Flavonoid Chemistry of the Leguminosae

Veitch, Nigel C.

doi:10.1002/9781444323375.ch2

Cited by 10 publications

(4 citation statements)

References 101 publications

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“…This chemical diversity stems mainly from the different (iso)flavonoid subclasses (21 known to date). (Iso)flavones, (iso)flavanones, isoflavans, pterocarpans, pterocarpenes, 3-arylcoumarins, and 2-arylbenzofurans are some of the main (iso)flavonoid subclasses encountered in Fabaceae 10 , 12 . Chemical diversity increases further by the presence of substituents other than the prenyl group (hydroxyl, methoxyl), as well as the different configuration that the prenyl group can have (chain, pyran or furan).…”

Section: Introductionmentioning

confidence: 99%

Insights into the molecular properties underlying antibacterial activity of prenylated (iso)flavonoids against MRSA

Kalli

Araya‐Cloutier

Hageman

et al. 2021

Sci Rep

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High resistance towards traditional antibiotics has urged the development of new, natural therapeutics against methicillin-resistant Staphylococcus aureus (MRSA). Prenylated (iso)flavonoids, present mainly in the Fabaceae, can serve as promising candidates. Herein, the anti-MRSA properties of 23 prenylated (iso)flavonoids were assessed in-vitro. The di-prenylated (iso)flavonoids, glabrol (flavanone) and 6,8-diprenyl genistein (isoflavone), together with the mono-prenylated, 4′-O-methyl glabridin (isoflavan), were the most active anti-MRSA compounds (Minimum Inhibitory Concentrations (MIC) ≤ 10 µg/mL, 30 µM). The in-house activity data was complemented with literature data to yield an extended, curated dataset of 67 molecules for the development of robust in-silico prediction models. A QSAR model having a good fit (R2adj 0.61), low average prediction errors and a good predictive power (Q2) for the training (4% and Q2LOO 0.57, respectively) and the test set (5% and Q2test 0.75, respectively) was obtained. Furthermore, the model predicted well the activity of an external validation set (on average 5% prediction errors), as well as the level of activity (low, moderate, high) of prenylated (iso)flavonoids against other Gram-positive bacteria. For the first time, the importance of formal charge, besides hydrophobic volume and hydrogen-bonding, in the anti-MRSA activity was highlighted, thereby suggesting potentially different modes of action of the different prenylated (iso)flavonoids.

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Section: Introductionmentioning

confidence: 99%

Insights into the molecular properties underlying antibacterial activity of prenylated (iso)flavonoids against MRSA

Kalli

Araya‐Cloutier

Hageman

et al. 2021

Sci Rep

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“…saponins, gums, pigments and biologically active alkaloids and lectins), so that comparative quantitative data are needed for more detailed analyses. The family is exceptionally rich in flavonoids (anthocyanins, flavones, flavonols, chalcones, flavanones, proanthocyanidins, isoflavonoids) and nitrogen-containing constituents (cyanogenic glycosides and non-protein amino acids, as well as quinolizidine, pyrrolizidine, indole and isoquinoline alkaloids), terpenoids (diterpene acids, triterpenoid saponins and tetraterpenoids), quinones (benzoquinones and anthraquinones), acetylenic compounds, furanocoumarins and xanthones (Harborne et al 1971;Kinghorn and Balandrin 1984;Southon 1994;Hegnauer and Hegnauer 1994, 1996, 2001Veitch 2010;Wink 2013).…”

Section: Other Traditional Usesmentioning

confidence: 99%

The diversity and multiple uses of southern African legumes

Wyk

2019

Aust. Syst. Bot.

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Southern Africa has a rich legume flora comprising 133 indigenous genera and 1620 indigenous species, of which 1059 species (65%) are endemic to the flora of southern Africa region. An additional 128 non-indigenous species have become naturalised, of which 59 are invasive, resulting in 1748 species from 165 genera. There are 22 (17%) endemic genera, one endemic tribe (Hypocalyptieae) and one near-endemic tribe (Podalyrieae, with 122 of the 123 species endemic). The diversity of uses (given as total/indigenous spp.) include food and beverages (127/115 spp.), medicine (338/291 spp.), magic and charms (113/104 spp.), timber (59/55 spp.), firewood (43/31 spp.) and 10 more minor use categories. Regression analyses showed that the levels of endemism in subfamilies and tribes are directly related to the numbers of species but that the number of useful species is not related to species numbers, except for the non-papilionoid subfamilies (all uses) and non-genistoid papilionoids (medicinal uses only). The Phaseoleae and Millettieae showed high residual values in several analyses, indicating that they have been favoured in the selection of useful plants. Diversity in habit and chemistry seems to explain at least partly the use patterns.

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“…Different types of soluble polyphenols, such as ferulic acid, gallic acid, or flavonoids, have been found to either stimulate or inhibit spore germination and hyphal growth of saprotrophic fungi. Plant mycorrhizal infection, nutrient uptake, and plant growth can be impaired by specific phenolics released by competitors in a process referred to as allelopathy [21].…”

Section: Total Phenolic Content (Tpc)mentioning

confidence: 99%

Purification and Identification of the Active Principles in Ethanol Extract Fractions of Phyllanthus Amarus Leaves

2022

ALST

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All organisms have their own antioxidant defense system that protects them against free radical damage by enzymes such as superoxide dismutase and catalase or compounds such as ascorbic acid, tocopherol and glutathione. However, our body system sometimes cannot work efficiently to mop up these free radicals thus, leading to unavoidable damages caused by oxidation. As a result, consumption of additional antioxidants through herbs such as Phyllanthus amarus, foods or supplements (phytochemicals) are beneficial to the body system, defending it against these harmful ROS. This research is aimed at ascertaining the presence of various antioxidants in ethanolic extract fractions of Phyllanthus amarus leaves. Phyllanthus amarus leaves were collected from Federal University Wukari premise, Taraba State, Nigeria and dried. The dried leaves were crushed into a fine powder manually using mortar and pestle. The ethanolic extract of Phyllanthus amarus leaves was placed under fan to evaporate the ethanol before subjecting it to further assays. The results obtained from this study revealed that for beta carotene inhibition assay, fraction 4b (445.9459%) with the solvent combination Chloroform:ethyl acetate (50:50) has the highest bleaching inhibition capacity while fraction 4a (81.08109%) has the lowest bleaching inhibition capacity. Fraction 2a (56.9565 mg/mL) has the highest phenolic content while fraction 6b (7.608669 mg/mL) has the lowest phenolic content. The assay for total flavonoid content showed that fraction 3a (145.71428 mg/mL) has the highest flavonoid content while fraction 8a (121.42857 mg/mL) has the lowest flavonoid content. The results for anti-lipid peroxidation increased with increasing extract concentration. Fraction 3b (55.732 mg/mL) with the solvent combination (chloroform 100:00) has the highest antioxidant capacity while fraction 6a (2.775 mg/mL) with the solvent combination of ethyl acetate: ethanol (50:50) has the lowest antioxidant activity. The correlation between total antioxidants capacity and total Phenolic content and that of antioxidant and flavonoid was found to be weak negative (r 2 =-2.058, r 2 =-0.024 respectively), while the correlation between phenolics and Betacarotene and that of the total antioxidant capacity and total flavonoid content was found to be weak positive (r 2 =0.245 and r 2 =0.313 respectively). The results of the analysis revealed that Phyllanthus amarus leaves contain significant nutritional components that are good for human health, such as flavonoids which is a subclass of the phytochemical, polyphenols. It is reasonable to conclude that fractions 2a and 2b has the highest antioxidant activities which have good potentials for drug development, especially against diseases of oxidative stress origin.

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Flavonoid Chemistry of the Leguminosae

Cited by 10 publications

References 101 publications

Insights into the molecular properties underlying antibacterial activity of prenylated (iso)flavonoids against MRSA

Insights into the molecular properties underlying antibacterial activity of prenylated (iso)flavonoids against MRSA

The diversity and multiple uses of southern African legumes

Purification and Identification of the Active Principles in Ethanol Extract Fractions of Phyllanthus Amarus Leaves

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