scholarly journals Dactylospenes A–E, Sesterterpenes from the Marine Sponge Dactylospongia elegans

Marine Drugs ◽  
2020 ◽  
Vol 18 (10) ◽  
pp. 491
Author(s):  
Hao-Bing Yu ◽  
Bin-Bin Gu ◽  
Arihiro Iwasaki ◽  
Wen-Li Jiang ◽  
Andrew Ecker ◽  
...  

Chemical investigation on a marine sponge, Dactylospongia elegans, yielded five new γ-oxygenated butenolide sesterterpene derivatives, dactylospenes A–E (1–5), as well as two known biosynthetically related compounds, luffariellolide (6) and furospinosulin B (7). The structures of these compounds were elucidated on the basis of their spectroscopic data, experimental and calculated electronic circular dichroism (ECD) analysis, as well as comparison of the NMR data with those of known analogs. These metabolites are the first γ-oxygenated butenolide sesterterpenes to be reported from this genus. These compounds were evaluated in antimicrobial, anti-inflammatory, and cytotoxic assays. Only compounds 1, 3, and 6 exhibited moderate cytotoxicity against DU145, SW1990, Huh7, and PANC-1 cancer cell lines with IC50 values in the range of 2.11–13.35 μM. Furthermore, compound 2, without cytotoxicity, exhibited significant inhibitory effects (inhibitory rate 77.5%) on nitric oxide production induced by lipopolysaccharide at 10 μM.

Planta Medica ◽  
2018 ◽  
Vol 85 (02) ◽  
pp. 112-117 ◽  
Author(s):  
Meng-Yuan Jiang ◽  
Ming Luo ◽  
Kai Tian ◽  
Yan-Hong Li ◽  
Jing-Xian Sun ◽  
...  

AbstractFour new coumestans dolichosins A – D (1–4) were isolated from the roots of Dolichos trilobus, together with four known compounds: isosojagol (5), phaseol (6), psoralidin (7), and 4″,5″-dehydroisopsoralidin (8). Their structures were elucidated on the basis of spectroscopic data interpretation, mass spectrometric analyses, and the comparison with literature data of related compounds. The anti-inflammatory activity of these compounds (1–8) was evaluated through the inhibition of nitric oxide production in lipopolysaccharide-activated murine macrophage RAW 264.7 cells, in which compounds 1 and 6 displayed moderate inhibitory activity and no cytotoxic effects. In a α-glucosidase inhibitory assay, compounds 1 and 5–8 exhibited appreciable inhibition on α-glucosidase. Especially compounds 1, 7, and 8 showed IC50 values lower than 20.0 µM.


2007 ◽  
Vol 62 (11-12) ◽  
pp. 786-792 ◽  
Author(s):  
Lip Jabit ◽  
Rozida Khalid ◽  
Faridah Abas ◽  
Khozirah Shaari ◽  
Lim Siang Hui ◽  
...  

Two new xanthones, characterized as 4-(1,1-dimethylprop-2-enyl)-1,3,5,8-tetrahydroxyxanthone (1) and penangianaxanthone (2), with three known xanthones, cudratricusxanthone H (3), macluraxanthone C (4) and gerontoxanthone C (5), as well as friedelin and stigmasterol were isolated from the leaves of Garcinia penangiana. Their structures were elucidated by analysis of spectroscopic data and comparison of the NMR data with the literature ones. Significant cytotoxicity against DU-145, MCF-7 and NCI-H460 cancer cell lines was demonstrated by compounds 1D5, with IC50 values ranging from 3.5 to 72.8 μm.


2015 ◽  
Vol 40 (3) ◽  
Author(s):  
Mükerrem Betül Yerer ◽  
Eren Demirpolat ◽  
Ahmet Cumaoğlu ◽  
Canan Torçuk ◽  
Nefise Nalan İmamoğlu ◽  
...  

AbstractObjective: Quinones are highly reactive compounds undergoing either one- or two-electron reductions. Enzymatic one-electron reduction generates unstable semiquinone radicals which readily undergo redox cycling over NQO1 and NQO2 enzymes, in the presence of molecular oxygen, leading to the production of highly reactive oxygen species (ROS). NQO1 is responsible form detoxification where NQO2 inhibitors are found to show potent anticancerogenic effects. The aim of this study is to investigate some natural inhibitors of the NQO2 enzyme and to identify their action mechanisms over this enzyme on different cancer cell lines.Methods: First of all the NQO2 inihibitry effects of flavonoids were investigated over enzyme kinetix and Ki values were calculated. Then the cytotoxic effects of flavonoids on different cancer cell lines such as Jurkat Clone E-6, MCF7 and HepG2 cancer cell lines were investigated via MTT test and their effects on NQO2 protein expressions via western blotting.Results: Ki values for NQO2 inhibitory effects of the studied flavonoids are respectively, Apigenin (0.25 nM) <Kaempferol (0.55 nM) <Quercetin (1.06 nM) <Luteolin (1.54 nM). The IC50 values for flavonoids in three different cell lines were as follows: for Apigenin; 140 μM, 50 μM and 50 μM, for Kaempferol; 40 μM, 100 μM and 400 μM, for Quercetin; 10 μM, 60 μM and 50 μM, and for Luteolin; 50 μM, 60 μM and 75 μM in Jurkat Clone E-6, MCF7 and HepG2 cell lines, respectively. According to the western blotting results in Jurkat cell line, Apigenin; in MCF7, Kaempferol; significantly (p<0.05) reduced the NQO2 expression whereas in HepG2 cell lines any of them did not reveal any inhibitory effects.Conclusion: As a result, the tested flavonoids were all inhibitors of NQO2 enzyme in nM levels and in Jurkat and MCF7 cell lines the cytotoxic effects of Apigenin and Kaempferol have been associated with NQO2 inhibition.


2002 ◽  
Vol 57 (7-8) ◽  
pp. 732-738 ◽  
Author(s):  
Anake Kijjoa ◽  
Rawiwan Watanadilok ◽  
Pichai Sonchaeng ◽  
Pichan Sawangwong ◽  
Madalena Pedro ◽  
...  

Reexamination of the marine sponge Suberea aff. praetensa, (Row) from the Gulf of Thailand furnished in addition to bromotyrosine derivatives found previously 5-bromo- and 5- chlorocavernicolin, cavernicolins 1 and 2, two other brominated tyrosine metabolites, a known bisoxazolidone and a new unusual rearranged tyrosine metabolite subereatensin. Several of the metabolites exhibited significant inhibitory effects against five human cancer cell lines.


2021 ◽  
Vol 7 (6) ◽  
pp. 408
Author(s):  
Virayu Suthiphasilp ◽  
Achara Raksat ◽  
Tharakorn Maneerat ◽  
Sarinya Hadsadee ◽  
Siriporn Jungsuttiwong ◽  
...  

Chemical investigation of the mycelia of the pathogenic fungus Curvularia sp. which was isolated from a leaf of Dactyloctenium aegyptium (crowfoot grass), resulted in the isolation of a new compound, curvulariahawadride (5), along with five known compounds (1–4, and 6). Their structures were determined on the basis of spectroscopic data, including 1D and 2D NMR and HRESIMS. The absolute configuration of 5 was established from experimental and calculated electronic circular dichroism (ECD). Compounds 1, 3, and 5 showed nitric oxide (NO) production inhibitory activity with IC50 values of 53.7, 32.8, and 12.8 µM, respectively. Compounds 2 and 4 showed significant cytotoxicity against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells with an IC50 ranging value of 11.73 to 17.59 µM.


2020 ◽  
Vol 13 (03) ◽  
pp. 1047-1062
Author(s):  
Dahlan-Daud C. K ◽  
Zain Z. N ◽  
Tham C. L. ◽  
Yong Y. K. ◽  
Hakim M. N

The 6-Mercaptopurine (6-MP) is a purine sulphur derivative used in the treatment of children with leukaemia as an antitumor medication. Nonetheless, the anti-proliferation and anti-rheumatoid arthritic activities of the drug have not been previously described. Therefore, the current study objective was to determine the cytotoxicity effects of 6-MP, 6-mercaptopurine riboside (6-MPR), 6-thioguanine (6-TG) and 6-thioxanthine (6-TX) on murine macrophages (RAW 264.7) and rabbit synoviocytes (HIG-82) cell lines. An inflammatory stage of RAW 264.7 and HIG-82 cell lines stimulated with Escherichia coli lipopolysaccharide (LPS) and phorbol-12-myristate acetate (PMA), respectively were treated with the drugs at a serials concentration 3.125 – 100 µM. Subsequently, the MTT assay was used to determine the viability of cells. The inhibitory effects were measured based on nitric accumulation in the conditioned media. The results showed that all drugs tested did not show any cytotoxic effect on both cell lines at low and medium concentrations, which the HIG-82 cell viability was more than 80%. However, the drugs display anti-proliferation property on RAW 264.7 cells compared to control. Reduction on cell proliferation was found on all tested drugs. Among its, the diclofenac significantly reduced the proliferation on HIG-82 cell compared to other drug compounds. Inhibitory effects of compound on nitric oxide production PMA-stimulated HIG-82 had only a small inductive effect, but excellent inhibition was observed on RAW 264.7 cell. Meanwhile, 100 μM 6-thioguanine and diclofenac had cytotoxic effect to RAW 264.7 and HIG-82 cell respectively. All thiopurines enhanced the proliferation of HIG-82 and RAW 264.7 cells with no cytotoxic effects. This finding opens new avenues for treating RA and the anti-rheumatic activities during synovial inflammation stage of RA. The inhibitory effects of 6-MP and 6-MPR to inflammatory cells marker such as synovial fibroblast and macrophages by proliferating healthy synoviocytes more potenly than 6-TG and 6-TX. The current study has demonstrated the potential use of 6-MP and its associated thio compounds in the in-vitro approach of HIG-82 cell culture in curing rheumatoid arthritis disease.


Marine Drugs ◽  
2021 ◽  
Vol 20 (1) ◽  
pp. 5
Author(s):  
Xiaoya Qin ◽  
Jiguo Huang ◽  
Dexiong Zhou ◽  
Wenxiu Zhang ◽  
Yanjun Zhang ◽  
...  

Four undescribed compounds, guhypoxylonols A (1), B (2), C (3), and D (4), were isolated from the mangrove endophytic fungus Aspergillus sp. GXNU-Y45, together with seven previously reported metabolites. The structures of 1–4 were elucidated based on analysis of HRESIMS and NMR spectroscopic data. The absolute configurations of the stereogenic carbons in 1–3 were established through a combination of spectroscopic data and electronic circular dichroism (ECD). Compounds 1–11 were evaluated for their anti-inflammatory activity. Compounds 1, 3, 4, and 6 showed an inhibitory activity against the production of nitric oxide (NO), with the IC50 values of 14.42 ± 0.11, 18.03 ± 0.14, 16.66 ± 0.21, and 21.05 ± 0.13 μM, respectively.


2013 ◽  
Vol 8 (5) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Yuh-Ming Fuh ◽  
Mei-Chin Lu ◽  
Chia-Hung Lee ◽  
Jui-Hsin Su

A new scalarane sesterterpenoid, hippospongide C (1), along with four previously reported known scalarane–type sesterterpenes (2–5), were isolated from a sponge Hippospongia sp. The structure of 1 was elucidated on the basis of its spectroscopic data and comparison of its NMR data with those of known analogues. The cytotoxicity of 1–5 against DLD-1, HCT-116, T-47D and K562 cell lines was evaluated. The results showed that compound 4 exhibited potent activity against DLD-1, HCT-116 and T-47D cell lines with IC50 values of 1.3–2.0 μg/mL. Furthermore, metabolites 1–5 were also found to exhibit significant cytotoxicity towards the K562 cell line with IC50 values of 0.01–2.9 μg/mL.


2019 ◽  
Vol 16 (6) ◽  
pp. 474-477 ◽  
Author(s):  
Pham Van Khang ◽  
Nguyen Thi Hien Lan ◽  
Le Quang Truong ◽  
Mai Thi Minh Chau ◽  
Mai Xuan Truong ◽  
...  

In this report, two new steroidal glycosides were isolated and determined from n-butanol fraction of A.asphodeloides. The structures were confirmed in comparison with the spectral data of known compounds by using different spectroscopic analysis approaches including 1D & 2D-NMR techniques and HRMS. The anti-proliferation screening against cancer cell lines A549 and HeLa indicated that compound 1 exhibited good inhibitory activities with IC50 values of 0.79 and 0.55 &#181;g/mL, respectively.


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