:Phellamurin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 414762841

| Name = Phellamurin

| ImageFile = Phellamurin.svg

| ImageSize = 200px

| IUPACName = (2R,3R)-7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one

| SystematicName = (2R,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-4H-1-benzopyran-4-one

| OtherNames = Fellavine
8-Prenyldihydrokaempferol 7-glucoside
Epimedoside C

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 52589-11-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII =UXB86HY2NK

| PubChem = 193876

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 8048

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 168247

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C09808

| MeSHName = C016043

| SMILES = CC(=CCC1=C(C=C(C2=C1O[C@@H]([C@H](C2=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C

| InChI = 1/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1

| InChIKey = GRDZTDZJQRPNCN-YIANMRPHBT

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GRDZTDZJQRPNCN-YIANMRPHSA-N

}}

|Section2={{Chembox Properties

| C=26 | H=30 | O=11

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavan-on-ol Aromadendrin,{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Phellamurin | title=Phellamurin}} and may be seen as the 7-O-glucoside of noricaritin.{{Cite book |title=Fortschritte der Chemie Organischer Naturstoffe |date=6 December 2012 |isbn=978-3709180525 |page=17|publisher=Springer }} Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible.

It can be found in Commiphora africana{{cite journal | url=http://pubs.acs.org/doi/abs/10.1021/np0400510 | doi=10.1021/np0400510 | title=A Dihydroflavonol Glucoside from Commiphora a fricana that Mediates DNA Strand Scission | year=2005 | last1=Ma | first1=Ji | last2=Jones | first2=Shannon H. | last3=Hecht | first3=Sidney M. | journal=Journal of Natural Products | volume=68 | issue=1 | pages=115–117 | pmid=15679332 | bibcode=2005JNAtP..68..115M }} and in Phellodendron amurense.{{cite journal | url=https://doi.org/10.1007%2FBF02035150 | doi=10.1007/BF02035150 | title=A flavonoid glucoside, phellamurin, regulates differential oviposition on a rutaceous plant,Phellodendron amurense, by two sympatric swallowtail butterflies,Papilio protenor andP. Xuthus: The front line of a coevolutionary arms race? | year=1995 | last1=Honda | first1=Keiichi | last2=Hayashi | first2=Nanao | journal=Journal of Chemical Ecology | volume=21 | issue=10 | pages=1531–1539 | pmid=24233681 | bibcode=1995JCEco..21.1531H | s2cid=8258780 }}