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Unlike reported pyridine hybrids, 2

Jin-Gu-Lian (JGL) is traditionally used by Miao for the treatment of rheumatism arthralgia. At the same time, the combination of

The chemotherapy drug doxorubicin (DOX) is effective in treating many types of cancers. However, due to its pro-inflammatory and cardiotoxic side effects, other remedies have also been explored as alternative treatments. The plant Alangium longiflorum was reported to contain cytotoxic activity against cancer cells, but it is unclear whether this plant would also yield side effects similar to doxorubicin. Hence, this study investigated cytotoxic activity of A. longiflorum leaf extract against lung cancer cells and compared its pro-inflammatory and cardiotoxic side effects with those of DOX. Methods Cytotoxic activity of A. longiflorum in human lung (A549) and breast (MCF-7) cancer cells was initially assessed by MTT assay and then was compared with doxorubicin. Presence of secondary metabolites in the leaf extract was examined by phytochemical screening. The ability of the plant extract to induce apoptosis was determined by measuring caspase-3/7 activity and apoptosis-related gene expression. Pro-inflammatory response was assessed by quantifying NFκB transcriptional activity and nuclear translocation with dual luciferase reporter and immunofluorescence assays, respectively. Cardiotoxicity was measured using zebrafish as a model organism. Results A. longiflorum leaf extract displayed high cytotoxic activity against A549 versus MCF-7, which led this study to focus further on A549. Phytochemical screening showed that the extract contained terpenoids, alkaloids, phenols, cardiac glycosides, and tannins. The extract induced apoptosis through activation of caspase-3/7 and upregulation of pro-apoptotic genes without causing NFκB transcriptional activation and nuclear localization. The extract also did not significantly reduce heart function in zebrafish. Conclusion Overall, our data suggested that extract from leaves of A. longiflorum can have the potential to serve as apoptotic agent towards lung cancer without inducing significant cardiotoxicity.

Nine new cadinane sesquiterpenoids, alanenses A-I (

There is an urge for traditional herbal remedies as an alternative to modern medicine in treating several ailments. Alangium salviifolium is one such plant, used traditionally to treat several diseases. In several reports, there are findings related to the use of this plant extract that demonstrate its therapeutic value. However, very few attempts have been made to identify the extensive metabolite composition of this plant. Here, we performed metabolite profiling and identification from the bark of A. salviifolium by extracting the sample in organic and aqueous solvents. The organic and aqueous extracts were fraction-collected using the Agilent 1260 Analytical Scale Fraction Collection System. Each of the fractions was analyzed on Liquid Chromatogaphy/Quadrupole Time-of-Flight LC/Q-TOF and Gas Chromatography/Quadrupole Time-of-Flight GC/instruments. The Liquid Chromatography/Mass Spectrometry (LC/MS) analyses were performed using Hydrophilic Ineraction Liquid Chromatography (HILIC), as well as reversed-phase chromatography using three separate, orthogonal reverse phase columns. Samples were analyzed using an Agilent Jet Stream (AJS) source in both positive and negative ionization modes. The compounds found were flavonoids, fatty acids, sugars, and terpenes. Eighty-one secondary metabolites were identified as having therapeutic potential. The data produced was against the METLIN database using accurate mass and/or MS/MS library matching. Compounds from Alangium that could not be identified by database or library matching were subsequently searched against the ChemSpider) database of over 30 million structures using MSMS data and Agilent MSC software.In order to identify compounds generated by GC/MS, the data were searched against the AgilentFiehn GCMS Metabolomics Library as well as the Wiley/NIST libraries.

A new phenolic glycoside, chinenside A (

As part of a continuing research program aiming to identify chemical probes to interrogate Parkinson's disease (PD), we have investigated the Australian plants

In this study, the hepatoprotective activity of methanol bark extract of

Alangium longiflorum is currently in extinction crisis, which will likely severely hamper further phytochemical investigation of this plant species from new collections. A crude extract of leaves of A. longiflorum (N33539), collected for the U.S. National Cancer Institute in 1989, showed potent cancer cell line antiproliferative activity. A phytochemical study resulted in the isolation of 17 secondary metabolites, including two new tetrahydroisoquinoline alkaloids, 8-hydroxytubulosine (1) and 2'- O- trans-sinapoylisoalangiside (2), as well as a new sinapolyloxylupene derivative (3). Using in-house assays and NCI-60 panel screening, compound 1 displayed broad-spectrum inhibitory activity at submicromolar levels against most tested tumor cell lines, except for drug-transporter-overexpressing cells. Compound 1 caused accumulation of sub-G1 cells with no effect on cell cycle progression, suggesting that this substance is an apoptosis inducer.

Rheumatoid arthritis (RA) is a chronic inflammatory disorder linked to oxidative stress of rheumatoid arthritis fibroblast-like synoviocytes (RA-FLSs). The effects and potential mechanism of salicin on inflammation and oxidative stress of RA-FLSs were examined by MTT, ELISA, and Western blot methods. Salicin significantly reduced cell viability (82.03 ± 7.06, P < 0.01), cytokines (47.70 ± 1.48 ng/L for TNF-α, 30.03 ± 3.49 ng/L for IL-6) ( P < 0.01), and matrix metalloproteinases-1/-3 expression ( P < 0.01) in IL-1β-induced RA-FLSs and inhibited ROS generation and p65 phosphorylation ( P < 0.01) as compared with IL-1β-induced treatment. Moreover, salicin promoted Nrf2 nuclear translocation (2.15 ± 0.21) and HO-1 expression (1.12 ± 0.05) and reduced ROS production in IL-1β-induced RA-FLSs ( P < 0.01). Salicin not only reduced the collagen-induced arthritis by reducing the clinical score ( P < 0.01), inflammatory infiltration, and synovial hyperplasia in vivo but also suppressed the oxidative damage indexes (SOD 155.40 ± 6.53 U/mg tissue, MDA 152.80 ± 5.89 nmol/g tissue, GSH 50.98 ± 3.45 nmol/g tissue, and CAT 0.92 ± 0.10 U/g protein) ( P < 0.01) of ankle joint cells. Conclusively, our findings indicate that salicin ameliorates rheumatoid arthritis, which may be associated with oxidative stress and Nrf2-HO-1-ROS pathways in RA-FLSs.

One unusual metal complex of cadinane sesquiterpene alkaloid (1), one new cadinane sesquiterpene alkaloid (2) and two new neolignan glycosides (3-4) along with six known cadinane sesquiterpene derivatives (5-10), nineteen known phenolic glycosides (11-29) were isolated from the aerial parts of Alangium alpinum. Structures of new crystals of metal complex were characterized by X-Ray diffraction and ICP-AES analysis. Other new compounds were elucidated by combined use and detailed analysis of HR-ESIMS, 1D and 2D NMR and CD spectroscopic method. In addition, all isolated compounds were tested for their inhibitory effects against TNF-α induced NF-κB activation in Hela cells and NO production in RAW 264.7 macrophages.

Plant extracts with their enriched chemical constituents have established potential alternative mosquito control agents. In this research, we developed an eco-friendly mosquitocidal agent from Alangium salvifolium leaves against the dengue and Zika virus vector Aedes aegypti and we investigated its biosafety on the mosquito aquatic predator Toxorhynchites splendens. Results showed that the methanolic extract of A. salvifolium leaves was composed by eight main compounds, with major peak area for hexadecenoic acid (21.74%). LC50 and LC90 values calculated on Ae. aegypti fourth instar larvae were 104.80 and 269.15 ppm respectively. The methanolic extract tested at 100 ppm decreased the α-β carboxylesterase and SOD ratio significantly and upregulated the GST and CYP450 level. The A. salvifolium methanolic extract displayed significant repellent and adulticidal activity at 100 and 400 ppm respectively. The treatment with 100 ppm of the methanolic extract led to 210 min of protection from Ae. aegypti bites. Four hundred parts per million of the extract showed 98% adult mortality within 30 min from the treatment. Lastly, biosafety assays on the mosquito aquatic predator Tx. splendens showed that the toxicity of the A. salvifolium extract was significantly lower if compared to the cypermethrin-based treatments. The methanolic extract of A. salvifolium showed a maximum of 47.3% mortality rate at the concentration of 1000 ppm, while 0.7 ppm of cypermethrin achieved 91.3% mortality rate on Tx. splendens. Overall, our study enhances basic knowledge on how to improve natural larvicidal agents against dengue and Zika virus mosquito vector with harmless responses on non-target aquatic predators.

Alangium Lam. sect. Conostigma Bloemb. is largely confined to the Malesian area and contains 19 species. By using the characters as found in the original species-descriptions, and with emphasizing the nature of the indument of the leaf bud, the confusingly variable Alangium javanicum s.l.-complex could be dismantled for a great part. Four new species: A. ledermannii, A. pallens, A. plumbeum, and A. subcordatum, and two new varieties: A. meyeri var. macilentum and A. ebenaceum var. insignis are recognised. Two taxa are raised to specific status: A. nobile subsp. denudatum to A. denudatum and A. javanicum var. minahassicum to A. minahassicum. A key to the species is presented, and the concerned taxa are enumerated, referenced, described and some are figured.

Alangium sect. Rhytidandra is confined to SE Asia, the Pacific and East Australia, and contains 13 species. Five species, viz. Alangium brassii, A. glabrum, A. gracile, A. guadalcanalense, and A. velutinum are described as new, whereas A. villosum subsp. solomonense is raised to specific rank: A. solomonense. Subspecies tomentosum formerly in A. villosum is transferred to another species and has become A. polyosmoides subsp. tomentosum. Finally Iodes ferruginea, described in Icacinaceae appeared to belong in Alangiaceae, and as the name ferruginea was occupied in Alangium it is changed into A. strigosum, nom. nov. A key to the species is presented, and the concerned taxa are enumerated, referenced, described, and two are figured.

Two previously undescribed flavonols with phenylpropanoid or benzyl substitution, named alangsine A (1), and alangsine B (2), together with four known compounds (3-6) were isolated from the leaves of Alangium chinense. Alangsine A was a racemic mixture, which was further separated into two enantiomers via high-performance liquid chromatography on a chiral column. The absolute configurations of the enantiomer pairs were deduced from the circular dichroism (CD) spectra. The activity of the isolated compounds towards neuronal excitability was examined.

The species from Alangium have been used as folk medicine to treat rheumatism, skin diseases, diabetes by the people of Southeast Asia. Previous phytochemical studies have shown this genus are rich sources of alkaloids, glycosides, and terpenoids, which have attracted considerable attention of many researchers due to their markedly diverse and complex architecture. The crude extracts as well as the monomeric compounds from the title genus possess anti-tumor, anti-inflammatory, antibacterial, anti-oxidant pharmacological activities. Besides, some isolates from Alangium exhibited the effects on skeletal, smooth muscle and the nervous system. As a large genus of medicinal plants, the medicinal value of Alangium has been widely reported, but there is no review that provide a systematic summary towards its chemical constituents and pharmacological activities, to our knowledge. This work aims to present a comprehensive overview on the traditional uses, phytochemistry, and pharmacological activities of medicinal plants in the genus Alangium, and to explore the evidence supporting its ethnopharmacological effectiveness.

Alangium sect. Alangium comprises 11 species (and two varieties). The species are primarily defined by their growth habit, viz. erect shrubs or trees versus scandent plants, with additional characters derived from the inflorescences, the size of the flowers, and particulars of the stamens. A key to the species and species descriptions with brief associated information are presented. Alangium amplum W.J.de Wilde & Duyfjes, A. indochinense W.J.de Wilde & Duyfjes, A. melliferum W.J.de Wilde & Duyfjes, and A. sempervirens W.J.de Wilde & Duyfjes are new species; A. frutescens Zoll. & Mor. var. palawanense W.J.de Wilde & Duyfjes is a new variety, and A . longiflorum Merr. var. brachyanthum (Merr.) W.J.de Wilde & Duyfjes a new combination.

Studies on the structural determination, biosynthesis, and biological activities of secondary metabolites from natural sources are significant in the field of natural products chemistry. This review focuses on diverse secondary metabolites isolated from medicinal plants and cultivated mycobionts of lichens in our laboratory. Monoterpene-tetrahydroisoquinoline glycosides and alkaloids isolated from Cephaelis acuminata and Alangium lamarckii gave important information on the biosynthesis of ipecac alkaloids. A variety of glycosides linked with a secologanin unit and indole alkaloids were obtained from medicinal plants belonging to the families of Rubiaceae, Apocynaceae, and Loganiaceae. Plant species of the four genera Fraxinus, Syringa, Jasminum, and Ligustrum of the family Oleaceae were chemically investigated to provide several types of secoiridoid and iridoid glucosides. The biosynthetic pathway leading from protopine to benzophenanthridine alkaloids in suspension cell cultures of Eschscholtzia californica was elucidated. The structures and biological activities of the bisbenzylisoquinoline alkaloids of Stephania cepharantha and Nelumbo nucifera were also investigated. In addition, the mycobionts of lichens were cultivated to afford various types of metabolites that differ from the lichen substances of intact lichens but are structurally similar to fungal metabolites. The biosynthetic origins of some metabolites were also studied. These findings suggest that cultures of lichen mycobionts could be sources of new bioactive compounds and good systems for investigating secondary metabolism in lichens.

Now a day’s world population moves towards herbal remedies for treatment of various ailments. Plants have the ability to synthesize a wide variety of chemical compounds that are used to perform important biological functions. In India, medicinal plants are widely used by people as folk remedies and pharmaceutical preparations. Alangium salvifolium is a deciduous shrub belongs to family Alangiaceae with a long history of traditional medicinal uses in many countries, especially in India, China and Phillipines. The herb exhibits a broad range of therapeutic effects as an effective natural remedy for rheumatism, leprosy, hemorrhoid, burning sensation, constipation and antidote for several poisons. A wide range of chemical compounds including alkaloids, steroids, terpenoids, flavonoids, and saponins have been isolated from the species. Its extracts have been found to possess various pharmacological activities. In this paper, we give a comprehensive review of its habitat, taxonomy, distribution, identification ethnomedical uses, chemical constituents, and pharmacological profile of this medicinal plant.

Seven new lignan glycosides (1-3, 8-10, and 14) and 17 known compounds were isolated from the branches of Alangium kurzii Craib var. laxifolium. Their structures were established by spectroscopic analysis and circular dichroism (CD) and X-ray analysis. The isolated compounds were evaluated for their antibacterial activities against Staphylococcus aureus CI1011, Streptococcus suis CI1608, Salmonella gallinarum CI0912, Enterococcus faecalis CI1304, Aeromonas hydrophila CI1008, Escherichia coli CI151012, Vibrio parahaemolyticus CI150506, Klebsiella pneumoniae CI131216, Pseudomonas aeruginosa CI1011, Staphylococcus epidermidis CI1110, and Streptococcus agalactiae CI1302. Their minimum inhibitory concentrations (MICs) were determined by serial dilution in 96-well culture plates.

The components of the essential oil from the roots of Alangium salviifolium were analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Ninety compounds, representing 74.5% of the total oil, were identified; the main components of the oil were epi-α-cadinol, followed by trans-2-hydroxycalamenene, cadalene, and cadina-4,10(15)-dien-3-one. A further unknown component comprised 5.5% of the oil. Therefore, the essential oil was purified by flash column chromatography to isolate this component. Its structure was established using extensive spectroscopic data analyses, including NMR, HR-EI-MS, and IR. The results showed that this isolated compound was (-)-7, 8-dihydroxycalamenal, which is a novel cadinane-type sesquiterpenoid. This compound was tested for its antioxidant activity and inhibition of tyrosinase, and showed particularly strong inhibition effects.

The present study aimed to evaluate the antinociceptive and anti-inflammatory activity of Alangium salvifolium (AS) flower in mice. The antinociceptive activity was determined using tail immerson, acetic acid induced writhing and formalin induced licking test. Antiinflammatory effects were evaluated using carrageenan and formalin induced paw edema in mice. The methanol extract (50 and 100 mg kg(-1)) of flower of AS followed by chloroform extract (100 mg kg(-1)) produced a significant inhibition of both phases of the formalin pain test in mice, a reduction in mice writhing induced by acetic acid and delayed the response of mice to hot water thermal stimulation in tail immersion test. All flowers extract of AS also produced a substantial inhibition (nearly 50%) of carrageenan and formalin induced paw edema. The inhibitions were similar to those produced by indomethacin, p.o. The different alkaloids and flavonoids found in the extract could be account for the antinociceptive and anti-inflammatory actions.

We have carried out the chemical investigation on the roots of Alangium chinense. The chemical constituents from the roots of A.chinense were isolated and purified by various chromatographic techniques, such as silica gel, MCI-Gel resin, Sephadex LH-20 and high performance liquid chromatography. As a result, three alkaloids (1-3) were isolated from 90% EtOH extracts of the roots of this plant. Their structures were elucidated by physical-chemical properties and spectral data. Among them, compound 1 is a new compound, determined as 8-hydroxy-3-hydroxymethyl-6,9-dimethyl-7H-benzo[de]isoquinolin-7-one. Cytotoxicity of the compounds was evaluated by the MTT method. Compound 1 displayed cytotoxicity against NB4, A-549, SHSY5Y, PC-3 and MCF-7 cell lines with IC₅₀ values of 4.2, 3.5, 5.7, 2.8 and 3.9 μmol•L⁻¹, respectively.

The bioconversion of tyrosine, dopamine, N- desacetylisoipecoside (15) and N- desacetylipecoside (16) into cephaeline (2), emetine (1), and psychotrine (3) into Alangium lamarckii Thw. (Alangiaceae) plant has been studied. Stereospecific incorporation of N- desacetylisoipecoside (15) into 1,2 and 3 has been demonstrated. Further it has been shown that reduction of C1’ – C2’ takes place after O-methylation of psychotrine (3). Feeding results further showed that cephaeline was poorly metabolized in the plants to form psychotrine (3) thus demonstrating that dehydrogenation of C1’ – C2’ does not take place. The efficient incorporation of cephaeline into emetine (1) further showed that O- methylation is the terminal step in the biosynthesis of emetine. Emetine (1) was poorly metabolized by the plants to form cephaeline (2) and psychotrine (3). The experiments thus demonstrated that dehydrogenation and O-demethylation of emetine (1) does not occur to give cephaeline (2) and psychotrine (3). Scientific World, Vol. 10, No. 10, July 2012 p24-28 DOI: http://dx.doi.org/10.3126/sw.v10i10.6857

Objective To assesse the inhibitory effect of alcoholic extract of two Indian medicinal plants namely Ceasalpinia digyna Rottler and, Alangium lamarckii Thwaits on aldose reductase (AR) of rat lens. Methods Rats lens were enucleated through posterior approach and their homogenate was prepared and centrifuged to obtain a clear supernatant for the determination of AR activity and protein content. Results The alcoholic extract of Ceasalpinia digyna and Alangium lamarckii had a potent inhibitory effect on the lens AR enzyme. The IC 50 values of alcoholic extract of the selected plants were calculated and were (46.29±11.17) and (106.00±5.11) μg/mL, respectively. Quercetin was used as a positive control and its IC 50 value was (2.95±1.53) μg/mL. Conclusions Thus, it is concluded that alcoholic extracts of the selected plant exhibit significant inhibitory effects on AR in the rat lens in vitro .

Root bark of Alangium salvifolium (Linn.f.) Wang. (Family Alangiaceae) is a reputed drug mentioned in the ancient books of Ayurveda and Siddha for the treatment of epilepsy, jaundice, hepatitis etc. Root bark of the plant was subjected to macro-microscopic, photomicrographic, physico-chemical, fluorescence, preliminary phytochemical, TLC and HPTLC to fix quality standards for this drug. Microscopic studies have shown stratified phellem, rhytidome, cluster crystals of calcium oxalate and uni- to triseriate medullary rays in the root bark. Chloroform, ethyl acetate, ethanol extracts and alkaloid fraction revealed characteristic chromatographic patterns with presence of alkaloids in varying concentrations. This study would be useful in the identification and authentication of the raw drug.

Three new phenolic glycosides, salviifosides A−C ( 13 ), and three known compounds salicin ( 4 ), kaempferol ( 5 ), and kaempferol 3- O- β- d -glucopyranoside ( 6 ) were isolated from the leaves of Alangium salviifolium (L.f.) Wangerin (Alangiaceae). The structures of the new metabolites were determined on the basic of spectroscopic analyses including two dimensional NMR. The anti-inflammatory activities of new compounds ( 1 − 3 ) were investigated on lipopolysaccharide (LPS)-induced murine macrophage cells line, RAW 264.7. Salviifoside B ( 2 ) potentially inhibits the productions of nitric oxide (NO), prostaglandin E 2 (PGE 2 ), and tumor necrosis factor-α (TNF-α).

Alangiaceae, in the basal Asterid clade Cornales, consists of only one genus, Alangium. The genus has approximately 24 species distributed mainly in tropical and subtropical regions of the Old World and is well represented in the Tertiary fossil record of the northern hemisphere. We conducted phylogenetic and biogeographic analyses for Alangium by integrating data from DNA sequences, morphology, and fossils to evaluate systematic and biogeographic hypotheses. The results largely agree with the traditional classification of four sections within the genus, and suggest sects. Conostigma and Rhytidandra are successive sister taxa to a clade containing sects. Marlea and Alangium. Our results also indicate that the widespread species A. chinense consists of at least two lineages meriting recognition as distinct species. Biogeographic analysis using DIVA and divergence time dating with the Bayesian method (MULTIDIVTIME) resolved the ancestor of Alangium as being in S.E. Asia in the Late Cretaceous. Several intercontinental migrations involving the margin of the Tethys seaway (TESW), the North Atlantic land bridge (NALB) or the Bering land bridge (BLB), and long-distance dispersals are suggested. The results support TESW for plant migration of thermophilic (including evergreen) taxa in the early Tertiary.

A crude organic solvent extract of Alangium cf. longiflorum exhibited potent inhibition of hypoxia-induced HIF-1 transcriptional activity in human U251 glioma cells. Dereplication and bioactivity-guided fractionation, including Sephadex LH-20 and chiral HPLC chromatographies, led to the isolation of tubulosine ( 1), 9-desmethyltubulosine ( 2), and isotubulosine ( 3). Structures were verified by complete (1)H and (13)C assignments using 1D- and 2D-NMR techniques. Tubulosine strongly inhibited HIF-1 transcriptional activity, isotubulosine was devoid of activity, and 9-desmethyltubulosine possessed 6-fold less potency than tubulosine.

Widespread use of synthetic pesticides has resulted in the development of insecticide-resistant populations of pests and harmful effects on human health and the environment. There is a need to identify alternative pest management strategies to reduce our reliance on conventional chemical pesticides. In recent years the use of botanical pesticides for protecting crops from insect pests has assumed greater importance. Methanol extract of Alangium salvifolium (L.f.) Wang has potential insecticidal activity against Spodoptera litura Fab. The active fractions were identified through chromatographic techniques as F-IV (Rf value=0.45) and F-VI (Rf value=0.63) and were subjected to GC-MS (GCMATE II). Fifty, 100 and 200ppm of active fractions were applied to fourth instar larvae and the mortality increased with higher concentrations. Relative consumption rate, relative growth rate, efficiency of conversion of ingested food and efficiency of conversion of digested food values all decreased in treated larvae, but approximate digestibility rate increased after treatment. The hydrolytic enzymes, such as acid phosphatase, alkaline phosphatase and the glycolytic enzyme lactate dehydrogenase were inhibited in treated larvae compared with controls. The histopathology study revealed that the epithelial columnar cells were enlarged, completely atrophied; intercellular spaces were swollen, and also noted a cytoplasmic ooze of cell material that mixed with food column. The present study clearly showed the active fractions from A. salvifolium as potential botanicals to control the larvae of S. litura. This is the first report for nutritional indices, enzymatic activities and histological effects of A. salvifolium chemical constituents against S. litura. Thus probably, this will be used as an alternative for synthetic pesticides against the polyphagous pest like S. litura.