Triterpenoids with α-glucosidase inhibitory activity and cytotoxic activity from the leaves of<i>Akebia trifoliata</i>

Ouyang, Jin-Kui; Dong, Lu; Xu, Qiao-Lin; Wang, Jing; Liu, Shaobo; Qian, Tao; Tan, Jian‐Wen

doi:10.1039/c8ra08894b

Cited by 22 publications

(13 citation statements)

References 17 publications

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“…However, only 38.30% of patients with grade III acne had an excellent response, 5% had a moderate response and 56.66% had a good response. There were no significant adverse effects in all the patients who received the medications Gopal et al ( 2001 ), Jiang et al ( 2019 ), Feng et al ( 2020 ) Akebonoic acid Triterpenoids Akebia trifoliata 9.0 ND 409 (acarbose) ND ND ND Jeong et al ( 2007 ), Sánchez-González et al ( 2014 ),; Yuan et al ( 2015 ), Ouyang et al ( 2018 ) …”

Section: Plant Secondary Metabolites As Alpha-glucosidase Inhibitorsmentioning

confidence: 97%

“…Interestingly, despite being structuraly very similar, triterpenoids isolated from Akebia trifoliata (compounds 80–88; online resource 1 and 2) showed a broad variation in the reported IC 50 against alpha-glucosidase (9–592 µM) (Ouyang et al 2018 ). While compounds 83 and 84 showed comparable IC 50 values and low inhibitory activity, the structurally similar compound gypsogenic acid (87) exhibited significantly higher inhibition that can be attribituted to the presence of a carboxy group at positions 23.…”

Section: Plant Secondary Metabolites As Alpha-glucosidase Inhibitorsmentioning

confidence: 99%

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A review of alpha-glucosidase inhibitors from plants as potential candidates for the treatment of type-2 diabetes

et al. 2021

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Diabetes mellitus is a multifactorial global health disorder that is rising at an alarming rate. Cardiovascular diseases, kidney damage and neuropathy are the main cause of high mortality rates among individuals with diabetes. One effective therapeutic approach for controlling hyperglycemia associated with type-2 diabetes is to target alpha-amylase and alpha-glucosidase, enzymes that catalyzes starch hydrolysis in the intestine. At present, approved inhibitors for these enzymes are restricted to acarbose, miglitol and voglibose. Although these inhibitors retard glucose absorption, undesirable gastrointestinal side effects impede their application. Therefore, research efforts continue to seek novel inhibitors with improved efficacy and minimal side effects. Natural products of plant origin have been a valuable source of therapeutic agents with lesser toxicity and side effects. The anti-diabetic potential through alpha-glucosidase inhibition of plant-derived molecules are summarized in this review. Eight molecules (Taxumariene F, Akebonoic acid, Morusin, Rhaponticin, Procyanidin A2, Alaternin, Mulberrofuran K and Psoralidin) were selected as promising drug candidates and their pharmacokinetic properties and toxicity were discussed where available. Supplementary Information The online version contains supplementary material available at 10.1007/s11101-021-09773-1.

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Section: Plant Secondary Metabolites As Alpha-glucosidase Inhibitorsmentioning

confidence: 97%

Section: Plant Secondary Metabolites As Alpha-glucosidase Inhibitorsmentioning

confidence: 99%

A review of alpha-glucosidase inhibitors from plants as potential candidates for the treatment of type-2 diabetes

et al. 2021

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“…Although the biological activities of compounds 14 and 17 have not been described yet, compound 15 was reported to exhibit anti-HIV-1 protease activity [ 37 ], antibacterial activity [ 38 ], an inhibitory effect on Aβ42-induced fibrillogenesis [ 39 ], an α-glucosidase inhibitory effect, and moderate in vitro cytotoxic activity against human cancer cell lines [ 40 ]. Compound 15 has been isolated mostly from the flowering plant family Lardizabalaceae, such as Stauntonia obovatifoliola , Akebia quinata , and Akebia trifoliata [ 37 , 38 , 39 , 40 ]. Compound 16 , which was previously isolated from the Colombian climbing plant Boussingaultia baselloides , was found to exhibit hypoglycemic activity in rats [ 41 ].…”

Section: Oleanane Triterpenoid Saponinsmentioning

confidence: 99%

Chemical Structure and Biological Activities of Secondary Metabolites from Salicornia europaea L.

et al. 2021

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Salicornia europaea L. is a halophyte that grows in salt marshes and muddy seashores, which is widely used both as traditional medicine and as an edible vegetable. This salt-tolerant plant is a source of diverse secondary metabolites with several therapeutic properties, including antioxidant, antidiabetic, cytotoxic, anti-inflammatory, and anti-obesity effects. Therefore, this review summarizes the chemical structure and biological activities of secondary metabolites isolated from Salicornia europaea L.

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“…In this research, T 1 – T 3 possessed excellent activity with an IC 50 value 42.1±5.4, 19.6±3.2, and 11.2±2.3 μM in parallel with the standard drug acarbose (IC 50 =106.3±8.2 μM), whose α‐glucosidase inhibitory effect was approximately 2, 5 and 9‐fold stronger than acarbose, respectively. As shown in Table 1, the T 1 – T 3 inhibitory effects of α‐glucosidase are weaker than those previously reported [29,30] . These results indicated that the T 1 – T 3 in the stems of A. trifoliata were significant α‐glucosidase inhibitors and had great prospects as effective and safe hypoglycemic agents for diabetes control.…”

Section: Resultsmentioning

confidence: 68%

Natural Triterpenoids Isolated from Akebia trifoliata Stem Explants Exert a Hypoglycemic Effect via α‐Glucosidase Inhibition and Glucose Uptake Stimulation in Insulin‐Resistant HepG2 Cells

Bian

Yang

Elango

et al. 2021

Chemistry & Biodiversity

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The inhibition of α‐glucosidase activity is a prospective approach to attenuate postprandial hyperglycemia in the treatment of type 2 diabetes mellitus (T2DM). Herein, the inhibition of α‐glucosidase by three compounds T1–T3 of Akebia trifoliata stem, namely hederagenin (T1), 3‐epiakebonoic acid (T2), and arjunolic acid (T3) were investigated using enzyme kinetics and molecular docking analysis. The three triterpenoids exhibited excellent inhibitory activities against α‐glucosidase. T1–T3 showed the strongest inhibition with IC50 values of 42.1±5.4, 19.6±3.2, and 11.2±2.3 μM, respectively, compared to the acarbose positive control (IC50=106.3±8.2). Enzyme inhibition kinetics showed that triterpenoids T1–T3 demonstrated competitive, mixed, and noncompetitive‐type inhibition against α‐glucosidase, respectively. The inhibition constant (Ki) values were 21.21, 7.70, and 3.18 μM, respectively. Docking analysis determined that the interaction of ligands T1–T3 and α‐glucosidase was mainly forced by hydrogen bonds and hydrophobic interactions, which could result in improved binding to the active site of the target enzyme. The insulin resistant (IR)‐HepG2 cell model used in this study (HepG2 cells exposed to 10−7 M insulin for 24 h) and glucose uptake assays showed that compounds T1–T3 had no cytotoxicity with concentrations ranging from 6.25 to 25 μM and displayed significant stimulation of glucose uptake in IR‐HepG2 cells. Thus, triterpenoids T1–T3 showed dual therapeutic effects of α‐glucosidase inhibition and glucose uptake stimulation and could be used as potential medicinal resources to investigate new antidiabetic agents for the prevention or treatment of diabetes.

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Triterpenoids with α-glucosidase inhibitory activity and cytotoxic activity from the leaves ofAkebia trifoliata

Abstract: Ten pentacyclic triterpenoids including a new multiflorane triterpene acid, 2α,3β,23-trihydroxymultiflor-7-en-28-oic acid (1), and a new lupane triterpene monoglucoside named akebiaoside C (2), were obtained from the leaves ofAkebia trifoliata.

Cited by 22 publications

References 17 publications

A review of alpha-glucosidase inhibitors from plants as potential candidates for the treatment of type-2 diabetes

A review of alpha-glucosidase inhibitors from plants as potential candidates for the treatment of type-2 diabetes

Chemical Structure and Biological Activities of Secondary Metabolites from Salicornia europaea L.

Natural Triterpenoids Isolated from Akebia trifoliata Stem Explants Exert a Hypoglycemic Effect via α‐Glucosidase Inhibition and Glucose Uptake Stimulation in Insulin‐Resistant HepG2 Cells

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