Pyranochromones with Anti-Inflammatory Activities in Arthritis from Calophyllum membranaceum.

Eleven new pyranochromones, calomembranone A-K (1-11), two new pyranocoumarins, calopolyanolide E and F (12 and 13), together with six known analogues (14-19) were isolated from the leaves of Calophyllum membranaceum. Their structures and absolute configurations were elucidated by analysis of spectroscopic data, computational calculations, as well as X-ray crystallography of 4 and 9. The anti-inflammatory activities of all the isolates were evaluated by measuring their NO inhibitory effects in LPS-stimulated RAW 264.7 cells. Structure-activity relationships are also discussed. Compound 7 showed the strongest NO inhibition (IC50 = 0.92 µM). Oral administration of 7 dose-dependently reduced the paw swelling and downregulated neutrophil-to-lymphocyte ratio in the carrageenan-induced acute arthritis mice model. Molecular dynamics simulation and cellular thermal shift assay results indicated that 7 participated in a robust and stable interaction with the active site of TLR4. Compound 7 also suppressed the inflammation in arthritis through the regulation of TLR4 mediated signal transduction via IKK/NF-κB signaling pathway and the consequent reduction of IL-2, IL-4, and IL-5.

Bioassay-guided isolation of anti-tumor polyprenylphloroglucinols from Calophyllum polyanthum and primary mechanism.

Five compounds were isolated from Calophyllum polyanthum leaves (10.09 g) by bioassay-guided fractionation to evaluate their anti-tumor activity. Among these compounds, apetalic acid (1) demonstrated significant inhibitory activity against 8 types of tumor cells (MHCC97H, CNE1, CNE2, B16, LOVO, SW480, A549, 1299), especially against two colon cancer cells (LOVO, SW480). Apetalic acid could inhibit cell proliferation, migration, invasion and induce apoptosis. It could significantly up-regulate the expression levels of apoptosis-related genes (BAX, Caspase-9,) and proteins (BAX, Cleaved-caspase-9, Cleaved-caspase-3) and down-regulated the expression of inhibitor of apoptosis gene (Bcl-2) and proteins (Bcl-2, phosphorylated AKT). Possible mechanism of the antitumor activity of apetalic acid derived from Calophyllum polyanthum supports its use in the prevention and treatment of colorectal cancer.

Biodiesel production from Calophyllum inophyllum oil using zinc doped calcium oxide (Plaster of Paris) nanocatalyst.

The present study was mainly focused on the production of biodiesel from Calophyllum inophyllum oil. The oil was characterized by GC-MS and stored for biodiesel production. The heterogeneous catalyst was synthesized for effective production of biodiesel. The synthesized catalyst was found to have good activity and stability. The surface and element characterization of zinc doped calcium oxide was characterized by SEM and EDAX. The size of nanocomposite was found to be in the range of 14.3-65.6 nm. The EDAX has confirmed the presence of zinc on the surface of the calcium oxide. The maximum biodiesel yield of 89.0% (v/v) was obtained at 55 °C in 80 min and catalyst concentration of 6% (w/v). The optimized methanol:oil molar ratio was obtained at 9:1 for the production of biodiesel. The produced methyl ester was confirmed by GC-MS analysis.

Calofolic acids A-F, chromanones from the bark of Calophyllum scriblitifolium with vasorelaxation activity.

Vasorelaxation activity guided separation of the methanol extract of Calophyllum scriblitifolium bark led to the isolation of 6 chromanones (calofolic acids A-F, 1-6). Their structures were elucidated by 1D and 2D NMR spectroscopy, and their absolute configurations were investigated by a combination of CD spectroscopy and DFT calculation. All isolated chromanones showed dose-dependent vasorelaxation activity on isolated rat aorta.

Identification of candidate genes related to calanolide biosynthesis by transcriptome sequencing of Calophyllum brasiliense (Calophyllaceae).

BACKGROUND: Calophyllum brasiliense is highlighted as an important resource of calanolides, which are dipyranocoumarins that inhibit the reverse transcriptase of human immunodeficiency virus type 1 (HIV-1 RT). Despite having great medicinal importance, enzymes involved in calanolide, biosynthesis and the pathway itself, are still largely unknown. Additionally, no genomic resources exist for this plant species. RESULTS: In this work, we first analyzed the transcriptome of C. brasiliense leaves, stem, and roots using a RNA-seq strategy, which provided a dataset for functional gene mining. According to the structures of the calanolides, putative biosynthetic pathways were proposed. Finally, candidate unigenes in the transcriptome dataset, potentially involved in umbelliferone and calanolide (angular pyranocoumarin) biosynthetic pathways, were screened using mainly homology-based BLAST and phylogenetic analyses. CONCLUSIONS: The unigene dataset that was generated in this study provides an important resource for further molecular studies of C. brasiliense, especially for functional analysis of candidate genes involved in the biosynthetic pathways of linear and angular pyranocoumarins.

Utilization of Calophyllum inophyllum shell and kernel oil cake for reducing sugar production.

This study is aimed at fully utilizing fruit biomass of Calophyllum inophyllum for reducing sugar production. The effects of pretreatment conditions and post reaction wash on the lignin removal and enzymatic hydrolysis of shell were investigated. The oil cake was also subjected to solvent extraction followed by enzymatic hydrolysis. The results showed that the sequential acid/alkaline pretreatment of C. inophyllum shell resulted in better delignification than alkaline or acid only pretreatment. The reducing sugar yields obtained from sequential acid/alkaline pretreated shell and solvent extracted oil cake were 0.24g/g and 0.66g/g, respectively. The results suggested that the shell and oil cake of C. inophyllum could also be feedstocks for reducing sugar production.

Biohydrogen and polyhydroxyalkanoate co-production by Enterobacter aerogenes and Rhodobacter sphaeroides from Calophyllum inophyllum oil cake.

The feasibility of coupled biohydrogen and polyhydroxyalkanoate production by Enterobacter aerogenes and Rhodobacter sphaeroides using Calophyllum inophyllum oil cake was studied under dark and photo fermentation conditions. The utilization of a non-edible acidic oil cake (C. inophyllum), and exploitation of a modified minimal salt media led to reduction in the cost of media. Cost of fermentation is reduced by implementation of alternate dark-photo fermentative periods and through the use of a co-culture consisting of a dark fermentative (E. aerogenes) and a photo fermentative (R. sphaeroides) bacterium. The biohydrogen and polyhydroxyalkanoate produced were 7.95 L H2/L media and 10.73 g/L media, respectively, under alternate dark and photo fermentation and were 3.23 L H2/L media and 5.6g/L media, respectively under complete dark fermentation. The characteristics of the oil cake and alternate dark (16 h) and photo (8h) fermentative conditions were found to be supportive in producing high biohydrogen and polyhydroxyalkanoate (PHA) yield.

Diastereomeric mixture of calophyllic acid and isocalophyllic acid stimulates glucose uptake in skeletal muscle cells: involvement of PI-3-kinase- and ERK1/2-dependent pathways.

The diastereomeric mixture of calophyllic acid and isocalophyllic acid (F015) isolated from the leaves of Calophyllum inophyllum was investigated for the metabolic effect on glucose transport in skeletal muscle cells. In L6 myotubes, F015 dose-dependently stimulated glucose uptake by increasing translocation of glucose transporter4 (GLUT4) to plasma membrane without affecting their gene expression. The effects on glucose uptake were additive to insulin. Inhibitors analyses revealed that F015-induced glucose uptake was dependent on the activation of phosphatidylinositol-3-kinase (PI-3-K) and extracellular signal-regulated kinases 1 and 2 (ERK1/2), while independent to the activation of 5'AMP-activated kinase (AMPK). F015 significantly increased the phosphorylation of AKT, AS160 and ERK1/2, account for the augmented glucose transport capacity in L6 myotubes. Furthermore, F015 improved glucose tolerance and enhanced insulin sensitivity in skeletal muscle of dexamethasone-induced insulin resistant mice. Our findings demonstrate that F015 activates glucose uptake in skeletal muscle cells through PI-3-K- and EKR1/2-dependent mechanisms and can be a potential lead for the management of diabetes and obesity.

Phytostabilization of iron ore tailings through Calophyllum inophyllum L.

The phytostabilization of waste material generated during mining and processing of iron ore through Calophyllum inophyllum L. have been investigated. Iron ore tailings and its varying composition with garden soil were taken to study plant growth, chlorophyll content and metal uptake pattern of Calophyllum inophyllum L. These studies indicate that 100% survival of plant species was noted in all the treatments without any toxicity symptoms. The increase in growth parameters and chlorophyll content along with the high metal accumulation in plant tissues suggests that Calophyllum inophyllum L. may be a potential tool for phytoremediation. The accumulation of Pb (1662 microgm/gm) and Fe (2313 microgm/gm) was observed to be maximum in the plant tissues followed by Cu, Zn, Cr, and Ni. The TF values for most of the heavy metals was observed to be > 1 which indicates that the plant can efficiently translocate these toxic metals to its above ground parts. Removal of more than 30% of the most of the heavy metal like Fe, Pb, and Cu & Zn has been observed in all the treatments during one year of observation. The overall study clearly suggests that the plant can be used as an efficient tool for restoration of mining wastes and other similarly contaminated sites.

[Research progress of chromanone derivatives from Calophyllum].

Calophyllum plants have great pharmaceutical value. Some species of this genus are used in folk medicine to treat and cure diseases, such as toothache, rheumatism, diarrhea, chronic ulcers, skin infections, and wounds. The genus is known to be rich in chromanone derivatives, and some of these compounds have antiviral, antifungal, antibacterial, cytotoxic, and other activities. In order to come to a more complete understanding of chromanone derivatives and gain new bioactive constituents from Calophyllum, chemical structures, pharmacological activities, and biogenesis of chromanone derivatives from Calophyllum have been discussed in this review.

Equilibrium, thermodynamic and kinetic studies for the biosorption of aqueous lead(II) ions onto the seed husk of Calophyllum inophyllum.

Biosorption of lead(II) ions from aqueous solution onto the seed husk of Calophyllum inophyllum was investigated in a batch system. Equilibrium, thermodynamics and kinetic studies were conducted by considering the effects of pH, initial metal ion concentration, contact time, and temperature. The results showed that the uptake of the metal ions increased with increase in initial metal ion concentration. The pH for optimum adsorption was 4 for the Pb(II) ions (q=4.86 mg/g and 97.2% adsorption). Langmuir isotherm described the biosorption of Pb(II) ions onto the biomass (R(2)=0.9531) better than the Freundlich model (R(2)=0.7984), and the Temkin model (R(2)=0.8761). Biosorption kinetics data obtained for the metal ions sorption were fitted using pseudo-first-order and pseudo-second-order. It was found that the kinetics data fitted well into the pseudo-second-order kinetics. Thermodynamic parameters such as Gibbs free energy (DeltaG), standard enthalpy (DeltaH) and standard entropy (DeltaS) were evaluated. The result showed that biosorption of the metal ion onto C. inophyllum biomass was spontaneous and endothermic in nature. The results of FTIR (Fourier-transform infrared spectroscopy) revealed that carboxyl, amine, and hydroxyl groups on the biomass surface were involved in the adsorption of Pb(II) ions.

Pattern of anti-HIV dipyranocoumarin expression in callus cultures of Calophyllum inophyllum Linn.

Callus cultures of Calophyllum inophyllum were established using seed, nodal/ internodal and leaf explants on WPM basal medium supplemented with indole-3-butyric acid (IBA), alpha-naphthalene acetic acid (NAA), picloram (4-amino-3,5,6-trichloropicolinic acid), and 6-benzylaminopurine (BAP) in different combinations and concentrations with the view to study the influence of hormones on callus induction and the pattern of expression of dipyranocoumarins including anti-HIV, non-nucleoside reverse transcriptase inhibitors inophyllum B and P in callus cultures. 96.01% seed explants, 87.50% nodal/internodal explants and 86.66% leaf explants were converted into calluses when inoculated on WPM supplemented with IBA 4.0 mg l(-1) along with BAP 1.0 mg l(-1), IBA 4.0 mg l(-1), and picloram 6.0 mg l(-1) along with BAP 2.0 mg l(-1), respectively. Calluses induced from seed explants were white, friable and irregular whereas nodal/internodal and leaf explants induced dark brown, nodular and compact calluses. In order to facilitate the rapid quantitative analysis of dipyranocoumarins under study, a novel HPLC method capable of separating all six dipyranocoumarins in a single isocratic run has been optimized. Quantitative HPLC analysis of callus extracts revealed that highest inophyllum B (40.59 mg 100g callus(-1)) was expressed in callus induced from seed explant on medium containing 2.0 mg l(-1) indole-3-butyric acid, while highest inophyllum P (141.35 mg 100g callus(-1)) was estimated in seed callus induced on medium containing 2.0 mg l(-1) indole-3-butyric acid along with BAP 1.0 mg l(-1).

[Effects of fungal elicitor on inophyllums production in suspension cultured cells of Calophyllum inophyllum L].

AIM: To investigate the effects of fungal elicitors on inophyllums production in suspension cultured cell of Calophyllum inophyllum Linn. METHODS: The pathogen of leaf spot disease of C. inophyllum L. was isolated and prepared as fungal elicitor. The fungal elicitor was added to the medium with different concentrations and culture period. Their effects on biomass and inophyllums content of the suspension of cultured cells were studied. RESULTS: The optimum effects of S-I fungal elicitor concentrations on inophyllums content was 60 mg GE x L(-1). Adding the fungi elicitor into the cell suspension culture system at stationary phase (being cultured for 18 days) resulted in a highest inophyllum content of 59.174 mg x L(-1) at the 3rd day with 27% higher than control. Fungal elicitor treatment promoted the inophyllums accumulation in medium. CONCLUSION: Adding the Stagonospora curtisii (Berk.) Sacc. to the medium was effective approaches to enhance inophyllums yield in the suspension of C. inophyllum L culture cell.