ChemInform Abstract: Hetisane‐Type Diterpenoid Alkaloids

Bessonova, I. A.; Saidkhodzhaeva, Sh. A.

doi:10.1002/chin.200136271

Cited by 3 publications

(3 citation statements)

References 1 publication

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“…When the fragmentor voltage increased to 375 V, it produced three minor fragment ions at m/z 312.1974, 294.1865 and 266.1867 by consecutive losses of H 2 O, H 2 O and CO. Compared with the literature reports (Rashkes et al , ; Bessonova and Saidkhodzhaeva, ), it could be tentatively identified as hetisine. Compound 14 ( m/z 344.2596) has the empirical molecular formula C 22 H 35 NO 5 and produced fragment ions at m/z 326.2458 [M + H − H 2 O] + and 300.1997 [M + H – CH 2 CHOH] + at 375 V, indicating that it could have one hydroxyl and ‐CH 2 CH 2 OH at the periphery of the skeleton.…”

Section: Tofms Fragmentation Behaviormentioning

confidence: 52%

Detection and identification of diterpenoid alkaloids, isoflavonoids and saponins in Qifu decoction and rat plasma by liquid chromatography–time‐of‐flight mass spectrometry

Tan

Jing

Zhu

et al. 2011

Biomedical Chromatography

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A liquid chromatography-time-of-flight mass spectrometric (LC-TOFMS) method has been developed for analysis of components in Qifu decoction (QFD), a traditional Chinese medical formula consisting of Radix Astragali and Acontium carmichaeli, and in rat plasma after oral administration. Based on accurate mass measurements within 3 ppm error for each molecular ion and subsequent fragment ions of TOFMS, as well as matching of empirical molecular formulae with those of published components in the in-house chemical library, a total of 44 major components including 21 diterpenoid alkaloids, 12 flavonoids and 11 saponins were identified in QFD. After oral administration of QFD, 22 components in rat plasma were detected and identified by comparing and contrasting the constituents measured in QFD with those in the plasma samples. The results provided valuable chemical information for further pharmacology and active mechanism research on QFD. LC-TOFMS was also applied for the comparison of relative peak area of major active components between QFD and the single herb extracts. The concentration ratios of major saponins detected in the crude herb Radix Astragali were found to be different from those in QFD. The experimental data indicated that the decocting process could result in differences in the amounts of active components.

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Section: Tofms Fragmentation Behaviormentioning

confidence: 52%

Detection and identification of diterpenoid alkaloids, isoflavonoids and saponins in Qifu decoction and rat plasma by liquid chromatography–time‐of‐flight mass spectrometry

Tan

Jing

Zhu

et al. 2011

Biomedical Chromatography

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“…Phytochemically, more than 197 diterpenoid alkaloids (DA) with complicated structures have been isolated from 56 Aconitum species of pharmacological significance 13 14 15 . These Aconitum DA have been reported to possess a broad range of bioactivities including anti-inflammatory properties 3 9 16 17 18 19 20 21 .…”

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confidence: 99%

Diterpenoid alkaloids of Aconitum laciniatum and mitigation of inflammation by 14-O-acetylneoline in a murine model of ulcerative colitis

Wangchuk

Navarro

Shepherd

et al. 2015

Sci Rep

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Aconitum laciniatum is used in Bhutanese traditional medicine for treating various chronic infections and inflammatory conditions. We carried out in-depth isolation and characterization of the phytochemicals from the root component and determined the anti-inflammatory effects of the isolated compounds against chemically-induced colitis in mice. Five diterpenoid alkaloids - pseudaconitine, 14-veratroylpseudaconine, 14-O-acetylneoline, neoline, and senbusine A - were isolated from A. laciniatum for the first time. Two of the alkaloids were tested for anti-inflammatory properties in the TNBS-induced colitis model in mice. Various parameters were measured to assess pathology including weight loss, clinical and macroscopic scores, histological structure and IFN-γ production in the gut. Of the two alkaloids tested, 14-O-acetylneoline showed significant protection against different parameters of colitic inflammation. Compared to control mice that received TNBS alone, mice treated with 14-O-acetylneoline experienced significantly less weight loss and had significantly lower clinical scores, macroscopic pathology and grades of histological inflammation. Moreover, colonic IFN-γ mRNA levels were significantly reduced in mice that received 14-O-acetylneoline compared to control mice that received TNBS alone. This alkaloid is now considered a novel anti-colitis drug lead compound.

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“…Aconitum spp. (monkshood) is one of the most extracted and isolated sources of DAs, where more than half of natural DAs were isolated from [ 10 , 11 , 12 , 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Classification, Toxicity and Bioactivity of Natural Diterpenoid Alkaloids

Thawabteh

Lelario

et al. 2021

Molecules

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Diterpenoid alkaloids are natural compounds having complex structural features with many stereo-centres originating from the amination of natural tetracyclic diterpenes and produced primarily from plants in the Aconitum, Delphinium, Consolida genera. Corals, Xenia, Okinawan/Clavularia, Alcyonacea (soft corals) and marine sponges are rich sources of diterpenoids, despite the difficulty to access them and the lack of availability. Researchers have long been concerned with the potential beneficial or harmful effects of diterpenoid alkaloids due to their structural complexity, which accounts for their use as pharmaceuticals as well as their lousy reputation as toxic substances. Compounds belonging to this unique and fascinating family of natural products exhibit a broad spectrum of biological activities. Some of these compounds are on the list of clinical drugs, while others act as incredibly potent neurotoxins. Despite numerous attempts to prepare synthetic products, this review only introduces the natural diterpenoid alkaloids, describing ‘compounds’ structures and classifications and their toxicity and bioactivity. The purpose of the review is to highlight some existing relationships between the presence of substituents in the structure of such molecules and their recognised bioactivity.

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ChemInform Abstract: Hetisane‐Type Diterpenoid Alkaloids

Cited by 3 publications

References 1 publication

Detection and identification of diterpenoid alkaloids, isoflavonoids and saponins in Qifu decoction and rat plasma by liquid chromatography–time‐of‐flight mass spectrometry

Detection and identification of diterpenoid alkaloids, isoflavonoids and saponins in Qifu decoction and rat plasma by liquid chromatography–time‐of‐flight mass spectrometry

Diterpenoid alkaloids of Aconitum laciniatum and mitigation of inflammation by 14-O-acetylneoline in a murine model of ulcerative colitis

Classification, Toxicity and Bioactivity of Natural Diterpenoid Alkaloids

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