Anthraquinones from leaves of Tectona grandis: A detailed study on its antibacterial activity and other biological properties
Keywords:
Anti-bacterial, Anthraquinones, MIC, MTT assay, Antioxidant, Anti-mycobacterial, HPLC profile, Structural studiesAbstract
The search for new molecules against pathogenic species continues unabated due to drug resistance. Tectona grandis, commonly known as teak, is a widespread woody plant with lot of biological properties. In the present study, attempts were made to isolate antibacterial compounds from Tectona grandis against Staphylococcus aureus, Klebsiella pneumoniae, Salmonella paratyphi and Proteus mirabilis at different concentration. Antimycobacterial activity was checked against Mycobacterium tuberculosis. Cytotoxicity of isolated compounds was evaluated. As part of activity studies, antioxidant potential of both compounds was also checked. Antibacterial activity was checked by disc diffusion and microplate dilution method. Cytotoxicity of pure compounds was evaluated by MTT assay. Antioxidant activity was checked against DPPH and ABTS+ free radicals. Two compounds isolated from chloroform extract of leaf showed activity against S. aureus (Compound 1: MIC – 2.5μg/ml, IC50 - 72μg/ml ; Compound 2: MIC - 5 μg/ml, IC50 - 98 μg/ml) and K. pneumoniae (Compound 2: MIC – 6.2 μg/ml, IC50 – 113.5 μg/ml). These compounds failed to show antimycobacterial activity on testing against M. tuberculosis. On cytotoxicity analysis of both compounds against chick embryo fibroblast (CEF), HEK293, HCT119 and L929 cells, compound 2 showed activity against HEK293 (IC50 - 2 μg/ml). Antioxidant activity of these compounds was very low and was able to scavenge only 10% of free radicals even at the highest concentration (1000 μg/ml) tested. Purity of compounds was confirmed by HPLC analysis and structural characterization was carried out based on IR and NMR spectral data with supporting phytochemical results.
References
WHO Traditional medicine strategy. World
Health Organization 2002.
Nathan C. Antibiotics at the crossroads.
Nature 2004;431:899-902.
Baker DD, Chu M, Oza U, Rajgarhia V.
The value of natural products to future
pharmaceutical industry. Natural Prod Rep.
;24:1225-1244.
Chopra I, Hesse L, O’Neil AJ. Exploiting
the understanding of antibiotic action for
discovery of new drugs. J. Appl. Microbiol.
;92:4S-15S.
Labischinski H. Editorial - New Antibiotics.
Int. J. Med. Microbiol. 2001;291:317-318.
Livermore DM. The need for new
antibiotics. Clin. Microbiol. Int. 2004;10:1-
Butler MS. Role of natural product
chemistry in drug discovery. J Nat. Prod.
;67:2141-2153.
Varier PS. Indian Medicinal Plants: A
compendium of 500 species, Orient
Longman, India. 1996;5:245-248.
Khare CP. Indian medicinal plants: An
illustrated dictionary. Springer Verlag,
Heidelberg. 2007:p649.
Sumthong P. Antimicrobial compounds as
side products from the agricultural
processing industry. Chapter 4 - Isolation
and elucidation of quinones in Tectona
grandis - PhD thesis, Faculty of
Pharmacology, University of Leiden; 2007.
Neamatallah A, Yan L, Dewar SJ, Austin B.
An extract from Teak (Tectona grandis)
bark inhibited Listeria monocytogenes and
methicillin resistant Staphylococcus aureus.
Lett. Appl. Microbiol. 2005;41:94-96.
Sumthong P, Damveld RA, Choi YH.
Activity of quinones from Teak (Tectona
grandis) on fungal cell wall stress. Planta
Med. 2006;72:943-944.
Sandermann VW, Simatupang MH. On the
chemistry and biochemistry of Teakwood
(Tectona grandis L. fil). HOLZ als Roh-end
Werkstoff. 1966;190-204.
Hussain H, Krohn K, Ahmad VU, Miana
GA, Greend IR. Lapachol: an overview.
ARKIVOC (ii). 2007;145-171.
Mahesh SK, Nair AJ. Antibacterial,
cytotoxic and antioxidant potential of
different extracts from leaf, bark and wood
of Tectona grandis. Int. J Pharm and Drug
Res. 2010;2:155-158.
Darias V, Bravo L, Rabanal R, SánchezMateo CC, MartIn-Herrera DA. Cytostatic
and antibacterial activity of some
compounds isolated from several
Lamiaceae species from the Canary Islands.
Planta Med. 1990;56:70-72.
Taylor RSL and Towers GHN.
Antibacterial constituents of the Nepalese
medicinal herb, Centipeda minima.
Phytochem. 1998;47:631-634.
Banfi E, Scialino G, Monti-Bragadin C.
Development of a microdilution method to
evaluate Mycobacterium tuberculosis drug
susceptibility. J. Antimicrobial Chemother.
;52:796-800.
Wilson AP. Cytotoxicity and viability
assays in animal cell culture: A practical
approach. 3rd edn. Oxford, UK: Oxford
Univ Press. 2000.
Lee SE, Ju EM, Kim JH. Antioxidant
activity of extracts from Euryale ferox seed.
Exp. Mol. Med. 2002;34:100–106.
Srinivasan D, Nathan S, Suresh T,
Perumalsamy PL. Antimicrobial activity of
certain Indian medicinal plants used in
folkloric medicine. J. of Ethnopharm.
;74:217–220.
Sumthong P, Damveld RA, Choi YH,
Arentshorst M, Ram AFJ, van del Hondel
CAMJJ, Verpoorte R. Activity of quinones
from Teak (Tectona grandis) on fungal cell
wall stress. Planta Med. 2006;72:943-944.
Manojlovic NT, Solujic S, Sukdolak S.
Antimicrobial activity of an extract and
anthraquinones from Caloplaca schaereri.
The Lichenologist. 2002;34:83-85.
Park B, Lee H, Lee S, Piao X, Takeoka GR,
Wong RY, Ahna Y, Kima J. Antibacterial
activity of Tabebuia impetiginosa Martius
ex DC (Taheebo) against Helicobacter
pylori. J. of Ethnopharmac. 2006;105:255–
Chukwujekwu JC, Coombes PH,
Mulholland DA, van Staden J. Emodin, an
antibacterial anthraquinone from the roots
of Cassia occidentalis. South African J of
Bot. 2006;72:295-297.
