Faculty Profiles - KITA, Masaki

Papers - KITA, Masaki

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Discovery and Use of Natural Products and Derivatives as Chemical Probes Invited Reviewed

Kita, M; Kigoshi, H

DISCOVERY AND UTILITY OF CHEMICAL PROBES IN TARGET DISCOVERY Vol. 16 page： 124 - 149 2021

Acyl-CoA dehydrogenase long chain (ACADL) is a target protein of stylissatin A, an anti-inflammatory cyclic heptapeptide Reviewed

Menghua Zhang, Taiki Sunaba, Yiting Sun, Takahiro Shibata, Kazunori Sasaki, Hiroko Isoda, Hideo Kigoshi, Masaki Kita

The Journal of Antibiotics Vol. 73 ( 8 ) page： 589 - 592 2020.8

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Springer Science and Business Media LLC

Stylissatin A (SA) is a cyclic heptapeptide isolated from the marine sponge Stylissa massa. SA shows anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cells, but the detailed mechanism of action remains unclear. Here we report that D-Tyr1-tBuSA, a more potent SA derivative, inhibited production of the proinflammatory cytokines Interleukin-6 (IL-6) and tumor necrosis factor alpha (TNF-α) in LPS-stimulated RAW264.7 cells (EC50 = 1.4 and 5.9 μM, respectively). This compound also inhibited the LPS-stimulated expression of inducible nitric oxide synthase (iNOS) at 20 μM. Using a biotin derivative of SA, acyl-CoA dehydrogenase long chain (ACADL) was identified as a target protein of SA and its derivatives. It is proposed that SA and its derivatives might suppress the β-oxidation of fatty acids by ACADL, and the accumulation of fatty acids on macrophages would inhibit the nuclear factor-kappa B (NF-κB) signaling pathway and iNOS expression to show anti-inflammatory activity. Our research might provide a new mechanism of inflammation in macrophages, and contribute to the development of treatments for inflammatory diseases.

DOI： 10.1038/s41429-020-0322-5

Web of Science

PubMed

Other Link： http://www.nature.com/articles/s41429-020-0322-5

Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae) Reviewed International coauthorship

Minako Hirukawa, Menghua Zhang, Lazaro M. Echenique–Diaz, Koji Mizota, Satoshi D. Ohdachi, Gerardo Begué–Quiala, Jorge L. Delgado–Labañino, Jorgelino Gámez–Díez, José Alvarez–Lemus, Leandro Galano Machado, Miguel Suárez Núñez, Takahiro Shibata, Hideo Kigoshi, Masaki Kita

Tetrahedron Letters Vol. 61 ( 26 ) page： 152005 - 152005 2020.6

Language：English Publishing type：Research paper (scientific journal) Publisher：Elsevier BV

The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-alpha in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities. (C) 2020 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2020.152005

Web of Science

N,N-Dimethylaminopyrene as a fluorescent affinity mass tag for ligand-binding mode analysis Reviewed

Atsushi Arai, Rei Watanabe, Atsunori Hattori, Keita Iio, Yaping Hu, Kozo Yoneda, Hideo Kigoshi, Masaki Kita

Scientific Reports Vol. 10 ( 1 ) page： 7311 2020.4

哺乳類由来の神経毒の化学生物学研究

北将樹

化学工業 Vol. 71 page： 73 - 78 2020.1

A Glucosylated Steroid from the Active Fraction of Indonesian <i>Ficus deltoidea</i> Leaves Reviewed International coauthorship

Murni, A; Yuliansih, P; Mohamad, K; Kita, M; Hanif, N

8TH INTERNATIONAL CONFERENCE OF THE INDONESIAN CHEMICAL SOCIETY (ICICS)) 2019 Vol. 2243 2020

Post K-Pg diversification of the mammalian order Eulipotyphla as suggested by phylogenomic analyses of ultra-conserved elements. Reviewed

Sato JJ, Bradford TM, Armstrong KN, Donnellan SC, Echenique-Diaz LM, Begué-Quiala G, Gámez-Díez J, Yamaguchi N, Nguyen ST, Kita M, Ohdachi SD

Molecular phylogenetics and evolution Vol. 141 page： 106605 2019.12

生理活性蛍光リガンドとLA-LDI MS 〜標的生体分子の結合位置解析法の開発〜 Invited Reviewed

北将樹

生命化学研究レター Vol. 59 page： 7-11 2019.11

Synthesis and Biological Activities of Aplyronine A Analogues toward the Development of Antitumor Protein-Protein Interaction Inducers between Actin and Tubulin: Conjugation of the C1-C9 Macrolactone Part and the C24-C34 Side Chain. Reviewed

Futaki K, Takahashi M, Tanabe K, Fujieda A, Kigoshi H, Kita M

ACS omega Vol. 4 ( 5 ) page： 8598 - 8613 2019.5

Anti-inflammatory marine cyclic peptide stylissatin A and its derivatives inhibit differentiation of murine preadipocytes. Reviewed

Zhang M, Sunaba T, Sun Y, Sasaki K, Isoda H, Kigoshi H, Kita M

Chemical communications (Cambridge, England) Vol. 55 ( 38 ) page： 5471 - 5474 2019.5

Pursue an Interdisciplinary Natural Products Chemist Invited Reviewed

Masaki Kita

Journal of Synthetic Organic Chemistry, Japan Vol. 77 ( 4 ) page： 371 - 373 2019.4

野生のキューバソレノドン（アルミキ）Solenodon cubanus の生態を垣間見る

大舘智志, ラザロエチェニケ–ディアス, ヘラルドベゲ–キアラ, 溝田浩二, 北将樹

哺乳類科学 Vol. 58 ( 2 ) page： 204 2018.12

Specific protein-labeling and ligand-binding position analysis with amidopyrene probes as LDI MS tags. Reviewed

Watanabe R, Hu Y, Iio K, Yoneda K, Hattori A, Arai A, Kigoshi H, Kita M

Organic & biomolecular chemistry Vol. 16 ( 42 ) page： 7883 - 7890 2018.10

Synthesis of the trisoxazole macrolactone of mycalolides via template-directed E-selective ring-closing metathesis Reviewed

Masaki Kita, Shun Watanabe, Hirotaka Oka, Hideo Kigoshi

Tetrahedron Letters Vol. 59 ( 41 ) page： 3664 - 3668 2018.10

Structure Analysis of Marine Natural Products and Their Binding Position Analysis on the Target Molecules by Using Mass Spectrometry

Kita Masaki

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN Vol. 76 ( 5 ) page： 442-445 2018.5

質量分析を用いた海洋天然物の構造解析および標的分子における結合位置解析 Invited Reviewed

北将樹

有機合成化学協会誌 Vol. 76 page： 442-445 2018.5

Sydowianumols A, B, and C, Three New Compounds from Discomycete Poculum pseudosydowianum Reviewed

Kawashima Daiki, Hosoya Tsuyoshi, Tomoda Hiroshi, Kita Masaki, Shigemori Hideyuki

CHEMICAL & PHARMACEUTICAL BULLETIN Vol. 66 ( 8 ) page： 826 - 829 2018

Structure analysis of marine natural products and their binding position analysis on the target molecules by using mass spectrometry Reviewed

Masaki Kita

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry Vol. 76 ( 5 ) page： 442 - 445 2018

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Society of Synthetic Organic Chemistry

In this review, two marine natural products, durinskiol A, a huge polyol compound from the cultured symbiotic dinoflagellate Durinskia sp., and aplyronine A, an antitumor macrolide from the sea hare Aplysia sp., are highlighted. We have developed a fluorescent labeling method for MS/MS analysis to establish the planar structure of durinskiol A. We also discovered 6-amidopyrene as a highly detectable tag for label-assisted laser desorption/ionization mass spectrometry (LA-LDI MS) without matrixes. Two amidopyrene derivatives of aplyronine A were synthesized, and their LA-LDI MS and MS/MS analyses to determine the binding position of the target protein actin are described.

DOI： 10.5059/yukigoseikyokaishi.76.442

Web of Science

Scopus

Development of photoaffinity derivatives of the antitumor macrolide aplyronine A, a PPI-inducer between actin and tubulin Reviewed

Masaki Kita, Kota Yamagishi, Kota Tsuchiya, Yu Seguchi, Hiroki Nakane, Hideo Kigoshi

BIOORGANIC & MEDICINAL CHEMISTRY Vol. 25 ( 24 ) page： 6322 - 6331 2017.12

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

The antitumor and actin-depolymerizing marine macrolide aplyronine A (ApA) synergistically binds to tubulin in association with actin, and prevents spindle formation and mitosis. While the crystal structure of the actin ApA complex was solved in 2006, its interaction with the tubulin heterodimer has not been clarified. To investigate the binding modes of ApA as a unique protein-protein interaction (PPI)-inducer between these two cytoskeletal proteins, we prepared its photoaffinity acetylene and fluorescent derivatives with the aid of molecular modeling studies for probe design. Among these three derivatives, the ApA-PPA-TAMRA probe specifically photoreacted with both actin and tubulin in vitro. However, the photolabeling yield of tubulin was quite low (up to similar to 1%), and one of the major side-reactions was the addition of a water molecule to the carbene species generated from an aryldiazirine moiety on the hydrophilic surface of actin. (C) 2017 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2017.09.044

Web of Science

PubMed

哺乳類の神経毒 Invited

北　将樹

Clinical Neuroscience Vol. 35 page： 1453-1456 2017.12

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Papers - KITA, Masaki