Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Jiang, Cheng‐Shi; Liang, Lin-Fu; Guo, Yue‐Wei

doi:10.1038/aps.2012.90

Cited by 182 publications

(134 citation statements)

References 208 publications

(228 reference statements)

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“…The assignment was confirmed by the HMBC correlations (Fig. 2) Considering potent PTP1B inhibitory property previously reported for numerous prenylated flavonoids, 1) all the isolates were subjected to testing in vitro for their inhibitory effects against PTP1B with oleanolic acid as the positive control (IC 50 =2.74±0.20 µM), which has proved to be an excellent PTP1B inhibitor. 26,27) As shown in Table 2, all the compounds tested, except for 4, inhibited strongly PTP1B activity.…”

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confidence: 68%

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Aglaiabbrevins A–D, New Prenylated Bibenzyls from the Leaves of <i>Aglaia abbreviata</i> with Potent PTP1B Inhibitory Activity

Sun

Jiang

Zhang

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl] bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were elucidated on the basis of extensive spectroscopic experiments, mainly one and two dimensional (1D-and 2D)-NMR, and the absolute configuration of 5 was determined by the measurement of specific rotation. The isolated compounds were evaluated for their protein tyrosine phosphatase-1B (PTP1B) inhibitory activity. The results showed that compounds 5-7 exhibited more potent PTP1B inhibitory effects with IC 50 values of 2.58 0.52, 2.44 0.35, and 2.23 0.14 µM, respectively, than the positive control oleanolic acid (IC 50 2.74 0.20 µM). On the basis of the data obtained, these bibenzyls with the longer C-2 prenyl groups may be considered as potential lead compounds for the development of new anti-obesity and anti-diabetic agents. Also, the PTP1B inhibitory effects for prenylated bibenzyls are being reported for the first time.Key words Aglaia abbreviata; prenylated bibenzyl; aglaiabbrevin; protein tyrosine phosphatase-1B inhibitor; potential lead compound Type 2 diabetes (T2D) is a chronic disorder characterized by hyperglycemia associated with a gradual decline in insulin sensitivity and/or insulin secretion, and has become one of the most serious health problems worldwide. On the other hand, obesity is one of the major risk factors for developing T2D due to insulin resistance. 1) Protein tyrosine phosphatases (PTPs) are responsible for the dephosphorylation of tyrosine residues and are considered negative regulators of insulin signaling.2) Among the various members of the PTP superfamily, PTP1B plays a critical role in metabolic signaling pathways, which places it in an ideal position as a therapeutic drug target for diabetes and obesity.3) Therefore, PTP1B is a promising drug target for the treatment of T2D and obesity and is also involved in cancer. Although there have been a number of reports on the design and development of PTP1B inhibitors, new types of such compounds with suitable pharmacological properties remain to be discovered.The plant Aglaia abbreviata C. Y. WU (Meliaceae), which is a wild evergreen shrub found on mountain slopes at up to ca. 500-1600 m altitude, is widely distributed throughout southwestern China. 4) Members of the genus Aglaia have been studied extensively, resulting in the isolation of many types of interesting secondary metabolites, particularly of various triterpenoids (e.g., cycloartanes, dammaranes, tirucallanes) and flavaglines (e.g., cyclopenta [b] [8][9][10] In an ongoing research for biologically active substances from various natural sources, 11-15) the plant A. abbreviata attracted our attention because the ethyl acetate (EtOAc) extract of the leaves of this plant showed inhibitory activity against PTP1B with an 65.2% inhibition at the concentration of 20 µg/mL. A...

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confidence: 68%

“…On the other hand, obesity is one of the major risk factors for developing T2D due to insulin resistance. 1) Protein tyrosine phosphatases (PTPs) are responsible for the dephosphorylation of tyrosine residues and are considered negative regulators of insulin signaling.…”

mentioning

confidence: 99%

Aglaiabbrevins A–D, New Prenylated Bibenzyls from the Leaves of <i>Aglaia abbreviata</i> with Potent PTP1B Inhibitory Activity

Sun

Jiang

Zhang

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Polyphenols such as gallocatechin, epicatechin (Figure 2E), epigallocatechin, epigallocatechin gallate, marsupsine, and pterostilbene show an antidiabetic activity [83][84]. Some studies report that polyphenols reduce blood glucose [85].…”

Section: Phenolic Compoundsmentioning

confidence: 99%

Chemical and Biological Aspects of Extracts from Medicinal Plants with Antidiabetic Effects

Gushiken¹,

Beserra²,

Rozza³

et al. 2016

Rev Diabet Stud

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■ AbstractDiabetes mellitus is a chronic disease and a leading cause of death in western countries. Despite advancements in the clinical management of the disease, it is not possible to control the late complications of diabetes. The main characteristic feature of diabetes is hyperglycemia, which reflects the deterioration in the use of glucose due to a faulty or poor response to insulin secretion. Alloxan and streptozotocin (STZ) are the chemical tools that are most commonly used to study the disease in rodents. Many plant species have been used in ethnopharmacology or to treat experimentally symptoms of this disease. When evaluated pharmacologically, most of the plants employed as antidiabetic substances have been shown to exhibit hypoglycemic and antihyperglycemic activities, and to contain chemical constituents that may be used as new antidiabetic agents. There are many substances extracted from plants that offer antidiabetic potential, whereas others may result in hypoglycemia as a side effect due to their toxicity, particularly their hepatotoxicity. In this article we present an updated overview of the studies on extracts from medicinal plants, relating the mechanisms of action by which these substances act and the natural principles of antidiabetic activity.

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“…Two new merosesquiterpenes, verruculides A (1) and B (2), were isolated from a culture broth of the Indonesian ascidian-derived Penicillium verruculosum TPU1311, together with three known congeners, chrodrimanins A (3), B (4), and H (5). The structures of 1 and 2 were assigned on the basis of their spectroscopic data (1D and 2D NMR, HRMS, UV, CD, and IR).…”

Section: Introductionmentioning

confidence: 99%

Verruculides A and B, two new protein tyrosine phosphatase 1B inhibitors from an Indonesian ascidian-derived Penicillium verruculosum

Yamazaki

Nakayama

Takahashi

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Cited by 182 publications

References 208 publications

Aglaiabbrevins A–D, New Prenylated Bibenzyls from the Leaves of <i>Aglaia abbreviata</i> with Potent PTP1B Inhibitory Activity

Aglaiabbrevins A–D, New Prenylated Bibenzyls from the Leaves of <i>Aglaia abbreviata</i> with Potent PTP1B Inhibitory Activity

Chemical and Biological Aspects of Extracts from Medicinal Plants with Antidiabetic Effects

Verruculides A and B, two new protein tyrosine phosphatase 1B inhibitors from an Indonesian ascidian-derived Penicillium verruculosum

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