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1.
Desi Harneti Roekmiati Tjokronegoro Agus Safari Unang Supratman Xe-Min Loong Mat Ropi Mukhtar Khalit Mohamad Khalijah Awang Hideo Hayashi 《Phytochemistry letters》2012,5(3):496-499
Two new dammarane triterpenoids, aglinone (1) and aglinin E (20S,24S-epoxy-25-hydroxy-1-en-dammarene) (2) along with three known compounds, 3-epiocotillol (3), aglinin A (4), and eichlerianic acid (5), were isolated from the bark of Aglaia smithii. The chemical structures of the new compound were elucidated on the basis of spectroscopic data interpretation. All the compounds isolated were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1, 2, 4 and 5 showed cytotoxicity against P-388 murine leukemia cells with IC50 values of 21, 42, 34, and 11 μg/mL, respectively. 相似文献
2.
Two new protolimonoid compounds, namely, argentinin A (1) and B (2) along with five known triterpenoid compounds, dammar-24-en-3α-ol (3), 3-epi-cabraleahydroxy lactone (4), (E)-25-hydroperoxydammar-23-en-3β,20-diol (5), mixture of eichlerianic acid and shoreic acid (6a and 6b), and dammar-24-en-3α,20-diol (7), were isolated from the stem bark of Aglaia argentea. The structure of new compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as high-resolution mass spectrometric analysis. All of the compounds were tested for their cytotoxic effects against P-388 murine leukemia cells in vitro. Among those isolated compounds, argentinin A (1) showed the strongest activity with an IC50 value of 1.27 μg/mL (3.05 μM). 相似文献
3.
《Bioorganic & medicinal chemistry letters》2014,24(2):473-475
Two new kelsoane-type sesquiterpenes, namely kelsoenethiol (1) and dikelsoenyl ether (2), were obtained from the Formosan soft coral Nephthea erecta. Their structures were elucidated through extensive spectroscopic analyses, ESI orbitrap mass and quantum chemical calculations (QCC). The cytotoxicity against A-459 (human lung carcinoma), P-388 (mouse lymphocytic leukemia), and HT-29 (human colon adenocarcinoma) cancer cell lines of 1 and 2 was evaluated in vitro. Compound 1 showed cytotoxicity against P-388 and HT-29 cells with ED50s of 1.3 and 1.8 μg/mL, respectively. 相似文献
4.
Seven eremophilane-type sesquiterpenes (1–7), six cycloartane derivatives (8–13) and α-amyrin acetate (14) were isolated from the leaves of the far-eastern plant Ligularia alticola Worosch. (Family Asteraceae). (4S,5R,8S,10R)-8-Ethoxyeremophil-7(11)-en-12(8)-olide (1), 8α,11-epidioxy-8β-methoxyeremophil-6-ene (2) and 29-norcycloartan-3α-ol (8) have not been previously reported. Fukinone α-epoxide (3) was isolated for the first time from a natural source. The structures of all the compounds were established by the extensive analysis of their 1D and 2D NMR spectra and HR ESI mass spectrometry. The absolute stereochemistry of 1 was determined by comparison of theoretical and experimental ECD spectra with the application of B3LYP-TDDFT and B3LYP-GIAO calculations as well as by NMR spectroscopy. Compound 1 showed cytotoxic action against human cancer HL-60, Raji, and THP-1 cell lines (IC50 12.6, 6.0 and 6.9 μM, respectively). Compounds 2 and 4 demonstrated significant cytotoxic activities against HL-60 (IC50 2.8 and 5.8 μM, respectively) and Raji cells (IC50 2.9 and 4.2 μM, respectively). Compound 6 was cytotoxic against Raji cells (IC50 4.6 μM). None of tested compounds were cytotoxic against RAW 264.7 cells. Compounds 1 and 4–7 significantly decreased intracellular ROS levels, induced by endotoxic LPS from Escherichia coli in RAW 264.7 murine macrophages. 相似文献
5.
《Bioorganic & medicinal chemistry》2014,22(14):3629-3641
The efficient synthesis of a new series of polyhydroxylated dibenzyl ω-(1H-1,2,3-triazol-1-yl)alkylphosphonates as acyclic nucleotide analogues is described starting from dibenzyl ω-azido(polyhydroxy)alkylphosphonates and selected alkynes under microwave irradiation. Selected O,O-dibenzylphosphonate acyclonucleotides were transformed into the respective phosphonic acids. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses and for cytostatic activity against murine leukemia L1210, human T-lymphocyte CEM and human cervix carcinoma HeLa cells. Compound (1S,2S)-16b exhibited antiviral activity against Influenza A H3N2 subtype (EC50 = 20 μM—visual CPE score; EC50 = 18 μM—MTS method; MCC >100 μM, CC50 >100 μM) in Madin Darby canine kidney cell cultures (MDCK), and (1S,2S)-16k was active against vesicular stomatitis virus and respiratory syncytial virus in HeLa cells (EC50 = 9 and 12 μM, respectively). Moreover, compound (1R,2S)-16l showed activity against both herpes simplex viruses (HSV-1, HSV-2) in HEL cell cultures (EC50 = 2.9 and 4 μM, respectively) and feline herpes virus in CRFK cells (EC50 = 4 μM) but at the same time it exhibited cytotoxicity toward uninfected cell (MCC ⩾ 4 μM). Several other compounds have been found to inhibit proliferation of L1210, CEM as well as HeLa cells with IC50 in the 4–50 μM range. Among them compounds (1S,2S)- and (1R,2S)-16l were the most active (IC50 in the 4–7 μM range). 相似文献
6.
Fan JT Su J Peng YM Li Y Li J Zhou YB Zeng GZ Yan H Tan NH 《Bioorganic & medicinal chemistry》2010,18(23):8226-8234
Six new (rubiyunnanins C–H, 1–6) and five known (7–11) cyclic hexapeptides were isolated from the roots of Rubia yunnanensis (Franch.) Diels. The structures and stereochemistry of 1–6 were established by extensive spectroscopic analyses and chemical methods. All compounds (1–11) not only exhibited cytotoxic activities against a panel of eleven cancer cell lines with IC50 values ranging from 0.001 to 56.24 μM, but also exerted inhibitory activities against nitric oxide (NO) production in LPS and IFN-γ-induced RAW 264.7 murine macrophages with IC50 values ranging from 0.05 to 12.68 μM. Furthermore, this is the first time it is being reported that compounds 2 and 7–10 significantly inhibited TNF-α-induced NF-κB activation in HEK-293-NF-κB luciferase stable cells with IC50 values of 35.07, 0.03, 1.69, 12.64 and 1.18 μM, respectively. 相似文献
7.
Four nor-β-patchoulene sesquiterpenoids including three new compounds (1–3) and a new natural product (4) were isolated from the essential oil of the leaves and stems of Pogostemon cablin. Their structures were elucidated by detailed spectroscopic analysis, using 1D- and 2D-NMR techniques. This is the first report of 4-nor-β-patchoulenes from plants. All isolates were evaluated for the cytotoxic activities on human cancer cells in vitro. Compound 3 showed weak cytotoxic activities against NCI-H1975 and HePG-2 with IC50 values of 49.9 μg/mL and 56.0 μg/mL, respectively. 相似文献
8.
Fang Yao Qin-Lan Song Lei Zhang Gui-Sheng Li Sheng-Jun Dai 《Phytochemistry letters》2013,6(3):453-456
In our continuing effort to discover more new cytotoxic sesquiterpenoid from Solanum lyratum collected from different districts of China, three new sesquiterpenoids, attributable to eudesmane-type (1, named solajiangxin D) and vetispirane-type (2–3, named solajiangxins E and 2-hydroxysolajiangxin E), respectively, were isolated. Their structures were elucidated on the basis of integrated spectroscopic techniques, mainly HR-FABMS, 1D and 2D NMR (1H–1H COSY, HMQC, HMBC and ROESY). In vitro, compounds 1–3 were found to show significant cytotoxicities against three human cancer lines (P-388, HONE-1, and HT-29), and gave ED50 values in the range 2.1–3.7 μg/ml. 相似文献
9.
Jorge A. Moreno-Escobar Laura Alvarez Verónica Rodríguez-López Silvia Marquina Bahena 《Phytochemistry letters》2013,6(4):610-613
Fractionation guided by the cytotoxic activity of the methanolic extract of Veronica americana led to the isolation of two new iridoids identified as 4β-hydroxy-6-O-(p-hydroxybenzoyl)-tetrahydrolinaride (1) and 10-O-protocatechuyl-catalpol (2), together with four known aromatic acids, veratric acid (3) p-methoxybenzoic acid (4), p-hydroxybenzoic acid (5) and protocatechuic acid (6). The structure of these compounds was determined by spectroscopic analysis. Iridoid glycosides 1 and 2 showed selective cytotoxic activity against the human cancer cell lines HF-6 (IC50 = 0.031 and 0.066 μM, respectively) and PC-3 (IC50 = 0.721 and 0.801 μM, respectively), with less sensitivity in normal MRC-5 cells (IC50 = 77.103 and 1451.562 μM, respectively). Compound 1 was 9.9 times more potent than camptothecin against HF-6 cell line, while compound 2 was 4.7 times, more potent, against the same cell line, than camptothecin. The found biological efficacy of 1 and 2 allow us to propose these compounds as candidates for the development of effective anticancer therapeutic agents. 相似文献
10.
Three new sesquiterpenoids, attributable to eudesmane-related (1–2, named septemlobins A–B) and vetispirane-type (3, named septemlobin C), respectively, were isolated from the whole plant of Solanum septemlobum. Their structures were elucidated on the basis of integrated spectroscopic techniques. In vitro, compounds 1–3 were found to show significant cytotoxicities against three cancer cell lines (P-388, HONE-1, and HT-29), and gave IC50 values in the range 3.8–7.5 μM. 相似文献
11.
Hanna Lee YuJin Kim Inho Choi Byung Sun Min Sang Hee Shim 《Bioorganic & medicinal chemistry letters》2010,20(1):288-290
Two novel neo-clerodane diterpenoids, barbatellarines A (1) and B (2), were isolated from the whole plants of Scutellaria barbata, along with the known compound scutebarbatine F (3). The chemical structures and relative stereochemistry of the isolated compounds were established by NMR (1D and 2D) and mass spectroscopic analyses. Compounds 2 and 3 were evaluated for in vitro cytotoxic activity against the HL-60 (human leukemia), MCF7 (human breast cancer), and LLC (Lewis lung carcinoma) cancer cell lines. Compound 2 exhibited weak cytotoxic activity against HL-60 cells, with an IC50 value of 41.4 μΜ. 相似文献
12.
Three new phenolic glycosides (1–3) together with nine known ones were isolated from the roots of Tecoma mollis using DPPH radical scavenging bioassay-guided chromatographic separation. The structures of the new compounds were established using extensive spectroscopic data and HR-MS. The antioxidant, COX-2 inhibition, and cytotoxic activities were evaluated for the isolated compounds. Compound 4 displayed the strongest radical scavenging activity relative to ascorbic acid with IC50 8.7 μM. Compounds 5, 6, and 10 showed promising COX-2 inhibitory action, IC50 values of 11.3 μM, 9.4 μM, and 13.4 μM, respectively. All compounds exhibited weak cytotoxic activity against Hela and A549 cancer cell lines. 相似文献
13.
Shabir H. Lone Khursheed A. Bhat Rabiya Majeed Abid Hamid Mohd A. Khuroo 《Bioorganic & medicinal chemistry letters》2013,23(17):4931-4934
Diverse amino analogs of Ludartin, a cytotoxic guaianolide and a position isomer of an anticancer drug, Arglabin were prepared through Michael type addition at its highly active α-methylene-γ-lactone motif. The semisynthetic derivatives were subjected to sulphorhodamine B cytotoxicity assay against a panel of four different human cancer cell lines viz. lung (A-549), leukemia (THP-1), prostate (PC-3) and colon (HCT-116) to look into structure–activity relationship. Few of the analogs displayed potent selective cytotoxicity compared to the parent molecule-Ludartin (1). (11R)-13-(Diethyl amine)-11,13-dihydroludartin (6) and (11R)-13-(piperidine)-11,13-dihydroludartin (10) showed almost same cytotoxicity against leukemia cell lines (THP-1) as that of parent molecule-Ludartin, but were more active against colon (HCT-116) cancer cells. (11R)-13-(Morpholine)-11,13-dihydroludartin (11) displayed selectively better cytotoxicity against Leukemia cancer cells (THP-1) exhibiting IC50 of 2.8 μM. (11R)-13-(6-Nitroindazole)-11,13-dihydroludartin (17) was four times more potent than Ludartin with selective cytotoxic effects against prostate cancer cells (2.2 μM) while as (11R)-13-(6-nitroindazole)-11,13-dihydroludartin (18) exhibited three-fold selective cytotoxicity for Lung (A-549) cancer cell lines exhibiting IC50 of 2.6 μM. 相似文献
14.
Wen Gu Ting-Ting Miao Da-Wei Hua Xiao-Yan Jin Xu-Bing Tao Chao-Bo Huang Shi-Fa Wang 《Bioorganic & medicinal chemistry letters》2017,27(5):1296-1300
A series of new 1H-benzo[d]imidazole derivatives of dehydroabietic acid were designed and synthesized as potent antitumor agents. Structures of the target molecules were characterized using MS, IR, 1H NMR, 13C NMR and elemental analyses. In the in vitro cytotoxic assay, most compounds showed significant cytotoxic activities against two hepatocarcinoma cells (SMMC-7721 and HepG2) and reduced cytotoxicity against noncancerous human hepatocyte (LO2). Among them, compound 7b exhibited the best cytotoxicity against SMMC-7721 cells (IC50: 0.36 ± 0.13 μM), while 7e was most potent to HepG2 cells (IC50: 0.12 ± 0.03 μM). The cell cycle analysis indicated that compound 7b caused cell cycle arrest of SMMC-7721 cells at G2/M phase. Further, compound 7b also induced the apoptosis of SMMC-7721 cells in Annexin V-APC/7-AAD binding assay. 相似文献
15.
《Phytomedicine》2014,21(12):1651-1657
IntroductionResistance of cancer to chemotherapy is a main cause in treatment failure. Naturally occurring chalcones possess a wide range of biological activities including anti-cancer effects. In this work, we evaluated the antiproliferative activity of three chalcones [4′-hydroxy-2′,6′-dimethoxychalcone (1), cardamomin (2), 2′,4′-dihydroxy-3′,6′-dimethoxychalcone (3)], and four flavanones [(S)-(–)-pinostrobin (4), (S)-(–)-onysilin (5) and alpinetin (6)] toward nine cancer cell lines amongst which were multidrug resistant (MDR) types.MethodsThe resazurin reduction assay was used to detect the antiproliferative activity of the studied samples whilst flow cytometry for the mechanistic studies of the most active molecule (1).ResultsIC50 values in a range of 2.54 μM against CEM/ADR5000 leukemia cells to 58.63 μM toward hepatocarcinoma HepG2 cells were obtained with 1. The lowest IC50 values of 8.59 μM for 2 and 10.67 μM for 3 were found against CCRF-CEM cells leukemia cells, whilst the corresponding values were above 80 μM for 4 and 6. P-glycoprotein-expressing and multidrug-resistant CEM/ADR5000 cells were much more sensitive toward compound 1 than toward doxorubicin and low cross-resistance or even collateral sensitivity was observed in other drug-resistent cell lines to this compound. Normal liver AML12 cells were more resistant to the studied compounds than HepG2 liver cancer cells, indicating tumor specificity at least to some extent. Compound 1 arrested the cell cycle between Go/G1 phase, strongly induced apoptosis via disrupted mitochondrial membrane potential (MMP) and increased production of reactive oxygen species (ROS) in the studied leukemia cell line.ConclusionsChalcone 1 was the best tested cytotoxic molecule and further studies will be performed in order to envisage its possible use in the fight against multifactorial resistant cancer cells. 相似文献
16.
Narsimha Reddy Penthala Purushothama Rao Ponugoti Vinod Kasam Peter A. Crooks 《Bioorganic & medicinal chemistry letters》2013,23(5):1442-1446
A series of novel 5-((1-aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones (3a–z) have been evaluated for in vitro cytotoxicity against a panel of 60 human tumor cell lines. Compound 3k exhibited the most potent growth inhibition against melanoma MDA-MB-435 cells (GI50 = 850 nM), against leukemia SR cancer cells (GI50 = 1.45 μM), and OVCAR-3 (GI50 = 1.26 μM) ovarian cancer cell lines. The structurally related compound 3s had a GI50 value of 1.77 μM against MDA-MB-435 cells. The N-naphthoyl analogue 3t had GI50 values of 1.30 and 1.91 μM against HOP-92 non-small cell lung cancer and MDA-MB-435 melanoma cell lines, respectively. The related analogue 3w had GI50 values of 1.09 μM against HOP-92 non-small cell lung cancer cell lines. Interestingly, docking of the two active molecules 3k and 3w into the active site of COX-2 indicates that these compounds are COX-2 ligands with strong hydrophobic and hydrogen bonding interactions. Thus, compounds 3k, 3t, 3s, and 3w constitute a new class of anticancer/anti-inflammatory agents that may have unique potential for cancer therapy. 相似文献
17.
A series of new pyrrol-2(3H)-ones 4a-f and pyridazin-3(2H)-ones 7a-f were synthesized and characterized using different spectroscopic tools. Some of the tested compounds revealed moderate activity against 60 cell lines. The E form of the pyrrolones 4 showed good cytotoxic activity than both the Z form and the corresponding open amide form. Furthermore, the in vitro cytotoxic activity against HepG2 and MCF-7 cell lines revealed that compounds (E)4b, 6f and 7f showed good cytotoxic activity against HepG2 with IC50 values of 11.47, 7.11 and 14.80 μM, respectively. Compounds (E)4b, 6f, 7d and 7f showed a pronounced inhibitory effect against cellular localization of tubulin. Flow cytometric analysis indicated that HepG2 cells treated with (E)4b showed a predominated growth arrest at the S-phase compared to that of G2/M-phase. Molecular modeling study using MOE® program indicated that most of the target compounds showed good binding of β-subunit of tubulin with the binding free energy (dG) values about −10 kcal/mole. 相似文献
18.
Emmanuel Ngeufa Happi Alain Tadjong Tcho Jovita Chi Sirri Jean Duplex Wansi Beate Neumann Hans-Georg Stammler Jean Wandji Norbert Sewald 《Phytochemistry letters》2012,5(3):423-426
Two new tirucallane triterpenoids, 21-methoxy-21,23-epoxy-tirucalla-7,24-dien-3α-ol (1) and 21-methoxy-21,23-epoxy-tirucalla-7,24-diene-1α,3α-diol (2), together with thirteen known compounds were isolated from the CH2Cl2 extract of the stem bark of Araliopsis synopsis. The structures of the compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data and comparison with previously known analogs. Compounds 1–10 were tested against bacteria, fungi and plant pathogen oomycetes by the paper disk agar diffusion assay resulting in missing to low activities corresponding with MICs > 1 mg/mL. However, compounds 5–10 exhibited high cytotoxic activity against the human Caucasian prostate adenocarcinoma cell PC-3 line, with IC50 8.5–12.5 μM compared to the standard Doxorubicin with IC50 = 0.9 μM, while compounds 1, 3 and 4 showed low activity. 相似文献
19.
Nguyen Huu Tung Chau Van Minh Tran Thu Ha Phan Van Kiem Hoang Thanh Huong Nguyen Tien Dat Nguyen Xuan Nhiem Bui Huu Tai Jae-Hee Hyun Hee-Kyoung Kang Young Ho Kim 《Bioorganic & medicinal chemistry letters》2009,19(16):4584-4588
Two new C29 sterols with a cyclopropane ring at C-25 and C-26, petrosterol-3,6-dione (1) and 5α,6α-epoxy-petrosterol (2), along with petrosterol (3), were isolated from the Vietnamese marine sponge Ianthella sp. The structures of the new compounds were elucidated by comprehensive spectroscopic analyses. Compounds 1?3 showed cytotoxic activities on A549, HL-60, MCF-7, SK-OV-3, and U937 cancer cell lines with IC50 in the range of 8.4–22.6 μM, whereas compounds 1?3 exhibited only weak cytotoxic activities on HT-29 cell. After HL-60 cells were treated with the compounds, several apoptosis events like chromatin condensation and the increase of the population of sub-G1 hypodiploid cells were observed. These data supported that the compounds might have potential for leukemia treatment. 相似文献
20.
Phytochemical investigation of the dichloromethane/methanol (1:1) extract of the roots of Bulbine frutescens led to the isolation of a new xanthone, 8-hydroxy-6-methylxanthone-1-carboxylic acid (1) and a new phenylanthraquinone, 6′,8-O-dimethylknipholone (2) along with six known compounds. The structures were elucidated on the basis of NMR and MS spectral data analyses. The structure of compound 1 was confirmed through X-ray crystallography which was then used as a reference to propose the revision of the structures of six seco-anthraquinones into xanthones. The isolated compounds were evaluated for cytotoxicity against human cervix carcinoma KB-3-1 cells with the phenylanthraquinone knipholone being the most active (IC50 = 0.43 μM). Two semi-synthetic knipholone derivatives, knipholone Mannich base and knipholone-1,3-oxazine, were prepared and tested for cytotoxic activity; both showed moderate activities (IC50 value of 1.89 and 2.50 μM, respectively). 相似文献