New anti-inflammatory withanolides from Physalis pubescens fruit
Graphical abstract
Introduction
The genus Physalis (Family: Solanaceae), which comprises more than 100 species, is widely distributed in the Americas, Asia and Europe [1,2]. Several species in this genus have attracted immense research interest due to their nutritional and pharmacological effects [3,4]. For instance, species including P. alkekengi var. franchetii have been commonly used in China given their medicinal values [5,6]. P. pubescens L. is one of the most important Physalis species cultivated in the northeast of China. Unlike P. alkekengi var. franchetii, which is widely used in the Traditional Chinese Medicine system, P. pubescens is often consumed as an edible fruit in China. Its ripened fruit, known as ‘Gu-Niang’, or husk tomato, or hairy ground berry, has yellow color, aromatic odor and sweet taste [7]. The fruit of P. pubescens is considered as good source of nutrients including minerals, organic acids, amino acids and carotenoids [5,8]. It is consumed either freshly, or as jam, juice, wine, and preserved fruit [8,9]. P. pubescens fruit has also been traditionally used as adjuvant treatment for inflammation related illnesses, such as sour throat, cough, and urogenital system disease [10]. Pharmacological studies have revealed that P. pubescens fruit possessed cancer-preventive [11], anti-inflammatory, immunoregulatory [12], diuretic [9], and antidiabetic activities [13]. In the past decade, phytochemicals including withanolides [7,14], terpenoids [15], as well as cinnamoyl and hydroxycinnamoyl derivatives [5] have been isolated and identified from the fruit of P. pubescens.
Among these chemical constituents, withanolides, a class of steroidal lactones, have been considered as characteristic secondary metabolites of Physalis genus [10,16,17], and over 200 withanolides have been identified from multiple plants from this genus [2]. Withanolides possess great chemical structural diversity, which are usually divided into unmodified withanolides and modified withanolides based on their skeletons. In addition, withanolides have been reported for several biological effects, including anti-inflammatory, antiproliferative, antimicrobial, and antifeedant activities [18]. In order to better understand the relationship between the presence of withanolides and the beneficial effects of consumption of P. pubescens, we conducted the current study. Herein, we reported the isolation and identification of eight withanolides (1–8), including four new ones (1, 2, 4 and 5), along with fifteen other constituents (9–23) from P. pubescens fruit. The anti-inflammatory effects of isolated withanolides were also evaluated and reported.
Section snippets
General experimental procedures
The optical rotations were measured on a MCP200 automatic polarimeter (Anton Paar, Graz, Austria) with methanol as solvent. IR spectra were recorded with a Tensor 27 FT-IR spectrometer (film) (Bruker Optik GmbH, Ettlingen, Germany). HRESIMS data were collected using a Micro TOF-Q mass spectrometer (Bruker Daltonics, Billerica, MA). 1D and 2D NMR spectra were performed on an Advance III-600 MHz spectrometer (Bruker Co., Rheinstetten, Germany) with dimethyl sulfoxide (DMSO‑d6) as solvents. Silica
Results and discussion
Eight withanolides (1–8), eight terpenoids (9–16), three phenylpropanoids (17–19), two flavonoids (20 and 21), and two monosaccharide derivatives (22 and 23) were isolated and identified from an ethanol extract of P. pubescens fruit. Among the isolates, 1, 2, 4 and 5 are new compounds and named physapubescins J-M, respectively. The structures of identified withanolides (1–8) are shown in Fig. 1.
A molecular formula of C32H48O10S with nine degrees of unsaturation was established for physapubescin
Declare of Competing Interest
None.
Funding
This work was supported by the National Natural Science Foundation of China [No. U1608282], Science and Technology Program of Liaoning Province [No. 2019JH2/10300003], and the Fundamental Research Funds for the Central Universities [No. N2020005].
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