Streptovaricin A
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| Category | Antibiotics |
| Catalog number | BBF-03070 |
| CAS | 23344-16-3 |
| Molecular Weight | 827.87 |
| Molecular Formula | C42H53NO16 |
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Description
Streptovaricin A is a macrolide Ansa antibiotic produced by Str. spectabilis NRRL 2494. It has a broad-spectrum anti-bacterial effect, but its anti-gram-negative bacteria activity is weak.
Specification
| Synonyms | B-44-PC; Streptovaricin complex, fraction a |
| IUPAC Name | methyl (7E,9Z,11S,12S,13S,14R,15R,16R,17R,18R,19R,20E)-2,16-diacetyloxy-11,12,14,18,19,31-hexahydroxy-3,7,11,13,17,19,21,27-octamethyl-6,28-dioxo-23,25-dioxa-5-azatetracyclo[20.7.1.14,29.026,30]hentriaconta-1,3,7,9,20,22(30),26,29(31)-octaene-15-carboxylate |
| Canonical SMILES | CC1C(C(C(C(C(C(C=C(C2=C3C4=C(C(=C(C(=C4C(=O)C(=C3OCO2)C)O)NC(=O)C(=CC=CC(C1O)(C)O)C)C)OC(=O)C)C)(C)O)O)C)OC(=O)C)C(=O)OC)O |
| InChI | InChI=1S/C42H53NO16/c1-17-13-12-14-41(9,53)37(49)21(5)31(47)28(40(52)55-11)36(59-24(8)45)22(6)38(50)42(10,54)15-18(2)33-27-25-26(30(46)20(4)34(27)57-16-56-33)32(48)29(43-39(17)51)19(3)35(25)58-23(7)44/h12-15,21-22,28,31,36-38,47-50,53-54H,16H2,1-11H3,(H,43,51)/b14-12-,17-13+,18-15+/t21-,22-,28+,31+,36+,37-,38+,41-,42+/m0/s1 |
| InChI Key | DAQTVVQVNADAHI-UTLNPYKCSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | bacteria; Gram-negative bacteria |
| Boiling Point | 946.7±65.0°C at 760 mmHg |
| Melting Point | 200-201°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Two new streptovaricin derivatives from mutants of Streptomyces spectabilis CCTCC M2017417
Minghe Luo, Yulu Dong, Lingjie Tang, Xu Chen, Zhiwei Hu, Wenxinyu Xie, Zixin Deng, Yuhui Sun Nat Prod Res. 2022 Jul;36(14):3689-3694. doi: 10.1080/14786419.2021.1881517. Epub 2021 Feb 8.
Two new ansamycin derivatives, damavaricin H (1) and protostreptovaricin VI (2) were isolated from the Streptomyces spectabilis CCTCC M2017417 derived mutants of ΔstvP5 and ΔstvA2, respectively. The structures of 1 and 2 were established by analysis of the HRESIMS as well as 1D and 2D NMR datasets. The minimum inhibitory concentration (MIC) results showed that compounds 1 and 2 possessed the corresponding anti-MRSA bioactivities of 4 ~ 8 μg/ml and 8 ~ 16 μg/ml, which confirmed the structure-activity relationships of streptovaricins reported previously and also revealed that addition of the hydroxyl group at C-8 increased the anti-MRSA activity.
2. Ansavaricin J, a New Heterocyclic Ring-Fused Streptovaricin from Gene stvP5-Deleted Mutant of Streptomyces spectabilis CCTCC M2017417
Yuan-Zhen Liu, Xu Chen, Zheng-Yuan Li, Li-Xia Huang, Yu-Hui Sun Chem Biodivers. 2020 Aug;17(8):e1900713. doi: 10.1002/cbdv.201900713. Epub 2020 Jul 27.
A new ring-fused streptovaricin analogue, named ansavaricin J, was unprecedently isolated from the culture of the genetically modified strains ΔstvP5 which derived from Streptomyces spectabilis CCTCC M2017417. Its structure was elucidated via comprehensive spectroscopic analyses, including 1D- and 2D-NMR tests, and HR-ESI-MS data analysis. Notably, ansavaricin J and E represent the only two reported examples of heterocyclic ring-fused streptovaricins thus far, however, it only showed insignificant antibacterial activities against Staphylococcus aureus.
3. Functional Analysis of Cytochrome P450s Involved in Streptovaricin Biosynthesis and Generation of Anti-MRSA Analogues
Yuanzhen Liu, Xu Chen, Zhengyuan Li, Wei Xu, Weixin Tao, Jie Wu, Jian Yang, Zixin Deng, Yuhui Sun ACS Chem Biol. 2017 Oct 20;12(10):2589-2597. doi: 10.1021/acschembio.7b00467. Epub 2017 Sep 7.
The streptovaricins, chemically related to the rifamycins, are highly effective antibacterial agents, particularly against mycobacteria. Herein, a bioassay-guided investigation of Streptomyces spectabilis CCTCC M2017417 has led to the characterization of streptovaricins as potent compounds against methicillin-resistant Staphylococcus aureus (MRSA). We identified the streptovaricin biosynthetic gene cluster from S. spectabilis CCTCC M2017417 based on genomic sequencing and bioinformatic analysis. Targeted in-frame deletion of five cytochrome P450 genes (stvP1-P5) resulted in the identification of four new streptovaricin analogues and revealed the functions of these genes as follows: stvP1, stvP4, and stvP5 are responsible for the hydroxylation of C-20, Me-24, and C-28, respectively. stvP2 is possibly involved in formation of the methylenedioxy bridge, and stvP3, a conserved gene found in the biosynthetic cluster for naphthalenic ansamycins, might be related to the formation of a naphthalene ring. Biochemical verification of the hydroxylase activity of StvP1, StvP4, and StvP5 was performed, and StvP1 showed unexpected biocatalytic specificity and promiscuity. More importantly, anti-MRSA studies of streptovaricins and derivatives revealed significant structure-activity relationships (SARs): The hydroxyl group at C-28 plays a vital role in antibacterial activity. The hydroxyl group at C-20 substantially enhances activity in the absence of the methoxycarbonyl side chain at C-24, which can increase the activity regardless of the presence of a hydroxyl group at C-20. The inner lactone ring between C-21 and C-24 shows a positive effect on activity. This work provides meaningful information on the SARs of streptovaricins and demonstrates the utility of the engineering of streptovaricins to yield novel anti-MRSA molecules.
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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 ╳
