NCI-H460 Cancer Cell Lines Research Articles

The effects of cordycepin on the cell proliferation, migration and apoptosis in human lung cancer cell lines A549 and NCI-H460.

Our study aimed to evaluate the effect of cordycepin on human lung cancer cell lines A549 and NCI-H460. Human lung cancer A549 cells and NCI-H460 cells were treated with different concentrations of cordycepin for different times. Cells incubated without cordycepin were defined as a control. The cell proliferation, migration and apoptosis were, respectively, determined by MTT assay, transwell migration assay and flow cytometry. Additionally, the expression levels of related proteins associated with cell cycle, epithelial-mesenchymal transition (EMT) and apoptosis were examined. The survival rate of A549 cells and NCI-H460 cells treated with cordycepin significantly decreased compared with untreated cells in a concentration-dependent manner, while the apoptosis rate increased. The migration number of cells treated with cordycepin significantly decreased as the increase in concentration. qRT-PCR and Western blot analysis showed that the aberrant expression of related molecules associated with cell cycle, migration and apoptosis was observed in the lung cancer cells, such as cyclin B, cyclin E, MMP-9, caspase-3 and Bcl-2. Cordycepin may exert inhibitory effects on the development of human lung cancer via inhibiting cell proliferation, suppressing migration and inducing apoptosis, suggesting that cordycepin may have therapeutic potential for the treatment of this disease.

The self-assembly of a camptothecin-lysine nanotube

A simple, low molecular weight camptothecin-lysine conjugate is reported to self-assemble into nanotubes with diameters of 70–100nm and a drug loading level of 60.5%. The nanotubes exhibited promising in vitro cytotoxicity against cancer cell lines A549, NCI-H460 and NCI-H23. The release of active camptothecin was highly dependent on conjugate concentration, temperature and pH of the solution.

The Synthesis and Cytotoxicity of Novel Thiophene Derivatives Derived from 2-(4-Oxo-4,4-Dihydrothiazol-2-yl) Acetonitrile

The reaction of the 2-(4-oxo-4,4-dihydrothiazol-2-yl)acetonitrile 1 with cyaclopentanone (2) afforded the condensed product 3. The latter underwent a series of heterocyclizations through its reaction with different reagents. Moreover, compound 1 underwent the Gewald’s thiophene to afford compounds 15 and 17. The reaction of either hydrazine hydrate or phenylhydrazine with compound 17 gave the hydrazide derivatives 19a and 19b, respectively. The cytotoxicity of the newly synthesized products was measured towards the three cancer cell lines MCF-7, NCI-H460 and SF-268. The study showed that compounds 3, 5, 9c, 11, 13a, 13c, 17 and 19b were the most active compounds towards the three cancer cell lines.

An anthraquinone derivative from Luffa acutangula induces apoptosis in human lung cancer cell line NCI-H460 through p53-dependent pathway

The current study was designed to evaluate the in vitro antiproliferative activity of 1,8-dihydroxy-4-methylanthracene-9,10-dione (DHMA) isolated from the Luffa acutangula against human non-small cell lung cancer cell line (NCI-H460). Induction of apoptosis and reactive oxygen species (ROS) generation was determined through fluorescence microscopic technique. Quantitative real-time PCR and western blotting analysis was carried out to detect the expression of pro-apoptotic (p53, p21, caspase-3, Bax, GADD45A, and ATM) and anti-apoptotic (NF-κB) proteins in NCI-H460 cell line. In silico studies also performed to predict the binding mechanism of DHMA with MDM2-p53 protein. The DHMA inhibited the cell viability of NCI-H460 cells in a dose-dependent manner with an IC50 of about 50 µg/ml. It significantly reduced cell viability correlated with induction of apoptosis, which was associated with ROS generation. The apoptotic cell death was further confirmed through dual staining and DNA fragmentation assay. DHMA significantly increased the expression of anti-apoptotic protein such as p53, p21, Bax, and caspase-3 but downregulated the expression of NF-κB in NCI-H460 cell line. In silico studies demonstrate that DHMA formed hydrogen bond interaction with key residues Trp26, Phe55 and Lys24 by which it disrupt the binding of p53 with MDM2 receptor. These findings suggested that DHMA induces apoptosis in NCI-H460 via a p53-dependent pathway. This the first study on cytotoxic and apoptosis inducing activity of DHMA from L. acutangula against NCI-H460 cell line. Therefore, DHMA has therapeutic potential for lung cancer treatment.

The isolation of two new lanostane triterpenoid derivatives from the edible mushroom Astraeus asiaticus

Two lanostane triterpenoid derivatives, astrasiaone (2), (22S, 25R, 26R)-26-methoxy-22-26-epoxylanost-8-en-3-one, and astrasiate (3), (3α, 22S, 25R)-3, 22-dihydroxylanost-8-en-26 -oate, together with six known compounds, astraodorol (1), artabotryol B (4), artabotryol C1 (5), 6-dehydrocerevisterol (6), ergosterol (7) and hypaphorine (8) were isolated from the edible mushroom Astraeus asiaticus. 3 and 4 exhibited weak cytotoxicity against KB and NCI-H187 cancer cell lines. A comparison of the structures of 2 and 3 to that of 1, 4 and 5 suggest that these two new compounds could be the intermediate form that occurs during biogenesis.

Two new bioactive polyketides from Curvularia trifolii, an endolichenic fungus isolated from Usnea sp., in Sri Lanka

Two new polyketides (compounds 1 and 2) were isolated from the EtOAc extract of an endolichenic fungus, Curvularia trifolii obtained from Usnea sp. in Sri Lanka. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, MS, 1D NMR and 2D NMR). The bioactivity of the compounds 1 and 2 were studied using DPPH antioxidant assays and they showed radical scavenging activity with IC50 values of 4.0 ± 2.6 and 1.3 ± 0.2 mg/mL, respectively. The radical scavenging activity of compound 2 was higher than that of compound 1 and it was comparable to BHT. Moreover, the new compounds 1 and 2 were evaluated for their anti-inflammatory activity, and only compound 2 exhibited a significant activity comparable to the standard antiinflammatory drug, aspirin. Compound 1 was evaluated for the inhibition of cell proliferation in a panel of five cancer cell lines NCI-H460, MCF-7, SF-268, PC-3M and MIA Pa Ca-2, and exhibited > 90 % inhibitory activity at 5 μg/mL with all of the above cell lines. J.Natn.Sci.Foundation Sri Lanka 2015 43 (3): 217-224

The Chemical Constituents and Biological Activities of the Essential Oil and the Extracts from Leaves of Gynura divaricata (L.) DC. Growing in Thailand

The chemical constituents of the essential oil from the leaves of Gynura divaricata (L.) DC. were investigated by GC-FID and GC-MS. Seventeen compounds, representing 97.1 % of the chromatographical fraction of the oil, were detected. The major constituents, cubenol (65.7 %) and spathulenol (6.4 %), were isolated using column chromatography and identified by NMR and MS analysis. The antioxidant, cytotoxicity and antimicrobial activities of the essential oil, the hexane, dichloromethane and methanol extracts of G. divaricata leaves were investigated. The essential oil and the crude extracts showed antioxidant activity using the ABTS and DPPH methods, respectively. The essential oil exhibited significant cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines with the IC values of 5.79, 47.44 and 17.65 µg/mL, respectively and had a MIC of 50 μg/mL against Mycobacterium tuberculosis H37Ra. Cubenol had an IC50 value of 45.37 µg/mL against the NCI-H187 cancer cell line. All extracts were non-cytotoxic against Vero cells. The essential oil and the extracts showed antimicrobial activity using the disc diffusion assay. The methanol extract was the most potent of the three extracts.

Antimalarial and cytotoxic constituents of Xylaria cf. cubensis PK108

Xylaria cf. cubensis PK108 was identified by its distinctive morphological characteristics and its internal transcribed spacers sequence analysis. The chromatographic separation and structural elucidation based on spectroscopic analysis of fungal crude extracts led to 10 compounds; tryptoquivaline L (1), fiscalin C (2), epi-fiscalin C (3), cytochalasin D (4), ergosterol (5), ergosterol peroxide (6), chevalone C (7), xylaranol B (8), helvolic acid (9) and cyclo-(l-Pro-l-Leu) (10). The bioassay screening showed that 4 displayed cytotoxicity against KB and NCI-H187 cancer cell lines with IC50 values of 3.25 and 5.95 μg mL− 1. 6 exhibited cytotoxicity against NCI-H187 with an IC50 value of 5.81 μg mL− 1. 7 and 9 showed antimalarial activity with IC50 values of 25.00 and 6.25 μg mL− 1, respectively. This result establishes Xylaria as broad spectrum bioactive compound producers.

New Metabolites from the South China Sea Sponge Diacarnus megaspinorhabdosa.

Chemical investigation on CH2Cl2 extract of the marine sponge Diacarnus megaspinorhabdosa resulted in the isolation of two new farnesylacetone derivatives 1-2, a new γ-lactone 3, a known dinorditerpenone 4 and four known norsesterterpene peroxides 5-8. Their structures were elucidated by using one and two dimensional (1D and 2D)-NMR, high resolution-electrospray ionization (HR-ESI)-MS, and comparison with the literature. Compounds 1 and 2 were cis/trans-olefinic isomers and determined through nuclear Overhauser effect spectroscopy (NOESY) experiment. The absolute configuration of 3 was established by comparison of circular dichroism (CD) data with known lactones. The cytotoxic activities of the compounds were evaluated against five cancer cell lines, and compound 3 showed moderate cytotoxicity activities against cancer cell lines HeLa, H446, NCI-H460, SGC-7901 and MCF-7, with IC50 values in the range of 18.5 to 47.1 µM.

A new ursane and a new oleanane triterpene acids from the whole plant of Spermacoce latifolia

A phytochemical study on the whole plant of Spermacoce latifolia led to the isolation of a new ursane triterpene acid, 3β,6β,23-trihydroxy-urs-12,20(30)-dien-28-oic acid (1), and a new oleanane triterpene acid, 3β,6β,29-trihydroxy-olean-12-en-28-oic acid (2), together with seven known triterpenic acids (3–9). Their structures were established on the basis of detailed spectroscopic analysis, including one- and two-dimensional NMR, ESI–MS and HR–ESI–MS techniques. All the compounds were isolated from S. latifolia for the first time. Compounds 3, 5, 6 and 9 were found to show in vitro growth inhibitory activity against three assayed human cancer cell lines MCF-7, NCI-H460 and HepG-2 with IC50 values from 9.53 to 80.20mM. Compounds 1 and 3–9 were further revealed to show significantly in vitro α-glucosidase inhibitory activity with IC50 values from 0.009 to 0.422mM, most of which were more potent than the reference compound acarbose (IC50 0.409mM).

Design and synthesis of new 2-arylnaphthyridin-4-ones as potent antitumor agents targeting tumorigenic cell lines.

To develop new anticancer drug candidates from 2-arylnaphthyridin-4-one (AN), we have designed and synthesized a series of 3'-hydroxy and 6-hydroxy derivatives of AN. The results of cytotoxicity screening indicated that the replacement of the 3'-methoxy moiety on the C-ring phenyl group of AN (6a-e) with 3'-hydroxy (7a-e) made no significant effect on the inhibitory activity against HL-60, Hep3B and NCI-H460 cancer cell lines. On the other hand, replacing the 6-methoxy group on the A-ring of AN (6g-i) with a 6-hydroxy group (7g-i) resulted in reduced inhibitory activity against the above three cancer cell lines. Among the above-mentioned target compounds, 2-(3-hydroxyphenyl)-5-methyl-1,8-naphthyridin-4(1H)-one (7a) demonstrated the greatest potency and the best selectivity toward tumorigenic cancer cell lines. In a 7a preliminary mechanism of action study in Hep3B hepatoma cells, 7a showed the effects on microtubules followed by cell cycle arrest and sequentially led to apoptosis. In addition, a phosphate prodrug (11) of 7a exhibited significant antitumor activity when tested in a Hep3B xenograft nude mice model. Since compound 11 has demonstrated good development potential, it is recommended for further preclinical studies.

Bioassay-guided isolation and identification of bioactive compound from aerial parts of Luffa acutangula against lung cancer cell line NCI-H460

Luffa acutangula (Cucurbitaceae) is widely used as a traditional medicine in India and was reported to possess various pharmacological activities including its anti-proliferative effects. In this study, the bioactive compound of ethanolic extract of L. acutangula (LA) was isolated using bioassay-guided approach. Five major fractions were collected and evaluated for their anti-proliferative activity against non-small cell lung cancer cells (NCI-H460). Among the test fractions, the fraction LA/FII effectively decreased the growth of cancer cells with IC50 values of 10 µg/ml concentration. Furthermore, it significantly increased intracellular reactive oxygen species and decreased the mitochondrial membrane potential. The apoptogenic activity of fraction LA/FII was confirmed by cell shrinkage, membrane blebbing and formation of apoptotic bodies. A single bioactive compound was isolated from the active faction, LA/FII and subsequently identified as 1,8 dihydroxy-4-methylanthracene 9,10-dione (compound 1) by comparing its spectral data [Ultraviolet (UV), Infrared (IR), Nuclear magnetic resonance (NMR) and Electrospray Ionization-Mass Spectroscopy (ESI-MS)] with literature values. This is the first report on the isolation of compound 1 from this plant.

Chemical constituents and cytotoxic activities from the root and the stem of Reevesia formosana

In our previous studies, we have reported 13 new cardenolide glycosides with potent cytotoxicities, reevesiosides A-I and epi-reevesiosides F-I from the root of Reevesia formosana (Sterculiaceae). Continuing investigation of the root and the stem of this species led to the isolation of three new lignanoids, reevesic acid, reevesilignan, and reevesiacoumarin, two new sesquiterpenes, reevesiterpenol A and reevesiterpenol B, one new triterpene, 3α,27-di-O-caffeoylbetulinic acid, along with 37 known compounds including nine lignanoids, eight triterpenes, six steroids, four sesquiterpenes, three coumarins, three cardenolide glycosides, two benzenoids, one proanthocyanidin, and Q10. Three additional known cardenolide glycosides, strophathojavoside, strophalloside, and ascleposide isolated from the root of this plant also displayed potent cytotoxicity against the MCF-7, NCI-H460, and Hep G2 cancer cell lines, with IC50 values of 0.767 ± 0.031, 0.175 ± 0.011, and 0.649 ± 0.06; 3.456± 0.130, 0.62 ± 0.059, and 2.593 ± 0.132; 0.166 ± 0.015, 0.037 ± 0.002, and 0.374 ± 0.020µM, respectively. The new triterpene, 3α,27-di-O-caffeoylbetulinic acid isolated from the stem of this species showed a moderate cytotoxicity against NCI-H460 cancer cell line. The structures of these compounds were elucidated by spectroscopic techniques. Keywords: Reevesia formosana, Sterculiaceae, Root, Stem, Cardenolide glycoside, Cytotoxicity

Design, synthesis, 3D pharmacophore, QSAR, and docking studies of carboxylic acid derivatives as Histone Deacetylase inhibitors and cytotoxic agents

In this study, five series of (E)-6-(4-substituted phenyl)-4-oxohex-5-enoic acids IIb–f (E), (E)-3-(4-(substituted)-phenyl)acrylic acids IIIa–g (E), 4-(4-(substituted)phenylamino)-4-oxobutanoic acids VIa,b,e, 5-(4-(substituted)phenylamino)-5-oxopentanoic acids VIIa,f and 2-[(4-(substituted)phenyl) carbamoyl]benzoic acids VIIIa,e were designed and synthesized. Selected compounds were screened in vitro for their cytotoxic effect on 60 human NCI tumor cell lines. Compound IIf (E) displayed significant inhibitory activity against NCI Non-Small Cell Lung A549/ATCC Cancer cell line (68% inhibition) and NCI-H460 Cancer cell line (66% inhibition). Moreover, the final compounds were evaluated in vitro for their cytotoxic activity on HepG2 Cancer cell line in which histone deacetylase (HDAC) is overexpressed. Compounds IIc (E), IIf (E), IIIb (E), and IIIg (E) exhibited the highest cytotoxic activity against HepG2 human cancer cell lines with IC50 ranging from 2.27 to 10.71μM. In addition, selected compounds were tested on histone deacetylase isoforms (HDAC1–11). Molecular docking simulation was also carried out for HDLP enzyme to investigate their HDAC binding affinity. In addition, generation of 3D-pharmacophore model and quantitative structure activity relationship (QSAR) models were combined to explore the structural requirements controlling the observed cytotoxic properties.

Cancer cell growth inhibitory effect of bee venom via increase of death receptor 3 expression and inactivation of NF-kappa B in NSCLC cells.

Our previous findings have demonstrated that bee venom (BV) has anti-cancer activity in several cancer cells. However, the effects of BV on lung cancer cell growth have not been reported. Cell viability was determined with trypan blue uptake, soft agar formation as well as DAPI and TUNEL assay. Cell death related protein expression was determined with Western blotting. An EMSA was used for nuclear factor kappaB (NF-κB) activity assay. BV (1–5 μg/mL) inhibited growth of lung cancer cells by induction of apoptosis in a dose dependent manner in lung cancer cell lines A549 and NCI-H460. Consistent with apoptotic cell death, expression of DR3 and DR6 was significantly increased. However, deletion of DRs by small interfering RNA significantly reversed BV induced cell growth inhibitory effects. Expression of pro-apoptotic proteins (caspase-3 and Bax) was concomitantly increased, but the NF-κB activity and expression of Bcl-2 were inhibited. A combination treatment of tumor necrosis factor (TNF)-like weak inducer of apoptosis, TNF-related apoptosis-inducing ligand, docetaxel and cisplatin, with BV synergistically inhibited both A549 and NCI-H460 lung cancer cell growth with further down regulation of NF-κB activity. These results show that BV induces apoptotic cell death in lung cancer cells through the enhancement of DR3 expression and inhibition of NF-κB pathway.

ARRY-334543 reverses multidrug resistance by antagonizing the activity of ATP-binding cassette subfamily G member 2.

ARRY-334543 is a small molecule inhibitor of ErbB1 and ErbB2 tyrosine kinases. We conducted this study to determine whether ARRY-334543 can enhance the efficacy of conventional anticancer drugs through interaction with ABC transporters. Lung cancer cell line NCI-H460 and its ABCG2-overexpressing NCI-H460/MX20, as well as the ABCG2-, ABCB1-, and ABCC10-overexpressing transfected cell lines were used for the reversal study. Our results demonstrated that ARRY-334543 (1.0 μM) significantly reversed ABCG2-mediated multidrug resistance (MDR) by directly inhibiting the drug efflux function of ABCG2, resulting in the elevated intracellular accumulation of chemotherapeutic drugs in the ABCG2-overexpressing cell lines. In addition, in isolated membranes, ARRY-334543 stimulated ATPase activity and inhibited photolabeling of ABCG2 with [(125)I]-iodoarylazidoprazosin in a concentration-dependent manner indicating that this drug directly interacts at the drug-binding pocket of this transporter. ARRY-334543 (1.0 μM) only slightly reversed ABCB1- and partially reversed ABCC10-mediated MDR suggesting that it exhibits high affinity toward ABCG2. Moreover, homology modeling predicted the binding conformation of ARRY-334543 at Arg482 centroid-based grid of ABCG2. However, ARRY-334543 at reversal concentrations did not affect the expression level of ABCG2, AKT and ERK1/2 and regulate the re-localization of ABCG2. We conclude that ARRY-334543 significantly reverses drug resistance mediated by ABCG2.

A new benzyl ester and ergosterol derivatives from the fungus Gymnoascus reessii

A new benzyl ester, reessiate (1), anthraquinone, islandicin (2), ergosterol and seven ergosterol derivatives (3–9) were isolated from the fungus Gymnoascus reessii. All structures were identified by spectroscopic methods. This is the first report of their isolation from this fungus. Compounds 4–7 and 9 exhibited antimalarial activity against Plasmodium falciparum with IC50 values in the range of 3.3–4.5 μg/mL. In addition, 4 showed cytotoxicity against KB, MCF7 and NCI-H187 cancer cell lines. It was found that 4 has cytotoxic effect to MCF7 (IC50 = 7.9 μg/mL) lower than Doxorubicin (IC50 = 8.5 μg/mL).

Hybrid probes of aromatic amine and barbituric acid: highly promising leads for anti-bacterial, anti-fungal and anti-cancer activities

Today, cancer and resistant microbes remain one of the most deadly diseases in the world. In search of novel anti-cancer and anti-microbial probes, a series of newly hybrid molecules is synthesized by combining the structural features of aromatic amines and barbituric acid, using the concept of green chemistry. This approach was accomplished efficiently using water as the greener solvent and in the absence of catalyst to give the corresponding adducts. All newly synthesized compounds were characterized by spectral analysis FT-IR, 1H NMR, 13C NMR, HMBC and Elemental Analysis. Evaluations of these probes over four human cancer cell lines (Breast adenocarcinoma cancer cell line MCF-7, Non-small cell lung cancer cell line NCI-H460, CNS cancer cell line SF-268 and fibroblast cancer cell line WI-38), anti-microbial activity against five bacterial strains (S. pyogenes MTCC 442 and S. aureus MTCC 96 as the gram positive, E. coli MTCC 443, P. aeruginosa MTCC 424 and K. pneumoniae MTCC 109 as the gram negative) and four fungal strains (C. albicans MTCC 227, A. clavatus MTCC 1323, T. rubrum MTCC 296 and Penicillium wild strain). Out of set of nineteen probes, three probes show significant anti-cancer activities against MCF-7, NCI-H460 and SF-268, whereas sixteen probes exhibit potent anti-tumour activity against WI-38 cell lines. Within anti-microbial bioassay, three molecules exhibited significant activity against both the gram-positive as well as gram-negative bacteria, whereas two compounds showed highly potent activity against T. rubrum fungi, while three molecules were found to be equipotent against T. rubrum as a fungal strain.

Cytotoxic Carbazole Alkaloids from the Stems of Murraya koenigii

Murraya koenigii is a tropical to subtropical small tree belonging to the Rutaceae family. The plant is native to India and is distributed in most of Southern Asia. The leaves of this plant are highly aromatic, and young leaves are used as a vegetable herb in the Southern part of Thailand. Various parts of the plant have been reported as a folk medicine. The leaves, stems, and roots are used externally in skin eruptions and bites of venomous animals, while the barks and roots are used as a stimulant [1]. Previous phytochemical investigations led to the isolation of a number of carbazole alkaloids, some of which have been indicated for their antioxidant, antitumor, antimicrobial, antiinflammatory, antitrypanocidal, and mosquitocidal activities [2–5]. In the course of our ongoing search for bioactive compounds from Rutaceae medicinal plants, we found that the EtOAc extract of the stems of M. koenigii exhibited cytotoxicity against three human cancer cell lines, including oral cavity cancer (KB), breast cancer (MCF7), and small cell lung cancer (NCI-H187). In this paper, we describe the isolation and cytotoxic activity of the crude extract and pure carbazole alkaloids from the stems of M. koenigii. The EtOAc extract of M. koenigii stems showed cytotoxic activity against KB, MCF7, and NCI-H187 cancer cell lines, with IC50 values of 35.54, 17.56, and 14.86 g/mL, respectively. The activity-guided investigation of this extract resulted in the identification of nine earlier isolated carbazole alkaloids from M. koenigii, including murrayanine (1) [6], koenoline (2) [7], mahanimbinol (3) [8], girinimbine (4) [9], mahanimbine (5) [9], furostifoline (6) [10], murrayazoline (7) [9], murrayaquinone A (8) [9], and murrayazolidine (9) [11]. Compound 6 was isolated for the first time from M. koenigii. All structures were characterized by spectroscopic methods and comparison of their physical and spectral data with reported values. Murrayanine (1). Yellow solid, mp 158–161 C. 1H NMR (400 MHz, CDCl3, , ppm, J/Hz): 10.04 (1H, s, CHO), 8.69 (1H, br.s, NH), 8.18 (1H, br.s, H-2), 8.10 (1H, d, J = 8.0, H-5), 7.51 (1H, m, H-8), 7.49 (1H, m, H-7), 7.45 (1H, br.s, H-2), 7.31 (1H, m, H-6), 4.06 (3H, s, OCH3). 13C NMR (100 MHz, CDCl3, , ppm): 191.8 (CHO), 146.0 (C-1), 139.4 (C-8a), 134.0 (C-8b), 130.1 (C-3), 126.6 (C-7), 123.6 (C-4a and C-4b), 120.7 (C-5 and C-6), 120.4 (C-4), 111.5 (C-8), 103.5 (C-2), 55.8 (OCH3). Koenoline (2). Brown viscous oil. 1H NMR (400 MHz, CDCl3, , ppm, J/Hz): 8.28 (1H, br.s, NH), 8.03 (1H, d, J = 8.0, H-5), 7.65 (1H, br.s, H-4), 7.46 (1H, br.d, J = 8.0, H-8), 7.41 (1H, m, H-7), 7.22 (1H, m, H-6), 6.95 (1H, br.s, H-2), 4.80 (2H, s, H-1 ), 4.01 (3H, s, OCH3), 2.17 (1H, br.s, OH). 13C NMR (100 MHz, CDCl3, , ppm): 145.7 (C-1), 139.2 (C-8a), 132.7 (C-3), 129.1 (C-8b), 125.8 (C-7), 125.7 (C-4a), 124.0 (C-4b), 120.5 (C-5), 119.5 (C-6), 111.7 (C-4), 111.0 (C-8), 105.6 (C-2), 66.5 (C-1 ), 55.5 (OCH3). Mahanimbinol (3). Brown viscous oil. 1H NMR (400 MHz, CDCl3, , ppm, J/Hz): 7.93 (1H, br.d, J = 7.6, H-5), 7.85 (1H, br.s, NH), 7.68 (1H, s, H-4), 7.36 (1H, br.d, J = 8.0, H-8), 7.30 (1H, br.t, J = 7.6, 7.2, H-6), 7.17 (1H, br.t, J = 7.2, H-7), 5.37 (1H, t, J = 6.8, H-2 ), 5.21 (1H, br.s, OH), 5.07 (1H, m, H-6 ), 3.62 (2H, d, J = 6.8, H-1 ), 2.40 (3H, s, CH3-3), 2.12 (4H, m, H-4 and -5 ), 1.90 (3H, s, CH3-9 ), 1.66 (3H, s, CH3-8 ), 1.59 (3H, s, CH3-10 ). 13C NMR (100 MHz, CDCl3, , ppm): 151.2 (C-2), 139.4 (C-8a), 139.0 (C-3 ), 138.4 (C-8b), 132.1 (C-7 ), 124.2 (C-6), 123.6 (C-4b and C-6 ), 121.3 (C-2 ), 119.3 (C-4, C-5 and C-7), 117.0 (C-3), 116.6 (C-4a), 110.3 (C-8), 107.8 (C-1), 39.6 (C-4 ), 26.4 (C-5 ), 25.6 (CH3-8 ), 24.7 (C-1 ), 17.7 (CH3-10 ), 16.5 (CH3-3), 16.4 (CH3-9 ).

Isolation, Synthesis and Biological Evaluation of Phenylpropanoids from the Rhizomes of Alpania galanga

Bioactivity guided investigation of the DCM: MeOH (1:1) extract from the rhizomes of Alpinia galanga led to the isolation of phenylpropanoids (1-9) and their structures were established by 1H NMR, 13C NMR, IR a nd LC-MS/MS. Th ese compounds have b een evaluated for their in vitro anticanceractivity against the human cancer cell lines A549 (lung cancer), Colo-205 (colon cancer), A431 (skin cancer), NCI H460 (lung cancer), PC-3 (prostate cancer), and HT-29 (colon cancer). Compounds 4 and 9 showed potent anticancer activity (ranging from 1.3-19.7 microg/mL) against all the tested cancer cell lines. In addition, an asymmetric synthesis of acetoxychavicol acetate (1) and trans-p-coumaryl alcohol (4) has been accomplished in six steps starting from readily available p-hydroxybenzaldehyde for the first time. Grignard reaction and Sharpless kinetic resolution reactions were utilized as the key steps to install the basic core.