Polygonophenone, the first MEM-substituted natural product, from Polygonum maritimum.
An unprecedented natural acetophenone, polygonophenone (1), and a new resorcinol, polygonocinol (2), were isolated from the dichloromethane and methanol extracts of Polygonum maritimum and identified as 2-hydroxy-4-[(2-methoxyethoxy)methoxy] acetophenone and 2-methyl-5-nonadecylresorcinol, respectively. In addition, 11 known compounds were identified, namely, the sesquiterpenoid (+)-8-hydroxycalamene, four ferulic acid esters (tetracosyl, hexacosyl, octacosyl, and triacontyl ferulate), the arylpropane broussonin B, the flavonoids quercetin, quercitrin, and (+)-catechin, the hydroquinone glucoside isotachioside, and beta-sitosterol. The structures of the new compounds were elucidated on the basis of their NMR and MS data. It is noteworthy that polygonophenone (1) is the first naturally methoxyethoxymethyl (MEM)-substituted natural product, and its isolation gives support for the use of MEM protection in biomimetic synthetic schemes.
Kazantzoglou
Georgios
G
Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Panepistimiopolis Zografou, 15771 Athens, Greece.
Magiatis
Prokopios
P
Kalpoutzakis
Eleftherios
E
Skaltsounis
Alexios-Leandros
AL
D000098:Acetophenones / Q000737:chemistry / Q000302:isolation & purification*; D005019:Ethyl Ethers / Q000737:chemistry*; D006115:Greece; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D028502:Polygonum / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry / Q000302:isolation & purification*
D000098:Acetophenones; D005019:Ethyl Ethers; D012118:Resorcinols; C550410:polygonophenone; C031389:resorcinol