soltani S, Hatamipour M, Emami SA. Cytotoxic and apoptogenic properties of three isolated diterpenoids from Salvia chorassanica through bioassay-guided fractionation. Food Chem Toxicol 2013; 57: 346-351
    CrossrefPubMedGoogle Scholar
  • 6 Badisa RB, Tzakou O, Couladis M, Pilarinou E. Cytotoxic activities of Salvia of the Labiatae family. Pharm Biol 2005; 42: 640-645
    CrossrefPubMedGoogle Scholar
  • 7 Zhang Y, Jiang P, Ye M, Kim SH, Jiang C, Lü J. Tanshinones: sources, pharmacokinetics and anti-cancer activities. Int J Mol Sci 2012; 13: 13621-13666
    CrossrefPubMedGoogle Scholar
  • 8 Sairafianpour M, Christensen J, Staerk D, Budnik BA, Kharazmi A, Bagherzadeh K, Jaroszewski JW. Leishmanicidal, antiplasmodial and cytotoxic activity of novel diterpenoid 1,2 quinones from Perovskia abrotanoides: new source of thanshinones. J Nat Prod 2001; 64: 1398
    CrossrefPubMedGoogle Scholar
  • 9 Fraga BM, Díaz CE, Guadaño A, González-Coloma A. Diterpenes from Salvia broussonetii transformed roots and their insecticidal activity. J Agric Food Chem 2005; 13: 5200-5206
    PubMedGoogle Scholar
  • 10 Li M, Li Q, Zhang C, Zhang N, Cui Z, Huang L, Xiao P. An ethnopharmacological investigation of medicinal Salvia plants (Lamiaceae) in China. Acta Pharm Sin B 2013; 4: 273-280
    PubMedGoogle Scholar
  • 11 Hassanzadeh MK, Emami SA, Asili J, Tayarani Najaran Z. Review of the essential oil composition of Iranian Lamiaceae. J Essent Oil Res 2011; 23: 1-40
    PubMedGoogle Scholar
  • 12 Lu Y, Foo LY. Polyphenolics of Salvia: a review. Phytochemistry 2002; 59: 117-140
    CrossrefPubMedGoogle Scholar
  • 13 Tezuka Y, Kasimu R, Li JX, Basnet P, Tanaka TN, Kadota S. Constituents of roots of Salvia deserta Shang. (Xinjiang-Danshen). Chem Pharm Bull 1998; 46: 107-112
    CrossrefPubMedGoogle Scholar
  • 14 Wang BQ. Salvia miltiorrhiza: chemical and pharmacological review of a medicinal plant. J Med Plants Res 2010; 4: 2813-2820
    PubMedGoogle Scholar
  • 15 Wu Y, Ni Z, Shi Q, Dong M, Kiyota H, Gu Y, Cong B. Constituents from Salvia species and their biological activities. Chem Rev 2012; 112: 5967-6026
    CrossrefPubMedGoogle Scholar
  • 16 Bozan B, Ozturk N, Kosar M, Tunalier Z, Baser KHC. Antioxidant and free radical scavenging activities of eight Salvia species. Chem Nat Compd 2002; 38: 198-200
    CrossrefPubMedGoogle Scholar
  • 17 Bruneton J. Pharmacognosy, phytochemistry, medicinal plants. 2nd. edition. Hampshire: Intercept Ltd.; 1999: 1136
    Google Scholar
  • 18 Pavlov NV. Flora of Kazakhstan. Alma-Ata: Izd-vo Akademii nauk Kazakhskoi˘ SSR; 1964: 430
    Google Scholar
  • 19 Sokolov PD. Plant resources of the USSR. Leningrad: Nauka; 1991: 73-74
    Google Scholar
  • 20 Savona G, Bruno M, Rodriguez B, Marco JL. Triterpenoids from Salvia deserta . Phytochemistry 1987; 26: 3305-3308
    CrossrefPubMedGoogle Scholar
  • 21 Hirasawa Y, Izawa E, Matsuno Y, Kawahara N, Goda Y, Morita H. Taxodistines A and B, abietane-type diterpenes from Taxodium distichum . Bioorg Med Chem Lett 2007; 17: 5868-5871
    CrossrefPubMedGoogle Scholar
  • 22 Kusumoto N, Ashitani T, Murayama T, Ogiyama K, Takahashi K. Antifungal abietane-type diterpenes from the cones of Taxodium distichum Rich. J Chem Ecol 2010; 36: 1381-1386
    CrossrefPubMedGoogle Scholar
  • 23 Van Zyl RL, Khan F, Edwards TJ, Drewes SE. Antiplasmodial activities of some abietane diterpenes from the leaves of five Plectranthus species. S Afr J Sci 2008; 104: 62-64
    PubMedGoogle Scholar
  • 24 Kupchan SM, Karim A, Marcks C. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum . J Am Chem Soc 1968; 9: 5923-5924
    PubMedGoogle Scholar
  • 25 Ulubelen A, Topcu G, Chai H, Pezzuto JM. Cytotoxic activity of diterpenoids isolated from Salvia hypargeia . Pharm Biol 1999; 37: 148-151
    CrossrefPubMedGoogle Scholar
  • 26 Kuzma L, Wysokinska H, Rozalski M, Budzynska A, Wieckowska-Szakiel M, Sadowska B, Paszkiewicz M, Kisiel W, Różalska B. Antimicrobial and anti-biofilm properties of new taxodione derivative from hairy roots of Salvia austriaca . Phytomedicine 2012; 14: 1285-1287
    PubMedGoogle Scholar
  • 27 Machumi F, Samoylenko V, Yenesew A, Derese S, Midiwo JO, Wiggers FT, Jacob MR, Tekwani BL, Khan SI, Walker LA, Muhammad I. Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum . Nat Prod Commun 2010; 5: 853-858
    PubMedGoogle Scholar
  • 28 Mothana RA, Al-Said MS, Al-Musayeib NM, El Gamal AA, Al-Massarani SM, Al-Rehaily AJ, Abdulkader M, Maes L. In vitro antiprotozoal activity of abietane diterpenoids isolated from Plectranthus barbatus Andr. Int J Mol Sci 2014; 15: 8360-8371
    CrossrefPubMedGoogle Scholar
  • 29 Schrader KK, Cantrell CL, Mamonov LK, Kustova TS. Bioassay-directed isolation and evaluation of harmine from the terrestrial plant Peganum harmala L. for antibacterial activity against Flavobacterium columnare . J Microb Res 2013; 6: 255-260
    PubMedGoogle Scholar
  • 30 Marcos IS, Beneitez RF, Moro RF, Basabe DD, Urones JG. Lateral lithiation in terpenes: synthesis of (+)-ferruginol and (+)-sugiol. Tetrahedron 2010; 66: 7773-7780
    CrossrefPubMedGoogle Scholar
  • 31 Al-Hazimi HG, Miana GA. The diterpenoids of Salvia Species (Part II). J Chem Soc Pakistan 1994; 16: 46-63
    PubMedGoogle Scholar
  • 32 Schrader KK, Harries MD. A rapid bioassay for bactericides against the catfish pathogens Edwardsiella ictaluri and Flavobacterium columnare . Aquac Res 2006; 37: 928-937
    CrossrefPubMedGoogle Scholar
  • 33 Nakano H, Schrader KK, Mamonov LK, Kustova TS, Mursaliyeva VK, Cantrell CL. Isolation and identification of Flavobacterium columnare and Streptococcus iniae antibacterial compounds from the terrestrial plant Atraphaxis laetevirens . J Agric Food Chem 2012; 60: 10415-10419
    CrossrefPubMedGoogle Scholar
  • 34 Kolak US, Ari S, Birman H, Hasancebi S, Ulubelen A. Cardioactive diterpenoids from the roots of Salvia amplexicaulis . Planta Med 1999; 67: 761-763
    Article in Thieme ConnectPubMedGoogle Scholar
  • 35 Ulubelen A, Birman H, Okusuz S, Topcu G, Kolak U, Barla A, Voelter W. Cardioactive diterpenes from the roots of Salvia eriophora . Planta Med 2002; 68: 818-821
    Article in Thieme ConnectPubMedGoogle Scholar
  • 36 Slamenova D, Masterova I, Labaj J, Horvathova E, Kubala P, Jakubikoca J, Wsolova L. Cytotoxic and DNA-damaging effects of diterpenoid quinones from the roots of Salvia officinalis L. on colonic an hepatic human cells cultured in vitro . Basic Clin Pharmacol 2004; 94: 282-290
    PubMedGoogle Scholar
  • 37 Ulubelen A. Cardioactive and antibacterial terpenoids from some Salvia species. Phytochemistry 2003; 64: 395-399
    CrossrefPubMedGoogle Scholar
  • 38 Jacob MR, Walker LA. Natural products and antifungal drug discovery. In: Ernst EJ, Rogers PD, editors Antifungal agents: methods and protocols. Totowa, NJ: Humana Press; 2005: 83-109
    CrossrefGoogle Scholar
  • 39 Adams RP. Identification of essential oil components by gas chromatography/mass spectrometry, 4th edition. Carol Stream: Allured Books; 2009: 804
    Google Scholar
  • 40 Makler MT, Hinrichs DJ. Measurement of the lactate dehydrogenase activity of Plasmodium falciparum as an assessment of parasitemia. Am J Trop Med Hyg 1993; 48: 205-210
    PubMedGoogle Scholar
  • 41 Sodji Q, Patil V, Jain S, Kornacki JR, Mrksich M, Tekwani BL, Oyelere AK. The antileishmanial activity of isoforms 6- and 8-selective histone deacetylase inhibitors. Bioorg Med Chem Lett 2014; 24: 4826-4830
    CrossrefPubMedGoogle Scholar
  • 42 Ali A, Demirci B, Kiyan HT, Bernier UR, Tsikolia M, Wedge DE, Khan IA, Baser KHC, Tabanca N. Biting deterrence, repellency, and larvicidal activity of Ruta chalepensis (Sapindales: Rutaceae) essential oil and its major individual constituents against mosquitoes. J Med Entomol 2013; 50: 1267-1274
    CrossrefPubMedGoogle Scholar