Masahiko Isaka

ORCID: 0000-0002-9229-3394
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Research Areas
  • Microbial Natural Products and Biosynthesis
  • Fungal Biology and Applications
  • Phytochemical compounds biological activities
  • Marine Sponges and Natural Products
  • Chemical synthesis and alkaloids
  • Phytochemistry and Bioactivity Studies
  • X-ray Diffraction in Crystallography
  • Crystallization and Solubility Studies
  • Synthetic Organic Chemistry Methods
  • Cyclopropane Reaction Mechanisms
  • Plant biochemistry and biosynthesis
  • Entomopathogenic Microorganisms in Pest Control
  • Mycorrhizal Fungi and Plant Interactions
  • Plant Pathogens and Fungal Diseases
  • Traditional and Medicinal Uses of Annonaceae
  • Insect Pest Control Strategies
  • Crystallography and molecular interactions
  • Ferrocene Chemistry and Applications
  • Natural product bioactivities and synthesis
  • Alkaloids: synthesis and pharmacology
  • Phytochemistry and Biological Activities
  • Insect Utilization and Effects
  • Asymmetric Synthesis and Catalysis
  • Medicinal plant effects and applications
  • Natural Compound Pharmacology Studies

National Science and Technology Development Agency
2002-2025

National Center for Genetic Engineering and Biotechnology
2016-2025

National Centre for Genetic Resources and Biotechnology
2023

Hitachi (Japan)
2002-2018

Walailak University
2011

Chiang Mai University
2009

Mahidol University
2000-2008

Prince of Songkla University
2004-2008

Ibaraki University
2004-2006

The University of Tokyo
2003

Aigialomycins A−E (2−6), new 14-membered resorcylic macrolides, were isolated together with a known hypothemycin (1) from the mangrove fungus, Aigialus parvus BCC 5311. Structures of these compounds, including absolute configuration, elucidated by spectroscopic methods, chemical conversions, and X-ray crystallographic analysis. Hypothemycin aigialomycin D (5) exhibited in vitro antimalarial activity IC50 values 2.2 6.6 μg/mL, respectively, while other analogues inactive. Cytotoxicities...

10.1021/jo010930g article EN The Journal of Organic Chemistry 2002-02-07

Phomoxanthones A (1) and B (2), two novel xanthone dimers, were isolated from the endophytic fungus Phomopsis sp. BCC 1323. Structures of 1 2 elucidated by spectroscopic methods. These compounds exhibited significant in vitro antimalarial antitubercular activities cytotoxicity.

10.1021/np010006h article EN Journal of Natural Products 2001-07-13

Insect pathogenic fungi have opened up a relatively untapped area of natural product research which, unfortunately, has not received much attention to date. Found in wild abundance wet tropical Thailand, the insect are shown contribute only as controllers populations but also rich sources structurally novel biologically active substances.

10.1021/ar040247r article EN Accounts of Chemical Research 2005-09-01

Bioassay-guided fractionation of the extracts from insect pathogenic fungus Cordyceps nipponica BCC 1389 led to isolation N-hydroxy- and N-methoxy-2-pyridones, cordypyridones A−D (1−4). Structures these compounds, including absolute configuration, were determined by spectroscopic methods, chemical conversions single-crystal X-ray diffraction analyses. Codypyridones A B, atropisomers each other, exhibited potent in vitro antimalarial activity with IC50 values 0.066 0.037 μg/mL, respectively,...

10.1021/jo0100906 article EN The Journal of Organic Chemistry 2001-06-09

Two new butenolides, butyrolactones VI (1) and VII (2), were isolated together with six known compounds, I (3), II (4), IV (5), V (6), aspernolide B (7), bisdethiodi(methylthio)acetylaranotin (8) from the fungus Aspergillus terreus BCC 4651. Compound 8, exhibiting a minimum inhibitory concentration (MIC) value of 1.56 μg/ml against Mycobacterium tuberculosis H37Ra, proved to be antimycobacterial principle culture this fungus. On other hand, butyrolactone (6) showed antiplasmodial activity...

10.1248/cpb.58.1545 article EN Chemical and Pharmaceutical Bulletin 2010-01-01

Two new 10-membered lactones, namely, multiplolides A (1) and B (2), were isolated from the broth extract of fungus Xylaria multiplex BCC 1111. Chemical structures 1 2 elucidated on basis their spectral data. Multiplolides (2) exhibited antifungal activity against Candida albicans with IC50 values 7 μg/mL, respectively. Both inactive in screening systems toward malarial parasite Plasmodium falciparum (at 20 μg/mL) not cytotoxic to BC-1 KB cell lines μg/mL).

10.1021/np000291p article EN Journal of Natural Products 2001-06-22

Hirsutellone F (7), a novel alkaloid dimer, was isolated together with known monomers, hirsutellones A (1), B (2), and C (3), from the seed fungus Trichoderma sp. BCC 7579. The structure of 7 elucidated by spectroscopic analysis. Studies on biomimetic chemistry, using dimer 7, suggested that compound 8 (17,1'-dehydrohirsutellone B) should be precursor for all hirsutellones.

10.1021/ol060926x article EN Organic Letters 2006-06-01

Three new 10-membered macrolides (1−3) have been isolated from the entomopathogenic fungus Cordyceps militaris BCC 2816, together with six known compounds, cepharosporolides C (4), E (5), and F (6), 2-carboxymethyl-4-(3'-hydroxybutyl)furan (7), cordycepin (8), pyridine-2,6-dicarboxylic acid. The structures were determined by analysis of NMR data, an X-ray was performed to confirm structure 1. antimalarial activity 1−4 8 against Plasmodium falciparum K1 evaluated.

10.1021/np0401415 article EN Journal of Natural Products 2004-11-01

Seven new eremophilane-type sesquiterpenoids (1−5, 7, and 8) the known mairetolide F (6) were isolated from endophytic Xylaria sp. BCC 21097. A furofurandione (9) was also fungal extract. The structures of compounds elucidated by analyses NMR spectroscopic mass spectrometry data in combination with chemical reaction studies. Eremophilanolides possessing an α-methylene-γ-lactone (1−3) exhibited moderate cytotoxic activities, while related analogues bearing endo double bond (6 7) inactive.

10.1021/np100030x article EN Journal of Natural Products 2010-02-15

This study features the isolation and identification of 12 lanostane-type triterpenoids, namely lepiotaprocerins A–L, 1–12, from fruiting bodies Poland-collected edible mushroom Macrolepiota procera. The structures absolute configurations new compounds were ambiguously established by extensive spectroscopic analyses, ECD calculation, single-crystal X-ray diffraction analyses. Structurally, A–F, 1–6, are distinguished presence a rare "1-en-1,11-epoxy" moiety which has not been previously...

10.1021/acs.jafc.8b00287 article EN Journal of Agricultural and Food Chemistry 2018-03-06

Four chromene dimers, panusimilins A–D (1–4) (racemic mixtures), and two previously undescribed chromanes (5a/5b 6a/6b) were isolated from cultures of basidiomycete Panus similis TBRC-BCC 52578. Interestingly, synthetic compounds closely related to A–C (1–3) reported, which produced by Lewis acid promoted dimerization a plant-derived chromene, precocene II. In the present study, culture broth extract fungus P. similis. The chromane monomers shown be non-racemic mixture enantiomers, their...

10.1021/acs.jnatprod.4c01475 article EN Journal of Natural Products 2025-02-26

ABSTRACT Bioassay-guided fractionation of the extract from fermentation broth Streptomyces spectabilis BCC 4785 led to isolation three principle antimalarial agents, metacycloprodigiosin, bafilomycin A 1 , and spectinabilin. Metacycloprodigiosin exhibited potent in vitro activity against Plasmodium falciparum K1, with a 50% inhibitory concentration 0.0050 ± 0.0010 μg/ml, while its cytotoxicity was much weaker.

10.1128/aac.46.4.1112-1113.2002 article EN Antimicrobial Agents and Chemotherapy 2002-04-01

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCarbocupration of cyclopropene. A novel synthon cyclopropanone enolate and its application to [3 + 2] 2 annulationEiichi. Nakamura, Masahiko. Isaka, Satoshi. MatsuzawaCite this: J. Am. Chem. Soc. 1988, 110, 4, 1297–1298Publication Date (Print):February 17, 1988Publication History Published online1 May 2002Published inissue 17 February 1988https://doi.org/10.1021/ja00212a051RIGHTS & PERMISSIONSArticle Views498Altmetric-Citations77LEARN ABOUT THESE...

10.1021/ja00212a051 article EN Journal of the American Chemical Society 1988-02-01

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCarbocupration of cyclopropene. Asymmetric synthesis quaternary carbon centersMasahiko Isaka and Eiichi NakamuraCite this: J. Am. Chem. Soc. 1990, 112, 20, 7428–7430Publication Date (Print):September 1, 1990Publication History Published online1 May 2002Published inissue 1 September 1990https://pubs.acs.org/doi/10.1021/ja00176a072https://doi.org/10.1021/ja00176a072research-articleACS PublicationsRequest reuse permissionsArticle...

10.1021/ja00176a072 article EN Journal of the American Chemical Society 1990-09-01

Two new gamma-lactones, eutypellins A (1) and B (2), two ent-eudesmane sesquiterpenes, ent-4(15)-eudesmen-11-ol-1-one (3) ent-4(15)-eudesmen-1alpha,11-diol (4), together with three known pimarane diterpenes, diaporthein B, scopararane A, libertellenone C, were isolated from the endophytic fungus Eutypella sp. BCC 13199. The structures of these compounds elucidated by interpretation spectroscopic data. absolute configuration 4 was confirmed application modified Mosher's method. Eutypellin...

10.1021/np900316x article EN Journal of Natural Products 2009-09-09

A novel cyclodepsipeptide, cordycommunin (1), and two dihydroisocoumarins (2 3) were isolated from the insect pathogenic fungus Ophiocordyceps communis BCC 16475. The absolute configurations of amino acid residues 1 addressed by application Marfey's method. Cordycommunin (1) showed growth inhibition Mycobacterium tuberculosis H37Ra with an MIC value 15 μM. This compound also exhibited weak cytotoxicity to KB cells IC50 45 μM, while it was inactive against BC, NCI-H187, Vero cell lines at a...

10.1021/np900520b article EN Journal of Natural Products 2009-12-22

Sterostreins A-E (1, 2, 3a/3b, 4, and 5), five novel terpenoids, were isolated from cultures of the mushroom fungus Stereum ostrea BCC 22955. Sterostrein A (1) exhibited antimalarial activity (IC(50) 2.3 μg/mL) cytotoxicity 5.3-38 μg/mL).

10.1021/ol2019778 article EN Organic Letters 2011-08-17
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