Costunolide

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Costunolide
Identifiers
CAS number 553-21-9 N
PubChem 5281437
ChemSpider 4444782 YesY
UNII 4IK578SA7Z YesY
MeSH (+)-Costunolide
ChEBI CHEBI:3900 YesY
ChEMBL CHEMBL205612 N
Jmol-3D images {{#if:O=C/1O[C@@H]2/C=C(/CC/C=C(/CC[C@H]2C\1=C)C)C|Image 1
Properties
Molecular formula C15H20O2
Molar mass 232.32 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

(+)-Costunolide is a naturally occurring sesquiterpene lactone, first isolated in Saussurea costus roots in 1960.[1] It is also found in lettuce.[1]

Synthesis

It is synthesized through the mevalonate pathway, seen in Figure 1. The synthesis begins with the cyclization of compound 1, farnesyl pyrophosphate (FPP), which is mediated by a sesquiterpene cyclase, (+)-germacrene A synthase, to form compound 2, (+)-germacryl cation.[1] Inside this same enzyme, a proton is lost to form 3, (+)-germacrene A.[2] The isoprenyl side chain of (+)-germacrene A is then hydroxylated by (+)-germacrene A hydroxylase, which is a cytochrome P450 enzyme, to form 4.[1] NAD(P)+ dependent hydrogenase(s) then oxidize 4, germacra-1(10),4,11(13)-trien-12-ol, through the intermediate 5, germacra-1(10),4,11(13)-trien-12-al to form compound 6, germacrene acid. The cyctochrome P450 enzyme, (+)-costunolide synthase, which is a NADPH and O2 dependent enzyme, then oxidizes germacrene acid to give the alcohol intermediate, 7, which then cyclizes to form the lactone 8, (+)-costunolide.[3]

Figure 1. Biosynthesis of (+)-Costunolide.[2]

References

  1. 1.0 1.1 1.2 1.3 Kraker, J.; Franssen, M.; Dalm, M.; Groot, A.; Bouwmeester, H. (April 2001). "Biosynthesis of Germacrene A Carboxylic Acid in Chicory Roots. Demonstration of a Cytochrome P450 (+)-Germacrene A Hydroxylase and NADP+-Dependent Sesquiterpenoid Dehydrogenase(s) Involved in Sesquiterpene Lactone Biosynthesis". Plant Physiology 125 (4): 1930–1940. doi:10.1104/pp.125.4.1930. PMC 88848. PMID 11299372. 
  2. 2.0 2.1 Dewick, Paul M. (2009). Medicinal Natural Products: A Biosynthetic Approach. West Sussex, United Kingdom: John Wiley & Sons Ltd. p. 214. 
  3. Kraker, J.; Franssen, M.; Joerink, M.; Groot, A.; Bouwmeester, H. (April 2002). "Biosynthesis of Costunolide, Dihydrocostunolide, and Leucodin. Demonstration of Cytochrome P450-Catalyzed Formation of the Lactone Ring Present in Sesquiterpene Lactones of Chicory". Plant Physiology 129: 257–258. doi:10.1104/pp.010957. PMC 155889. PMID 12011356. 
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