Three isocoumarins and a benzofuran from the cultured lichen mycobionts of Pyrenula sp.

Takenaka, Yasuhiro; Tanahashi, Takao; Nagakura, Naotaka; Itoh, Atsuko; Hamada, Nobuyuki

doi:10.1016/j.phytochem.2004.09.011

Cited by 26 publications

(8 citation statements)

References 12 publications

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“…The 1 H-NMR data of compound 2 (Table 1) indicated the presence of one methyl group at δ H 2.36 (3H, s, H-1 ) as well as three olefinic methines at δ 1. The aforementioned information indicated that compound 2 could be a gallic acid derivative, which is similar to (E)-5,8-dihydroxy-3-(1-pentenyl)-isocoumarin that has been reported [18].…”

Section: Structure Elucidationsupporting

confidence: 52%

Four New Gallate Derivatives from Wine-Processed Corni Fructus and Their Anti-Inflammatory Activities

Zhang

et al. 2021

Molecules

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Four new gallate derivatives—ornusgallate A, ent-cornusgallate A, cornusgallate B and C (1a, 1b, 2, 3)—were isolated from the wine-processed fruit of Cornus officinalis. Among them, 1a and 1b are new natural compounds with novel skeletons. Their chemical structures were elucidated by comprehensive spectroscopy methods including NMR, IR, HRESIMS, UV, ECD spectra and single-crystal X-ray diffraction analysis. The in vitro anti-inflammatory activities of all compounds were assayed in RAW 264.7 cells by assessing LPS-induced NO production. As the result, all compounds exhibited anti-inflammatory activities at attested concentrations. Among the tested compounds, compound 2 exhibited the strongest anti- inflammatory activity.

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Section: Structure Elucidationsupporting

confidence: 52%

Four New Gallate Derivatives from Wine-Processed Corni Fructus and Their Anti-Inflammatory Activities

Zhang

et al. 2021

Molecules

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“…26,27 Interestingly, the co-occurrence of isocoumarins and benzofurans in the same fungal species has also rarely been reported, only from lichen mycobionts and a Canadian thistle endophytic fungus. 28,29 In this paper, the isocoumarin derivatives with sixmembered lactones and the benzofurans were simultaneously isolated from a marine-derived Penicillium fungus for the first time. All of the isolated isocoumarin derivatives and benzofurans may share a similar biosynthetic pathway from a common open-chain precursor.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Isocoumarin Derivatives and Benzofurans from a Sponge-DerivedPenicilliumsp. Fungus

Shao

et al. 2013

J. Nat. Prod.

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Ten new fungal metabolites, including three hydroisocoumarins, penicimarins A-C (1-3), three isocoumarins, penicimarins D-F (6-8), and four benzofurans, penicifurans A-D (11-14), together with four known isocoumarin derivatives (4, 5, 9, 10), were obtained from the sponge-derived fungus Penicillium sp. MWZ14-4, collected from the South China Sea. Their planar structures and relative configurations were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-4 were assigned by the modified Mosher's method and TDDFT ECD calculations together with comparison of their CD spectra. Compound 1 represents a rare naturally occurring isocoumarin derivative with 4-substitution, but no substituent at the 3-position. These compounds were evaluated for antibacterial activities and cytotoxic activities in vitro. Among them, penicifuran A (11) exhibited inhibitory activity against Staphylococcus albus with an MIC value of 3.13 μM.

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“…Its UV, IR, and 1 H and 13 C NMR (Tables 2 and 3) spectra displayed its structural similarity to 7. However, the 13 From our previous chemical investigations of the cultured mycobionts of the genus Pyrenula, we reported the isolation of xanthone, 11,12 anthraquinone, 12 azaphilone, 12 isocoumarin, 16 benzofuran, 16 and naphthopyrone 17 derivatives. In this study, we examined the cultured mycobiont of a Pyrenula sp.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Polyketides from the Cultured Lichen Mycobiont of a Vietnamese Pyrenula sp.

Takenaka

Hamada

et al. 2014

J. Nat. Prod.

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A spore-derived mycobiont of a crustose Pyrenula sp. lichen collected in Vietnam was cultivated on a malt-yeast extract medium supplemented with 10% sucrose. Chemical investigation of the cultivated colonies led to the isolation of eight new alkylated decalin-type polyketides (1-8) along with three known compounds. The structures of these compounds were elucidated by spectroscopic and chemical means. This is the first instance of this type of polyketide being isolated from a cultured lichen mycobiont. The isolated polyketides 1 and 7 exhibited inhibitory activities against mammalian DNA polymerases α and β with IC50 values ranging from 8.1 to 19.5 μM. Compound 1 showed cytotoxic effects against the HCT116 human colon carcinoma cultured cell line with an IC50 value of 6.4 ± 0.7 μM.

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Three isocoumarins and a benzofuran from the cultured lichen mycobionts of Pyrenula sp.

Cited by 26 publications

References 12 publications

Four New Gallate Derivatives from Wine-Processed Corni Fructus and Their Anti-Inflammatory Activities

Four New Gallate Derivatives from Wine-Processed Corni Fructus and Their Anti-Inflammatory Activities

Isocoumarin Derivatives and Benzofurans from a Sponge-DerivedPenicilliumsp. Fungus

Polyketides from the Cultured Lichen Mycobiont of a Vietnamese Pyrenula sp.

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