Deoxyfusapyrone
目录号 : GC41092
A fungal metabolite with antifungal activity
Cas No.:156856-32-5
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: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Deoxyfusapyrone is an α-pyrone fungal metabolite originally isolated from F. semitectum and has antifungal activity. It is active against C. neoformans, A. fumigatus, A. niger, and A. flavus human mycoses (MICs = 1.56-6.25 μg/ml). Deoxyfusapyrone is also active against a variety of filamentous fungi, but not yeast or the bacterium B. megaterium, in a disc assay.
| Cas No. | 156856-32-5 | SDF | |
| Canonical SMILES | O[C@H]1C[C@@H](CO)O[C@@H](C2=C(O)OC(C(C)(C)C(O)/C=C/C(C)=C/C(C)/C=C(C)\CC(C)CCCCCC)=CC2=O)[C@@H]1O | ||
| 分子式 | C34H54O8 | 分子量 | 590.8 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 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。 |
||
| 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 | 1.6926 mL | 8.4631 mL | 16.9262 mL |
| 5 mM | 0.3385 mL | 1.6926 mL | 3.3852 mL |
| 10 mM | 0.1693 mL | 0.8463 mL | 1.6926 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。
The synthesis of Deoxyfusapyrone. 1. An approach to the pyrone moiety
J Org Chem 2002 Nov 1;67(22):7847-51.PMID:12398512DOI:10.1021/jo0204707.
An effective synthesis of the C1-C10 component of Deoxyfusapyrone has been achieved that will allow for the synthesis of both the (R) and (S) form of the C-8 chiral center starting from optically pure (+)- and (-)-3,3-dimethyl-2-hydroxy-gammalactone (pantolactone).
Fusapyrone and Deoxyfusapyrone, two antifungal alpha-pyrones from Fusarium semitectum
Nat Toxins 1994;2(1):4-13.PMID:8032694DOI:10.1002/nt.2620020103.
A strain of Fusarium semitectum Berk. & Rav. from maize stalk rot in southern Italy produced bioactive metabolites when cultured on autoclaved rice kernels at room temperature for 4 weeks. The organic extracts of fungal culture showed a strong antibiotic activity towards Geotrichum candidum in disk diffusion assays, but they were not toxic to Artemia salina larvae. Two antifungal metabolites were isolated and characterized by chemical and spectroscopic methods as two 3-substituted-4-hydroxy-6-alkyl-2-pyrones, in particular, the 3-(4-deoxy-beta-xylo-hexopyranosyl)-4-hydroxy-6-[2-hydroxy-7-hydroxymeth yl- 1,1,5,9,11-pentamethyl-3,5,8-heptadecatrienyl]-2H-pyran-2-one and its 6-[2-hydroxy-1,1,5,7,9,11-hexamethyl] analog, which were named fusapyrone and Deoxyfusapyrone, respectively.
The synthesis of Deoxyfusapyrone. 2. Preparation of the bis-trisubstituted olefin fragment and its attachment to the pyrone moiety
J Org Chem 2003 Jul 11;68(14):5568-74.PMID:12839448DOI:10.1021/jo034371k.
A convergent and modular synthesis has been devised to construct the eight diastereoisomers of Deoxyfusapyrone (1). In this paper the synthesis of the complex polyene chain is reported as is its connection to the pyrone moiety that is in the middle of the structure of the final target molecule. This route has been fully worked out for one of the isomers and will now be applied in a parallel synthesis format to make all the stereoisomers of 1.
Biological characterization of fusapyrone and Deoxyfusapyrone, two bioactive secondary metabolites of Fusarium semitectum
J Nat Prod 2000 Aug;63(8):1131-5.PMID:10978211DOI:10.1021/np000023r.
Fusapyrone (1) and Deoxyfusapyrone (2), two alpha-pyrones originally isolated from rice cultures of Fusarium semitectum, were tested in several biological assays. Compounds 1 and 2 showed considerable antifungal activity against several plant pathogenic and/or mycotoxigenic filamentous fungi, although they were inactive toward yeasts isolated from plants and the Gram-positive bacterium Bacillus megaterium in disk diffusion assays. Compound 1 was consistently more active than 2. Among the tested fungi, Fusarium species were the least sensitive to the two pyrones, while Alternaria alternata, Ascochyta rabiei, Aspergillusflavus, Botrytis cinerea, Cladosporium cucumerinum, Phoma tracheiphila, and Penicillium verrucosum were the most sensitive. Compounds 1 and 2 also showed good inhibitory activity toward agents of human mycoses. Aspergilli were the most sensitive, while some species-specific variability was found among the Candida spp. In an Artemia salina larvae bioassay, 1 was not toxic at the highest concentration tested (500 microM), whereas the LC(50) of 2 was 37.1 microM (21.8 microg/mL). Neither 1 nor 2 was phytotoxic in a panel of assays that monitored plant-cell toxicity, as well as wilt-, chlorosis-, and necrosis-inducing activity. Moreover, 2 stimulated the root elongation of tomato seedlings at doses of 10 and 100 microM. In consideration of the biological activities evidenced in this study, 1 and 2 appear to be potential candidates for biotechnological applications, as well as good models for studies on mechanism(s) of action and structure-activity relationships.
Isolation and structure elucidation of neofusapyrone from a marine-derived Fusarium species, and structural revision of fusapyrone and Deoxyfusapyrone
J Antibiot (Tokyo) 2006 Nov;59(11):704-9.PMID:17256469DOI:10.1038/ja.2006.94.
Three polyketides containing a pyrone ring, neofusapyrone, fusapyrone, and Deoxyfusapyrone, were isolated from the marine-derived fungus Fusarium sp. FH-146. Their structures were determined by extensive ID- and 2D-NMR and MS spectral analyses. Fusapyrone and Deoxyfusapyrone were originally reported as a-pyrone derivatives; however, the revised structures indicate that they are gamma-pyrone derivatives. These three compounds exhibited antimicrobial activities.