Limonoids from the Fresh Young Leaves and Buds of Toona sinensis and Their Potential Neuroprotective Effects

• Published in: Journal of agricultural and food chemistry Vol. 68; no. 44; pp. 12326 - 12335
• Main Authors: Fu, Yan-Hui, Xie, Yu-Tong, Guo, Jia-Ming, Wang, Xiao-Ping, Jiang, Bo, Zhang, Wei, Qiang, Lei, Kong, Ling-Ying, Liu, Yan-Ping
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.11.2020; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Bioactive Constituents, Metabolites, and Functions; Chemistry; Chemistry, Applied; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Food Science & Technology; Humans; Life Sciences & Biomedicine; Limonins - chemistry; Limonins - isolation & purification; Molecular Structure; Neuroprotective Agents - chemistry; Neuroprotective Agents - isolation & purification; Physical Sciences; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Leaves - chemistry; Plant Shoots - chemistry; Science & Technology; Toona - chemistry; neuroprotective effects; toonasinenoids A−E; Toona sinensis; limonoids; GLYCOSIDES; OXIDATIVE STRESS; TRITERPENOIDS; toonasinenoids A-E; HETEROPHYLLUS; TWIGS; ROOT BARK; ALKALOIDS
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.0c06352

Toona sinensis, popularly known as Chinese toon or Chinese mahogany, is a perennial deciduous arbor belonging to the genus Toona in the Meliaceae family, which is widely distributed and cultivated in eastern and southeastern Asia. Its fresh young leaves and buds have been consumed as a very popular nutritious vegetable in China and confirmed to display a wide variety of biological activities. To investigate the chemical constituents and their potential health benefits from the fresh young leaves and buds of T. sinensis, a phytochemical study on its fresh young leaves and buds was therefore undertaken. In our current investigation, 16 limonoids (1–16), including four new limonoids, toonasinenoids A–D (1–4), and a new naturally occurring limonoid, toonasinenoid E (5), were isolated and characterized from the fresh young leaves and buds of T. sinensis. The chemical structures and absolute configurations of limonoids 1–5 were elucidated by comprehensive spectroscopic data analyses. All known limonoids (6–16) were identified via comparing their experimental spectral data containing mass spectrometry data, 1H and 13C nuclear magnetic resonance data, and optical rotation values to the data reported in the literature. All known limonoids (6–16) were isolated from T. sinensis for the first time. Furthermore, the neuroprotective effects of all isolated limonoids 1–16 against 6-hydroxydopamine-induced cell death in human neuroblastoma SH-SY5Y cells were assessed in vitro. Limonoids 1–16 exhibited notable neuroprotective activities, with EC50 values in the range from 0.27 ± 0.03 to 17.28 ± 0.16 μM. These results suggest that regular consumption of the fresh young leaves and buds of T. sinensis might prevent the occurrence and development of Parkinson’s disease (PD). Moreover, the isolation and characterization of these limonoids that exhibit notable neuroprotective activities from the fresh young leaves and buds of T. sinensis could be very significant for researching and developing new neuroprotective drugs used for the prevention and treatment of PD.