Aspergillin PZ
目录号 : GC42858
A fungal metabolite
Cas No.:483305-08-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Aspergillin PZ is a fungal metabolite originally isolated from A. awamori. It induces morphological deformation of P. oryzae conidia when used at a concentration of 89 nM. Aspergillin PZ is active against S. epidermidis (MIC = 20 μM) but not S. aureus, E. coli, or B. cereus (MICs = >20 μM). It is cytotoxic to HL-60 promyelocytic leukemia cells (IC50 = 56.61 μM) but not THP-1 acute monocytic leukemia or PC3 prostate cancer cells (IC50s = >80 μM).
| Cas No. | 483305-08-4 | SDF | |
| Canonical SMILES | CC1=C[C@@]([C@]2([H])[C@@](C3)([H])[C@@]4([H])[C@H](O)CC[C@@]2(O4)C)([H])[C@@]([C@@]5([H])[C@@H]1C)(C(N[C@H]5CC(C)C)=O)C3=O | ||
| 分子式 | C24H35NO4 | 分子量 | 401.5 |
| 溶解度 | 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 | 2.4907 mL | 12.4533 mL | 24.9066 mL |
| 5 mM | 0.4981 mL | 2.4907 mL | 4.9813 mL |
| 10 mM | 0.2491 mL | 1.2453 mL | 2.4907 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。
Biomimetic Synthesis of (+)-Aspergillin PZ
Angew Chem Int Ed Engl 2018 Nov 19;57(47):15587-15591.PMID:30239081DOI:10.1002/anie.201809703.
The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels-Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of Aspergillin PZ, an intricate pentacyclic aspochalasan.
Aspergillin PZ, a novel isoindole-alkaloid from Aspergillus awamori
J Antibiot (Tokyo) 2002 Aug;55(8):693-5.PMID:12374381DOI:10.7164/antibiotics.55.693.
Aspergillin PZ was obtained from the fermentation of Aspergillus awamori (Nakazawa) by activity-guided fractionation and purification. Its structure was elucidated on the basis of spectral data, especially by 2D NMR, and finally confirmed by an X-ray analysis. It could induce conidia of P. oryzae to deform moderately.
Identification of an Unexpected 2-Oxonia[3,3]sigmatropic Rearrangement/Aldol Pathway in the Formation of Oxacyclic Rings. Total Synthesis of (+)-Aspergillin PZ
Tetrahedron 2011 Dec 23;67(51):9837-9843.PMID:22518066DOI:10.1016/j.tet.2011.09.079.
This paper reports the first unambiguous evidence that the cascade synthesis of tetrahydrofuran-containing oxacyclic molecules depicted in Scheme 12 can take place by a 2-oxonia[3,3]sigmatropic/aldol mechanism rather than by a Prins cyclization/pinacol rearrangement sequence. The 8-oxabicyclo[3.2.1]octyl aldehyde products of this reaction, 20 and 29, were employed to complete the first total synthesis of the structurally remarkable isoindolone alkaloid (+)-aspergillin PZ (1). The lack of activity seen in two tumor cell lines for synthetic (+)-aspergillin PZ calls into question the suggestion that Aspergillin PZ, like many aspochalasin diterpenes, might exhibit useful antitumor properties.
Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii
Fitoterapia 2014 Jul;96:115-22.PMID:24752139DOI:10.1016/j.fitote.2014.04.009.
Three new cytochalasans, trichalasins E (1), F (2) and H (7), together with four known analogues, trichalasin C (3), aspochalasin K (4), trichalasin G (5) and Aspergillin PZ (8), were isolated from one endophytic fungus Trichoderma gamsii inhabiting in the traditional medicinal plant Panax notoginseng (BurK.) F.H. Chen. Trichalasins E (1) contains a unique hydroperoxyl group, which is the first report in all known analogues, whereas trichalasin H (7) possesses the rare 6/5/6/6/5 pentacyclic skeleton with 12-oxatricyclo [6.3.1.0(2,7)] moiety as that of Aspergillin PZ (8). The relative configurations of the new compounds were characterized by analysis of coupling constants and ROESY correlations, and the absolute configurations of trichalasins E (1), H (7) and Aspergillin PZ (8) were determined by modified Mosher's reaction. In addition, compounds 1-5, 7 and 8 were tested cytotoxic activities against several cancer cell lines.
Bioinspired Network Analysis Enabled Divergent Syntheses and Structure Revision of Pentacyclic Cytochalasans
Angew Chem Int Ed Engl 2021 Jul 12;60(29):15963-15971.PMID:33860618DOI:10.1002/anie.202102831.
We accomplished the divergent total syntheses of ten pentacyclic cytochalasans (Aspergillin PZ, trichodermone, trichoderones, flavipesines, and flavichalasines) from a common precursor aspochalasin D and revised the structures of trichoderone B, spicochalasin A, flavichalasine C, aspergilluchalasin based on structure network analysis of the cytochalasans biosynthetic pathways and DFT calculations. The key steps of the syntheses include transannular alkene/epoxyalkene and carbonyl-ene cyclizations to establish the C/D ring of pentacyclic aspochalasans. Our bioinspired approach to these pentacyclic cytochalasans validate the proposed biosynthetic speculation from a chemical view and provide a platform for the synthesis of more than 400 valuable cytochalasans bearing different macrocycles and amino-acid residues.