New sesquiterpenoids from the edible mushroom Pleurotus cystidiosus and their inhibitory activity against α-glucosidase and PTP1B

Tao, Qiaoqiao; Ma, Ke; Li, Bao; Wang, Kai; Han, Junjie; Zhang, Jinxia; Huang, Chenyang; Liu, Hongwei

doi:10.1016/j.fitote.2016.04.007

Cited by 26 publications

(8 citation statements)

References 22 publications

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“…Type II diabetes mellitus (T2DM) is a heterogeneous disease affecting over 100 million people worldwide, which accounts for about 90% of all cases of diabetes. , T2DM is a chronic metabolic disease featured by hyperglycemia and β-cell dysfunction which is mainly caused by insulin resistance. − Protein tyrosine phosphatase 1B (PTP1B), a key intracellular non-transmembrane enzyme linked to T2DM, works as a negative governor for the insulin signaling pathway by dephosphorylating both the insulin receptor and the downstream insulin receptor substrate proteins. − Research studies in PTP1B knockout rodents have indicated that the lack of the PTP1B gene could improve insulin sensitivity and help prevent diet-induced obesity without affecting normal growth and longevity. , These findings validated PTP1B as an attractive therapeutic target for the treatment of type II diabetes. Natural products with PTP1B inhibitory activity have been discovered in some plants and fungi. − Examples include styrastilbene B with IC 50 of 2.40 μM from Artocarpus styracifolius, lucidenic acid H and methyl lucidenate F with IC 50 of 18.1 and 28.1 μM from Ganoderma lucidum, clitocybulol L with IC 50 of 38.1 μM from Pleurotus cystidiosus, and erinacerin T with IC 50 of 24.9 μM from Hericium erinaceus. − However, there is still an urgent need to develop druggable PTP1B inhibitors with good cell permeability and specificity.…”

Section: Introductionmentioning

confidence: 99%

Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Fomitopsis pinicola Collected in North America

Zhang

Chen

Liang³

et al. 2020

J. Agric. Food Chem.

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A chemical investigation on the fruiting bodies of Fomitopsis pinicola led to the isolation and identification of 28 lanostane triterpenoids including 11 new compounds (1−11) and 17 known analogues (12−28). Their structures were elucidated by extensive one-dimensional NMR, two-dimensional NMR, and MS spectra. All isolates were tested for their anti-inflammatory activity, protein tyrosine phosphatase 1B (PTP1B) inhibitory activity in vitro, and effect on glucose uptake in insulin-resistant HepG2 cells. Compounds 1, 4, 22, 23, and 27 inhibited the nitric oxide released from the LPS-induced RAW 264.7 cell assay with IC 50 values in the range of 21.4−27.2 μM. Compounds 18, 22, 23, and 28 showed strong PTP1B inhibitory activity with IC 50 values in the range of 20.5−29.9 μM, comparable to that of the positive control of oleanolic acid (15.0 μM). Compounds 18 and 22 were confirmed to be good competitive inhibitors of PTP1B by kinetic analysis. In addition, compounds 18, 22, and 28 were found to stimulate glucose uptake in the insulin-resistant HepG2 cells in the dose from 6.25 to 100 μM. These findings indicated the potential of F. pinicola in the development of functional food or medicine for the prevention and treatment of diabetes.

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Section: Introductionmentioning

confidence: 99%

Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Fomitopsis pinicola Collected in North America

Zhang

Chen

Liang³

et al. 2020

J. Agric. Food Chem.

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“…Six sesquiterpenes were identified from the extracts of S. crispa , including clitocybulol C (peak 46) [76], 3β-hydroxy-11,12- O -isopropylidenedrimene (peak 47) [77], ustusol B (peak 56) [78], 3-(10-hydroxy-10-methylethyl)-5,8a-dimethyldecahydroazulen-4-ol (peak 109) [8], and (5β, 6α)-6,11-dihydroxyeudesmane (peak 110) [8]. As shown in Figure S3, in positive ESI mode, the protonated molecular ion of ainsliatone ( 3 , peak 25) [79] A was m / z 251.1277 [M + H] + , and its intramolecular dehydration produced the fragment ion m / z 233.1174 [M – 18 + H] + .…”

Section: Resultsmentioning

confidence: 99%

Rapid Characterization of Chemical Components in Edible Mushroom Sparassis crispa by UPLC-Orbitrap MS Analysis and Potential Inhibitory Effects on Allergic Rhinitis

et al. 2019

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Sparassis crispa is a kind of edible fungus widely grows in the north temperate zone, which shows various medicinal properties. Due to the complexity of chemical constitutes of this species, few investigations have acquired a comprehensive configuration for the chemical profile of it. In this study, a strategy based on ultra-high performance liquid chromatography (UPLC) combined with Orbitrap mass spectrometer (MS) was established for rapidly characterizing various chemical components in S. crispa. Through the summarized MS/MS fragmentation patterns of reference compounds and systematic identification strategy, a total of 110 components attributed to six categories were identified for the first time. Moreover, allergic rhinitis (AR) is a worldwide inflammatory disease seriously affecting human health, and the development of drugs to treat AR has been a topic of interest. It has been reported that the extracts of S. crispa showed obvious inhibitory effects on degranulation of mast cell- and allergen-induced IgE and proinflammatory mediators, but the active components and specific mechanism were still not clear. Src family kinases (SFKs) participate in the initial stage of allergy occurrence, which are considered the targets of AR treatment. Herein, on the basis of that self-built chemical database, virtual screening was applied to predict the potential SFKs inhibitors in S. crispa, using known crystal structures of Hck, Lyn, Fyn, and Syk as receptors, followed by the anti-inflammatory activity evaluation for screened hits by intracellular calcium mobilization assay. As results, sparoside A was directly confirmed to have strong anti-inflammatory activity with an IC50 value of 5.06 ± 0.60 μM. This study provides a useful elucidation for the chemical composition of S. crispa, and demonstrated its potential inhibitory effects on AR, which could promote the research and development of effective agents from natural resources.

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“…Clitocybulols G-O 10-18, highly oxidized alliacane sesquiterpenoids, were isolated from the solid culture of the edible fungus Pleurotus cystidiosus [17]. Clitocybulols G 10 and L 15 showed weak inhibitory activity against protein tyrosine phosphatase-1B (PTP1B) with IC 50 values of 49.5, 38.1 µM, respectively.…”

Section: Alliacane Cadinene Azulene and Zieranementioning

confidence: 99%

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

Quan

Zhang

Feng

2021

JoF

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Fungi are widely distributed in the terrestrial environment, freshwater, and marine habitat. Only approximately 100,000 of these have been classified although there are about 5.1 million characteristic fungi all over the world. These eukaryotic microbes produce specialized metabolites and participate in a variety of ecological functions, such as quorum detection, chemical defense, allelopathy, and maintenance of symbiosis. Fungi therefore remain an important resource for the screening and discovery of biologically active natural products. Sesquiterpenoids are arguably the richest natural products from plants and micro-organisms. The rearrangement of the 15 high-ductility carbons gave rise to a large number of different skeletons. At the same time, abundant structural variations lead to a diversification of biological activity. This review examines the isolation, structural determination, bioactivities, and synthesis of sesquiterpenoids that were specially produced by fungi over the past five years (2015–2020).

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New sesquiterpenoids from the edible mushroom Pleurotus cystidiosus and their inhibitory activity against α-glucosidase and PTP1B

Cited by 26 publications

References 22 publications

Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Fomitopsis pinicola Collected in North America

Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Fomitopsis pinicola Collected in North America

Rapid Characterization of Chemical Components in Edible Mushroom Sparassis crispa by UPLC-Orbitrap MS Analysis and Potential Inhibitory Effects on Allergic Rhinitis

Sesquiterpenoids Specially Produced by Fungi: Structures, Biological Activities, Chemical and Biosynthesis (2015–2020)

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