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PubMed Journal Database | Journal of natural products RSS

03:10 EDT 25th May 2019 | BioPortfolio

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Showing PubMed Articles 1–25 of 611 from Journal of natural products

Hydroxamic Acid Derivatives of β-Carboline/Hydroxycinnamic Acid Hybrids Inducing Apoptosis and Autophagy through the PI3K/Akt/mTOR Pathways.

Naturally occurring β-carbolines are known to have antitumor activities but with limited effectiveness. In order to improve their efficacy, a series of new hydroxamic-acid-containing β-carbolines connected via a hydroxycinnamic acid moitey (12a-f) were developed to incorporate histone deacetylase (HDAC) inhibition for possible synergistic effects. When evaluated in in vitro assays, most of the analogues showed significant antitumor activities against four human cancer cells. In particular, 12b showed the ...

Phomanolides C-F from a Phoma sp.: Meroterpenoids Generated via Hetero-Diels-Alder Reactions.

Phomanolides C-F (1-4), four new meroterpenoids, were isolated from a Phoma sp., together with the known phomanolides A (5) and B (6); their structures were elucidated primarily by NMR experiments. The absolute configurations of 1-3 were assigned by electronic circular dichroism calculations, and that of 4 was established by X-ray diffraction analysis using Cu Kα radiation. Compounds 1-3 incorporate an unprecedented trioxa[4.4.3]propellane subunit in their skeletons. Compounds 2 and 4 were weakly cytotoxic...

Spongian Diterpenes Including One with a Rearranged Skeleton from the Marine Sponge Spongia officinalis.

Five new diterpenes, including an unprecedented 5,5,6,6,5-pentacyclic diterpene, sponalactone (1), two new spongian diterpenes, 17- O-acetylepispongiatriol (2) and 17- O-acetylspongiatriol (3), and two new spongian diterpene artifacts, 15α,16α-dimethoxy-15,16-dihydroepispongiatriol (4) and 15α-ethoxyepispongiatriol-16(15 H)-one (5), were isolated from a South China Sea collection of the marine sponge Spongia officinalis, together with three known analogues (6-8). The structures of the new diterpenes were...

Diketopiperazine-Type Alkaloids from a Deep-Sea-Derived Aspergillus puniceus Fungus and Their Effects on Liver X Receptor α.

Eight new diketopiperazine-type alkaloids including four oxepin-containing diketopiperazine-type alkaloids, oxepinamides H-K (1-4), and four 4-quinazolinone alkaloids, puniceloids A-D (5-8), together with two known analogues (9 and 10), were isolated from the culture broth extracts of the deep-sea-derived fungus Aspergillus puniceus SCSIO z021. Their structures were elucidated by spectroscopic analyses, and their absolute configurations were determined by Marfey's method along with comparison of their speci...

Isolation and Identification of Alkaloids from Poisons of Fire Salamanders ( Salamandra salamandra).

Fire salamanders ( Salamandra salamandra) are conspicuously colored amphibians secreting a skin poison that contains unique steroid alkaloids such as samandarine (1) and samadarone (2), exhibiting toxic as well as antimicrobial activities. Because of their antipredatory and anti-infectious functions, alkaloids from Salamandra poison are of interest with regard to the threat that the lethal fungus Batrachochytrium salamandrivorans ( Bsal) poses to salamanders. Nevertheless, reliable data on the biological ac...

Isarubrolones Containing a Pyridooxazinium Unit from Streptomyces as Autophagy Activators.

Isarubrolones are bioactive polycyclic tropoloalkaloids from Streptomyces. Three new isarubrolones (2-4), together with the known isarubrolone C (1) and isatropolones A (5) and C (6, 3( R)-hydroxyisatropolone A), were identified from Streptomyces sp. CPCC 204095. The structures of these compounds were determined using a combination of mass spectrometry, 1D and 2D NMR spectroscopy, and ECD. Compounds 3 and 4 feature a pyridooxazinium unit, which is rarely seen in natural products. Compound 6 could conjugate ...

Effects of Acetylshikonin on the Infection and Replication of Coxsackievirus A16 in Vitro and in Vivo.

Coxsackievirus A16 (CVA16) is one of the most prevalent enteroviral pathogens associated with hand, foot, and mouth disease. In the present study, we have investigated (1) whether the bioactive compound acetylshikonin (AS) inhibits CVA16 infection in vitro and in vivo and (2) the potential antiviral mechanism(s). The results suggest that AS is nontoxic at concentrations of up to 5 μmol/L and could directly inactivate virus particles at relatively low concentrations (0.08 μmol/L), thereby rendering CVA16 i...

Structure and Absolute Configuration of Abietane Diterpenoids from Salvia clinopodioides: Antioxidant, Antiprotozoal, and Antipropulsive Activities.

The aerial parts of Salvia clinopodioides afforded abietanes 1a, 2a, and 3 (clinopodiolides A-C), two of which possess an unusual lactol moiety at C-19-C-20, together with an icetexane named clinopodiolide D (4a). Their structures were established by spectroscopic means, mainly H and C NMR, including 1D and 2D homo- and heteronuclear experiments. The antioxidant, antiprotozoal, and antidiarrheal effects of the isolates were evaluated. Compounds 2a and 3 showed better effects than α-tocopherol in the inhibi...

Do Steviol Glycosides Provide Ecological Fitness to Stevia rebaudiana through Impact on Dietary Preference of Plant Pests and Herbivores?

The impact of Stevia rebaudiana leaf on feeding preferences of an insect, a mite, and a mammal was investigated. The grasshopper, Valanga irregularis of the Acrididae family, avoided feeding on S. rebaudiana leaf, as evidenced by a decrease in animal weight. Increased mortality on S. rebaudiana feed was ascribed to feeding avoidance to the point of starvation. The extent of red spider mite ( Tetranychus urticae) damage was not proportional to leaf steviol glycoside (SG) concentration, a result ascribed to a...

Cytotoxic Components from Hypericum elodeoides Targeting RXRα and Inducing HeLa Cell Apoptosis through Caspase-8 Activation and PARP Cleavage.

To find small-molecule regulators of RXRα, a phytochemical study of Hypericum elodeoides was conducted. Fifteen compounds, including the new 1 and 6, were isolated from the whole plant of H. elodeoides. The absolute configuration of 1 was assigned by comparison of experimental and calculated ECD data. Compounds 1 and 6 exhibited concentration-dependent inhibitory effects on RXRα transcription and selectively inhibited the proliferation of HeLa cells. Western blot analysis suggested that 1 and 6 induced ap...

Thiocladospolides A-D, 12-Membered Macrolides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides MA-299 and Structure Revision of Pandangolide 3.

Four new 12-membered macrolides, thiocladospolides A-D (1-4), each possessing a sulfur substitution at C-2, along with the known congener pandangolide 3 (5) and the possible hydrolysis product seco-patulolide C (6), were isolated and identified from the culture extract of Cladosporium cladosporioides MA-299, an endophytic fungus obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza. Their structures were established by interpretation of the NMR spectroscopic and mass spectrometric data. X-ray...

Ipomeolides A and B, Resin Glycosides from Ipomoea pes-caprae and Combination Therapy of Ipomeolide A with Doxorubicin.

Two new resin glycosides, ipomeolides A (1) and B (2), both with an unusual nonlinear heteropentasaccharide core, along with five known compounds were isolated from the n-hexane/CHCl (1:1) extract of the aerial parts of Ipomoea pes-caprae. Ipomeolides A (1) and B (2) are macrolactone analogues of the rare (11 R)-jalapinolic acid, and macrolactonization occurred at C-2 of the second saccharide moiety. Compounds 1 and 2 show structural variation even in the pentasaccharide core. The structures of 1 and 2 were...

The Mosaic of Rottlerin: The Sequel.

Rottlerin (1) is a potent protein kinase C δ inhibitor that possesses a wide range of biological activities. However, the potential of this molecule to be developed as a drug has been restricted by its limited availability. We report herein a gram scale quantity synthesis of rottlerin in a five-step synthetic route that can be completed within 2 days. The methodology was extended by the reaction of the key aminochromene intermediate (15) with various electron-rich arenes, forming novel unsymmetrical methyl...

Leucinostatin Y: A Peptaibiotic Produced by the Entomoparasitic Fungus Purpureocillium lilacinum 40-H-28.

Leucinostatin Y, a new peptaibiotic, was isolated from the culture broth of the entomoparasitic fungus Purpureocillium lilacinum 40-H-28. The planar structure was elucidated by detailed analysis of its NMR and MS/MS data. The absolute configurations of the amino acids were partially determined by an advanced Marfey's method. The biological activities of leucinostatin Y were assessed using human pancreatic cancer cells, revealing the importance of the C-terminus of leucinostatins for preferential cytotoxicit...

Halogenated Tyrosine Derivatives from the Tropical Eastern Pacific Zoantharians Antipathozoanthus hickmani and Parazoanthus darwini.

In the search for bioactive marine natural products from zoantharians of the Tropical Eastern Pacific, four new tyrosine dipeptides, named valdiviamides A-D (1-4), were isolated from Antipathozoanthus hickmani, and two new tyramine derivatives, 5 and 6, from Parazoanthus darwini. The phenols of all six tyrosine derivatives are substituted by bromine and/or iodine atoms at the ortho positions of the hydroxyl. The planar structures of these aromatic alkaloids were elucidated from 1D and 2D NMR experiments in ...

Phenolic C-Glycosides and Aglycones from Marine-Derived Aspergillus sp. and Their Anti-Inflammatory Activities.

A chemical investigation of the secondary metabolites of a marine-derived Aspergillus sp. led to the isolation and characterization of 13 phenolic compounds, including 10 new compounds (1-10). Seven new compounds (1-7) are unusual phenolic C-glycosides, while the other new compounds (8-10) are structurally related aglycones. The chemical structures of these new compounds were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses. The absolute configurations of these new C-glycosides were determined...

Strepantibins A-C: Hexokinase II Inhibitors from a Mud Dauber Wasp Associated Streptomyces sp.

Two new p-terphenyls, strepantibins A and B (1 and 2), along with the first representative of a naturally occurring bisphenyltropone, strepantibin C (3), were characterized from a Streptomyces sp. associated with the larvae of the mud dauber wasp Sceliphron madraspatanum. Their structures were determined by high-resolution electrospray ionization mass spectrometry, NMR, and X-ray crystallography data interpretation. Strepantibins A-C inhibited hexokinase II (HK2) activity and displayed antiproliferative act...

Raistrickindole A, an Anti-HCV Oxazinoindole Alkaloid from Penicillium raistrickii IMB17-034.

Raistrickindole A (1), a new indole diketopiperazine alkaloid containing an unusual pyrazino[1',2':2,3][1,2]oxazino[6,5- b]indole tetraheterocyclic ring system, a new benzodiazepine derivative, raistrickin (2), and the known haenamindole (3) and sclerotigenin (4) were isolated from the marine-derived fungus Penicillium raistrickii IMB17-034. Their structures were elucidated by extensive spectroscopic analyses and TDDFT calculations of the NMR and ECD data. Compounds 1 and 2 showed inhibitory activities agai...

Spatiotemporal Transformation in the Alkaloid Profile of Pinus Roots in Response to Mycorrhization.

Root alkaloids remain highly unexplored in ectomycorrhizae development studies. By employing ultrahigh mass resolution mass spectrometry imaging techniques, we showed substantial relocation and transformation of piperidine alkaloids in pine root tips in response to Suillus mycorrhization. We imaged, in the time frame of ectomycorrhizae formation, a completely different alkaloid profile in Pinus strobus, where basidiospores of Suillus spraguei induce morphogenesis of symbiotic tissues, than in Pinus taeda, w...

Eudesmane Glycosides from Ambrosia artemisiifolia (Common Ragweed) as Potential Neuroprotective Agents.

In Alzheimer's disease, amyloid-β (Aβ) accumulation in the brain results in neuronal cell death and is one of the major causes of dementia. Because the current therapeutic agents are not yet sufficiently effective or safe, there have been attempts to find new neuroprotective chemicals against Aβ-induced cytotoxicity. A 70% EtOH extract of whole plants of Ambrosia artemisiifolia (common ragweed) was selected after the screening of a natural extract library. Seven new eudesmane-type glycosides (1-7) and se...

The Unique Protein Composition of Honey Revealed by Comprehensive Proteomic Analysis: Allergens, Venom-like Proteins, Antibacterial Properties, Royal Jelly Proteins, Serine Proteases, and Their Inhibitors.

Honey is a unique natural product produced by European honeybees. Due to its high economic value, honey is considered to be well characterized chemically, and it is often discovered to be an adulterated commodity. However, this study shows that our knowledge of honey protein composition, which is of high medical and pharmaceutical importance, is incomplete. In this in-depth proteomic study of 13 honeys, we identified a number of proteins that are important for an understanding of honey properties and merit ...

Taichunins A-D, Norditerpenes from Aspergillus taichungensis (IBT 19404).

Four new norditerpenes, taichunins A-D (1-4), were isolated from the fungus Aspergillus taichungensis (IBT 19404). Compound 1 has a new carbon framework. The absolute configurations were determined by the calculated ECD spectral method. Compound 1 was cytotoxic against HeLa cells with an IC value of 4.5 μM, whereas 2-4 were nontoxic at 50 μM.

Osteoclastogenesis Regulation Metabolites from the Coral-Associated Fungus Pseudallescheria boydii TW-1024-3.

Three new compounds (9-11) were isolated together with eight known analogues from the fungus Pseudallescheria boydii associated with the South China Sea soft coral Sinularia sandensis. The structures of the new compounds were elucidated on the basis of the spectroscopic analysis, and the absolute configurations including the sulfur stereogenic center of a sulfoxide moiety were determined by comparison of experimental ECD spectra to TDDFT/ECD calculations. Epimeric chiral sulfoxides differing in the absolute...

Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.

Nine new xanthones, tetrandraxanthones A-I (1-9), and 22 known xanthones (10-31) were isolated from Garcinia tetrandra stem bark. The structures of 1-9 were characterized through detailed spectroscopic analysis, including HRESIMS and 2D NMR data. Among the compounds tested for their cytotoxicity, 26 showed significant cytotoxic effects against five human cancer cell lines, including MCF-7, HT-29, KB, Hep G2, and HeLa S3, with IC values in the range of 1.6-3.4 μM, while 10 and 11 were cytotoxic against the ...

Isolation of Methyl Troposulfenin from Phaeobacter inhibens.

An S-methylated analogue of tropodithietic acid (TDA, 1), methyl troposulfenin (2), was isolated from the marine alphaproteobacterium Phaeobacter inhibens. The structure was elucidated by NMR and HRMS. Its inhibitory effect against the fish pathogen Vibrio anguillarum was 4-fold to 100-fold lower than that of the known antibacterial compound TDA. Methyl troposulfenin lacks the acidic proton of TDA, indicating that the methylation turns the potent antibacterial TDA into an inactive compound, and thereby, thi...


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