Saquayamycin A
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| Category | Antibiotics |
| Catalog number | BBF-02878 |
| CAS | 99260-65-8 |
| Molecular Weight | 820.83 |
| Molecular Formula | C43H48O16 |
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Description
It is produced by the strain of Str. nodosus MH190-16F3. It has antimicrobial effect, but it has weaker effect against gram-negative bacteria. It has inhibitory effect on leukemia P388 cells and adriamycin-resistant P388 cells.
Specification
| Synonyms | saquayamycin; Benz[a]anthracene-1,7,12(2H)-trione, 9-[2,6-dideoxy-4-O-[(2R,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-b-D-arabino-hexopyranosyl]-3-[[(2S,5S,6S)-5-[[(2R,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-3,4,4a,12b-tetrahydro-4a,8,12b-trihydroxy-3-methyl-, (3R,4aR,12bS)-; Benz[a]anthracene-1,7,12(2H)-trione, 9-[2,6-dideoxy-4-O-[(2R-trans)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-b-D-arabino-hexopyranosyl]-3-[[5-[(5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-3,4,4a,12b-tetrahydro-4a,8,12b-trihydroxy-3-methyl-,[2S-[2a(3S*,4aS*,12bR*),5b(2S*,6R*),6b]]- |
| IUPAC Name | (3R,4aR,12bS)-4a,8,12b-trihydroxy-9-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1C(CCC(O1)OC2(CC(=O)C3(C4=C(C=CC3(C2)O)C(=O)C5=C(C4=O)C=CC(=C5O)C6CC(C(C(O6)C)OC7C=CC(=O)C(O7)C)O)O)C)OC8C=CC(=O)C(O8)C |
| InChI | InChI=1S/C43H48O16/c1-19-26(44)8-11-32(54-19)57-29-10-13-34(56-21(29)3)59-41(5)17-31(47)43(52)36-25(14-15-42(43,51)18-41)38(49)35-24(39(36)50)7-6-23(37(35)48)30-16-28(46)40(22(4)53-30)58-33-12-9-27(45)20(2)55-33/h6-9,11-12,14-15,19-22,28-30,32-34,40,46,48,51-52H,10,13,16-18H2,1-5H3/t19-,20-,21-,22+,28+,29-,30+,32-,33-,34-,40+,41-,42-,43-/m0/s1 |
| InChI Key | PSCPFFPJZFSAMI-USAPNZCCSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria; Neoplastics (Tumor) |
| Boiling Point | 1003.1°C at 760 mmHg |
| Melting Point | 149-152°C |
| Density | 1.48 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Himalaquinones A-G, Angucyclinone-Derived Metabolites Produced by the Himalayan Isolate Streptomyces sp. PU-MM59
Yongyong Zhang, Mohsin T Cheema, Larissa V Ponomareva, Qing Ye, Tao Liu, Imran Sajid, Jürgen Rohr, Qing-Bai She, S Randal Voss, Jon S Thorson, Khaled A Shaaban J Nat Prod. 2021 Jul 23;84(7):1930-1940. doi: 10.1021/acs.jnatprod.1c00192. Epub 2021 Jun 25.
Himalaquinones A-G, seven new anthraquinone-derived metabolites, were obtained from the Himalayan-based Streptomyces sp. PU-MM59. The chemical structures of the new compounds were identified based on cumulative analyses of HRESIMS and NMR spectra. Himalaquinones A-F were determined to be unique anthraquinones that contained unusual C-4a 3-methylbut-3-enoic acid aromatic substitutions, while himalaquinone G was identified as a new 5,6-dihydrodiol-bearing angucyclinone. Comparative bioactivity assessment (antimicrobial, cancer cell line cytotoxicity, impact on 4E-BP1 phosphorylation, and effect on axolotl embryo tail regeneration) revealed cytotoxic landomycin and saquayamycin analogues to inhibit 4E-BP1p and inhibit regeneration. In contrast, himalaquinone G, while also cytotoxic and a regeneration inhibitor, did not affect 4E-BP1p status at the doses tested. As such, this work implicates a unique mechanism for himalaquinone G and possibly other 5,6-dihydrodiol-bearing angucyclinones.
2. Saquayamycin B1 Suppresses Proliferation, Invasion, and Migration by Inhibiting PI3K/AKT Signaling Pathway in Human Colorectal Cancer Cells
Jianjiang Li, Ningning Han, Hao Zhang, Xiaoyu Xie, Yaoyao Zhu, E Zhang, Jiahui Ma, Chuangeng Shang, Mengxiong Yin, Weidong Xie, Xia Li Mar Drugs. 2022 Sep 7;20(9):570. doi: 10.3390/md20090570.
Moromycin B (Mor B), saquayamycin B1 (Saq B1), saquayamycin B (Saq B), and landomycin N (Lan N), four angucyclines produced by the marine-derived actinomycete Streptomyces sp., are a class of polyketone compounds containing benzanthracene. Here, the structure-activity relationship of these four compounds was analyzed in human colorectal cancer (CRC) cells. Saq B1, which showed the strongest cytotoxicity with an IC50 of 0.18-0.84 µM for CRC cells in MTT assays, was employed to test underlying mechanisms of action in SW480 and SW620 cells (two invasive CRC cell lines). Our results showed that Saq B1 inhibited CRC cell proliferation in a dose- and time-dependent manner. Notably, lower cytotoxicity was measured in normal human hepatocyte cells (QSG-7701). Furthermore, we observed proapoptosis, antimigration, and anti-invasion activities of Saq B1 in CRC cells. At the same time, the protein and mRNA expression of important markers related to the epithelial-mesenchymal transition (EMT) and apoptosis changed, including N-cadherin, E-cadherin, and Bcl-2, in Saq B1-treated CRC cells. Surprisingly, the PI3K/AKT signaling pathway was shown to be involved in Saq B1-induced apoptosis, and in inhibiting invasion and migration. Computer docking models also suggested that Saq B1 might bind to PI3Kα. Collectively, these results indicate that Saq B1 effectively inhibited growth and decreased the motor ability of CRC cells by regulating the PI3K/AKT signaling pathway, which provides more possibilities for the development of drugs in the treatment of CRC.
3. Enhancement of angucycline production by combined UV mutagenesis and ribosome engineering and fermentation optimization in Streptomyces dengpaensis XZHG99T
Yumei Li, Jiyu Li, Zhengmao Ye, Lingchao Lu Prep Biochem Biotechnol. 2021;51(2):173-182. doi: 10.1080/10826068.2020.1805754. Epub 2020 Aug 20.
Strain improvement of Streptomyces dengpaensis XZHG99T was performed by combined UV mutagenesis and ribosome engineering, as well as fermentation optimization for enhanced angucycline production (rabelomycin and saquayamycin B1). First, four streptomycin-resistant mutants were obtained after screening of UV mutagenesis and ribosome engineering. Then a rpsL mutant (HTT7) with higher productivity of rabelomycin and saquayamycin B1 was selected according to genetic screening and HPLC/LC-MS analyses, whose maximum titers of rabelomycin and saquayamycin B1 were 3.6 ± 0.02 mg/L and 7.5 ± 0.04 mg/L, respectively, about fourfold higher than those produced by XZHG99T. Next, fermentation optimization of HTT7 was successively carried out by single-factor experiments in shake flasks. The titers of rabelomycin and saquayamycin B1 were increased to 11.2 ± 0.04 mg/L and 20.5 ± 0.02 mg/L after optimization of shake flask fermentation conditions, respectively, which was increased about sixfold compared with those produced by XZHG99T. Finally, the titers of rabelomycin and saquayamycin B1 reached 15.7 ± 0.05 mg/L and 39.9 ± 0.05 mg/L after the scaled-up fermentation, which was 7.8-fold and 11.4-fold higher than those produced by XZHG99T, respectively. These data demonstrate that the combined empirical strain-breeding approaches are still an effective and convenient pathway to improve strain production ability.
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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 ╳
