Viridiol
(Synonyms: 绿毛菌醇) 目录号 : GC41527A phytotoxin
Cas No.:23820-80-6
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Viridiol is a fungal steroid that demonstrates phytotoxic activity. It is a metabolite of the fungistatic compound, viridin. Both viridin and viridiol are reported to inhibit PI3K.
Cas No. | 23820-80-6 | SDF | |
别名 | 绿毛菌醇 | ||
Canonical SMILES | O=C1CCC2=C1C=CC([C@]3(C)C4=C5OC=C4[C@@H](O)[C@@H](OC)[C@H]3O)=C2C5=O | ||
分子式 | C20H18O6 | 分子量 | 354.4 |
溶解度 | Soluble in DMSO | 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 | |||
1 mg | 5 mg | 10 mg | |
1 mM | 2.8217 mL | 14.1084 mL | 28.2167 mL |
5 mM | 0.5643 mL | 2.8217 mL | 5.6433 mL |
10 mM | 0.2822 mL | 1.4108 mL | 2.8217 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 Synthesis of Viridin and Viridiol
J Am Chem Soc 2019 Oct 16;141(41):16208-16212.PMID:31554399DOI:10.1021/jacs.9b08577.
The asymmetric total synthesis of (-)-viridin and (-)-viridiol, antifungal metabolites, was achieved in 17 and 18 steps from a commercially available starting material. An intramolecular [3+2] cycloaddition was applied to an easily available l-ribose derivative in order to construct the highly substituted D ring containing the key chiral cis-triol fragment. Co-catalyzed metal-hydride H atom transfer (MHAT) radical cyclization was utilized to form the C-ring and the all-carbon quaternary center at C-10. This convergent strategy provides a scalable approach to prepare viridin and Viridiol for biological studies.
The furan-osteroid Viridiol
Acta Crystallogr Sect E Struct Rep Online 2013 Mar 2;69(Pt 4):o467-8.PMID:23634026DOI:10.1107/S1600536813005606.
The asymmetric unit of the title compound, C20H18O6 (systematic name: 1β,3β-dihy-droxy-2β-meth-oxyfuro[4',3',2':4,5,6]-18-norandrosta-8,11,13-triene-7,17-dione), a dihydro derivative of the fungal steroid viridin, contains two mol-ecules with similar conformations. The rings bearing the hy-droxy groups adopt boat conformations. The absolute structure was assigned based on the known chirality of a precursor compound. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating a three-dimensional network and weak C-H⋯O inter-actions consolidate the packing.
Bioconversion of antifungal viridin to phytotoxin Viridiol by environmental non-viridin producing microorganisms
Bioorg Chem 2021 Jul;112:104959.PMID:33971564DOI:10.1016/j.bioorg.2021.104959.
Biotransformation of viridin, an antifungal produced by biocontrol agent, with non-viridin producing microorganisms is studied. The results show that some environmental non-targeted microorganisms are able to reduce it in the known phytotoxin Viridiol, and its 3-epimer. Consequently, this reduction, which happens in some cases by detoxification mechanism, could be disastrous for the plant in a biocontrol of plant disease. However, a process fermentation/biotransformation could be an efficient approach for the preparation of this phytotoxin.
Conversion of viridin to Viridiol by viridin-producing fungi
Can J Microbiol 1987 Nov;33(11):963-6.PMID:3447692DOI:10.1139/m87-169.
The fungistatic compound viridin, produced by the fungus Gliocladium virens, was found to be irreversibly reduced to the phytotoxin Viridiol in liquid culture. Conversion occurred only in the presence of viridin-producing fungi and was subsequent to viridin production. Radiolabelled viridin was rapidly taken up by the mycelium of G. virens and reduced to radiolabelled Viridiol, while labelled Viridiol was not taken up to any significant extent by the mycelium. Reduction of viridin to Viridiol was independent of culture pH, carbon source, and nitrogen source or quantity. A simple production system consisting of peat moss amended with dextrose and calcium nitrate and inoculated with G. virens supported production of 86 micrograms Viridiol/g peat. This production system, when applied to soil, may have value as a herbicide.
9-epi-Viridiol, a novel cytotoxic furanosteroid from soil fungus Trichoderma virens
Nat Prod Res 2006 Dec;20(14):1321-5.PMID:17393658DOI:10.1080/14786410601101969.
A novel furanosteroid named 9-epi-viridiol (1), along with Viridiol (2) and mevalonic acid (3), was isolated from Trichoderma virens. The structure of 1 was verified by combined spectroscopic data (COSY, HSQC, HMBC and NOESY) to be a C-9 epimer of Viridiol. 9-epi-Viridiol exhibited cytotoxicity towards HeLa and KB cells with IC50 values of 19 and 50 microg mL(-1), respectively.