Stellerasespenes A‒E: Sesquiterpenoids from Stellera chamaejasme and their anti-neuroinflammatory effects

Cheng, Zhuo-Yang; Zhang, Dingding; Ren, Jing-Xian; Li, Yaling; Yao, Guo-Dong; Song, Shao‐Jiang; Huang, Xiao‐Xiao

doi:10.1016/j.phytochem.2022.113275

Cited by 8 publications

(2 citation statements)

References 37 publications

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“…Novel flavonolignans from the roots of Indigofera stachyodes were characterised by Pan et al 119 Liu et al 120 reported on discovery of anti-MRSA secondary metabolites from a marine-derived fungus Aspergillus fumigatus. Huang et al 121 studied sesquiterpenoids stellerasespenes A-E from Stellera chamaejasme. Zhou et al 122 reported on new carboxamides and a new polyketide from the sponge-derived fungus Arthrinium sp.…”

Section: Nuclear Shielding Calculation In Natural Productsmentioning

confidence: 99%

Theory and computation of nuclear shielding

2023

Nuclear Magnetic Resonance

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This chapter continues earlier reviews of essential works on theoretical issues of nuclear magnetic shieldings published from 1 January to 31 December 2022. As previously, the chapter concentrates on theoretical calculations of nuclear shielding parameters and/or chemical shifts in case of free molecules in the gas phase and solution, and in some cases in the solid state using a periodic formulation. The nuclear shieldings in solution are mainly calculated using inexpensive polarizable continuum model of solvent (PCM). The use of discrete solvent molecules (in particular water and other polar solvents), which is essential for correct description of hydrogen bonding, is often omitted by numerous authors. Most calculations use a relatively simple and fast, but reliable density functional theory (DFT) combined with gauge-including atomic orbital (GIAO) approach. On the other hand, reports on prediction of nuclear magnetic shielding parameters using high level theoretical methods combined with large and flexible basis sets are not so common due to the enormous computational cost. In addition, correction of raw theoretical nuclear magnetic shieldings due to ro-vibration (zero-point vibration correction, ZPVC) and temperature corrections (TC), as well as implicit and explicit solvent effects and relativistic corrections are not often reported.

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Section: Nuclear Shielding Calculation In Natural Productsmentioning

confidence: 99%

Theory and computation of nuclear shielding

2023

Nuclear Magnetic Resonance

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“…Many studies have been conducted on its chemical composition and pharmacological activities in recent decades. A series of compounds have been reported, including highly oxidized daphnane-type diterpenes [12,13], guaiane-type sesquiterpenoids [14][15][16][17][18], unusual C-3/C-3 -biflavanones [19][20][21][22], lignans [14], and coumarins [20]. Some compounds from S. chamaejasme have displayed many different and interesting biological activities in modern pharmacological research.…”

Section: Introductionmentioning

confidence: 99%

Terpenoids from the Roots of Stellera chamaejasme (L.) and Their Bioactivities

Wu,

Ye,

Liao

et al. 2023

Molecules

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An undescribed diterpene, stellerterpenoid A (1), and two undescribed sesquiterpenoids, stellerterpenoids B and C (2–3), together with six known compounds, prostratin (4) stelleraguaianone B (5), chamaejasnoid A (6), auranticanol L (7), wikstronone C (8), and oleodaphnone (9), were isolated from the roots of Stellera chamaejasme L. Their structures were elucidated by extensive spectroscopic data (1D, 2D NMR, IR, UV, and HR-ESI-MS). The absolute configuration of 1–3 was elucidated based on ECD calculation. Among them, stellerterpenoid A was a rare 13, 14-seco nortigliane diterpenoid and stellerterpenoid B was a guaiacane-type sesquiterpenoid with an unusual 1, 2-diketone moiety. The known stelleraguaianone B (5) exhibited moderate activity for suppressing NO production in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages cells with an IC50 value of 24.76 ± 0.4 μM. None of the compounds showed anti-influenza virus or anti-tumor activity in vitro.

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Guaiane-type sesquiterpenoids with various ring skeletons from Daphne bholua uncovered by molecular networking and structural revisions of previously reported analogues

Dong

Duan

et al. 2022

Bioorganic Chemistry

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Stellerasespenes A‒E: Sesquiterpenoids from Stellera chamaejasme and their anti-neuroinflammatory effects

Cited by 8 publications

References 37 publications

Theory and computation of nuclear shielding

Theory and computation of nuclear shielding

Terpenoids from the Roots of Stellera chamaejasme (L.) and Their Bioactivities

Guaiane-type sesquiterpenoids with various ring skeletons from Daphne bholua uncovered by molecular networking and structural revisions of previously reported analogues

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