C<sub>18</sub>-diterpenoid alkaloids in tribe <i>Delphineae</i> (Ranunculaceae): phytochemistry, chemotaxonomy, and bioactivities

Yan, Yuanfeng; Li, Xing; Wang, Ze; Xiao-yan, Yang; Yin, Tianpeng

doi:10.1039/d1ra08132b

Cited by 5 publications

(1 citation statement)

References 107 publications

(135 reference statements)

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“…However, when combined with representative compounds of other types of DAs, such as the C 18 -DAs lappaconitine (ED 50 , 0.05 mg kg −1 ) and deacetyllapaconitine (ED 50 , 0.05 mg kg −1 ) and the C 19 -DA 6-benzoylheteratisine (ED 50 , 0.035 mg kg −1 ), the antiarrhythmic effects of atisine-type DAs were not sufficient. 79 Therefore, further screening of this type of alkaloid was not performed.…”

Section: Biological Activitymentioning

confidence: 99%

Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids

Zheng,

Jiang,

Yan

et al. 2024

RSC Adv.

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Section: Biological Activitymentioning

confidence: 99%

Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids

Zheng,

Jiang,

Yan

et al. 2024

RSC Adv.

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Design, synthesis, evaluation, pharmacophore modeling, and 3D‐QSAR of lappaconitine analogs as potential analgesic agents

Wu,

Lai,

Zhang

et al. 2024

Archiv der Pharmazie

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Alleviating pain is crucial for patients with various diseases. This study aimed to enhance the analgesic properties of lappaconitine, a natural drug, through structural modifications. Specifically, carbamate analgesic active fragments were innovatively introduced at multiple sites on the benzene ring of lappaconitine. A total of 53 lappaconitine analogs were synthesized and evaluated. Compounds 5a, 5c, 5e, 6, and 15j addressed the narrow therapeutic window of lappaconitine, enhancing drug safety. Notably, carbamate analogs exhibited significantly enhanced analgesic activity, with compounds 5a and 5c having ED50 values of 1.2 and 1.6 mg/kg, respectively, indicating higher potency than lappaconitine (3.5 mg/kg). A metabolic analysis of compound 5e was conducted in mice, revealing its primary metabolic processes and metabolites, and providing preliminary exploration for the druggability. Given the multiple analgesic targets of lappaconitine, its analgesic mechanism remains inconclusive. This study, for the first time, analyzed the pharmacological activity characteristics of the lappaconitine analogs using a pharmacophore model and established a three‐dimensional quantitative structure–activity relationship (3D‐QSAR) to elucidate the quantitative relationship between the structures of the synthesized compounds and their analgesic activities. These findings provide valuable guidance for future structural modification and optimization of analgesic drugs.

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The Chemical Ecology of Plant Natural Products

Luo,

Hua,

Liu

et al. 2024

Progress in the Chemistry of Organic Natural Products

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C₁₈-diterpenoid alkaloids in tribe Delphineae (Ranunculaceae): phytochemistry, chemotaxonomy, and bioactivities

Abstract: This review systematically summarizes the C18-diterpenoid alkaloid (DA) compositions isolated from the genera Aconitum and Delphinium in the Delphineae tribe (Ranunculaceae).

Cited by 5 publications

References 107 publications

Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids

Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids

Design, synthesis, evaluation, pharmacophore modeling, and 3D‐QSAR of lappaconitine analogs as potential analgesic agents

The Chemical Ecology of Plant Natural Products

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C18-diterpenoid alkaloids in tribe Delphineae (Ranunculaceae): phytochemistry, chemotaxonomy, and bioactivities

Abstract: This review systematically summarizes the C18-diterpenoid alkaloid (DA) compositions isolated from the genera Aconitum and Delphinium in the Delphineae tribe (Ranunculaceae).

Cited by 5 publications

References 107 publications

Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids

Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids

Design, synthesis, evaluation, pharmacophore modeling, and 3D‐QSAR of lappaconitine analogs as potential analgesic agents

The Chemical Ecology of Plant Natural Products

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Product

Resources

About

C₁₈-diterpenoid alkaloids in tribe Delphineae (Ranunculaceae): phytochemistry, chemotaxonomy, and bioactivities