bipinnatin J
{{Chembox
| ImageFile = Bipinnatin J.png
| ImageSize =
| ImageAlt =
| IUPACName = (2Z,5S,11S,12S)-12-Hydroxy-11-isopropenyl-3,14-dimethyl-6,16-dioxatricyclo[11.2.1.15,8]heptadeca-1(15),2,8(17),13-tetraen-7-one
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 201742-79-2
| PubChem = 5470115
| ChemSpiderID = 10213404
| ChEMBL = 401906
| SMILES = Cc1cc/2oc1[C@H]([C@@H](CCC3=C[C@H](C/C(=C2)/C)OC3=O)C(=C)C)O
| InChI = 1S/C20H24O4/c1-11(2)17-6-5-14-10-16(24-20(14)22)8-12(3)7-15-9-13(4)19(23-15)18(17)21/h7,9-10,16-18,21H,1,5-6,8H2,2-4H3/b12-7-/t16-,17-,18-/m0/s1
| InChIKey = RCFMTOJVVOOMTO-PVUOXGCVSA-N}}
|Section2={{Chembox Properties
| Formula = | C=20 | H=24 | O=4
| MolarMass = 328.40216
| Appearance =
| Density =
| MeltingPtC = 140 to 142
| MeltingPt_notes =
| BoilingPt =
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Bipinnatin J is a diterpene isolated from the bipinnate sea plume Antillogorgia bipinnata, a sea fan found in the eastern Caribbean Sea.{{cite journal |author1=Rodriguez, A. D. |author2=Shi, J.-G. | title = The First Cembrane-Pseudopterane Cycloisomerization | journal = J. Org. Chem. | year = 1998 | volume = 63 | issue = 2 | pages = 420–421 | doi = 10.1021/jo971884g}} It is one of the structurally simplest of the furanocembrenolides, and is speculated to be a biosynthetic precursor to a wide array cembrenolides along with the dehydroxylated analog, rubifolide.{{cite journal |author1=Roethle, P. A. |author2=Trauner, D. | title = The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products | journal = Nat. Prod. Rep. | year = 2008 | volume = 25 | issue = 2 | pages = 298–317 | doi = 10.1039/b705660p | pmid = 18389139}}
Biosynthesis
Although the exact biosynthesis of bipinnatin J has not been formally studied, the biosynthesis the core cembrane skeleton, neo-cembrene, has been extensively studied. Starting from geranylgeranyl pyrophosphate, the pyrophosphate leaves, creating the allyl carbocation. A type A cyclization then yields the 14-membered cembrane ring with the isopropyl cation outside the ring. Proton elimination then yields neo-cembrene.{{cite journal |author1=MacMillan, J. |author2=Beale, M. H. | title = Diterpene Biosynthesis | journal = Comprehensive Natural Products Chemistry| year = 1999 | volume = 2 | pages = 217–243 }} From this point, the biosynthesis of bipinnatin J is speculative. Oxidation, most likely utilizing P450 monooxygenases, followed by ring closure creates both the furan and butenolide within the 14-membered ring. ∆ double bond isomerization of the C7-C8 olefin then occurs to afford the Z conformation, yielding rubifolide. Another oxidation of C2 then yields bipinnatin J.
References
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