Antibacterial and antioxidant cassane diterpenoids from Caesalpinia benthamiana

Dickson, Rita A.; Houghton, Peter J.; Hylands, Peter J.

doi:10.1016/j.phytochem.2007.03.008

Cited by 96 publications

(32 citation statements)

References 8 publications

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“…and 1 mg mL À1 for fractions). The Petri plates spread with bacteria were incubated at 28°C for 24 h. A microdilution assay performed in 96-well microplate format was adopted for the determination of antibacterial activity against fish pathogenic bacterial of the pure compounds according to literature (Dickson, Houghton & Hylands 2007). Stock solutions (in dimethyl sulfoxide) of all compounds were serially diluted with sterile water to arrive designed concentrations.…”

Section: Determination Of Minimum Inhibitory Concentration (Mic) Agaimentioning

confidence: 99%

Bioassay-guided isolation and identification of active compounds fromMacleaya microcarpa(Maxim) Fedde against fish pathogenic bacteria

Kang

Zhang

et al. 2012

Aquac Res

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Four alkaloids (Sanguinarine, 6‐Methoxyl‐dihydro‐chelerythrine, Cryptopine and β‐Allocryptopine) were isolated from aerial parts of Macleaya microcarpa (Maxim) Fedde using bioassay‐guided isolation method, and the inhibitory activity of ethanolic extract, various fractions and these four alkaloids against four fish pathogenic bacteria (Aeromonas hydrophila, Aeromonas salmonicida, Vibrio anguillarum and Vibrio harveyi) was assessed in vitro using the agar dilution method and the microdilution assay method respectively. A. hydrophila was the most sensitive strain to all the tested compounds. Minimum inhibitory concentration (MIC) values were lower for sanguinarine against all tested Gram‐negative strains than other three alkaloids, with MIC values of 12.5 mg L−1 for A. hydrophila and 50 mg L−1 to other pathogenic bacteria. Followed by 6‐methoxyl‐dihydro‐chelerythrine, which showed considerable antibacterial activity with MIC values of 80 mg L−1 for A. hydrophila, 100 mg L−1 for V. harveyi, and 125 mg L−1 for both V. anguillarum and A. salmonicida. Cryptopine and β‐allocryptopine revealed similar inhibitory activity with MIC values of 100 mg L−1 for A. hydrophila and 200 mg L−1 for other three bacterial species. These finding provided evidence that extract, as well as isolated compounds from M. microcarpa might be potential sources novel antibacterial agents for the treatment of fish infectious diseases.

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Section: Determination Of Minimum Inhibitory Concentration (Mic) Agaimentioning

confidence: 99%

Bioassay-guided isolation and identification of active compounds fromMacleaya microcarpa(Maxim) Fedde against fish pathogenic bacteria

Kang

Zhang

et al. 2012

Aquac Res

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“…However, they found that it had no measurable antioxidant capacity (AOC), when measured by the Trolox equivalent antioxidant-capacity method (Re et al, 1999) which has been adapted to soils (Rimmer and Smith, 2009). Secondly, an antimicrobial effect is a possible reason for microbial inhibition as well, since in pharmaceutical studies microbial activity was inhibited by plant extracts rich in terpenoids (Popova et al, 2009;Dickson et al, 2007) and sterols (Smania et al, 2006;Bouhadjera et al, 2005). Several modes of action have been suggested: disruption of cell membranes and walls (Akinpelu et al, 2008;Lim et al, 2006), and the inactivation of membrane-bound proteins (Engels et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Effects of potentially inhibiting substances on C and net N mineralization of a sandy soil—a case study

Heumann

Rimmer

Schlichting

et al. 2013

J. Plant Nutr. Soil Sci.

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Recently, indirect evidence was obtained for inhibition of soil net N mineralization by sterols in soil organic matter, which could have been caused by their antioxidant or antimicrobial properties. The objective of this study was to test the effect of potential inhibitors (i.e., individual compounds with known antioxidant and/or antimicrobial properties) on soil microbial mineralization processes during incubation for 7 and 14 d. A sandy agricultural soil was amended with four substances: two phenolic acids differing in their antioxidant capacity (AOC) (acetovanillone with no AOC, ferulic acid with large AOC), Trolox, an analogue of vitamin E (large AOC), and b-sitosterol (no AOC, but potential antimicrobial properties). The two compounds with large AOC (ferulic acid and Trolox) showed no significant inhibition of C and net N mineralization; and the Trolox amendment actually caused a significant increase in C and net N mineralization after 7 d of incubation. Acetovanillone with no measurable AOC caused a significant increase in C mineralization (109% of substance C added), indicating degradation of the substance, and a very pronounced negative net N mineralization within 7 d (-356%), which was interpreted as N immobilization. Only b-sitosterol showed strong inhibition of net N mineralization after 7 and 14 d (-59% and -26%, respectively) which was not interpreted as N immobilization, since there was no concomitant increase in C mineralization. Thus, an antimicrobial effect of b-sitosterol specificly on microorganisms of the N cycle was suggested, but there was no clear inhibitory effect caused by the antioxidant compounds.

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“…6 Triterpenes, flavonoids and other compounds have been isolated from plants of the genus Caesalpinia sensu lato, 7,8 and 5-hydroxy-1,4-naphthoquinone has been isolated from the Asian species C. sappan . 9 The genus is also a rich source of cassane-type diterpenes, 10,11 which have been reported to have significant antimalarial, 12 antibacterial, 13 antihelmintic, 14 antiproliferative and antineoplasmic activities. 15,16 Caesalpinia is one of 21 genera included in the Caesalpinia group of legumes, 4 a group of genera that includes the East African and Madagascan monospecifc genus Stuhlmannia .…”

Section: Introductionmentioning

confidence: 99%

Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest

Liu

Harinantenaina

Brodie

et al. 2013

Bioorganic & Medicinal Chemistry

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Bioassay-directed fractionation of the leaf and root extracts of the antiproliferative Madagascar plant Stuhlmannia moavi afforded 6-acetyl-5,8-dihydroxy-2-methoxy-7-methyl-1,4-naphthoquinone (stuhlmoavin, 1) as the most active compound, with an IC50 value of 8.1 µM against the A2780 human ovarian cancer cell line, as well as the known homoisoflavonoid bonducellin (2) and the stilbenoids 3,4,5'-trihydroxy-3'-methoxy-trans-stilbene (3), piceatannol (4), resveratrol (5), rhapontigenin (6), and isorhapontigenin (7). The structure elucidation of all compounds was based on NMR and mass spectroscopic data, and the structure of 1 was confirmed by a single crystal X-ray analysis. Compounds 2–5 showed weak A2780 activities, with IC50 values of 10.6, 54.0, 41.0, and 74.0 µM, respectively. Compounds 1–3 also showed weak antimalarial activity against Plasmodium falciparum with IC50 values of 23, 26, and 27 µM, respectively.

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Antibacterial and antioxidant cassane diterpenoids from Caesalpinia benthamiana

Cited by 96 publications

References 8 publications

Bioassay-guided isolation and identification of active compounds fromMacleaya microcarpa(Maxim) Fedde against fish pathogenic bacteria

Bioassay-guided isolation and identification of active compounds fromMacleaya microcarpa(Maxim) Fedde against fish pathogenic bacteria

Effects of potentially inhibiting substances on C and net N mineralization of a sandy soil—a case study

Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest

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