Phellamurin

Phellamurin
Names
	IUPAC name (2R,3R)-7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
	Systematic IUPAC name (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
	Other names Fellavine; 8-Prenyldihydrokaempferol 7-glucoside; Epimedoside C
Identifiers
CAS Number	52589-11-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8048 ;
ChemSpider	168247 ;
KEGG	C09808 ;
MeSH	C016043
PubChem CID	193876;
UNII	UXB86HY2NK ;
CompTox Dashboard (EPA)	DTXSID00200563 ;
	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 Key: GRDZTDZJQRPNCN-YIANMRPHSA-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	518.515 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavan-on-ol Aromadendrin,^[1] and may be seen as the 7-O-glucoside of noricaritin.^[2] 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^[3] and in Phellodendron amurense.^[4]

Related compounds

6"′-O-acetyl phellamurin is found in the leaves of Phellodendron japonicum.^[5]

References

^ "Phellamurin".
^ Fortschritte der Chemie Organischer Naturstoffe. p. 17. ISBN 370918052X.
^ Ma, Ji; Jones, Shannon H.; Hecht, Sidney M. (2005). "A Dihydroflavonol Glucoside from Commiphora a fricana that Mediates DNA Strand Scission". Journal of Natural Products. 68 (1): 115–117. doi:10.1021/np0400510. PMID 15679332.
^ Honda, Keiichi; Hayashi, Nanao (1995). "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?". Journal of Chemical Ecology. 21 (10): 1531–1539. doi:10.1007/BF02035150. PMID 24233681. S2CID 8258780.
^ Chiu, C. Y.; Li, C. Y.; Chiu, C. C.; Niwa, M.; Kitanaka, S.; Damu, A. G.; Lee, E. J.; Wu, T. S. (2005). "Constituents of leaves of Phellodendron japonicum MAXIM. And their antioxidant activity". Chemical & Pharmaceutical Bulletin. 53 (9): 1118–1121. doi:10.1248/cpb.53.1118. PMID 16141579.

External links

Media related to Phellamurin at Wikimedia Commons

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[1] "Phellamurin".

[2] Fortschritte der Chemie Organischer Naturstoffe. p. 17. ISBN 370918052X.

[3] Ma, Ji; Jones, Shannon H.; Hecht, Sidney M. (2005). "A Dihydroflavonol Glucoside from Commiphora a fricana that Mediates DNA Strand Scission". Journal of Natural Products. 68 (1): 115–117. doi:10.1021/np0400510. PMID 15679332.

[4] Honda, Keiichi; Hayashi, Nanao (1995). "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?". Journal of Chemical Ecology. 21 (10): 1531–1539. doi:10.1007/BF02035150. PMID 24233681. S2CID 8258780.

[5] Chiu, C. Y.; Li, C. Y.; Chiu, C. C.; Niwa, M.; Kitanaka, S.; Damu, A. G.; Lee, E. J.; Wu, T. S. (2005). "Constituents of leaves of Phellodendron japonicum MAXIM. And their antioxidant activity". Chemical & Pharmaceutical Bulletin. 53 (9): 1118–1121. doi:10.1248/cpb.53.1118. PMID 16141579.

[1]

[2]

[3]

[4]

[5]

v t e Flavanonols and their glycosides
3-Hydroxyflavanones:	Ampelopsin (Dihydromyricetin) Aromadedrin (Dihydrokaempferol) Dihydrogossypetin Dihydromorin Fustin (Dihydrofisetin) Garbanzol Pinobanksin 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

Names

IUPAC name (2R,3R)-7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
Systematic IUPAC name (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
Other names Fellavine 8-Prenyl dihydrokaempferol 7-glucoside Epimedoside C
Identifiers
CAS Number	52589-11-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8048^N
ChemSpider	168247^N
KEGG	C09808^N
MeSH	C016043
PubChem CID	193876
UNII	UXB86HY2NK^Y
CompTox Dashboard (EPA)	DTXSID00200563
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	518.515 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