Chemistry:Phellamurin
From HandWiki
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| Names | |
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| IUPAC name
(2R,3R)-7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
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| 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 | |
| Identifiers | |
3D model (JSmol)
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| KEGG | |
| MeSH | C016043 |
PubChem CID
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| Properties | |
| 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   ?)
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| Infobox references | |
Tracking categories (test):
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". https://pubchem.ncbi.nlm.nih.gov/compound/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. http://pubs.acs.org/doi/abs/10.1021/np0400510.
- ↑ 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. https://doi.org/10.1007%2FBF02035150.
- ↑ 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. https://pubmed.ncbi.nlm.nih.gov/16141579/.
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