codinaeopsin
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| Watchedfields = changed
| verifiedrevid = 440195685
| ImageFile = Codinaeopsin.svg
| ImageSize =
| IUPACName = 5-((1H-indol-3-yl)methyl)-3-((1R,2R,4aS,6R,8S,8aS)-2-((E)-but-2-en-2-yl)-4a,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-hydroxy-1H-pyrrol-2(5'H)-one
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|Section1={{Chembox Identifiers
| CASNo = 1055291-88-7
| ChEBI = 222711
| PubChem = 102412273
| ChemSpiderID = 129562509
| SMILES = C/C=C(\C)/[C@H]1[C@H]([C@@H]2[C@H](C[C@H](C[C@]2(C=C1C)C)C)C)C(=O)C3=CC(NC3=O)(CC4=CNC5=CC=CC=C54)O
| StdInChI = 1S/C32H40N2O3/c1-7-19(3)26-21(5)14-31(6)13-18(2)12-20(4)28(31)27(26)29(35)24-16-32(37,34-30(24)36)15-22-17-33-25-11-9-8-10-23(22)25/h7-11,14,16-18,20,26-28,33,37H,12-13,15H2,1-6H3,(H,34,36)/b19-7+/t18-,20+,26-,27-,28+,31+,32?/m1/s1
| StdInChIKey = FFIWOIAVVDGNHZ-ZQXRKGDHSA-N
}}
|Section2={{Chembox Properties
| C=32 | H=40 | N=2 | O=3
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|Section3={{Chembox Hazards
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Codinaeopsin is an antimalarial alkaloid isolated from a endophytic mold found in Vochysia trees in Costa Rica. It is reported to have bioactivity against Plasmodium falciparum with an IC50 = 2.3 μg/mL (4.7 μM). Pure codinaeopsin was reported to be isolated with a total yield of 18 mg/mL from cultured fungus.{{cite journal|last=Kontnik|first=Renee|year=2008|title=Codinaeopsin, an Antimalarial Fungal Polyketide|journal=Org. Lett.|volume=10|issue=18|pages=4149–4151|doi=10.1021/ol801726k|author2=Clardy, Jon|pmid=18698786|authorlink2=Jon Clardy|pmc=2626159}} The biosynthesis of codinaeopsin involves a polyketide synthase-nonribosomal peptide synthetase (PKS-NRPS) hybrid.
Biosynthesis
=Formation of linear polyketide=
The first step of the biosynthesis of codinaeopsin involves the assembly of the a linear polyketide by use of seven modules and incorporation of six methylmalonyl CoAs and one malonyl CoA by polyketide synthases (type I PKSs).
=Formation of tetramic acid (2,4-pyrrolidinone)=
L-Tryptophan is introduced by a nonribosomal peptide synthetase (NRPS) module and results in the central heterocyclic tetramic acid (2,4-pyrrolidinone). The formal oxidation-reduction is found to be achieved by a series of tautomeric shifts involving enol and imine intermediates in the ring and consistent by discovery both C-2’ epimers.
=Cyclization of PKS-assembled unit=
The PKS unit is hypothesized to cyclize by a Diels-Alder-like addition similar to other natural products such as lovastatin and solanapyrone.{{cite journal|last1=Auclair|first1=Karine|author-link1=Karine Auclair|last2=Sutherland|first2=Andrew|last3=Kennedy|first3=Jonathan|last4=Witter|first4=David J.|last5=Van den Heever|first5=Johan P.|last6=Hutchinson|first6=C. Richard|last7=Vederas|first7=John C.|title=Lovastatin Nonaketide Synthase Catalyzes an Intramolecular Diels−Alder Reaction of a Substrate Analogue|journal=Journal of the American Chemical Society|volume=122|issue=46|year=2000|pages=11519–11520|issn=0002-7863|doi=10.1021/ja003216+|bibcode=2000JAChS.12211519A }}
References
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