We reported the discovery of six novel coumarins, toddasirins A-F (1-6), each endowed with modified isoprenyl or geranyl side chains, derived from the roots of Toddalia asiatica. Comprehensive structural elucidation was achieved through multispectroscopic analyses, single-crystal X-ray diffraction experiments, and advanced quantum mechanical electronic circular dichroism (ECD) calculations. Furthermore, the anti-inflammatory activity of these compounds was assessed. Notably, compounds 1-3 and 6 demonstrated notable inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells, with 50% inhibitory concentration (IC) values of 3.22, 4.78, 8.90, and 4.31 μmol·L, respectively.
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Asiaticasics A-O, structurally intriguing coumarins from Toddalia asiatica with potential inflammatory inhibitory activity.
Phytochemistry
May 2024
Key Laboratory of Medicinal Chemistry for Natural Resource of Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, and School of Pharmacy, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University, Kunming, 650500, People's Republic of China; Southwest United Graduate School, Kunming, 650592, People's Republic of China. Electronic address:
Article Synopsis
- Researchers isolated 15 new prenylated coumarins (called asiaticasics A-O) from the ethyl acetate fraction of Toddalia asiatica, along with 9 known derivatives.
- The structures of these new compounds were confirmed using spectroscopic analysis and reference data.
- Biological tests showed compounds 3 and 12 exhibited anti-inflammatory effects, with compound 12 reducing pyroptosis in J774A.1 cells by inhibiting the NLRP3 inflammasome, supported by both biochemical and morphological evidence.
Six new coumarins from the roots of Toddalia asiatica and their anti-inflammatory activities.
Chin J Nat Med
November 2023
Science and Technology Innovation Center, Guangzhou University of Chinese Medicine, Guangzhou 510405, China. Electronic address:
We reported the discovery of six novel coumarins, toddasirins A-F (1-6), each endowed with modified isoprenyl or geranyl side chains, derived from the roots of Toddalia asiatica. Comprehensive structural elucidation was achieved through multispectroscopic analyses, single-crystal X-ray diffraction experiments, and advanced quantum mechanical electronic circular dichroism (ECD) calculations. Furthermore, the anti-inflammatory activity of these compounds was assessed.
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This study aims to investigate the therapeutic effect of alcohol extract of root and root bark of Toddalia asiatica(TAAE) on collagen-induced arthritis(CIA) in rats through phosphatidylinoinosidine-3 kinase/protein kinase B(PI3K/Akt) signaling pathway. To be specific, CIA was induced in rats, and then the rats were treated(oral, daily) with TAAE and Tripterygium Glycoside Tablets(TGT), respectively. The swelling degree of the hind leg joints was scored weekly.
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Aggregation-induced emission luminogens (AIEgens) are of great importance in optoelectronics and biomedical fields. However, the popular design philosophy by combining rotors with traditional fluorophores limits the imagination and structural diversity of AIEgens. Inspired by the fluorescent roots of the medicinal plant , we discovered two unconventional rotor-free AIEgens, 5-methoxyseselin (5-MOS) and 6-methoxyseselin (6-MOS).
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With the increasing demand for quality control in the traditional Chinese medicine industry, there is a need for the development of quality markers and a quick, non-destructive technique for the discrimination of related species. In our previous study, ultra-performance liquid chromatography (UPLC) was used for the simultaneous determination of five compounds, including three alkaloids (nitidine chloride, chelerythrine, and magnoflorine), one flavonoid (aurantiamarin), and one lignan (sesamin). In this study, the simultaneous quantification of the above-mentioned compounds could be used to discriminate the powders of roots from those of stems.
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