Polyozellin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02047 |
| CAS | 197703-46-1 |
| Molecular Weight | 438.34 |
| Molecular Formula | C22H14O10 |
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Description
Polyozellin is a prolyl endopeptidase inhibitor produced by Polyozellin multiplex.
Specification
| IUPAC Name | (12-acetyloxy-6,7,16,17-tetrahydroxy-10,20-dioxapentacyclo[11.7.0.03,11.04,9.014,19]icosa-1,3(11),4,6,8,12,14,16,18-nonaen-2-yl) acetate |
| Canonical SMILES | CC(=O)OC1=C2C(=C(C3=C1C4=CC(=C(C=C4O3)O)O)OC(=O)C)C5=CC(=C(C=C5O2)O)O |
| InChI | InChI=1S/C22H14O10/c1-7(23)29-19-17-9-3-11(25)13(27)5-15(9)32-22(17)20(30-8(2)24)18-10-4-12(26)14(28)6-16(10)31-21(18)19/h3-6,25-28H,1-2H3 |
| InChI Key | CCNILPFRYYKQOP-UHFFFAOYSA-N |
Properties
| Boiling Point | 520.1±45.0°C at 760 mmHg |
| Melting Point | >245°C (dec.) |
| Density | 1.7±0.1 g/cm3 |
Reference Reading
1. Suppressive effects of polyozellin on endothelial protein C receptor shedding via inhibiting TACE activity and MAP kinases
Wonhwa Lee, Eun-Ju Yang, Dong Ho Park, Jong-Sup Bae Fitoterapia. 2016 Jan;108:26-32. doi: 10.1016/j.fitote.2015.11.005. Epub 2015 Nov 14.
Beyond its role in the activation of protein C, the endothelial cell protein C receptor (EPCR) plays an important role in the cytoprotective pathway. EPCR can be shed from the cell surface, which is mediated by tumor necrosis factor-α converting enzyme (TACE). Polyozellin, a major constituent of a Korea edible mushroom Polyozellus multiplex, has been known to exhibit the biological activities such as anti-oxidative and anti-inflammatory effects. However, little is known about the effects of polyozellin on EPCR shedding. We investigated this issue by monitoring the effects of polyozellin on phorbol-12-myristate 13-acetate (PMA)-, tumor necrosis factor (TNF)-α-, interleukin (IL)-1β-induced EPCR shedding in human umbilical vein endothelial cells (HUVECs), and cecal ligation and puncture (CLP)-mediated EPCR shedding in mice and underlying mechanism. Data demonstrate that polyozellin induced potent inhibition of PMA-, TNF-α-, IL-1β- (in HUVECs), and CLP-induced EPCR shedding (in mice) via inhibition of phosphorylation of mitogen-activated protein kinases (MAPKs) such as p38, janus kinase (JNK), and extracellular signal-regulated kinase (ERK) 1/2. Polyozellin also inhibited the expression and activity of PMA-induced TACE in HUVECs suggesting that p38, ERK1/2, and JNK could be the molecular targets of POZ. These results demonstrate the potential of polyozellin as an anti-EPCR shedding reagent against PMA-mediated and CLP-mediated EPCR shedding.
2. Synthesis of polyozellin, a prolyl oligopeptidase inhibitor, and its structural revision
Shunya Takahashi, Takahiro Kawano, Natsumi Nakajima, Yasuaki Suda, Narandulam Usukhbayar, Ken-Ichi Kimura, Hiroyuki Koshino Bioorg Med Chem Lett. 2018 Mar 1;28(5):930-933. doi: 10.1016/j.bmcl.2018.01.054. Epub 2018 Jan 31.
Polyozellin is a p-terphenyl compound which was isolated from Polyozellus multiplex, and exhibits an inhibitory activity against prolyl oligopeptidase (POP). Its structure was assigned as 1 having a p-terphenyl skeleton including a p-substituted dibenzofuran moiety by spectroscopic analyses and chemical means. This paper describes the total syntheses of the proposed structure 1 for polyozellin and its o-isomer 2, revising the structure of polyozellin to the latter. These syntheses involved a double Suzuki-Miyaura coupling using chlorophenylboronic acid as a common key building block, and Cu mediated Ullmann cyclization as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated.
3. Polyozellin alleviates atopic dermatitis-like inflammatory and pruritic responses in activated keratinocytes and mast cells
Na-Hee Jeong, Soyoung Lee, Jin Kyeong Choi, Young-Ae Choi, Min-Jong Kim, Hyun-Shik Lee, Tae-Yong Shin, Yong Hyun Jang, Kyung-Sik Song, Sang-Hyun Kim Biomed Pharmacother. 2020 Feb;122:109743. doi: 10.1016/j.biopha.2019.109743. Epub 2019 Dec 30.
Polyozellus multiplex is an edible mushroom that offers beneficial pharmacological effects against intestinal inflammation and cancer. Previous studies have demonstrated that polyozellin, a major component of P. multiplex, has therapeutic activities against inflammation, cancer, and oxidative stress-related disorders. This study aimed to determine the pharmacological effects of polyozellin on inflammatory and pruritic responses, the major symptoms of atopic dermatitis (AD), and to define its underlying mechanism of action. Our results showed that polyozellin inhibited the expression of inflammatory cytokines and chemokines through blockade of signal transducer and activator of transcription 1 and nuclear factor-κB in activated keratinocytes, the major cells involved in AD progression. Based on the histological and immunological analyses, oral treatment with polyozellin attenuated the Dermatophagoides farinae extract (DFE)/2,4-dinitrochlorobenzene (DNCB)-induced atopic inflammatory symptoms in the skin. Pruritus is an unpleasant sensation for AD patients that causes scratching behavior and ultimately exacerbates the severity of AD. To find a possible explanation for the anti-pruritic effects of polyozellin, we investigated its effects on mast cells and mast cell-derived histamines. Oral treatment with polyozellin reduced the DFE/DNCB-induced tissue infiltration of mast cells, the serum histamine levels, and the histaminergic scratching behaviors. Additionally, polyozellin decreased the immunoglobulin E-stimulated degranulation of mast cells. Taken together, the findings of this study provide us with novel insights into the potential pharmacological targets of polyozellin for treating AD by inhibiting the inflammatory and pruritic responses.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
