358:
35:
354:, which undergoes a intramolecular hetero-Diels-Alder to yield debromomarinone. Lastly, the vanadium-dependent bromoperoxidase catalyzes the bromination of debromomarinone at the C-5 position to result in the formation of marinone.
87:
379:
Pathirana C, Jensen PR, Fenical W (December 1992). "Marinone and debromomarinone: Antibiotic sesquiterpenoid naphthoquinones of a new structure class from a marine bacterium".
155:
InChI=1S/C25H27BrO5/c1-12(2)6-5-9-25(4)15-8-7-13(3)10-14(15)18-22(29)20-19(23(30)24(18)31-25)16(27)11-17(28)21(20)26/h6,10-11,14-15,27-28H,5,7-9H2,1-4H3/t14-,15+,25-/m0/s1
318:(Fig. 1). This transformation is catalyzed in vivo by NphB aromatic prenyltransferase in naphterpin biosynthesis or by CnqP3 or CnqP4 in marinone biosynthesis. Then,
572:"Studies on terpenoids produced by actinomycetes. 5-dimethylallylindole-3-carboxylic Acid and A80915G-8"-acid produced by marine-derived Streptomyces sp. MS239"
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undergoes oxidative dearomatization which is catalyzed by VCPO, which is a vanadium-dependent chloroperoxidase enzyme. This transformation yields compound
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units followed by the aromatization of the resulting pentaketide using a type III polyketide synthase. Next, THN undergoes
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63:)-11-Bromo-8,10-dihydroxy-2,5-dimethyl-5-(4-methylpent-3-enyl)-3,4,4a,12b-tetrahydronaphthoisochromene-7,12-dione
334:. Next, a VCPO catalyzed α-hydroxyketone rearrangement shifts the geranyl substituent from C-4 to C-3, yielding
346:. This is followed by the reductive halogenation of the α-chloroepoxide to yield the hydroxynaphthoquinone,
350:. Next, oxidation at the C-2 position and facile E/Z isomerization of the double bond affords the enone,
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411:"Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products"
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Murray LA, McKinnie SM, Pepper HP, Erni R, Miles ZD, Cruickshank MC, et al. (August 2018).
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then undergoes two consecutive chlorinations at the C2 position, catalyzed by VCPO, to yield
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515:"Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products"
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Motohashi K, Irie K, Toda T, Matsuo Y, Kasai H, Sue M, et al. (February 2008).
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to mildly basic conditions induces cyclization to yield the α-chloroepoxide,
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302:(THN), which is known to be biosynthesized via the condensation of five
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Except where otherwise noted, data are given for materials in their
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The proposed biosynthesis of marinone was first reported by Murray
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CC1=C2(CC1)(OC3=C2C(=O)C4=C(C3=O)C(=CC(=C4Br)O)O)(C)CCC=C(C)C
460:"Naphthoquinone-Based Meroterpenoids from Marine-Derived
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Shen X, Wang X, Huang T, Deng Z, Lin S (August 2020).
298:in 2018. The biosynthesis of marinone begins with
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623:Bioactive compounds from marine actinomycetes
513:Kuzuyama T, Noel JP, Richard SB (June 2005).
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361:Proposed biosynthetic pathway of marinone
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158:Key: DONXAKUQFKTOAJ-AYNSBQOLSA-N
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648:Heterocyclic compounds with 4 rings
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300:1,3,6,8-tetrahydroxynaphthalene
260:(at 25 °C , 100 kPa).
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314:at the C-4 position, yielding
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393:10.1016/0040-4039(93)88010-G
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663:Terpeno-phenolic compounds
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421:(34): 11009–11014.
381:Tetrahedron Letters
233: g·mol
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304:malonyl-coenzyme A
264:Infobox references
238:Related compounds
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525:(7044): 983–987.
415:Angewandte Chemie
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69:Identifiers
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653:Bromoarenes
638:Antibiotics
474:(8): 1187.
326:. Compound
188:Properties
632:Categories
464:sp. B9173"
366:References
280:antibiotic
226:Molar mass
99:ChemSpider
75:3D model (
48:IUPAC name
18:C25H27BrO5
28:Marinone
606:29628302
598:18408326
557:15959519
500:32824158
445:29935040
276:Marinone
133:10458149
548:2874460
527:Bibcode
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436:6248334
231:487.390
120:PubChem
108:8633563
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59:,12b
584:doi
543:PMC
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