A new furanodihydrobenzoxanthone, artomandin (1), together with three other flavonoid derivatives, artoindonesianin C, artonol B, and artochamin A, as well as β-sitosterol were isolated from the stem bark of Artocarpus kemando. The structures of these compounds were determined on the basis of spectral evidence. All of these compounds displayed inhibition effects to a very susceptible degree in cancer cell line tests. Compound 1 also exhibited significant antioxidant capacity in the free radical 1,1-diphenyl-2-picrylhydrazyl tests.
Detailed chemical studies on the roots of Piper sarmentosum and Piper nigrum have resulted in several alkaloids. The roots of P. sarmentosum gave a new aromatic compound, 1-nitrosoimino-2,4,5-trimethoxybenzene (1). Piper nigrum roots gave pellitorine (2), (E)-1-[3',4'-(methylenedioxy)cinnamoyl]piperidine (3), 2,4-tetradecadienoic acid isobutyl amide (4), piperine (5), sylvamide (6), cepharadione A (7), piperolactam D (8) and paprazine (9). Structural elucidation of these compounds was achieved through NMR and MS techniques. Cytotoxic activity screening of the plant extracts indicated some activity.
An investigation of Morinda citrifolia roots afforded a new anthraquinone, 2-ethoxy-1-hydroxyanthraquinone (1), along with five other known anthraquinones: 1-hydroxy-2-methylanthraquinone (2), damnacanthal (3), nordamnacanthal (4), 2-formyl-1-hydroxyanthraquinone (5) and morindone-6-methyl-ether (6). This is the first report on the isolation of morindone-6-methyl-ether (6) from this plant. The structures of these compounds were elucidated based on spectroscopic analyses such as NMR, MS and IR. Biological evaluation of five pure compounds and all the extracts against the larvae of Aedes aegypti indicated 1-hydroxy-2-methylanthraquinone (2) and damnacanthal (3) were the extracts to exhibit promising larvicidal activities.
Studies on the stem of Garcinia mangostana have led to the isolation of one new xanthone mangosharin (1) (2,6-dihydroxy-8-methoxy-5-(3-methylbut-2-enyl)-xanthone) and six other prenylated xanthones, alpha-mangostin (2), beta-mangostin (3), garcinone D (4), 1,6-dihydroxy-3,7-dimethoxy-2-(3-methylbut-2-enyl)-xanthone (5), mangostanol (6) and 5,9-dihydroxy-8- methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)-2H,6H-pyrano-[3,2-b]-xanthene-6-one (7). The structures of these compounds were determined by spectroscopic methods such as 1H NMR, 13C NMR, mass spectrometry (MS) and by comparison with previous studies. All the crude extracts when screened for their larvicidal activities indicated very good toxicity against the larvae of Aedes aegypti. This article reports the isolation and identification of the above compounds as well as bioassay data for the crude extracts. These bioassay data have not been reported before.
In the authors' continuing search for new natural products, their recent studies on the roots of Calophyllum inophyllum (Guttiferae) have yielded a new prenylated pyranoxanthone, Inophyllin A together with the common triterpenes friedelin and stigmasterol. Structural elucidations of these compounds were achieved through (1)H, (13)C, DEPT, COSY, HSQC and HMBC experiments. The molecular mass was determined using MS techniques. The authors report here the isolation of and structural elucidation for Inophyllin A as well as its toxicity test result. The discovery of this new natural product from the unexploited Malaysian forest will certainly contribute to the search for potential natural larvicides.
Our recent studies on the stem bark of Calophyllum mucigerum (Guttiferae) have yielded a new coumarin mucigerin, a prenylated xanthone cudraxanthone C and the common steroidal triterpenes friedelin and stigmasterol. Structural elucidations of these compounds were achieved using 1H NMR, 13C NMR, DEPT, COSY, HETCOR and HMBC experiments while MS gave the molecular masses. Cytotoxic assays using CEM-SS cell line (T-lymphoblastic leukemia) on the crude extracts of the stem bark indicated some activity. The crude extracts were also found to be moderately toxic against the larvae of Aedes aegypti. This article reports the isolation and identification of mucigerin as well as bioassay data.
Currently, type 2 diabetes mellitus (T2D) has emerged as global burden disease. Herbal drugs with antidiabetic activities are attracting the attention. Madecassoside and catalpol are herbal compounds having strong antioxidant and glucose lowering activity. Madecassoside and catalpol were investigated for their effect on insulin sensitivity using pancreatic INS-1E cells. Cytotoxicity of these compounds was evaluated by MTT assay. Glucose-stimulated insulin secretion (GSIS) and expression of insulin signalling proteins were studied in presence of madecassoside and catalpol. Results revealed that madecassoside and catalpol enhanced the GSIS without cytotoxic effect. Madecassoside (30 µM) and catalpol (40 µM) increased the insulin secretion in response to high glucose (16.7 mM) stimulation. Subsequently, madecassoside and catalpol showed elevated expression of p-IRS-1, Akt, and p-Akt proteins. Madecassoside and catalpol after 24 h of incubation in pancreatic INS-1E cells with high glucose concentration (30 mM) ameliorated the insulin secretion.
The 2,2-diphenyl-1-picryl hydrazyl (DPPH) radical, nitric oxide, reducing power, hydrogen peroxide scavenging, and total antioxidant activities of the methanol extract, n-hexane, dichloromethane, ethyl acetate, butanol and aqueous fractions of the seed of Telfairia occidentalis were evaluated. Total phenolic content was determined using the Folin-Ciocalteu method. The dichloromethane fraction exhibited the highest DPPH radical scavenging, reducing power and total antioxidant activities. Two pure compounds which were identified by FTIR, H-and 2D NMR and Mass spectroscopy as 9-octadecenoic acid (TOS B) and 10-hydroxyoctadecanoic acid (TOS C) and four oily isolates, TOS A, TOS D, TOS E and TOS F were obtained from the dichloromethane fraction. TOS E had the highest DPPH radical scavening activity comparable to that of ascorbic acid. GC-MS analysis revealed the major compounds in TOS E as 4-(2,2-Dimethyl-6-methylene cyclohexylidene)-2-butanol; 3-(3-hydroxybutyl)-2,4,4-trimethyl-2-cyclohexene-1-one and 1,2-Benzenedicarboxylic acid disooctyl ester. Thus, the seed of T. occidentalis can be consumed for its antioxidant property.
Three new dammarane-type triterpenoids, namely elliptaglin A-C (1-3) were isolated from the stem bark of Aglaia elliptica (C.DC.) Blume along with three known derivatives, namely (20S)-hydroxydammar-24-en-3-on (4), cabralealactone (5), and E-25-hydroperoxydammar-23-en-20-ol-3-one (6). Subsequently, their chemical structures were determined using HR-ESI-MS, FTIR, 1D and 2D-NMR spectroscopic analysis as well as comparison with previous studies. The cytotoxicity activities of the isolated compounds against MCF-7 breast cancer and B16-F10 melanoma cell lines were then tested using PrestoBlue reagent. The analysis results showed that elliptaglin B (2) had the strongest activity against both cell lines with IC50 values of 60.98 and 51.83 µM, respectively.
Bioactive phenolics can be found in abundance in Calophyllum species. Phytochemical studies are carried out on the stem bark of Calophyllum recurvatum and Calophyllum andersonii, which has led to the isolation and elucidation of phytochemicals, thwaitesixanthone (1), teysmanone A (2), soulattrolide (3), calanone (4), isocalanone (5) and friedelin (6), respectively. The cytotoxic activities of compounds (2), (3), (4) and (5) as well as plant extracts were tested against HeLa Chang liver, HepG2 and HL-7702 cell lines. Phenylpyranocoumarins, teysmanone A (2) and soulattrolide (3) portrayed appreciable cytotoxicity activities at 42.57 ± 1.20 and 34.53 ± 3.41 µg/mL, respectively against HepG2 cell line comparable to the positive control, curcumin. Meanwhile, n-hexane extract from C. recurvatum exhibited cytotoxicity with the IC50 value of 36.43 ± 0.64 and 26.25 ± 4.83 µg/mL against HeLa Chang liver and HepG2 cell lines. All the tested compounds and plant extracts displayed non-cytotoxic properties on HL-7702 cell line.
The aim of this study was designed to analyse the effect of Savoury essential oil (Satureja hortensis) on growth performance, biochemical parameters and immunity of angelfish (Pterophyllum scalare). The angelfishes (average body weight of 5.12 ± 0.01 g) were treated with three effective dosage of Savoury essential oil 100, 200 and 400 mg/kg in three separated aquaria water with one control group for 60 days. At the end of experiment, the angelfishes treated with 400 mg/kg Satureja showed minimum Feed Conversion Ratio, maximum Specific Growth Rate and Survival Rate. There was significant difference (p
The leaves of Cinnamomum iners (Reinw. ex Blume-Lauraceae) have been refluxed successively with chloroform and alcohol to get chloroform extract and alcoholic extract. Both the extracts have been assayed for cytotoxicity against human colorectal tumour cells. The chloroform extract exhibited significant cytotoxicity with IC(50) 31 µg mL(-1) (p 200 µg mL(-1). The chloroform extract has been further proceeded for chemical analysis by GC-TOFMS and 178 components were identified including acids, amines, amides, aldehydes, alcohols, esters, benzene derivatives, bicyclic compounds, terpenes, hydrocarbons, naphthalene derivatives, furan derivatives, azulenes, etc. Nine components representing 51.73% of the total chloroform extract were detected as major components. Caryophyllene (14.41%) and Eicosanoic acid ethyl ester (12.17%) are the most prominent components of the chloroform extract. β-Caryophyllene (14.41%) as most abundant compound supports potent cytotoxicity as shown by chloroform extract.
The marine soft corals Sarcophyton trocheliophorum crude extracts possessed antimicrobial activity towards pathogenic bacterial strains, i.e. Bacillus cereus, Salmonella typhi, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. Bioassay-guided fractionation indicated that the antimicrobial effect was due to the presence of terpenoid bioactive derivatives. Further biological assays of the n-hexane fractions were carried out using turbidity assay, inhibition zone assay and minimum inhibitory concentration for investigating the growth-inhibition effect towards the Gram-positive and Gram-negative bacteria. The fractions were screened and the structure of the isolated compound was justified by interpretation of the spectroscopic data, mainly mass spectrometry (GC-MS). The structure was assigned as (5S)-3-[(3E,5S)-5-hydroxy-3-hepten-6-yn-1-yl]-5-methyl-2(5H)-furanone and was effective at concentrations as low as 0.20 mg/mL. The above findings, in the course of our ongoing research on marine products, may implicate that the profound anti-microbial activity of the S. trocheliophorum soft corals, inhabiting the red sea reefs, is attributed to the presence of growth-inhibiting secondary metabolites mainly terpenoids.
The red alga Chondria armata is known to produce and contain a rich diversity of secondary metabolites, such as domoic acid-related alkaloids and triterpene polyethers. Our investigation on red alga C. armata from Kagoshima coast, Japan, resulted in the isolation of two new triterpene polyethers, bandokorols A (1) and B (2). The structures of these compounds were determined based on spectroscopic data such as infrared (FTIR), 1H-NMR, APT, 1H-1H-COSY, HSQC, HMBC, NOESY and FAB mass spectrometry (HRFABMS). The anticancer potentials of these compounds were tested against adult T-cell leukaemia (ATL), S1T cells and their IC50 values are reported here.
Cashew (Anacardium occidentale L.) leaf is traditionally used to treat skin infections. Although many flavonols have been identified from its leaf extract, their inhibitory effects on skin pathogens are not yet determined. The aims of this study were to determine the antimicrobial (against skin pathogenic microbes) and antioxidant activities of four flavonol glycosides from the crude extract and three flavonol aglycones from the hydrolyzed extract. The hydrolyzed extract was found to show higher activities than the crude extract. Myricetin showed the highest activity against all the tested bacteria and yeast with the lowest Minimum Inhibition Concentration (MIC) of 7.81 μg/mL on Corynebacterium minutissimum ATCC23348. Myricetin also exhibited good primary antioxidant activities with the effective concentration with 50% of activity (EC50) values ranged between 2.23 μg/mL and 6.40 μg/mL. The highest secondary antioxidant activity was indicated by myricetin-3-O-rhamnoside. Thus, myricetin can be considered as a bioactive compound of the hydrolyzed extract.
Ethanol and aqueous extracts of the different parts of Piper sarmentosum were analysed by HPLC for marker compounds to standardise these extracts. The standardised extracts were investigated for antioxidant activity (beta-carotene linoleate model and DPPH model), anti-TB activity (microplate tetrazolium assay), and estimation of total phenolic and amide contents. The extracts of the different parts exhibited different antioxidant activity, phenolic and amide contents (p < 0.01). The ethanol extracts exhibited better antioxidant activity as compared to the aqueous extracts. The leaf ethanol extract was further investigated for dose response relationship and its EC(50) was found to be 38 microg mL(-1). All the extracts have exhibited anti-TB activity with MIC/MBC 12.5 microg mL(-1). The leaf methanol extract was fractionated and the ethyl acetate fraction exhibited anti-TB activity with MIC/MBC 3.12 microg mL(-1) while MIC/MBC of isoniazid (INH) was found to be 0.5 microg mL(-1). A positive correlation was found between antioxidant activity and total polyphenols, flavonoids and amides, in the beta-carotene linoleate model (p = 0.05) and in the DPPH model (p = 0.01). The analytical method was found to have linearity >0.9922, coefficient of variance <5% and accuracy 95.5 +/- 5 to 96.9 +/- 5. This plant possesses promising antioxidant as well as anti-TB properties.
The stem bark extracts of Knema laurina inhibited the hydrogen peroxide (H2O2)- and aggregated amyloid β-peptide 1-42 length (Aβ(1-42))-induced cell death in differentiated SH-SY5Y cells. Exposure of 250 μM H2O2 or 20 μM Aβ(1-42) to the cells for 24 h reduced 50% of cell viability. Pretreatment of cells with ethyl acetate extract (EAE) or n-butanol extract (BE) at 300 μg/mL and then exposure to H2O2 protected the cells against the neurotoxic effects of H2O2. Besides, methanolic extract (ME) at 1 and 10 μg/mL exerted neuroprotective effect on Aβ(1-42)-induced toxicity to the cells. These results showed that EAE, BE and ME exhibited neuroprotective activities against H2O2- and Aβ(1-42)-induced cell death. Flavonoids (3-6) and β-sitosterol glucoside (8) were isolated from the EAE. Compound 1 was isolated from hexane extract, and compounds 2 and 7 were isolated from dichloromethane extract. All these observations provide the possible evidence for contribution in the neuroprotective effects.
Clinacanthus nutans has been reported to have many medicinal properties and it is traditionally used in treating viral lesions. This study aims to determine the molecular docking of C. nutans compounds detected by Gas Chromatography-Mass Spectrometry (GC-MS) with the novel severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2 main protease) protein and its host receptor angiotensin-converting enzyme 2 (ACE2) protein using the AutoDock 4.2 tool. The drug-likeness and molecular docking analyses showed that fourteen compounds of C. nutans satisfied the Lipinski's rule of five and they exhibited good inhibitory effects against the SARS-Cov-2 main protease and ACE2 proteins. In addition, the glyceryl 2-linolenate compound was found to have the most potent binding affinities with both proteins. The results provide useful insights into the molecular inhibitory interactions of C. nutans compounds detected by GC-MS analysis with the targeted SARS-CoV-2 main protease and ACE2 protein.
Stereospermum fimbriatum or locally known as "Chicha" is traditionally used for itchy skin, earache, stomachache and postpartum treatments. This study was designed to evaluate the antimicrobial potential of S. fimbriatum's stem bark against 11 pathogens and isolate its bioactive compound. Successive soxhlet extraction was conducted using n-hexane, dichloromethane (DCM) and methanol. Disc diffusion, minimum inhibitory and bactericidal concentration (MIC & MBC) assays were done to examine the antimicrobial activity. Bioassay-guided isolation was conducted on S. fimbriatum's extract. The DCM extract of stem bark (DS) was the most potent extract followed by n-hexane extract of the stem bark (NS). A novel compound was isolated and coded as C1 which demonstrated potent antibacterial effects with the MIC values as low as 3.13 µg/mL to 6.25 µg/mL, against S. epidermidis, MRSA and S. aureus. Thus, S. fimbriatum could be a potential source of antimicrobial agents for the treatment of skin infections, specifically, MRSA.
Garcinia species are reported to possess antimicrobial, anti-inflammatory, anticancer, anti-HIV and anti-Alzheimer's activities. This study aimed to investigate the in vitro cholinesterase enzyme inhibitory activities of garcihombronane C (1), garcihombronane F (2), garcihombronane I (3), garcihombronane N (4), friedelin (5), clerosterol (6), spinasterol glucoside (7) and 3β-hydroxy lup-12,20(29)-diene (8) isolated from Garcinia hombroniana, and to perform molecular docking simulation to get insight into the binding interactions of the ligands and enzymes. The cholinesterase inhibitory activities were evaluated using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. In this study, compound 4 displayed the highest concentration-dependent inhibition of both AChE and BChE. Docking studies exhibited that compound 4 binds through hydrogen bonds to amino acid residues of AChE and BChE. The calculated docking and binding energies also supported the in vitro inhibitory profiles of IC50. In conclusion, garcihombronanes C, F, I and N (1-4) exhibited dual and moderate inhibitory activities against AChE and BChE.