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| Names | |
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| Preferred IUPAC name
(4aR,5S,12bS)-8,10-Dihydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4a,5,12b-tetrahydro-4H-naphtho[2,3-c][2]benzopyran-7,12-dione | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C25H28O5 | |
| Molar mass | 408.494 g·mol−1 |
| Related compounds | |
Related compounds |
Marinone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Debromomarinone is a chemical compound isolated from marine actinomycetes.[2]
The proposed biosynthesis of marinone was first reported by Murray et al. in 2018.[3] The biosynthesis of marinone begins with 1,3,6,8-tetrahydroxynaphthalene (THN), which is known to be biosynthesized via the condensation of five malonyl-coenzyme A units followed by the aromatization of the resulting pentaketide using a type III polyketide synthase.[4] Next, THN undergoes geranylationorfarnesylation at the C-4 position, yielding 1 (Fig. 1). This transformation is catalyzed in vivo by NphB aromatic prenyltransferase in naphterpin biosynthesis[5] or by CnqP3 or CnqP4 in marinone biosynthesis.[6] Then, 1 undergoes oxidative dearomatization which is catalyzed by VCPO, which is a vanadium-dependent chloroperoxidase enzyme. This transformation yields compound 2. Compound 2 then undergoes two consecutive chlorinations at the C2 position, catalyzed by VCPO, to yield 4. Next, a VCPO catalyzed α-hydroxyketone rearrangement shifts the geranyl substituent from C-4 to C-3, yielding 5. Exposure of 5 to mildly basic conditions induces cyclization to yield the α-chloroepoxide, 6. This is followed by the reductive halogenation of the α-chloroepoxide to yield the hydroxynaphthoquinone, 7. Next, oxidation at the C-2 position and facile E/Z isomerization of the double bond affords the enone, 8, which undergoes a intramolecular hetero-Diels-Alder to yield debromomarinone.
