Studies on Terpenoids Produced by Actinomycetes

Motohashi, Ken; Irie, Kiyofumi; Toda, Takashi; Matsuo, Yoshihide; Kasai, Hiroaki; Sue, Masayuki; Furihata, Kazuo; Seto, Haruo

doi:10.1038/ja.2008.113

Cited by 35 publications

(24 citation statements)

References 20 publications

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“…Napyradiomycins were first isolated from terrestrial microorganisms from 1986 [18,28], and then were discovered from the marine-derived strains from the last decade [22,23]. Up to date, about 43 derivatives of napyradiomycins have been discovered [18,19,20,21,22,23,24,25,29,30,31,32,33]. Structurally, napyradiomycins consist of a semi-napthoquinone core, a prenyl unit attached at C-4a that is cyclized to form a tetrahydropyran ring in most cases, and a monoterpenoid substituent attached at C-10a.…”

Section: Resultsmentioning

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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Section: Resultsmentioning

confidence: 99%

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

et al. 2013

Marine Drugs

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“…Biosynthesis of terpanoids from the precursor Farnesyl pyrophosphate correlated strongly, not only with the relative abundances of Crenarchaeota and Chlamydiae , but also with the relative change in concentration of TOC. Terpenoids are a functionally diverse set of molecules whose synthesis by marine bacteria has been previously reported [29,30]. …”

Section: Resultsmentioning

confidence: 99%

Predicted Relative Metabolomic Turnover (PRMT): determining metabolic turnover from a coastal marine metagenomic dataset

Larsen

Collart

Field

et al. 2011

Microb Informatics Exp

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BackgroundThe world's oceans are home to a diverse array of microbial life whose metabolic activity helps to drive the earth's biogeochemical cycles. Metagenomic analysis has revolutionized our access to these communities, providing a system-scale perspective of microbial community interactions. However, while metagenome sequencing can provide useful estimates of the relative change in abundance of specific genes and taxa between environments or over time, this does not investigate the relative changes in the production or consumption of different metabolites.ResultsWe propose a methodology, Predicted Relative Metabolic Turnover (PRMT) that defines and enables exploration of metabolite-space inferred from the metagenome. Our analysis of metagenomic data from a time-series study in the Western English Channel demonstrated considerable correlations between predicted relative metabolic turnover and seasonal changes in abundance of measured environmental parameters as well as with observed seasonal changes in bacterial population structure.ConclusionsThe PRMT method was successfully applied to metagenomic data to explore the Western English Channel microbial metabalome to generate specific, biologically testable hypotheses. Generated hypotheses linked organic phosphate utilization to Gammaproteobactaria, Plantcomycetes, and Betaproteobacteria, chitin degradation to Actinomycetes, and potential small molecule biosynthesis pathways for Lentisphaerae, Chlamydiae, and Crenarchaeota. The PRMT method can be applied as a general tool for the analysis of additional metagenomic or transcriptomic datasets.

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“…This class of secondary metabolites consists of a naphthoquinone core, a prenyl unit attached at C-4a, a monoterpenoid substituent at C-10a, and some congeners have a methyl group at C-7 [1,4,5,6]. At present, nearly 47 different NPDs have been described [1,2,4,5,6,7,8,9,10,11,12]. Compounds belonging to this structural class possess significant antibacterial activity against pathogenic bacterial strains such as methicillin-resistant Staphylococcus aureus (MRSA) and inhibit the growth of several tumor cell lines [13,14,15].…”

Section: Introductionmentioning

confidence: 99%

MDN-0170, a New Napyradiomycin from Streptomyces sp. Strain CA-271078

et al. 2016

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A new napyradiomycin, MDN-0170 (1), was isolated from the culture broth of the marine-derived actinomycete strain CA-271078, together with three known related compounds identified as 4-dehydro-4a-dechloronapyradiomycin A1 (2), napyradiomycin A1 (3) and 3-chloro-6,8-dihydroxy-8-α-lapachone (4). The structure of the new compound was determined using a combination of spectroscopic techniques, including 1D and 2D NMR and electrospray-time of flight mass spectrometry (ESI-TOF MS). The relative configuration of compound 1, which contains two independent stereoclusters, has been established by molecular modelling in combination with nOe and coupling constant analyses. Biosynthetic arguments also allowed us to propose its absolute stereochemistry. The antimicrobial properties of the compounds isolated were evaluated against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, Aspergillus fumigatus, and Candida albicans. The potent bioactivity previously reported for compounds 2 and 3 against methicillin-sensitive S. aureus has been extended to methicillin-resistant strains in this report.

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Studies on Terpenoids Produced by Actinomycetes

Abstract: As a result of screening for terpenoids produced by marine-derived Streptomyces sp. MS239, two new terpenoids named 5-dimethylallylindole-3-carboxylic acid and A80915G-8Љ-acid were isolated and their structures were determined mainly by NMR analyses.

Cited by 35 publications

References 20 publications

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

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

Predicted Relative Metabolomic Turnover (PRMT): determining metabolic turnover from a coastal marine metagenomic dataset

MDN-0170, a New Napyradiomycin from Streptomyces sp. Strain CA-271078

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