Comparative study of the antidiabetic potential of Paederia foetida twig extracts and compounds from two different locations in Malaysia

Context: Paederia foetida L. (Rubiaceae) is an edible plant distributed in Asian countries including Malaysia. Fresh leaves have been traditionally used as a remedy for indigestion and diarrhea. Several phytochemical studies of the leaves have been documented, but there are few reports on twigs. Objective: This study investigates the enzyme inhibition of P. foetida twig extracts and compound isolated from them. In addition, in silico molecular docking of scopoletin was investigated. Materials and methods: Plants were obtained from two locations in Malaysia, Johor (PFJ) and Pahang (PFP). Hexane, chloroform and methanol extracts along with isolated compound (scopoletin) were evaluated for their enzyme inhibition activities (10,000-0.000016 µg/mL). The separation and identification of bio-active compounds were carried out using column chromatography and spectroscopic techniques, respectively. In silico molecular docking of scopoletin with receptors (α-amylase and α-glucosidase) was carried out using AutoDock 4.2. Results: The IC50 values of α-amylase and α-glucosidase inhibition activity of PFJ chloroform extract were 9.60 and 245.6 µg/mL, respectively. PFP chloroform extract exhibited α-amylase and α-glucosidase inhibition activity (IC50 = 14.83 and 257.2 µg/mL, respectively). The α-amylase and α-glucosidase inhibitory activity of scopoletin from both locations had IC50 values of 0.052 and 0.057 µM, respectively. Discussion and conclusions: Separation of PFJ chloroform extract afforded scopoletin (1), stigmasterol (2) and γ-sitosterol (3) and the PFP chloroform extract yielded (1), (2), (3) and ergost-5-en-3-ol (4). Scopoletin was isolated from this species for the first time. In silico calculations gave a binding energy between scopoletin and α-amylase of -6.03 kcal/mol

Isolation and characterization of antioxidative and cytotoxic phytoconstituents from Aegle marmelos (L.) Correa and Murraya koenigii (L.) Spreng. and their in silico study

Rutaceae family includes Aegle marmelos and Murraya koenigii had been used as medicinal plants since ancient to treat fever, snake bites, diarrhoea and stomachache. However, scientific validation of medicinal properties on Aegle marmelos and Murraya koenigii are still limited. In this research, two Rutaceae plants namely Murraya koenigii (curry leaves tree) and Aegle marmelos (majapahit) were selected for the investigation of their phytochemicals, antioxidant and cytotoxicity properties. The mechanism of cytotoxic will be evaluated by in silico docking study. The isolation of phytoconstituents from Aegle marmelos yielded aegeline (7), two coumarins: marmin (33) and 7-hydroxycoumarin or umbelliferone (36) together with two triterpenoids : β-sitosterol (55) and epi-lupeol (31). Meanwhile, phytochemical constituents isolated from Murraya koenigii afforded four alkaloids including girinimbine (1), mahanimbine (45), murrayanine (49), murrayacine (44) and β- sitosterol (55). The chloroform extract of Murraya koenigii stem bark showed the highest antioxidant activity in CUPRAC (1490.89 mgTE/g extract). Mahanimbine (45) was the most active compound with the activity of 927.73 mgTE/g, and 1649.31 mgTE/g based on ABTS and CUPRAC assays respectively. It also showed lipid peroxidation inhibition with the percentage of 70.95%. The CUPRAC and ABTS results are the first report for Malaysian Murraya koenigii species. Cytotoxicity study revealed that the chloroform root extract of Murraya koenigii showed the most active (IC50: 11.26 ± 0.74 μg/mL) against MDA-MB-231, whilst, hexane root extract of Murraya koenigii show the most cytotoxic against MCF-7 (IC50:15.13 ± 2.37 μg/mL). Girinimbine (1) and mahanimbine (45) were found to exhibit potent cytotoxic activities toward MCF-7 with the IC50 values of 11.95 ± 3.63 μg/mL and 11.01 ± 0.48 μg/mL respectively. Girinimbine (1) also exhibited the most significant cell growth inhibition against MDA-MB-231, followed by mahanimbine (45) with IC50 of 8.92 ± 0.03 μg/mL and 12.41 ± 0.61 μg/mL, respectively. Cell death morphology studies revealed that both breast cancer cell lines treated with girinimbine (1) and mahanimbine (45) showed apoptotic characteristics such as cell shrinkage, nuclear condensation and membrane blebbing. Both girinimbine (1) and mahanimbine (45) were non-cytotoxic in the MTT cytotoxic screening against 3T3 cell lines (IC50> 30 μg/mL). The in silico docking studies of girinimbine (1), mahanimbine (45), murrayanine (49) and murrayacine (44) revealed that mahanimbine (45) showed the highest binding energy with the values of -9.31 and -9.30 kcal/mol towards p38α MAPK and hER-α receptors respectively. Meanwhile, docking of girinimbine (1) with p38α MAPK and hER-α receptors produced the binding energies of -8.60 and -8.83 kcal/mol respectively. The binding of both girinimbine (1) and mahanimbine (45) showed mutual interactions with the amino acids that responsible for the p38α MAP kinase inhibition. The hydrophobic interaction involved protein residues of Leu167, Lys53, Val30 and Val38. Meanwhile, the binding of girinimbine (1) and mahanimbine (45) showed anti-estrogen properties through the hydrophobic interaction with the amino acids such as Arg394, Glu353, Met421, Leu525, Ala350, Leu387, Leu349 and Leu391. The in silico studies of girinimbine (1) and mahanimbine (45) with p38α MAPK and hER-α were firstly reported. The in silico studies revealed that girinimbine (1) and mahanimbine (45) could be the potent drug nuclei as an anti-estrogen agent in the treatment of ER+ breast cancer and p38α MAP kinase inhibitor. The results suggested that girinimbine (1) and mahanimbine (45) which was isolated from Murraya koenigii could be potential candidates for breast cancer treatment and therapy

Isolation of carbazole alkaloids and coumarins from Aegle marmelos and Murraya koenigii and their antioxidant properties

In this paper, antioxidant properties of Aegle marmelos (stem bark, leaves) and Murraya koenigii (stem bark, root) were evaluated by 2,2-diphenyl-1-picrylhydrazy (DPPH) free radical scavenging, 2,2’-Azino-bis(3-ethylbenzthiozoline-6-sulfonic acid) (ABTS) decolourisation, cupric reducing antioxidant capacity (CUPRAC), ferric reducing antioxidant power (FRAP) and linoleic acid/β-carotene assays. The chloroform extract of Murraya koenigii stem bark was found to possess the highest antioxidant activity in CUPRAC (1490.89 mgTE/g extract). In contrary, the hexane extract from Aegle marmelos leaves exhibited the weakest antioxidant activity in the DPPH assay (81.06 mgTE/g extract). The bioactive compound mahanimbine (7) isolated from the stem bark of Murraya koenigii was found to be the most active antioxidant agent with TEAC of 927.73 and 1649.31 mgTE/g corresponding to the ABTS and CUPRAC assays, respectively, as well as a good lipid peroxidation inhibitor with an inhibitory percentage of 70.95%. These CUPRAC and ABTS assays are the first report for Malaysian Murraya koenigii species

Antioxidant properties of ginger (<i>Kaempferia angustifolia</i> Rosc.) and its chemical markers

<p>The nutritional value of the rhizomes of <i>Kaempferia angustifolia</i> was measured through the antioxidant properties of various extracts and the determination of the bioactive compounds. The chloroform and methanol extracts of the rhizomes of <i>Kaempferia angustifolia</i> showed strong free radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with values of 615.92 mg Trolox equivalent (TE)/g each. The methanol extract also exhibited the strongest antioxidant properties in the azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) assay with a value of 38.87 mg TE/g. The hexane extract gave the strongest reducing ability in cupric reducing antioxidant capacity (CUPRAC) assay with a value of 901.76 mg TE/g, whilst the ethyl acetate extract exhibited the strongest reducing ability against ferric reducing antioxidant power (FRAP) with a value of 342.23 mg TE/g. Column chromatographic separation on the rhizomes of <i>Kaempferia angustifolia</i> afforded boesenboxide (<b>1</b>), crotepoxide (<b>2</b>), 2ˊ-hydroxy-4,4ˊ,6ˊ-trimethoxychalcone (<b>3</b>), kaempfolienol (<b>4</b>), and zeylenol (<b>5</b>), which were elucidated by spectroscopic methods. Kaempfolienol (<b>4</b>) was the strongest free radical agent against DPPH with a value of 443.92 mg TE/g, whilst 2ˊ-hydroxy-4,4ˊ,6ˊ-trimethoxychalcone (<b>3</b>) exhibited the strongest antioxidant properties with values of 42.23, 1497.22, and 781.53 mg TE/g against ABTS, CUPRAC, and FRAP assays, respectively.</p