Nitric oxide inhibitors with a spiro diterpenoid skeleton from Scutellaria formosana : Structures, NO inhibitory effects, and interactions with iNOS

Wang, Peixia; Yang, Xueyuan; Liu, Feng; Liang, Yue; Su, Guochen; Tuerhong, Muhetaer; Jin, Da Qing; Xu, Jing; Lee, Dong‐Ho; Ohizumi, Yasushi; Guo, Yuanqiang

doi:10.1016/j.bioorg.2017.10.008

Cited by 19 publications

(11 citation statements)

References 36 publications

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“…Compound 2 was isolated as a yellow oil and had the molecular formula C18H24O8 as determined by the HRESIMS peak at m/z 391.1349 [M + Na] + . The 1 H and 13 C NMR data (Table 1) of 2 revealed structural features closely related to the known simplicilopyrone 5 Compound 2 was isolated as a yellow oil and had the molecular formula C18H24O8 as determined by the HRESIMS peak at m/z 391.1349 [M + Na] + . The 1 H and 13 C NMR data (Table 1) of 2 revealed structural features closely related to the known simplicilopyrone 5 Compound 2 was isolated as a yellow oil and had the molecular formula C 18 H 24 O 8 as determined by the HRESIMS peak at m/z 391.1349 [M + Na] + .…”

Section: Resultsmentioning

confidence: 91%

“…The 1 H and 13 C NMR data (Table 1) of 2 revealed structural features closely related to the known simplicilopyrone 5 Compound 2 was isolated as a yellow oil and had the molecular formula C18H24O8 as determined by the HRESIMS peak at m/z 391.1349 [M + Na] + . The 1 H and 13 C NMR data (Table 1) of 2 revealed structural features closely related to the known simplicilopyrone 5 Compound 2 was isolated as a yellow oil and had the molecular formula C 18 H 24 O 8 as determined by the HRESIMS peak at m/z 391.1349 [M + Na] + . The 1 H and 13 C NMR data (Table 1) of 2 revealed structural features closely related to the known simplicilopyrone 5 [22].…”

Section: Resultsmentioning

confidence: 91%

“…It mostly grows in special areas with humid soil in the shade of forests at an altitude of 450–550 m in southern Hainan [ 11 ]. Previous phytochemical investigations of the plant led to the identification of several neo -clerodane diterpenoids and flavonoids, which revealed in vitro cytotoxicity against various cancer cell lines, anti-inflammatory properties, and inhibitory effects against HIV lytic replication [ 11 , 12 , 13 , 14 ]. However, information on the constituents and bioactivity of the secondary metabolites of endophytic fungus from S. formosa is lacking.…”

Section: Introductionmentioning

confidence: 99%

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Four Undescribed Pyranones from the Scutellaria formosana-Derived Endophytic Fungi Ascomycota sp. FAE17

Yang

Chen

et al. 2023

Molecules

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Four undescribed pyranone derivatives, named ascomycopyrones A–D (1–4), as well as one known analogue simplicilopyrone (5) (this is the first study to report the absolute configuration), were isolated from the endophytic fungus Ascomycota sp. FAE17 derived from the flowers of Scutellaria formosa. The structures of these pyranones were identified by comprehensive spectroscopic and MS analyses, and the absolute configurations were determined by their experimental and quantum chemical electronic circular dichroism (ECD) calculations. All isolated compounds were tested for various bioactivities, including antibacterial, cytotoxic activity, and NO inhibitory activity. Unfortunately, none of the compounds showed significant bioactivities.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Four Undescribed Pyranones from the Scutellaria formosana-Derived Endophytic Fungi Ascomycota sp. FAE17

Yang

Chen

et al. 2023

Molecules

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“…The molecular docking studies were performed as described previously [39]. The three dimensional (3D) crystal structures of iNOS (PDB code: 3E6T) and COX-2 (PDB code: 1PXX) were obtained from the RCSB Protein Data Bank, whose resolution was 2.5 Å.…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Caseahomopene A, a ring-expanded homotriterpenoid from Casearia kurzii showing anti-inflammatory activities in vitro and in vivo

Yang

et al. 2020

Bioorganic Chemistry

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“…Thus, inhibiting the production of too much NO may be an effective strategy for treating inflammation-related diseases. In this study, NO was used as a test indicator to preliminarily evaluate the anti-inflammatory activities of compounds. − …”

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confidence: 99%

Euphnerins A and B, Diterpenoids with a 5/6/6 Rearranged Spirocyclic Carbon Skeleton from the Stems of Euphorbia neriifolia

et al. 2020

J. Nat. Prod.

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Euphnerins A (1) and B (2), two extremely modified diterpenoids possessing an unprecedented 5/6/6 rearranged spirocyclic carbon skeleton, and a biosynthetically related known diterpenoid (3) were purified from the stems of Euphorbia neriifolia. Their structures were identified by NMR experiments and X-ray diffraction analysis, as well as experimental and calculated electronic circular dichroism data comparison. A putative biosynthetic relationship of 1 and 2 with their presumed precursor 3 is proposed. Compound 1 showed NO inhibitory effects in lipopolysaccharide-stimulated BV-2 cells with an IC50 value of 22.4 μM.

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Nitric oxide inhibitors with a spiro diterpenoid skeleton from Scutellaria formosana : Structures, NO inhibitory effects, and interactions with iNOS

Cited by 19 publications

References 36 publications

Four Undescribed Pyranones from the Scutellaria formosana-Derived Endophytic Fungi Ascomycota sp. FAE17

Four Undescribed Pyranones from the Scutellaria formosana-Derived Endophytic Fungi Ascomycota sp. FAE17

Caseahomopene A, a ring-expanded homotriterpenoid from Casearia kurzii showing anti-inflammatory activities in vitro and in vivo

Euphnerins A and B, Diterpenoids with a 5/6/6 Rearranged Spirocyclic Carbon Skeleton from the Stems of Euphorbia neriifolia

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