Saquayamycin A1
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| Category | Antibiotics |
| Catalog number | BBF-03451 |
| CAS | 99260-66-9 |
| Molecular Weight | 596.58 |
| Molecular Formula | C31H32O12 |
| Purity | 95% |
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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 | 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]-â-Darabino-hexopyranosyl]-3,4,4a,12b-tetrahydro-3,4a,8,12b-tetrahydroxy-3-methyl-, (3R,4aR,12bS)-; (3R)-9-[4-O-[(2R,6S)-5,6-Dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-2,6-dideoxy-β-D-arabino-hexopyranosyl]-3,4,4a,12b-tetrahydro-3α,4aα,8,12bα-tetrahydroxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione |
| IUPAC Name | (3R,4aR,12bS)-3,4a,8,12b-tetrahydroxy-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-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1C(C(CC(O1)C2=C(C3=C(C=C2)C(=O)C4=C(C3=O)C=CC5(C4(C(=O)CC(C5)(C)O)O)O)O)O)OC6C=CC(=O)C(O6)C |
| InChI | InChI=1S/C31H32O12/c1-13-18(32)6-7-22(42-13)43-28-14(2)41-20(10-19(28)33)15-4-5-16-23(25(15)35)26(36)17-8-9-30(39)12-29(3,38)11-21(34)31(30,40)24(17)27(16)37/h4-9,13-14,19-20,22,28,33,35,38-40H,10-12H2,1-3H3/t13-,14+,19+,20+,22-,28+,29-,30-,31-/m0/s1 |
| InChI Key | XVKBERYQCGDFEY-ABMGXXCISA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria; Neoplastics (Tumor) |
| Melting Point | 166-168°C |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Derivatives of saquayamycins A and B. Regio- and diastereoselective addition of alcohols to the L-aculose moiety
T Henkel, A Zeeck J Antibiot (Tokyo). 1990 Jul;43(7):830-7. doi: 10.7164/antibiotics.43.830.
In continuation of our structure-activity investigations on angucycline antibiotics we prepared derivatives of saquayamycins A (1) and B (4) by regio- and diastereoselective nucleophilic addition of different alcohols to the L-aculose moiety. Reversible protection of the 4'-hydroxy group in 1 by silylation allowed a derivatization at both L-aculose moieties without cyclization towards cinerulose B. The in vitro cytotoxic activity remained almost unchanged after variation at the L-aculose moieties whereas a change in the aglycone structure led to a total loss of the biological activity.
2. Identification of inhibitors of inducible nitric oxide synthase from microbial extracts
K A Alvi, D D Baker, V Stienecker, M Hosken, B G Nair J Antibiot (Tokyo). 2000 May;53(5):496-501.
A new member of the angucycline family, vineomycin C (3), together with four known metabolites saquayamycin A1 (1), A-7884 (2), rabelomycin (5) and xanthomegnin (6) were isolated from microbial extracts. The structures were determined by 1D and 2D NMR techniques and chemical degradation. Compounds 1-3 and 5 were isolated from a fermentation of Streptomyces sp., while 6 was isolated from a fungal fermentation extract. All five compounds have shown potent inhibitory activity in the inducible nitric oxide synthase (iNOS) assay.
3. Cytotoxic rearranged angucycline glycosides from deep sea-derived Streptomyces lusitanus SCSIO LR32
Xiangcheng Zhu, Yanwen Duan, Zhaomeng Cui, Zhen Wang, Zengxia Li, Yun Zhang, Jianhua Ju, Hongbo Huang J Antibiot (Tokyo). 2017 Jul;70(7):819-822. doi: 10.1038/ja.2017.17. Epub 2017 Feb 22.
Two new rearranged linear angucycline glycosides, designated grincamycins G and H (1 and 2), together with three known congers P-1894B (vineomycin A1, 3), saquayamycin B (4) and vineomycin B2 (5), were obtained from marine-derived actinomycete Streptomyces lusitanus SCSIO LR32. The structures of 1 and 2 were elucidated by MS, 1D and 2D NMR techniques. Compounds 2-5 showed significant inhibitory effect on Jurkat T-cell proliferation with IC50 values of 3.0, 0.011, 0.037 and 0.3 μM, respectively.
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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 ╳
