Structurally Diverse <scp>Matrine‐Based</scp> Alkaloids with Anti‐inflammatory Effects from <i>Sophora alopecuroides</i>

Luo, Dan; Chen, Neng‐Hua; Wang, Wenzhi; Zhang, Jihui; Li, Can‐Jie; Zhuo, Xue‐Fang; Tu, Zhenchao; Wu, Zhong‐Nan; Fan, Chun‐Lin; Zhang, Haipeng; Wang, Guo‐Cai; Zhang, Yubo

doi:10.1002/cjoc.202100526

Cited by 13 publications

(7 citation statements)

References 29 publications

(21 reference statements)

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“…Only V. officinalis and V. bonariensis have some chemical constituents and pharmacological effects research. In previous reports, nuclear magnetic resonance ( Shu et al, 2014 ; Luo et al, 2021 ), HPLC-DAD ( Liu et al, 2012 ), HPLC-MS ( El-Hela et al, 2010 ) and other technologies were used to study the chemical components and content of V. officinalis . In this study, we used UPLC-MS technology to identify the chemical components in V. officinalis extract.…”

Section: Discussionmentioning

confidence: 99%

Integrating transcriptome and chemical analyses to reveal the anti-Alzheimer’s disease components in Verbena officinalis Linn

Peng

et al. 2022

Front. Plant Sci.

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Verbena officinalis Linn. is a kind of traditional Chinese medicine, which has a long history of application and shows good effects on neuroprotection. Therefore, we consider that V. officinalis may be a potential drug for treating Alzheimer’s disease (AD). First, ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) pointed out that the main chemical components in V. officinalis were iridoid glycosides, phenylethanoid glycosides, and flavonoids. These compounds were used for molecular docking and the results showed that these compounds had good anti-AD activity. To explore the biosynthetic pathway of anti-AD components in V. officinalis, UPLC and ultraviolet (UV) spectrophotometry were used for contents determination and the result was leaf > stem > root. At the same time, 92,867 unigenes were annotated in V. officinalis transcriptome; 206, 229, 115 related unigenes were, respectively, annotated in iridoid glycoside, phenylethanoid glycoside, and flavonoid pathway, of which 61, 73, and 35 were differential expression genes. The components had relatively high expression in leaves, which was consistent with the quantitative results. In addition, the tissue distribution particularity of verbenalin may be related to the branching of pathways. Meanwhile transcription factors VoWRKY6 and VoWRKY7 may be involved in the regulation of iridoid glycoside biosynthesis. Further, VoWRKY3, VoWRKY9, and VoWRKY12 may be related to flavonoid biosynthesis. The above research is helpful to explore the biosynthetic pathway of anti-AD components and the regulation mechanism of active components and to further explore the anti-AD effect of V. officinalis.

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Section: Discussionmentioning

confidence: 99%

Integrating transcriptome and chemical analyses to reveal the anti-Alzheimer’s disease components in Verbena officinalis Linn

Peng

et al. 2022

Front. Plant Sci.

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“…The best result was obtained with compound 377 , which showed an inhibition of 96.64%. In the case of the IL-6 factor, the studies reported 40–68% inhibitions. ,,− …”

Section: Compendium Of Biological Activities Reported For Quinolizidi...mentioning

confidence: 99%

Quinolizidine-Type Alkaloids: Chemodiversity, Occurrence, and Bioactivity

2023

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Quinolizidine alkaloids (QAs) are nitrogen-containing compounds produced naturally as specialized metabolites distributed in plants and animals (e.g., frogs, sponges). The present review compiles the available information on the chemical diversity and biological activity of QAs reported during the last three decades. So far, 397 QAs have been isolated, gathering 20 different representative classes, including the most common such as matrine (13.6%), lupanine (9.8%), anagyrine (4.0%), sparteine (5.3%), cytisine (6.5%), tetrahydrocytisine (4.3%), lupinine (12.1%), macrocyclic bisquinolizidine (9.3%), biphenylquinolizidine lactone (7.1%), dimeric (7.1%), and other less known QAs (20.9%), which include several structural patterns of QAs. A detailed survey of the reported information about the bioactivities of these compounds indicated their potential as cytotoxic, antiviral, antimicrobial, insecticidal, anti-inflammatory, antimalarial, and antiacetylcholinesterase compounds, involving favorable putative drug-likeness scores. In this regard, research progress on the structural and biological/pharmacological diversity of QAs requires further studies oriented on expanding the chemical space to find bioactive scaffolds based on QAs for pharmacological and agrochemical applications.

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“…As far as we know, some pro‐inflammatory cytokines, such as TNF‐α, IL‐1β and IL‐17α, play important roles in the pathogenesis of inflammatory diseases. [ 33‐37 ] For example, IL‐1β is produced by activated macrophages as a proprotein, which is an important mediator of the inflammatory response, and is involved in a variety of cellular activities, including cell proliferation, differentiation, and apoptosis. IL‐17α, an important cytokine of T‐helper 17 (TH17) cell subsets, has key roles in extracellular pathogen protection and also stimulates the inflammatory response in autoimmune disorders.…”

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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Structurally Diverse Matrine‐Based Alkaloids with Anti‐inflammatory Effects from Sophora alopecuroides

Cited by 13 publications

References 29 publications

Integrating transcriptome and chemical analyses to reveal the anti-Alzheimer’s disease components in Verbena officinalis Linn

Integrating transcriptome and chemical analyses to reveal the anti-Alzheimer’s disease components in Verbena officinalis Linn

Quinolizidine-Type Alkaloids: Chemodiversity, Occurrence, and Bioactivity

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

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