This manuscript describes the first detailed chemical investigation of endemic species Iris adriatica, including isolation and structure elucidation. Chemical analyses of the rhizome CH2Cl2/MeOH (2:1) extract revealed fourteen secondary metabolites, mainly isoflavonoids. Among isoflavonoids, two groups have been found: nigricin-type and tectorigenin-type. Dominant group of the isolated compounds has been nigricin-type isoflavones: nigricin, nigricin-4'-(1-O-β-D-glucopyranoside) and nigricin-4'-(1-O-β-D-glucopyranosyl (1-6)-β-D-glucopyranoside) with 2.5, 10 and 1% of the total extract, respectively. Irisxanthone - xanthone C-glucoside, β-sitosterol, benzophenone and one of its derivatives have also been found. Nigricin-type isoflavonoids and irisxanthone can be considered as possible chemotaxonomic markers for I. adriatica. 5,3',5'-Trimethoxy-6,7-methylenedioxyisoflavone-4'-(1-O-β-D-glucopyranoside) and benzophenone have been isolated from Iris species for the first time.
The Bornean liverwort Gottschelia schizopleura was investigated phytochemically for the first time. Two new and four previously known clerodane-type diterpenoids were isolated from the MeOH extract of G. schizopleura through a series of chromatographic techniques. The structures of the new metabolites were established by analyses of their spectroscopic data (1D NMR, 2D NMR, HRESIMS and IR). All the isolated compounds 1-6 were tested against human promyelocytic leukaemia (HL-60), human colon adenocarcinoma (HT-29) and Mus musculus skin melanoma (B16-F10). Compound 1 and 2 showed active inhibition against HL-60 and B16-F10 cells.
One new compound, 12-epi-9-deacetoxyxenicin (1) along with a hydroperoxide product, 12-epi-9-deacetoxy-8-hydroperoxyxenicin (2) and two known sesquiterpenoids (3-4) were isolated from a population of Bornean soft coral Xenia sp. The structures of these secondary metabolites were elucidated based on their spectroscopic data. Compounds 1 and 2 showed cytotoxic activity against ATL cell line, S1T. In addition, compound 3 exhibited hyphal inhibition of Lagenidium thermophilum.
Dysregulation of matrix metalloproteinases (MMPs) activity is known in many pathological conditions with which most of the conditions are related to elevate MMPs activities. Ficus deltoidea (FD) is a plant known for its therapeutic properties. In order to evaluate the therapeutic potential of FD leaf extract, we study the enzymatic inhibition properties of FD leaf extract and its major bioactive compounds (vitexin and isovitexin) on a panel of MMPs (MMP-2, MMP-8 and MMP-9) using experimental and computational approaches. FD leaf extract and its major bioactive compounds showed pronounced inhibition activity towards the MMPs tested. Computational docking analysis revealed that vitexin and isovitexin bind to the active site of the three tested MMPs. We also evaluated the cytotoxicity and cell migration inhibition activity of FD leaf extract in the endothelial EA.hy 926 cell line. Conclusively, this study provided additional information on the potential of FD leaf extract for therapeutical application.
The bioactivity guided fractionation of Tetracera indica leaves crude ethanolic extract has afforded the isolation and characterization of six compounds including a new natural product viz., 5,7-dihydroxyflavone-O-8-sulphate (1) and five known flavonoids (2-6). The structures of the compounds were elucidated using 1D and 2D NMR and HRESIMS spectroscopic analyses. All the isolated compounds were evaluated for their in vitro inhibitory activity against alpha-glucosidase. Compound 1, 5 and 6 showed strong alpha-glucosidase inhibitory activity, 3 and 4 displayed weak activity while compound 2 was inactive. The interactions of the active compounds with alpha-glucosidase were further investigated using molecular docking to confirm their antidiabetic potential.
Chalcones are a group of compounds widely distributed in plant kingdom. The aim of this study was to assess the neurite outgrowth stimulatory activity of selected chalcones, namely helichrysetin, xanthohumol and flavokawin-C. Using adherent rat pheochromocytoma (PC12 Adh) cells, the chalcones were subjected to neurite outgrowth assay and the extracellular nerve growth factor (NGF) levels were determined. Xanthohumol (10 μg/mL) displayed the highest (p
A phytochemical study carried out on the plant, Calophyllum wallichianum has led to the isolation of a new coumarin, wallimarin T (1) and a known coumarin, calanolide E (2) along with two common triterpenes, friedelin (3) and stigmasterol (4). The structures of these compounds were elucidated with the aid of spectroscopic analyses such as FT-IR, GC-MS, and NMR. MIC assay against the Bacillus bacteria were conducted on the extracts and this gave MIC values ranging from 0.313 to 1.25 mg/mL. Compound 2 was weakly inhibitory towards the Bacilli strains with MIC values ranging from 0.25-0.50 mg/mL. Wallimarin T (1) was not active towards all four bacteria. Overall, the extracts exhibited weak bactericidal properties whereas compound 2 was not bactericidal on the tested bacteria. The hexane and chloroform extracts of the plant were found to be inhibitors to the growth of Bacillus megaterium, Bacillus cereus, Bacillus pumilus and Bacillus subtilis.
A new limonoid, pentandricine (1), along with three known limonoids, ceramicine B (2), 6-de(acetyloxy)-23-oxochisocheton (3), 6-de(acetyloxy)-23-oxo-7-O-deacetylchisocheton (4), have been isolated from the stembark of Chisocheton pentandrus. The chemical structures of the new compound were elucidated on the basis of spectroscopic evidence. All of the compounds were tested for their cytotoxic effects against MCF-7 breast cancer cells. Compounds 1-4 showed weak and no cytotoxicity against MCF-7 breast cancer cells with IC50 values of 369.84, 150.86, 208.93 and 120.09 μM, respectively.
The aim of the study was to isolate digestive enzymes inhibitors from Mimosa pudica through a bioassay-guided fractionation approach. Repeated silica gel and sephadex LH 20 column chromatographies of bioactive fractions afforded stigmasterol, quercetin and avicularin as digestive enzymes inhibitors whose IC50 values as compared to acarbose (351.02 ± 1.46 μg mL-1) were found to be as 91.08 ± 1.54, 75.16 ± 0.92 and 481.7 ± 0.703 μg mL-1, respectively. In conclusion, M. pudica could be a good and safe source of digestive enzymes inhibitors for the management of diabetes in future.
Four new bicyclogermacrenes, capgermacrenes D (1) E (2) F (3) and G (4) were isolated from a population of Bornean soft coral Capnella imbricata. The structures of these metabolites were elucidated based on their nuclear magnetic resonance and high-resolution electrospray ionisation mass spectrometry spectral data. These compounds showed bacteriastatic and bacteriacidal activities against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus.
In this study the antioxidant and cytotoxicity activity of the Adonidia merrillii fruits were investigated using different solvent polarities (methanol, ethyl acetate and water). The results showed that the total phenolic and flavonoid contents of the methanolic extract was higher compare with other extract with respective values of 17.80 ± 0.45 mg gallic acid equivalents/g dry weight (DW) and 5.43 ± 0.33 mg rutin equivalents/g DW. Beside that The RP-HPLC analyses indicated the presence of gallic acid, pyrogallol, caffeic acid, vanillic acid, syringic acid, naringin and rutin. In the DPPH, NO2 and ABTS scavenging assays, the methanolic extract exhibited higher antioxidant activity as compared to the ethyl acetate and water extracts. The extracts exhibited moderate to weak cytotoxic activity in the assays using human hepatocytes (Chang liver cells) and NIH/3T3 (fibroblasts cell) cell lines. The findings showed the Adonidia merrillii fruit extracts to possess considerable antioxidant and cytotoxicity properties. The fruit, therefore, is a potential candidate for further work to discover antioxidant and cytotoxic drugs from natural sources.
In the present research, oleuropein (OLE) contents from two Saudi Arabian wild olive trees (Olea europaea L.) leaves (O1 and O2), were collected from two nearby geographical sites differing in altitudes, and were determined via UHPLC-MS analysis. Moreover, total bioactive contents, antioxidant, and cytotoxicity (against MCF-7 and MDA-MB-231 cells) potential were also evaluated. The sample (O2) was found to contain significantly (p
Liquid Chromatography-Mass Spectrometry (LC-MS) analysis of methanol extract of Martynia annua seed revealed the presence of haploperozide and austricine. For safety, heavy metals content investigation of plant powder using the Inductively Coupled Plasma-Mass Spectrometry (ICP-MS) technique showed that the toxic metals (Pb: 2.07 mg/kg; Cd: 0.07 mg/kg; and As: 0.18 mg/kg) concentrations were found to be below the permissible limit. The extract demonstrated significant antibacterial activity against E. coli (MIC value 125 g/mL). Furthermore, it was effective in inhibiting both α-glucosidase and α-amylase enzymes with a high percentage and IC50 values were 42.28 ± 0.39 µg/mL and 34.11 ± 0.31 µg/mL, respectively. These findings were supported by a molecular docking study, some of the phytochemicals showed higher docking score values than references. However, Martynia annua seeds are safe to consume because they contain low levels of toxic heavy metals and possess antibacterial and anti-diabetic properties.
Biotransformation is acknowledged as one of the green chemistry methods to synthesis various analogues for further valorization of natural product compounds chemistry and bioactivities. It has huge advantage over chemical synthesis due to its cost-efficiency and higher selectivity. In this work, a xanthorrhizol derivatives, namely (7 R,10S)-10,11-dihydro-10,11-dihydroxyxanthorrhizol was produced in 60% yield from the biotransformation process utilizing A. niger. The structure of the compound was established by extensive spectroscopic methods and comparison with literature data. This biotransformation successfully afforded enantioselective dihydroxylation reaction via green chemistry route. This is the first report on both biotransformation of xanthorrhizol and utilization of A. niger as its biocatalyst.
Extracts from Selenicereus monacanthus (synonym: Hylocereus polyrhizus) have received attention due to their potent anti-inflammatory, antioxidant, anticancer, and antidiabetic properties. The current study aims to determine the anti-inflammatory and wound-healing potential of defatted S. monacanthus seed extract (DSMSE). Anti-inflammatory properties of DSMSE on LPS-induced inflammation on THP-1 were determined by measuring the levels of interleukins IL-6, IL-8, and IL-10. Wound healing scratch assay was performed using the human fibroblast (Hs27) cell that assesses the cell migration over 24 h exposure to DSMSE. Administration of DSMSE significantly reduced the LPS-stimulated release levels of IL-6 and IL-8 and significantly increased the levels of IL-10. Treatment with DSMSE showed a significant increase in wound closure with 70% of fibroblast migration. Therefore, the current study showed the anti-inflammatory and wound healing properties of DSMSE reducing inflammatory cytokines (IL-6 and IL-8), increasing IL-10 cytokine, and increasing wound closure at 24 h.
This study was designed to investigate the chemical composition of the essential oil of Syzygium variolosum (King) Chantar. & J.Parn. and their cytotoxicity, acetylcholinesterase, antityrosinase, and anti-inflammatory activities. In total, 32 chemical components were identified in the essential oil, which made up 98.9%. The essential oil is mainly composed of β-elemene (20.2%), bicyclogermacrene (13.5%), viridiflorol (11.1%), globulol (8.6%), and selin-11-en-4α-ol (5.3%). Acetylcholinesterase, antityrosinase, and anti-inflammatory activities were evaluated with the Ellman method, mushroom tyrosinase, and lipoxygenase enzymes, respectively, while cytotoxicity was assessed using an MTT assay. The results showed that essential oil gave significant percentage inhibition (I%: acetylcholinesterase 35.2%, antityrosinase 42.5%, lipoxygenase 48.6%). Furthermore, the essential oil exhibited cytotoxicity against three cancer cell lines, HepG2, MCF7, and A549, with IC50 values ranging from 90.2 to 95.2 μg/mL. The current study highlights the potential of the use of essential oils as an alternative to the development of pharmaceutical antichemopreventives or cosmetics.
Phytochemical investigation through cytotoxicity bioassay-guided isolation of Geniotrigona thoracica propolis led to the identification of five cycloartane-type triterpenes, including mangiferonic acid 1, ambonic acid 2, mangiferolic acid 3, ambolic acid 4 and cycloartenol 5. Their structures were established based on detailed spectroscopic analysis and comparison with literature data. Compounds 1-5 were isolated for the first time in this species. From cytotoxicity MTT assay, compound 3 inhibited the growth of breast (MCF-7) and hepatocellular carcinoma (HepG2) cancer cell lines with IC50 of 5.08 and 4.82 µg/mL, respectively. Cytotoxicity of compounds 1-5 were reported for the first time against HepG2 cancer cell lines. Compounds 1-4 were suggested to serve as main and/or analytical markers for G. thoracica propolis based on HPLC analysis. To our knowledge, this is the first report on the isolation of bioactive constituents and identification of chemical markers for G. thoracica propolis.
The pantropical Physalis minima are traditionally used for the prevention and treatment of various illnesses, diseases, and cancers. While most earlier studies on the species have focused on the phytochemistry of the leaf and stem extracts, recent studies have indicated that its fruit may contain bioactive compounds of medical interest. In this study, we investigated the cytotoxicity of extracts from the fruit of P. minima against colorectal cancer cell lines and revealed its phytochemical profile via high-resolution tandem mass spectrometry analysis. Following a 24-h treatment with the fruit extract, cytoplasm shrinkage and nucleus condensation were observed in the colorectal cancer cell lines HCT116 and HT29, indicating the induction of programmed cell death. Phytochemically, 71 putative metabolites were identified. Some of these metabolites have been reported to inhibit cancers to varying degrees, further supporting the correlation of the putative metabolites with the cytotoxicity against colorectal cancer cells demonstrated in this study.
The Short Communication "In vitro & in silico study of hypoglycemic potential of Pterocarpus marsupium heartwood extract" published in Natural Product Research is praised for its depth of inquiry and exploration of hypoglycemic and antioxidant properties. However, there are areas for refinement, such as clearer definitions of key terms related to type 2 diabetes mellitus, updated literature review, improved organization and contextualization of the Results and Discussion section, and a more balanced discussion of the study's implications.
In search for new metabolites from the stem bark of Calophyllum soulattri and Calophyllum gracilentum, led to the isolation of a new xanthone, soulaxanthone (1), along with four other known metabolites, euxanthone (2), calopolyanolide E (3), calanolide E (4) and friedelin (5). The structures of these compounds were identified and elucidated using spectroscopic techniques such as 1H NMR,13C NMR, COSY, DEPT, HSQC, HMBC, MS and FTIR. The antibacterial activities of compounds 1-5, as well as the extracts, were tested against five bacterial strains. Soulaxanthone (1) exhibited moderate activity against Pseudomonas aeruginosa with an MIC value of 25 µg/mL. Hexane (non-polar) extract from both plants exhibited moderate activity against Enterobacter cloacae (MIC = 250 µg/mL). Calopolyanolide E (3) and friedelin (5) showed bactericidal activity against Enterobacter cloacae (MBC = 50 µg/mL), thus the compounds have the potential to serve as a new lead for developing effective antibacterial medication.