Sesquiterpenoids with PTP1B Inhibitory Activity and Cytotoxicity from the Edible Mushroom Pleurotus citrinopileatus

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

doi:10.1055/s-0041-111629

Cited by 31 publications

(17 citation statements)

References 22 publications

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“…Frondoplysin B (2), isomeric with 1, has the same molecular formula of C 42 H 49 O 9 N 3 Br 4 as assigned by the 13 C NMR data and HRMS ion at m/z 1078.0101 [M + Na] + . The NMR data (Table S2) of 2 highly resembled those of 1 except for the disappearance of the exomethylene protons at δ H 4.46 and 4.45 and the appearance of an olefinic singlet at δ H 5.15, indicating the exocyclic double bond Δ 4,11 in 1 was transferred to Δ 3,4 in 2.…”

mentioning

confidence: 83%

“…Protein-tyrosine phosphatase 1B (PTP1B) has been known as a negative regulator for insulin and leptin receptor signaling for a long time, , and an increasing number of inhibitors targeting PTP1B have been discovered and developed. − Recently, PPT1B was found to be aberrantly expressed in some cancer cells; moreover, it could function as an important oncogene closely related to breast cancer progression . In our ongoing discovery program for PTP1B inhibitors from marine sponges, , we analyzed a collection of sponge specimens from the South China Sea using the LCMS method in conjunction with the PTP1B inhibitory screening assay.…”

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confidence: 99%

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Frondoplysins A and B, Unprecedented Terpene-Alkaloid Bioconjugates from Dysidea frondosa

Lin

Zhang

et al. 2019

Org. Lett.

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The chemical investigation of the marine sponge Dysidea frondosa discovered a pair of unprecedented bioconjugates that are composed of a meroterpene and an unusual psammaplysin alkaloid. The structures of frondoplysins A (1) and B (2) were characterized by analysis of HRMS and NMR data coupled with single-crystal X-ray diffraction. Frondoplysin A was found to be a potent inhibitor targeting protein-tyrosine phosphatase 1B (PTP1B) with an IC50 value of 0.39 μM.

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confidence: 83%

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confidence: 99%

Frondoplysins A and B, Unprecedented Terpene-Alkaloid Bioconjugates from Dysidea frondosa

Lin

Zhang

et al. 2019

Org. Lett.

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“…Sporulaminals A 40 and B 41, a pair of unusual epimeric spiroaminal derivatives bearing a 6/4/5/5 tetracyclic ring system derived from bergamotane sesquiterpenoid (Scheme 2), were isolated from a marine-derived fungus Paraconiothyrium sporulosum [32]. Pleurospiroketal F 42, a new perhydrobenzannulated 5,5-spiroketal sesquiterpene was isolated from solid-state fermentation of Pleurotus citrinopileatus, and the absolute configuration of 42 was determined by single-crystal X-ray diffraction analysis [33].…”

Section: Bergamotane Spiroaminal and Spiroaxanementioning

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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“…Terpenoids as organic compounds distribute in plants, animals and marine life. They significantly inhibited the activity of PTP1B (PTP1B) [53][54][55][56]. In addition, PTP1B inhibitory activity were also showed in proteoglycan, quinolone, steroids, containing nitrogen or sulfur compounds for anti-diabets [57][58][59].…”

Section: Natural Molecules As Ptp1b Inhibitor and Therapy Of Type 2 Dmentioning

confidence: 99%

Type 2 Diabetes Mellitus and Protein-Tyrosine Phosphatase 1B1

Zou¹

2016

JDMDC

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Diabetes is one of the common metabolic diseases, mainly divided into two types, type 1 diabetes mellitus and type 2 diabetes mellitus. Insulin resistance is the main performance of type 2 diabetes mellitus which are relative to some gene mutation, genetics, obesity and so on. Protein-tyrosine phosphatase 1B (PTP1B) plays an important role as a negative regulator in insulin signaling pathways that are implicated in metabolic diseases such as obesity and type 2 diabetes. Many evidences from clinical and basical reseach shows that the high expression of PTP1B induces insulin resistance and PTP1B is an effective target for the treatment of type 2 diabetes mellitus. In this review, we briefly introduce composition of PTP1B, and then examine the role of PTP1B in insulin signaling of type 2 diabets mellitus. Finally, we highlight the recent research progress of PTP1B inhibitors used in therapy of type 2 diabetes mellitus. medications such as oxidation, nitrosyaltion, sulfyhydration, sumoylation, phosphorylation and proteolytic cleavage. The diverse modifications illustrated the dynamic regulation of this enzyme and its ability to modulate numerous signaling pathways likely in a cell/tissue-and stimulus-dependent manner, with high specificity and precision. PTP1B, as a potential target for type2 diabetes and obesity, have expanded out of PTP1B gene cDNA span [11]. At the same time, the molecular dynamics studies of interaction between PTP1B and its inhibitors are also going on [12], all which lay a foundation for screening specific PTP1B inhibitors. Keywords: The role of PTP1B in insulin signaling of type 2 diabetes mellitusThe pathogenesis of type 2 diabetes are associated with gene mutation, heredity, obesity and other factors, which main performance is insulin resistance. Dysfunction of pancreatic β cells is one of basic processes and characteristic of the pathogenesis. The increased prevalence of this disease highlights the urgent need to elucidate the underlying molecular mechanisms to aid in therapeutic intervention. Insulin secreted from pancreatic β cells acts as a major regulator of glucose homeostasis through a complex and integrated signaling network. Insulin receptor is a kind of transmembrane glycoprotein complex molecules, consisting of two alpha and beta subunits by three disulfide bond connection, among which the alpha subunits locate in the lateral of the cell and beta subunits are across the cell membrane. Insulin binding alpha subunits of the receptor induced phosphorylation of tyrosine residues and protein tyrosine kinase (PTK) of beta subunits, and resulted in a series of phosphorylation and dephosphorylation cascade reactions including mitogen-activated protein kinases (MAPK) and PI3K/Akt signal pathways to regulate metabolism. Whereas, when the concentration of insulin is beyond the physiological concentration (hyperinsulinemia), insulin promoted cell proliferation and developments, which may due to the combination of insulin with insulin-like growth factor 1 receptor (IGF-1R) or insulin-...

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Sesquiterpenoids with PTP1B Inhibitory Activity and Cytotoxicity from the Edible Mushroom Pleurotus citrinopileatus

Cited by 31 publications

References 22 publications

Frondoplysins A and B, Unprecedented Terpene-Alkaloid Bioconjugates from Dysidea frondosa

Frondoplysins A and B, Unprecedented Terpene-Alkaloid Bioconjugates from Dysidea frondosa

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

Type 2 Diabetes Mellitus and Protein-Tyrosine Phosphatase 1B1

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