TY  - JOUR
A1  - Hofmann, Julian
A1  - Fayez, Shaimaa
A1  - Scheiner, Matthias
A1  - Hoffmann, Matthias
A1  - Oerter, Sabrina
A1  - Appelt‐Menzel, Antje
A1  - Maher, Pamela
A1  - Maurice, Tangui
A1  - Bringmann, Gerhard
A1  - Decker, Michael
T1  - Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo
JF  - Chemistry – A European Journal
N2  - Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)‐1 and (S)‐1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC‐ECD coupling. (R)‐1 and (S)‐1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)‐enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short‐ and long‐term memory at low dosages.
KW  - Alzheimer′s disease
KW  - chiral resolution
KW  - circular dichroism
KW  - Eriodictyon californicum
KW  - flavonoids
KW  - sterubin
Y1  - 2020
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-215993
VL  - 26
IS  - 32
SP  - 7299
EP  - 7308
ER  - 
TY  - JOUR
A1  - Messi, Bernadette Biloa
A1  - Ndjoko-Ioset, Karine
A1  - Hertlein-Amslinger, Barbara
A1  - Lannang, Alain Meli
A1  - Nkengfack, Augustin E.
A1  - Wolfender, Jean-Luc
A1  - Hostettmann, Kurt
A1  - Bringmann, Gerhard
T1  - Preussianone, a New Flavanone-Chromone Biflavonoid from Garcinia preussii Engl.
JF  - Molecules
N2  - A new flavanone-chromone biflavonoid, preussianone (1), has been isolated from the leaves of Garcinia preussii, along with four known biflavonoids. The absolute stereostructures were elucidated by chemical, spectroscopic, and chiroptical methods. The biological properties of the new biflavonoid against several bacterial strains were evaluated.
KW  - multiflora
KW  - minimal inhibitory concentration
KW  - absolute configuration
KW  - circular dichroism
KW  - C-13 NMR
KW  - guttiferae
KW  - flavenoids
KW  - extractives
KW  - biflavanoids
KW  - livingstonei
KW  - high-temperature NMR
KW  - antibacterial activity
KW  - Garcinia biflavonoids
Y1  - 2012
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-130881
VL  - 17
IS  - 5
ER  - 
TY  - JOUR
A1  - Wang, Hui
A1  - Li, Min-Yi
A1  - Katele, Félix Zongwe
A1  - Satyanandamurty, Tirumani
A1  - Wu, Jun
A1  - Bringmann, Gerhard
T1  - Decandrinin, an unprecedented \(C_9\)-spiro-fused 7,8-\( seco-ent\)-abietane from the Godavari mangrove \(Ceriops\ decandra\)
JF  - Beilstein Journal of Organic Chemistry
N2  - Decandrinin (1), an unprecedented \(C_9\)-spiro-fused 7,8-\(seco-ent\)-abietane, was obtained from the bark of an Indian mangrove, \(Ceriops\ decandra\), collected in the estuary of Godavari, Andhra Pradesh. The constitution and the relative configuration of 1 were determined by HRMS (ESI) and extensive NMR investigations, and the absolute configuration by circular dichroism (CD) and optical-rotatory dispersion (ORD) spectroscopy in combination with quantum-chemical calculations. Decandrinin is the first 7,8-\(seco-ent\)-abietane.
KW  - ceriops decandra
KW  - abietane
KW  - absolute configuration
KW  - circular dichroism
KW  - decandrinin
KW  - rhizophoraceae
Y1  - 2014
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-119983
SN  - 1860-5397
VL  - 10
ER  -