Elsinochrome A
(Synonyms: 痂囊腔菌素AELSINOCHROMEA) 目录号 : GC48434A fungal metabolite
Cas No.:24568-67-0
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
Elsinochrome A is a perylenequinone fungal metabolite that has been found in Hypomyces and has anticancer activity.1 Photoactivation of elsinochrome A induces the production of singlet oxygen and apoptosis in R366.4 rhesus monkey embryonic stem cells and HCe-8693 colorectal carcinoma cells when used at concentrations ranging from 1 to 100 µM.
1.Ma, L., Tai, H., Li, C., et al.Photodynamic inhibitory effects of three perylenequinones on human colorectal carcinoma cell line and primate embryonic stem cell lineWorld J. Gastroenterol.9(3)485-490(2003)
| Cas No. | 24568-67-0 | SDF | |
| 别名 | 痂囊腔菌素AELSINOCHROMEA | ||
| Canonical SMILES | CC([C@H]1C(C2=C(C3=C(C=C4OC)O)C4=C(C(OC)=CC(O)=C56)C5=C2C([C@@H]1C(C)=O)=C(OC)C6=O)=C(OC)C3=O)=O | ||
| 分子式 | C30H24O10 | 分子量 | 544.5 |
| 溶解度 | 储存条件 | -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 | 1.8365 mL | 9.1827 mL | 18.3655 mL |
| 5 mM | 0.3673 mL | 1.8365 mL | 3.6731 mL |
| 10 mM | 0.1837 mL | 0.9183 mL | 1.8365 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。
Inhibitory Effects and Mechanism of Action of Elsinochrome A on Candida albicans and Its Biofilm
J Fungi (Basel) 2022 Aug 11;8(8):841.PMID:36012829DOI:10.3390/jof8080841.
Biofilm-associated Candida albicans infections, the leading cause of invasive candidiasis, can cause high mortality rates in immunocompromised patients. Photodynamic antimicrobial chemotherapy (PACT) is a promising approach for controlling infections caused by biofilm-associated C. albicans. This study shows the effect of Elsinochrome A (EA) against different stages of C. albicans biofilms in vitro by XTT reduction assay and crystal violet staining. The mechanism of action of EA on C. albicans biofilm was analyzed with flow cytometry, confocal laser microscopy, and the Real-Time Quantitative Reverse Transcription PCR (qRT-PCR). EA-mediated PACT significantly reduced the viability of C. albicans, with an inhibition rate on biofilm of 89.38% under a concentration of 32 μg/mL EA. We found that EA could not only inhibit the adhesion of C. albicans in the early stage of biofilm formation, but that it also had good effects on pre-formed mature biofilms with a clearance rate of 35.16%. It was observed that EA-mediated PACT promotes the production of a large amount of reactive oxygen species (ROS) in C. albicans and down-regulates the intracellular expression of oxidative-stress-related genes, which further disrupted the permeability of cell membranes, leading to mitochondrial and nuclear damage. These results indicate that EA has good photodynamic antagonizing activity against the C. albicans biofilm, and potential clinical value.
Heterologous biosynthesis of Elsinochrome A sheds light on the formation of the photosensitive perylenequinone system
Chem Sci 2018 Nov 22;10(5):1457-1465.PMID:30809363DOI:10.1039/c8sc02870b.
Perylenequinones are a class of aromatic polyketides characterised by a highly conjugated pentacyclic core, which confers them with potent light-induced bioactivities and unique photophysical properties. Despite the biosynthetic gene clusters for the perylenequinones Elsinochrome A (1), cercosporin (4) and hypocrellin A (6) being recently identified, key biosynthetic aspects remain elusive. Here, we first expressed the intact elc gene cluster encoding 1 from the wheat pathogen Parastagonospora nodorum heterologously in Aspergillus nidulans on a yeast-fungal artificial chromosome (YFAC). This led to the identification of a novel flavin-dependent monooxygenase, ElcH, responsible for oxidative enolate coupling of a perylenequinone intermediate to the hexacyclic dihydrobenzo(ghi)perylenequinone in 1. In the absence of ElcH, the perylenequione intermediate formed a hexacyclic cyclohepta(ghi)perylenequinone system via an intramolecular aldol reaction resulting in 6 and a novel hypocrellin 12 with opposite helicity to 1. Theoretical calculations supported that 6 and 12 resulted from atropisomerisation upon formation of the 7-membered ring. Using a bottom-up pathway reconstruction approach on a tripartite YFAC system developed in this study, we uncovered that both a berberine bridge enzyme-like oxidase ElcE and a laccase-like multicopper oxidase ElcG are involved in the double coupling of two naphthol intermediates to form the perylenequinone core. Gene swapping with the homologs from the biosynthetic pathway of 4 showed that cognate pairing of the two classes of oxidases is required for the formation of the perylenequinone core, suggesting the involvement of protein-protein interactions.
A novel Elsinochrome A derivative: a study of drug delivery and photodynamic activity
Photochem Photobiol Sci 2009 Dec;8(12):1676-82.PMID:20024164DOI:10.1039/b9pp00046a.
Elsinochrome A (EA) possesses the highest singlet-oxygen quantum yield (0.98) amongst the perilenoquinoid pigments and may be suitable as a phototherapeutic drug. However, there have been virtually no studies into its medicinal applications. Based on the analysis of chemical derivatives of hypocrellins (the same family as EA), 5-(3-mercapto-1-propanesulfonic acid)-substituted Elsinochrome A (MPEA) with an amphiphilicity was designed and synthesized by considering drug delivery and biological activity requirements. MPEA possesses a water solubility of 5.1 mg mL(-1), which is just sufficient to enable dissolution at a clinically acceptable concentration, while its partition coefficient (n-octanol/phosphate buffered saline) of 7 guarantees affinity to biological targets. MPEA could photogenerate semiquinone anion radicals and reactive oxygen species, especially singlet oxygen, at a yield of 0.73, which approaches that for hypocrellin B. Biological tests confirmed that the photodynamic activity of MPEA was as high as 60% of that of its parent EA, which is significantly higher than that of most other photosensitizers.
Structure of Elsinochrome A: a perylenequinone metabolite
Acta Crystallogr C 1989 Apr 15;45 ( Pt 4):628-32.PMID:2610978DOI:10.1107/s0108270188012831.
trans-1,2-Diacetyl-1,2-dihydro-5,10-dihydroxy-3,7,8,12- tetramethoxybenzo[ghi]perylene-4,11-dione, C30H24O10, Mr = 544.51, orthorhombic, P2(1)2(1)2(1), Z = 4, a = 12.428 (3), b = 13.048 (3), c = 14.933 (3) A, V = 2421.5 (9) A3, Dx = 1.494, Dm (by flotation) = 1.48 g cm-3, lambda(Mo K alpha) = 0.71069 A, mu = 1.057 cm-1, F(000) = 1136, T = 293 K, R = 0.046 (2065 observed reflections). Elsinochrome A is shown to exist in the solid state as a nonplanar quinone tautomer; the pigment adopts a helical conformation, in analogy with the related cercosporin, but the perylenequinone moiety in Elsinochrome A appears to be significantly less skewed.
Elsinochrome A production by the bindweed biocontrol fungus Stagonospora convolvuli LA39 does not pose a risk to the environment or the consumer of treated crops
FEMS Microbiol Ecol 2007 Jan;59(1):194-205.PMID:17092310DOI:10.1111/j.1574-6941.2006.00207.x.
Biological control as an alternative to chemical pesticides is of increasing public interest. However, to ensure safe use of biocontrol methods, strategies to assess the possible risks need to be developed. The production of toxic metabolites is an aspect which has so far largely been neglected in the risk assessment and the registration process for biocontrol products. We have evaluated the risks of Elsinochrome A (ELA) and leptosphaerodione production by the fungus Stagonospora convolvuli LA39, an effective biocontrol agent used against bindweeds. The toxicity of the two metabolites to bacteria, protozoa, fungi and plants was evaluated in in vitro assays. The most sensitive bacteria and fungi were already affected at 0.01-0.07 microM ELA, whereas plants were far less sensitive. Leptosphaerodione was less toxic than ELA. Subsequently, it was investigated whether ELA is present in the applied biocontrol product or LA39-treated bindweed and crop plants. In plants ELA was never detected and in the biocontrol product the ELA concentration was far too low to have toxic effects even on the most sensitive organisms. We conclude that the production of ELA by biocontrol strain LA39 does not pose a risk to the environment or to the consumer.