Sydowinin B
(Synonyms: MS-347b) 目录号 : GC48764
A xanthone polyketide with immunosuppressant activity
Cas No.:58450-00-3
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Sydowinin B is a xanthone polyketide that has been found in A. sydowii and has immunosuppressant activity.1 It inhibits LPS- or concanavalin A-induced proliferation of isolated mouse splenic lymphocytes (IC50s = 19.2 and 20.8 µg/ml, respectively).2 Sydowinin B inhibits superoxide generation in, and elastase release from, isolated human neutrophils induced by cytochalasin B and N-Formyl-Met-Leu-Phe with IC50 values of 21.2 and 12.62 µM, respectively.3
1.Hamasaki, T., Sato, Y., and Hatsuda, Y.Structure of sydowinin A, sydowinin B, and sydowinol, metabolites from Aspergillus sydowiAgr. Biol. Chem.39(12)2341-2345(1975) 2.Liu, H., Chen, S., Liu, W., et al.Polyketides with immunosuppressive activities from mangrove endophytic fungus Penicillium sp. ZJ-SY2Mar. Drugs14(12)217(2016) 3.Chung, Y.-M., Wei, C.-K., Chuang, D.-W., et al.An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowiiBioorg. Med. Chem.21(13)3866-3872(2013)
| Cas No. | 58450-00-3 | SDF | |
| 别名 | MS-347b | ||
| Canonical SMILES | O=C(C(C(O)=CC=C1OC2=CC(CO)=CC(O)=C23)=C1C3=O)OC | ||
| 分子式 | C16H12O7 | 分子量 | 316.3 |
| 溶解度 | 储存条件 | -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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.1616 mL | 15.8078 mL | 31.6156 mL |
| 5 mM | 0.6323 mL | 3.1616 mL | 6.3231 mL |
| 10 mM | 0.3162 mL | 1.5808 mL | 3.1616 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。
Total syntheses of graphisin A and Sydowinin B
Org Lett 2012 Jun 1;14(11):2862-5.PMID:22621405DOI:10.1021/ol301107m.
Efficient syntheses of the highly substituted benzophenone graphisin A and the xanthone Sydowinin B are described. Key steps involve aryl anion addition to substituted benzaldehyde derivatives, subsequent methyl ester installation, and dehydrative cyclization. Oxidation of graphisin A led to a spirodienone derived from a highly substituted benzoquinone intermediate.
α-Glucosidase and PTP-1B Inhibitors from Malbranchea dendritica
ACS Omega 2021 Aug 25;6(35):22969-22981.PMID:34514267DOI:10.1021/acsomega.1c03708.
An extract from a PDB static culture of Malbranchea dendritica exhibited α-glucosidase and PTP-1B inhibitory activities. Fractionation of the active extract led to the isolation of gymnoascolide A (1), a γ-butenolide, and xanthones sydowinin A (2), Sydowinin B (3), and AGI-B4 (4), as well as orcinol (5). Compound 1 exhibited important inhibitory activity against yeast α-glucosidase (IC50 = 0.556 ± 0.009 mM) in comparison to acarbose (IC50 = 0.403 ± 0.010 mM). Kinetic analysis revealed that 1 is a mixed-type inhibitor. Furthermore, compound 1 significantly reduced the postprandial peak in mice during a sucrose tolerance test at the doses of 5.16 and 10 mg/kg. Compound 1 was reduced with Pd/C to yield a mixture of enantiomers 1a and 1b; the mixture showed similar activity against α-glucosidase (IC50 = 0.396 ± 0.003 mM) and kinetic behavior as the parent compound but might possess better drug-likeness properties according to SwissADME and Osiris Property Explorer tools. Docking analysis with yeast α-glucosidase (pdb: 3A4A) and the C-terminal subunit of human maltase-glucoamylase (pdb: 3TOP) predicted that 1, 1a, and 1b bind to an allosteric site of the enzymes. Compounds 1-5 were evaluated against PTP-1B, but only xanthone 3 moderately inhibited in a noncompetitive fashion the enzyme with an IC50 of 0.081 ± 0.004 mM. This result was consistent with that of docking analysis, which revealed that 3 might bind to an allosteric site of the enzyme. From the inactive barley-based semisolid culture of M. dendritica, the natural pigment erythroglaucin (6) and the nucleosides deoxyadenosine (7), adenosine (8), thymidine (9), and uridine (10) were also isolated and identified.
Combined Cytotoxicity of the Phycotoxin Okadaic Acid and Mycotoxins on Intestinal and Neuroblastoma Human Cell Models
Toxins (Basel) 2018 Dec 8;10(12):526.PMID:30544794DOI:10.3390/toxins10120526.
Mycotoxins are emerging toxins in the marine environment, which can co-occur with algal toxins to exert synergistic or antagonistic effects for human seafood consumption. The current study assesses the cytotoxicity of the algal toxin okadaic acid, shellfish, and dust storm-associated mycotoxins alone or in combination on human intestinal (HT-29) and neuroblastoma (SH-SY5Y) cell lines. Based on calculated IC50 (inhibitory concentration 50%) values, mycotoxins and the algal toxin on their own exhibited increased cytotoxicity in the order of sydowinin A < Sydowinin B << patulin < alamethicin < sydowinol << gliotoxin ≈ okadaic acid against the HT-29 cell line, and Sydowinin B < sydowinin A << alamethicin ≈ sydowinol < patulin, << gliotoxin < okadaic acid against the SH-SY5Y cell line. Combinations of okadaic acid⁻sydowinin A, ⁻alamethicin, ⁻patulin, and ⁻gliotoxin exhibited antagonistic effects at low-moderate cytotoxicity, but became synergistic at high cytotoxicity, while okadaic acid⁻sydowinol displayed an antagonistic relationship against HT-29 cells. Furthermore, only okadaic acid⁻sydowinin A showed synergism, while okadaic acid⁻sydowinol, ⁻alamethicin, ⁻patulin, and ⁻gliotoxin combinations demonstrated antagonism against SH-SY5Y. While diarrhetic shellfish poisoning (DSP) from okadaic acid and analogues in many parts of the world is considered to be a comparatively minor seafood toxin syndrome, our human cell model studies suggest that synergisms with certain mycotoxins may aggravate human health impacts, depending on the concentrations. These findings highlight the issues of the shortcomings of current regulatory approaches, which do not regulate for mycotoxins in shellfish and treat seafood toxins as if they occur as single toxins.
High-performance liquid chromatography comparison of supercritical-fluid extraction and solvent extraction of microbial fermentation products
J Chromatogr A 1995 Apr 21;697(1-2):115-22.PMID:7780576DOI:10.1016/0021-9673(94)00817-s.
The use of supercritical fluids for the extraction of biologically active compounds from the biomass of microbial fermentations has been compared with extraction using the organic solvents methanol and dichloromethane. Compounds representing a range of structural types were selected for investigation. All the extracts obtained were examined using reversed-phase high-performance liquid chromatography. The extractability of metabolites using unmodified and methanol-modified supercritical-fluid carbon dioxide was examined in particular detail for six microbial metabolites: chaetoglobosin A, mycolutein, luteoreticulin, 7,8-dihydro-7,8-epoxy-1-hydroxy-3-hydroxymethyl-xanthone-8-carboxyl ic acid methyl ester, Sydowinin B and elaiophylin. The extraction strength of supercritical-fluid carbon dioxide alone appeared to be lower than that of dichloromethane. All the components of interest that were extractable with dichloromethane and methanol were also extractable with methanol-modified carbon dioxide.