Discovery of Neuritogenic <i>Securinega</i> Alkaloids from <i>Flueggea suffruticosa</i> by a Building Blocks‐Based Molecular Network Strategy

He, Qi‐Fang; Wu, Zhen‐Long; Li, Liuren; Sun, Wanyang; Wang, Guiyang; Jiang, Ren‐Wang; Hu, Lijun; Shi, Lei; He, Rong‐Rong; Wang, Ying; Ye, Wen-Cai

doi:10.1002/ange.202103878

Cited by 5 publications

(11 citation statements)

References 35 publications

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“…Its molecular formula was determined as C 34 H 40 N 2 O 6 based on the HRESIMS data at m/z 595.2786 [M + Na] + (calcd for C 34 H 40 N 2 O 6 Na + , 595.2779). Analysis of its 1 H and 13 C NMR data (Table 1) revealed the presence of four methyls (including one acetylated), one methylene, five methines (including one oxygenated and two olefinic), and seven nonprotonated carbons (including four olefinic, one amide carbonyl, and one ester carbonyl). With the aid of the HRESIMS spectrum and NMR data (Table 1), compound 1 was predicted to be a highly symmetrical and homodimeric structure.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Dipeniroqueforins A–B and Peniroqueforin D: Eremophilane-Type Sesquiterpenoid Derivatives with Cytotoxic Activity from Penicillium roqueforti

Mo,

Zhang,

Jiang

et al. 2024

J. Org. Chem.

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Guided by the Global Natural Products Social (GNPS) molecular networking strategy, five undescribed eremophilane-type sesquiterpenoid derivatives (1−5) were isolated and identified from fungus Penicillium roqueforti, which was separated from the root soil of plant Hypericum beanii collected in Shennongjia Forestry District, Hubei Province. Dipeniroqueforins A−B (1−2), representing a lactamtype sesquiterpenoid skeleton with a highly symmetrical and homodimeric 5/6/6−6/6/5 hexacyclic system, are reported within the eremophilane-type family for the first time. Peniroqueforin D (5) represents the first example of a 1,2-seco eremophilane-type sesquiterpenoid derivative featuring an undescribed 7/6-fused ring system. The structures of these compounds were elucidated by various spectroscopic analyses, DP4+ probability analyses, ECD calculations, and single-crystal X-ray diffraction experiments. Furthermore, these isolates were evaluated for cytotoxicity, and the result uncovered that compound 1 displayed broad-spectrum activity. Further mechanistic study revealed that compound 1 could significantly upregulate the mRNA expression of genes related to the oxidative induction, leading to the abnormal ROS levels in tumor cells and ultimately causing tumor cell apoptosis.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Dipeniroqueforins A–B and Peniroqueforin D: Eremophilane-Type Sesquiterpenoid Derivatives with Cytotoxic Activity from Penicillium roqueforti

Mo,

Zhang,

Jiang

et al. 2024

J. Org. Chem.

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“…To date, MS/MS MN has accelerated the discovery of undescribed small molecules from complicated natural medicines. [29][30][31] MS/MS MN has been successfully used to track specific TS from E. senticosus leaves, and 106 saponins have been characterized by means of a targeted analysis strategy. 32 Therefore, the MS/MS MN strategy may guide a comprehensive profiling of TS from ESF extracts.…”

Section: Discussionmentioning

confidence: 99%

“…Natural products are a rich source of new therapeutic leads. To date, MS/MS MN has accelerated the discovery of undescribed small molecules from complicated natural medicines 29–31 . MS/MS MN has been successfully used to track specific TS from E. senticosus leaves, and 106 saponins have been characterized by means of a targeted analysis strategy 32 .…”

Section: Introductionmentioning

confidence: 99%

MS/MS molecular networking‐guided in‐depth profiling of triterpenoid saponins from the fruit of Eleutherococcus senticosus and their neuroprotectivity evaluation

Zhou

Ren

et al. 2022

Phytochemical Analysis

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Introduction: Eleutherococcus senticosus fruit (ESF) is a natural health supplement resource that has been extensively applied as a tonic for the nervous system. The structures and neural bioactivities of triterpenoid saponins (TS), which are the major constituents of ESF, have not been comprehensively analyzed thus far.Objective: We conducted a complete in-depth MS/MS molecular networking (MN)based targeted analysis of TS from the crude extract of ESF and investigated its neuroprotective value.Methods: An MS/MS MN-guided strategy was used to rapidly present a series of precursor ions (PIs) of TS in a compound cluster as TS-targeted information used in the discovery and characterization of TS. In addition, a prepared TS-rich fraction of ESF was assayed for its restraining effects on β-amyloid-induced inhibition of neurite outgrowth.Results: A total of 87 TS were discovered using a PI tracking strategy, 28 of which were characterized as potentially undescribed structures according to their highresolution MS values. Furthermore, the TS-rich fraction can significantly reduce

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“…Based on mass spectrometry data, a network of compounds with structural similarity is created by using molecular networking [16,17]. So, it has been widely used in the discovery and identification of ingredients of TCM, especially in the discovery of new compounds [18]. Metabolites usually contain the main frameworks of the parent drug and exhibit a similar fragmentation pattern in the MS/MS spectrum [16].…”

Section: Introductionmentioning

confidence: 99%

An integrated strategy to reveal the potential anti‐asthma mechanism of peimine by metabolite profiling, network pharmacology, and molecular docking

Tian

Wei

Yang

et al. 2022

J of Separation Science

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Peimine, one of the major quality markers in Fritillaria Cirrhosae Bulbus, was expected to become a new anti‐asthma drug. However, its metabolic profiles and anti‐asthma mechanism have not been clarified previously. In this study, a method was developed for the detection of peimine metabolites in vitro by ultra‐high‐performance liquid chromatography coupled with hybrid triple quadrupole time‐of‐flight mass spectrometry. The potential anti‐asthma mechanism was predicted by an integrated analysis of network pharmacology and molecular docking. A total of 19 metabolites were identified with the aid of software and molecular networking. The metabolic profiles of peimine elucidated that the metabolism was a multi‐pathway process with characteristics of species difference. The network pharmacology results showed that peimine and its metabolites could regulate multiple asthma‐related targets. The above targets were involved in various regulatory pathways linked to asthma. Moreover, the results of molecular docking showed that both peimine and its metabolites had a certain affinity with the β2 adrenergic receptor. The results provided not only important references to understand the metabolism and pharmacodynamic changes of peimine in vitro, but also supporting data for further pharmacological evaluation. It also provided a new perspective for clarifying the functional changes of traditional Chinese medicine in vitro.

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Discovery of Neuritogenic Securinega Alkaloids from Flueggea suffruticosa by a Building Blocks‐Based Molecular Network Strategy

Cited by 5 publications

References 35 publications

Dipeniroqueforins A–B and Peniroqueforin D: Eremophilane-Type Sesquiterpenoid Derivatives with Cytotoxic Activity from Penicillium roqueforti

Dipeniroqueforins A–B and Peniroqueforin D: Eremophilane-Type Sesquiterpenoid Derivatives with Cytotoxic Activity from Penicillium roqueforti

MS/MS molecular networking‐guided in‐depth profiling of triterpenoid saponins from the fruit of Eleutherococcus senticosus and their neuroprotectivity evaluation

An integrated strategy to reveal the potential anti‐asthma mechanism of peimine by metabolite profiling, network pharmacology, and molecular docking

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