Sesquiterpenes from the Fungus Antrodiella albocinnamomea with Cytotoxicity and Antibacterial Activity
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Abstract:
Eight new sesquiterpenes, namely, albocinnamins A−H (1−8), along with two known ones (9 and 10), have been isolated from the fungus Antrodiella albocinnamomea. Compound 1 possesses a new backbone that might be derived from cadinane-type sesquiterpene. Structures of the new compounds were elucidated by detailed spectroscopic data analysis, single-crystal X-ray diffraction, and ECD calculations. Compounds 1a and 1b showed cytotoxicity against SW480 and MCF-7 cells, with IC50 values ranging from 19.3 to 33.3 μM, while compound 2 displayed cytotoxicity against the HL-60 cell with an IC50 value of 12.3 μM. In addition, compounds 5 and 6 exhibited antibacterial activity against Staphylococcus aureus with MIC values of 64 and 64 µg/mL, respectively.Keywords:
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Chemical investigation of the sponge Dysidea sp. afforded three new sesquiterpene phenols (1–3) and one new sesquiterpene aminoquinone (4), together with four known sesquiterpene derivatives (5–8). The structures of all compounds were unambiguously elucidated by extensive spectroscopic analysis, as well as by comparison with the literature. The absolute configurations of compounds 1–4 were determined by electron capture detector (ECD) calculations and circular dichroism (CD) spectrum analysis. Their antibacterial activity against Escherichia coli (25922), Bacillus subtilis (6633), and Staphylococcus aureus (25923) were evaluated. Compounds 1 and 3 showed weak antibacterial activity against the above three strains, whereas compounds 4–8 showed potent antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 3.125 to 12.5 µg/mL.
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Two new sesquiterpene lactones, spicatolide C (1) and spicatocadinanolide A (2), have been isolated along with the known piptocarphol isomers (3, 4) and one eudismane type sesquiterpene (5) from the EtOAc extract of the aerial parts of Pseudoelephantopus spicatus. The structures and the relative stereochemistries of the new metabolites were determined by spectroscopic methods.
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Objective:Assess cytotoxicity of medical device with silver nanoparticles and assay the reason of the cytotoxicity.Method:The nine kinds of silver nanoparticle samples in three types were tested by MTT cytotoxicity method.Result:The test showed that the cytotoxic ity in 9 final samples all were grade 3 to 4;the gels and dressings which are semi-finished products without silver nanoparticles,were grade 1 of cytotoxicity;patches were grade 4 of cytotoxicity;patches without adhesive were grade 1 of cytotoxicity.Conclusion:Silver nanoparticle medical devices in the present test showed moderate or severe cytotoxicity.Gels or dressings only which without silver nanoparticle showed slightly cytotoxicity.Patches only which without silver nanoparticle showed severe cytotoxicity,and adhesive is the main reason of the cytotoxicity.Whether the severe cytotoxicity will induce persist cell damage,and the detail mechanisms of silver nanoparticle or adhesive-induced cytotoxicity need further investigation.
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ABSTRACT To investigate the profiles of sesquiterpene hydrocarbons in grape berries at different developmental stages several cultivars of Vitis vinifera (Gewürztraminer, Riesling, Yellow Muscat, Shiraz, Lemberger, Cabernet Sauvignon) were analysed during ripening. Therefore, HS‐SPME‐GC‐MS measurements were performed with intact grape berries. The measurements demonstrated that grapes emit numerous sesquiterpene hydrocarbons and that the sesquiterpene profile exhibits a characteristic profile, depending on the variety and the developmental stage. In particular, bicylic sesquiterpenes with a cadinane backbone increased during ripening, while acyclic sesquiterpenes such as ( E , E )‐ α ‐farnesene decreased, except for Gewürztraminer which shows increasing amounts of acyclic sesquiterpenes towards harvest. Furthermore, the profiles of the emitted sesquiterpenes differed significantly. In particular, Gewürztraminer possessed remarkably high amounts of ( E , E )‐ α ‐farnesene, (3 E ,6 Z )‐ α ‐farnesene and ( E , E )‐methylfarnesoate, while the sesquiterpene profiles of Riesling, Lemberger, Shiraz and Yellow Muscat were dominated by bi‐ and polycyclic sesquiterpenes. Cabernet Sauvignon showed only minor profile changes during ripening and its comparatively low sesquiterpene hydrocarbon amounts were dominated by ( E )‐ β ‐caryophyllene, α ‐humulene and an unidentified sesquiterpene. Copyright © 2012 John Wiley & Sons, Ltd.
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Five muurolane (1–5), one nor-seco-muurolane (6) and one nor-muurolane (7) sesquiterpene natural products recently reported from Cupressus bakeri have been obtained by chemical synthesis together with the unnatural 7-epimeric amorphane analogues of four of these sesquiterpenes (15, 16, 18 and 19). The conversion of sesquiterpene allylic tertiary alcohols 1, 2, 15 and 16 into regioisomeric sesquiterpene dienes 3–5 and 17–20 was investigated in vitro by NMR and the mechanism for such dehydrations and their relevance to the origins of sesquiterpene dienes which have been reported as natural products (such as 3–5) is discussed.
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Eight aza-chalcones L1-8 and eight new platinum(IV) complexes C1-8 with aza-chalcones were synthesized. The complexes have been characterized by elemental anaylsis, IR spectra, electronic spectrum and 1H NMR. The cytotoxicity was tested byMTT assays and compared with the cytotoxicity of cisplatinum. The results indicate that the complexes C1-3 and C5-8 have cytotoxicity against tested A-549 cell line; moreover, the cytotoxicity of complexes C6 approached cisplatinum. The complexes C3, C4 and C6 have cytotoxicity against tested Hela cell line, but the cytotoxicity of these complexes is lower than cisplatinum.Most of the coorespounding ligands have no cytotoxicity against tested two cell lines, and the cytotoxicity of all ligands is lower than complexes.The results suggest that the cytotoxicity of all complexes againstA-549 cell line is better than against Hela cell line.
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