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Antibacterial activity of two limonoids from Swietenia mahagoni against multiple-drug-resistant (MDR) bacterial strains
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Solvent partitioning followed by column chromatography of the MeOH extract of the seeds of Swietenia mahagoni afforded two limonoids, swietenolide (1) and 2-hydroxy-3-O-tigloylswietenolide (2). The compounds were identified by spectroscopic means. The antibacterial activity of these compounds was assessed against eight multiple-drug-resistant bacterial strains (clinical isolates) by the conventional disc diffusion method. While both compounds were active against all test organisms, compound 2 displayed overall more potent activity than compound 1.
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... Over 60% of the commercially used medicines are either natural products or their derivatives [6,7]. Limonoids are natural products that exhibit various bioactivities, including antibacterial [8], antifungal [9], insect antifeedant [10], insecticidal [11], antimalarial [12], antioxidant [13], cytotoxic [14], anticancer [15], antiviral [16], and anti-inflammatory [17] properties. Borges et al. (2016) reported that gedunin, a limonoid from the Meliaceae family, exhibited immunomodulatory effect and multitarget properties in vitro and in vivo. ...
... As shown in Figure 2, compounds 3, 5, 11, 13, and 17 significantly inhibited SEAP release, which correlated with NF-κB activity inhibition (p < 0.01). (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) at a concentration of 20 µM, and LPS-stimulated (10 ng/mL) after 1 h. All data from four independent experiments are expressed as mean ± SD. ## p < 0.0001 vs. culture medium-only control group; ns: not significant, p > 0.1, *** p < 0.0001, vs. LPS stimulated-only group. ...
... Supplementary Materials: The following supporting information can be downloaded at: https://www. mdpi.com/article/10.3390/cimb46010058/s1, Figure S1: Agonist effects of 17 Limonoid compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) at a concentration of 20 µM on the NF-κB activation in HEK-Blue TM hTLR4 Cells. All data from four independent experiments are expressed as mean ± SD. ## p < 0.0001 vs. culture mediumonly control group; * p < 0.01, ** p < 0.001, *** p < 0.0001 vs. culture medium-only control group. ...
Chisocheton plants from the family Meliaceae have traditionally been used to treat several diseases; however, scientific evidence is limited. The most abundant chemical constituents of this plant are the limonoids, which are known for their various biological activities, including anti-inflammatory effects. However, the anti-inflammatory effects and underlying mechanisms of action of the constituents of Chisocheton plants have not been fully explored. In this report, we evaluated the anti-inflammatory activity of 17 limonoid compounds from Chisocheton plant primarily by measuring their inhibitory effects on the production of pro-inflammatory cytokines, including TNF-α, IL-6, IL-1β, and MCP-1, in LPS-stimulated THP-1 cells using an ELISA assay. Compounds 3, 5, 9, and 14-17 exhibited significant activity in inhibiting the evaluated pro-inflammatory markers, with IC 50 values less than 20 µM and a high selectivity index (SI) range. Compounds 3, 5, 9, and 15 significantly suppressed the expression of phosphorylated p38 MAPK in THP-1 cells stimulated with LPS. These findings support the use of limonoids from Chisocheton plants as promising candidates for anti-inflammatory therapy.
... Different components of the Mahagoni plant have been used in traditional medicine to treat a variety of conditions, including diabetes, malaria, amoebiasis, coughs, hypertension, tuberculosis and chest pain. It has also been used as an antiseptic, abortificient, depurative, astringent, and tonic [12]. ...
Biodegradable plastics (Bioplastic) with antimicrobial property has become new trend in packaging segment. In present market there has been limited availability biodegradable plastic with antimicrobial packaging, so there is huge potential in supply of such material. By keeping this scope in mind the current investigation was aimed to produce bioplastics using a simple and feasible casting method using starch, gelatine, agar, glycerol with varied concentrations. Subsequently the antimicrobial property, biodegradability, water and oil permeability were evaluated. The potential antimicrobial substance was extracted from Swietenia mahagoni and are found to be flavonoids which are responsible for imparting antimicrobial resistance property to the film. Further, the produced film was confirmed for its antimicrobial activity using plate assay method. Developed film showed resistance effect against airborne microbes. Then the film was also tested for biodegradability test through soil burial method which inferred that the film could be degraded in about 60 days. Collectively the data showed that the polymer film can be used as a prerequisite for development of bio plastics in food manufacturing industry especially packaged foods.
... 15 Mahogany roots, barks, seeds etc. have been used for the treatment of hypertension, diabetes, malaria, amoebiasis, coughs, chest pain and tuberculosis, and as an abortifacient, antiseptic, astringent, depurative, and tonic. 16 A recent study mentioned the potentiality of sky fruit seed extract as a tanning agent in the leather industry. 17 The synthesis of modified triterpenes known as limonoids, which contain a 4,4,8-trimethyl-17-furanyl steroid skeleton, distinguishes the mahogany (Meliaceae) family. ...
The curing of raw hides and skins using sodium chloride salt is a widely recognized technique, although it has negative consequences for the environment by elevating water salinity and introducing a significant amount of Total Dissolved Solids (TDS). In order to tackle this issue, goat skin was conserved through the utilization of a mixture consisting of crushed sky fruit seeds and sodium chloride salt. Various ratios of mixtures were applied to raw goat skin to determine an optimal outcome. The most favorable result was achieved by utilizing a blend of 10% seed crush and 10% salt, based on the weight of the raw skin. A control specimen was run with the experimental specimen, and preservation-related variables such as odor, hair loss, shrinkage temperature, moisture level, and bacterial population were evaluated. After preservation, the experimental sample and a control sample were subjected to the standard leather processing technique. The liquor from both samples was analyzed to confirm the impact of the environment on preservation. The experimental trial indicated a 59% decrease in total dissolved solids (TDS) and a 44% reduction in chloride (Cl−) content. The processed leather samples were assessed for their quality through an analysis of their physical properties. Besides, the fiber structures were assessed using a scanning electron microscope (SEM). The comparative evaluation of the physiochemical properties of the introduced preservation showed superb results with the hope of new preservation possibilities.
Moringa (Moringa oleifera Lam., Moringaceae), West Indian mahogany (Swietenia mahagoni [L.] Jacq., Meliaceae), and Cerasee (Momordica charantia L., Cucurbitaceae) are plants that are used for medicinal purposes in The Bahamas. They have various medicinal uses, including treating diabetes, anemia, inflammation, dermatological issues, backaches, cold, flu, and gastrointestinal problems. This review aims to summarize the current knowledge about natural products found in The Bahamas that can be used to treat diabetes mellitus. The search terms "Moringa oleifera Lam.," "Swietenia mahagoni (L.)," "Momordica charantia L.," "Tecoma stans," "Persea americana," "Psidium guajava," "Hamelia patens," and "Carica papaya L." in combination with "diabetes" were utilized to obtain pertinent data by searching PubMed and Google Scholar. Moringa oleifera Lam. significantly decreased fasting glucose levels in rodents after 3 months of consumption. The ethanolic extract of S. mahagoni seeds and the methanol extract of its bark can decrease blood glucose levels. Momordica charantia L. and H. patens Jacq. produce the same hypoglycemic effects as metformin. The plant extracts and compounds of T. stans (L.) Juss. ex Kunth, P. americana Mill., P. guajava L., and C. papaya L. showed diverse pharmacological activities such as reducing fasting glucose, lowering blood pressure and blood sugar, decreasing total triglycerides and total cholesterol, and improving structural damage of cardiac muscles caused by diabetes. Literature analysis reveals that the diverse pharmacological activities of various plants native to The Bahamas show promise as a medicinal food in the treatment of diabetes.
This study reports simultaneous isolation of three new limonoids (1–3), six known regio isomers (6, 7, 9–12), and three more known limonoids (4, 5, 8) from Swietenia macrophylla (S. macrophylla) seeds. Structures of these compounds were determined via extensive study of their 1D/2D-NMR and mass spectral data. Known limonoids (4–12) were identified by comparing their physical and spectroscopic data with literature values. A novel environmentally friendly supercritical fluid chromatography (SFC) technique facilitated simultaneous and rapid separation of these compounds. The pharmacological activities of the new limonoids were investigated.
Four new mexicanolide-type limonoids, swietemicrolides A–D (1–4), together with three known compounds (5–7) were isolated from an ethyl acetate extract of the bark of Swietenia microphylla. 1 and 2 had 1,8-hemiacetal systems whilst 3 and 4 shared hexacyclic skeletons consisting of three fused five-membered rings. The structures of the isolated compounds were determined using spectroscopic methods. The five limonoids (1–5) were tested in vitro for their cytotoxic effects against two human cancer cell lines (KB carcinoma and A549 lung cancer cells) and α-glucosidase inhibitory activity. None of them showed significant cytotoxic activity, however, swietemicrolide C (3) exhibited strong effect towards α-glucosidase. Moreover, a possible biosynthetic pathway for compounds 1–4 was proposed to support a comprehensive understanding of the configurations of the new limonoids.
Surface-active softening agents, such as Fatliquors, have a significant impact on the leather industry as they enhance the physicochemical properties of leather. This study focuses on analyzing the synthesis, properties, characterization, and sulfonation of Swietenia mahagoni seed oil to determine its potential as a fatliquoring agent for leather. An investigation was conducted to verify the alteration of Swietenia mahagoni oil through the analysis of its properties before and after the sulfonation process. A scientific analysis was carried on the oil using GC-FID, revealing the presence of various unsaturated fatty acids such as linoleic, linolenic, oleic, palmitic, and arachidic acids. This demonstrates the sulfonating capability of this sky fruit seed oil. A fatliquor was created by sulfonating the oil, and the sulfonation was verified through Fourier Transform Infrared Spectroscopy (FTIR) and ¹H Nuclear Magnetic Resonance (NMR) spectra. The prominent peak observed at 1209 cm-1 in the FTIR spectra indicated the stretching of S=O in both sulfate and sulfonate groups. The newly formed protons (H–C–S or H–C–O) showed signals between δ 4.09 and 4.29 ppm in the ¹H NMR spectra, confirming the sulfonation of the fatliquor that was prepared. Moreover, the change in the melting point of sulfonated Mahogany oil from 40.8 °C to 48.1 °C suggests increased saturation levels. The fatliquor's emulsion stability was found to be at a satisfactory level. After conducting tests on the treated leather, the physical strength and morphological structure was analyzed using Field Emission Scanning Electron Microscopy (FE-SEM), the fatliquor improved the lubrication and strengthened the fibrous network structure of the leather, composed of thin and tight collagen fibers. The BOD5/COD ratio of the effluent from the experimental trial was determined to be 0.52, suggesting that the fatliquor developed is a biodegradable product. Finally, the antifungal capabilities of the fatliquor-treated leather were tested against four different fungus species: Aspergillus niger, Aspergillus flavus, Penicillium notatum, and Candida albicans, and the treated leather sample shown favorable antifungal activity.
Swietenia macrophylla King in Hook (SM) is known to have several medicinal properties. Chloroform extracts of SM seeds (SMCE) as well as two isolated limonoids swietenine (1) and swietenolide (2) showed significant in vitro anti-CRC activity in human colon carcinoma (HCT116) cell line. 2 (IC50 = 5.6 µM) was found to be two times more potent than 1 (IC50 = 10 µM). Both compounds showed anti-CRC activity through inhibition of the Mouse Double Minute 2 homolog (MDM2) of the MDM2-p53 pathway. The Selectivity Index (S.I.) of isolated compounds 1 and 2 for cancer cells were about 6.6 and 12.8 fold respectively which was significantly better than the S.I. of the extract (S.I. ∼1.5).
Phragmalin-type limonoids are highly complex natural products based on an unusual octahydro-1H-2,4-methanoindene cage. The absence of feasible routes to sufficiently functionalized methanoindene cage building blocks impedes the total synthesis of these natural products. We have developed a short and robust route to methanoindene cage compounds from the Hajos-Parrish ketone (HPK). Several stereoselective modifications of the HPK provided a substrate that underwent aldol reaction as a key step for the cage formation.
The petroleum ether, ethyl acetate, and methanol extracts of Phyllanthus reticulatus. Poir. (Euphorbiaceae) were chosen for pharmacological screening. In the acetic acid-induced writhing test, the ethyl acetate extract in doses of 150 and 300 mg/kg showed 51.23 and 65.12% inhibition of writhing, respectively. A significant elongation of tail-flick time was evident both in the ethyl acetate and the methanol extracts (42.38 and 60.49%) only at the 300 mg/kg dose level. In carrageenan-induced rat paw edema model, the methanol extract at the 300 mg/kg dose level showed 40.03% inhibition of edema at the end of 4 h. These results demonstrated that the extracts of P. reticulatus. possess significant analgesic and anti-inflammatory properties.
Aim: To search the peroxisome proliferator-activated receptor gamma (PPARgamma) agonists from Swietenia mahagony extract (SmE) and observe the possible ameliorative effects of SmE on diabetic db/db mice. Methods: The PPARgamma agonistic activity of SmE was screened by yeast-two hybrid system. The blood glucose levels of diabetic db/db mice were measured using a blood glucose level monitor and the data were statistically analyzed by NDST8.8W software. Results: By using the clinical drug rosiglitazone as a positive control, it was found that the PPARgamma agonistic activity of SmE at a concentration of 50 mug/L was approximately half that of 35.7 mug/L (0.1 mumol/L) of rosiglitazone. At the dose of 1000 mg/kg, SmE remarkably decreased the blood glucose concentration of db/db mice from (15.26 +/- 2.98) to (7.58 +/- 2.20) mmol/L, and reduced the blood glucose levels by 55.49% compared with the control group (P<0.01). Conclusion: SmE shows agonistic activity to PPARgamma and can ameliorate the blood glucose levels of diabetic db/db mice. SmE may be thus used as a potential agent for diabetes therapy.
Eighteen new tetranortriterpenoids were isolated from the cotyledons of Swietenia mahagoni (Meliaceae) along with ten known tetranortriterpenoids. Among them, the structures of eight new compounds, swietenins B, C, D, E, and F, 3-O-acetylswietenolide, 6-O-acetylswietenolide, and 3-O-tigloyl-6-O-acetylswietenolide, were determined by the use of two-dimensional nuclear magnetic resonance (2D NMR) techniques. Detailed analyses of the 1H- and 13C-NMR spectra of the ten known compounds were also performed.
For the purpose of finding anti-HIV agents from natural sources, various plant extracts were screened for their inhibitory activity against HIV-protease, an enzyme essential for viral proliferation. By bioassay-directed fractionation of the methanol extract of Swietenia mahagoni (bark) which had shown inhibitory activity against this enzyme, we isolated and identified chlorogenic acid methyl ester as a inhibitory substance, its 50% inhibitory concentration being less than 40 μg/ml. © 1997 John Wiley & Sons, Ltd.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Two novel limonoids, swiemahogins A (1) and B (2) isolated from the twigs and leaves of Swietenia mahogany, are the first examples of andirobin and phragmalin types of limonoids, of which the D-ring δ-lactone is demolished and a rare γ-lactone is fused to the C-ring at C-8 and C-14. Their structures were elucidated by extensive spectroscopic means, and that of 1 was confirmed by single-crystal X-ray diffraction.
A salicylic acid derivative (1), a cinnamaldehyde (2), and six isoflavones (3–8) from the stem bark of Flemingia paniculata. Wall. (Leguminosae) were tested for antibacterial (both Gram-positive and Gram-negative) and antifungal activities. All the compounds showed significant activities against the test organisms having MIC values in the range of 1.57–200 μ g/mL. The highest potency (MIC = 1.57 μ g/mL) was exhibited by 3 against Staphylococcus aureus..
A new mexicanolide-type limonoid, 2-hydroxy-3-O-tigloyl-6-O-acetylswietenolide [1], and a new tirucallane-type triterpenoid derivative, lipo-3-episapelin A [2], were isolated from pericarps of Trichilia connaroides and their structures established on the basis of chemical and spectral evidence. In addition, five known tirucallane-type triterpenoids were also isolated.
Of 30 Indonesian plant extracts tested for their human immunodeficiency virus type-1 (HIV-1) inhibitory activities, six were shown to be effective by assays using HIV-1-infected MT-4 cells: a methanol extract of mahoni (bark of Swietenia mahagoni) and water extracts of benalu teh (stems and branches of Loranthus parasiticus), kiules (fruit of Helicteres isora), supratul (fruits of Sindora sumatrana), sambiloto (leaves of Andrographis paniculata) and temu ireng (rhizoma of Curcuma aeruginosa). Their ED50 values ranged from 4.2 to 175 μg/mL. The samples also suppressed the formation of syncytia in co-cultures of MOLT-4 and MOLT-4/HIV-1 cells. The most potent inhibitor was a methanol extract of mahoni, which also showed a significant inhibition of HIV-1 protease.
Three new sesquiterpenes, 6-hydroxy-7-(1-methylethyl)-3,3a,6,7,8,8a- hexahydroazulene-1,4-dicarboxylic acid methyl ester (1, named viscozulenic acid methyl ester), 7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid 1-methyl ester (2, named viscoazucinic acid) and 3-oxo-1-epi-sclerosporin (3, named polygosumic acid), have been isolated from the chloroform extract of the aerial parts of Polygonum viscosum by reversed-phase preparative high performance liquid chromatography (HPLC). The structures of these compounds were established conclusively by ultraviolet (UV), mass spectrometry (MS) and a series of 1D and 2D nuclear magnetic resonance (NMR) analyses. The anti-bacterial properties of 1-3 against 12 pathogenic bacterial strains have also been assessed by the rapid and robust microtitre-plate-based serial dilution method incorporating resazurin as an indicator of cell growth. Polygosumic acid was the most active among the sesquiterpenes and inhibited the growth of penicillin-resistant Escherichia coli (minimum inhibitory concentration, MIC=0.05 mg/ml) and methicillin-resistant Staphylococcus aureus (MRSA) (MIC=0.10 mg/ml).