The genus<i>Machaerium</i>(Fabaceae): taxonomy, phytochemistry, traditional uses and biological activities

Amen, Yhiya; Marzouk, Amani M.; Zaghloul, Mona G.; Afifi, Mohamed

doi:10.1080/14786419.2014.1003062

Cited by 17 publications

(16 citation statements)

References 31 publications

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“…It is a genus of shrubs or lianas and small to medium-sized trees occurring throughout Southern Mexico to Brazil and Northern Argentina and Peru. These species are indigenous to all climatic regions ranging from equatorial rainforests to the verges of dry and cold deserts [2][3][4]. Several species of this genus are used in traditional medicines are considered to have multiple medicinal properties.…”

Section: Introductionmentioning

confidence: 99%

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Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens

et al. 2020

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Two new epimeric bibenzylated monoterpenes machaerifurogerol (1a) and 5-epi-machaerifurogerol (1b), and four known isoflavonoids (+)-vestitol (2), 7-O-methylvestitol (3), (+)-medicarpin (4), and 3,8-dihydroxy-9-methoxypterocarpan (5) were isolated from Machaerium Pers. This plant was previously assigned as Machaerium multiflorum Spruce, from which machaeriols A-D (6–9) and machaeridiols A-C (10–12) were reported, and all were then re-isolated, except the minor compound 9, for a comprehensive antimicrobial activity evaluation. Structures of the isolated compounds were determined by full NMR and mass spectroscopic data. Among the isolated compounds, the mixture 10 + 11 was the most active with an MIC value of 1.25 μg/mL against methicillin-resistant Staphylococcus aureus (MRSA) strains BAA 1696, −1708, −1717, −33591, and vancomycin-resistant Enterococcus faecium (VRE 700221) and E. faecalis (VRE 51299) and vancomycin-sensitive E. faecalis (VSE 29212). Compounds 6–8 and 10–12 were found to be more potent against MRSA 1708, and 6, 11, and 12 against VRE 700221, than the drug control ciprofloxacin and vancomycin. A combination study using an in vitro Checkerboard method was carried out for machaeriols (7 or 8) and machaeridiols (11 or 12), which exhibited a strong synergistic activity of 12 + 8 (MIC 0.156 and 0.625 µg/mL), with >32- and >8-fold reduction of MIC’s, compared to 12, against MRSA 1708 and −1717, respectively. In the presence of sub-inhibitory concentrations on polymyxin B nonapeptide (PMBN), compounds 10 + 11, 11, 12, and 8 showed activity in the range of 0.5–8 µg/mL for two strains of Acinetobacter baumannii, 2–16 µg/mL against Pseudomonas aeruginosa PAO1, and 2 µg/mL against Escherichia coli NCTC 12923, but were inactive (MIC > 64 µg/mL) against the two isolates of Klebsiella pneumoniae.

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Section: Introductionmentioning

confidence: 99%

“…M. floribundum is used to treat diarrhea and menstrual cramps [4]. The presence of a wide array of secondary metabolites from Machaerium, including flavonoids, terpenoids, and oxygenated phenolic compounds, together with their bioactivities, was recently reviewed by Amen et al (2015) [2].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens

et al. 2020

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“…Components in natural samples may afford protection or repellent activity against insects either as a single component or in a synergistic manner 18 . Plants of the Machaerium genus (Fabaceae) comprise a Neotropical distribution of trees, shrubs and lianas native to southern Mexico, northern Argentina and Brazil 19 . Machaerium multiflorum showed antimalarial and antibacterial activities in a bioassay‐guided fractionation 20 .…”

Section: Introductionmentioning

confidence: 99%

Machaerium acutifolium compounds with larvicidal activity against Aedes aegypti

Melo

Sousa

Sá

et al. 2020

Pest Management Science

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BACKGROUND Plant extracts and isolated compounds are known for their insecticidal activity. The Aedes aegypti mosquito has a significant medical impact as it transmits a number of arboviruses and is able to develop resistance to the commercially available insecticides. This study investigates larvicidal compounds isolated from Machaerium acutifolium, designated by the Brazilian Forest Service as a sustainable species. RESULTS A M. acutifolium trunk ethyl acetate extract was fractionated using chromatographic methods with full structural elucidation by mass spectrometry (MS), nuclear magnetic resonance and specific rotation analyses revealing: one new 3‐arylcoumarin derivative 1; two flavonoids 2 and 3; a trans‐stilbene 4, and an unprecedented natural indene 5. The larvicidal activity against Ae. aegypti after 24 h exposure was: crude extract (median lethal dose, LC50 205 mg L–1), fraction C (LC50 27 mg L–1) and 5 (LC50 24 mg L–1). CONCLUSION A M. acutifolium extract showed larvicidal activity, which increased with prolonged exposure, demonstrating LC50 75 mg L–1 after 72 h. Although the flavonoids 2 and 3 and trans‐stilbene 4 were deemed inactive according to the adopted mortality limit, additional tests revealed their ability to cause 65% Ae. aegypti larvae mortality, suggesting they could contribute to the larvicidal activity. Compound 5, identified by liquid chromatography‐MS, was over eight‐fold more toxic to larvae than the crude extract after 24 h. Therefore, 5 constitutes a structural model for new prototypes to control Ae. aegypti. These data reinforce the potential of natural products as a source of commercial alternatives for vector control strategies, respecting both sustainability and eco‐friendly principles. © 2020 Society of Chemical Industry

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“…According to Leatemia and Isman (2004), the botanical families with the greatest insecticidal potential are Meliaceae, Rutaceae, Asteraceae, Annonaceae, Labiatae and Canellaceae. In addition to these families, Fabaceae have been mentioned for their insecticidal properties (Amen, Marzouk, Zaghloul, & Afifi, 2015;Santos, 2017;Souza et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

“…It is one of the largest genera of tropical trees in the world, and has approximately 130 species (Lewis, 2005). Various species from this genus have long been used pharmaceutically and are therefore known for their biological and medicinal action (Amen, Marzouk, Zaghloul, & Afifi, 2015). Machaerium opacum, popularly known as "Jacarandá-do-Cerrado" is an arboreal species native to Brazil, and it occurs throughout the Cerrado (savanna) regions of Brazil, including in some states in the North, Northeast, Southeast and, especially, the Midwest (Flora do Brasil, 2018).…”

Section: Introductionmentioning

confidence: 99%

Toxicity of Machaerium opacum (Fabaceae) Leaf Extracts Against Fall Armyworm (Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae)

Bezerra¹,

Santos²,

Menezes³

et al. 2019

JAS

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Secondary plant metabolites have been widely studied as pest control agents. In this paper we report secondary compounds present in Machaerium opacum leaves, as well as the toxicity of different fractions of the extract of this plant to fall armyworm (Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae)) under laboratory conditions. Crude extracts were obtained by means of ethanol. Refractionation was carried out with the solvents hexane, dichloromethane, methanol and ethyl acetate. By means of preliminary phytochemical prospection, starting with the ethanolic extract, flavonoid, triterpene, anthraquinone, coumarin, tannin and steroid compounds were identified. In the ethanolic fractions, triterpene compounds were identified in a mixture (α-amyrin and β-amyrin), as well as lupeol and the acyclic diterpene alcohol, phytol. In methanolic fractions, the flavonoid rutin was found. In the dichloromethane fraction, the flavonoid mucronulatol and its isomer, isomucronulatol, were found. Extracts of M. opacum did not present an antifeedant effect on the larvae of S. frugiperda. However, all fractions of the extracts tested promoted significant antibiosis effects (reduced weight in the larvae and pupa, larval and pupal mortality and prolongation of the adult phase) on the test population of S. frugiperda. Therefore, our results showed the insecticidal potential of leaf extracts of M. opacum against S. frugiperda.

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The genusMachaerium(Fabaceae): taxonomy, phytochemistry, traditional uses and biological activities

Cited by 17 publications

References 31 publications

Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens

Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens

Machaerium acutifolium compounds with larvicidal activity against Aedes aegypti

Toxicity of Machaerium opacum (Fabaceae) Leaf Extracts Against Fall Armyworm (Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae)

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