2016
DOI: 10.1038/ja.2016.122
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New isofuranonaphthoquinones and isoindolequinones from Streptomyces sp. CB01883

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Cited by 9 publications
(5 citation statements)
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“…The 1 H– 1 H COSY and HSQC spectra of 8 (Table ) revealed three main spin systems as follows, namely, between two downfield aromatic protons at δ H 8.14 (H-1) and δ H 8.28 (H-6); between two aliphatic methylene groups at δ H 2.65 (dd, J = 6.8, 8.6 Hz, H 2 -1′) and at δ H 2.20 (t, J = 7.7 Hz, H 2 -2′); from an olefinic proton at δ H 5.27 (dd, J = 1.3, 7.1 Hz, H-4′) showing vicinal and allylic coupling to a methylene group at δ H 2.97 (d, J = 7.1 Hz, H 2 -5′) and a methyl peak at δ H 1.72 (d, J = 1.3 Hz, H 3 -7′), respectively. The HMBC spectrum of 8 showed key correlations (Figure ) from the two downfield protons at H-1 and H-6 to two carbonyl carbon atoms at δ C 182.8 (C-2) and δ C 177.7 (C-5) indicating the chemical structure of 8 (Figure ) to be containing an isobenzofuran-2,5-quinone moiety similar to the previously reported metabolites along with having an aliphatic side chain ending with a free carboxylic acid as in hericioic acids E–G ( 5 – 7 ). Further proofs for the position of the side chain were provided by HMBC spectrum that revealed key correlations from H 2 -1′ to C-2, C-3 (δ C 127.0) and C-4 (δ C 159.8) indicating its presence as a side chain at C-3.…”
Section: Resultssupporting
confidence: 70%
See 1 more Smart Citation
“…The 1 H– 1 H COSY and HSQC spectra of 8 (Table ) revealed three main spin systems as follows, namely, between two downfield aromatic protons at δ H 8.14 (H-1) and δ H 8.28 (H-6); between two aliphatic methylene groups at δ H 2.65 (dd, J = 6.8, 8.6 Hz, H 2 -1′) and at δ H 2.20 (t, J = 7.7 Hz, H 2 -2′); from an olefinic proton at δ H 5.27 (dd, J = 1.3, 7.1 Hz, H-4′) showing vicinal and allylic coupling to a methylene group at δ H 2.97 (d, J = 7.1 Hz, H 2 -5′) and a methyl peak at δ H 1.72 (d, J = 1.3 Hz, H 3 -7′), respectively. The HMBC spectrum of 8 showed key correlations (Figure ) from the two downfield protons at H-1 and H-6 to two carbonyl carbon atoms at δ C 182.8 (C-2) and δ C 177.7 (C-5) indicating the chemical structure of 8 (Figure ) to be containing an isobenzofuran-2,5-quinone moiety similar to the previously reported metabolites along with having an aliphatic side chain ending with a free carboxylic acid as in hericioic acids E–G ( 5 – 7 ). Further proofs for the position of the side chain were provided by HMBC spectrum that revealed key correlations from H 2 -1′ to C-2, C-3 (δ C 127.0) and C-4 (δ C 159.8) indicating its presence as a side chain at C-3.…”
Section: Resultssupporting
confidence: 70%
“…Compound 8 was obtained as an off-white amorphous solid with a characteristic UV spectrum revealing absorption peaks (λ max ) at 201, 249 and 348 nm. The molecular formula of 8 was determined to be C 15 (Figure 1) to be containing an isobenzofuran-2,5-quinone moiety similar to the previously reported metabolites 24 along with having an aliphatic side chain ending with a free carboxylic acid as in hericioic acids E−G (5−7). Further proofs for the position of the side chain were provided by HMBC spectrum that revealed key correlations from H 2 -1′ to C-2, C-3 (δ C 127.0) and C-4 (δ C 159.8) indicating its presence as a side chain at C-3.…”
Section: Journal Ofsupporting
confidence: 60%
“…Natural products have an indisputable track record in drug discovery and remain a rich source of new drug leads and small-molecule probes . Biased on natural products of Actinomycetales origin, the Natural Products Library Initiative at The Scripps Research Institute (TSRI) aims to construct a library that occupies unique chemical space and complements the small-molecule collection at TSRI. Also, natural products of bacterial origin are advantageous since the resupply of enough materials for follow-up studies will be guaranteed by large-scale fermentation once the interesting entities are identified. Three types of collections, including (i) crude extracts, (ii) medium-pressure liquid chromatography (MPLC)-generated fractions, and (iii) structurally assigned pure natural products, constitute the current natural products library (NPL) at TSRI.…”
mentioning
confidence: 99%
“…The presence of a furo-naphthoquinone substructure in several bioactive natural products isolated from terrestrial and marine organisms, along with the potential biological activity of the secondary metabolites obtained from the Amycolatopsis genus, prompted us to screen the bioactive potentials of compounds 1 – 4 .…”
Section: Resultsmentioning
confidence: 99%