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  1. Article ; Online: Total Syntheses of Lycopodium and Monoterpenoid Indole Alkaloids Based on Biosynthesis-Inspired Strategies.

    Takayama, Hiromitsu

    Chemical & pharmaceutical bulletin

    2020  Volume 68, Issue 2, Page(s) 103–116

    Abstract: The merits of biogenetic considerations in the chemical syntheses of natural products have been emphasized by describing the total syntheses of Lycopodium alkaloids; lycodine, flabellidine, lycopodine, and flabelliformine, as well as monoterpenoid indole ...

    Abstract The merits of biogenetic considerations in the chemical syntheses of natural products have been emphasized by describing the total syntheses of Lycopodium alkaloids; lycodine, flabellidine, lycopodine, and flabelliformine, as well as monoterpenoid indole alkaloids; C-mavacurine, kopsiyunnanine K, koumine, and 11-methoxy-19R-hydroxygelselegine.
    MeSH term(s) Alkaloids/chemical synthesis ; Alkaloids/chemistry ; Biological Products/chemical synthesis ; Biological Products/chemistry ; Chemistry Techniques, Synthetic/methods ; Lycopodium/chemistry ; Secologanin Tryptamine Alkaloids/chemical synthesis ; Secologanin Tryptamine Alkaloids/chemistry
    Chemical Substances Alkaloids ; Biological Products ; Secologanin Tryptamine Alkaloids
    Language English
    Publishing date 2020-02-02
    Publishing country Japan
    Document type Journal Article ; Review
    ZDB-ID 213307-6
    ISSN 1347-5223 ; 0009-2363
    ISSN (online) 1347-5223
    ISSN 0009-2363
    DOI 10.1248/cpb.c19-00872
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 770: Show issues Location:
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  2. Article ; Online: Simultaneous determination of intracellular reduced and oxidized glutathiones by the König reaction.

    Mochizuki, Ryu / Kobayashi, Akane / Takayama, Hiromitsu / Toida, Toshihiko / Ogra, Yasumitsu

    Analytical methods : advancing methods and applications

    2023  Volume 15, Issue 28, Page(s) 3426–3431

    Abstract: The König reaction is commonly used for the detection of cyanide and its derivatives, including thiocyanate and selenocyanate. We found that this reaction can be used to quantify glutathione fluorometrically, and applied it to the simultaneous ... ...

    Abstract The König reaction is commonly used for the detection of cyanide and its derivatives, including thiocyanate and selenocyanate. We found that this reaction can be used to quantify glutathione fluorometrically, and applied it to the simultaneous determination of reduced and oxidized glutathiones (GSH and GSSG) using a conventional LC system with isocratic elution. The limits of detection were 6.04 nM and 9.84 nM for GSH and GSSG, respectively, and the limits of quantification were 18.3 nM and 29.8 nM, respectively. We also determined GSH and GSSG levels in PC12 cells exposed to paraquat, an oxidative stressor, and observed a decrease in GSH/GSSG ratio, as expected. Total GSH levels quantified by this method and by the conventional colorimetric method with 5,5'-dithiobis(2-nitrobenzoic acid) were comparable. Our new application of the König reaction offers a reliable and useful method to simultaneously quantify intracellular GSH and GSSG.
    MeSH term(s) Rats ; Animals ; Glutathione Disulfide/metabolism ; Glutathione ; Oxidation-Reduction ; Paraquat
    Chemical Substances Glutathione Disulfide (ULW86O013H) ; Glutathione (GAN16C9B8O) ; Paraquat (PLG39H7695)
    Language English
    Publishing date 2023-07-20
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2515210-5
    ISSN 1759-9679 ; 1759-9660
    ISSN (online) 1759-9679
    ISSN 1759-9660
    DOI 10.1039/d3ay00860f
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Recent Progress in the Chemistry of Pandanus Alkaloids.

    Tan, Mario A / Takayama, Hiromitsu

    The Alkaloids. Chemistry and biology

    2019  Volume 82, Page(s) 1–28

    Abstract: The genus Pandanus (Pandanaceae) is widely distributed in the tropical and subtropical regions. With about 700 species worldwide, three Pandanus species (P. amaryllifolius, P. utilis, and P. dubius) have been investigated and found to contain new ... ...

    Abstract The genus Pandanus (Pandanaceae) is widely distributed in the tropical and subtropical regions. With about 700 species worldwide, three Pandanus species (P. amaryllifolius, P. utilis, and P. dubius) have been investigated and found to contain new alkaloids possessing a pyrrolidinyl-α,β-unsaturated γ-lactone, a γ-butylidene-α-methyl-α,β-unsaturated γ-lactam, and/or indolizidine residues. Several total syntheses of Pandanus alkaloids have been accomplished. Several pharmacological studies on Pandanus species, including scientific validations of their antibacterial, antiinflammatory, antidiarrheal, and cytotoxic activities, have been conducted in relation to their traditional folk medicine uses.
    MeSH term(s) Alkaloids/chemistry ; Alkaloids/metabolism ; Alkaloids/pharmacology ; Molecular Structure ; Pandanaceae/chemistry ; Quantum Theory
    Chemical Substances Alkaloids
    Language English
    Publishing date 2019-02-26
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 7577-2
    ISSN 1099-4831 ; 0099-9598
    ISSN 1099-4831 ; 0099-9598
    DOI 10.1016/bs.alkal.2018.12.001
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Identification of a regiospecific

    Wang, Jichen / Suzuki, Hideyuki / Nakashima, Nanako / Kitajima, Mariko / Takayama, Hiromitsu / Saito, Kazuki / Yamazaki, Mami / Yoshimoto, Naoko

    Plant biotechnology (Tokyo, Japan)

    2022  Volume 39, Issue 3, Page(s) 281–289

    Abstract: Marasmin [ ...

    Abstract Marasmin [
    Language English
    Publishing date 2022-11-05
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 2210142-1
    ISSN 1347-6114 ; 1342-4580
    ISSN (online) 1347-6114
    ISSN 1342-4580
    DOI 10.5511/plantbiotechnology.22.0619a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Asymmetric Total Synthesis and Structure Elucidation of Huperzine H.

    Shiomi, Shinya / Wilailak, Kaewsri / Soutome, Wataru / Takayama, Hiromitsu / Kitajima, Mariko / Ishikawa, Hayato

    The Journal of organic chemistry

    2022  Volume 87, Issue 5, Page(s) 3730–3735

    Abstract: A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama-Michael addition reaction of a pyrrole ... ...

    Abstract A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama-Michael addition reaction of a pyrrole bearing a silyl enol ether and an intramolecular S
    MeSH term(s) Cyclization ; Ethers ; Molecular Structure ; Pyrroles ; Stereoisomerism
    Chemical Substances Ethers ; Pyrroles
    Language English
    Publishing date 2022-01-18
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c02672
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.A 4473: Show issues Location:
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  6. Article ; Online: Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine.

    Sato, Keigo / Kogure, Noriyuki / Kitajima, Mariko / Takayama, Hiromitsu

    Organic letters

    2019  Volume 21, Issue 9, Page(s) 3342–3345

    Abstract: The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)- C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at ... ...

    Abstract The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)- C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C
    Language English
    Publishing date 2019-04-18
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b01084
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Total Synthesis of (-)-14-Hydroxygelsenicine and Six Biogenetically Related

    Saito, Atsushi / Kogure, Noriyuki / Kitajima, Mariko / Takayama, Hiromitsu

    Organic letters

    2019  Volume 21, Issue 17, Page(s) 7134–7137

    Abstract: The first concise and collective asymmetric total synthesis of six 14-hydroxygelsenicine- ... ...

    Abstract The first concise and collective asymmetric total synthesis of six 14-hydroxygelsenicine-related
    MeSH term(s) Alkaloids/chemical synthesis ; Alkaloids/chemistry ; Furans/chemical synthesis ; Furans/chemistry ; Gelsemium/chemistry ; Indole Alkaloids/chemical synthesis ; Indole Alkaloids/chemistry ; Molecular Conformation ; Stereoisomerism
    Chemical Substances (-)-14-hydroxygelsenicine ; Alkaloids ; Furans ; Indole Alkaloids ; gelsefuranidine
    Language English
    Publishing date 2019-08-12
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b02703
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Asymmetric Total Synthesis and Structure Elucidation of Huperzine H

    Shiomi, Shinya / Wilailak, Kaewsri / Soutome, Wataru / Takayama, Hiromitsu / Kitajima, Mariko / Ishikawa, Hayato

    Journal of organic chemistry. 2022 Jan. 18, v. 87, no. 5

    2022  

    Abstract: A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama–Michael addition reaction of a pyrrole ... ...

    Abstract A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama–Michael addition reaction of a pyrrole bearing a silyl enol ether and an intramolecular SN2 cyclization reaction with iodinated pyrrole acting as an effective nucleophile for the formation of the nine-membered ring. As a result, the relative and absolute stereochemistry of huperzine H is established.
    Keywords Lewis bases ; cyclization reactions ; diastereoselectivity ; organic chemistry ; pyrroles ; silyl enol ethers ; stereochemistry
    Language English
    Dates of publication 2022-0118
    Size p. 3730-3735.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c02672
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  9. Article ; Online: Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives.

    Onozawa, Tadayoshi / Kitajima, Mariko / Kogure, Noriyuki / Takayama, Hiromitsu

    The Journal of organic chemistry

    2018  Volume 83, Issue 24, Page(s) 15312–15322

    Abstract: The first asymmetric total synthesis of ophiorrhisine A (1), a new cyclic tetrapeptide isolated from Ophiorrhiza nutans, was accomplished via an intramolecular aromatic nucleophilic substitution reaction ( ... ...

    Abstract The first asymmetric total synthesis of ophiorrhisine A (1), a new cyclic tetrapeptide isolated from Ophiorrhiza nutans, was accomplished via an intramolecular aromatic nucleophilic substitution reaction (IMS
    Language English
    Publishing date 2018-12-04
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.8b02554
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: Monoterpenoid Bisindole Alkaloids.

    Kitajima, Mariko / Takayama, Hiromitsu

    The Alkaloids. Chemistry and biology

    2016  Volume 76, Page(s) 259–310

    Abstract: This chapter covers the literature on bisindole alkaloids consisting of monoterpenoid indoles, published up to June 2015. Bisindole alkaloids isolated from plants belonging to the families Apocynaceae and Loganiaceae, including Iboga-vobasine type, ... ...

    Abstract This chapter covers the literature on bisindole alkaloids consisting of monoterpenoid indoles, published up to June 2015. Bisindole alkaloids isolated from plants belonging to the families Apocynaceae and Loganiaceae, including Iboga-vobasine type, Aspidosperma-Aspidosperma type, eburnan-Aspidosperma type, Strychnos-Strychnos type, macroline-macroline type, and so on, are described. Some recent syntheses of monoterpenoid bisindole alkaloids are outlined as well.
    MeSH term(s) Aspidosperma/chemistry ; Indole Alkaloids/metabolism ; Secologanin Tryptamine Alkaloids/metabolism ; Tabernaemontana/chemistry
    Chemical Substances Indole Alkaloids ; Secologanin Tryptamine Alkaloids ; eburnan ; vobasine (2134-83-0)
    Language English
    Publishing date 2016
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 7577-2
    ISSN 1099-4831 ; 0099-9598
    ISSN 1099-4831 ; 0099-9598
    DOI 10.1016/bs.alkal.2015.09.001
    Database MEDical Literature Analysis and Retrieval System OnLINE

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