Literature DB >> 24328269

Napyradiomycin derivatives, produced by a marine-derived actinomycete, illustrate cytotoxicity by induction of apoptosis.

Lauge Farnaes1, Nicole G Coufal, Christopher A Kauffman, Arnold L Rheingold, Antonio G DiPasquale, Paul R Jensen, William Fenical.   

Abstract

The microbial production, isolation, and structure elucidation of four new napyradiomycin congeners (1-4) is reported. The structures of these compounds, which are new additions to the marine-derived meroterpenoids, were defined by comprehensive spectroscopic analysis and by X-ray crystallography. Using fluorescence-activated cell sorting (FACS) analysis, napyradiomycins 1-4 were observed to induce apoptosis in the colon adenocarcinoma cell line HCT-116, indicating the possibility of a specific biochemical target for this class of cytotoxins.

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Year:  2013        PMID: 24328269      PMCID: PMC3913167          DOI: 10.1021/np400466j

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  13 in total

1.  Studies on the mechanism of action of A80915A, a semi-naphthoquinone natural product, as an inhibitor of gastric (H(+)-K+)-ATPase.

Authors:  A H Dantzig; P L Minor; J L Garrigus; D S Fukuda; J S Mynderse
Journal:  Biochem Pharmacol       Date:  1991-10-24       Impact factor: 5.858

2.  A80915, a new antibiotic complex produced by Streptomyces aculeolatus. Discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation.

Authors:  D S Fukuda; J S Mynderse; P J Baker; D M Berry; L D Boeck; R C Yao; F P Mertz; W M Nakatsukasa; J Mabe; J Ott
Journal:  J Antibiot (Tokyo)       Date:  1990-06       Impact factor: 2.649

Review 3.  Natural products as sources of new drugs over the last 25 years.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2007-02-20       Impact factor: 4.050

4.  Studies on new antibiotics SF2415. II. The structural elucidation.

Authors:  S Gomi; S Ohuchi; T Sasaki; J Itoh; M Sezaki
Journal:  J Antibiot (Tokyo)       Date:  1987-06       Impact factor: 2.649

5.  Napyradiomycins A and B1: non-steroidal estrogen-receptor antagonists produced by a Streptomyces.

Authors:  Y Hori; Y Abe; N Shigematsu; T Goto; M Okuhara; M Kohsaka
Journal:  J Antibiot (Tokyo)       Date:  1993-12       Impact factor: 2.649

6.  Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete.

Authors:  Irma E Soria-Mercado; Alejandra Prieto-Davo; Paul R Jensen; William Fenical
Journal:  J Nat Prod       Date:  2005-06       Impact factor: 4.050

7.  Studies on new antibiotics SF2415. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities.

Authors:  T Shomura; S Gomi; M Ito; J Yoshida; E Tanaka; S Amano; H Watabe; S Ohuchi; J Itoh; M Sezaki
Journal:  J Antibiot (Tokyo)       Date:  1987-06       Impact factor: 2.649

8.  New antibiotic napyradiomycins A2 and B4 and stereochemistry of napyradiomycins.

Authors:  K Shiomi; H Nakamura; H Iinuma; H Naganawa; T Takeuchi; H Umezawa; Y Iitaka
Journal:  J Antibiot (Tokyo)       Date:  1987-09       Impact factor: 2.649

9.  Molecular basis for chloronium-mediated meroterpene cyclization: cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster.

Authors:  Jaclyn M Winter; Michelle C Moffitt; Emmanuel Zazopoulos; James B McAlpine; Pieter C Dorrestein; Bradley S Moore
Journal:  J Biol Chem       Date:  2007-03-28       Impact factor: 5.157

10.  Novel antibiotics napyradiomycins. Production, isolation, physico-chemical properties and biological activity.

Authors:  K Shiomi; H Iinuma; M Hamada; H Naganawa; M Manabe; C Matsuki; T Takeuchi; H Umezawa
Journal:  J Antibiot (Tokyo)       Date:  1986-04       Impact factor: 2.649

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  26 in total

1.  Meroterpenoid natural products from Streptomyces bacteria - the evolution of chemoenzymatic syntheses.

Authors:  Lauren A M Murray; Shaun M K McKinnie; Bradley S Moore; Jonathan H George
Journal:  Nat Prod Rep       Date:  2020-06-30       Impact factor: 13.423

2.  A unifying paradigm for naphthoquinone-based meroterpenoid (bio)synthesis.

Authors:  Zachary D Miles; Stefan Diethelm; Henry P Pepper; David M Huang; Jonathan H George; Bradley S Moore
Journal:  Nat Chem       Date:  2017-07-31       Impact factor: 24.427

3.  Total Enzyme Syntheses of Napyradiomycins A1 and B1.

Authors:  Shaun M K McKinnie; Zachary D Miles; Peter A Jordan; Takayoshi Awakawa; Henry P Pepper; Lauren A M Murray; Jonathan H George; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2018-12-14       Impact factor: 15.419

4.  Ecological implications of hypoxia-triggered shifts in secondary metabolism.

Authors:  Kelley A Gallagher; Greg Wanger; Jane Henderson; Mark Llorente; Chambers C Hughes; Paul R Jensen
Journal:  Environ Microbiol       Date:  2017-03-21       Impact factor: 5.491

Review 5.  Biological activities of meroterpenoids isolated from different sources.

Authors:  Neeraj Kumar Fuloria; Radhika K Raheja; Kaushal H Shah; Manisha J Oza; Yogesh A Kulkarni; Vetriselvan Subramaniyan; Mahendran Sekar; Shivkanya Fuloria
Journal:  Front Pharmacol       Date:  2022-09-19       Impact factor: 5.988

6.  Enantioselective Synthesis of Azamerone.

Authors:  Matthew L Landry; Grace M McKenna; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2019-02-08       Impact factor: 15.419

7.  Napyradiomycins CNQ525.510B and A80915C target the Hsp90 paralogue Grp94.

Authors:  Lauge Farnaes; James J La Clair; William Fenical
Journal:  Org Biomol Chem       Date:  2013-11-29       Impact factor: 3.876

8.  Characterization and Biochemical Assays of Streptomyces Vanadium-Dependent Chloroperoxidases.

Authors:  Shaun M K McKinnie; Zachary D Miles; Bradley S Moore
Journal:  Methods Enzymol       Date:  2018-04-02       Impact factor: 1.600

Review 9.  Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases.

Authors:  Jeffrey D Rudolf; Chin-Yuan Chang
Journal:  Nat Prod Rep       Date:  2020-03-25       Impact factor: 13.423

Review 10.  A Review: Halogenated Compounds from Marine Actinomycetes.

Authors:  Cong Wang; Weisheng Du; Huanyun Lu; Jianzhou Lan; Kailin Liang; Shugeng Cao
Journal:  Molecules       Date:  2021-05-07       Impact factor: 4.411

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