{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 415505608 | Name = Medicarpin | ImageFile = Medicarpin structure.svg | ImageName = Chemical structure of medicarpin | ImageAlt = Chemical structure of medicarpin | IUPACName = 9-Methoxy-6a,11a-dihydro-6''H''-[1]benzofuro[3,2-c]chromen-3-ol | OtherNames = 3-Hydroxy-9-methoxypterocarpan |Section1={{Chembox Identifiers | CASNo = 32383-76-9 | CASNo_Ref = {{cascite|correct|??}} | CASNoOther = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6TX086I6IG | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 238823 | PubChem = 623060 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 100 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C10503 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 298082 | SMILES = COC1=CC2=C(C=C1)[C@@H]3COC4=C([C@@H]3O2)C=CC(=C4)O | 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 | InChIKey = NSRJSISNDPOJOP-BBRMVZONBK | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = NSRJSISNDPOJOP-BBRMVZONSA-N | MeSHName = }} |Section2={{Chembox Properties | Formula = C<sub>16</sub>H<sub>14</sub>O<sub>4</sub> | MolarMass = 270.27 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Medicarpin''' is a pterocarpan, a derivative of isoflavonoids.
== Natural occurrences == Medicarpin is found in ''Medicago truncatula'' and ''Swartzia madagascariensis''. It can also be found in ''Maackia amurensis'' cell cultures.<ref>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}}</ref>
The root nodule formation by ''Sinorhizobium meliloti''<ref name="Dakora">{{cite journal | vauthors = Dakora FD, Joseph CM, Phillips DA | title = Alfalfa (''Medicago sativa'' L.) Root Exudates Contain Isoflavonoids in the Presence of ''Rhizobium meliloti''. | journal = Plant Physiol. | volume = 101 | issue = 3| pages = 819–824 | year = 1993 | doi = 10.1104/pp.101.3.819 | pmc = 158695| pmid = 12231731}}</ref> is apparently dependent on the flavonoids pathway.<ref>{{cite journal | last1=Wasson | first1=A. P. | title=Silencing the Flavonoid Pathway in Medicago truncatula Inhibits Root Nodule Formation and Prevents Auxin Transport Regulation by Rhizobia | journal=The Plant Cell Online | volume=18 | pages=1617–1629 | year=2006 | issue=7 | doi=10.1105/tpc.105.038232| pmc=1488924 | pmid=16751348| bibcode=2006PlanC..18.1617W }}</ref>
== Metabolism == Pterocarpin synthase has 3 substrates : medicarpin, NADP<sup>+</sup> and H<sub>2</sub>O, and 3 products : vestitone, NADPH and H<sup>+</sup>.<ref>{{cite journal | url = http://www.jbc.org/content/269/35/22372.full.pdf+html | title = 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 | author = Lining Guo, Richard A. Dixon and Nancy L. Paival | journal = Journal of Biological Chemistry | volume = 269 | issue = 35 | pages = 22372–22378 | year = 1994 | doi = 10.1016/S0021-9258(17)31799-4 | pmid = 8071365 | doi-access = free }}</ref>
500px|left|Pterocarpin synthase reaction{{clear left}}
== References == {{reflist}}
{{Pterocarpan}}
Category:Pterocarpans Category:Methoxy compounds
{{aromatic-stub}}