Aspochalasin D
目录号 : GC42860
A fungal metabolite
Cas No.:71968-02-0
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
Aspochalasin D is a co-metabolite originally isolated from A. microcysticus with aspochalasins A, B, and C, that was initially thought to be inactive. It has antibacterial activity against Gram-positive and Gram-negative bacteria at a concentration of 1 mg/ml. Aspochalasin D is more cytotoxic, via apoptosis, to Ba/F3-V12 cells in an IL-3-free medium than in an IL-3-containing medium (IC50s = 0.49 and 1.9 µg/ml, respectively).
| Cas No. | 71968-02-0 | SDF | |
| Canonical SMILES | C/C1=C\[C@]2([H])[C@@]3(C(/C=C/[C@H](O)[C@H](O)CC1)=O)[C@@]([C@H](CC(C)C)NC3=O)([H])[C@H](C)C(C)=C2 | ||
| 分子式 | C24H35NO4 | 分子量 | 401.5 |
| 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 | |||
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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。
Enhanced production of Aspochalasin D through genetic engineering of Aspergillus flavipes
Appl Microbiol Biotechnol 2023 May;107(9):2911-2920.PMID:37004567DOI:10.1007/s00253-023-12501-8.
Aspochalasin D (AD) belongs to the polyketide-amino acid hybrid natural products with anti-cancer, anti-bacterial, and anti-fouling bioactivities. However, the low production limits its further application. In this study, AD was separated and identified from Aspergillus flavipes 3.17641. Next, besides the optimization of culture conditions using a single-factor experiment and response surface methodology, metabolic engineering was employed to increase the AD production. It shows that the deletion of the shunt gene aspoA and overexpression of the pathway-specific regulator aspoG significantly improve the AD production. Its production reached to 812.1 mg/L under the optimized conditions, with 18.5-fold increase. Therefore, this study not only provides a general method for improving the production of similar natural products in other fungi, but also enables the further biological function development of AD in agriculture and pharmaceutical. KEY POINTS: • The Aspochalasin D (AD) production was improved by optimizing culture conditions. • The deletion of the shunt gene aspoA increased the AD production. • Overexpression of the pathway regulator aspoG further improved the AD production.
Aspochalamins A-D and aspochalasin Z produced by the endosymbiotic Fungus aspergillus niveus LU 9575. I. Taxonomy, fermentation, isolation and biological activities
J Antibiot (Tokyo) 2004 Nov;57(11):707-14.PMID:15712664DOI:10.7164/antibiotics.57.707.
Aspochalamins A-D, a family of new cytochalasan antibiotics have been isolated from Aspergillus niveus, an endosymbiotic fungus isolated from the gut of a woodlouse belonging to the family Trichoniscidae. Besides aspochalamins, aspochalasin Z, a new member of the aspochalasin family, as well as the known mycotoxins Aspochalasin D and citreoviridins A/C and B were isolated from the mycelium. Aspochalamins showed cytostatic effects towards various tumor cell lines and a weak antibacterial activity against Gram-positive bacteria.
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.
Trichodermone, a spiro-cytochalasan with a tetracyclic nucleus (7/5/6/5) skeleton from the plant endophytic fungus Trichoderma gamsii
J Nat Prod 2014 Jan 24;77(1):164-7.PMID:24422592DOI:10.1021/np4007487.
Trichodermone (1), the first spiro-cytochalasan with an unprecedented tetracyclic nucleus (7/5/6/5), together with its possible biosynthetic precursor Aspochalasin D (2), was isolated from the endophytic fungus Trichoderma gamsii. Compound 2 displayed moderate inhibitory activity against HeLa cells with an IC50 value of 5.72 μM.
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.