ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

First Enantiospecific Syntheses of Marine Merosesquiterpenes Neopetrosiquinones A and B: Evaluation of Biological Activity

View Author Information
Laboratoire de Chimie Organique Appliquée, Département de Chimie, Faculté des Sciences, Université Abdelmalek Essaâdi, Tetouan, Morocco
§ Instituto de Biopatología y Medicina Regenerativa (IBIMER) and §Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain
*E-mail: [email protected] (R. Chahboun).
*Tel: (+34) 958 248 089. E-mail: [email protected] (E. Alvarez-Manzaneda).
Cite this: J. Nat. Prod. 2015, 78, 5, 1026–1036
Publication Date (Web):April 23, 2015
https://doi.org/10.1021/np500975b
Copyright © 2015 The American Chemical Society and American Society of Pharmacognosy

    Article Views

    1223

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    The first enantiospecific syntheses of neopetrosiquinones A (6) and B (7), two merosesquiterpenes isolated from the deep-water sponge Neopetrosia cf. proxima, from the labdane diterpene trans-communic acid (10) have been achieved. A key step of the synthetic sequence is the simultaneous aromatization of the C ring and the benzylic oxidation on C-7 of an advanced intermediate, mediated by the oxygen–DDQ system. The in vitro antiproliferative activities of neopetrosiquinone B (7) and of the synthetic intermediates 8 and 9 against human breast (MCF-7), lung (A-549), and colon (T-84) tumor cell lines have been assayed. The most potent was compound 9 (IC50 = 4.1 μM), which was twice as active as natural compound 7 (IC50 = 8.3 μM) against A-549 cells. In addition, the treatment with these compounds resulted in an induction of apoptosis. These findings indicate that the terpene benzoquinones reported here might be potentially useful as anticancer agents.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Copies of 1H and 13C NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 11 publications.

    1. Fermín Jiménez, Antonio Fernández, Ettahir Boulifa, Ahmed Ibn Mansour, Ramón Alvarez-Manzaneda, Rachid Chahboun, and Enrique Alvarez-Manzaneda . Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E. The Journal of Organic Chemistry 2017, 82 (18) , 9550-9559. https://doi.org/10.1021/acs.joc.7b01551
    2. Juan J. Guardia, Rubén Tapia, Soumicha Mahdjour, Fernando Rodriguez-Serrano, Nuria Mut-Salud, Rachid Chahboun, and Enrique Alvarez-Manzaneda . Antiproliferative Activity of Natural Taiwaniaquinoids and Related Compounds. Journal of Natural Products 2017, 80 (2) , 308-318. https://doi.org/10.1021/acs.jnatprod.6b00700
    3. Suven Das. Annulations involving p -benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules. New Journal of Chemistry 2024, 48 (18) , 8243-8276. https://doi.org/10.1039/D4NJ00876F
    4. Wei-Zhuo Tang, Hui-Min Zhao, Yuan Tian, Shu-Wen Dai, Ao Zhang, Hou-Wen Lin, Cui-Xian Zhang, Fan Yang. Merosesquiterpenes from the marine sponge Spongia pertusa Esper and their antifungal activities. Tetrahedron Letters 2022, 93 , 153690. https://doi.org/10.1016/j.tetlet.2022.153690
    5. Chuanke Chong, Qunlong Zhang, Jia Ke, Haiming Zhang, Xudong Yang, Bingjian Wang, Wei Ding, Zhaoyong Lu. Total Synthesis of Anti‐Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structural Reassignment of Dysiherbol A. Angewandte Chemie 2021, 133 (25) , 13926-13932. https://doi.org/10.1002/ange.202100541
    6. Chuanke Chong, Qunlong Zhang, Jia Ke, Haiming Zhang, Xudong Yang, Bingjian Wang, Wei Ding, Zhaoyong Lu. Total Synthesis of Anti‐Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structural Reassignment of Dysiherbol A. Angewandte Chemie International Edition 2021, 60 (25) , 13807-13813. https://doi.org/10.1002/anie.202100541
    7. Soumicha Mahdjour, Juan J. Guardia, Fernando Rodríguez-Serrano, José Manuel Garrido, Isabel Blancas López-Barajas, Nuria Mut-Salud, Rachid Chahboun, Enrique Alvarez-Manzaneda. Synthesis and antiproliferative activity of podocarpane and totarane derivatives. European Journal of Medicinal Chemistry 2018, 158 , 863-873. https://doi.org/10.1016/j.ejmech.2018.09.051
    8. Pablo García, Ángela Hernández, Arturo San Feliciano, Mª Castro. Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †. Marine Drugs 2018, 16 (9) , 292. https://doi.org/10.3390/md16090292
    9. Mathéo Berthet, Jean Martinez, Isabelle Parrot. MgI 2 ‐chemoselective cleavage for removal of amino acid protecting groups: A fresh vision for peptide synthesis. Peptide Science 2017, 108 (2) https://doi.org/10.1002/bip.22908
    10. John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2017, 34 (3) , 235-294. https://doi.org/10.1039/C6NP00124F
    11. James R. Hanson. Diterpenoids of terrestrial origin. Natural Product Reports 2016, 33 (10) , 1227-1238. https://doi.org/10.1039/C6NP00059B

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect