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Viridiol Sale

(Synonyms: 绿毛菌醇) 目录号 : GC41527

A phytotoxin

Viridiol Chemical Structure

Cas No.:23820-80-6

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250μg
¥770.00
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1mg
¥2,467.00
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产品描述

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.

Chemical Properties

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
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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
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Research Update

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.