Verticillin B
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| Category | Antibiotics |
| Catalog number | BBF-02753 |
| CAS | 52212-86-9 |
| Molecular Weight | 712.84 |
| Molecular Formula | C30H28N6O7S4 |
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Description
Verticillin B is originally isolated from Verticillium sp. Tm-759. It has the effect of anti-gram-positive bacteria, mycobacterium and protozoa, and has the inhibitory effect on the cancer of Ascites.
Specification
| Synonyms | (6S,6'S)-19-Deoxy-6,6'-dihydroxychetocin |
| IUPAC Name | (1S,2S,3S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14S)-2-hydroxy-14-(hydroxymethyl)-18-methyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione |
| Canonical SMILES | CC12C(=O)N3C4C(C(C3(C(=O)N1C)SS2)O)(C5=CC=CC=C5N4)C67C(C89C(=O)N(C(C(=O)N8C6NC1=CC=CC=C71)(SS9)CO)C)O |
| InChI | InChI=1S/C30H28N6O7S4/c1-25-21(40)35-19-27(13-8-4-6-10-15(13)31-19,17(38)29(35,46-44-25)23(42)33(25)2)28-14-9-5-7-11-16(14)32-20(28)36-22(41)26(12-37)34(3)24(43)30(36,18(28)39)47-45-26/h4-11,17-20,31-32,37-39H,12H2,1-3H3/t17-,18-,19+,20+,25-,26-,27+,28+,29-,30-/m0/s1 |
| InChI Key | YABFNIMWFFFBHC-LRESJZTJSA-N |
Properties
| Appearance | Pale Yellow Prismatic Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; neoplastics (Tumor) |
| Melting Point | 254-256°C |
| Density | 1.92 g/cm3 |
Reference Reading
1. Verticillin A inhibits colon cancer cell migration and invasion by targeting c-Met
Qian-Qian Liu, Xue-Li Zeng, Yue-Lin Guan, Jing-Xin Lu, Kai Tu, Fei-Yan Liu J Zhejiang Univ Sci B. 2020 Oct;21(10):779-795. doi: 10.1631/jzus.B2000190.
Verticillin A is a diketopiperazine compound which was previously isolated from Amanita flavorubescens Alk (containing parasitic fungi Hypomyces hyalines (Schw.) Tul.). Here, we initially found, by wound healing assay and Transwell assay in vitro, that verticillin A possesses an inhibitory effect against the migration and invasion of the human colon cancer cell. Subsequently, c-mesenchymal-epithelial transition factor (c-Met) was identified as a molecular target of verticillin A by screening key genes related to cell migration. Verticillin A-mediated c-Met suppression is at the transcriptional level. Further study demonstrated that verticillin A suppressed c-MET phosphorylation and decreased c-MET protein level. In addition, verticillin A inhibited the phosphorylation of c-MET downstream molecules including rat sarcoma (Ras)-associated factor (Raf), extracellular signal-regulated kinase (ERK), and protein kinase B (AKT). Overexpression of Erk partially reversed the verticillin A-mediated anti-metastasis action in the human colon cancer cell. More importantly, verticillin A also inhibited cancer cell metastasis in vivo. Thus, verticillin A can significantly inhibit the migration and invasion of colon cancer cells by targeting c-Met and inhibiting Ras/Raf/mitogen-activated extracellular signal-regulated kinase (MEK)/ERK signaling pathways. Therefore, we determined that verticillin A is a natural compound that can be further developed as an anti-metastatic drug in human cancers.
2. [Antibacterial secondary metabolites of Clonostachys rosea, an endophytic fungus from Blumea balsamifera (L.) DC]
Xuechun Shu, Yingbo Zhang, Lingliang Guan, Zhenxia Chen, Mei Huang, Xiaolu Chen, Yuan Yuan, Chao Yuan Sheng Wu Gong Cheng Xue Bao. 2020 Aug 25;36(8):1650-1658. doi: 10.13345/j.cjb.190555.
Endophytic fungus is an important treasure trove for discovery of structurally unusual and biologically diverse compounds. A phytochemical investigation on a fungus Clonostachys rosea inhabits inner tissue of Blumea balsamifera (L.) DC. was initiatedrecently in our lab. Six pure compounds were isolated through silica gel column chromatography, sephadex LH-20, and semi-preparative HPLC techniques, with bio-guided strategy. Their structures were characterized as verticillin A (1), (S)-(+)-fusarinolic acid (2), 8-hydroxyfusaric acid (3), cerebroside C (4), 3-Maleimide-5-oxime (5), and bionectriol A (6) by analyses of NMR and MS data. All compounds were tested in vitro antibacterial activities against four strains of bacteria, Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Pseudomonas aeruginosa, and results revealed that 1, 4 and 6 display notableinhibition againstthree bacteria, with MIC values ranging from 2 to 16 μg/mL. Our findings provide references for mining novel antibiotics from endophytes originated from Li Minority medicinal plant B. balsamifera (L.) DC.
3. Erratum to: Verticillin A inhibits colon cancer cell migration and invasion by targeting c-Met
Qianqian Liu, Xueli Zeng, Yuelin Guan, Jingxin Lu, Kai Tu, Feiyan Liu J Zhejiang Univ Sci B. 2022 Apr 15;23(4):352. doi: 10.1631/jzus.B20e0190.
The online version of the original article can be found at https://doi.org/10.1631/jzus.B2000190 Erratum to: J Zhejiang Univ-Sci B (Biomed & Biotechnol) 2020 21(10):779-795 https://doi.org/10.1631/jzus.B2000190.
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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 ╳
