135383-81-2Relevant articles and documents
Bioactive Formylated Flavonoids from Eugenia rigida: Isolation, Synthesis, and X-ray Crystallography
Zaki, Mohamed A.,Nanayakkara, N. P. Dhammika,Hetta, Mona H.,Jacob, Melissa R.,Khan, Shabana I.,Mohammed, Rabab,Ibrahim, Mohamed A.,Samoylenko, Volodymyr,Coleman, Christina,Fronczek, Frank R.,Ferreira, Daneel,Muhammad, Ilias
, p. 2341 - 2349 (2016/10/04)
Two new flavonoids, rac-6-formyl-5,7-dihydroxyflavanone (1) and 2′,6′-dihydroxy-4′-methoxy-3′-methylchalcone (2), together with five known derivatives, rac-8-formyl-5,7-dihydroxyflavanone (3), 4′,6′-dihydroxy-2′-methoxy-3′-methyldihydrochalcone (4), rac-7-hydroxy-5-methoxy-6-methylflavanone (5), 3′-formyl-2′,4′,6′-trihydroxy-5′-methyldihydrochalcone (6), and 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone (7), were isolated from the leaves of Eugenia rigida. The individual (S)- and (R)-enantiomers of 1 and 3, together with the corresponding formylated flavones 8 (6-formyl-5,7-dihydroxyflavone) and 9 (8-formyl-5,7-dihydroxyflavone), as well as 2′,4′,6′-trihydroxychalcone (10), 3′-formyl-2′,4′,6′-trihydroxychalcone (11), and the corresponding 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone (7) and 2′,4′,6′-trihydroxydihydrochalcone (12), were synthesized. The structures of the isolated and synthetic compounds were established via NMR, HRESIMS, and electronic circular dichroism data. In addition, the structures of 3, 5, and 8 were confirmed by single-crystal X-ray diffraction crystallography. The isolated and synthetic flavonoids were evaluated for their antimicrobial and cytotoxic activities against a panel of microorganisms and solid tumor cell lines.
Hydrogen-bonded rotamers of 2′,4′,6′-trihydroxy-3′-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum
Mustafa, Kamarul'Ain,Kjaergaard, Henrik G.,Perry, Nigel B.,Weavers, Rex T.
, p. 6113 - 6120 (2007/10/03)
Synthesis of 2′,4′,6′-trihydroxy-3′-methyldihydrochalcone, isolated as a natural product for the first time (ex Leptospermum recurvum), proceeds through 2′,4′,6′-trihydroxy-3′-formyldihydrochalcone. Two stable rotamers of this formyl derivative have been
