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Compounds from Toddalia asiatica: Immunosuppressant activity and absolute configurations

Reinhardt, Jakob K. and Zimmermann-Klemd, Amy M. and Danton, Ombeline and Smieško, Martin and Gründemann, Carsten and Hamburger, Matthias. (2020) Compounds from Toddalia asiatica: Immunosuppressant activity and absolute configurations. Journal of Natural Products, 83 (10). pp. 3012-3020.

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Official URL: https://edoc.unibas.ch/79193/

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Abstract

In a screening of an extract library from plants used in Traditional Chinese Medicine the MeOH extract of Toddalia asiatica inhibited proliferation of human primary T cells with an IC50 of 25.8 μg/mL. Activity in the extract was tracked by HPLC activity profiling, and a total of 15 compounds were characterized. Three compounds, toddalic acid (6) and both enantiomers (7a and 7b) of toddanolic acid (7), were new natural products, and two recently published compounds, (2′R)-toddalolactone 3′-O-β-d-glucopyranoside (10) and (2′S)-toddalolactone 2′-O-β-d-glucopyranoside (11), were described in detail for the first time. The absolute configurations of compounds 8, 9, 10, 12, 13, and 15 were determined by comparison of experimental and calculated ECD spectra. For glucosides 9 and 10, ECD data and chiral-phase HPLC of the aglycones after enzymatic hydrolysis confirmed the results. Nitidine chloride (4) inhibited proliferation of primary human T cells with an IC50 of 0.4 μM.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Computational Pharmacy (Lill)
05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Pharmazeutische Biologie (Hamburger)
05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Translationale Komplementärmedizin (Gründemann)
UniBasel Contributors:Hamburger, Matthias and Reinhardt, Jakob Klaus and Zimmermann-Klemd, Amy Marisa and Danton, Ombeline Réjane and Smiesko, Martin and Gründemann, Carsten
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0163-3864
e-ISSN:1520-6025
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:25 Oct 2021 14:25
Deposited On:25 Oct 2021 14:25

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