Dihydro-β-agarofuran sesquiterpenoid derivatives with anti-inflammatory activity from the leaves of Tripterygium wilfordii

He, Qiwei; Zhou, Le; Lu, Li-Wei; Zhao, Feng; Huang, Xiao‐Xiao; Lin, Bin; Song, Shao‐Jiang

doi:10.1016/j.bioorg.2019.103288

Cited by 13 publications

(7 citation statements)

References 28 publications

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“…Compound 1 exhibited a negative Cotton effect at 295 nm (Figure 6), suggesting the absolute configuration of 5 S according to the octant rule of saturated cyclohexanone. [ 19 ] Compound 1 was given the trivial name frititorine D.…”

Section: Resultsmentioning

confidence: 99%

Isosteroidal Alkaloids from Fritillaria verticillata Willd. and Their NMR Spectroscopic Characteristics

et al. 2022

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Chemical investigation of Fritillaria verticillata Willd. led to the isolation of eight novel isosteroidal alkaloids (1-4, 6, 9-11) and four known alkaloids (5, 7-8, 12), including three unprecedented cis-fused D/E (13α, 17α) cevanine alkaloids (1-3), one rarely cis-fused E/F (22α) cevanine alkaloid (6), and one uncommon 5β-jervine-type isosteroidal alkaloid featuring a cis-fused A/B ring moiety (11). In order to establish the structures of 1, the calculated NMR with DP4+ evaluation was applied from the plausible structure candidates. The characteristic proton signals for distinguishing D/E conjunction of cevanine alkaloids were summarized. In addition, some proton and carbon signals α to nitrogen in 6 and 7 are unobservable due to the 14 N nuclear quadrupolar relaxation, based on the NMR experiments in different solvents, calculated NMR method and X-ray technology, their structures were determined. The NMR characteristics of cevanine alkaloids to distinguish orientation of long-pair on nitrogen atom with β-hydroxyl at C-20 were also concluded. The anti-inflammatory effects of compounds 1 and 4 were evaluated in LPS-activated RAW 264.7 macrophages. Compound 4 decreased LPS-induced releases of IL-1β and IL-17α in RAW264.7 cells in a dose-dependent manner. Further mechanistic study revealed that 4 suppressed the phosphorylation of IκBα and p65 subunit to regulate the NF-κB signaling pathway.

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Section: Resultsmentioning

confidence: 99%

Isosteroidal Alkaloids from Fritillaria verticillata Willd. and Their NMR Spectroscopic Characteristics

et al. 2022

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“…Twelve known compounds were identified as triptersinoid D ( 18 ), 1α,6β,8α-triacetyloxy-9α-benzoyloxydihydro-β-agarofuran ( 19 ), (1 R ,2 R ,4 R ,5 S ,6 R ,7 R ,8 S ,9 R ,10 S )-1,2,6,8-tetraacetyloxy-9-benzoyloxydihydro-β-agarofuran ( 20 ), 1α,2β,8β-triacetyloxy-6β-cinnamoyloxy-9β-benzoyloxydihydro-β-agarofuran ( 21 ), 1α,2β,6β,8α-tetraacetyloxy-9α-benzoyloxydihydro-β-agarofuran ( 22 ), (1 R ,2 S ,5 S ,6 R ,7 R ,8 R ,9 S )-1,6,8-triacetyloxy-2-cinnamoyloxy-9-benzoyloxydihydro-β-agarofuran ( 23 ), 1β,2α,8β-triacetyloxy-6β-nicotinoyloxy-9β-benzoyloxydihydro-β-agarofuran ( 24 ), 1α,6β-diacetyloxy-9β-benzoyloxydihydro-β-agarofuran ( 25 ), 1α-acetyloxy-6β,9β-dibenzoyloxydihydro-β-agarofuran ( 26 ), 1α-acetyloxy-6β-cinnamoyloxy-9β-benzoyloxydihydro-β-agarofuran ( 27 ), 1α,2β-diacetyloxy-6β-cinnamoyloxy-9β-benzoyloxydihydro-β-agarofuran ( 28 ), and 1α,6β,8α-triacetyloxy-9β-benzoyloxy-β-dihydroagarofuran ( 29 ) by comparison of their NMR data with those reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Dihydro-β-agarofuran-Type Sesquiterpenoids from the Seeds of Celastrus virens and Their Multidrug Resistance Reversal Activity against the KB/VCR Cell Line

Tang

Zuo

et al. 2021

J. Nat. Prod.

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Twenty-nine dihydro-β-agarofuran-type sesquiterpenoids, including 17 new and 12 known compounds, were obtained from the seeds of Celastrus virens. The structures of the new isolates were characterized by spectroscopic methods and Xray diffraction analysis. Among these, 20 sesquiterpenoids were evaluated for their multidrug resistance (MDR) reversal activity against the KB/VCR cell line. As a result, compounds 6 and 8 were found to exhibit MDR-reversal activity of more than 10-fold at a concentration of 2 μM, and the reversal fold (RF) ratios of compounds 19, 21, and 24 were >97.9 at a 20 μM nontoxic concentration level.E ven though it is one of the prime treatments for cancer, chemotherapy may not always be successful, due to the emergence of multidrug resistance (MDR), which may impede the effectiveness of the cancer treatment administered. MDR manifests as a cross-tolerance of multiple anticancer drugs irrespective of structure and activity. Extensive research on MDR has shown that overexpression of P-glycoprotein (P-gp) is the most crucial cause of reducing drug accumulation and increasing drug resistance in tumor cells. 1−3 A number of important anticancer drugs, such as paclitaxel (TAX), doxorubicin (DOX), and vincristine (VCR), are known substrates of P-gp. 4−6 P-gp inhibitors have been divided into four generations based on potency, selectivity, and drug−drug interaction potential. 7 The first generation P-gp inhibitors included verapamil (VRP) and cyclosporin A, 8,9 while devilapamil and valspodar belong to the second generation, 10,11 and the third generation includes tariquidar, zosuquidar, and various tyrosine kinase inhibitors. 12−16 Unfortunately, due to drug−drug interactions and unacceptable toxic and side effects, only a few of these P-gp inhibitors, such as Nuedexta, Restasis, Oraxol, and Kalydeco, have been approved for marketing. 17−19 The exploitation of the fourthgeneration P-gp inhibitors includes the screening of natural products and their purified bioactive constituents. 20,21 Dihydro-β-agarofuran sesquiterpenoids are characteristic metabolites of the family Celastraceae, 22 which exhibit a broad spectrum of biological activities, including cytotoxicity, 23 insecticidal, 24 antitumor-promoting, 25 MDR-reverting, 26 antitubercular, 27 neuroprotective, 28 immunosuppressive, 29 anti-HIV, 30 anti-inflammatory, 31 and lifespan-extending effects. 32 Celastrus virens (Wang et Tang) C. Y. Chent et T. C. Kao (Celastraceae), an endemic plant of mainland China, is distributed mainly in Yunnan, Guangdong, and several other provinces. 33 To date, preliminary chemical investigations of the leaves and root bark of C. virens have led to the identification of several triterpenoid, steroid, and fatty acid constituents. 34 Herein, we report the isolation and structural characterization of 17 new and 12 known dihydro-β-agarofuran-type sesquiterpenoids from the seeds of C. virens, as well as the bioassay results of 20 of the more abundant isolates obtained for their MDR-reverting activity against the KB/V...

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“…Quantum calculations based on density functional theory (DFT) were carried out to optimize the atomic structures at the B3LYP/6‐31G(d) level with the Gaussian 09 package. The overall theoretical ECD curves were simulated using SpecDis 1.51 software based on the Boltzmann weighting of each conformer [22] …”

Section: Methodsmentioning

confidence: 99%

“…Besides, we evaluated their (1a/1b -3a/3b) effect on NO production using lipopolysaccharide (LPS)-stimulated BV2 cells. [20][21][22][23][24][25]…”

Section: Introductionmentioning

confidence: 99%

Two New Enantiomers of Phenylethanoid and Their Anti‐Inflammatory Activities

Jia

Yang

et al. 2023

Chemistry & Biodiversity

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In this phytochemical investigation, two pairs of new phenylethanoid derivative enantiomers (1a/1b and 2a/ 2b), a new phenylethanoid derivative 3b, and seven known compounds (3a, 4-9) were isolated from the leaves of Picrasma quassioides. Spectroscopic techniques were used for the elucidation of their chemical structures, and the absolute configurations were determined by a comparison between the experimental and calculated ECD data, as well as the application of Snatzke's method. Compounds (1a/1b -3a/3b) were measured for their production of NO levels in LPS-induced BV-2 microglial cells. The results showed that all compounds exhibited potential inhibitory effects, and compound 1a showed stronger activity than the positive control.

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Dihydro-β-agarofuran sesquiterpenoid derivatives with anti-inflammatory activity from the leaves of Tripterygium wilfordii

Cited by 13 publications

References 28 publications

Isosteroidal Alkaloids from Fritillaria verticillata Willd. and Their NMR Spectroscopic Characteristics

Isosteroidal Alkaloids from Fritillaria verticillata Willd. and Their NMR Spectroscopic Characteristics

Dihydro-β-agarofuran-Type Sesquiterpenoids from the Seeds of Celastrus virens and Their Multidrug Resistance Reversal Activity against the KB/VCR Cell Line

Two New Enantiomers of Phenylethanoid and Their Anti‐Inflammatory Activities

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