Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• -dihydroxyphenyl- and 3-methoxy-4-hydroxyphenyl moieties in the hesperidin, naringin, and rutin aglycones or silibinin). There are many studies revealing the interaction of flavonoids, flavonoid glycosides, and flavonolignans with CDs, especially for obtaining binary complexes [42][43][44][45][46][47][48][49]. In

• = 610.56 g/mol, purity ≥80%, other flavonoid glycosides as impurities), naringin hydrate (code “N”, C27H32O14·2H2O, M = 580.50 g/mol, purity ≥95%), rutin hydrate (code “R”, C27H30O16·xH2O, M = 610.52 g/mol, purity ≥94%), and silymarin (code “S”, C25H22O10, M = 482.44 g/mol, ≈70% silibinin A, other

• -cyclodextrin from the secondary face; (b) glyceryl 1,2-oleate 3-palmitate from hazelnut oil interacts with the β-cyclodextrin from the primary face, while silibinin A, the main component of silymarin, interacts with β-cyclodextrin from the secondary face. Superposition of the FTIR spectra for the β

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

• Guozheng Huang,
• Simon Schramm,
• Jörg Heilmann,
• David Biedermann,
• Vladimír Křen and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

• ®, a drug approved for treatment of chronic hepatitis, hepatoprotection in alcohol addicts [2], or intoxication with Amanita phalloides, the death cap [3]. Silibinin (1, Figure 1), the major component of silymarin, became the first isolated flavonolignan [4]. Besides 1, this extract consists also of

• isosilibinin (3), silychristin (5), silydianin (11), and dehydrosilibinin [1][5]. Natural and commercially available silibinin is the diastereomeric mixture (quasi equimolar) of silybin A (1a) and silybin B (1b). Because of the well-known biological properties of silibinin and the other compounds of the

• , our group has developed a hybrid drug combining silibinin with tacrine (a potent acetylcholinesterase inhibitor for treatment of Alzheimer’s disease), which shows neuro- and hepatoprotective effects exceeding the cytoprotective effects of silibinin and effectively counteracts tacrine’s dose-dependent

cis–trans Isomerization of silybins A and B

• Michaela Novotná,
• Radek Gažák,
• David Biedermann,
• Florent Di Meo,
• Petr Marhol,
• Marek Kuzma,
• Lucie Bednárová,
• Kateřina Fuksová,
• Patrick Trouillas and
• Vladimír Křen

Beilstein J. Org. Chem. 2014, 10, 1047–1063, doi:10.3762/bjoc.10.105

• ; 10,11-cis-silybin; isomerization; silibinin; silybin; silymarin; Introduction The flavonolignan silybin (alternative name silibinin), occurring in the fruits of Silybum marianum (milk thistle), consists of two stereoisomers – silybin A (1a) and B (1b) – in a ca. 1:1 ratio (Figure 1). Their absolute