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Biomedical subjects

Matsumi Doe

Publications and source records attributed to Matsumi Doe.

14 recordsLinked to original sources
PubMed2006

Structural characterization of a specific glycopeptidolipid containing a novel N-acyl-deoxy sugar from mycobacterium intracellulare serotype 7 and genetic analysis of its glycosylation pathway.

The nontuberculous Mycobacterium avium-Mycobacterium intracellulare complex (MAC) is distributed ubiquitously in the environment and is an important cause of respiratory and lymphatic disease in humans and animals. These species produce polar glycopeptidolipids (GPLs), and of particular interest is their serotype-specific antigenicity. Structurally, GPLs contain an N-acylated tetrapeptide-amino alcohol core that is glycosylated at the C terminal with 3,4-di-O-methyl rhamnose and at the d-allo-threonine with a 6-deoxy-talose. This serotype nonspecific GPL is found in all MAC species. The serotype-specific GPLs are further glycosylated with a variable haptenic oligosaccharide at 6-deoxy-talose. At present, 31 distinct serotype-specific GPLs have been identified on the basis of oligosaccharide composition, and the complete structures of 14 serotype-specific GPLs have been defined. It is considered that the modification of the GPL structure plays an important role in bacterial physiology, pathogenesis, and host immune responses. In this study, we defined the complete structure of a novel serotype 7 GPL that has a unique terminal amido sugar. The main molecular mass is 1,874, and attached to the tetrapeptide-amino alcohol core is the serotype 7-specific oligosaccharide unit of 4-2'-hydroxypropanoyl-amido-4,6-dideoxy-2-O-methyl-beta-hexose-(1-->3)-alpha-l-rhamnose-(1-->3)-alpha-l-rhamnose-(1-->3)-alpha-l-rhamnose-(1-->2)-alpha-l-6-deoxy-talose. Moreover, we isolated and characterized the serotype 7-specific gene cluster involved in glycosylation of the oligosaccharide. Nine open reading frames (ORFs) were observed in the cluster. Based on the sequence homology, the ORFs are thought to participate in the biosynthesis of the serotype 7 GPL.

Carbohydrate Sequence↗
PubMed2006

Microbiological transformation of two labdane diterpenes, the main constituents of Madia species, by two fungi.

Microbial transformation of 13R,14R,15-trihydroxylabd-7-ene (5) and 13R,14R,15-trihydroxylabd-8(17)-ene (6) by the fungus Debaryomyces hansenii gave 1 (13R,14R,15-trihydroxy-6-oxolabd-8-ene) and 3 (7alpha,13R,14R,15-tetrahydroxy-labd-8(17)-ene), respectively. While, microbial transformation of 5 by Aspergillus niger afforded 2 (3beta,13R,14R,15-tetrahydroxy-labd-7-ene), and 13R,14R,15-trihydroxylabd-8,17-ene (6) gave 3 and 4 (3R,14R,15-3-oxotetrahydroxy-labd-7-ene). The structures of the new compounds, 1 and 2, were assigned by 1D and 2D high-field NMR spectroscopic methods. Antimicrobial activity of these compounds were tested and their MIC were determined.

Anti-Bacterial Agents↗
PubMed2006

Rings B,D-seco limonoids from the leaves of Swietenia mahogani.

Seven phragmalin limonoids of swietephragmins A-G, and two other different types of 2-hydroxy-3-O-tigloylswietenolide and deacetylsecomahoganin, were isolated along with three known limonoids from the leaves of Swietenia mahogani (Meliaceae). Their structures were determined by spectroscopic methods.

Animals↗
PubMed2006

Biscembranes from the soft coral Sarcophyton glaucum.

Four novel biscembranes have been isolated from the soft coral Sarcophyton glaucum, collected at Amami Oshima, two of which showed weak activity against proliferation of human promyelocytic leukemia cells (HL-60). Their absolute structures were determined on the basis of the CD spectra.

Animals↗
PubMed2006

The anti-Helicobacter pylori flavones in a Brazilian plant, Hyptis fasciculata, and the activity of methoxyflavones.

Two known flavonoids were isolated from a tropical medicinal plant, Hyptis fasciculata (Labiatae), found in Brazil. Flavonoids were identified as cirsilineol (1) and cirsimaritin (2) by spectroscopic means and were exhibited potent antibacterial activity against Helicobacter pylori, and cirsilineol (1) had weak antibacterial activity against Escherichia coli and Salmonella enteritidis. Following up on the relationship between anti-H. pylori activity and flavonoids with methoxy groups, several methoxy flavonoids were evaluated for proliferation of H. pylori.

Bacteria↗
PubMed2005

Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata.

[reaction: see text] 13-Hydroxy-14-nordehydrocacalohastine (2) and 13-acetoxy-14-nordehydrocacalohastine (3), two novel modified furanoeremophilane-type sesquiterpenes isolated from Trichilia cuneata, showed inhibitory activities for membrane lipid peroxidation in mitochondria and microsomes. The first, highly convergent total syntheses of new compounds 2 and 3 have also been achieved via a palladium-mediated three-component coupling reaction between 2-iodotoluene (7), 1-penten-4-yn-3-ol (8), and diethyl ethoxymethylenemalonate (9).

Combinatorial Chemistry Techniques↗
PubMed2005

Briarlides I-R, briarane diterpenes from a gorgonian Briareum sp.

Further investigations of the secondary metabolites of a gorgonian Briareum sp., collected at Amami Oshima, Kagoshima Prefecture, have yielded 10 new briarane diterpenes, briarlides I-R (1-10). The structures were elucidated on the basis of spectral analysis.

Animals↗
PubMed2004

Quantitative evaluation of d-pi interaction in copper(I) complexes and control of copper(I)-dioxygen reactivity.

Crystal structures of the copper(I) complexes 1(X), 2, and 3 of a series of tridentate ligands L1(X), L2, and L3, respectively (L1(X): p-substituted derivatives of N,N-bis[2-(2-pyridyl)ethyl]-2-phenylethylamine; X=H, Me, OMe, Cl, NO(2); L2: N,N-bis[2-(2-pyridyl)ethyl]-2-methyl-2-phenylethylamine; L3: N,N-bis[2-(2-pyridyl)ethyl]-2,2-diphenylethylamine) were solved to demonstrate that all the copper(I) complexes involve an eta(2) copper-arene interaction with the phenyl ring of the ligand sidearm. The Cu(I) ion in each complex has a distorted tetrahedral geometry consisting of the three nitrogen atoms (one tertiary amine nitrogen atom and two pyridine nitrogen atoms) and C(1)-C(2) of the phenyl ring of ligand sidearm, whereby the Cu-C distances of the copper-arene interaction significantly depend on the para substituents. The existence of the copper-arene interaction in a nonpolar organic solvent (CH(2)Cl(2)) was demonstrated by the observation of an intense MLCT band around 290 nm, and the magnitude of the interaction was evaluated by detailed analysis of the (1)H and (13)C NMR spectra and the redox potentials E(1/2) of the copper ion, as well as by means of the ligand-exchange reaction between the phenyl ring and CH(3)CN as an external ligand. The thermodynamic parameters DeltaH(o) and DeltaS(o) for the ligand-exchange reaction with CH(3)CN afforded a quantitative measure for the energy difference of the copper-arene interaction in the series of copper(I) complexes. Density functional studies indicated that the copper(I)-arene interaction mainly consists of the interaction between the d(z(2) ) orbital of Cu(I) and a pi orbital of the phenyl ring. The copper(I) complexes 1(X) reacted with O(2) at -80 degrees C in CH(2)Cl(2) to give the corresponding (micro-eta(2):eta(2)-peroxo)dicopper(II) complexes 4, the formation rates k(obs) of which were significantly retarded by stronger d-pi interaction, while complexes 2 and 3, which exhibit the strongest d-pi interaction showed significantly lower reactivity toward O(2) under the same experimental conditions. Thus, the d-pi interaction has been demonstrated for the first time to affect the copper(I)-dioxygen reactivity, and represents a new aspect of ligand effects in copper(I)-dioxygen chemistry.

Journal Article↗
PubMed2004

Antifungal limonoids from the fruits of Khaya senegalensis.

Investigation of the fruits of Khaya senegalensis resulted in the isolation of three new mexicanolide limonoids containing a rare conjugated diene lactone system named seneganolide A (1), 2-hydroxyseneganolide A (2) and 2-acetoxyseneganolide A (3). Two known limonoids, 3-deacetyl-7-deacetoxy-7-oxokhivorin (4) and methyl 6-hydroxyangolensate (5), were also found. The structures of the new compounds were elucidated on the basis of spectral methods. The antifungal activity of compounds 1, 3 and 5 was tested against the fungus Botrytis cinerea.

Antifungal Agents↗
PubMed2004

Phragmalin limonoids from Chukrasia tabularis.

Six phragmalin limonoids, named tabulalin and tabulalides A-E, were isolated from the root bark of Chukrasia tabularis (Meliaceae). Their structures were determined by spectroscopic methods, and their antifeedant properties evaluated.

Animals↗
PubMed2003

Structural analysis of sphingophospholipids derived from Sphingobacterium spiritivorum, the type species of genus Sphingobacterium.

The unique feature of the genus Sphingobacterium is the presence of sphingophospholipids and ceramides, besides diacylglycerophospholipids. As major cellular lipid components, five kinds of sphingophospholipids were purified from Sphingobacterium spiritivorum ATCC 33861(T), the type species of genus Sphingobacterium. They were identified as ceramide phosphorylethanolamines (CerPE-1 and CerPE-2), ceramide phosphoryl-myo-inositols (CerPI-1 and CerPI-2), and ceramide phosphorylmannose (CerPM-1). The ceramide of CerPE-1, CerPI-1, and CerPM-1 was composed of 15-methylhexadecasphinganine (isoheptadeca sphinganine, iso-C17:0) and 13-methyltetradecanoic acid (isopentadecanoic acid, iso-C15:0), whereas that of CerPE-2 and CerPI-2 was composed of isoheptadeca sphinganine and 2-hydroxy-13-methyltetradecanoic acid (2-hydroxy isopentadecanoic acid, 2-OH iso-C15:0). These sphingophospholipids were also found in cellular lipids of Sphingobacterium multivorum ATCC 33613(T), Sphingobacterium mizutaii ATCC 33299(T), Sphingobacterium faecium IFO 15299(T), Sphingobacterium thalpophilum ATCC 43320(T), and Sphingobacterium antarcticum ATCC 51969(T). To our knowledge, the existence of CerPM-1 is a novel sphingophospholipid through eukaryotic and prokaryotic cells.

Ceramides↗
PubMed2002

Farnesylpyridinium, an analog of isoprenoid farnesol, induces apoptosis but suppresses apoptotic body formation in human promyelocytic leukemia cells.

1-Farnesylpyridinium (FPy), an analog of isoprenoid farnesol, initially induced morphological changes similar to those of typical apoptosis in human leukemia HL-60 cells but FPy-treated cells were characterized by the absolute absence of final apoptotic events such as fragmentation into apoptotic bodies. FPy-induced cell death was considered to be apoptotic on the basis of the induction of DNA fragmentation and the protection against these events by the coaddition of a pan-caspase inhibitor. The increase in the cytoplasmic cytochrome c level supported the possibility that FPy-treated cells should have the ability to complete the entire apoptotic process ending in cell fragmentation and apoptotic body formation. At concentrations too low to induce apoptosis, FPy could suppress the induction of apoptotic body formation in HL-60 cells by typical inducers of apoptosis such as actinomycin D or anisomycin. FPy exhibited a cytochalasin-like effect on spatial arrangement of actin filament independent of its apoptosis-inducing activity.

Actin Cytoskeleton↗
PubMed2002

Three new modified limonoids from Khaya senegalensis.

Three new rings B/D opened limonoids, two rearranged phragmalin limonoids named khayanolides D and E (1 and 2), and one limonoid glucoside named khayanoside (3) were isolated as insect antifeedants from the stem bark of Egyptian Khaya senegalensis. The structures of these compounds were established by spectroscopic methods, including 2D NMR and CD.

Animals↗