Medicarpin

Medicarpin is a pterocarpan, a derivative of isoflavonoids.

Medicarpin
Chemical structure of medicarpin
Names
IUPAC name
9-Methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol
Other names
3-Hydroxy-9-methoxypterocarpan
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m0/s1 ☒N
    Key: NSRJSISNDPOJOP-BBRMVZONSA-N ☒N
  • InChI=1/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3/t13-,16-/m0/s1
    Key: NSRJSISNDPOJOP-BBRMVZONBK
  • COC1=CC2=C(C=C1)[C@@H]3COC4=C([C@@H]3O2)C=CC(=C4)O
Properties
C16H14O4
Molar mass 270.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Natural occurrences

Medicarpin is found in Medicago truncatula and Swartzia madagascariensis. It can also be found in Maackia amurensis cell cultures.[1]

The root nodule formation by Sinorhizobium meliloti[2] is apparently dependent on the flavonoids pathway.[3]

Metabolism

Pterocarpin synthase has 3 substrates : medicarpin, NADP+ and H2O, and 3 products : vestitone, NADPH and H+.[4]

Pterocarpin synthase reaction
Pterocarpin synthase reaction

References
  1. Isoflavonoid production by callus cultures of Maackia amurensis. S.A Fedoreyev, T.V Pokushalov, M.V Veselova, L.I Glebko, N.I Kulesh, T.I Muzarok, L.D Seletskaya, V.P Bulgakov and Yu.N Zhuravlev, Fitoterapia, 1 August 2000, Volume 71, Issue 4, Pages 365–372, doi:10.1016/S0367-326X(00)00129-5
  2. Dakora FD, Joseph CM, Phillips DA (1993). "Alfalfa (Medicago sativa L.) Root Exudates Contain Isoflavonoids in the Presence of Rhizobium meliloti". Plant Physiol. 101 (3): 819–824. doi:10.1104/pp.101.3.819. PMC 158695. PMID 12231731.
  3. 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 (7): 1617–1629. doi:10.1105/tpc.105.038232. PMC 1488924. PMID 16751348.
  4. 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. doi:10.1016/S0021-9258(17)31799-4. PMID 8071365.


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