Literature DB >> 24223427

Saliniquinones A-F, New Members of the Highly Cytotoxic Anthraquinone-γ-Pyrones from the Marine Actinomycete Salinispora arenicola.

Brian T Murphy1, Tadigoppula Narender, Christopher A Kauffman, Matthew Woolery, Paul R Jensen, William Fenical.   

Abstract

Six new anthraquinone-γ-pyrones, saliniquinones A-F (1-6), which are related to metabolites of the pluramycin/altromycin class, were isolated from a fermentation broth of the marine actinomycete Salinispora arenicola (strain CNS-325). Their structures were determined by analysis of one- and two-dimensional NMR spectroscopic and high-resolution mass spectrometric data. The relative and absolute configurations of compounds 1-6 were determined by analysis of NOESY NMR spectroscopic data and by comparison of circular dichroism and optical rotation data with model compounds found in the literature. Saliniquinone A (1) exhibited potent inhibition of the human colon adenocarcinoma cell line (HCT-116) with an IC50 of 9.9 × 10-9 M. In the context of the biosynthetic diversity of S. arenicola, compounds 1-6 represent secondary metabolites that appear to be strain specific and thus occur outside of the core group of compounds commonly observed from this species.

Entities:  

Year:  2010        PMID: 24223427      PMCID: PMC3820018          DOI: 10.1071/CH10068

Source DB:  PubMed          Journal:  Aust J Chem        ISSN: 0004-9425            Impact factor:   1.321


  22 in total

1.  Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. I. Producing strain, fermentation, isolation, physico-chemical properties and biological activity.

Authors:  Y Kanai; D Ishiyama; H Senda; W Iwatani; H Takahashi; H Konno; S Tokumasu; S Kanazawa
Journal:  J Antibiot (Tokyo)       Date:  2000-09       Impact factor: 2.649

2.  Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors:  Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-20       Impact factor: 15.336

3.  First enantioselective total synthesis and structure determination of the anthrapyran metabolite gamma-indomycinone.

Authors:  Lutz F Tietze; Ramakrishna Reddy Singidi; Kersten M Gericke
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

4.  Enantioselective total synthesis and structure determination of the antiherpetic anthrapyran antibiotic AH-1763 IIa.

Authors:  Lutz F Tietze; Kersten M Gericke; Ramakrishna Reddy Singidi
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-27       Impact factor: 15.336

5.  Phylogenetic diversity of gram-positive bacteria cultured from marine sediments.

Authors:  Erin A Gontang; William Fenical; Paul R Jensen
Journal:  Appl Environ Microbiol       Date:  2007-03-30       Impact factor: 4.792

6.  A new antiherpetic agent, AH-1763 IIa, produced by Streptomyces cyaneus strain no. 1763.

Authors:  M Uyeda; K Yokomizo; A Ito; K Nakayama; H Watanabe; Y Kido
Journal:  J Antibiot (Tokyo)       Date:  1997-10       Impact factor: 2.649

7.  Mapping of altromycin B-DNA adduct at nucleotide resolution in the human genomic DNA by ligation-mediated PCR.

Authors:  J H Yoon; C S Lee
Journal:  Mol Cells       Date:  2000-02-29       Impact factor: 5.034

8.  Studies on a new antibiotic SF-2330. I. Taxonomy, isolation and characterization.

Authors:  J Itoh; T Shomura; T Tsuyuki; J Yoshida; M Ito; M Sezaki; M Kojima
Journal:  J Antibiot (Tokyo)       Date:  1986-06       Impact factor: 2.649

9.  Hedamycin, a new antitumor antibiotic. I. Production, isolation, and characterization.

Authors:  H Schmitz; K E Crook; J A Bush
Journal:  Antimicrob Agents Chemother (Bethesda)       Date:  1966

10.  Gamma-indomycinone, a new pluramycin metabolite from a deep-sea derived actinomycete.

Authors:  R W Schumacher; B S Davidson; D A Montenegro; V S Bernan
Journal:  J Nat Prod       Date:  1995-04       Impact factor: 4.050

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  7 in total

Review 1.  Antimicrobial compounds from marine actinomycetes.

Authors:  Cong Wang; Yuanyu Lu; Shugeng Cao
Journal:  Arch Pharm Res       Date:  2020-07-20       Impact factor: 4.946

2.  Systematic and biotechnological aspects of halophilic and halotolerant actinomycetes.

Authors:  Javad Hamedi; Fatemeh Mohammadipanah; Antonio Ventosa
Journal:  Extremophiles       Date:  2012-11-06       Impact factor: 2.395

Review 3.  Marine Rare Actinobacteria: Isolation, Characterization, and Strategies for Harnessing Bioactive Compounds.

Authors:  Dipesh Dhakal; Anaya Raj Pokhrel; Biplav Shrestha; Jae Kyung Sohng
Journal:  Front Microbiol       Date:  2017-06-15       Impact factor: 5.640

4.  Saliniquinone Derivatives, Saliniquinones G-I and Heraclemycin E, from the Marine Animal-Derived Nocardiopsis aegyptia HDN19-252.

Authors:  Luning Zhou; Xuedong Chen; Chunxiao Sun; Yimin Chang; Xiaofei Huang; Tianjiao Zhu; Guojian Zhang; Qian Che; Dehai Li
Journal:  Mar Drugs       Date:  2021-10-14       Impact factor: 5.118

Review 5.  Marine Anthraquinones: Pharmacological and Toxicological Issues.

Authors:  Giulia Greco; Eleonora Turrini; Elena Catanzaro; Carmela Fimognari
Journal:  Mar Drugs       Date:  2021-05-13       Impact factor: 5.118

6.  Shellmycin A-D, Novel Bioactive Tetrahydroanthra-γ-Pyrone Antibiotics from Marine Streptomyces sp. Shell-016.

Authors:  Yong Han; Yan Wang; Yuehan Yang; Haotong Chen
Journal:  Mar Drugs       Date:  2020-01-16       Impact factor: 5.118

Review 7.  Anticancer Drug Discovery from Microbial Sources: The Unique Mangrove Streptomycetes.

Authors:  Jodi Woan-Fei Law; Lydia Ngiik-Shiew Law; Vengadesh Letchumanan; Loh Teng-Hern Tan; Sunny Hei Wong; Kok-Gan Chan; Nurul-Syakima Ab Mutalib; Learn-Han Lee
Journal:  Molecules       Date:  2020-11-17       Impact factor: 4.411

  7 in total

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