Phellamurin

Phellamurin
Names

IUPAC name (2R,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Other names Fellavine 8-Prenyl dihydrokaempferol 7-glucoside Epimedoside C
Identifiers
CAS Number	52589-11-4^Y
ChEBI	CHEBI:8048^N
ChemSpider	168247^N
Jmol interactive 3D	Image
KEGG	C09808^N
MeSH	C016043
PubChem	193876
InChI InChI=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^N Key: GRDZTDZJQRPNCN-YIANMRPHSA-N^N 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 Key: GRDZTDZJQRPNCN-YIANMRPHBT
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
Properties
Chemical formula	C₂₆H₃₀O₁₁
Molar mass	518.52 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Phellamurin is a flavanonol, a type of flavonoid. It can be found in Commiphora africana^[1] and in Phellodendron amurense.^[2]

Related compounds

6"′-O-acetyl phellamurin is found in the leaves of Phellodendron japonicum.^[3]

References

↑ A Dihydroflavonol Glucoside from Commiphora africana that Mediates DNA Strand Scission, Ji Ma, Shannon H. Jones, and Sidney M. Hecht, 2005
↑ A flavonoid glucoside, phellamurin, regulates differential oviposition on a rutaceous plant, Phellodendron amurense, by two sympatric swallowtail butterflies, Papilio protenor and P. xuthus: The front line of a coevolutionary arms race? Keiichi Honda and Nanao Hayashi, 1995
↑ Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity, Chih-Yang Chiu, Chia-Ying Li, Chao-Chen Chiu, Masatake Niwa, Susumu Kitanaka, Amooru Gangaiah Damu, E-Jian Lee and Tian-Shung Wu, 2005

Flavanonols and their glycosides

3-Hydroxyflavanones:	Ampelopsin (Dihydromyricetin) Aromadedrin (Dihydrokaempferol) Dihydrogossypetin Dihydromorin Fustin (Dihydrofisetin) Garbanzol Taxifolin (Dihydroquercetin)

O-methylated flavanonols	Dihydrokaempferide

dihydroflavonol 3-O-glycosides	Lecontin (+)-fustin glucoside

Glycosides	Astilbin Chrysandroside A Chrysandroside B Engeletin Eucryphin Smitilbin (Isoastilbin B) Xeractinol

Acetylated glycosides	Phellamurin

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