A comprehensive review of cycloastragenol: Biological activity, mechanism of action and structural modifications

He, Mengting; Wang, Ke; Che, Haojie; Wang, Hong; Zhang, Guiming; Yao, Jingchun

doi:10.1016/j.ejmcr.2022.100060

Cited by 2 publications

(1 citation statement)

References 86 publications

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“…Moreover, Smith degradation showed high selectivity and produced CAG as a predominant product, but these results were accompanied by the cleavage of the cyclopropane ring, dehydration, acetylation, and partial oxidation that may not individually occur. In fact, under specific reaction conditions, CAG undergoes chemical transformations, such as acetylation, glycosylation, ring opening, oxidation, and halogenation [27]. The results discussed herein present a real profile of the various transformations induced via the Smith degradation of astragaloside IV, and this profile is important for carrying out the quality control of CAG.…”

Section: Uplc-ltq-orbitrap-ms Conditions Required For the Determinati...mentioning

confidence: 83%

Using UPLC-LTQ-Orbitrap-MS and HPLC-CAD to Identify Impurities in Cycloastragenol, Which Is a Pre-Clinical Candidate for COPD

Zhu,

Zhang,

et al. 2023

Molecules

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Chronic obstructive pulmonary disease (COPD) is a highly prevalent disease that has become the third leading cause of death worldwide. Cycloastragenol (CAG), which is the genuine sapogenin of the main active triterpene saponins in Astragali radix, is a bioavailable pre-clinical candidate for chronic obstructive pulmonary disease (COPD), and it was investigated in our previous study. In order to progress medical research, it was first efficiently produced on a 2.5-kg scale via Smith degradation from astragaloside IV (AS-IV). Simultaneously, since the impurity profiling of a drug is critical for performing CMC documentation in pre-clinical development, a study on impurities was carried out. As these structures do not contain chromophores and possess weak UV absorption characteristics, HPLC-CAD and UPLC-LTQ-Orbitrap-MS were employed to carry out the quality control of the impurities. Then, column chromatography (CC), preparative thin-layer chromatography (PTLC), and crystallization led to the identification of 15 impurities from CAG API. Among these impurities, compounds 1, 4, 9, 10, 14, and 15 were elucidated via spectroscopic analysis, and 2–3, 5–8, and 11–13 were putatively identified. Interestingly, the new compounds 9 and 14 were rare 10, 19-secocycloartane triterpenoids that displayed certain anti-inflammatory activities against LPS-induced lymphocyte cells and CSE-induced MLE-12 cells. Additionally, a plausible structural transformation pathway of the degradation compounds from CAG or AS IV was proposed. The information obtained will provide a material basis to carry out the quality control and clinical safety assurance of API and related prescriptions. Reasonable guidance will also be provided regarding the compounds with weak UV absorption characteristics.

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Section: Uplc-ltq-orbitrap-ms Conditions Required For the Determinati...mentioning

confidence: 83%

Using UPLC-LTQ-Orbitrap-MS and HPLC-CAD to Identify Impurities in Cycloastragenol, Which Is a Pre-Clinical Candidate for COPD

Zhu,

Zhang,

et al. 2023

Molecules

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Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision

Aydoğan,

Pandey,

Fronczek

et al. 2024

J. Nat. Prod.

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The phytochemical investigation of the MeOH extract of Astragalus condensatus roots led to the discovery of a new tetrahydropyran cycloartane-type triterpenoid, astracondensatol A (1), alongside six known cyclocephagenol derivatives (2, 3, 20, 32, 35, and 36). Elucidation of their structures involved 1D and 2D-NMR spectroscopy and mass data analysis. Upon comparing NMR spectroscopic data with prior literature, several carbon shift anomalies, particularly at C-24, prompted a reevaluation using quantum chemical calculations, resulting in the revision of the 24S to 24R absolute configuration for compound 2 and 38 other reported cyclocephagenol-type triterpenoids. X-ray crystallography data further supported the analysis in establishing the absolute configuration of compound 2. Ambiguous NOE correlations and publication bias could have played a significant role in missassigning the C-24 absolute configuration in tetrahydropyran cycloartane-type triterpenoids.

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A comprehensive review of cycloastragenol: Biological activity, mechanism of action and structural modifications

Cited by 2 publications

References 86 publications

Using UPLC-LTQ-Orbitrap-MS and HPLC-CAD to Identify Impurities in Cycloastragenol, Which Is a Pre-Clinical Candidate for COPD

Using UPLC-LTQ-Orbitrap-MS and HPLC-CAD to Identify Impurities in Cycloastragenol, Which Is a Pre-Clinical Candidate for COPD

Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision

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