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).
|
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 geranylation or farnesylation 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.
Names | |
---|---|
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)
|
|
ChemSpider | |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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 geranylation or farnesylation 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.