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Siladenoserinols A–L: New Sulfonated Serinol Derivatives from a Tunicate as Inhibitors of p53–Hdm2 Interaction

Siladenoserinols A–L: New Sulfonated Serinol Derivatives from a Tunicate as Inhibitors of p53–Hdm2 Interaction | natural product | Scoop.it

Siladenoserinols A–L were isolated from a tunicate as inhibitors of p53–Hdm2 interaction, a promising target for cancer chemotherapy. Their structures including the absolute configurations were elucidated to be new sulfonated serinol derivatives, each of which contains a 6,8-dioxabicyclo[3.2.1]octane unit and either glycerophosphocholine or glycerophosphoethanolamine moiety. They inhibited p53–Hdm2 interaction with IC50 values of 2.0–55 μM. Among them, siladenoserinol A and B exhibited the strongest inhibition with an IC50 value of 2.0 μM. Yuichi Nakamura, Hikaru Kato, Tadateru Nishikawa, Noriyuki Iwasaki, Yoshiaki Suwa, Henki Rotinsulu, Fije Losung, Wilmar Maarisit, Remy E. P. Mangindaan, Hiroshi Morioka, Hideyoshi Yokosawa, and Sachiko Tsukamoto Org. Lett., Article ASAP DOI: 10.1021/ol3032363


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NOR-Batzelladine L from the sponge Monanchora sp. displays antiviral acyivity against Herpes Simplex virus type 1

NOR-Batzelladine L from the sponge Monanchora sp. displays antiviral acyivity against Herpes Simplex virus type 1 | natural product | Scoop.it

Althoug marine organisms produce an incredible array of bioactive natural products, only few of such secondary metabolites display anti-viral activity. The aim of this study was to evaluate antiviral activity against Herpes simplex virus type 1 (HSV-1) and Avian metapneumovirus (aMPV) of some marine natural products. HSV-1 cause herpes labials in humans and aMPV cause respiratory disease in avian, which accounts for considerable economic losses worldwide. Fourteen pure compounds isolated and identified were tested in non-toxic concentrations for virus-infected cells. Norbatzelladine L isolated from a marine sponge of the genus Monanchora displayed MNTC at 2,5µg/mL against HSV-1, with 97% of inhibition in the viral adsorption phase. Further studies are underway in order to establish the anti-viral mode-of-action of norbatzelladine L.


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goice1940's curator insight, December 25, 2013 9:31 PM

Norbatzelladine L, a marine organism, was discovered to inhibit the HSV1 adsorption phase.

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Cytotoxic Metabolites from the Antarctic Psychrophilic Fungus Oidiodendron truncatum

Cytotoxic Metabolites from the Antarctic Psychrophilic Fungus Oidiodendron truncatum | natural product | Scoop.it

Two new epipolythiodioxopiperazines, named chetracins B and C (1 and 2), and five new diketopiperazines, named chetracin D (4) and oidioperazines A–D (5, 10, 12, and 13), were isolated from the fungus Oidiodendron truncatum GW3-13, along with six known compounds (3, 6, 7, 8, 9, and 11). Their structures were elucidated by extensive NMR, MS, and CD analyses, as well as chemical transformation. An in vitro MTT cytotoxicity assay revealed potent biological activity for 1 in the nanomolar range against a panel of five human cancer lines.


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Suberitine A–D, Four New Cytotoxic Dimeric Aaptamine Alkaloids from the Marine Sponge Aaptos suberitoides

Suberitine A–D, Four New Cytotoxic Dimeric Aaptamine Alkaloids from the Marine Sponge Aaptos suberitoides | natural product | Scoop.it

Suberitine A–D (1–4), four new bis-aaptamine alkaloids with two aaptamine skeleton units, 8,9,9-trimethoxy-9H-benzo[de][1,6]-naphthyridine and demethyl(oxy)-aaptamine, linked through a rare C-3–C-3′ or C-3–C-6′ σ-bond between the 1,6-naphthyridine rings, together with two known monomers 5 and 6, were isolated from the marine sponge Aaptos suberitoides. Their structures were elucidated using NMR spectroscopy. Compounds 2 and 4 showed potent cytotoxicity against P388 cell lines, with IC50 values of 1.8 and 3.5 μM, respectively.


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Natural Products Chemistry Breaking News

Natural Products Chemistry Breaking News | natural product | Scoop.it
A recompilation of news and links about natural products, organic chemistry and science more generally ...
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Hunanamycin A, an Antibiotic from a Marine-Derived Bacillus hunanensis

Hunanamycin A, an Antibiotic from a Marine-Derived Bacillus hunanensis | natural product | Scoop.it

Hunanamycin A, the first natural product with a pyrido[1,2,3-de]quinoxaline-2,3-dione core, was isolated from a marine-derived Bacillus hunanensis. Hunanamycin A is related to a degradation product of riboflavin but has undergone an N-prenylation and subsequent cyclization. The structure, including stereochemistry, was determined by NMR and MS methods. Hunanamycin A exhibits a minimum inhibitory concentration (MIC) of 12.4 μM against the bacterial pathogen Salmonella enterica.

 

Youcai Hu, Kezhan Wang, and John B. MacMillanOrg. Lett., Article ASAPDOI: 10.1021/ol303376cPublication Date (Web): January 10, 2013


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Mandelalides A–D, Cytotoxic Macrolides from a New Lissoclinum Species of South African Tunicate

Mandelalides A–D, Cytotoxic Macrolides from a New Lissoclinum Species of South African Tunicate | natural product | Scoop.it

Mandelalides A–D are variously glycosylated, unusual polyketide macrolides isolated from a new species of Lissoclinum ascidian collected from South Africa, Algoa Bay near Port Elizabeth and the surrounding Nelson Mandela Metropole. The absolute configuration was assigned for mandelalide A after chiral GC-MS analysis of the hydrolyzed monosaccharide (2-O-methyl-α-l-rhamnose) and consideration of ROESY correlations between the monosaccharide and aglycone in the intact natural product. The resultant absolute configuration of the mandelalide A macrolide was extrapolated to propose the absolute configurations of mandelalides B–D. Remarkably, mandelalide B contained the C-4′ epimeric 2-O-methyl-6-dehydro-α-l-talose. Mandelalides A and B showed potent cytotoxicity to human NCI-H460 lung cancer cells (IC50, 12 and 44 nM, respectively) and mouse Neuro-2A neuroblastoma cells (IC50, 29 and 84 nM, respectively)


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Aromatic Polyketide Production in Cordyceps indigotica, an Entomopathogenic Fungus, Induced by Exposure to a Histone Deacetylase Inhibitor

Aromatic Polyketide Production in Cordyceps indigotica, an Entomopathogenic Fungus, Induced by Exposure to a Histone Deacetylase Inhibitor | natural product | Scoop.it

Cultivation of Cordyceps indigotica, an entomopathogenic fungus, in the presence of suberoyl bis-hydroxamic acid (an HDAC inhibitor) greatly activated its polyketide synthesis apparatus to afford six novel aromatic polyketides, indigotides C–F (1–4), 13-hydroxyindigotide A (5), and 8-O-methylindigotide B (6). The structures of these compounds were determined by NMR spectroscopic analyses. Among the compounds, indigotides C–E (1–3) possessed unprecedented dimeric polyketide frameworks possibly generated via a [4 + 2] cycloaddition or Michael type reaction.


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Totopotensamides, Polyketide–Cyclic Peptide Hybrids from a Mollusk-Associated Bacterium Streptomyces sp.

Totopotensamides, Polyketide–Cyclic Peptide Hybrids from a Mollusk-Associated Bacterium Streptomyces sp. | natural product | Scoop.it

Two new compounds, the peptide–polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey’s method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.


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