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Bioactive Phytochemicals Isolated from Akebia Quinata Enhances Glucose-Stimulated Insulin Secretion by Inducing PDX-1

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Bioactive Phytochemicals Isolated from Akebia Quinata Enhances Glucose-Stimulated Insulin Secretion by Inducing PDX-1 plants Article Bioactive Phytochemicals Isolated from Akebia quinata Enhances Glucose-Stimulated Insulin Secretion by Inducing PDX-1 Dahae Lee 1, Jin Su Lee 2, Jurdas Sezirahiga 3, Hak Cheol Kwon 4 , Dae Sik Jang 2,* and Ki Sung Kang 1,* 1 College of Korean Medicine, Gachon University, Seongnam 13120, Korea; [email protected] 2 Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, Korea; [email protected] 3 College of Medicine and Health Sciences, University of Rwanda, Kigali 3286, Rwanda; [email protected] 4 Natural Products Research Center, Korea Institute of Science and Technology, Gangneung 210-340, Korea; [email protected] * Correspondence: [email protected] (D.S.J.); [email protected] (K.S.K.); Tel.: +82-2-961-0719 (D.S.J.); +82-31-750-5402 (K.S.K.) Received: 10 July 2020; Accepted: 19 August 2020; Published: 24 August 2020 Abstract: Chocolate vine (Akebia quinata) is consumed as a fruit and is also used in traditional medicine. In order to identify the bioactive components of A. quinata, a phytosterol glucoside stigmasterol-3-O-β-d-glucoside (1), three triterpenoids maslinic acid (2), scutellaric acid (3), and hederagenin (4), and three triterpenoidal saponins akebia saponin PA (5), hederacoside C (6), and hederacolchiside F (7) were isolated from a 70% EtOH extract of the fruits of A. quinata (AKQU). The chemical structures of isolates 1–7 were determined by analyzing the 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data. Here, we evaluated the effects of AKQU and compounds 1–7 on insulin secretion using the INS-1 rat pancreatic β-cell line. Glucose-stimulated insulin secretion (GSIS) was evaluated in INS-1 cells using the GSIS assay. The expression levels of the proteins related to pancreatic β-cell function were detected by Western blotting. Among the isolates, stigmasterol-3-O-β-d-glucoside (1) exhibited strong GSIS activity and triggered the overexpression of pancreas/duodenum homeobox protein-1 (PDX-1), which is implicated in the regulation of pancreatic β-cell survival and function. Moreover, isolate 1 markedly induced the expression of extracellular signal-regulated protein kinases 1 and 2 (ERK1/2), insulin receptor substrate-2 (IRS-2), phosphoinositide 3-kinase (PI3K), and Akt, which regulate the transcription of PDX-1. The results of our experimental studies indicated that stigmasterol-3-O-β-d-glucoside (1) isolated from the fruits of A. quinata can potentially enhance insulin secretion, and might alleviate the reduction in GSIS during the development of T2DM. Keywords: Akebia quinata; stigmasterol-3-O-β-d-glucoside; insulin secretion; IRS-2; PI3K; Akt; PDX-1 1. Introduction Diabetes mellitus (DM) is one of the top 10 causes of global deaths, and affected 463 million people worldwide in 2019. Experts expect that the number of patients with DM will increase to 578 million by 2030 [1,2]. Type 2 diabetes mellitus (T2DM) is a metabolic disease, which comprises approximately 90% of all cases of DM [3]. The clinical characteristics of patients with T2DM are decreased insulin production and impaired insulin function, which leads to persistent hyperglycemia [4]. Patients with T2DM are unable to control the disease by lifestyle changes alone, and require drugs and insulin for reducing the hyperglycemia. Therefore, one of the major factors in the development of T2DM is the Plants 2020, 9, 1087; doi:10.3390/plants9091087 www.mdpi.com/journal/plants Plants 2020, 9, 1087 2 of 14 reduction of glucose-stimulated insulin secretion (GSIS) in pancreatic β-cells [5]. Numerous therapeutic strategies have been developed at present, however, only a handful of patients with T2DM achieve long-term glycemic control [6]. The first generation sulfonylureas continually induce the secretion of insulin regardless of the blood glucose levels, which consequently results in hypoglycemia [7]. Apart from the sulfonylurea class of drugs, the current oral anti-diabetic drugs, including dipeptidyl peptidase-4 (DPP-4) inhibitors, α-glucosidase inhibitors, biguanides, and thiazolidinediones, have been reported to have numerous side effects [8]. DPP-4 inhibitors reduce the postprandial glucose levels by inhibiting DPP-4, and have numerous side effects, including hypersensitivity, nasopharyngitis, and headache [9]. The α-glucosidase inhibitors delay the digestion and absorption of carbohydrates, which suppresses postprandial hyperglycemia, while the biguanide drugs increase insulin sensitivity. The latter two classes of drugs have been found to be associated with gastrointestinal (GI) side effects. [10]. Thiazolidinediones are peroxisome proliferators-activated receptor γ (PPAR-γ) agonists, and they improve insulin function while simultaneously causing hepatotoxicity [11]. Therefore, efforts to develop safer and more effective anti-diabetic drugs remain an important challenge. In step with the trend, numerous studies have been increasingly exploring the utilization of natural products in the development of anti-diabetic drugs in the recent years. Numerous plant-derived compounds can directly enhance insulin secretion both in vitro and in vivo, and have attracted attention as sources of novel pharmaceuticals [12–15]. Although these plant-derived compounds are still not clinically available, such studies are significant as they provide a reference for the identification of novel molecules or pathways that have a potential in controlling hyperglycemia. The common metabolic targets for natural products with anti-diabetic activity are largely divided into three. The first category of natural products target and control sugar homeostasis, the second category enhances insulin synthesis and secretion, while the third category regulates the insulin signaling pathway [10]. In T2DM, the dysfunction of pancreatic β-cells delay the rate of insulin secretion and could be indicative of disease progression [16]. Although the exact mechanism remains unclear, pancreas/duodenum homeobox protein-1 (PDX-1) and V-maf musculoaponeurotic fibrosarcoma oncogene homolog A (MAFA) are implicated in the development of pancreatic β-cells and the transcription of the insulin gene [17,18]. Defects in the glucose-stimulated transcription of the insulin gene in a Psammomys obesus model of T2DM resulted in 80–90% lower insulin secretion than that associated with PDX-1 deficiency, whereas MAFA remained unaffected [19]. This indicates that PDX-1 is essential for the glucose-stimulated transcription of the insulin gene. Therefore, identification of novel natural products that improve GSIS and enhance the expression of PDX-1 may be beneficial for the development of safer and more effective anti-diabetic drugs. Akebia quinata (Thunb.) Decne. is a creeping woody vine that is distributed in East Asia, including Korea, China, and Japan [20–22]. It belongs to the Lardizabalaceae family of plants and is commonly known as “wild banana” in China and “Chocolate vine” in the Unites States [21–23]. Owing to their pharmacological activities, the fruits of A. quinata are generally used in Traditional Chinese Medicine as antiphlogistic [24], antineoplastic, and antidiuretic agents [23,24]. However, to the best of our knowledge, no previous studies have investigated the anti-diabetic activity of A. quinata and the compounds isolated from A. quinata. In our efforts to identify the bioactive compounds of A. quinata that have anti-diabetic properties, we performed a chemical investigation of a 70% EtOH extract of the fruits of A. quinata (AKQU). The effects of AKQU and the isolated compounds on insulin secretion were additionally evaluated using this GSIS assay, and the GSIS activity was expressed in terms of the glucose stimulated index (GSI). GSI reflected the GSIS ratio of INS-1 cells stimulated by 16.7 and 3.3 mM glucose. Western blotting was performed for investigating the mechanisms underlying the observed activity in INS-1 cells. The INS-1 rat pancreatic β-cell line secretes insulin in response to concentrations of glucose [25]. In this study, we found that the AKQU increased GSIS in INS-1 cells. The chemical analysis of AKQU led to the isolation of a phytosterol glucoside (1), three triterpenoids (2–4), and three triterpenoidal saponins (5–7). The chemical structures of the isolates 1–7 were determined by Plants 2020, 9, 1087 3 of 14 Plants 2020, 9, x FOR PEER REVIEW 3 of 14 triterpenoidal saponins (5–7). The chemical structures of the isolates 1–7 were determined by interpretation of the 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data (Figure1). interpretation of the 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data (Figure 1). From the GSIS assay, we identified that compounds 1–5 induced insulin secretion in INS-1 cells. From the GSIS assay, we identified that compounds 1–5 induced insulin secretion in INS-1 cells. Interestingly, the effect of compound 1 on insulin secretion was similar to that of the oral sulfonylurea Interestingly, the effect of compound 1 on insulin secretion was similar to that of the oral sulfonylurea drug, gliclazide, that induces hypoglycemia, at a concentration of 10 µM. Additionally, only compound drug, gliclazide, that induces hypoglycemia, at a concentration of 10 µM. Additionally, only 1 induced the overexpression of PDX-1. Compound 1 also induced the overexpression of extracellular compound 1 induced the overexpression of PDX-1. Compound 1 also induced the overexpression of signal-regulated protein kinases 1 and 2 (ERK1/2), insulin receptor substrate-2 (IRS-2), phosphoinositide extracellular signal-regulated protein kinases 1 and 2 (ERK1/2), insulin receptor substrate-2 (IRS-2), 3-kinase (PI3K), and Akt, which are associated with β-cell function and enhanced insulin secretion, phosphoinositide 3-kinase (PI3K), and Akt, which are associated with β-cell function and enhanced via mechanisms upstream of PDX-1. Herein, we report the isolation of compounds 1–7, along with insulin secretion, via mechanisms upstream of PDX-1. Herein, we report the isolation of compounds their effects on insulin secretion and the underlying mechanisms of action. 1–7, along with their effects on insulin secretion and the underlying mechanisms of action.
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