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1.
Antiproliferative cardenolide glycosides of Elaeodendron alluaudianum from the Madagascar Rainforest
Yanpeng Hou Shugeng Cao Peggy Brodie Martin Callmander Fidisoa Ratovoson Richard Randrianaivo Etienne Rakotobe Vincent E. Rasamison Stephan Rakotonandrasana Karen TenDyke Edward M. Suh David G.I. Kingston 《Bioorganic & medicinal chemistry》2009,17(6):2215-2218
Bioassay-guided fractionation of an ethanol extract of a Madagascar collection of Elaeodendron alluaudianum led to the isolation of two new cardenolide glycosides (1 and 2). The 1H and 13C NMR spectra of both compounds were fully assigned using a combination of 2D NMR experiments, including 1H–1H COSY, HSQC, HMBC, and ROESY sequences. Both compounds 1 and 2 were tested against the A2780 human ovarian cancer cell line and the U937 human histiocytic lymphoma cell line assays, and showed significant antiproliferative activity with IC50 values of 0.12 and 0.07 μM against the A2780 human ovarian cancer cell line, and 0.15 and 0.08 μM against the U937 human histiocytic lymphoma cell line, respectively. 相似文献
2.
Liva Harinantenaina Peggy J. Brodie Jean Maharavo Gisele Bakary Karen TenDyke Yongchun Shen David G.I. Kingston 《Bioorganic & medicinal chemistry》2013,21(11):2912-2917
Dereplication of the antiproliferative ethyl acetate fraction of the Madagascan sponge Carteriospongia sp. led to the detection and isolation of the two known homoscalarane-type sesterterpenes 1 and 2. Investigation of a similar sponge containing closely related compounds afforded the four new antiproliferative homoscalarane sesterterpenes (3 and 5?7). The structures of all isolated compounds were elucidated by spectroscopic methods, including UV, IR and 1D and 2D NMR. Compounds 1, 3 and 5 displayed submicromolar antiproliferative activity against the A2780 ovarian cell line with IC50 values of 0.65, 0.26 and 0.28 μM, respectively, while compounds 6 and 7 showed moderate activity (4.5 and 8.7 μM, respectively). Compounds 3 and 5 also displayed anti-proliferative activity against the H522-T1 non-small cell lung and A2058 human melanoma cancer cell lines. 相似文献
3.
Yanpeng Hou Shugeng Cao Peggy J. Brodie James S. Miller Chris Birkinshaw Mamisoa N. Andrianjafy Rabodo Andriantsiferana Vincent E. Rasamison Karen TenDyke Yongchun Shen Edward M. Suh David G.I. Kingston 《Phytochemistry》2010,71(5-6):669-674
Fractionation of an ethanol extract of a Madagascar collection of the leaves and fruit of Cassipourea lanceolata Tul. led to the isolation of three euphane triterpenoids 1–3. The 1H and 13C NMR spectra of all compounds were fully assigned using a combination of 2D NMR experiments, including COSY, TOCSY, HSQC (HMQC), HMBC and ROESY sequences. The three compounds showed weak antiproliferative activities against the A2780 human ovarian cancer cell line, with IC50 values of 25, 25 and 32 μM, respectively. 相似文献
4.
Yixi Liu Liva Harinantenaina Peggy J. Brodie Jessica D. Bowman Maria B. Cassera Carla Slebodnick Martin W. Callmander Richard Randrianaivo Etienne Rakotobe Vincent E. Rasamison Wendy Applequist Chris Birkinshaw Gwilym P. Lewis David G.I. Kingston 《Bioorganic & medicinal chemistry》2013,21(24):7591-7594
Bioassay-directed fractionation of the leaf and root extracts of the antiproliferative Madagascar plant Stuhlmannia moavi afforded 6-acetyl-5,8-dihydroxy-2-methoxy-7-methyl-1,4-naphthoquinone (stuhlmoavin, 1) as the most active compound, with an IC50 value of 8.1 μM against the A2780 human ovarian cancer cell line, as well as the known homoisoflavonoid bonducellin (2) and the stilbenoids 3,4,5′-trihydroxy-3′-methoxy-trans-stilbene (3), piceatannol (4), resveratrol (5), rhapontigenin (6), and isorhapontigenin (7). The structure elucidation of all compounds was based on NMR and mass spectroscopic data, and the structure of 1 was confirmed by a single crystal X-ray analysis. Compounds 2?5 showed weak A2780 activities, with IC50 values of 10.6, 54.0, 41.0, and 74.0 μM, respectively. Compounds 1?3 also showed weak antimalarial activity against Plasmodium falciparum with IC50 values of 23, 26, and 27 μM, respectively. 相似文献
5.
《Bioorganic & medicinal chemistry》2016,24(21):5418-5422
Antimalarial bioassay-guided fractionation of the swamp lily Crinum erubescens led to the isolation of four compounds with potent antiplasmodial activity. Compounds 1 and 2 were determined from their spectroscopic data to be the known pesticidal compound cripowellin A and the known pesticidal and antiproliferative compound cripowellin B. 1D and 2D-NMR techniques were used to determine the identities of 3 and 4 as the new compounds cripowellin C and D. A fifth compound was identified as the known alkaloid hippadine, which was inactive against Plasmodium falciparum. The antiplasmodial IC50 values of compounds 1–4 were determined to be 30 ± 2, 180 ± 20, 26 ± 2, and 260 ± 20 nM, respectively, and their antiproliferative IC50 values against the A2780 human ovarian cancer cell line were 11.1 ± 0.4, 16.4 ± 0.1, 25 ± 2, and 28 ± 1 nM. 相似文献
6.
《Phytochemistry》2012
The cell extract of a cultured terrestrial Nostoc sp. (UIC 10062), obtained from a sample collected at Grand Mere State Park in Michigan, displayed antiproliferative activity against the HT-29 human colon cancer cell line. Bioactivity-guided fractionation of the cell extract, combined with LC–MS analysis, led to the isolation of two cyclophanes, named merocyclophanes A and B (1 and 2). Their structures were determined by various spectroscopic techniques including HRESIMS, and 1D and 2D NMR analyses. The stereoconfiguration was assigned on the basis of X-ray crystallographic and CD analyses. The structures of merocyclophanes A and B (1 and 2) established a hitherto unknown [7.7]paracyclophane skeleton in nature, as characterized by α-branched methyls at C-1/14. Merocyclophanes A and B (1 and 2) displayed antiproliferative activity against the HT-29 human colon cancer cell line with IC50 values of 3.3 and 1.7 μM, respectively. 相似文献
7.
Pan E Harinantenaina L Brodie PJ Callmander M Rakotonandrasana S Rakotobe E Rasamison VE Tendyke K Shen Y Suh EM Kingston DG 《Bioorganic & medicinal chemistry》2011,19(1):422-428
Investigation of the endemic Madagascar plant Leptadenia madagascariensis Decne. (Apocynaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the four new cardenolides 1-4. The structure elucidations of these compounds were based on analyzes of their 1D and 2D NMR spectra and mass spectrometric data. The cardenolides were strongly antiproliferative to the A2780 ovarian cancer cell line, with IC50 values of 0.18, 0.21, 0.17, and 0.29 ??M line, and to the H460 human lung cancer cell line, with IC50 values of 0.16, 0.68, 0.37, and 0.48 ??M, respectively. 相似文献
8.
Ki Hyun Kim Hyung Jun Noh Sang Un Choi Ki Moon Park Soon-Ja Seok Kang Ro Lee 《Bioorganic & medicinal chemistry letters》2010,20(18):5385-5388
Subvellerolactones B (1), D (2), and E (3), structurally unusual lactarane sesquiterpenoids, were isolated from the fruiting bodies of Lactarius subvellereus together with four known lactarane sesquiterpenes (4–7). The chemical structures and stereochemistries of compounds 1–3 were determined on the basis of spectroscopic analyses, including 1D and 2D NMR experiments and a convenient Mosher ester procedure. Subvellerolactone B (1) exhibited cytotoxicity against the A549, SK-MEL-2, and HCT-15 cell lines with IC50 values of 26.5, 18.3, and 14.2 μM, respectively, and subvellerolactones D (2) and E (3) showed cytotoxicity against the A549 and HCT-15 cell lines (IC50 (2): 25.1 and 17.8 μM, and IC50 (3): 19.6 and 28.7 μM, respectively). 相似文献
9.
Two new lignans, gymnothelignans V (1) and W (2), were isolated from a methanol extraction of Gymnotheca chinensis Decne. Their structures were established on the basis of extensive 1D and 2D NMR spectroscopy. Compound 1 exhibited moderate cytotoxicity against the HCT116, HCT15, A549, MCF-7 and HepG2 cancer cell lines with IC50 values of 45.1 μM, 26.9 μM, 49.6 μM, 30.0 μM and 49.7 μM, respectively. Compound 2 exhibited weak cytotoxicity against the A549 cancer cell line with an IC50 value of 41.3 μM. 相似文献
10.
《Bioorganic & medicinal chemistry》2014,22(5):1690-1699
Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl)allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI50) of 42 μM in MCF-7 (breast) cells and 24 μM in A2780 (ovarian) cells and >50 μM in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI50 values of <5 μM were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. 相似文献
11.
Jung Wha Kim Hong Pyo Kim Sang Hyun Sung 《Bioorganic & medicinal chemistry letters》2017,27(14):3144-3147
Two new pterosin glycosides, (2S,3S)-pterosin C 3-O-β-d-(4′-(E)-caffeoyl)-glucopyranoside (1) and (2S,3S)-pterosin C 3-O-β-d-(6′-(E)-p-coumaroyl)-glucopyranoside (2), were isolated from Pteris multifida (Pteridaceae) roots along with ten known pterosin compounds (3–12). The chemical structures of the isolated compounds were elucidated by extensive analysis of the 1D, 2D NMR, HRESIMS, and CD spectroscopic data. The cytotoxicities of 1–12 against HCT116 human colorectal cancer cell line were evaluated. Among the isolates, compound 1 showed moderate antiproliferative activity in HCT116 cells with an IC50 value of 8.0 ± 1.7 μM. Additionally, 1 induced the upregulation of the caspase-9 and procaspase-9 levels in Western blots and increased the annexin V/propidium iodide (PI)-positive cell population in flow cytometry. 相似文献
12.
Sanjay Saha Ch. Venkata Ramana Reddy T. Chiranjeevi Uma Addepally T.S. Chinta Rao Balaram Patro 《Bioorganic & medicinal chemistry letters》2013,23(4):1013-1016
We have developed the first total syntheses of marine natural products ma’edamines A (18) and B (20). Structurally, they contain a pyrazine-2-(1H)-one core and were screened for antiproliferative activity on several cancer cell lines. Out of the six cell lines tested, ma’edamines A and B showed significant cytotoxicity against human colon cancer line COLO 205 (IC50 7.9 and 10.3 μM, respectively), breast cancer cell line MCF-7 (IC50: 6.9 and 10.5 μM, respectively) and human lung adenocarcinoma cell line A549 (IC50: 12.2 and 15.4 μM, respectively). The apoptotic effect of ma’edamines was confirmed by comet assay. Hence ma’edamines are likely to be useful as leads for development of a new class of anti-cancer agents. 相似文献
13.
Chemical investigation of the mangrove fungal endophytes, Phomopsis spp. xy21 and xy22, afforded four new cytochalasins, named phomopsichalasins D-G, along with six known analogues. The structures of these cytochalasins were elucidated on the basis of HRESIMS and extensive NMR spectroscopic data. Phomopsichalasins D (1) and E (2) represent the first two 10-phenyl[11]-cytochalasans containing a 12-carboxyl function. All of the isolates were evaluated for their cytotoxicities against eight human cancer cell lines by the MTT method. Phomopsichalasin G (4) exhibited inhibitory activities against HCT-8, HCT-8/T, A549, MDA-MB-231, and A2780 cancer cell lines with IC50 values of 7.5, 8.6, 6.4, 3.4, and 7.1 μM, respectively. 相似文献
14.
Yanpeng Hou Shugeng Cao Peggy J. Brodie Martin W. Callmander Fidisoa Ratovoson Etienne A. Rakotobe Vincent E. Rasamison Michel Ratsimbason John N. Alumasa Paul D. Roepe David G.I. Kingston 《Bioorganic & medicinal chemistry》2009,17(7):2871-2876
Bioassay-guided fractionation of an ethanol extract of a Madagascar collection of the bark of Scutia myrtina led to the isolation of three new anthrone–anthraquinones, scutianthraquinones A, B and C (1–3), one new bisanthrone–anthraquinone, scutianthraquinone D (4), and the known anthraquinone, aloesaponarin I (5). The structures of all compounds were determined using a combination of 1D and 2D NMR experiments, including COSY, TOCSY, HSQC, HMBC, and ROESY sequences, and mass spectrometry. All the isolated compounds were tested against the A2780 human ovarian cancer cell line for antiproliferative activities, and against the chloroquine-resistant Plasmodium falciparum strains Dd2 and FCM29 for antiplasmodial activities. Compounds 1, 2 and 4 showed weak antiproliferative activities against the A2780 ovarian cancer cell line, while compounds 1–4 exhibited moderate antiplasmodial activities against P. falciparum Dd2 and compounds 1, 2, and 4 exhibited moderate antiplasmodial activities against P. falciparum FCM29. 相似文献
15.
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
16.
Three new ent-kauranoid glycosides, fructusnoids A-C (1-3) were isolated from the fruits of Xanthium strumarium. Their structures were elucidated by extensive spectroscopic methods, including NMR, MS, and HRESIMS data. Compounds 1-2 are novel examples of rearranged ent-kauranoid diterpenes with missing C-18/19 carbons. All the compounds were evaluated for their antiproliferative activity in vitro against three human cancer cell lines, and compound 3 showed selective cytotoxic activity against the AGS cancer cell line with an IC50 value of 7.6 μM. 相似文献
17.
《Bioorganic & medicinal chemistry letters》2014,24(2):601-603
Based on previous SAR studies on N-benzylindole and barbituric acid hybrid molecules, we have synthesized a series of aromatic substituted 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione analogs (3a–i) and evaluated them for their in vitro growth inhibition and cytotoxicity against a panel of 60 human tumor cell lines. Compounds 3c, 3d, 3f and 3g were identified as highly potent anti-proliferative compounds against ovarian, renal and breast cancer cell lines with GI50 values in low the nanomolar range. The 4-methoxy-N-benzyl analog (3d) was the most active compound with GI50 values of 20 nM and 40 nM against OVCAR-5 ovarian cancer cells and MDA-MB-468 breast cancer cells, respectively. Two other analogs, 3c (the 4-methyl-N-benzyl analog) and 3g (the 4-fluoro-N-benzyl analog) exhibited equimolar potency against MDA-MB-468 cells GI50 = 30 nM). Analog 3f (the 4-chloro-N-benzyl analog) exhibited a GI50 value of 40 nM against renal cancer cell line A498. These results suggest that aromatic substituted N-benzylindole dimethylbarbituric acid hybrids may have potential for development as clinical candidates to treat a variety of solid tumors. 相似文献
18.
Phytochemical investigation of the EtOAc and MeOH extracts from flowers of Getonia floribunda Roxb., a Thai herbal medicine, resulted in the isolation of two new flavonols, 4′-hydroxy-6,7,8,3′-tetramethoxyflavonol (1) and 4′-hydroxy-6,7,8-trimethoxyflavonol (2), along with a known pachypodol (3). Their structures were elucidated by spectroscopic methods including UV, IR, 1D and 2D NMR techniques and MS analysis. Compound 1 showed cytotoxicity against the oral cavity cancer (KB) cell line with an IC50 value of 8.99 ± 2.00 μg/ml. 相似文献
19.
Quan-Xin Wang Jian-Ling Yang Qiu-Yue Qi Li Bao Xiao-Li Yang Miao-Miao Liu Pei Huang Li-Xin Zhang Ji-Long Chen Lei Cai Hong-Wei Liu 《Bioorganic & medicinal chemistry letters》2013,23(12):3547-3550
A new ophiobolin derivative, 3-anhydro-6-hydroxy-ophiobolin A (1), as well as two known ophiobolin derivatives 3-anhydro-ophiobolin A (2) and 3-anhydro-6-epi-ophiobolin A (3) were isolated from the PDB culture of a phytopathogenic fungus Bipolaris oryzae. The structure of 1 was elucidated through 2D NMR and other spectroscopic techniques. Compound 1 exhibited strong antimicrobial activity against Bacille Calmette–Guerin, Bacillus subtilis, Staphylococcus aureus, and methicillin-resistant Staphylococcus aureus with MIC value of 12.5 μg/mL, and potent antiproliferative activity against cell lines HepG2 and K562 with IC50 of 6.49 μM and 4.06 μM, respectively. Further studies on the cytotoxicity of compound 1 against K562 cells demonstrated that it induced apoptosis, observed by flow cytometric method. Preliminary structure–activity relationships of these ophiobolins and the mechanism of apoptosis induced by 1 were analyzed. 相似文献
20.
Ke Zan Xiao-Qing Chen Xing-Yun Chai Qing Wu Qiang Fu Si-Xiang Zhou Peng-Fei Tu 《Phytochemistry letters》2012,5(2):313-315
Two new eudesmane sesquiterpenoids artanoate (1) and eudesmanomolide (2) were isolated from the aerial parts of Artemisia anomala S. Moore. Their structures were elucidated as methyl (4R, 5S, 6S, 7S, 10R)-1-oxo-4, 6-dihydroxy-eudesma-2, 11 (13)-dien-12-oate (1) and (1R, 5R, 6R, 10R)-3, 13-diacetoxy-1-hydroxy-3, 7(11)-diene-12, 6-olide (2) on the basis of extensive spectroscopic analyses. Compound 1 showed cytotoxicity against HCT-8 cell lines with IC50 value of 9.13 μM, and compound 2 exhibited inhibitory activities against HCT-8 and A549 cell lines with IC50 values of 3.76 and 5.49 μM, respectively. 相似文献