Synthesis and SAR study of novel sarsasapogenin derivatives as potent neuroprotective agents and NO production inhibitors

Pan, Hui; Khang, Pham Van; Dong, Dong; Wang, Rui; Ma, Lei

doi:10.1016/j.bmcl.2016.11.070

Cited by 23 publications

(12 citation statements)

References 17 publications

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“…In the previous study, we have found that AA13 markedly ameliorated the cognitive deficit induced by scopolamine, mainly through upregulating the expression of BDNF and PSD95 in cortex (data not shown), which might prompt the neuroprotective potential of AA13. Neuroinflammation from aberrantly activated glia is an important mechanism that contributes to AD progression.…”

Section: Discussionmentioning

confidence: 81%

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Sarsasapogenin‐AA13 ameliorates Aβ‐induced cognitive deficits via improving neuroglial capacity on Aβ clearance and antiinflammation

et al. 2017

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Section: Discussionmentioning

confidence: 81%

“…AA13, a derivative of natural compound sarsasapogenin, was synthesized by Lei Ma's laboratory from School of Pharmacy, East China University of Science and Technology (Figure A) . A 5 mmol/L of stock solution of AA13 was dissolved in DMSO and stored at −80°C.…”

Section: Methodsmentioning

confidence: 99%

Sarsasapogenin‐AA13 ameliorates Aβ‐induced cognitive deficits via improving neuroglial capacity on Aβ clearance and antiinflammation

et al. 2017

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“…Among the secondary metabolites reported in this genus are mainly phenolic compounds and steroidal saponins 13,14 . Interest in the latter is due to their diverse biological activities, and the use of their aglycones (sapogenins) as raw material for the synthesis of potential steroidal drugs, such as chemotherapeutic agents, 15 immunomodulators 16 and neuroprotectants 17 …”

Section: Introductionmentioning

confidence: 99%

Comparative study of steroidal sapogenins content in leaves of five Agave species

et al. 2022

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BACKGROUND Agaves are mainly used to produce alcoholic beverages such as tequila, mezcal and bacanora. However, the leaves constitute more than 50% of the plant and are not used in the production process, so they are considered waste. This plant material can be used as a source of bioactive compounds such as terpenes, flavonoids and saponins. Therefore, the objective of this study was to characterize the aglycone type of saponins and to quantify three steroidal sapogenins in leaves of five Agave species collected in different regions of Guerrero and Oaxaca, Mexico. RESULTS Analysis by gas chromatography–flame ionization detection of the hydrolyzed methanolic extracts showed that diosgenin and tigogenin were the most abundant sapogenins identified in the five Agave species. Differences in the content of these sapogenins were found in the same species collected in different localities. The leaves of Agave americana var. oaxacensis L. (Oaxaca) had the highest diosgenin‐derived saponin content, while the leaves of A. angustifolia Haw. (Guerrero) had the highest tigogenin‐derived saponin content. Only in A. cupreata was sarsasapogenin identified, all three sapogenins occurring in the leaves of this species. For the first time, information is provided on the aglycones of the saponins produced in A. potatorum Zucc. and A. karwinskii Zucc. CONCLUSION This study made it possible to compare the content of diosgenin and tigogenin‐derived saponins in leaves of Agave species from Guerrero and Oaxaca. This information will be useful for better utilization of this plant material and add value to the process of mezcal elaboration. © 2022 Society of Chemical Industry.

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“…In our previous work, we synthesised several carbamate derivatives exhibiting neuroprotective and NO production inhibitory properties (Pan, Van Khang, Dong, Wang, & Ma, ). Among all the derivatives, AA13 has emerged as one of the most useful compounds to inhibit inflammatory reactions and ameliorate Aβ‐induced cognitive deficits (Dong et al, ; Huang et al, ).…”

Section: Introductionmentioning

confidence: 99%

A validated UPLC–MS/MS method for quantitative determination of a potent neuroprotective agent Sarsasapogenin‐AA13 in rat plasma: Application to pharmacokinetic studies

Pei

Zhao

et al. 2020

Biomedical Chromatography

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Sarsasapogenin‐AA13(AA13), a sarsasapogenin derivative, exhibited good neuroprotective and anti‐inflammatory activities in vitro and therapeutic effects on learning and memory dysfunction in amyloid‐β‐injected mice. A sensitive UPLC–MS/MS method was developed and validated to quantitatively determine AA13 in rat plasma and was further applied to evaluate the pharmacokinetic behaviour of AA13 in rats that were administered AA13 intravenously and orally. This method was validated to exhibit excellent linearity in the concentration range of 1–1000 ng/mL. The lower limit of quantification was 1 ng/mL for AA13 in rat plasma. Intra‐day accuracy for AA13 was in the range of 90–114%, and inter‐day accuracy was in the range of 97–103 %. The relative standard deviation of intra‐day and inter‐day assay was less than 15%. After a single oral administration of AA13 at the dose of 25 mg/kg, Cmax of AA13 was 1266.4 ± 316.1 ng/mL. AUC0–48 h was 6928.5 ± 1990.1 h·ng/mL, and t1/2 was 10.2 ± 0.8 h. Under intravenous administration of AA13 at a dosage of 250 μg/kg, AUC0–48 h was 785.7 ± 103.3 h⋅ng/mL, and t1/2 was 20.8 ± 7.2 h. Based on the results, oral bioavailability (F %) of AA13 in rats at 25 mg/kg was 8.82 %.

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Synthesis and SAR study of novel sarsasapogenin derivatives as potent neuroprotective agents and NO production inhibitors

Cited by 23 publications

References 17 publications

Sarsasapogenin‐AA13 ameliorates Aβ‐induced cognitive deficits via improving neuroglial capacity on Aβ clearance and antiinflammation

Sarsasapogenin‐AA13 ameliorates Aβ‐induced cognitive deficits via improving neuroglial capacity on Aβ clearance and antiinflammation

Comparative study of steroidal sapogenins content in leaves of five Agave species

A validated UPLC–MS/MS method for quantitative determination of a potent neuroprotective agent Sarsasapogenin‐AA13 in rat plasma: Application to pharmacokinetic studies

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