Total Synthesis and Anti-Inflammatory Activity of Velutone F

Li, Ying; Wu, Min; Dong, Hanqing; Yu, Pei; Lu, Lan; Du, Weihong; Sheng-hua, Cao

doi:10.1177/1934578x221076653

Cited by 3 publications

(2 citation statements)

References 17 publications

(24 reference statements)

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“…The known compounds ( 3 – 6 ) were identified on the basis of a detailed spectroscopic interpretation in comparison to the reported data in the references, to be Quercetin ( 3 ) [ 22 ], Myricetrin ( 4 ) [ 23 ], Quercitrin ( 5 ) [ 24 ], and Tamarixetin 3-O-rhamnoside ( 6 ) [ 25 ] ( Figure 1 ). Their 1 H-NMR (400 MHz) and 13 C-NMR (100 MHz) data were in the supporting information (Tables S4 and S5) .…”

Section: Resultsmentioning

confidence: 99%

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

et al. 2022

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Two new lactones, named Ardisicreolides A–B (1–2), together with four known flavonoids, Quercetin (3), Myricetrin (4), Quercitrin (5), Tamarixetin 3-O-rhamnoside (6), were isolated from the ethyl acetate portion of 70% ethanol extracts of dried leaves from Ardisia crenata Sims. These compounds were identified from Ardisia crenata Sims for the first time. The structures of 1–6 were elucidated according to 1D and 2D-NMR methods and together with the published literature. All of the isolated compounds were evaluated for in vitro anti-microbial effect against Escherichia coli, Pseudomonas aeuroginosa, Enterococcus faecalis, Proteus vulgaris, Staphylococcus aureus, and Bacillus subtilis. In addition, compounds 1–2 were assessed for anti-inflammatory activity by acting on LPS-induced RAW 264.7 macrophage cells in vitro. The results showed that only compound 2 exhibited moderate antibacterial activity on Bacillus subtilis. Moreover, compounds 1 and 2 were found to significantly inhibit the production of nitric oxide (NO) and reduce the release of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), interleukin-4 (IL-4), and interleukin-10 (IL-10) in LPS-induced RAW 264.7 macrophage cells. The present data suggest that lactones from the leaves of A. crenata Sims might be used as a potential source of natural anti-inflammatory agents.

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Section: Resultsmentioning

confidence: 99%

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

et al. 2022

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“…As shown in Scheme (Part A), the starting material 2,4,6-trihydroxyacetophenone ( 6 ) was protected by treatment with methoxymethyl bromine (MOMBr) and N,N -diisopropylethylamine (DIPEA) in dry CH 2 Cl 2 to give compound 7 in 84% yield . Then base-catalyzed aldol condensation of 7 with benzaldehyde gave chalcone 8a in 95% yield after a simple purification . Optimization of the oxy-Michael reaction was performed with chalcone 8a using various bases. − After several attempts, sodium acetate (NaOAc) was chosen as the proper base to cyclize chalcone 8a to provide an equilibrium mixture of the cyclized product 9a (67%) and starting material 8a (15%).…”

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confidence: 99%

Total Synthesis and Antibacterial Evaluation of Lupinifolin and Its Natural Analogues

Dong,

Liao,

Long

et al. 2024

J. Nat. Prod.

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In this study, lupinifolin (1) and its natural analogues, mundulin (2), minimiorin (3), khonklonginol H (4), flemichin D (5), and eriosemaone A ( 27), were obtained by chemical synthesis for the first time. Key steps involved an electrocyclization to build the linear pyran rings and a Claisen/ Cope rearrangement to install the 8-prenyl substituents. All compounds were assessed for their in vitro antimicrobial activities against clinically relevant human pathogens, including one Gramnegative bacterial strain (E. coli ATCC 25922) and four Grampositive bacterial strains (S. aureus ATCC 29213, E. faecalis ATCC 29212, MRSA21-5, and VRE ATCC 51299). The result indicated that eriosemaone A ( 27) was the most potent one against Grampositive bacteria, with minimum inhibitory concentrations in the range of 0.25−0.5 μg/mL. Mechanistic studies indicated that 27 has good membrane-targeting ability to bacterial inner membranes and can bind to phosphatidylglycerol and cardiolipin in bacterial membranes, thereby disrupting the bacterial cell membranes and causing bacterial death.

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Total Syntheses and Anti-inflammatory Evaluations of Karanjin and its Natural Analogues

Dong

Liu

et al. 2023

LOC

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Karanjin (1) is a natural furanoflavonol derivative isolated from seeds of Pongamia pinnata (L.) Pierre. In this paper, we have accomplished a concise total synthesis of karanjin (1) as well as its natural analogues pongapinnol D (2), 3-hydroxy-6-methoxy-2-phenyl-4H-furo[2,3-h]-1-benzopyran-4-one (3) and 3,6-dimethoxy-2-phenyl-4H-furo[2,3-h]chromen-4-one (4). One-pot aerobic oxidation was the key step to afford the flavonol framework under mild conditions. The anti-inflammatory properties of synthesized 1–4 were determined against NO production in the LPS-stimulated RAW264.7 cells.

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Total Synthesis and Anti-Inflammatory Activity of Velutone F

Cited by 3 publications

References 17 publications

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

Total Synthesis and Antibacterial Evaluation of Lupinifolin and Its Natural Analogues

Total Syntheses and Anti-inflammatory Evaluations of Karanjin and its Natural Analogues

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