Arisostatin A
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| Category | Antibiotics |
| Catalog number | BBF-00082 |
| CAS | 271574-41-5 |
| Molecular Weight | 1341.53 |
| Molecular Formula | C69H100N2O24 |
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Description
Arisostatin A is a Tetrocarcin antibiotic produced by Micromonospora sp. TP-A0316. It has anti-Gram-positive bacteria activity, anti-Bacillus subtilis and anti-tumor activity.
Specification
| IUPAC Name | [(2S,3S,4R,6R)-6-[[(1S,9S,11E,13S,16S,17S,18S,20S,21R,22S)-3-formyl-5,23-dihydroxy-9-[(2R,4S,5S,6R)-5-(methoxycarbonylamino)-4,6-dimethyl-4-nitrooxan-2-yl]oxy-8,12,18,20,22-pentamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-3,6,11,14,23-pentaen-17-yl]oxy]-4-[(2S,5R,6S)-5-[(2S,4R,5R,6S)-4-hydroxy-5-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-methyloxan-3-yl] 2-methylpropanoate |
| Canonical SMILES | CC1CC(C(C2C1C3(C(C=C2)C(=CCC(C(C=C4C(C=C(CC45C(=O)C(=C3O)C(=O)O5)C=O)O)C)OC6CC(C(C(O6)C)NC(=O)OC)(C)[N+](=O)[O-])C)C)OC7CC(C(C(O7)C)OC(=O)C(C)C)OC8CCC(C(O8)C)OC9CC(C(C(O9)C)OC1CCC(C(O1)C)O)O)C |
| InChI | InChI=1S/C69H100N2O24/c1-31(2)64(78)94-60-39(10)87-54(27-50(60)91-51-22-20-49(37(8)85-51)90-53-26-47(75)59(38(9)86-53)92-52-21-18-45(73)36(7)84-52)93-58-35(6)23-34(5)57-42(58)16-17-43-32(3)15-19-48(89-55-29-67(12,71(81)82)61(40(11)88-55)70-66(80)83-14)33(4)24-44-46(74)25-41(30-72)28-69(44)63(77)56(65(79)95-69)62(76)68(43,57)13/h15-17,24-25,30-31,33-40,42-43,45-55,57-61,73-76H,18-23,26-29H2,1-14H3,(H,70,80)/b32-15+,44-24?,62-56?/t33?,34-,35-,36-,37-,38-,39-,40+,42-,43-,45+,46?,47+,48-,49+,50+,51-,52-,53-,54-,55-,57+,58-,59-,60-,61+,67-,68+,69-/m0/s1 |
| InChI Key | IHCWKKWXFVWBDU-VYCOSBPHSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
Reference Reading
1. Tetrocarcin Q, a New Spirotetronate with a Unique Glycosyl Group from a Marine-Derived Actinomycete Micromonospora carbonacea LS276
Ting Gong, Xin Zhen, Xing-Lun Li, Jing-Jing Chen, Tian-Jiao Chen, Jin-Ling Yang, Ping Zhu Mar Drugs. 2018 Feb 24;16(2):74. doi: 10.3390/md16020074.
A new spirotetronate glycoside tetrocarcin Q (1) and six known analogues tetrocarcin A (2), AC6H (3), tetrocarcin N (4), tetrocarcin H (5), arisostatin A (6), and tetrocarcin F1 (7) were isolated from the fermentation broth of the marine-derived actinomycete Micromonospora carbonacea LS276. Their chemical structures were established on the basis of 1D- and 2D-NMR spectroscopy, as well as HR-ESI-MS analysis. The absolute configurations of their stereogenic carbons were determined by circular dichroism (CD) analysis. Compound 1 possesses 2-deoxy-allose, which is a unique sugar type at the C-9 position. This type has not been found in the previously reported spirotetronate glycosides. Compound 1 displayed moderate antibacterial activity against Bacillus subitlis ATCC 63501 with minimum inhibitory concentration (MIC) value of 12.5 μM.
2. Arisostatins A induces apoptosis through the activation of caspase-3 and reactive oxygen species generation in AMC-HN-4 cells
Young-Ho Kim, Ho Cheol Shin, Dal Won Song, Sung-Hee Lee, Tamotsu Furumai, Jong-Wook Park, Taeg Kyu Kwon Biochem Biophys Res Commun. 2003 Sep 19;309(2):449-56. doi: 10.1016/j.bbrc.2003.07.009.
A microbial secondary metabolite, arisostatins A (As-A), was originally discovered as a substance carrying the antibiotic activity against Gram-positive bacteria and shown to possess potent anti-tumor properties. The mechanism by which arisostatins A initiates apoptosis remains poorly understood. In the present report we investigated the effect of arisostatins A on activation of the apoptotic pathway in HN-4 cells. Arisostatins A was shown to be responsible for the inhibition of HN-4 cell growth by inducing apoptosis. Treatment with 4 microM arisostatins A for 24h produced morphological features of apoptosis and DNA fragmentation in HN-4 cells. Arisostatins A caused dose-dependent apoptosis and DNA fragmentation of HN-4 cells used as a model. Treatment with caspase inhibitor significantly reduced the arisostatins A-induced caspase 3 activation. In addition, arisostatins A-induced apoptosis was associated with the generation of reactive oxygen species (ROS), which was prevented by an antioxidant NAC (N-acetyl-cysteine). These data indicate that cytotoxic effect of arisostatins A on HN-4 cells is attributable to the induced apoptosis and that arisostatins A-induced apoptosis is mediated by caspase-3 activation pathway, loss of mitochondrial transmembrane potential (DeltaPsi(m)), and release of cytochrome c into cytosol.
3. Arisostatins A and B, new members of tetrocarcin class of antibiotics from Micromonospora sp. TP-A0316. II. Structure determination
Y Igarashi, K Takagi, Y Kan, K Fujii, K Harada, T Furumai, T Oki J Antibiot (Tokyo). 2000 Mar;53(3):233-40. doi: 10.7164/antibiotics.53.233.
Structures of arisostatins A and B were determined by spectroscopic analyses. Arisostatins were found to be new analogs of tetrocarcin A and possess an iso-butanoyldigitoxose unit instead of the acetyldigitoxose one. NMR analyses of arisostatins and tetrocarcin A led to the revision of the anomeric configurations in the tetrasaccharide moiety of tetrocarcin A.
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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 ╳
