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

• solubility and bioaccessibility of the hazelnut oil components and antioxidants can be increased, as well as the controlled release of bioactive compounds (fatty acid glycerides and antioxidant flavonoids, namely hesperidin, naringin, rutin, and silymarin). The appropriate method for obtaining the ternary

• silymarin) are flavanonol derivatives, having a coniferyl alcohol moiety connected through the hydroxy groups in the 3’ and 4’ positions of the aglycone (Figure 1b). FTIR analysis of these flavonoids revealed stretching and bending vibrations corresponding to OH bonds (phenolic or alcoholic, glycosidic and

• cm−1. The lowest value for this band was observed for silymarin at 1634.1 (± 0.4) cm−1 and the highest one for rutin at 1651 (± 0.1) cm−1. For hesperidin and naringin this band appears at approximately the same value (≈1645 cm−1). The stretching vibrations of phenolic, glycosidic or water O–H bonds

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

• multiple biological activities and promising therapeutic applications, such as hepatoprotection, antitumor, antiproliferative and anti-oxidant properties [1]. The standardized extract of S. marianum fruits contains the so-called silymarin complex, and is used as the main active component mixture of Legalon

• ®, 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

• silymarin complex for protection of liver damage, and for preventing skin tumor promotion, these compounds have attracted efforts on their total synthesis (e.g., isosilybin) [6] and structural modification [5][7][8][9] to improve their water-solubility, bioavailability and biological activities. Recently

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

• configuration is known [1][2] and their separation was accomplished recently [3][4][5]. Both silybin isomers as well as other flavonolignans from silymarin (crude defatted extract from the fruits of S. marianum) are products of a phenolic oxidative coupling of the flavonoid taxifolin and the lignan coniferyl

• alcohol. The mechanism of this coupling reaction was described [6] and implied a 10,11-trans relative configuration, as in all the major components of silymarin. Little is known about the structures of the minor components of silymarin. It was speculated that some of them were 10,11-cis-analogues of the