Circumdatin M,a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. FM242

A new benzodiazepine alkaloid, circumdatin M (1), with a rare pyrimidone-4-pyrone moiety was isolated from a Hawaiian marine fungus Aspergillus sp. FM242. The structure of compound 1 was determined by analysis of HRMS and NMR spectroscopic data, and DP4+ NMR calculations. The absolute configurations of compound 1 were assigned by CD calculations. Compound 1 was tested inactive against A2780 and A2780CisR.     

A new nine-membered lactone from a marine fungus Cladosporium sp. F14

A new nine-membered lactone, cladospolide E (1), was isolated from a culture broth of a marine fungus Cladosporium sp. F14. The structure of compound 1 was determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR data.       

A new isobenzofuranone derivative from a marine Streptomyces sp.

One new isobenzofuranone derivative,1,4-dimethoxy-3-(3R*-hydroxy-3R*-methyl-1-tetralone)-1(3H)-isobenzofuran(1),was isolated from the broth of marine Streptomyces sp.M268.The structure was elucidated by spectroscopy characteristics as well as comparison with the literature.Compound 1 exhibited cytotoxicities against human cancer cell,HL-60,A549,and BEL-7402.     

Poecillastrin E,F, and G,cytotoxic chondropsin-type macrolides from a marine sponge Poecillastra sp.

Poecillastrin E (1), F (2), and G (3) were isolated from a marine sponge Poecillastra sp. as the cytotoxic constituents. Their planar structures were determined by analyzing the MS and NMR spectra. They are closely related to the known poecillastrin C (4). The absolute configuration of the β-hydroxyaspartic acid (OHAsp) residue was determined to be D-threo by Marfey's analysis of the hydrolysate. The mode of lactone ring formation of OHAsp residue in 1–3 was determined by selective reduction of the ester linkage followed by acid hydrolysis.     

Halichonic acid,a new rearranged bisabolene-type sesquiterpene from a marine sponge Halichondria sp.

A new compound, halichonic acid (1), was isolated from a marine sponge Halichondria sp., together with (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (2). The structure of 1 was elucidated by spectroscopic analysis and ECD spectrum calculation to be a rearranged bisabolene-type sesquiterpene having a 3-azabicyclo[3.3.1]nonene moiety. Compound 2 was cytotoxic against HeLa cells with an IC₅₀ value of 50?μM, whereas 1 did not show cytotoxicity even at 50?μM. It is possible that 1 is biosynthesized from farnesyl pyrophosphate and glycine, with rearrangement.     

Amphimedonoic acid and psammaplysene E,novel brominated alkaloids from Amphimedon sp.

Examination of the CH₂Cl₂-MeOH (1:1) extract from the Madagascan sponge Amphimedon sp. highlighted two new brominated alkaloids, amphimedonoic acid (1) and psammaplysene E (2), along with the known 3,5-dibromo-4-methoxybenzoic acid (3). Their structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS data.     

Emerixanthone E,a new xanthone derivative from deep sea fungus Emericella sp SCSIO 05240

The marine fungus Emericella sp was isolated from the deep sea sediments. The fungus was identified by its morphology and ITS region. A new emerixanthone E (1) together with four (2–5) known emodin derivatives were isolated from the metabolites of the fungus Emericella SCSIO05240. The structures were elucidated on the basis of NMR spectroscopic analysis and mass spectrometry. The biological properties of those compounds (1–5) were explored for antimicrobial, antifungal and antitumor activity.     

Diplopuupehenone, a new unsymmetrical puupehenone-related dimer from the marine sponge Dysidea sp.

A new unsymmetrical puupehenone-related dimer, diplopuupehenone, comprising puupehenone and puupehenol segments, was isolated from the marine sponge Dysidea sp., along with the known metabolites, puupehenone and bispuupehenone. The structure of diplopuupehenone was established from spectroscopic data and by spectroscopic analysis of an acetoxy derivative. Diplopuupehenone showed 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity with an IC₅₀ value of 8 μM.     

Structure of mildiomycin,a new antifungal nucleoside antibiotic

The chemical structure of mildiomycin (1) active against powdery mildews was determined by chemical degradations and physical analyses to be 2 - [(2R, 5S, 6S) - 2 - (4 - amino - 1,2 - dihydro - 5 - hydroxymethyl - 2 -oxopyrimidin -1 - yl) - 5,6 - dihydro - 5 - L - serylamino - 2H - pyran - 6 - yl] - 5 - (3H⁺ - guanidino) - 2,4 -dihydroxyvalerate as shown in Chart 1.¹     

Halichonadins A-D, new sesquiterpenoids from a sponge Halichondria sp.

A new dimeric sesquiterpenoid with two eudesmane skeletons through a urea linkage, halichonadin A (1), as well as three new eudesmane sesquiterpenoids having a carbamate, an isonitrile, or an amino functionality, halichonadins B (2), C (3), and D (4), respectively, have been isolated from a marine sponge Halichondria sp., and the gross structures and relative stereochemistry of 1-4 were elucidated on the basis of spectral data and chemical means.     

Halichonadins G-J, new sesquiterpenoids from a sponge Halichondria sp.

Three new dimeric sesquiterpenoids, halichonadins G-I (1-3), and one new eudesmane sesquiterpenoid possessing a 1-phenethyl urea moiety, halichonadin J (4), were isolated from a marine sponge Halichondria sp. Halichonadins G (1) and H (2) are homo-dimers of eudesmane sesquiterpenoid, linked through a methyl 2-{1-(2-amino-2-oxoethyl)ureido}acetate fragment and a 2-hydroxymalonamide fragment, respectively, while halichonadin I (3) is a new hetero-dimer of eudesmane sesquiterpenoid linked through a urea fragment. The structures of 1-4 were elucidated on the basis of spectroscopic data.     

Diazonamides C-E, new cytotoxic metabolites from the ascidian Diazona sp.

Three new macrocyclic peptides, diazonamides C-E (1-3), were isolated together with the previously reported diazonamides A (4) and B (5) from samples of the marine ascidian Diazona sp. collected in Indonesia. Their structures were assigned on the basis of detailed analysis of the 1D and 2D NMR and mass spectral data as well as Marfey’s analysis of the aminoacid residues. All the new compounds isolated displayed moderate cytotoxicity against a panel of three human tumor cell lines.     

A New Pregnane Glycoside from Dioscorea collettii var. hypoglauca

Morphologicaldeformationsofthemyceliaorconidiaofmicroorganismssuchascurling,swelling,hyper-divergence,beadformationandinhibitionofgermination,areofteninducedinthepresenceofbioactivesubstances".AnewscreeningbioassaymethodfordetectingthedeformationofmyceliagerminatedfromconidiaofPyriculartaoryzaeP-2bwasfirstdevelopedforthequantitativeapplicationtoscreeningantifungalandantineoplasticagentsbyH.Kobayashi'.Thisbioassayisquick,easytoperform,andhasbeenefficientlyusedinthepreliminaryscreeningofantineo…     

Stellatolide H,a cytotoxic peptide lactone from a deep-sea sponge Discodermia sp.

Stellatolide H (1) was isolated from a deep-sea sponge Discodermia sp. as the cytotoxic constituent. The planar structure of 1 was elucidated on the basis of the NMR spectroscopic and mass spectrometric data. The absolute configurations of the constituent amino acid residues were determined by the Marfey’s method. Stellatolide H (1) is a peptide lactone of the callipeltin class with its N-terminus blocked by 3-hydroxy-6,8-dimethyldeca-(4Z,6E)-dienoic acid (Hdda).     

Structure and total synthesis of chryscandin,a new antifungal antibiotic

The structure elucidation and total synthesis of chryscandin (1), a new antifungal antibiotic produced by $\text{Chrysosporium pannorum}$ No.4629, is reported.     

Ishigadine A,a new canthin-6-one alkaloid from an Okinawan marine sponge Hyrtios sp.

A new indole alkaloid with the canthin-6-one skeleton, ishigadine A, has been isolated from an Okinawan marine sponge Hyrtios sp. The structure of ishigadine A was elucidated on the basis of spectroscopic analyses. Ishigadine A is a new canthin-6-one alkaloid possessing a hydroxy group, a 1,3-dimethyl-4-methylthioimidazolium, and a 1-propylguanidine. Ishigadine A is the third canthin-6-one alkaloid from sponges. Ishigadine A might be generated from l-arginine, l-histidine, and l-tryptophan. Ishigadine A exhibited moderate cytotoxicity against L1210 murine leukemia cells.     

A New Furostanol Saponin from Dioscorea futshauensis

A new furostanol saponin presenting moderate bioacitivity of inducting morphological deformation of Pyricularia oryzae mycelia was isolated from Dioscorea futshauensis R.Kunth by bioacitivity-guided fractionation. The structure was established as 26-O-β-D-glucopyranosyl-3β,26-diol-23(S)-methoxyl-(25R)-furost-5,20(22)-diene-3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→3)]-β-D-glucopyranoside on the basis of chemical evidencesand spectral analysis,especially by 2D-NMR techniques.     

红葱中的新化学成分

通过正相和反相硅胶柱色以及高效液相色谱,从红葱60%乙醇提取物中分离得到3个新化合物,利用物理化学和光谱学方法鉴定了其结构,分别为9,9'-二羟基-8,8'-二甲氧基-1,1'-二甲基-1H,1H-['4,4']双[萘并(2,3-c)呋喃]-3,3'-二酮(1),6,8-二羟基-3,4-二甲氧基-1-甲基-蒽醌-2-羧酸甲酯(2),2-乙酰基-3,6,8-三羟基-1-甲基蒽醌(3).这3个化合物均能不同程度地诱导稻瘟霉菌丝变形,其最小变形质量浓度(Mini-mummorphologicaldeformationmassconcentration,MMDC)分别为145.8,50.2和124.8μg/mL.利用MTT法测定了化合物抑制人类红白血细胞株K562细胞生长的活性,化合物2的IC₅₀为49.1μg/mL.