Natamycin - 10mM in DMSO , Ergosterol sequestering agent, CAS No.7681-93-8, Ergosterol sequestering agent

CAS: 7681-93-8 Cat. No.: N409156 Formula: C₃₃H₄₇NO₁₃ Peso molecolare: 665.73 Beilstein Registry Number: 1614878 Numero EC: 231-683-5

GRADE & PURITY 10mM in DMSO

Synonyms

Pimaricin | (1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-22-[(3-Amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Information

Natamycin Natamycin (Pimaricin), a natural and versatile anti-fungal agent during fermentation by the bacterium Streptomyces natalensis, commonly found in soil; with little to no flavour interference
In vitro

Natamycin binds specifically to ergosterol present in model membranes. Natamycin does not change the permeability of the yeast plasma membrane under conditions that growth is blocked. Natamycin blocks the fusion of isolated vacuoles without compromising the barrier function of the vacuolar membrane. Natamycin perturbs the cellular vacuole morphology, causing the formation of many more small vacuolar structures in yeast cells. Natamycin inhibits the priming stage of vacuole fusion. Natamycin shows low MIC against the dematiaceous fungi, Curvularia species. Natamycin is complexed with gamma-cyclodextrin (NT-gamma CyD) to increase the solubility and stability of NT in aqueous solutions and reduce the side effects of the drug without decreasing antimycotic activity. MIC90 of Natamycin alone and Natamycin-gamma CyD complexes are below 0.0313 mg/mL, suggesting that complexation with gamma CyD has effectively increased the antimycotic activity of Natamycin, thus indicating the clinical usefulness of Natamycin-gamma CyD complexes.

In vivo

Cell Data

cell lines：

Concentrations：

Incubation Time：

Powder Purity:≥98%

Specifications

Sinonimi

Pimaricin | (1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-22-[(3-Amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Natamycin (Pimaricin), a natural and versatile anti-fungal agent during fermentation by the bacterium Streptomyces natalensis, commonly found in soil; with little to no flavour interference

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Tipo di azione

SEQUESTERING AGENT

Meccanismo d'azione

Ergosterol sequestering agent

Nomi e identificatori

• Isomeri SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
• WGK Germania: 3
• RTECS: TK3325000
• Peso molecolare: 665.73
• Beilstein: 1614878
• Reaxy-Rn: 25144604
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25144604&ln=

Proprietà chimiche e fisiche

• Punto di infiammabilità (°C): >110°C
• Punto di ebollizione (°C): 952°C
• Punto di fusione (°C): 280°C（分解）

Riferimenti

1. Chaoyi Shen, Xiangzheng Yang, Da Wang, Jiangkuo Li, Changqing Zhu, Di Wu, Kunsong Chen.  (2023)  Carboxymethyl chitosan and polycaprolactone-based rapid in-situ packaging for fruit preservation by solution blow spinning.  CARBOHYDRATE POLYMERS,      [PMID:38142080] [10.1016/j.carbpol.2023.121636]

2. Xiangzheng Yang, Jingshan Rao, Chaoyi Shen, Huan Lian, Da Wang, Di Wu, Kunsong Chen.  (2023)  Natamycin-Loaded Ethyl Cellulose/PVP Films Developed by Microfluidic Spinning for Active Packaging.  Foods,  13  (1): (132).  [PMID:38201160] [10.3390/foods13010132]

3. Yuxuan Cao, Xu Zhang, Xiaoning Song, Wenkui Li, Zheng Ren, Juntao Feng, Zhiqing Ma, Xili Liu, Yong Wang.  (2023)  Efficacy and toxic action of the natural product natamycin against Sclerotinia sclerotiorum.  PEST MANAGEMENT SCIENCE,      [PMID:38087429] [10.1002/ps.7930]

4. Mengying Sun, Jiang Yu, Yinglong Song, Xinling Li, Guangqing Mu, Yanfeng Tuo.  (2023)  Fermented milk by Lactobacillus delbrueckii, Lacticaseibacillus paracasei, and Kluyveromyces marxianus shows special physicochemical and aroma formation during the storage.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2023.103025]

5. Saichao Wei, Jun Mei, Jing Xie.  (2021)  Effects of Edible Coating and Modified Atmosphere Technology on the Physiology and Quality of Mangoes after Low-Temperature Transportation at 13 °C in Vibration Mitigation Packaging.  Plants-Basel,  10  (11): (2432).  [PMID:34834795] [10.3390/plants10112432]

6. Chaoyi Shen, Yang Cao, Jingshan Rao, Yucheng Zou, Hui Zhang, Di Wu, Kunsong Chen.  (2021)  Application of solution blow spinning to rapidly fabricate natamycin-loaded gelatin/zein/polyurethane antimicrobial nanofibers for food packaging.  Food Packaging and Shelf Life,      [PMID:] [10.1016/j.fpsl.2021.100721]

7. Xiaopeng Yang, Xiang Yu, Yan Heng, Fei Wang.  (2018)  Facile fabrication of 3D graphene–multi walled carbon nanotubes network and its use as a platform for natamycin detection.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2018.03.029]

8. Han Wu, Xin Rui, Wei Li, Yu Xiao, Jianzhong Zhou, Mingsheng Dong.  (2018)  Whole-grain oats (Avena sativa L.) as a carrier of lactic acid bacteria and a supplement rich in angiotensin I-converting enzyme inhibitory peptides through solid-state fermentation.  Food & Function,  9  (4): (2270-2281).  [PMID:29560488] [10.1039/C7FO01578J]

9. Tan-Jun Wang, Yi-Ming Shan, Han Li, Wei-Wang Dou, Xin-Hang Jiang, Xu-Ming Mao, Shui-Ping Liu, Wen-Jun Guan, Yong-Quan Li.  (2016)  Multiple transporters are involved in natamycin efflux in Streptomyces chattanoogensis L10.  MOLECULAR MICROBIOLOGY,  103  (4): (713-728).  [PMID:27874224] [10.1111/mmi.13583]

10. Miaomiao Tian, Yongcun Zou, Shaoyan Zhou, Tianpeng Wang, Xueju Lv, Qiong Jia.  (2015)  Development of novel magnetic solid phase extraction materials based on Fe3O4/SiO2/poly(acrylamide-N,N′-methylene bisacrylamide)-Pluronic L64 composite microspheres and their application to the enrichment of natamycin.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:26554702] [10.1016/j.jchromb.2015.09.042]

11. Xinwen Dong, Yaguang Su, Zheng Luo, Cuiying Li, Jie Gao, Xiaofeng Han, Sanqiao Yao, Weidong Wu, Linqiang Tian, Yichun Bai, Guizhi Wang, Wenjie Ren.  (2024)  Fecal microbiota transplantation alleviates cognitive impairment by improving gut microbiome composition and barrier function in male rats of traumatic brain injury following gas explosion.  Frontiers in Microbiology,      [PMID:39552646] [10.3389/fmicb.2024.1485936]

Domande frequenti

How should this product be stored?

Store at ?80 °C. Ultra-low temperature storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 7681-93-8, the molecular formula is C33H47NO13, and the molecular weight is 665.73 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.