Medicarpin

Medicarpin
Medicarpin
Chemical structure of medicarpin
IUPAC name
9-Methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2‑c]chromen-3-ol
Other names
3-Hydroxy-9-methoxypterocarpan
Identifiers
CAS number 32383-76-9 YesY
PubChem 623060
ChEMBL CHEMBL238823 N
Jmol-3D images Image 1
Properties
Molecular formula C16H14O4
Molar mass 270.27 g/mol
Exact mass 270.089209 u
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Medicarpin is a pterocarpan, a derivative of isoflavonoids, found in Medicago truncatula.

The root nodule formation by Sinorhizobium meliloti[1] is apparently dependent on the flavonoids pathway.[2]

Metabolism

Pterocarpin synthase has 3 substrates : medicarpin, NADP+ and H2O, and 3 products : vestitone, NADPH and H+.[3]

Pterocarpin synthase reaction

References

  1. ^ Dakora, F. D., Joseph, C. M., & D. A. Phillips (1993). "Alfalfa (Medicago sativa L.) Root Exudates Contain Isoflavonoids in the Presence of Rhizobium meliloti.". Plant Physiol. 101 (3): 819–824. PMC 158695. PMID 12231731. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=158695. 
  2. ^ Wasson, A. P. (2006). "Silencing the Flavonoid Pathway in Medicago truncatula Inhibits Root Nodule Formation and Prevents Auxin Transport Regulation by Rhizobia". The Plant Cell Online 18: 1617. doi:10.1105/tpc.105.038232. 
  3. ^ Lining Guo, Richard A. Dixon and Nancy L. Paival (1994). "Conversion of Vestitone to Medicarpin in Alfalfa (Medicago sativa L.) Is Catalyzed by Two Independent Enzymes. Identification, Purification, and Characterization of Vestitone Reductase and 7,2’-Dihydroxy-4’-MethoxyIsoflavanol Dehydratase". Journal of Biological Chemistry 269 (35): 22372–22378. PMID 8071365. http://www.jbc.org/content/269/35/22372.full.pdf+html. 
v · Pterocarpans:
Erybraedin C | Erythrabyssin II | Folitenol | Glycinol | Maackiain | Medicarpin | Orientanol A, B and C | Pisatin | Sophorol | Trifolirhizin
Prenylated pterocarpan:
Bitucarpin A and B | Glyceollidin I and II | Glyceollins (Glyceollin I, II, III and IV) | Glycyrrhizol A | Morisianine | Phaseolin | Striatine


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