Plant growth inhibitory activities by secondary metabolites isolated from Latin American flora

Céspedes, Carlos L.; Marín, Juan Camilo; Domı́nguez, Mariana; Ávila, José G.; Serrato, Blanca

doi:10.1016/s1572-557x(05)02021-0

Cited by 13 publications

(9 citation statements)

References 63 publications

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“…It appears that the trypanocidal activity increases with the presence on an α,β-unsaturated carbonyl, since rotundifolone and perillyl aldehyde containing this functional group were the most potent compounds. This suggestion is supported by previous findings that the presence of a carbonyl group (aldehyde or ketone) conjugated to a C-C double bond seems to be important for the biological activity of many compounds [4,[18][19][20]. In line with this is the finding that perillyl alcohol, which contains a hydroxyl group, was 40 to 100 times less trypanocidal than its analogue perillyl aldehyde.…”

supporting

confidence: 76%

Evaluation of Antiparasitc Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone and Analogues against Trypanosoma brucei

2016

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Considering the pressing need for new drugs to treat sleeping sickness and Nagana disease, essential oil, its principal constituent rotundifolone, and four related-menthane-type monoterpenes (two stereoisomers of limonene epoxide, perillyl alcohol, and perillyl aldehyde) were investigated for their activity against bloodstream forms of . The general cytotoxicity of the compounds was determined with human myeloid HL-60 cells. The effect of the essential oil and the monoterpenes on the growth of parasite and human cells was evaluated in cell cultures with the resazurin viability assay. Of all of the compounds tested, essential oil, rotundifolone, and perillyl aldehyde showed the highest trypanocidal activities with 50 % growth inhibition (GI) and minimum inhibitory concentration values of 0.3 µg/mL and 1 µg/mL, respectively. In contrast, HL-60 cells were considerably less sensitive to the compounds with minimum inhibitory concentration values of 100 µg/mL and GI values ranging between 3.4 to 13.8 µg/mL. As a consequence of this, GI and minimum inhibitory concentration ratios of cytotoxic to trypanocidal activity (selectivity index) of these three compounds were promising with values of 11-45 and 100, respectively. These results indicate that the -menthane-type monoterpenes rotundifolone and perillyl aldehyde are interesting lead candidates for further rational antitrypanosomal drug development.

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supporting

confidence: 76%

Evaluation of Antiparasitc Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone and Analogues against Trypanosoma brucei

2016

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“…Although no phytotoxic effects from the oils of L. sempervirens were detected during the present experiments, this should be evaluated in greater depth in future studies. Some investigators have suggested that essential oils from the leaves of L. sempervirens inhibit seed germination and seedling growth of some crops,22 but other studies in cut flowers have demonstrated that safrole, the main compound of these oils, posed no phytotoxicity when applied as fumigant 44…”

Section: Discussionmentioning

confidence: 99%

“…For instance, piperonyl butoxide, the well‐known insecticidal synergist, is derived from safrole 20. Essential oils from the leaves of L. sempervirens have shown biological activity as insecticide, fungicide and acaricide, as well as plant growth regulator 18, 21–23…”

Section: Introductionmentioning

confidence: 99%

Bioactivity of essential oils from leaves and bark of Laurelia sempervirens and Drimys winteri against Acyrthosiphon pisum

Zapata

Lognay²,

Smagghe

2010

Pest. Manag. Sci.

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“…They were tested at 90% or higher purity, determined by HPLC. The compounds assayed were: vanillin ( 1 ) and, 4-hydroxy-3-methoxycinnamaldehyde ( 2 ), both isolated from Melia azedarach (Carpinella et al, 2003 ), ilicol ( 3 ) isolated from Flourensia oolepis (Diaz Napal and Palacios, 2013 ), scopoletin ( 4 ) obtained from M. azedarach (Carpinella et al, 2005 ), ( Z,Z )-5-(trideca-4,7-dienyl)-resorcinol ( 5 ) isolated from Lithrea molleoides (Carpinella et al, 2011 ), 2′,4′-dihydroxychalcone ( 6 ) and (-)-pinocembrin ( 7 ) both obtained from F. oolepis (Diaz Napal et al, 2009 ; Joray et al, 2015 ), naringenin ( 8 ) isolated from Baccharis salicifolia (Céspedes et al, 2006 ; del Corral et al, 2012 ), dalenin ( 9 ) obtained from Dalea elegans (Chiari et al, 2011 ), apigenin ( 10 ) isolated from B. salicifolia (del Corral et al, 2012 ), quercetin ( 11 ), 3- O -methylquercetin ( 12 ), and 23-methyl-6- O -desmethylauricepirone ( 13 ) obtained from Achyrocline satureioides (Joray et al, 2011 , 2013 ) and (±)-pinoresinol ( 14 ) and meliartenin ( 15 ) both obtained from M. azedarach (Carpinella et al, 2002 , 2003 ). 1-acetoxy-(+)-pinoresinol ( 16 ) (Figure 1 ) was purchased from Chem Faces (Wuhan, PR).…”

Section: Methodsmentioning

confidence: 99%

Mechanism Underlying the Reversal of Drug Resistance in P-Glycoprotein-Expressing Leukemia Cells by Pinoresinol and the Study of a Derivative

et al. 2017

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P-glycoprotein (P-gp) is a membrane protein associated with multidrug resistance (MDR) due to its key role in mediating the traffic of chemotherapeutic drugs outside cancer cells, leading to a cellular response that hinders efforts toward successful therapy. With the aim of finding agents that circumvent the MDR phenotype mediated by P-gp, 15 compounds isolated from native and naturalized plants of Argentina were screened. Among these, the non-cytotoxic lignan (±) pinoresinol successfully restored sensitivity to doxorubicin from 7 μM in the P-gp overexpressed human myelogenous leukemia cells, Lucena 1. This resistance-reversing effect was confirmed by competitively increasing the intracellular doxorubicin accumulation and by significantly inhibiting the efflux of doxorubicin and, to a lesser extent, that of rhodamine 123. The activity obtained was similar to that observed with verapamil. No such results were observed in the sensitive parental K562 cell line. To gain deeper insight into the mode of action of pinoresinol, its effect on P-gp function and expression was examined. The docking simulations indicated that the lignan bound to P-gp at the apex of the V-shaped transmembrane cavity, involving transmembrane helices 4, 5, and 6, and partially overlapped the binding region of tariquidar, which was used as a positive control. These results would shed some light on the nature of its interaction with P-gp at molecular level and merit further mechanistic and kinetic studies. In addition, it showed a maximum 29% activation of ATP hydrolysis and antagonized verapamil-stimulated ATPase activity with an IC50 of 20.9 μM. On the other hand, pinoresinol decreased the presence of P-gp in the cell surface. Derivatives of pinoresinol with improved activity were identified by docking studies. The most promising one, the non-cytotoxic 1-acetoxypinoresinol, caused a reversion of doxorubicin resistance from 0.11 μM and thus higher activity than the lead compound. It also caused a significant increase in doxorubicin accumulation. Results were similar to those observed with verapamil. The results obtained positioned these compounds as potential candidates for effective agents to overcome P-gp-mediated MDR, leading to better outcomes for leukemia chemotherapy.

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Plant growth inhibitory activities by secondary metabolites isolated from Latin American flora

Cited by 13 publications

References 63 publications

Evaluation of Antiparasitc Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone and Analogues against Trypanosoma brucei

Evaluation of Antiparasitc Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone and Analogues against Trypanosoma brucei

Bioactivity of essential oils from leaves and bark of Laurelia sempervirens and Drimys winteri against Acyrthosiphon pisum

Mechanism Underlying the Reversal of Drug Resistance in P-Glycoprotein-Expressing Leukemia Cells by Pinoresinol and the Study of a Derivative

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