Viridicatol
(Synonyms: 纯绿青霉醇) 目录号 : GC45147
A fungal metabolite
Cas No.:14484-44-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Viridicatol is a fungal metabolite that has been found in various Penicillium species as well as Phoma. It suppresses the expression of COX-2 and inducible nitric oxide synthase (iNOS) and inhibits production of nitric oxide and prostaglandin E2 (PGE2) in LPS-stimulated RAW 264.7 and BV2 cells. It also inhibits NF-κB DNA-binding activity, nuclear translocation of NF-κB p65 and p50 heterodimers, and blocks degradation of inhibitor of kappa B α (IκBα) in the cytoplasm of LPS-stimulated RAW 264.7 and BV2 cells. Viridicatol inhibits the growth of F. graminearum in a disc assay. It also inhibits protein tyrosine phosphatase 1B (PTB1B) in vitro (IC50 = 64 μM).
| Cas No. | 14484-44-7 | SDF | |
| 别名 | 纯绿青霉醇 | ||
| Canonical SMILES | O=C1C(O)=C(C2=CC(O)=CC=C2)C3=CC=CC=C3N1 | ||
| 分子式 | C15H11NO3 | 分子量 | 253.3 |
| 溶解度 | DMSO : 125 mg/mL (493.58 mM; Need ultrasonic) | 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 | 3.9479 mL | 19.7394 mL | 39.4789 mL |
| 5 mM | 0.7896 mL | 3.9479 mL | 7.8958 mL |
| 10 mM | 0.3948 mL | 1.9739 mL | 3.9479 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。
Viridicatol Isolated from Deep-Sea Penicillium Griseofulvum Alleviates Anaphylaxis and Repairs the Intestinal Barrier in Mice by Suppressing Mast Cell Activation
Mar Drugs 2020 Oct 16;18(10):517.PMID:33081290DOI:10.3390/md18100517.
Viridicatol is a quinoline alkaloid isolated from the deep-sea-derived fungus Penicillium griseofulvum. The structure of Viridicatol was unambiguously established by X-ray diffraction analysis. In this study, a mouse model of ovalbumin-induced food allergy and the rat basophil leukemia (RBL)-2H3 cell model were established to explore the anti-allergic properties of Viridicatol. On the basis of the mouse model, we found Viridicatol to alleviate the allergy symptoms; decrease the levels of specific immunoglobulin E, mast cell protease-1, histamine, and tumor necrosis factor-α; and promote the production of interleukin-10 in the serum. The treatment of Viridicatol also downregulated the population of B cells and mast cells (MCs), as well as upregulated the population of regulatory T cells in the spleen. Moreover, Viridicatol alleviated intestinal villi injury and inhibited the degranulation of intestinal MCs to promote intestinal barrier repair in mice. Furthermore, the accumulation of Ca2+ in RBL-2H3 cells was significantly suppressed by Viridicatol, which could block the activation of MCs. Taken together, these data indicated that deep-sea Viridicatol may represent a novel therapeutic for allergic diseases.
Biosynthesis of Viridicatol in Penicillium palitans Implies a Cytochrome P450-Mediated meta Hydroxylation at a Monoalkylated Benzene Ring
Org Lett 2022 Jan 14;24(1):262-267.PMID:34928155DOI:10.1021/acs.orglett.1c03932.
Cyclopenol (1) and Viridicatol (6) with m-hydroxyl groups were isolated from a culture of Penicillium palitans. Genome mining and heterologous expression in Aspergillus nidulans led to the identification of their biosynthetic gene cluster and the cytochrome P450 enzyme VdoD responsible for the meta hydroxylation. Precursor feeding experiments into vdoD transformant proved the conversion of cyclopenin (2) to 1, which then undergoes a spontaneous or VdoA-catalyzed rearrangement to 6. A direct conversion of viridicatin (5) to 6 by VdoD was not detected.
Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel-Crafts Alkylation Strategy
J Org Chem 2018 Nov 2;83(21):13132-13145.PMID:30272451DOI:10.1021/acs.joc.8b01871.
The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. This methodology has been utilized for the synthesis of naturally occurring Viridicatol, a fungal metabolite isolated from the penicillium species.
3-Hy-droxy-4-(3-hy-droxy-phen-yl)-2-quinolone monohydrate
Acta Crystallogr Sect E Struct Rep Online 2011 Aug 1;67(Pt 8):o2195-6.PMID:22091203DOI:10.1107/S160053681102945X.
In the title compound, also known as Viridicatol monohydrate, C(15)H(11)NO(3)·H(2)O, the dihedral angle between the benzene ring and quinoline ring system is 64.76 (5)°. An intra-molecular O-H⋯O hydrogen bond occurs. The crystal structure is stabilized by classical inter-molecular N-H⋯O and O-H⋯O hydrogen bonds and weak π-π inter-actions with a centroid-centroid distance of 3.8158 (10) Å.
Chemical Constituents of the Deep-Sea-Derived Penicillium solitum
Mar Drugs 2021 Oct 17;19(10):580.PMID:34677479DOI:10.3390/md19100580.
A systematic chemical investigation of the deep-sea-derived fungus Penicillium solitum MCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2 and 3), and 22 known (4-25) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (13) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC50 values of around 20 μM. Moreover, 13 displayed potent in vitro anti-food allergic activity with an IC50 value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (9) and penicopeptide A (10) showed moderate effects (IC50 = 50 and 58 μM, respectively).