Previridicatumtoxin
目录号 : GC47972
A fungal metabolite with diverse biological activities
Cas No.:1379585-81-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >70.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Previridicatumtoxin is a fungal metabolite that has been found in P. aethiopicum and has diverse biological activities.1,2 It is an intermediate in the biosynthesis of the mycotoxin viridicatumtoxin . Previridicatumtoxin is active against methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (IC50s = 4.4 and 4.8 μM, respectively), as well as C. albicans and S. cerevisiae (MIC = 32 μg/ml for both).2,1 It is cytotoxic to NCI H460, KB-3-1, and SW620 cancer cells (IC50s = 5.3, 4.1, and 6 μM, respectively).2
1.Chooi, Y.H., Wang, P., Fang, J., et al.Discovery and characterization of a group of fungal polycyclic polyketide prenyltransferasesJ. Am. Chem. Soc.134(22)9428-9437(2012) 2.Shang, Z., Salim, A.A., Khalil, Z., et al.Viridicatumtoxins: Expanding on a rare tetracycline antibiotic scaffoldJ. Org. Chem.80(24)12501-12508(2015)
| Cas No. | 1379585-81-5 | SDF | |
| Canonical SMILES | O[C@@H]1[C@]2(O)[C@](C(C(C(N)=O)=C(O)C2)=O)(O)C(C3=C(O)C4=C(O)C=C(OC)C=C4C(C/C=C(C)/CC/C=C(C)/C)=C31)=O | ||
| 分子式 | C30H33NO10 | 分子量 | 567.6 |
| 溶解度 | Dichloromethane: 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。 |
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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 | 1.7618 mL | 8.809 mL | 17.618 mL |
| 5 mM | 0.3524 mL | 1.7618 mL | 3.5236 mL |
| 10 mM | 0.1762 mL | 0.8809 mL | 1.7618 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。
A cytochrome P450 serves as an unexpected terpene cyclase during fungal meroterpenoid biosynthesis
J Am Chem Soc 2013 Nov 13;135(45):16805-8.PMID:24161266DOI:10.1021/ja408966t.
Viridicatumtoxin (1) is a tetracycline-like fungal meroterpenoid with a unique, fused spirobicyclic ring system. Puzzlingly, no dedicated terpene cyclase is found in the gene cluster identified in Penicillium aethiopicum. Cytochrome P450 enzymes VrtE and VrtK in the vrt gene cluster were shown to catalyze C5-hydroxylation and spirobicyclic ring formation, respectively. Feeding acyclic Previridicatumtoxin to Saccharomyces cerevisiae expressing VrtK confirmed that VrtK is the sole enzyme required for cyclizing the geranyl moiety. Thus, VrtK is the first example of a P450 that can catalyze terpene cyclization, most likely via initial oxidation of C17 to an allylic carbocation. Quantum chemical modeling revealed a possible new tertiary carbocation intermediate E that forms after allylic carbocation formation. Intermediate E can readily undergo concerted 1,2-alkyl shift/1,3-hydride shift, either spontaneously or further aided by VrtK, followed by C7 Friedel-Crafts alkylation to afford 1. The most likely stereochemical course of the reaction was proposed on the basis of the results of our computations.