Verticillin C
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| Category | Antibiotics |
| Catalog number | BBF-03444 |
| CAS | 51798-48-2 |
| Molecular Weight | 744.90 |
| Molecular Formula | C30H28N6O7S5 |
| Purity | 95% |
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Description
Verticillin C 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 | Verticillin C |
| IUPAC Name | (1S,2S,3S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14S)-2-hydroxy-14,18-dimethyl-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-(hydroxymethyl)-19-methyl-15,16,17-trithia-10,12,19-triazapentacyclo[12.3.2.01,12.03,11.04,9]nonadeca-4,6,8-triene-13,18-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)(SSS9)CO)C)O |
| InChI | InChI=1S/C30H28N6O7S5/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)47-48-45-26/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 | BMACAVUSMBJNME-LRESJZTJSA-N |
Properties
| Appearance | Pale Yellow Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; neoplastics (Tumor) |
| Melting Point | 230-235°C |
Reference Reading
1.Induction of differentiation in acute promyelocytic leukemia cells (HL-60) by the verticillin derivative Sch 52900.
Erkel G1, Gehrt A, Anke T, Sterner O. Z Naturforsch C. 2002 Jul-Aug;57(7-8):759-67.
The HL-60 cell line, derived from a patient with acute promyelocytic leukemia, is a widely used model system to study the cellular and molecular events involved in differentiation of leukemic cells. In a screening for inducers of differentiation of HL-60 cells, cultures of Gliocladium strain 4-93 were found to produce Sch 52900, a previously isolated diketopiperazine (Chu et al,. J Antibiotics 48, 1440-1445). Sch 52900 induced the differentation of 50-69% of HL-60 cells at concentrations of 6.8-13.6 nM as measured by nitro-blue tetrazolium chloride (NBT) reduction which was followed by apoptosis as shown by DNA fragmentation. Our results demonstrate that growth arrest and the induction of differentiation by Sch 52900 is due to the induction of the cell cycle inhibitor p21WAF and an inhibition of the extracellular signal-regulated kinase (ERK) signaling pathway which leads to the activation of the transcription factor AP-1.
2.Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazine produced by Gliocladium sp.
Chu M1, Truumees I, Rothofsky ML, Patel MG, Gentile F, Das PR, Puar MS, Lin SL. J Antibiot (Tokyo). 1995 Dec;48(12):1440-5.
Sch 52900 (1) and Sch 52901 (2), two new inhibitors of c-fos proto-oncogene induction, have been isolated from the fermentation of broth of the fungal culture (SCF-1168), Gliocladium sp. Along with compounds 1 and 2, a known compound verticillin A (3) was also obtained from the culture. Structure elucidation of 1 and 2, accomplished by analysis of spectral data in comparison with the data of 3, revealed both 1 and 2 were found to be closely related to the verticillin family of diketopiperazines. All three compounds prevented serum-stimulated transcription of the human c-fos promoter, using a fos/lac Z reporter gene assay, with IC50 values of 1.5, 18 and 0.5 microM of 1, 2 and 3, respectively. Northern analysis revealed the exposure of cells to compound 3 causes inhibition of both phorbol ester-induced c-fos induction of serum-induced JE induction in the absence of inhibiting RNA synthesis, as measured by [3H]uridine incorporation. There results suggest that this class of compounds exerts antitumor activity by blocking a signal transduction pathway that is common to and necessary for the induction of at least a subset of immediate early genes involved in cell proliferation.
3.Bionectins A-C, epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120.
Zheng CJ1, Kim CJ, Bae KS, Kim YH, Kim WG. J Nat Prod. 2006 Dec;69(12):1816-9.
Three new epidithiodioxopiperazine compounds, bionectins A (1), B (2), and C (3), along with a known compound, verticillin D (4), have been isolated from the mycelium of liquid fermentation cultures of the fungus Bionectra byssicola F120. The structures of compounds 1-3 were assigned on the basis of MS and NMR data. Compounds 1 and 2 incorporate a dioxopiperazine moiety with a disulfide bridge in their molecules, while 3 contains a dioxopiperazine ring with two methylsulfanyl groups. Compounds 1 and 2 exhibited antibacterial activity against S. aureus including methicillin-resistant S. aureus (MRSA) and quinolone-resistant S. aureus (QRSA), with MIC values of 10-30 microg/mL, while 3 showed no antibacterial activity even at 100 microg/mL.
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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 ╳
