Rapid screening of diarylpentanoids from Daphne bholua

Dong, Shu-Hui; Lian, Mei-Ya; Han, Jinling; Ai, Yun-Fei; Zhou, Xiao-Fang; Bai, Ming; Huang, Xiao‐Xiao; Song, Shao‐Jiang

doi:10.1016/j.phytochem.2023.113614

Cited by 7 publications

(8 citation statements)

References 31 publications

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“…To determine the relative configurations of compounds 10 and 11 , NMR calculations combined with statistical analysis (RMSD, CMAE, CP3 probability analysis) were calculated for two possible configurations ( 10 *, 11 *). ,− The CP3 probability analysis of matching 10 * with 10 configurations, and 11 * with 11 was 99.2%, but the probability analysis of C data was not ideal. Then we used RMSD and CMAE analysis to determine the matching of compound 10 * with 10 configurations.…”

Section: Resultsmentioning

confidence: 99%

“…The subsequent chiral resolution led to the isolation of the enantiomers 1a/1b in a ratio of approximately 2:1 by chiral-phase HPLC using a Daicel Chiralpak IC column eluting at 0.6 mL/min with n-hexane− isopropanol (1:1, v/v) (Figure S9). 34 To determine the absolute configuration of compounds 1a and 1b, we examined the agreement between the calculated and experimental ECD spectra (Figure S10), 35,36 which defined the absolute configuration of 1a at C-6 as S, and 1b as R. The Mosher method is commonly used to determine the absolute configuration of secondary alcohols. Therefore, the absolute configuration of compound 1a was verified as 6S by the Mosher method, which is consistent with the results of comparing the calculated and experimental ECD spectra (Figure S10).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Expanded Application of Piper nigrum: Guided Isolation of Alkaloids with Inhibitory Activities of AChE/BuChE and Aβ Aggregation

Du,

Xu,

Lin

et al. 2024

J. Agric. Food Chem.

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Piper nigrum is a popular crop that can be used as seasoning or as an additive but its active ingredients also have an effect on the nervous system. Nineteen new amide alkaloids (1a/1b, 2−5, 6a/6b, 7, 8a/8b, 9, 10a/10b, 11a−11b, 12−14) were isolated from P. nigrum, guided by inhibitory activity of AChE and LC−MS/MS based on GNPS. The configurations were determined by extensive spectral analysis, Bulkiness rule, and NMR calculations. The inhibitory activities of AChE/BuChE and Aβ aggregation were tested, and the results showed compounds 2, 7, and 12 had significant inhibitory activities. These components were identified in the crude fraction and their relative quantities were tested, which suggested that compound 2 was the index component in the active site from P. nigrum.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Expanded Application of Piper nigrum: Guided Isolation of Alkaloids with Inhibitory Activities of AChE/BuChE and Aβ Aggregation

Du,

Xu,

Lin

et al. 2024

J. Agric. Food Chem.

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“…To determine its absolute configuration, the specific rotation of (2′ R , 3′ R , 6′ R )- 1 was calculated as +49.7 . From a comparison of the experimental value of [α] D 20 +30.0 ( c 0.1, MeOH), the absolute configuration of compound 1 was determined to be 2′ R , 3′ R , 6′ R . Based on the spectroscopic data, compound 1 was identified as a monoterpenoid coumarin and was given the trivial name ailancoumarin A ( 1 ).…”

Section: Resultsmentioning

confidence: 99%

Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Duan,

Wang,

Lian

et al. 2024

J. Agric. Food Chem.

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Demand for the exploration of botanical pesticides continues to increase due to the detrimental effects of synthetic chemicals on human health and the environment and the development of resistance by pests. Under the guidance of a bioactivity-guided approach and HSQC-based DeepSAT, 16 coumarin derivatives were discovered from the leaves of Ailanthus altissima (Mill.) Swingle, including seven undescribed monoterpenoid coumarins, three undescribed monoterpenoid phenylpropanoids, and two new coumarin derivatives. The structure and configurations of these compounds were established and validated via extensive spectroscopic analysis, acetonide analysis, and quantum chemical calculations. Biologically, 5 exhibited significant antifeedant activity toward the Plutella xylostella. Moreover, tyrosinase being closely related to the growth and development of larva, the inhibitory potentials of 5 against tyrosinase was evaluated in vitro and in silico. The bioactivity evaluation results highlight the prospect of 5 as a novel category of botanical insecticide.

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“…The AChE inhibitory activities were evaluated according to the modified Ellman's method, 47,48 using donepezil as the positive control. 50 µL PBS, 12.5 µL enzyme, 125 µL DTNB and 25 µL tested compounds were added to a 96-well plate and incubated overnight.…”

Section: Ache Inhibitory Activitymentioning

confidence: 99%

Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

Dong¹,

Han²,

Chang³

et al. 2023

Org. Chem. Front.

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Rapid screening of diarylpentanoids from Daphne bholua

Cited by 7 publications

References 31 publications

Expanded Application of Piper nigrum: Guided Isolation of Alkaloids with Inhibitory Activities of AChE/BuChE and Aβ Aggregation

Expanded Application of Piper nigrum: Guided Isolation of Alkaloids with Inhibitory Activities of AChE/BuChE and Aβ Aggregation

Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

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