Bioactive Formylated Flavonoids from Eugenia rigida: Isolation, Synthesis, and X-ray Crystallography.
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.
Department of Pharmacognosy, School of Pharmacy, Beni-Suef University , Beni-Suef, Egypt.
Mohamed A
MA
Zaki
N P Dhammika
NP
Nanayakkara
Department of Pharmacognosy, School of Pharmacy, Beni-Suef University , Beni-Suef, Egypt.
Mona H
MH
Hetta
Melissa R
MR
Jacob
Shabana I
SI
Khan
Department of Pharmacognosy, School of Pharmacy, Beni-Suef University , Beni-Suef, Egypt.
Rabab
R
Mohammed
Mohamed A
MA
Ibrahim
Volodymyr
V
Samoylenko
Christina
C
Coleman
Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803-1804, United States.
Frank R
FR
Fronczek
Daneel
D
Ferreira
Ilias
I
Muhammad
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D003455:Cryptococcus neoformans / Q000187:drug effects; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D000068856:Eugenia / Q000737:chemistry*; D044950:Flavanones; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D015269:Mycobacterium avium Complex / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011647:Puerto Rico; D013211:Staphylococcus aureus / Q000187:drug effects
C000620759:2',6'-dihydroxy-4'-methoxy-3'-methylchalcone; C502527:6-methylflavanone; D000972:Antineoplastic Agents, Phytogenic; D047188:Chalcones; D044950:Flavanones; D005419:Flavonoids; C117518:pinocembrin chalcone; C000620758:rac-6-formyl-5,7-dihydroxyflavanone; C043561:chrysin