OP Bio Factory Co.

Okinawa, Japan

OP Bio Factory Co.

Okinawa, Japan

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Ueno S.,Kyoto University | Yanagita R.C.,Kagawa University | Murakami K.,Kyoto University | Murakami A.,Kyoto University | And 4 more authors.
Bioscience, Biotechnology and Biochemistry | Year: 2012

Six bryostatins were isolated from Japanese bryozoan by evaluating their binding to the C1B domain of protein kinase Cδ (PKCδ). Structure-activity studies of bryostatins 4, 10, and 14 suggested that the ester group at C20 was not necessary for binding to and activating PKCδ. These bryostatins showed significant anti-tumorpromoting activity in induction tests with the Epstein-Barr virus early antigen.


Govindam S.V.S.,Nagoya University | Choi B.-K.,Nagoya University | Yoshioka Y.,Hiroshima University | Kanamoto A.,OP Bio Factory Co. | And 3 more authors.
Bioscience, Biotechnology and Biochemistry | Year: 2012

A library of extracts established from hundreds of marine organisms was screened by a cytotoxicity test. The active organic extract of an Okinawan marine sponge of the genus Dysidea was subjected to bioassayguided fractionation to give three new polyoxygenated steroids dysideasterols F-H (1-3), together with two known related compounds (4 and 5). Their structures were confirmed by NMR and mass spectroscopic analyses. A characteristic structural feature of 2, 4 and 5 is an allylic epoxide, whereas this epoxide undergoes ringopening by a neighbouring hydroxyl group to give a tetrahydrofuran ring in 1 and 3. All compounds 1-5 exhibited a similar cytotoxic effect with IC50 values of 0.15-0.3 μm against human epidermoid carcinoma A431 cells, demonstrating that the allylic epoxide moiety was not responsible for this cytotoxic effect.


Horikawa K.,Nagoya University | Yagyu T.,Nagoya University | Yoshioka Y.,Hiroshima University | Fujiwara T.,OP Bio Factory Co. | And 3 more authors.
Tetrahedron | Year: 2013

From an extract of the Okinawan sponge Petrosia strongylata, five novel acetylenic metabolites, petrosiols A (1)-E (5), were isolated and chemically characterized. These compounds induced nerve growth factor (NGF)-like neuronal differentiation of PC12 cells. The structure-activity relationships of the petrosiols, their derivatives, and some related known compounds suggest the importance of the rare 2,4-diyne-1,6,7,8-tetraol fragment for the neurotrophic activity of the petrosiols. © 2012 Elsevier Ltd. All rights reserved.


Govindam S.V.S.,Nagoya University | Yoshioka Y.,Hiroshima University | Kanamoto A.,OP Bio Factory Co. | Fujiwara T.,OP Bio Factory Co. | And 2 more authors.
Bioorganic and Medicinal Chemistry | Year: 2012

A new 10-membered-ring diterpene, cyclolobatriene (1), along with three other known diterpenes, lobatriene (2), eunicol (3), and fuscol (4), were isolated from the Okinawan soft coral Lobophytum pauciflorum. Their structures were established by extensive NMR spectroscopic analyses. Cyclolobatriene (1) is an additional example of rare prenylated germacrenes. Although 1, due to a 10-membered-ring structure, exists as an equilibrium mixture of three conformers, the NMR measurement in CDCl 3 at 7 °C enabled us to assign the NMR signals of the three, which is the first example of the complete NMR assignment of all the existing conformers of germacrene-type compounds. Cyclolobatriene (1) was thermally unstable and converted into 2 through Cope rearrangement upon heating at 70 °C. Eunicol (3) also possesses the same prenylated germacrene structure as 1, showing similar physico-chemical properties to 1. All four compounds 1-4 showed cytotoxic effect with IC 50's of 0.64, 0.41, 0.35 and 0.52 μM, respectively, against human epidermoid carcinoma A431 cells. © 2011 Elsevier Ltd. All rights reserved.


Singh S.B.,Merck And Co. | Singh S.B.,SBS Pharma Consulting LLC | Dayananth P.,Merck And Co. | Balibar C.J.,Merck And Co. | And 8 more authors.
Antimicrobial Agents and Chemotherapy | Year: 2015

Bacterial resistance to antibiotics continues to grow and pose serious challenges, while the discovery rate for new antibiotics declines. Kibdelomycin is a recently discovered natural-product antibiotic that inhibits bacterial growth by inhibiting the bacterial DNA replication enzymes DNA gyrase and topoisomerase IV. It was reported to be a broad-spectrum aerobic Gram-positive agent with selective inhibition of the anaerobic bacterium Clostridium difficile. We have extended the profiling of kibdelomycin by using over 196 strains of Gram-positive and Gram-negative aerobic pathogens recovered from worldwide patient populations. We report the MIC50s, MIC90s, and bactericidal activities of kibdelomycin. We confirm the Gram-positive spectrum and report for the first time that kibdelomycin shows strong activity (MIC90, 0.125 μg/ml) against clinical strains of the Gram-negative nonfermenter Acinetobacter baumannii but only weak activity against Pseudomonas aeruginosa. We confirm that well-characterized resistant strains of Staphylococcus aureus and Streptococcus pneumoniae show no cross-resistance to kibdelomycin and quinolones and coumarin antibiotics. We also show that kibdelomycin is not subject to efflux in Pseudomonas, though it is in Escherichia coli, and it is generally affected by the outer membrane permeability entry barrier in the nonfermenters P. aeruginosa and A. baumannii, which may be addressable by structure-based chemical modification. Copyright © 2015, American Society for Microbiology. All Rights Reserved.


Kobayashi K.,Kitasato University | Fukuda T.,Kitasato University | Usui T.,University of Tsukuba | Kurihara Y.,OP Bio Factory Co. | And 2 more authors.
Journal of Antibiotics | Year: 2015

Marine-derived Streptomyces sp. OPMA00072 was found to produce inhibitors of the synthesis of neutral lipids in a cell-based assay using Chinese hamster ovary (CHO) cells. A new 16-membered macrolide named bafilomycin L (BFL) (1) was isolated along with the known structurally related bafilomycin C1 (BFC1) (3) from the culture broth of the actinomycete by solvent extraction, octadecylsilyl column chromatography and HPLC. BFL inhibited cholesteryl ester (CE) synthesis in CHO cells with an IC50 value of 0.83 nM and also in mouse peritoneal macrophages with an IC50 of 6.1 nM. In addition, BFL blocked cellular acidification in HeLa cells by interfering with vacuolar H+-ATPase (V-ATPase) as well as other bafilomycins. These data strongly suggest that BFL disturbed the lysosome function to block cholesterol metabolism, leading to the inhibition of CE accumulation in mammalian cells. © 2015 Japan Antibiotics Research Association All rights reserved 0021-8820/15.


Fukuda T.,Kitasato University | Shinkai M.,Kitasato University | Sasaki E.,Kitasato University | Nagai K.,Kitasato University | And 3 more authors.
Journal of Antibiotics | Year: 2015

Eight new thiodiketopiperazines, designated as graphiumins A to H (1-8), were isolated along with bisdethiobis(methylthio)-deacetylaranotin (9) and bisdethiobis(methylthio)-deacetylapoaranotin (10) from the culture broth of the marine-derived fungus Graphium sp. OPMF00224. The structures of the graphiumins were elucidated based on spectroscopic analyses (1D and 2D NMR data, ROESY correlations and CD data) and chemical methods. The absolute configuration of the common (3S)-3-hydroxy-octanoyl acid residue in 1, 3 and 4 was determined by hydrolysis, benzoyl derivatization and HPLC analysis using a chiral column. Five graphiumins moderately inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus. © 2015 Japan Antibiotics Research Association.


Patent
Seed Research Institute Co. and Op Bio Factory Co. | Date: 2016-07-06

Provided are a compound having a novel mother nucleus, which can be a promising drug discovery seed compound, use thereof as an antifungal agent, and a production method thereof and the like. A compound represented by the following formula:


Patent
Op Bio Factory Co. and Seed Research Institute Co. | Date: 2014-08-29

Provided are a compound having a novel mother nucleus, which can be a promising drug discovery seed compound, use thereof as an antifungal agent, and a production method thereof and the like. A compound represented by the following formula: or a pharmaceutically acceptable salt thereof, and an antifungal agent containing same, and the like.


PubMed | Kitasato University and OP BIO FACTORY Co.
Type: Journal Article | Journal: The Journal of antibiotics | Year: 2015

Eight new thiodiketopiperazines, designated as graphiumins A to H (1-8), were isolated along with bisdethiobis(methylthio)-deacetylaranotin (9) and bisdethiobis(methylthio)-deacetylapoaranotin (10) from the culture broth of the marine-derived fungus Graphium sp. OPMF00224. The structures of the graphiumins were elucidated based on spectroscopic analyses (1D and 2D NMR data, ROESY correlations and CD data) and chemical methods. The absolute configuration of the common (3S)-3-hydroxy-octanoyl acid residue in 1, 3 and 4 was determined by hydrolysis, benzoyl derivatization and HPLC analysis using a chiral column. Five graphiumins moderately inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus.

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