Marthiapeptide A, an Anti-infective and Cytotoxic Polythiazole Cyclopeptide from a 60 L Scale Fermentation of the Deep Sea-Derived <i>Marinactinospora thermotolerans</i> SCSIO 00652

Zhou, Xiaofeng; Huang, Hongbo; Chen, Yuchan; Tan, Jia‐Heng; Song, Yongxiang; Zou, Jianhua; Tian, Xinpeng; Hua, Yan; Ju, Jianhua

doi:10.1021/np300554f

Cited by 84 publications

(76 citation statements)

References 17 publications

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“…Interestingly, marthiapeptide is structurally similar to YM-216391 yet its BGC remains unknown, despite the availability of the whole genome sequence of the producing organism, Marinactinospora thermotolerans . 619 …”

Section: Miscellaneous Azol(in)e-containing Rippsmentioning

confidence: 99%

YcaO-Dependent Posttranslational Amide Activation: Biosynthesis, Structure, and Function

et al. 2017

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With advances in sequencing technology, uncharacterized proteins and domains of unknown function (DUFs) are rapidly accumulating in sequence databases and offer an opportunity to discover new protein chemistry and reaction mechanisms. The focus of this review, the formerly enigmatic YcaO superfamily (DUF181), has been found to catalyze a unique phosphorylation of a ribosomal peptide backbone amide upon attack by different nucleophiles. Established nucleophiles are the side chains of Cys, Ser, and Thr which gives rise to azoline/azole biosynthesis in ribosomally synthesized and posttranslationally modified peptide (RiPP) natural products. However, much remains unknown about the potential for YcaO proteins to collaborate with other nucleophiles. Recent work suggests potential in forming thioamides, macroamidines, and possibly additional post-translational modifications. This review covers all knowledge through mid-2016 regarding the biosynthetic gene clusters (BGCs), natural products, functions, mechanisms, and applications of YcaO proteins and outlines likely future research directions for this protein superfamily.

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Section: Miscellaneous Azol(in)e-containing Rippsmentioning

confidence: 99%

YcaO-Dependent Posttranslational Amide Activation: Biosynthesis, Structure, and Function

et al. 2017

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“…[53]; three new halogenated sesquiterpenes ( 40 – 42 ), isolated from the Chinese marine red alga Laurencia okamurai [54]; a new spirotetronate antibiotic, lobophorin H ( 43 ) from a South China Sea- Streptomyces sp. 12A35 [55]; a new cyclopeptide marthiapeptide A ( 44 ), isolated from the South China Sea-derived bacterium Marinactinospora thermotolerans [56]; two known napyradiomycin A1 ( 45 ) and napyradiomycin B3 ( 46 ) from a Chinese marine-derived Streptomyces sp. strain SCSIO [57,58]; two new hydroanthraquinone analogues 4a- epi -9α-methoxydihydrodeoxybostrycin ( 47 ) and 10-deoxy-bostrycin ( 48 ), isolated from a South China Sea marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone [59]; a novel cyclic peptide ohmyungsamycin A ( 49 ) from a Korean Streptomyces sp.…”

Section: Marine Compounds With Antibacterial Antifungal Antiprotmentioning

confidence: 99%

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

et al. 2017

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The peer-reviewed marine pharmacology literature from 2012 to 2013 was systematically reviewed, consistent with the 1998–2011 reviews of this series. Marine pharmacology research from 2012 to 2013, conducted by scientists from 42 countries in addition to the United States, reported findings on the preclinical pharmacology of 257 marine compounds. The preclinical pharmacology of compounds isolated from marine organisms revealed antibacterial, antifungal, antiprotozoal, antituberculosis, antiviral and anthelmitic pharmacological activities for 113 marine natural products. In addition, 75 marine compounds were reported to have antidiabetic and anti-inflammatory activities and affect the immune and nervous system. Finally, 69 marine compounds were shown to display miscellaneous mechanisms of action which could contribute to novel pharmacological classes. Thus, in 2012–2013, the preclinical marine natural product pharmacology pipeline provided novel pharmacology and lead compounds to the clinical marine pharmaceutical pipeline, and contributed significantly to potentially novel therapeutic approaches to several global disease categories.

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“…A number of structurally unique natural products with antitumor [3,4], antiinfective [5], and antimalarial bioactivities [6], have been discovered from marine-derived actinomycetes. Our recent efforts on marine-derived actinomycetes also led to the isolation of structurally diverse novel natural products with antibacterial, antitumor, and antimalarial bioactivities [7,8,9,10,11,12,13,14,15,16,17]. …”

Section: Introductionmentioning

confidence: 99%

Antibacterial and Cytotoxic New Napyradiomycins from the Marine-Derived Streptomyces sp. SCSIO 10428

et al. 2013

Marine Drugs

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Three new napyradiomycins (1–3) were isolated from the culture broth of a marine-derived actinomycete strain SCSIO 10428, together with six known related analogues napyradiomycin A1 (4), 18-oxonapyradiomycin A1 (5), napyradiomycin B1 (6), napyradiomycin B3 (7), naphthomevalin (8), and napyradiomycin SR (9). The strain SCSIO 10428 was identified as a Streptomyces species by the sequence analysis of its 16S rRNA gene. The structures of new compounds 1–3, designated 4-dehydro-4a-dechloronapyradiomycin A1 (1), 3-dechloro-3-bromonapyradiomycin A1 (2), and 3-chloro-6,8-dihydroxy-8-α-lapachone (3), respectively, were elucidated by comparing their 1D and 2D NMR spectroscopic data with known congeners. None of the napyradiomycins 1–9 showed antioxidative activities. Napyradiomycins 1–8 displayed antibacterial activities against three Gram-positive bacteria Staphylococcus and Bacillus strains with MIC values ranging from 0.25 to 32 μg mL−1, with the exception that compound 3 had a MIC value of above 128 μg mL−1 against Staphylococcus aureus ATCC 29213. Napyradiomycins 2, 4, 6, and 7 exhibited moderate cytotoxicities against four human cancer cell lines SF-268, MCF-7, NCI-H460, and HepG-2 with IC50 values below 20 μM, while the IC50 values for other five napyradiomycins 1, 3, 5, 8 and 9 were above 20 μM.

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Marthiapeptide A, an Anti-infective and Cytotoxic Polythiazole Cyclopeptide from a 60 L Scale Fermentation of the Deep Sea-Derived Marinactinospora thermotolerans SCSIO 00652

Cited by 84 publications

References 17 publications

YcaO-Dependent Posttranslational Amide Activation: Biosynthesis, Structure, and Function

YcaO-Dependent Posttranslational Amide Activation: Biosynthesis, Structure, and Function

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

Antibacterial and Cytotoxic New Napyradiomycins from the Marine-Derived Streptomyces sp. SCSIO 10428

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