IB-00208
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| Category | Antibiotics |
| Catalog number | BBF-03589 |
| CAS | |
| Molecular Weight | 658.65 |
| Molecular Formula | C36H34O12 |
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Description
IB-00208, a new cytotoxic polycyclic xanthone produced by Actinomadura sp. It also has anti-Gram-positive bacteria activity (MIC=0.09-1.4 nmol/L).
Specification
| IUPAC Name | 3-hydroxy-19,22-dimethoxy-10-(4-methoxy-3,5,6-trimethyloxan-2-yl)oxy-7-methyl-6,17-dioxahexacyclo[12.12.0.02,11.04,9.016,25.018,23]hexacosa-1(14),2(11),3,9,12,16(25),18,20,22-nonaene-5,15,24,26-tetrone |
| Canonical SMILES | CC1CC2=C(C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C(=O)C6=C(C=CC(=C6O5)OC)OC)C(=C2C(=O)O1)O)OC7C(C(C(C(O7)C)C)OC)C |
| InChI | InChI=1S/C36H34O12/c1-13-12-19-24(35(41)45-13)28(38)23-18(32(19)48-36-15(3)31(44-7)14(2)16(4)46-36)9-8-17-22(23)29(39)26-30(40)25-20(42-5)10-11-21(43-6)33(25)47-34(26)27(17)37/h8-11,13-16,31,36,38H,12H2,1-7H3 |
| InChI Key | VOUCFZRNPMNYDQ-UHFFFAOYSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 890.1±65.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Approaches to polycyclic 1,4-dioxygenated xanthones. Application to total synthesis of the aglycone of IB-00208
Jingyue Yang, Daniel Knueppel, Bo Cheng, Douglas Mans, Stephen F Martin Org Lett. 2015 Jan 2;17(1):114-7. doi: 10.1021/ol503336t. Epub 2014 Dec 16.
Hexacyclic xanthone natural products such as IB-00208 present a formidable challenge in organic synthesis. A new approach to polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones has been developed and applied to the first total synthesis of the aglycone of IB-00208. The 22-step synthesis features an acetylide stitching process that joins an aryl aldehyde with an angularly fused benzocyclobutenone, which was prepared by a ring-closing metathesis reaction. The resulting acetylenic benzocyclobutenone diol underwent a Moore rearrangement to give an intermediate that was further elaborated to the aglycone of IB-00208 as a mixture of hydroquinone-quinone tautomers.
2. Total Synthesis of the Aglycone of IB-00208
Daniel Knueppel, Jingyue Yang, Bo Cheng, Douglas Mans, Stephen F Martin Tetrahedron. 2015 Sep 2;71(35):5741-5757. doi: 10.1016/j.tet.2015.05.024.
A total synthesis of the aglycone of IB-00208 was accomplished in 22 steps using a newly developed approach towards polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones. The generality of this entry to xanthones was initially established on several model systems before it was successfully applied to the construction of the hexacyclic core of the natural product. A new and potentially general approach towards angularly-fused benzocyclobutenones using ring-closing metathesis (RCM) was also developed.
3. IB-00208, a new cytotoxic polycyclic xanthone produced by a marine-derived Actinomadura. I. Isolation of the strain, taxonomy and biological activites
Leyre Malet-Cascón, Francisco Romero, Fernando Espliego-Vázquez, Dolores Grávalos, José Luis Fernández-Puentes J Antibiot (Tokyo). 2003 Mar;56(3):219-25. doi: 10.7164/antibiotics.56.219.
A new compound, IB-00208, has been isolated from the fermentation broth of an actinomycete isolated from a marine environment. The strain was identified as Actinomadura sp. by its chemical and phylogenetic characteristics. The compound shows cytotoxic activity on tumor cell lines and bactericidal activity against gram-positive bacteria.
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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 ╳
