Cephalochromin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02425 |
| CAS | 25908-26-3 |
| Molecular Weight | 518.5 |
| Molecular Formula | C28H22O10 |
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Description
Cephalochromin is a calmodulin-sensitive phosphodiesterase (PDE) inhibitor isolated from the culture broth of an unidentified fungal isolate, SCF-125. It inhibited calmodulin-sensitive PDE activities with IC50 values of 40-47 nM.
Specification
| Synonyms | Sch 45752; Sch-45752 |
| IUPAC Name | 5,6,8-trihydroxy-2-methyl-9-(5,6,8-trihydroxy-2-methyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl)-2,3-dihydrobenzo[g]chromen-4-one |
| Canonical SMILES | CC1CC(=O)C2=C(O1)C=C3C(=C2O)C(=CC(=C3C4=C(C=C(C5=C(C6=C(C=C54)OC(CC6=O)C)O)O)O)O)O |
| InChI | InChI=1S/C28H22O10/c1-9-3-13(29)25-19(37-9)5-11-21(15(31)7-17(33)23(11)27(25)35)22-12-6-20-26(14(30)4-10(2)38-20)28(36)24(12)18(34)8-16(22)32/h5-10,31-36H,3-4H2,1-2H3 |
| InChI Key | JGQBYBXYRUCBQY-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Solid |
| Melting Point | >300°C |
Reference Reading
1. Design of Fungal Co-Cultivation Based on Comparative Metabolomics and Bioactivity for Discovery of Marine Fungal Agrochemicals
Ernest Oppong-Danquah, Paulina Budnicka, Martina Blümel, Deniz Tasdemir Mar Drugs. 2020 Jan 23;18(2):73. doi: 10.3390/md18020073.
Microbial co-cultivation is employed for awakening silent biosynthetic gene clusters (BGCs) to enhance chemical diversity. However, the selection of appropriate partners for co-cultivation remains a challenge. Furthermore, competitive interactions involving the suppression of BGCs or upregulation of known, functional metabolite(s) during co-cultivation efforts is also common. Herein, we performed an alternative approach for targeted selection of the best co-cultivation pair. Eight marine sediment-derived fungi were classified as strong or weak, based on their anti-phytopathogenic potency. The fungi were co-cultured systematically and analyzed for their chemical profiles and anti-phytopathogenic activity. Based on enhanced bioactivity and a significantly different metabolite profile including the appearance of a co-culture specific cluster, the co-culture of Plenodomus influorescens (strong) and Pyrenochaeta nobilis (weak) was prioritized for chemical investigation. Large-scale co-cultivation resulted in isolation of five polyketide type compounds: two 12-membered macrolides, dendrodolide E (1) and its new analog dendrodolide N (2), as well as two rare azaphilones spiciferinone (3) and its new analog 8a-hydroxy-spiciferinone (4). A well-known bis-naphtho-γ-pyrone type mycotoxin, cephalochromin (5), whose production was specifically enhanced in the co-culture, was also isolated. Chemical structures of compounds 1-5 were elucidated by NMR, HRMS and [] analyses. Compound 5 showed the strongest anti-phytopathogenic activity against Xanthomonas campestris and Phytophthora infestans with IC50 values of 0.9 and 1.7 µg/mL, respectively.
2. Two new cephalochromin derivative from the Alternaria sp. ZG22
Xin-Ming Song, Xue-Ming Zhou, Ya-Ling Li, Li-Bing Huang, Cai-Cui Chen, Yan Gao, Lin He, Xiao-Qun Mao, Bing Chen, Jing-Wen Liu, Hui-Jie Liu, Xiao-Ping Song, Chang-Ri Han Nat Prod Res. 2021 Oct;35(20):3370-3375. doi: 10.1080/14786419.2019.1700248. Epub 2019 Dec 14.
Two new cephalochromin derivatives, prenylcephalochromin A (1), prenylcephalochromin B (2), along with cephalochromin (3) were isolated from the Alternaria sp. ZG22 obtained from a Dasymaschalon rostratum collected from the Hainan. The structures of two new compounds were elucidated by comprehensive spectroscopic methods. Compounds 1-3 showed α-glucosidase inhibitory activity.
3. Induction of Isochromanones by Co-Cultivation of the Marine Fungus Cosmospora sp. and the Phytopathogen Magnaporthe oryzae
Ernest Oppong-Danquah, Martina Blümel, Silvia Scarpato, Alfonso Mangoni, Deniz Tasdemir Int J Mol Sci. 2022 Jan 11;23(2):782. doi: 10.3390/ijms23020782.
Microbial co-cultivation is a promising approach for the activation of biosynthetic gene clusters (BGCs) that remain transcriptionally silent under artificial culture conditions. As part of our project aiming at the discovery of marine-derived fungal agrochemicals, we previously used four phytopathogens as model competitors in the co-cultivation of 21 marine fungal strains. Based on comparative untargeted metabolomics analyses and anti-phytopathogenic activities of the co-cultures, we selected the co-culture of marine Cosmospora sp. with the phytopathogen Magnaporthe oryzae for in-depth chemical studies. UPLC-MS/MS-based molecular networking (MN) of the co-culture extract revealed an enhanced diversity of compounds in several molecular families, including isochromanones, specifically induced in the co-culture. Large scale co-cultivation of Cosmospora sp. and M. oryzae resulted in the isolation of five isochromanones from the whole co-culture extract, namely the known soudanones A, E, D (1-3) and their two new derivatives, soudanones H-I (4-5), the known isochromans, pseudoanguillosporins A and B (6, 7), naphtho-γ-pyrones, cephalochromin and ustilaginoidin G (8, 9), and ergosterol (10). Their structures were established by NMR, HR-ESIMS, FT-IR, electronic circular dichroism (ECD) spectroscopy, polarimetry ([α]D), and Mosher's ester reaction. Bioactivity assays revealed antimicrobial activity of compounds 2 and 3 against the phytopathogens M. oryzae and Phytophthora infestans, while pseudoanguillosporin A (6) showed the broadest and strongest anti-phytopathogenic activity against Pseudomonas syringae, Xanthomonas campestris, M. oryzae and P. infestans. This is the first study assessing the anti-phytopathogenic activities of soudanones.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
