Aconapelsulfonines A and B, seco C20-diterpenoid alkaloids deriving via Criegee rearrangements of napelline skeleton from Aconitum carmichaelii

Liu, Hui; Wu, Yu-Zhuo; Guo, Qing‐Lan; Shao, Shuai; Chen, Xu; Zhang, Tiantai; Shi, Jian‐Gong

doi:10.1016/j.cclet.2020.09.062

Cited by 14 publications

(5 citation statements)

References 40 publications

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“…Studies on the secondary metabolites of natural sources of animals, plants, or microorganisms are still one of the important contents of modern drug research [25–27]. Diterpenoid alkaloids have long attracted the interest of chemists and pharmacologists because of their complex chemical structures and toxicity [7–9, 23, 16, 28–30]. In previous studies, more than 1000 diterpene alkaloids were discovered in Aconitum plants.…”

Section: Discussionmentioning

confidence: 99%

“…It is recorded in “flora of China” as having antispasmodic, analgesic, dispelling wind and dampness, and antipyretic effects [3–5]. However, the root tubers of most aconite plants are highly toxic [6–10], as well as other toxic components [11–12]. So far, More than 1000 diterpene alkaloids have been isolated from the alcoholic or aqueous extracts of the tuberous roots of the aconite plant.…”

Section: Introductionmentioning

confidence: 99%

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High‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry for profiling diterpenoid alkaloids in Aconitum species

Jiang

Deng

Zhou

et al. 2022

Separation Science Plus

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Aconitum is known for being rich in toxic diterpenoid alkaloids, and many of them are unilateral medicinal materials constituting traditional Chinese medicine, which have important clinical uses. Previous liquid chromatography‐mass spectrometry studies were mainly focused on a few common species, but lacked in‐depth and detailed research on other species in the same genus, although they have similar or even the same uses. In this study, a comprehensive analysis of the high‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry data by semi‐quantitative comparisons of the accurate molecular weight and fragmentation pathway of standards was introduced to investigate the diterpenoid alkaloids in four dried root tubers of A. kusnezoffii Reichb., A. carmichaelii Radix., A. pendulum Busch., and A. brachypodum Diels. Thirty‐two diterpenoid alkaloids were identified by the molecular networking platform. Their structures were determined by tandem mass spectrometry fragmentation comparisons, and structures that connect fatty acyl groups with different modifications at the C‐8 position which in previous studies paid little attention may have better digestion and absorption behavior in drug clinic uses. This work provides a basis for further understanding the clinical efficacy of Aconitum herbs.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

High‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry for profiling diterpenoid alkaloids in Aconitum species

Jiang

Deng

Zhou

et al. 2022

Separation Science Plus

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“…Aconicarnine E (241) inhibited acetic acid-induced writhing in mice by 43.8% at 1.0 mg/kg [93]. Aconapelsulfonines A (261) and B (262) showed specific analgesic effects at the dose of 0.3 mg/kg, with inhibition rates of 63.6% and 19.3% (morphine, 84.6%), respectively [99]. Aconicarmisulfonines B (263) and C (264) displayed analgesic effects in mice, with inhibition rates of 31.26% and 26.84%, respectively [95].…”

Section: Analgesic Activitymentioning

confidence: 99%

“…Rearranged C20-DAs retain the characteristics of C20-DAs but with altered skeletons. Eleven new compounds (256-266) obtained from Aconitum belong to this class [37,40,84,95,98,99]. Compounds 256-258 are rearranged C20-DAs with racemulosine skeletons derived from denudatine-type DAs via double Wanger-Meerwein rearrangements of rings A and C [84].…”

mentioning

confidence: 99%

“…Compounds 259-260 are zwitterionic sulfonated C20-DAs with a rearranged atisane skeleton. Compounds 261-262 are two sulfonated seco C20-DAs originating from the Criegee rearrangements; notably, compound 261 is a 13,16-seco-napelline DA, and 262 is a 12,13seco-napelline DA [99]. Compounds 263-264 are novel DAs derived through semipinacol rearrangements of the napelline-type DAs, which migrate through C13−C16 and C15−C6 bonds, respectively [95].…”

mentioning

confidence: 99%

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Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Wang,

Xin,

Sun

et al. 2024

Molecules

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Terpenoid alkaloids are recognized as a class of compounds with limited numbers but potent biological activities, primarily derived from plants, with a minor proportion originating from animals and microorganisms. These alkaloids are synthesized from the same prenyl unit that forms the terpene skeleton, with the nitrogen atom introduced through β-aminoethanol, ethylamine, or methylamine, leading to a range of complex and diverse structures. Based on their skeleton type, they can be categorized into monoterpenes, sesquiterpenes, diterpenes, and triterpene alkaloids. To date, 289 natural terpenoid alkaloids, excluding triterpene alkaloids, have been identified in studies published between 2019 and 2024. These compounds demonstrate a spectrum of biological activities, including anti-inflammatory, antitumor, antibacterial, analgesic, and cardioprotective effects, making them promising candidates for further development. This review provides an overview of the sources, chemical structures, and biological activities of natural terpenoid alkaloids, serving as a reference for future research and applications in this area.

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The diterpenoid alkaloids

Liu

Qin

et al. 2022

The Alkaloids: Chemistry and Biology

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Aconapelsulfonines A and B, seco C20-diterpenoid alkaloids deriving via Criegee rearrangements of napelline skeleton from Aconitum carmichaelii

Cited by 14 publications

References 40 publications

High‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry for profiling diterpenoid alkaloids in Aconitum species

High‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry for profiling diterpenoid alkaloids in Aconitum species

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

The diterpenoid alkaloids

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