Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations
Free accessResearch articleFirst published online May, 2017
Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations
A set of seven diterpenes, three kauranes and four trachylobanes, isolated from the African plant Psiadia punctulata were assayed against Mycobacterium tuberculosis and reached activity comparable with cycloserine, a second line drug used to treat tuberculosis (TB). Several structural properties of those diterpenes, such as lipophilicity, HOMO and LUMO energies, charge density, and intramolecular hydrogen bond (IHB) formation, were obtained by theoretical calculations and compared with their activities. Peculiar correlations were observed, especially between activity, lipophilicity and IHB formation.
CappoenD, JacobsJ, VanTN, ClaessensS, DielsG, AnthonissenR, EinarsdottirT, FauvilleM, VerschaeveL, HuygenK, De KimpeN. (2012) Straightforward palladium-mediated synthesis and biological evaluation of benzo [j]phenanthridine-7,12-diones as anti-tuberculosis agents. European Journal of Medicinal Chemistry, 48, 57–68.
4.
CaonT, CamposCEM, SimõesCMO, SilvaMAS. (2015) Novel perspectives in the tuberculosis treatment: Administration of izoniazid through the skin. International Journal of Pharmaceutics, 494, 463–470.
5.
ZhuN, LinY, LiD, GaoN, LiuC, YouX, JiangJ, JiangW, SiS. (2015) Identification of an anti-TB compound targeting the tyrosyl-tRNA synthetase. Journal of Antimicrobial Chemotherapy, 70, 2287–2294.
LeandroLM, VargasFS, BarbosaPCS, NevesJKO, SilvaJA, Veiga-JúniorVF. (2012) Chemistry and biological activities of terpenoids from Copaiba (Copaifera spp.) oleoresins. Molecules, 17, 3866–3889.
8.
BanerjeeAK, LayaMS, MoraHR, CabreraEV. (2008) The chemistry of bioactive diterpenes. Current Organic Chemistry, 12, 1050–1070.
9.
JumaBF, MidiwoJO, YenesewA, WatermanPG, HeydenreischM, PeterMG. (2006) Three ent-trachylobane diterpenes from the leaf exudates of Psiadia punctulata. Phytochemistry, 67, 1322–1325.
10.
JumaBF, YenesewA, MidiwoJO, WatermanPG. (2001) Flavones and phenylpropenoids in the surface exudate of Psiadia punctulata. Phytochemistry, 57, 571–574.
11.
MidiwoJO, YenesewA, JumaBF, DereseS, AyooJA, AluochAO, GuchuS. (2002) Bioactive compounds from some Kenyan ethnomedicinal plants: Myrsinaceae, Polygonaceae and Piadia punctulata. Phytochemistry Reviews, 1, 311–323.
12.
MidiwoJO, OwuorFAO, JumaBF, WatermanPG. (1997) Diterpenes from the leaf exudate of Psiadia punctulata. Phytochemistry, 45, 117–120.
HelenoVCG, OliveiraKT, LopesJLC, LopesNP, FerreiraAG. (2008) Detailed 1H and 13C NMR structural assignment and relative stereochemistry determination for three closely related sesquiterpene lactones. Magnetic Resonance in Chemistry, 46, 576–581.
15.
SilvaR, HelenoVCG, AlbuquerqueS, BastosJK, SilvaMLA, DonatePM, SilvaGVJ. (2004) Complete assignment of 1H and 13C NMR data for three aryltetralin lignan lactones. Magnetic Resonance in Chemistry, 42, 985–989.
16.
SassDC, HelenoVCG, MoraisGO, LopesJLC, LopesNP, ConstantinoMG. (2011) Selectivity in reduction of natural furanoheliangolides with Stryker's reagent. Organic and Biomolecular Chemistry, 9, 6148–6153.
CarvalhoTC, SimãoMR, AmbrósioSR, FurtadoNAJC, VenezianiRCS, HelenoVCG. Da CostaFB, GomesBPFA, SouzaMGM, ReisEB, MartinsCHG. (2011) Antimicrobial activity of diterpenes from Viguiera arenaria against endodontic bacteria. Molecules, 16, 543–551.
19.
SouzaAB, SouzaMGM, MoreiraMR, FurtadoNAJC, MartinsCHG, BastosJK, SantosRA, HelenoVCG, AmbrósioSR, VenezianiRCS. (2011) Antimicrobial evaluation of diterpenes from Copaifera langsdorffii oleoresin against periodontal anaerobic bacteria. Molecules, 16, 9611–9619.
20.
AndradeBB, MoreiraMR, AmbrósioSR, FurtadoNAJC, CunhaWR, HelenoVCG, SilvaNA, SimãoMR, RochaEMP, MartinsCHG, VenezianiRCS. (2011) Evaluation of ent-kaurenoic acid derivatives for their anticariogenic activity. Natural Product Communications, 6, 777–780.
21.
PalominoJC, MartinA, CamachoM, GuerraH, SwingsJ, PortaelsF. (2002) Resazurin microtiter assay plate: Simple and inexpressive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrobial Agents and Chemotherapy, 46, 2720 – 2722.
22.
van LentheE, BaerendsEJ. (2003) Optimized Slater-type basis sets for the elements 1–118. Journal of Computational Chemistry, 24, 1142–1156.
23.
BeckeAD. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Reviews A, 38, 3098–3100.
24.
PerdewJP. (1986) Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Physical Reviews B, 33, 8822–8824
25.
PerdewJP. (1986) Erratum: Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Physical Reviews B, 34, 7406.
26.
van LentheE, SnijdersJG, BaerendsEJ. (1996) The zero-order regular approximation for relativistic effects: The effect of spin–orbit coupling in closed shell molecules. Journal of Chemistry and Physics, 105, 6505–6516.
27.
van LentheE, van LeeuwenR, BaerendsEJ, SnijdersJG. (1996) Relativistic regular two-component Hamiltonians. International Journal of Quantum Chemistry, 57, 281–293.
28.
van LentheE, BaerendsEJ, SnijdersJG. (1994) Relativistic total energy using regular approximations. Journal of Chemistry and Physics, 101, 9783–9792.
29.
van LentheE, BaerendsEJ, SnijdersJG. (1993) Relativistic regular two-component Hamiltonians. Journal of Chemistry and Physics, 99, 4597–4610.
30.
van LentheE, EhlersA, BaerendsEJ. (1999) Geometry optimizations in the zero order regular approximation for relativistic effects. Journal of Chemistry and Physics, 110, 8943–8953.
BarbieriPA, FantinA, JorgeFE. (2006) Gaussian basis sets of triple and quadruple zeta valence quality for correlated wave functions. Molecular Physics, 104, 2945–2954.
33.
KlamtA. (2005) COSMO-RS: From quantum chemistry to fluid phase thermodynamics and drug design. Elsevier, Amsterdam.
34.
KlamtA. (1995) Conductor-like screening model for real solvents: A new approach to the quantitative calculation of solvation phenomena. Journal of Physical Chemistry, 99, 2224–2235.
35.
KlamtA, JonasV, BürgerT, LohrenzJCW. (1998) Refinement and parametrization of COSMO-RS. Journal of Physical Chemistry A, 102, 5074–5085.
Fonseca GuerraC, SnijdersJG, te VeldeG, BaerendsEJ. (1998) Towards an order-N DFT method. Theoretical Chemistry Accounts; Theory, Computational Model. (Theoretica Chimica Acta), 99, 391–403.
38.
PyeCC, ZieglerT, van LentheE, LouwenJN. (2009) An implementation of the conductor-like screening model of solvation within the Amsterdam density functional package-Part II. COSMO for real solvents. Canadian Journal of Chemistry, 87, 790–797.
39.
te VeldeG, BickelhauptFM, BaerendsEJ, Fonseca GuerraC, van GisbergenSJA, SnijdersJG, ZieglerT. (2001) Chemistry with ADF. Journal of Computational Chemistry, 22, 931–967.
40.
BaderRFW. (1990) Atoms in molecules. A quantum theory. Oxford University Press, Oxford, UK
41.
BaderRFW. (1991) A quantum theory of molecular structure and its aplications. Chemical Reviews, 91, 893–928
42.
BaderRFW. (1998) A bond path: a universal indicator of bonded interactions. Physical Chemistry A, 102, 7314–7323.
43.
AIMAll (Version 13.02.26) (2013) Todd A. Keith, TK Gristmill Software, Overland Park KS, USA. (aim.tkgristmill.com).
44.
SantosER, MondelliMA, PozziLV, CorrêaRS, Salistre-de-AraújoHS, PavanFR, LeiteCQF, EllenaJ, MaltaVRS, MachadoSP, BatistaAA. (2013) New ruthenium(II)/phosphines/diimines complexes: Promising antitumor (human breast cancer) and Mycobacterium tuberculosis fighting agents. Polyhedron, 51, 292–297.
45.
UrzúaA, RezendeMC, MascayanoC, VásquezL. (2008) A structure-activity study of antibacterial diterpenoids. Molecules, 13, 882–891.
46.
MannholdR, PodaGI, OstermannC, TetkoIV. (2009) Calculation of molecular lipophilicity: State-of-the-art and comparison of logP methods on more than 96,000 compounds. Journal of Pharmaceutical Sciences, 98, 861–893.
47.
HughesMN. (2008) Chemistry of nitric oxide and related species. In Methods in enzymology. Vol.436PooleRK. (Ed.), Academic Press, San Diego, pp 3–19.
48.
McAuleyW. (2013) Hydrophobicity and partitioning. In Pharmaceutics: The science of medicine design. DentonP, RostronC. (Eds.). Oxford University Press, United Kingdom, pp 127–146.
49.
SrivastavaAK, PandeyAK, JainS, MisraN. (2015) FT-IR spectroscopy, intra-molecular C-H…O interactions, HOMO, LUMO, MESP analysis and biological activity of two natural products, triclisine and rufescine: DFT and QTAIM approaches. Spectrochimica Acta A, 136, 682–689.
50.
LamchouriF, ToufikH, BouzzineSM, HamidiM, BouachrineM. (2010) Experimental and computational study of biological activities of alkaloids isolated from Perganum harmala seeds. Journal of Materials and Environmental Science, 1, 343–352.
51.
PropelierPLA. (1999) Quantum molecular similarity. Journal of Physical Chemistry A, 103, 2883–2890
52.
LopezAHD, CaramoriGF, CoimbraDF, ParreiraRLT, SilvaEH. (2013) The two faces of hydrogen-bond strength on triple AAA-DDD arrays. ChemPhysChem, 14, 3994–4001.
53.
ParreiraRLT, GalembeckSE. (2006) Computational study of pyrylium cation-water complexes: hydrogen bonds, resonance effects and aromaticity. Journal of Molecular Structure: THEOCHEM, 760, 59–73.
54.
AlexA, MillanDS, PerezM, WakenhutF, WhitlockGA. (2011) Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space. Medicinal Chemical Communications, 2, 669–674.
55.
OverB, McCarrenP, ArturssonP, FoleyM, GordanettoF, GrönbergG, HilgendorfC, LeeMD, MatssonP, MuncipintoG, PellissonM, PerryMWD, SvenssonR, DuvallJR, KihlbergJ. (2014) Impact of stereospecific intramolecular hydrogen bonding on cell permeability and physicochemical properties. Journal of Medicinal Chemistry, 57, 2746–2754.
