Literature DB >> 33848174

Neopetrothiazide: An Intriguing Pentacyclic Thiazide Alkaloid from the Sponge Neopetrosia sp.

Dongdong Wang1, Wei Jiang1,2, Chang-Kwon Kim1, Heidi R Bokesch1,3, Girma M Woldemichael1,3, Berkley E Gryder4,5, John F Shern4, Javed Khan4, Barry R O'Keefe1,6, John A Beutler1, Kirk R Gustafson1.   

Abstract

Neopetrothiazide (1), a pentacyclic isoquinoline quinone, was isolated from a Neopetrosia sp. sponge. The structure elucidation was facilitated by utilizing long-range heteronuclear single quantum multiple bond correlation (LR-HSQMBC) and heteronuclear multiple bond correlation (HMBC) nuclear magnetic resonance (NMR) pulse sequences optimized to detect four- and five-bond 1H-13C heteronuclear correlations. These NMR experiments can help assign proton-deficient structural motifs like neopetrothiazide (1), which has 14 contiguous nonprotonated centers (C, N, and S). Neopetrothiazide (1), with an unprecedented thiazide-fused structural scaffold, is the first natural product containing a thiazide moiety.

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Year:  2021        PMID: 33848174      PMCID: PMC9341131          DOI: 10.1021/acs.orglett.1c00743

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.072


  16 in total

1.  Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp..

Authors:  Naoya Oku; Shigeki Matsunaga; Rob W M van Soest; Nobuhiro Fusetani
Journal:  J Nat Prod       Date:  2003-08       Impact factor: 4.050

2.  PAX3-FOXO1 Establishes Myogenic Super Enhancers and Confers BET Bromodomain Vulnerability.

Authors:  Berkley E Gryder; Marielle E Yohe; Hsien-Chao Chou; Xiaohu Zhang; Joana Marques; Marco Wachtel; Beat Schaefer; Nirmalya Sen; Young Song; Alberto Gualtieri; Silvia Pomella; Rossella Rota; Abigail Cleveland; Xinyu Wen; Sivasish Sindiri; Jun S Wei; Frederic G Barr; Sudipto Das; Thorkell Andresson; Rajarshi Guha; Madhu Lal-Nag; Marc Ferrer; Jack F Shern; Keji Zhao; Craig J Thomas; Javed Khan
Journal:  Cancer Discov       Date:  2017-04-26       Impact factor: 39.397

Review 3.  PAX3-FOXO1: Zooming in on an "undruggable" target.

Authors:  Marco Wachtel; Beat W Schäfer
Journal:  Semin Cancer Biol       Date:  2017-11-14       Impact factor: 15.707

4.  Neopetrosia de Laubenfels, 1949 from Brazil: description of a new species and a review of records (Haplosclerida: Demospongiae: Porifera).

Authors:  George Garcia Santos; Joana Sandes; Abigail Cabral; Ulisses Pinheiro
Journal:  Zootaxa       Date:  2016-05-24       Impact factor: 1.091

5.  Xestoproxamines A-C from Neopetrosia proxima. Assignment of absolute stereostructure of bis-piperidine alkaloids by integrated degradation-CD analysis.

Authors:  Brandon I Morinaka; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2011-02-22       Impact factor: 4.050

Review 6.  Marine natural products.

Authors:  Anthony R Carroll; Brent R Copp; Rohan A Davis; Robert A Keyzers; Michèle R Prinsep
Journal:  Nat Prod Rep       Date:  2020-02-26       Impact factor: 13.423

Review 7.  PAX3-FOXO1 fusion gene in rhabdomyosarcoma.

Authors:  Corinne M Linardic
Journal:  Cancer Lett       Date:  2008-05-23       Impact factor: 8.679

8.  Exiguaquinol: a novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori MurI.

Authors:  Priscila de Almeida Leone; Anthony R Carroll; Leanne Towerzey; Gordon King; Bernadette M McArdle; Gunther Kern; Stewart Fisher; John N A Hooper; Ronald J Quinn
Journal:  Org Lett       Date:  2008-05-20       Impact factor: 6.005

9.  Araguspongines K and L, new bioactive bis-1-oxaquinolizidine N-oxide alkaloids from Red Sea specimens of Xestospongia exigua.

Authors:  Khaled Y Orabi; Khalid A El Sayed; Mark T Hamann; D Chuck Dunbar; Mansour S Al-Said; Tatsuo Higa; Michelle Kelly
Journal:  J Nat Prod       Date:  2002-12       Impact factor: 4.050

10.  Chemical genomics reveals histone deacetylases are required for core regulatory transcription.

Authors:  Berkley E Gryder; Lei Wu; Girma M Woldemichael; Silvia Pomella; Taylor R Quinn; Paul M C Park; Abigail Cleveland; Benjamin Z Stanton; Young Song; Rossella Rota; Olaf Wiest; Marielle E Yohe; Jack F Shern; Jun Qi; Javed Khan
Journal:  Nat Commun       Date:  2019-07-08       Impact factor: 14.919

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  1 in total

1.  Phylogeny-Informed Synthetic Biology Reveals Unprecedented Structural Novelty in Type V Glycopeptide Antibiotics.

Authors:  Min Xu; Wenliang Wang; Nicholas Waglechner; Elizabeth J Culp; Allison K Guitor; Gerard D Wright
Journal:  ACS Cent Sci       Date:  2022-04-27       Impact factor: 18.728

  1 in total

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