Sorbicillin
目录号 : GC67796Sorbicillin，一种山梨霉素类似物，是一种有效的抗炎剂 (anti-inflammation agent)。
Cas No.:79950-85-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Sorbicillin, a sorbicillinoid analogue, acts as a potent anti-inflammation agent[1].
[1]. Meng Zhang, et al. Synthesis of sorbicillinoid analogues with anti-inflammation activities. Bioorg Med Chem. 2022 Jan 15;54:116589
| Cas No. | 79950-85-9 | SDF | Download SDF |
| 分子式 | C14H16O3 | 分子量 | 232.28 |
| 溶解度 | DMSO : 100 mg/mL (430.51 mM; ultrasonic and warming and heat to 60°C) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.3051 mL | 21.5257 mL | 43.0515 mL |
| 5 mM | 0.861 mL | 4.3051 mL | 8.6103 mL |
| 10 mM | 0.4305 mL | 2.1526 mL | 4.3051 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Mechanism and regulation of Sorbicillin biosynthesis by Penicillium chrysogenum
Microb Biotechnol 2017 Jul;10(4):958-968.PMID:28618182DOI:10.1111/1751-7915.12736.
Penicillium chrysogenum is a filamentous fungus that is used to produce β-lactams at an industrial scale. At an early stage of classical strain improvement, the ability to produce the yellow-coloured sorbicillinoids was lost through mutation. Sorbicillinoids are highly bioactive of great pharmaceutical interest. By repair of a critical mutation in one of the two polyketide synthases in an industrial P. chrysogenum strain, sorbicillinoid production was restored at high levels. Using this strain, the Sorbicillin biosynthesis pathway was elucidated through gene deletion, overexpression and metabolite profiling. The polyketide synthase enzymes SorA and SorB are required to generate the key intermediates Sorbicillin and dihydrosorbicillin, which are subsequently converted to (dihydro)sorbillinol by the FAD-dependent monooxygenase SorC and into the final product oxosorbicillinol by the oxidoreductase SorD. Deletion of either of the two pks genes not only impacted the overall production but also strongly reduce the expression of the pathway genes. Expression is regulated through the interplay of two transcriptional regulators: SorR1 and SorR2. SorR1 acts as a transcriptional activator, while SorR2 controls the expression of sorR1. Furthermore, the sorbicillinoid pathway is regulated through a novel autoinduction mechanism where sorbicillinoids activate transcription.
Antibacterial Sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza
Chin J Nat Med 2018 May;16(5):358-365.PMID:29860997DOI:10.1016/S1875-5364(18)30068-2.
One new Sorbicillin derivative, 2-deoxy-sohirnone C (1), one new diketopiperazine alkaloid, 5S-hydroxynorvaline-S-Ile (2), and two naturally occurring diketopiperazines, 3S-hydroxylcyclo(S-Pro-S-Phe) (3) and cyclo(S-Phe-S-Gln) (4), together with three known compounds were isolated from the Chinese mangrove endophytic fungus Penicillium sp. GD6. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison with literature data. The absolute configuration of 3-hydroxyl moiety in 3 was determined by Mosher's method, while the absolute stereochemistry of 2 and 4 was established by comparison with the CD spectra of natural and synthesized diketopiperazines. Compound 1 showed moderate antibacterial activity against Methicillin-resistant Staphylococcus aureus with a MIC value of 80 μg·mL-1.
Investigation of the neuroprotective and neuritogenic effects of halotolerant Penicillium flavigenum-derived sorbicillin-like compounds on PC-12 Adh cells
Cytotechnology 2021 Dec;73(6):801-813.PMID:34776630DOI:10.1007/s10616-021-00498-9.
Parkinson's disease (PD) is an adult-onset neurodegenerative condition caused by oxidative stress and mitochondrial malfunction. In this study, the neuroprotective and neuritogenic activity of water fraction (Sw-fr) containing sorbicillin-like active metabolites of halotolerant P. flavigenum isolated from Salt Lake in Konya, Turkey were investigated on a 6-hydroxydopamine (6-OHDA)-induced PD in vitro PC-12 Adh cell model. Firstly, Sw-fr containing sorbicillin-like active metabolites were extracted from P. flavigenum and was compared with a Sorbicillin standard by liquid chromatography-mass spectrometry (LC-MS). Then, the effects of non-cytotoxic concentrations of Sw-fr on the 6-OHDA-induced PD cell model were investigated via real-time cell proliferation analysis using the RTCA DP instrument. The effects of these concentrations on mitochondrial membrane integrity, caspase-3 were investigated by flow cytometry. Neurite outgrowth analysis and immunofluorescence staining were used to explore the neuritogenic effects of neuroprotective doses. By improving PC-12 Adh cell viability, decreasing reactive oxygen species production, and reducing apoptotic cell death, 1 and 10 μg/mL Sw-fr and Sorbicillin standard proved neuroprotective against 6-OHDA-induced neurotoxicity. Furthermore, 1 and 10 µg/mL Sw-fr significantly induced neurite outgrowth. As a result, sorbicillin-like active metabolites containing Sw-fr were found to have neuroprotective and neuritogenic effects. Sorbicillin-like metabolites obtained from fungi may be novel natural medicines for neurodegenerative diseases. Supplementary information: The online version contains supplementary material available at 10.1007/s10616-021-00498-9.
Sorbicillin analogues and related dimeric compounds from Penicillium notatum
J Nat Prod 2005 Jun;68(6):865-70.PMID:15974609DOI:10.1021/np040137t.
In our screening of microorganisms for new natural products, the fungus Penicillium notatum delivered further members of the Sorbicillin family, namely, the sohirnones A [3, 1-(2,4-dihydroxy-5-methylphenyl)hex-4-en-1-one], B [4a, 1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hexa-2,4-dien-1-one], and C [5, 1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hex-4-en-1-one]. A stable tautomer of oxosorbicillinol (7) was characterized as 6, and the recently described 7-deacetoxyyanuthone (8) was reisolated. The additionally isolated rezishanones A-D (12-13c) are the first natural Diels-Alder products of sorbicillinol (1) with dienophiles not related with 1. The monomers and dimers showed weak antibacterial activity, but were inactive against fungi and algae. The structures were determined by spectroscopic methods and by comparison of the NMR data with those of the structurally related 2',3'-dihydrosorbicillin (2) and, in the case of 4a, by transformation into the known sorrentanone (4b).
Two acid Sorbicillin analogues from saline lands-derived fungus Trichoderma sp
J Antibiot (Tokyo) 2011 Sep;64(9):645-7.PMID:21772303DOI:10.1038/ja.2011.54.
Two new acid Sorbicillin analogues, (E)-6-(2,4-dihydroxyl-5-methylphenyl)-6-oxo-2-hexenoic acid (1) and 6-(2,4-dihydroxyl-5-methylphenyl)-6-oxohexanoic acid (2), together with 12 known compounds, were isolated from a saline lands-derived fungus Trichoderma sp. The structures of the new compounds were established by interpretation of their spectroscopic data. Their cytotoxic effects on P388 and HL-60 cell lines were preliminarily evaluated by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide (MTT) method. Furthermore, the new compounds exhibited weak radical scavenging activity against DPPH (1,1-diphenyl-2-picrylhydrazyl).