Anti-inflammatory and α-Glucosidase Inhibitory Activities of Labdane and Norlabdane Diterpenoids from the Rhizomes of <i>Amomum villosum</i>

Yin, Hong; Dan, Wenjia; Fan, Bo‐Yi; Guo, Chao; Wu, Kui; Li, Ding; Xian, Kui-Feng; Gao, Jin‐Ming

doi:10.1021/acs.jnatprod.9b00283

Cited by 37 publications

(18 citation statements)

References 34 publications

(68 reference statements)

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“…Inhibitory activity of α-glucosidase was assessed following the methods reported previously, using genistein as the positive control. , …”

Section: Methodsmentioning

confidence: 99%

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Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii

Zhai

Huo

et al. 2020

J. Nat. Prod.

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Phaeosphaeria f uckelii, an endophytic fungus associated with the herbal medicine Phlomis umbrosa, produced four new thiodiketopiperazine alkaloids, phaeosphaones A−D (1−4), featuring an unusual β-(oxy)thiotryptophan motif, along with four known analogues, phaeosphaone E (5), chetoseminudin B (6), polanrazine B (7), and leptosin D (8). Their structures were elucidated by extensive spectroscopic data analysis, and their absolute configurations were determined by single-crystal X-ray diffraction and ECD calculations. Compounds 4, 6, and 8 were found to display mushroom tyrosinase inhibitory activity with IC 50 values of 33.2 ± 0.2, 31.7 ± 0.2, and 28.4 ± 0.2 μM, respectively, more potent than that of the positive control, kojic acid (IC 50 = 40.4 ± 0.1 μM). A molecular-docking study disclosed the π−π stacking interaction between the indole moiety of 8 and the His243 residue of tyrosinase.

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“…Inhibitory activity of α-glucosidase was assessed following the methods reported previously, using genistein as the positive control. , …”

Section: Methodsmentioning

confidence: 99%

“…Inhibitory activity of αglucosidase was assessed following the methods reported previously, using genistein as the positive control. 34,35 Antibacterial Assay. Antibacterial test was performed according to the previously published report.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii

Zhai

Huo

et al. 2020

J. Nat. Prod.

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“…The α-glucosidase inhibition test of the compounds was carried out as reported previously. , Briefly, Saccharomyces cerevisiae α-glucosidase was supplied by Sigma (EC 3.2.1.20). A solution of the enzyme in 200 μL of 10 mM phosphate buffer (pH 6.80) was incubated with 12 μL of the compound tested in dimethylsulfoxide at 37 °C for 5 min.…”

Section: Methodsmentioning

confidence: 99%

Microbial Transformations of Two Beyerane-Type Diterpenes by Cunninghamella echinulata

Gao

Wang

et al. 2020

J. Agric. Food Chem.

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Microbial transformations of two tetracyclic beyerane-type diterpenes, ent-16β-oxobeyeran-19-oic acid (1) and its chemical reduction product, ent-16β-hydroxybeyeran-19-oic acid (2), by the filamentous fungus Cunninghamella echinulata ATCC 8688a yielded eight metabolites (3−10). Incubation of the substrate 2 with C. echinulata afforded three new hydroxylated ones (3− 5) along with two known ones (6−7), while incubation of 1 gave three known ones (8−10). The new compounds were characterized by 1D and 2D NMR as well as HRESIMS analysis, and the stereostructures of 3 and 4 were confirmed by X-ray crystallography. The bioreactions were involved not only in stereoselective incorporation of hydroxyl groups at inert positions C-7, -9, -12, and -14 of the two beyerane diterpenes but also in glucosidation at C-19 of 2. This is the first report on the biotransformation of the diterpenes by using C. echinulata. All compounds were assayed for their α-glucosidase inhibitory, neurotrophic, antiinflammatory, and phytotoxic activity, and only in neurotrophic assay compounds, 2 and 9 were found to display nerve growth factor-mediated neurite-outgrowth promoting effects in PC12 cells; the others were inactive.

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“…After 1 hour, it was treated with 1 µg/mL lipopolysaccharides (LPS). 16 Detailed experimental procedures and information could be found in the operating method of Beyotime's Griess solution kits.…”

Section: Nitric Oxide Production Assaymentioning

confidence: 99%

A Novel Pterocarpan Derivative From the Roots of Sophora flavescens

Zhang

Liú

et al. 2020

Natural Product Communications

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Flavescensin A (1), a novel rearrangement derivative of pterocarpan with an unusual spirotetrahydrofuran ring, along with 7 known pterocarpans were isolated from the roots of Sophora flavescens using several different chromatographic separations. The planar structure of 1 was elucidated by their nuclear magnetic resonance spectroscopic and high-resolution electrospray ionization mass spectrometry data, and the absolute configuration of 1 was determined on the basis of electronic circular dichroism data. Putative biosynthetic pathway toward 1 was proposed. In addition, all of the compounds were evaluated for their anti-influenza virus and anti-inflammatory activities.

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Anti-inflammatory and α-Glucosidase Inhibitory Activities of Labdane and Norlabdane Diterpenoids from the Rhizomes of Amomum villosum

Cited by 37 publications

References 34 publications

Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii

Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii

Microbial Transformations of Two Beyerane-Type Diterpenes by Cunninghamella echinulata

A Novel Pterocarpan Derivative From the Roots of Sophora flavescens

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