Synthesis and Structural Characterization of Natural Benzofuranoids

Kuramochi, Kouji; Tsubaki, Kazunori

doi:10.1021/np5010483

Cited by 11 publications

(10 citation statements)

References 25 publications

(72 reference statements)

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“…Asperisocoumarin C ( 3 ) and D ( 4 ) had the same structure as ( R )-2-isopropyl-7-methyl-6,7-dihydro-9 H -furo[3,2- h ]isochromen-9-one and ( R )-7-methyl-2-(propan-2-ylidene)-6,7-dihydro-9 H -furo[3,2- h ]isochromene-3,9-(2 H )-dione, respectively. Both have been synthesized as intermediates during synthesis and structural characterization of natural benzofuranoids [9]. Asperisocoumarin E ( 5 ) containing an isopentenyl substituent with two adjacent carbonyl groups seems to be rare in natural isocoumarin derivatives and asperisocoumarin F ( 6 ) presents as a scaffold with an ether dimer of isocoumarin.…”

Section: Resultsmentioning

confidence: 99%

“…The linear furo[2,3- g ]isocoumarins are relatively common in nature and coriandrin [3–4], dihydrocoriandrin [3–4], coriandrone C [5], and coriandrone E [5] are a few examples. However, an angular-type furo[3,2- h ]isocoumarin has up to date only been once reported from a natural source: Coriandrone A isolated from the aerial parts of Coriandrum sativum [6] and other furo[3,2- h ]isocoumarins have been reported as synthetic products [7–9]. …”

Section: Introductionmentioning

confidence: 99%

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New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

Xiao¹,

Chen²,

Cai³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe chemical investigation of the mangrove endophytic fungus Aspergillus sp. 085242 afforded eight isocoumarin derivatives 1–8 and one isoquinoline 9. Asperisocoumarins A and B (1 and 2) were new furoisocoumarins, and asperisocoumarins E and F (5 and 6) were new isocoumarins. Their structures were established by analysis of their spectroscopic data and the absolute configuration of compound 2 was unambiguously determined by X-ray structure analysis and ECD calculation. Moreover, the absolute configurations of compounds 3–5 were assigned by comparison of their ECD spectra with isocoumarins described in the literature. Asperisocoumarins C and D (3 and 4) were fully characterized spectroscopically and isolated from a natural source for the first time. Asperisocoumarins A–D (1–4) related to the class of furo[3,2-h]isocoumarins are rarely occurring in natural sources. Compounds 2, 5, and 6 showed moderate α-glucosidase inhibitory activity with IC50 of 87.8, 52.3, and 95.6 μM, respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC50 values of 125 and 138 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

Xiao¹,

Chen²,

Cai³

et al. 2016

Beilstein J. Org. Chem.

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“…ZJ-68 was purified by repeatedly various chromatography to yield five new ( 1 – 3 , 6 , and 7 ) and nine known compounds ( 4 , 5 , and 8 − 14 ). The known compounds were identical to (−)-penicisochroman A ( 4 ) [13,14,15], (+)-penicisochroman A ( 5 ) [13,14,15], 2-(hydroxymethyl)-3-propylphenol ( 8 ) [16], peniciphenol ( 9 ) [13], penicibenzoxepinol ( 10 ) [17], (−)-brassicadiol ( 11 ) [14,18], (+)-pseudodeflectusin ( 12 ) [14,19], (−)-penicisochroman B ( 13 ) [13,14], and ustusorane A ( 14 ) [14,20] by the comparison of their spectral data (NMR and MS) as well as specific rotation data with those reported.…”

Section: Resultsmentioning

confidence: 99%

New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68

et al. 2019

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Three new benzofuranoids, asperfuranoids A–C (1–3), two new phenylpropanoid derivatives (6 and 7), and nine known analogues (4, 5, and 8–14) were isolated from the liquid substrate fermentation cultures of the mangrove endopytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were determined by extensive spectroscopic data interpretation. The absolute configurations of 1–3 were assigned via the combination of Mosher’s method, and experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 were a pair of enantiomers and their absolute configurations were established for the first time on the basis of their ECD spectra aided with ECD calculations. All isolated compounds (1–14) were evaluated for their enzyme inhibitory activity against α-glucosidase and antibacterial activities against four pathogenic bacteria (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa). Among them, compound 6 exhibited potent inhibitory activity against α-glucosidase in a standard in vitro assay, with an IC50 value of 12.4 μM, while compounds 8 and 11 showed activities against S. aureus, E. coli, and B. subtilis, with MIC values in the range of 4.15 to 12.5 μg/mL.

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“…(−)-Brassicadiol (37) exhibited cytotoxicity against both cancerous and non-cancerous (Vero) cells, with IC 50 values ranging from 66.3 to 113.3 µM [31]. The synthesis of (−)-brassicadiol (37) was also described [32]. One study showed that daldinin C (38) was firstly isolated from cultures of the ascomycete Daldinia concentrica [33].…”

Section: Cold Seeps 21 Marine Animalsmentioning

confidence: 99%

Deep-Sea Natural Products from Extreme Environments: Cold Seeps and Hydrothermal Vents

et al. 2022

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The deep sea has been proven to be a great treasure for structurally unique and biologically active natural products in the last two decades. Cold seeps and hydrothermal vents, as typical representatives of deep-sea extreme environments, have attracted more and more attention. This review mainly summarizes the natural products of marine animals, marine fungi, and marine bacteria derived from deep-sea cold seeps and hydrothermal vents as well as their biological activities. In general, there were 182 compounds reported, citing 132 references and covering the literature from the first report in 1984 up to March 2022. The sources of the compounds are represented by the genera Aspergillus sp., Penicillium sp., Streptomyces sp., and so on. It is worth mentioning that 90 of the 182 compounds are new and that almost 60% of the reported structures exhibited diverse bioactivities, which became attractive targets for relevant organic synthetic and biosynthetic studies.

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Synthesis and Structural Characterization of Natural Benzofuranoids

Cited by 11 publications

References 25 publications

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68

Deep-Sea Natural Products from Extreme Environments: Cold Seeps and Hydrothermal Vents

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