Rubellin B
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| Names | |
|---|---|
| IUPAC name
(3R,3aS,10S,10aS,19cR)-3,6,10,13,15,18-hexahydroxy-8-methyl-3,3a,11,19c-tetrahydrobenzo[e]naphtho[2',3':5,6]fluoreno[1,9a-b]oxepine-5,14,19(10H)-trione
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| Properties | |
| C30H22O10 | |
| Molar mass | 542.50 g⋅mol^-1 |
| Melting point | 1428.25 [K] |
| Boiling point | 1709.77 [K] |
| Identifiers | |
3D model (
JSmol ) |
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| ChemSpider | |
PubChem CID
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| UNII | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rubellin B is a phytotoxic chemical responsible for the superoxides. The drug has not been involved in many clinical studies, but has been found to prevent tau aggregation pointing to its potential in the treatment of Alzheimer's disease.[1]
Biosynthesis
The biosynthesis of rubellins involved a Type 1
P450 enzyme, RccM,[2] which is unique in the Ramularia collo-cygni. This molecule serves as a precursor for the production of a multitude of rubellins, one being rubellin B. Continuing the pathway to rubellin B, the precursor molecule is hydroxylated by the enzyme RccD,[2] an FAD-dependent monooxygenase. The final step to rubellin B is an oxidation to a seven-membered ring by the enzyme BVMO, RccL[2]
in the drawing.
Biosynthesis of conformers
The biosynthesis of all rubellin compounds found in Ramularia collo-cygni has been reported in the literature. [2]
Natural occurrence
Rubellin occurs naturally in a number of
phytotoxic effects named as the Ramularia leaf spot disease. Initially the molecule was discovered due to its presence on a cash crop and was thus isolated from the fungus Mycospharella rubella in 1986.[3]
The compound was more recently isolated in Germany due to its presence on diseased leaves from the fungus Ramularia collo-cygni which has paved the way for the classification of the molecule's synthesis and properties.